JPH0362810A - Polysiloxane-coating water-dispersion type resin composition - Google Patents
Polysiloxane-coating water-dispersion type resin compositionInfo
- Publication number
- JPH0362810A JPH0362810A JP19975789A JP19975789A JPH0362810A JP H0362810 A JPH0362810 A JP H0362810A JP 19975789 A JP19975789 A JP 19975789A JP 19975789 A JP19975789 A JP 19975789A JP H0362810 A JPH0362810 A JP H0362810A
- Authority
- JP
- Japan
- Prior art keywords
- group
- acid
- formula
- carbon atoms
- polysiloxane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000011342 resin composition Substances 0.000 title claims description 10
- 238000000576 coating method Methods 0.000 title abstract description 6
- 239000011248 coating agent Substances 0.000 title description 5
- 239000006185 dispersion Substances 0.000 title 1
- -1 polysiloxane group Polymers 0.000 claims abstract description 95
- 239000000178 monomer Substances 0.000 claims abstract description 56
- 239000000203 mixture Substances 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 229920001296 polysiloxane Polymers 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 239000004908 Emulsion polymer Substances 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 24
- 239000000853 adhesive Substances 0.000 abstract description 5
- 230000001070 adhesive effect Effects 0.000 abstract description 5
- 238000003860 storage Methods 0.000 abstract description 5
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 4
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 2
- 229930195733 hydrocarbon Natural products 0.000 abstract description 2
- 238000007334 copolymerization reaction Methods 0.000 abstract 2
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- 238000000034 method Methods 0.000 description 24
- 239000000839 emulsion Substances 0.000 description 20
- 238000006116 polymerization reaction Methods 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000003995 emulsifying agent Substances 0.000 description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000010556 emulsion polymerization method Methods 0.000 description 3
- 238000007720 emulsion polymerization reaction Methods 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 239000004310 lactic acid Substances 0.000 description 3
- 235000014655 lactic acid Nutrition 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 239000002563 ionic surfactant Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- ZJCZFAAXZODMQT-UHFFFAOYSA-N 2-methylpentadecane-2-thiol Chemical compound CCCCCCCCCCCCCC(C)(C)S ZJCZFAAXZODMQT-UHFFFAOYSA-N 0.000 description 1
- NDAJNMAAXXIADY-UHFFFAOYSA-N 2-methylpropanimidamide Chemical compound CC(C)C(N)=N NDAJNMAAXXIADY-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229930182843 D-Lactic acid Natural products 0.000 description 1
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-araboascorbic acid Natural products OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- PQUCIEFHOVEZAU-UHFFFAOYSA-N Diammonium sulfite Chemical compound [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 239000002211 L-ascorbic acid Substances 0.000 description 1
- 235000000069 L-ascorbic acid Nutrition 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- ZPOLOEWJWXZUSP-WAYWQWQTSA-N bis(prop-2-enyl) (z)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C/C(=O)OCC=C ZPOLOEWJWXZUSP-WAYWQWQTSA-N 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- RZMWTGFSAMRLQH-UHFFFAOYSA-L disodium;2,2-dihexyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCC RZMWTGFSAMRLQH-UHFFFAOYSA-L 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000004318 erythorbic acid Substances 0.000 description 1
- 235000010350 erythorbic acid Nutrition 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229940026239 isoascorbic acid Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 238000004162 soil erosion Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- GEKDEMKPCKTKEC-UHFFFAOYSA-N tetradecane-1-thiol Chemical compound CCCCCCCCCCCCCCS GEKDEMKPCKTKEC-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明はポリシロキサン含有水分散型樹脂組成物に関す
る。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a water-dispersed resin composition containing polysiloxane.
ポリシロキサン基を含む水分散型樹脂を得る場合、あら
かじめポリシロキサン化合物（ポリジメチルシロキサン
やポリメチルビニルシロキサンなど）の乳化物を作製し
、この乳化物中で乳化剤の存在下にエチレン性不飽和単
量体を乳化重合により得る技術や、片末端不飽和のポリ
シロキサン含有単量体とエチレン性不飽和単量体とを電
解質の存在下に、乳化剤を使用して乳化重合により得る
技術がある。前者の乳化剤としてたとえば、ドデシルベ
ンゼンスルホン酸塩などがあり（特開昭５０−１０９２
８２号公報）、後者の乳化剤としてたとえば、ジアルキ
ルスルホコハク酸塩などがある（特開昭６３−１９１８
０７号公報）。When obtaining a water-dispersed resin containing a polysiloxane group, an emulsion of a polysiloxane compound (polydimethylsiloxane, polymethylvinylsiloxane, etc.) is prepared in advance, and an ethylenically unsaturated monomer is added to the emulsion in the presence of an emulsifier. There is a technique for obtaining a polymer by emulsion polymerization, and a technique for obtaining a polysiloxane-containing monomer having one end unsaturated and an ethylenically unsaturated monomer by emulsion polymerization using an emulsifier in the presence of an electrolyte. Examples of the former emulsifier include dodecylbenzenesulfonate (Japanese Patent Application Laid-Open No. 1092-1989)
82), and examples of the latter emulsifiers include dialkyl sulfosuccinates (Japanese Patent Application Laid-open No. 1918-1983).
Publication No. 07).
しかしながら、これらのポリシロキサン含有水分散型樹
脂組成物は貯蔵安定性が十分でなく、またこれらの水分
散型樹脂組成物から作製された重合体フィルムの撥水性
や平滑性が十分でないなどという問題点がある。However, these polysiloxane-containing water-dispersed resin compositions do not have sufficient storage stability, and the polymer films made from these water-dispersed resin compositions have problems such as insufficient water repellency and smoothness. There is a point.
本発明者らはポリシロキサン含有水分散型樹脂組成物の
貯蔵安定性が良好であり、さらにこれらの水分散型樹脂
組成物から作製された重合体フィルムが改善された撥水
性及び平滑性を有するポリシロキサン含有水分散型樹脂
組成物を開発すべく鋭意研究した結果本発明に達した。The present inventors have demonstrated that polysiloxane-containing water-dispersed resin compositions have good storage stability, and that polymer films made from these water-dispersed resin compositions have improved water repellency and smoothness. The present invention was achieved as a result of intensive research to develop a water-dispersed resin composition containing polysiloxane.
すなわち本発明は、
一般式
（式中、Ｒ１は水素原子またはメチル基Ｎ Ｒ２、Ｒ
３はそれぞれ炭素数１−１０のアルキル基である。That is, the present invention is based on the general formula (wherein R1 is a hydrogen atom or a methyl group N R2, R
3 each represents an alkyl group having 1 to 10 carbon atoms.
Ｒ４は炭素数３〜２５のアルキル基である。）で示され
るアミンイミド化合物（Ａ Ｉ）及び／または一般式
（式中、ＲＩは水素原子またはメチル基、Ｒ２、Ｒ３は
それぞれ炭素数１〜１０のアルキル基である。R4 is an alkyl group having 3 to 25 carbon atoms. ) and/or the general formula (where RI is a hydrogen atom or a methyl group, and R2 and R3 are each an alkyl group having 1 to 10 carbon atoms).
