GB2260764A - Stabilizing composition for polymers - Google Patents
Stabilizing composition for polymers Download PDFInfo
- Publication number
- GB2260764A GB2260764A GB9221154A GB9221154A GB2260764A GB 2260764 A GB2260764 A GB 2260764A GB 9221154 A GB9221154 A GB 9221154A GB 9221154 A GB9221154 A GB 9221154A GB 2260764 A GB2260764 A GB 2260764A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- alkyl
- phenyl
- case
- composition according
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 46
- 229920000642 polymer Polymers 0.000 title claims abstract description 25
- 230000000087 stabilizing effect Effects 0.000 title claims abstract description 24
- -1 polysiloxane Polymers 0.000 claims abstract description 35
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 239000004611 light stabiliser Substances 0.000 claims abstract description 16
- 150000001412 amines Chemical class 0.000 claims abstract description 9
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical class C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 claims abstract description 5
- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 150000002431 hydrogen Chemical group 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 abstract description 9
- 229920002635 polyurethane Polymers 0.000 abstract description 8
- 239000004814 polyurethane Substances 0.000 abstract description 8
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 abstract 2
- 229940087168 alpha tocopherol Drugs 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 229960000984 tocofersolan Drugs 0.000 abstract 1
- 239000002076 α-tocopherol Substances 0.000 abstract 1
- 235000004835 α-tocopherol Nutrition 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 description 32
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 16
- 239000000654 additive Substances 0.000 description 11
- 239000004743 Polypropylene Substances 0.000 description 9
- 230000000996 additive effect Effects 0.000 description 9
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 7
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 6
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 6
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- 229920002803 thermoplastic polyurethane Polymers 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
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- 239000004698 Polyethylene Substances 0.000 description 4
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- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 239000002612 dispersion medium Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 229920006324 polyoxymethylene Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 101100378709 Arabidopsis thaliana AIR3 gene Proteins 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004709 Chlorinated polyethylene Substances 0.000 description 2
- RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 229920000092 linear low density polyethylene Polymers 0.000 description 2
- 239000004707 linear low-density polyethylene Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229940102838 methylmethacrylate Drugs 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 229920001748 polybutylene Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229960001295 tocopherol Drugs 0.000 description 2
- 239000011732 tocopherol Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical class CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-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
- PZRWFKGUFWPFID-UHFFFAOYSA-N 3,9-dioctadecoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCCCCCCCCCCCC)OCC21COP(OCCCCCCCCCCCCCCCCCC)OC2 PZRWFKGUFWPFID-UHFFFAOYSA-N 0.000 description 1
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 1
- ZVNPWFOVUDMGRP-UHFFFAOYSA-N 4-methylaminophenol sulfate Chemical compound OS(O)(=O)=O.CNC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1 ZVNPWFOVUDMGRP-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229920004939 Cariflex™ Polymers 0.000 description 1
- DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 239000004801 Chlorinated PVC Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
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- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
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- 150000002576 ketones Chemical class 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- PGYPOBZJRVSMDS-UHFFFAOYSA-N loperamide hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)N(C)C)CCN(CC1)CCC1(O)C1=CC=C(Cl)C=C1 PGYPOBZJRVSMDS-UHFFFAOYSA-N 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 150000002681 magnesium compounds Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920001179 medium density polyethylene Polymers 0.000 description 1
- 239000004701 medium-density polyethylene Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 150000002739 metals Chemical class 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
- 239000000178 monomer Substances 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 229940065472 octyl acrylate Drugs 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000002899 organoaluminium compounds Chemical class 0.000 description 1
- 150000002901 organomagnesium compounds Chemical class 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 1
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000582 polyisocyanurate Polymers 0.000 description 1
- 239000011495 polyisocyanurate Substances 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003336 secondary aromatic amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1545—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/20—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
- C08K5/353—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
A stabilizing composition useful as a processing and light stabilizer for polymers such as polyurethane and polyolefins comprises a) a mono- or di- phosphite or mono- or diphosphonite b) a chroman derivative (especially alpha -tocopherol or derivatives thereof); and c) a light stabilizer (component c) selected from (i) a polymer containing at least one hindered amine light stabilizer group, preferably a polysiloxane containing a hindered amine light stabilizer group and/or ii) the combination of an oxanilide and a hindered amino light stabilizer (HALS) compound.
Description
- 3 ') 1 COMPOSITIONS FOR STABILIZING POLYMERS The invention relates to
new compositions for stabilizing polymers, for example, polyurethane.
According to the invention, there is provided a stabilizing composition, useful as a processing and light stabilizer for polymers such as polyurethane comprising:
a) a mono- or di- phosphite or mono- or diphosphonite (component a) b) a chroman derivative (especially cc-tocopherol or derivatives thereof) (component b); and a light stabilizer (component c) selected from i) a polymer containing at least one hindered amine light stabilizer group, preferably polysiloxane containing a hindered amine light stabilizer group (component i) and/or ii) the combination of an oxanilide and a hindered amine light stabilizer (HALS) compound (component ii).