Ｒ６は炭素数４〜２８の飽和もしくは不飽和の脂肪族炭
化水素基、または（置換）フェニル基である。）で示さ
れるアミンイミド化合物（Ａ２）と一般式
％式％（）
（３）
（式中、Ｘはビニル基、 （メタ）アクリロキシ基また
はアリル基、Ｒ６は２価の炭化水素基、Ｒ７、Ｒ８、Ｒ
９は水素原子、炭素数１〜１０のアルキル基またはフェ
ニル基、ｎ＝１〜１３０である。）で示されるポリシロ
キサン基を含有する不飽和単量体（Ｂ）及びこれらと共
重合可能なエチレン性不飽和単量体（ｃ）との共重合物
からなることを特徴とするポリシロキサン含有水分散型
樹脂組成物である。R6 is a saturated or unsaturated aliphatic hydrocarbon group having 4 to 28 carbon atoms or a (substituted) phenyl group. ) and the general formula % formula % () (3) (wherein, X is a vinyl group, a (meth)acryloxy group or an allyl group, R6 is a divalent hydrocarbon group, R7, R8 ,R
9 is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or a phenyl group, n=1 to 130; ) A polysiloxane-containing product comprising a copolymer of an unsaturated monomer (B) containing a polysiloxane group shown in ) and an ethylenically unsaturated monomer (c) copolymerizable with these monomers It is a water-dispersed resin composition.
一般式（１）及び一般式（２）においてＲ２、Ｒ３の炭
素数１−１０のアルキル基としては直鎖または分岐のア
ルキル基、たとえばメチル、エチル、ｎ−プロピル、イ
ソプロピル、ｎ−ブチル、イソブチル、ヘキシル、オク
チル基などがあげられる。これらのうちで好ましいもの
はメチル、エチル、及びｎ−またはイソプロピル基であ
り、特に好ましいのはメチル基である。In general formula (1) and general formula (2), the alkyl group having 1 to 10 carbon atoms in R2 and R3 is a straight chain or branched alkyl group, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl. , hexyl, octyl, etc. Preferred among these are methyl, ethyl, and n- or isopropyl groups, with methyl being particularly preferred.
また、一般式（１）においてＲ４の炭素数３〜２５のア
ルキル基としてはプロピル、ブチル、イソブチル、アミ
ル、ヘキシル、ヘプチル、オクチル、２−エチルへ牛シ
ル、ノニル、デシル、ウンデシル、トリデシル、テトラ
デシル、ペンタデシル、ヘキサデシル、ヘプタデシル、
オクタデシル、ノナデシル、エイフシル基なとの直鎖ま
たは分岐鎖を有するアルキル基があげられる。これらの
うちで好ましいものは、炭素数７〜１５の直鎖もしくは
分岐鎖を有するアルキル基である。In general formula (1), the alkyl group having 3 to 25 carbon atoms for R4 is propyl, butyl, isobutyl, amyl, hexyl, heptyl, octyl, 2-ethyl, bovine syl, nonyl, decyl, undecyl, tridecyl, tetradecyl. , pentadecyl, hexadecyl, heptadecyl,
Examples include straight-chain or branched alkyl groups such as octadecyl, nonadecyl, and eifyl groups. Among these, preferred are straight-chain or branched alkyl groups having 7 to 15 carbon atoms.
また、一般式（２）においてＲ５の炭素数４〜２８の飽
和もしくは不飽和の脂肪族炭化水素基としてはブチル、
ヘキシル、オクチル、２−エチルヘキシル、ノニル、デ
シル、 ドデシル、 トリデシル、テトラデシル、ヘプ
タデシル、ヘキサデシル、オクタデシル、オレイル、エ
イコシル基などのアルキル基またはアルケニル基があげ
られる。これらのうちで好ましいものは、炭素数１０〜
１８の飽和もしくは不飽和の直鎖もしくは分岐鎖を有す
る脂肪族炭化水素基である。置換フェニル基としては、
炭素数１〜１８のアルキル基を有するフェニル基（クレ
ジル、ｎ−ブチルフェニル、ｔ−ブチルフェニル、オク
チルフェニル、ノニルフェニル、ドデシルフェニルなど
）、アリールフェニル基（ビフェニルなど）、アラルキ
ルフェニル基（クミルフェニル、スチレン化フェニルな
ど）などがあげられる。これらのうちで好ましいものは
、炭素数１〜１８のアルキル基を有するフェニル基であ
る。In addition, in the general formula (2), the saturated or unsaturated aliphatic hydrocarbon group having 4 to 28 carbon atoms for R5 is butyl,
Examples include alkyl or alkenyl groups such as hexyl, octyl, 2-ethylhexyl, nonyl, decyl, dodecyl, tridecyl, tetradecyl, heptadecyl, hexadecyl, octadecyl, oleyl, and eicosyl groups. Among these, preferable ones have 10 to 10 carbon atoms.
It is an aliphatic hydrocarbon group having 18 saturated or unsaturated straight or branched chains. As substituted phenyl group,
Phenyl groups having an alkyl group having 1 to 18 carbon atoms (cresyl, n-butylphenyl, t-butylphenyl, octylphenyl, nonylphenyl, dodecylphenyl, etc.), arylphenyl groups (biphenyl, etc.), aralkylphenyl groups (cumylphenyl, styrenated phenyl, etc.). Among these, preferred is a phenyl group having an alkyl group having 1 to 18 carbon atoms.
一般式（１）で示される化合物の具体例としてはたとえ
ば、
ＣＩ３
ＣＨ３
ＣＨ２＝ＣＣＯＮ
Ｎ’ＣＨ２ＣＨＣｔ（２
５Ｈｚ
（ＡＩ−１）
Ｈａ
Ｈ
ＣＩ３
Ｈｓ
０■
Ｈａ
Ｈｓ
ＣＩ！３
Ｈ
などがあげられる。Specific examples of the compound represented by the general formula (1) include CI3 CH3 CH2=CCON N'CH2CHCt(2 5Hz (AI-1) Ha H CI3 Hs 0■ Ha Hs CI!3 H, etc.).
一般式（２）
でホされる化合物の具体例として
はたとえば、
ＣＩ（３
Ｈ
Ｈａ
０■
ｈ
０１（
ＣＨ３
ＣＨ３
ＣＨ２
Ｃ０Ｎ
Ｎ“ＣＨ２ＣＨＣＨ２０Ｃ＋ｓＨ３□
（Ａ１
１２）
ＣＩ＋３
Ｈ
ＣＨ２”ＣＧＯＮ−Ｎ”ＣＨ２ＣＨＣＨ２０ＣａＨ４−
Ｃ９Ｌ＊（Ａ１
１３）
ＣＨ３
Ｈ
Ｏ
などがあげられる。Specific examples of compounds represented by the general formula (2) include CI(3 H Ha 0 ■ h 01 ( CH3 CH3 CH2 C0N N"CH2CHCH20C+sH3□ (A1 12) CI+3 H CH2"CGON-N"CH2CHCH20CaH4-
Examples include C9L*(A1 13) CH3H O.
一般式（１）で示されるアミンイミド化合物は、炭素数
６〜２８の１，２−エポキシアルカンと（メタ）アクリ
ル酸エステルと非対称ジアルキルヒドラジンとを反応さ
せることによって得ることができる。The amine imide compound represented by the general formula (1) can be obtained by reacting a 1,2-epoxyalkane having 6 to 28 carbon atoms, a (meth)acrylic acid ester, and an asymmetric dialkylhydrazine.
一般式（２）で示されるアミンイミド合物は、炭素数４
〜２８のアルキルもしくはアルケニルグリシジルエーテ
ル化合物または（置換）フェニルグリシジルエーテル化
合物から選ばれるグリシジルエーテル化合物と（メタ）
アクリル酸エステルと非対称ジアルキルヒドラジンとを
反応させることによって得ることができる。The amine imide compound represented by the general formula (2) has 4 carbon atoms.
-28 alkyl or alkenyl glycidyl ether compounds or (substituted) phenyl glycidyl ether compounds and (meth)
It can be obtained by reacting an acrylic acid ester with an asymmetric dialkylhydrazine.
一般式（１）または（２）で示されるアミンイミド化合
物は、必要によりアルコール、ケトン、エーテル、芳香
族炭化水素などの溶剤の存在下に、■（メタ）アクリル
酸エステル、非対称ジアルキルヒドラジン及び１，２−
エポキシアルカンもしくはグリシジルエーテル化合物の
３者を同時に反応させる方法、■１，２−エポキシアル
カンもしくはグリ１１−
シジルエーテル化合物と非対称ジアルキルヒドラジンを
反応させてから（メタ）アクリル酸エステルを反応させ
る方法などがあげられる。The amine imide compound represented by the general formula (1) or (2) is prepared by preparing (meth)acrylic acid ester, asymmetric dialkylhydrazine and 1, 2-
Methods include a method in which three components, an epoxy alkane or a glycidyl ether compound, are reacted simultaneously, and a method in which a 1,2-epoxy alkane or a glycidyl ether compound is reacted with an asymmetric dialkyl hydrazine, and then a (meth)acrylic acid ester is reacted. can give.
一般式（３）においてＮ Ｒ６の２価の炭化水素基と
してはアルキレン基やフェニレン基などがあり、アルキ
レン基としては、たとえばエチレン基、プロピレン基、
ブチレン基、ヘキシレン基などがあり、好ましいのはプ
ロピレン基である。In general formula (3), divalent hydrocarbon groups of N R6 include alkylene groups and phenylene groups, and examples of alkylene groups include ethylene groups, propylene groups,
Examples include butylene group, hexylene group, etc., and propylene group is preferred.
また、一般式（３）において、Ｒ７、Ｒ８、Ｒ９の炭素
数１−１０のアルキル基としては、たとえばメチル基、
エチル基、プロピル基、ブチル基などがあり、好ましい
のはメチル基である。３個のＲ９は同一でも異なってい
てもよい。In addition, in the general formula (3), examples of the alkyl group having 1 to 10 carbon atoms in R7, R8, and R9 include a methyl group,
Examples include ethyl group, propyl group, butyl group, and methyl group is preferred. The three R9s may be the same or different.
一般式（３）で示される単量体の具体例としてはたとえ
ば、
Ｈ３
２
Ｈａ
Ｈｓ
Ｃ，Ｈ。Specific examples of the monomer represented by general formula (3) include H3 2 Ha Hs C,H.
ｓ Ｒ５ （ｎ ｌ〜１３０） など及びこれらの２種以上の混合物があげられる。s R5 (n l~130) and mixtures of two or more thereof.
本発明のポリシロキサン含有水分散型樹組酸物（以下、
本発明の組成物という。）に使用されるエチレン性不飽
和単量体（ｃ）としては疎水性エチレン性不飽和単量体
（Ｉ）と親水性エチレン性不飽和単量体（ＩＩ）があげ
られる。 （Ｉ）としては下記の単量体があげられる。The polysiloxane-containing water-dispersible resin acid of the present invention (hereinafter referred to as
It is referred to as a composition of the present invention. Examples of the ethylenically unsaturated monomer (c) used in ) include hydrophobic ethylenically unsaturated monomer (I) and hydrophilic ethylenically unsaturated monomer (II). Examples of (I) include the following monomers.
ａ、ニトリル基含有単量体； （メタ）アクリロニトリルなど。a, nitrile group-containing monomer; (meth)acrylonitrile etc.
ｂ、不飽和カルボン酸〔（メタ）アクリル酸、マレイン
酸、フマル酸、イタコン酸など〕エステル系単量体；
炭素数１〜２０のアルキル基を有する（メタ）アクリル
酸エステル〔（メタ）アクリル酸メチル、（メタ）アク
リル酸エチル、 （メタ）アクリル酸イソブチル、 （
メタ）アクリル酸ｎ−ブチル、（メタ）アクリル酸２−
エチルヘキシル、 （メタ）アクリル酸ドデシルなど〕
； グリコール（エチレングリコール、プロピレングリ
コール、ポリプロピレングリコール、ｌ、４−ブタンジ
オールなど）の（メタ）アクリル酸ジエステル： （メ
タ）アクリル酸グリシジル；マレイン酸、イタコン酸、
フマル酸などのジまたはモノアルキルエステル； （メ
タ）アクリル酸ヒドロキシエチルのカプロラクトン変性
物など。b, unsaturated carboxylic acid [(meth)acrylic acid, maleic acid, fumaric acid, itaconic acid, etc.] ester monomer; (meth)acrylic acid ester having an alkyl group having 1 to 20 carbon atoms [(meth)acrylic acid Methyl acid, ethyl (meth)acrylate, isobutyl (meth)acrylate, (
n-butyl meth)acrylate, 2-(meth)acrylate
Ethylhexyl, dodecyl (meth)acrylate, etc.]
; (meth)acrylic diester of glycol (ethylene glycol, propylene glycol, polypropylene glycol, l,4-butanediol, etc.): glycidyl (meth)acrylate; maleic acid, itaconic acid,
Di- or monoalkyl esters such as fumaric acid; caprolactone-modified products of hydroxyethyl (meth)acrylate, etc.
Ｃ９芳香族炭化水素系単量体；
スチレン、α−メチルスチレン、ビニルトルエン、ジビ
ニルベンゼンなど。C9 aromatic hydrocarbon monomer; styrene, α-methylstyrene, vinyltoluene, divinylbenzene, etc.
ｄ、ハロゲン含有炭化水素系単量体；
塩化ビニル、塩化ビニリデン、クロロスチレン、クロロ
プレンなど。d. Halogen-containing hydrocarbon monomer; vinyl chloride, vinylidene chloride, chlorostyrene, chloroprene, etc.
ｅ、脂肪族炭化水素系単量体；
エチレン、プロピレン、α−オレフィン、ブタジェン、
イソプレンなど。e, aliphatic hydrocarbon monomer; ethylene, propylene, α-olefin, butadiene,
such as isoprene.
ｆ、ビニルエステル単量体； 酢酸ビニル、プロピオン酸ビニルなど。f, vinyl ester monomer; Vinyl acetate, vinyl propionate, etc.
ｇ、（メタ）アリルエステル系単量体；アリル酢酸エス
テル、ジアリルフタル酸エステル、ジアリルマレイン酸
エステルなど。g, (meth)allyl ester monomer; allyl acetate, diallyl phthalate, diallyl maleate, etc.
（ＩＩ）としては下記の単量体があげられる。Examples of (II) include the following monomers.
ｈ、アミノ基またはアミド基含有不飽和単量体；（メタ
）アクリルアミド、Ｎ、Ｎ−ジメチル（メタ）１５−
アクリルアミド、ジアセトン（メタ）アクリルアミド、
Ｎ−メチロール（メタ）アクリルアミド、ジメチルアミ
ノエチル（メタ）アクリルアミド、ジメチルアミノプロ
ピル（メタ）アクリルアミド、 （メタ）アクリル酸ジ
メチルアミノエチル、（メタ）アクリル酸ジエチルアミ
ノエチル、Ｎビニル−２−ピロリドンなど。h, unsaturated monomer containing an amino group or an amide group; (meth)acrylamide, N,N-dimethyl (meth)15-acrylamide, diacetone (meth)acrylamide,
N-methylol (meth)acrylamide, dimethylaminoethyl (meth)acrylamide, dimethylaminopropyl (meth)acrylamide, dimethylaminoethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, N-vinyl-2-pyrrolidone, etc.