Preferred mono- and di- phosphites for use in a composition according to the invention are those of formula I or 11 /0- R, IR,-0-P O-Rl 0- (H2 CHi-- 0 1 R,- 0- "C P-O-Rl 1 0- CH2 CHi--d (1) (11) 2 Case 153-5550 in which each R, independently is a group derived from an aliphatic, alicyclic or aromatic alcohol containing one or two OH groups.
Aromatic alcohol, in the Specification, include phenols.
Preferred mono- or diphosphonites are selected from compounds of formula III RIP RIO- 0- p R16-0 in which m is 0 or 1; n is 0 or 1; p is 0 or 1; / 0-% ,, P,, 0-% m each R., independently, is a group derived from an aliphatic, alicyclic or aromatic alcohol containing one or two OH groups; whereby the two -OH groups are not positioned to be able to form a P-containing ring; (hereinafter defined as the monovalent significances of Rq); or both groups R. form a group derived from an aliphatic, alicyclic or aromatic alcohol containing two OH groups in such a position that they can form a cyclic group with a single phosphorus atom (hereinafter defined as the divalent significances of Rq):
IR,, is a monovalent or divalent significance of IR,; Y is -0-, -S-, CH(Rj- or -CH4-; where R3 is hydrogen, Cl_.alkyl or COOR4and R4 'SC1_. alkyl. More preferably the mono- 11 3 Case 153-5550 and diphosphonites are diphosphonites, most preferably tetrakis (2,4-tert. butyl phenyl) biphenylene diphosphonite (commercially available as SANDOSTAB P-EPO from SANDOZ Chemicals Ltd.).
Preferably R, is R,' where R,' is a linear or branchedCl-22alkyl or phenyl, unsubstituted or substituted by 1 to 3 linear or branched Cl12alkyl groups (such substitution when present, preferably being Cl4alkyl).
Preferably R. is R3'where R.' is hydrogen or methyl.
Preferably R4 is R4'where R4' 'S Cl-4alky].
Preferred phosphites of component a) are selected from tris(2,4-di-t. butyl phenyl)phosphite, tris(nonylphenyi)phosphite, di- isodecylphenyl phosphite, tril au ryl phosphite, bis (2,6-di-t.butyl-4methyiphenyi)pentaerythrityi diphosphite, bis (2,4-di-t.butyl phenyl)pentaerythrityl diphosphite and distearylpentaerythrityl diphosphite.
Preferred chroman derivatives are of those of formula IV CH3 33 0:k CM131 CH3 CH3 (IV) in which R2 is -(CH2)3-CH-(CH2)3-CH-(CH2)3-CH-CH3 1 1 1 u13 CH3 jn3 or -CH2-CH2-0-CO-R, where R. is selected from C7-30alkyl, -CH2CH2"S- (C130aikyi) or 4 C(CH3)3 -CH2 -C OH C((H3 Preferred polysiloxanes are compounds of formula V 91 -6alkyl fH2)2-8 0 H CH3 CH3 CH3 3R Case 153-5550 (V) in which na--- 1 to 100, preferably 5 to 30. R is selected from hydrogen, C,_.alkyl, oxygen,-OR, or -CO-R5where R5 is -C(R8)=CH2, C,_.alkyl, phenyl, -COCA, -CH2C.H., -COOC1-12alkyl, COOH, or NR7R8, where R7 is hydrogen, Cl-12alkyl, C,_,cycloalkyl, phenyl, pheny1C1-4alkyl or Cl-12alkylphenyl and R8 'S Cl-12alkyl or hydrogen.
Preferred oxanilides are those of formula V11 (R1 J2 (R1 A N-COM E) R13 R 13 R, 1 13 R,, (V11) Case 153-5550 in which each R,, independently is selected from hydrogen, C,_1.alkyl, C, _1.alkoxy, halogen, hydroxy, phenyl and phenoxy; and each R,., independently, is selected from hydrogen, halogen, hydroxy, C,-. alkyl and C,-.alkoxy; and each R13, independently, is hydrogen or methyl.
Preferably R,, is R,,' where R,,' is selected from hydrogen, hydroxy, Cl4alkyl and Cl-4alkoxy, more preferably R,, is hydrogen.
Preferably R,. is R,,' where R12' is selected from hydrogen, hydroxy, Cl4alkyl and Cl-4alkoxy, more preferably on phenyl group A and B, one R12 is hydrogen and the other R12 is R12"where R,." 'S Cl-4alkyl orCl-4aikoxy. Preferably R12" on ring A is a Cl-4alkyl and on ring B R12" is aCl4alkoxy.