ｉ、不飽和カルボン酸及びその塩；
（メタ）アクリル酸、マレイン酸、フマル酸、イタコン
酸など及びそれらの塩（アルカリ金属塩、アンモニウム
塩、アミン塩など）。i. Unsaturated carboxylic acids and their salts; (meth)acrylic acid, maleic acid, fumaric acid, itaconic acid, etc. and their salts (alkali metal salts, ammonium salts, amine salts, etc.).
ｊ、エステル基含有親水性アクリル系単量体；（メタ）
アクリル酸２−ヒドキシエチル、 （メタ）アクリル酸
２−ヒドキシプロピル、ポリエチレングリコール（メタ
）アクリル酸モノまたはジエステル、ポリエチレングリ
コール低級アルキルエーテル（メタ）アクリル酸エステ
ルなど。j, ester group-containing hydrophilic acrylic monomer; (meth)
2-Hydoxyethyl acrylate, 2-hydroxypropyl (meth)acrylate, polyethylene glycol (meth)acrylic acid mono- or diester, polyethylene glycol lower alkyl ether (meth)acrylic ester, etc.
ｋ、アミンイミド基含有アクリル系単量体〔本発明の一
般式（１）及び（２）で示されるアミンイミド化合物は
除＜〕；
６−
Ｎ、Ｎ−ジメチル−Ｎ−（２−ヒドロキシプロピル）ア
ミンメタクリルイミド、Ｎ、Ｎ、Ｎ−）リメチルアミン
メタクリルイミド、及び特願昭６３−１９３０３１号明
細書に記載の一般式（１）の化合物など
本発明の組成物に使用されるエチレン性不飽和単量体（
ｃ）としては（Ｉ）、及び（Ｉ）と（ＩＩ）の併用系が
用いられる。k, amine imide group-containing acrylic monomer [excluding amine imide compounds represented by general formulas (1) and (2) of the present invention]; 6-N,N-dimethyl-N-(2-hydroxypropyl)amine Ethylenically unsaturated compounds used in the composition of the present invention, such as methacrylimide, N,N,N-)limethylamine methacrylimide, and the compound of general formula (1) described in Japanese Patent Application No. 193031/1983 Monomer (
As c), (I) and a combination system of (I) and (II) are used.
本発明の組成物を構成する一般式（１）で示されるアミ
ンイミド化合物（Ａ１）及び／または一般式（２）で示
されるアミンイミド化合物（Ａ２）とポリシロキサン含
有不飽和単量体（Ｂ）、及びこれらと共重合可能なエチ
レン性不飽和単量体（ｃ）の使用量は全単量体の合計重
量に基づいて（Ａ１）及び／または（Ａ２）が通常０．
５〜３０％、好ましくは１〜２０％、 （Ｂ）が通常Ｉ
〜５０％、好ましくは５〜５０％、 （ｃ）が通常２０
〜９８．５％、好ましくハ３ｏ〜９４％である。 （Ａ
１）及び／または（Ａ２） カ０．５％未満では本発明
の組成物の乳化安定性が悪くなり、３０％を越えると本
発明の組成物の乾燥塗膜の耐水性が低下する。また（Ｂ
）が１％未満では本発明の組成物の撥水性や平滑性が十
分でなく、５０％を越えると経済性の点で不利である。An amine imide compound (A1) represented by the general formula (1) and/or an amine imide compound (A2) represented by the general formula (2) constituting the composition of the present invention and a polysiloxane-containing unsaturated monomer (B), The amount of the ethylenically unsaturated monomer (c) copolymerizable with these monomers (A1) and/or (A2) is usually 0.5% based on the total weight of all monomers.
5-30%, preferably 1-20%, (B) is usually I
~50%, preferably 5-50%, (c) usually 20
-98.5%, preferably C3o -94%. (A
1) and/or (A2) If the amount is less than 0.5%, the emulsion stability of the composition of the present invention will deteriorate, and if it exceeds 30%, the water resistance of the dried coating film of the composition of the present invention will be decreased. Also (B
) is less than 1%, the water repellency and smoothness of the composition of the present invention will not be sufficient, and if it exceeds 50%, it is disadvantageous in terms of economic efficiency.
本発明の組成物は、乳化重合法、または溶液重合もしく
は塊状重合したのち得られた樹脂を水に分散させる方法
などにより製造することができ、好ましいのは乳化重合
法である。The composition of the present invention can be produced by an emulsion polymerization method or a method of dispersing the obtained resin in water after solution polymerization or bulk polymerization, and the emulsion polymerization method is preferred.
乳化重合法としては一般式（１）で示されるアミンイミ
ド化合物（Ａ Ｉ）及び／または一般式（２）で示され
るアミンイミド化合物（Ａ２）を乳化剤として使用し、
必要によりｐｌ調整剤や重合連鎖移動剤の存在下、種々
の重合開始方法により（Ａ Ｉ）及び／または（Ａ２）
とポリシロキサン基を含有する不飽和単量体（Ｂ）、及
びこれらと共重合可能なエチレン性不飽和単量体（ｃ）
を水系媒体中で重合することにより得られる。In the emulsion polymerization method, an amine imide compound (AI) represented by general formula (1) and/or an amine imide compound (A2) represented by general formula (2) is used as an emulsifier,
(A I) and/or (A2) by various polymerization initiation methods in the presence of a PL adjuster or a polymerization chain transfer agent if necessary.
and an unsaturated monomer (B) containing a polysiloxane group, and an ethylenically unsaturated monomer (c) copolymerizable with these.
obtained by polymerizing in an aqueous medium.
溶液重合もしくは塊状重合したのち得られた樹脂を水に
分散させる方法としては、一般式（１）で示されるアミ
ンイミド化合物（Ａ、）及び／または一般式（２）で示
されるアミンイミド化合物（Ａ ２ ）とポリシロキサ
ン県を含有する不飽和単量体（Ｂ）、及びこれらと共重
合可能なエチレン性不飽和単量体（ｃ）を、必要により
重合連鎖移動剤の存在下に、種々の重合開始方法により
溶媒（アルコール、ケトン、エーテル、芳香族炭化水素
など）中またはそのまま共重合し、得られた樹脂を必要
によりｐ）Ｉ調整剤の存在下に水系媒体中に分散させて
得ることができる。As a method for dispersing the resin obtained after solution polymerization or bulk polymerization in water, an amine imide compound (A, ) represented by general formula (1) and/or an amine imide compound (A 2 ) represented by general formula (2) is used. ), an unsaturated monomer (B) containing a polysiloxane, and an ethylenically unsaturated monomer (c) copolymerizable with these, in the presence of a polymerization chain transfer agent if necessary, are subjected to various polymerizations. Depending on the initiation method, the resin can be copolymerized in a solvent (alcohol, ketone, ether, aromatic hydrocarbon, etc.) or directly, and the resulting resin can be dispersed in an aqueous medium, optionally in the presence of a p)I modifier. can.
ｐＨ調整剤としては酸（塩酸、燐酸、酢酸、コハク酸、
ホウ酸、炭酸など）、その塩（炭酸ナトリウム、 酢酸
ナト リウム、 ト リポリ リ ン酸ナト リウム
など）、塩基〔アルカリ金属の水酸化物（水酸化カリウ
ム、水酸化ナトリウムなど）、水酸化アンモニウム、ア
ミンなど〕があげられる。Acids (hydrochloric acid, phosphoric acid, acetic acid, succinic acid,
boric acid, carbonic acid, etc.), their salts (sodium carbonate, sodium acetate, sodium tripolyphosphate, etc.), bases [alkali metal hydroxides (potassium hydroxide, sodium hydroxide, etc.), ammonium hydroxide, amines, etc.).
重合連鎖移動剤としては、たとえばメルカプタン（ドデ
シルメルカプタン、テトラデシルメルカプタン、ヘキサ
デシルメルカプタン、２−メルカプトエタノールなど）
、二硫化キサントゲン、硫黄、ニトロソ化合物、アミン
などがあげられる。Examples of polymerization chain transfer agents include mercaptans (dodecylmercaptan, tetradecylmercaptan, hexadecylmercaptan, 2-mercaptoethanol, etc.)
, xanthogen disulfide, sulfur, nitroso compounds, amines, etc.
水系媒体としては、水のほかにメタノール、工＋９−
タノール、イソプロパツール、アセトン、エチレングリ
コール、ジエチレングリコール、 トリエチレングリコ
ール、プロピレングリコール、エチレングリコールモノ
メチルエーテル、エチレングリコールモノエチルエーテ
ル、エチレングリコールモノブチルエーテル、プロピレ
ングリコールモノメチルエーテル、ジエチレングリコー
ルモノメチルエーテルなどの有機溶剤を併用してもよい
。In addition to water, aqueous media include methanol, ethanol, isopropanol, acetone, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, Organic solvents such as propylene glycol monomethyl ether and diethylene glycol monomethyl ether may be used in combination.
重合方法としては電子線または紫外線を照射する方法、
加熱による方法及び開始剤を使用する方法などがあげら
れる。開始剤を使用する方法において、開始剤としては
アゾ化合物〔アゾビスイソブチロニトリル、２．２’−
アゾビス（２，４−ジメチルバレロニトリル）、アゾビ
スシアノ吉草酸、２，２−アゾビス（２−アミジノプロ
パン）ハイドロクロライド、２．２−アゾビス（２−ア
ミジノプロパン）アセテートなど〕、無機過酸化物〔過
酸化水素、過硫酸アンモニウム、過硫酸カリウム、過硫
酸ナトリウムなど〕、有機過酸化物〔過酸化ベンゾイル
、ジｔ−ブチルパーオキサイド、クメンヒドロパーオ２
０−
キサイド酸パーオキサイド、ジ（２−エトキシエチル）
パーオキシジカーボネート〕及びレドックス触媒〔アル
カリ金属の亜硫酸塩もしくは重亜硫酸塩、亜硫酸アンモ
ニウム、Ｌ−アスコルビン酸、エリソルビン酸などの還
元剤とアルカリ金属の過硫酸塩、過硫酸アンモニウム、
過酸化物などの酸化剤の組合せよりなるもの〕及びこれ
らの２種以上があげられる。Polymerization methods include electron beam or ultraviolet irradiation;
Examples include a heating method and a method using an initiator. In the method using an initiator, the initiator is an azo compound [azobisisobutyronitrile, 2.2'-
Azobis(2,4-dimethylvaleronitrile), azobiscyanovaleric acid, 2,2-azobis(2-amidinopropane) hydrochloride, 2,2-azobis(2-amidinopropane) acetate, etc.], inorganic peroxides Hydrogen oxide, ammonium persulfate, potassium persulfate, sodium persulfate, etc.], organic peroxides [benzoyl peroxide, di-t-butyl peroxide, cumene hydroperoxide, etc.]
0-oxidic acid peroxide, di(2-ethoxyethyl)
peroxydicarbonate] and redox catalyst [reducing agent such as alkali metal sulfite or bisulfite, ammonium sulfite, L-ascorbic acid, erythorbic acid, and alkali metal persulfate, ammonium persulfate,
combinations of oxidizing agents such as peroxides] and two or more of these.
酸を添加するとアミンイミド基は親水性が上がる。従っ
て一般式（１）及び一般式（２）の化合物に酸を加えて
親水性を上げ乳化性を助けることもできる。酸としては
有機または無機の酸たとえば、 塩酸、 リン酸、硫酸
、 硝酸、 蟻酸、 酢酸、 プロピオン酸、乳酸、
（メタ）アクリル酸、蓚酸、クエン酸、マレイン酸、イ
タコン酸、アジピン酸などがあげられる。酸の量はアミ
ンイミド基のモルに対して通常０．３〜１．５倍モルで
ある。酸の添加時期は重合の前でもよいし後でもよいが
、通常重合の前に行う。Addition of acid increases the hydrophilicity of the amine imide group. Therefore, it is also possible to add an acid to the compounds of general formula (1) and general formula (2) to increase their hydrophilicity and assist in their emulsifying properties. Acids include organic or inorganic acids such as hydrochloric acid, phosphoric acid, sulfuric acid, nitric acid, formic acid, acetic acid, propionic acid, lactic acid,
Examples include (meth)acrylic acid, oxalic acid, citric acid, maleic acid, itaconic acid, and adipic acid. The amount of acid is usually 0.3 to 1.5 times the mole of the amine imide group. The acid may be added before or after the polymerization, but it is usually added before the polymerization.
本発明の組成物を製造する方法において、必要に応じて
他の乳化剤、たとえば、アルキル硫酸エステル塩、アル
キルアリールスルホン酸塩、アルキルリン酸エステル塩
あるいは脂肪酸塩などのアニオン界面活性剤、アルキル
アミン塩、アルキル四級アンモニウム塩などのカチオン
界面活性剤、ポリオキシエチレンアルキルアリールエー
テル、ポリオキシエチレンアルキルエーテル、プルロニ
ック型界面活性剤、ソルビタン脂肪酸エステル、ポリオ
キシエチレンソルビタン脂肪酸エステル、ポリエチレン
グリコール脂肪酸エステルなどの非イオン界面活性剤、
カルボン酸塩型（アミノ酸型、ベタイン型など）あるい
はスルホン酸塩型などの両性界面活性剤を併用すること
ができる。これらの乳化剤の使用量は本発明の組成物を
構成する一般式（１）で示されるアミンイミド化合物及
び／または一般式（２）で示されるアミンイミド化合物
の重量の５０％以下が好ましい。In the method for producing the composition of the present invention, other emulsifiers may be used as necessary, such as anionic surfactants such as alkyl sulfate salts, alkylaryl sulfonate salts, alkyl phosphate salts or fatty acid salts, and alkyl amine salts. , cationic surfactants such as alkyl quaternary ammonium salts, polyoxyethylene alkylaryl ethers, polyoxyethylene alkyl ethers, pluronic type surfactants, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyethylene glycol fatty acid esters ionic surfactant,
Ampholytic surfactants such as carboxylate type (amino acid type, betaine type, etc.) or sulfonate type can be used in combination. The amount of these emulsifiers used is preferably 50% or less of the weight of the amine imide compound represented by general formula (1) and/or the amine imide compound represented by general formula (2) constituting the composition of the present invention.
また本発明の組成物を製造する方法において、乳化安定
化の目的で保護コロイド剤、たとえばポリビニルアルコ
ール、カルボキシメチルセルロース、メチルセルロース
、ヒドロキシエチルセルロース、ヒドキシプロピルセル
ロースなどを使用することができるが。保諧コロイド剤
の使用量は本発明の組成物を構成する一般式（１）で示
されるアミンイミド化合物及び／または一般式（２）で
示されるアミンイミド化合物の重量の２０％以下が好ま
しい。In addition, in the method for producing the composition of the present invention, protective colloid agents such as polyvinyl alcohol, carboxymethyl cellulose, methyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, etc. can be used for the purpose of emulsion stabilization. The amount of the protective colloid agent used is preferably 20% or less of the weight of the amine imide compound represented by general formula (1) and/or the amine imide compound represented by general formula (2) constituting the composition of the present invention.
重合方式としては、公知の重合方法により、バッチ式重
合法、連続式重合法のいずれでも可能である。公知の重
合方法としては一括仕込法、単量体添加法、単量体エマ
ルション添加法などがあげられる。The polymerization method may be either a batch polymerization method or a continuous polymerization method using a known polymerization method. Known polymerization methods include a bulk charging method, a monomer addition method, a monomer emulsion addition method, and the like.
重合温度は、重合方法、重合しようとする単量体の種類
、乳化状態などによって異なるが、通常５〜１００℃、
好ましくは１０〜１００℃である。The polymerization temperature varies depending on the polymerization method, the type of monomer to be polymerized, the emulsification state, etc., but is usually 5 to 100°C,
Preferably it is 10-100°C.
本発明の組成物には必要に応じて、消泡剤、粘度調整剤
、造膜助剤、防腐剤、凍結安定剤、架橋剤、可塑剤、粘
着剤、帯電防止剤、顔料、染料などの添加剤を加えても
よい。The composition of the present invention may optionally contain antifoaming agents, viscosity modifiers, film forming aids, preservatives, freeze stabilizers, crosslinking agents, plasticizers, adhesives, antistatic agents, pigments, dyes, etc. Additives may also be added.
本発明の組成物は接着剤、コーティング剤、シ２３
−リング剤などに適し、接着、塗布、電着、含浸などの
方法で、木材、金属、紙、布などのほかにコンクリート
などの無機系物質にも適用できる。The composition of the present invention is suitable as an adhesive, coating agent, sealing agent, etc., and can be applied to wood, metal, paper, cloth, etc., as well as inorganic materials such as concrete, etc., by methods such as adhesion, coating, electrodeposition, and impregnation. It can also be applied to substances.
たとえば「エマルジョン・ラテックスハンドブック」
（昭和５０年３月、大成社発行）第５ｇエマルジョン・
ラテックスの加工（Ｐ、５Ｅｉ５〜Ｐ、９０３）や「入
門・エマルジョンの応用」 （昭和４８年８月、高分子
刊行会発行）第７章接着剤としての応用〜第１２章その
他の利用（Ｐ、６９〜Ｐ、１５７）に記載されているよ
うな用途や使用法に供することができる。For example, "Emulsion Latex Handbook"
(March 1975, published by Taiseisha) No. 5G emulsion
Latex processing (P, 5Ei5-P, 903) and "Introduction/Applications of emulsions" (August 1970, published by Kobunshi Kankai) Chapter 7 Application as adhesive - Chapter 12 Other uses (P , 69-P, 157).
以下実施例により本発明を更に説明するが、本発明はこ
れに限定されるものではない。The present invention will be further explained below with reference to Examples, but the present invention is not limited thereto.
実施例１
撹拌機、滴下ロート、窒素導入管、温度計及び還流冷却
器を備えた反応器にイオン交換水２７０ｇ１アミンイミ
ド化合物（ＡＩ−３） ２０ｇ１ 酢酸３ｇ、 ２
．２アゾビス（２−アミジノプロパン）ハイドロクロラ
イド１ｇを仕込み、窒素置換後、攪拌下に温度７０〜８
０°Ｃでポリシロキサン含有不飽和単量体（Ｓｌ−３、
４
ｎ＝１１）３０ｇ１ スチレン７５ｇ１ アク１ノ
ル酸ｎ−ブチル７５ｇの混合モノマーを滴下ロートより
３時間番とわたり滴下し重合を行い、乳白色の良好な重
合体エマルション（モノマー転換率：９９％以上、固形
分；約４３％）である本発明の組成物を得た。Example 1 In a reactor equipped with a stirrer, a dropping funnel, a nitrogen inlet tube, a thermometer, and a reflux condenser, 270 g of ion-exchanged water, 20 g of amine imide compound (AI-3), 3 g of acetic acid, 2
．． 1 g of 2-azobis(2-amidinopropane) hydrochloride was charged, and after nitrogen substitution, the temperature was increased to 70 to 8 ml with stirring.
Polysiloxane-containing unsaturated monomer (Sl-3,
4 n=11) 30 g 1 Styrene 75 g 1 Ac 1 A mixed monomer mixture of 75 g of n-butyl norate was added dropwise from the dropping funnel over 3 hours to perform polymerization, resulting in a milky white polymer emulsion (monomer conversion rate: 99% or more, A composition of the present invention having a solid content of approximately 43% was obtained.
実施例２
実施例１と同様の装置にイオン交換水２１１１１ｇ、
アミンイミド化合物（ＡＩ−４） １５ｇ１ 酢酸
２．５ｇ１２．２−アゾビス（２−アミジノプロノくン
）ノ＼イドロクロライド０．７５ｇを仕込み、窒素置換
後、撹拌丁番と温度７０〜８０°Ｃでポリシロキサン含
有不飽和単量体（Ｓｌ−３、ｎ＝２４） ３０ ｇ、
メタクリル酸メチル４５ｇ１ アクリル酸ｎ−ブチ
ル４８ｇ１ メタクリル酸２−ヒドロキシエチル１２
ｇの混合モノマーを滴下ロートより３［ｌ各間にわたり
滴下し重合を行い、乳白色の良女子な重合体エマルショ
ン（モノマー転換率； ９９％以上、固形分；約４１．
５％）である本発明の組成物を１＠た。Example 2 21111 g of ion-exchanged water was placed in the same apparatus as in Example 1,
Amine imide compound (AI-4) 15g 1 Acetic acid 2.5g 12. 2-Azobis(2-amidinopronocon)hydrochloride 0.75g was charged, and after nitrogen substitution, the polysiloxane was heated with a stirring hinge and a temperature of 70 to 80°C. Containing unsaturated monomer (Sl-3, n=24) 30 g,
Methyl methacrylate 45g1 n-butyl acrylate 48g1 2-hydroxyethyl methacrylate 12
Polymerization was carried out by dropping 3 liters of mixed monomer from a dropping funnel into a milky white polymer emulsion (monomer conversion rate: 99% or more, solid content: about 41.0 g).
5%) of the composition of the present invention.
実施例３
実施例１と同様の装置にイオン交換水７０ｇ１ アミ
ンイミド化合物（ＡＩ−５） ４．８ｇ１ ボＩＪシ
ロキサン含有不飽和単量体（Ｓｉ３、ｎ＝１１） １２
ｇ、 スチレン１７ｇ１ アクリル酸エチル２１ｇ
１ アクリル酸２−ヒドキシエチル６ｇ１ 乳酸１
ｇ及び２，２−アゾビス（２−アミジノプロパン）ハイ
ドロクロライドｏ、ｅｇを仕込み、攪拌乳化し窒素置換
後７０〜７５°Ｃで３０分間乳化した。引続きイオン交
換水２００ｇ１ アミンイミド化合物（Ａｌ−５）
１１．２ｇ１ ポリシロキサン含有不飽和単量体（Ｓ
１３、ｎ＝１１） ２８ｇ、 スチレン３８ｇ１
アクリル酸エチル４８ｇ１ アクリル酸２−ヒドキシ
エチル１４ｇ１ 乳酸１．５ｇ及び２，２−アゾビス
（２−アミジノプロパン）ハイドロクロライド１．４ｇ
から成る乳化液を窒素雰囲気下７０〜７５°Ｃで滴下ロ
ートより３時間にわたり滴下し重合を行い、乳白色の良
好な重合体エマルション（モノマー転換率；９９％以上
、固形分；約４３％）である本発明の組成物を得た。Example 3 70 g of ion-exchanged water 1 amine imide compound (AI-5) 4.8 g 1 BoIJ siloxane-containing unsaturated monomer (Si3, n=11) 12
g, styrene 17g1 ethyl acrylate 21g
1 2-hydroxyethyl acrylate 6g 1 lactic acid 1
g and 2,2-azobis(2-amidinopropane) hydrochloride o and eg were added, stirred and emulsified, and after purging with nitrogen, emulsification was carried out at 70 to 75°C for 30 minutes. Next, 200 g of ion-exchanged water 1 amine imide compound (Al-5)
11.2g1 polysiloxane-containing unsaturated monomer (S
13, n=11) 28g, styrene 38g1
48 g of ethyl acrylate 14 g of 2-hydroxyethyl acrylate 1.5 g of lactic acid and 1.4 g of 2,2-azobis(2-amidinopropane) hydrochloride
An emulsion consisting of the above was polymerized by dropping it from a dropping funnel at 70 to 75°C in a nitrogen atmosphere for 3 hours, resulting in a milky white polymer emulsion (monomer conversion rate: 99% or more, solid content: about 43%). A composition of the invention was obtained.
実施例４
実施例１と同様の装置にイオン交換水７０ｇ１ アミ
ンイミド化合物（ＡＩ−９） Ｇｇ１ ポリシロキサ
ン含有不飽和単量体（Ｓ１３、ｎ＝Ｅｉ５） Ｂ ｇ、
メタクリル酸メチル２４ｇ１ アクリル酸ｎ−ブ
チル２４ｇ及びアゾビスジアノ吉草酸０．３ｇを仕込み
、撹拌乳化し窒素置換後８０〜３０℃で３０分間重合し
た。引続きイオン交換水２００ｇ、 アミンイミド化
合物（ＡＩ−９） １４ｇ、 ポリシロキサン含有不
飽和車量体（Ｓｔ−３、ｎ＝６５） １４ｇ１ メタ
クリル酸メチル５６ｇ１ アクリル酸ｎ−ブチル５１
４及びアゾビスシアノ吉草酸０．７ｇから成る乳化液を
窒素雰囲気下８０〜９０°Ｃで滴下し重合を行い、乳白
色の良好な重合体エマルション（モノマー転換率；９９
％以」二、固形分；約４３％）である本発明の組成物を
得た。Example 4 Into the same apparatus as in Example 1, 70 g of ion-exchanged water 1 Aminimide compound (AI-9) Gg1 Polysiloxane-containing unsaturated monomer (S13, n=Ei5) B g,
24 g of methyl methacrylate, 24 g of n-butyl acrylate, and 0.3 g of azobis dianovaleric acid were charged, stirred and emulsified, and after purging with nitrogen, polymerization was carried out at 80 to 30° C. for 30 minutes. Next, 200 g of ion-exchanged water, 14 g of amine imide compound (AI-9), 14 g of polysiloxane-containing unsaturated caramer (St-3, n=65), 56 g of methyl methacrylate, 51 n-butyl acrylate.
4 and 0.7 g of azobiscyanovaleric acid was added dropwise at 80 to 90°C under a nitrogen atmosphere to perform polymerization, resulting in a milky white polymer emulsion (monomer conversion rate: 99
A composition of the present invention was obtained having a solid content of approximately 43% or more.
実施例５ 実施例１と同様の装置に、イオン交換水２７０ｇ。Example 5 Into the same apparatus as in Example 1, 270 g of ion-exchanged water was added.
アミンイミド化合物（ＡＩ−１０） １５ｇ、 乳酸
３ｇ及びアゾビスシアノ吉草酸】ｇを仕込み、窒素置換
後、撹拌下に８０〜９０℃で、ポリシロキサン含有不飽
和単量体（Ｓｉ３、ｎ＝１１） １５ｇ１ メタクリ
ル酸メチル１００ｇ、 アクリル酸エチル７０の混合
モノマーを滴下ロートより３時間にわたり滴下し重合を
行い、乳白色の良好な重合体エマルション（モノマー転
換率；９９％以上、濃度；約４３％）である本発明の組
成２７
物を得た。Charge 15 g of amine imide compound (AI-10), 3 g of lactic acid, and 1 g of azobiscyanovaleric acid, and after purging with nitrogen, heat at 80 to 90°C with stirring, 15 g of polysiloxane-containing unsaturated monomer (Si3, n=11) 1 methacrylate A monomer mixture of 100 g of methyl acrylate and 70 g of ethyl acrylate was added dropwise from a dropping funnel over 3 hours to polymerize, resulting in a milky white polymer emulsion (monomer conversion rate: 99% or more, concentration: about 43%). Composition 27 was obtained.
比較例１
実施例１において、アミンイミド化合物の代わりに乳化
剤としてジヘキシルスルホコハク酸ナトリウムを使用し
、実施例１の方法に従って乳化重合を行い、乳白色の重
合体エマルション（モノマー転換率；３９％以上、濃度
；約４３％）を得た。Comparative Example 1 In Example 1, sodium dihexyl sulfosuccinate was used as an emulsifier instead of the amine imide compound, emulsion polymerization was carried out according to the method of Example 1, and a milky white polymer emulsion (monomer conversion rate: 39% or more, concentration; approximately 43%).
試験例１
実施例１〜５の本発明の組成物及び比較例１の組成物に
ついて次の試験を行った。その結果を表〜１に示す。Test Example 1 The following tests were conducted on the compositions of the present invention of Examples 1 to 5 and the composition of Comparative Example 1. The results are shown in Table 1.
（１）貯蔵安定性試験
実施例１〜５及び比較例１から得られた重合体エマルシ
ョン５（Ｉｇをガラス瓶に採り密閉し、−１０’ｃＸｅ
時間、３０’ＣＸｌ１ｉ時間を１＋１−イクルとしてエ
マルションが破壊するまでの回数を測定した。(1) Storage stability test Polymer emulsion 5 (Ig) obtained from Examples 1 to 5 and Comparative Example 1 was placed in a glass bottle, sealed, and -10'cXe
The number of times until the emulsion breaks was measured by setting the time and 30'CXl1i as 1+1-cycles.
（２〉耐水性試験
実施例１〜５及び比較例１から得られた重８
合体エマルションをガラス板に広げ、２０℃にて２４時
間乾燥し、更にｅ ｏ ’ｃにて８時Ｉｉｌ乾燥して０
．２ｍｍの厚さのフィルムを作製した。このフィルムの
耐水性をＪＩＳ−に６８２８の水滴試験法により試験し
た。(2> Water resistance test The polymer 8 polymer emulsion obtained from Examples 1 to 5 and Comparative Example 1 was spread on a glass plate, dried at 20°C for 24 hours, and further dried at 8 o'clock in an e-o'c. Te 0
．． A film with a thickness of 2 mm was produced. The water resistance of this film was tested according to JIS-6828 water drop test method.
（３）撥水性試験
実施例１〜５及び比較例１から得られた重合体エマルシ
ョンをガラス板に広げ、２０℃にて２４時間乾燥し、更
に６ｏ″Ｃにて８時間乾燥して０．２ｍｍの厚さのフィ
ルムを作製した。このフィルムについて水に対する接触
角を測定した。(3) Water repellency test The polymer emulsions obtained from Examples 1 to 5 and Comparative Example 1 were spread on a glass plate, dried at 20° C. for 24 hours, and further dried at 6°C for 8 hours. A film with a thickness of 2 mm was prepared.The contact angle of this film to water was measured.
（表−１）試験結果
〔発明の効果〕
本発明の組成物は、
一般式（１）
％式％
（２）で示されるアミンイミド化合物を乳化剤として使
用するため経口変化により乳化剤がブリードアウトする
ことなく、重合体エマルションの安定性は良好であり、
長期保存、凍結融解性も改善される。(Table-1) Test results [Effects of the invention] Since the composition of the present invention uses an amine imide compound represented by general formula (1) % formula % (2) as an emulsifier, the emulsifier bleeds out due to oral changes. The stability of the polymer emulsion is good.
Long-term storage and freeze-thaw properties are also improved.
本発明の組成物から作製されたフィルムあるいは被覆物
は優れた撥水性、撥油性、平滑性、耐水性、耐溶剤性、
耐候性を示し、また本発明の組成物を１５０ ’Ｃ以上
に加熱すると樹脂中のアミンイミド化合物の熱分解によ
る架橋により作製されたフィルムあるいは被覆物の耐水
性、耐溶剤姓が著しく向上する。Films or coatings made from the composition of the present invention have excellent water repellency, oil repellency, smoothness, water resistance, solvent resistance,
It exhibits weather resistance, and when the composition of the present invention is heated to 150'C or higher, the water resistance and solvent resistance of the film or coating produced by crosslinking by thermal decomposition of the amine imide compound in the resin are significantly improved.
本発明の組成物は水性塗料、接着剤、シーリング剤、紙
加工用、繊維加工用、繊維改質用、フロアポリッシュ用
、土壌侵食防止用、コンクリート、モルタル混和用など
の用途に利用できる。The composition of the present invention can be used for applications such as water-based paints, adhesives, sealants, paper processing, fiber processing, fiber modification, floor polish, soil erosion prevention, and mixing with concrete and mortar.
３１31
Claims (1)
＾３はそれぞれ炭素数１〜１０のアルキル基である。 Ｒ＾４は炭素数３〜２５のアルキル基である。）で示さ
れるアミンイミド化合物及び／または 一般式 ▲数式、化学式、表等があります▼（２） （式中、Ｒ＾１は水素原子またはメチル基、Ｒ＾２、Ｒ
＾３はそれぞれ炭素数１〜１０のアルキル基である。 Ｒ＾５は炭素数４〜２８の飽和もしくは不飽和の脂肪族
炭化水素基、または（置換）フェニル基である。）で示
されるアミンイミド化合物と （ｂ）一般式 ▲数式、化学式、表等があります▼（３） （式中、Ｘはビニル基、（メタ）アクリロキシ基または
アリル基、Ｒ＾６は２価の炭化水素基、Ｒ＾７、Ｒ＾８
、Ｒ＾９は水素原子、炭素数１〜１０のアルキル基また
はフェニル基、ｎ＝１〜１３０である。）で示されるポ
リシロキサン基を含有する不飽和単量体と（ｃ）これら
と共重合可能なエチレン性不飽和単量体 との共重合物からなることを特徴とするポリシロキサン
含有水分散型樹脂組成物。 ２、ポリシロキサン含有水分散型樹脂組成物が（ａ）と
（ｂ）と（ｃ）との乳化重合物からなる請求項１記載の
組成物。 ３、（ａ）と（ｂ）と（ｃ）の使用量が全単量体の合計
重量に基づいて、（ａ）が０．５〜３０％、（ｂ）が１
〜５０％、（ｃ）が２０〜９８．５％である請求項１ま
たは２記載の組成物。[Claims] 1. (a) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (1) (In the formula, R^1 is a hydrogen atom or a methyl group, R^2, R
Each ^3 is an alkyl group having 1 to 10 carbon atoms. R^4 is an alkyl group having 3 to 25 carbon atoms. ) Aminimide compounds and/or general formulas ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (2) (In the formula, R^1 is a hydrogen atom or a methyl group, R^2, R
Each ^3 is an alkyl group having 1 to 10 carbon atoms. R^5 is a saturated or unsaturated aliphatic hydrocarbon group having 4 to 28 carbon atoms, or a (substituted) phenyl group. ) and (b) general formula ▲ Numerical formula, chemical formula, table, etc. ▼ (3) (wherein, X is a vinyl group, (meth)acryloxy group or allyl group, and R^6 is a divalent Hydrocarbon group, R^7, R^8
, R^9 is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or a phenyl group, and n=1 to 130. ) and (c) an ethylenically unsaturated monomer copolymerizable with these unsaturated monomers. Resin composition. 2. The composition according to claim 1, wherein the polysiloxane-containing water-dispersed resin composition comprises an emulsion polymer of (a), (b), and (c). 3. The amounts of (a), (b) and (c) used are 0.5-30% for (a) and 1% for (b) based on the total weight of all monomers.
-50%, and (c) is 20-98.5%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19975789A JP2608785B2 (en) | 1989-07-31 | 1989-07-31 | Water-dispersible resin composition containing polysiloxane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19975789A JP2608785B2 (en) | 1989-07-31 | 1989-07-31 | Water-dispersible resin composition containing polysiloxane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0362810A true JPH0362810A (en) | 1991-03-18 |
| JP2608785B2 JP2608785B2 (en) | 1997-05-14 |
Family
ID=16413121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19975789A Expired - Lifetime JP2608785B2 (en) | 1989-07-31 | 1989-07-31 | Water-dispersible resin composition containing polysiloxane |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2608785B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05310857A (en) * | 1992-05-05 | 1993-11-22 | Showa Highpolymer Co Ltd | Water-based coating agent for water repellency treatment |
| WO1995009203A1 (en) * | 1993-09-27 | 1995-04-06 | Sanyo Chemical Industries, Ltd. | Aqueous dispersion of polymer composition |
| US5480634A (en) * | 1989-07-12 | 1996-01-02 | Mitsubishi Chemical Corporation | Hair-care products containing copolymers formed from unsaturated hydrophilic monomers and unsaturated monomers having a polysiloxane group |
| JP2002275203A (en) * | 2001-03-22 | 2002-09-25 | Chuo Rika Kogyo Corp | Acrylic polymer emulsion and method for producing the same |
-
1989
- 1989-07-31 JP JP19975789A patent/JP2608785B2/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5480634A (en) * | 1989-07-12 | 1996-01-02 | Mitsubishi Chemical Corporation | Hair-care products containing copolymers formed from unsaturated hydrophilic monomers and unsaturated monomers having a polysiloxane group |
| JPH05310857A (en) * | 1992-05-05 | 1993-11-22 | Showa Highpolymer Co Ltd | Water-based coating agent for water repellency treatment |
| WO1995009203A1 (en) * | 1993-09-27 | 1995-04-06 | Sanyo Chemical Industries, Ltd. | Aqueous dispersion of polymer composition |
| JP2002275203A (en) * | 2001-03-22 | 2002-09-25 | Chuo Rika Kogyo Corp | Acrylic polymer emulsion and method for producing the same |
| JP4508449B2 (en) * | 2001-03-22 | 2010-07-21 | 中央理化工業株式会社 | Acrylic polymer emulsion and method for producing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2608785B2 (en) | 1997-05-14 |
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