Preferably R13 is hydrogen.
Preferably both R12 groups are ortho to one another.
Preferred HALS compounds are 2,2,6,6-tetramethylpiperidine compounds. More preferred HALS compounds are those of formula V1 (H3 CH3 R N Rio >, R15 CH3 CH 3 V1 6 Case 153-5550 in which R is selected from hydrogen, C,_.alkyl, oxygen or -COR.; where R. is C(RJ=CH2, C,,alkyl, phenyl, -NR7R,, -CO-C6H., -CH2C6H,, -CO0C1- 12alkyl or -COOH; where R7 is hydrogen, Cl-12alky], C5-6C0oalkyl (preferably cyclohexyl), phenyl, phenyl Cl-4alkyl orCl-12alkylphenyl and R. is hydrogen orCl-12alky]; R,5 is hydrogen, Cl-22alkyl, C,-22alkoxy, - N(RJ-CO-CO-R2.; or -NH-C(R3)=N-R21; R3 is hydrogen, Cl-1.alkyl or COOR4where R4 'SC1-,,alkyl R2. is an amide forming group and R21 is Cl-1. alkyl, phenyl, unsubstituted or substituted by 1 to 3 groups selected fromCl-,8a]ky], Cl-4alkoxy and halogen; or IR,. is CH3 CH R18 N-R (CH2)8-1 -0 12 CH3 CH3 and IR,. is hydrogen or Cl,,alkyl; or IR,. and R16together with the C-atom to which they are attached, form a group of formula a) \ C,, ('- (CH2)11 O-C_.', CO- N 2-4alkylene4X)OC1-22alkyl -C (a) Preferably R is R'where R' is hydrogen, C,_4alkyl or -COR.' where R5' 'S Cl-4alkyl or - CO0C1-4alkyl, more preferably R' where R' is hydrogen, methyl or -COCH..
7 Case 153-5550 More preferred 2,2,6,6-tet ram ethyl pipe ri di nyl compounds are of formula W CH3 CH3 ( (CH2)11 0- & W- N 1 _1 CoN-CH2CH200C-laalkyl (M3 CH.9 (V]') where R' is hydrogen, Cl-4alkyl or -CO-R5' where R,,' 'S Cl-4alkyl or -CO- OC1-4alkyl.
Preferably the ratio of components a) and b) to c) is 3:1 to 12, more preferably 1A.
Preferably the ratio of component a) to component b) is 6:1 to 12, more preferaoly 4A.
10:1 to 12, more preferably Preferably in compositions according to the invention the amounts of components a) to c) are as follows:
30-50% (preferably 40%) component a) 5-20% (preferably 10%) component b) aAl 30-65% (preferably 50%) component c).
If more than one light stabilizer is present in component c) they are preferably an oxanilide and a HALS compound. Preferably the ratio of oxanilide to HALS compound is 3:1 to 12, preferably 2A.
Preferably the compositions according to the invention are in the form of liquid preparations, preferably without plasticizer or solvent.
8 Case 153-5550 According to the invention there is further provided a polymeric composition comprising a polymeric material and a stabilizing amount (preferably 0.2-8% based on the weight of polymeric material) of a stabilizing composition defined above.
Polymeric materials that can be stabilized by a stabilizing composition according to the invention include homopolymers, copolymers and polymer blends of:
Cellulose acetate; Cellulose acetobutyrate; Cellulose acetopropionate; Cresolformaldehyde resin; Carboxymethy1cellulose; Cellulose nitrate; Cellulose propionate; Casein plastics; Casein-formalclehyde; Cellulose triacetate; Ethyl cellulose; Epoxy resins; Methyl cellulose; Melamineformaldehyde resins; Polyamide; Polyamideimide; Polyacrylonitrile; Polybutene-1 and -2; Polybutylacrylate; Poly-(butyleneterephthalate); Polycarbonate; Poly(chlorotrifluoroethylene); Poly(diallylphthalate); Polyethylene; chlorinated Polyethylene; Poly(etherketone); Polyetherimide; Polyethyleneoxide; Polyethersulphone; Poly(ethyleneterephthalate); Polytetrafluoroethylene; Phenolformaldehyde resins; Polyimide; Polyisobutylene; Polyisocyanu rate; Polymethacrylimide; Polymethylmethacrylate; Poly(4-methylpentene-1); Poly(a-methyl styrene); Polyoxymethylene; Polyformaldehyde; Polyacetal; Poly- propylene; Polyphenylene ether; Polyphenylenesulphide; Polyphe nyl ene-sul phone; Polystyrene; Polysulphone; Polyurethane; Polyvinyl acetate; Polyvinyl alcohol; Polyvinylbutyral; chlorinated Polyvinyl chloride; Polyvinylidene chloride; Polyvinylidene fluoride; Polyviny[fluodde; Polyvinylformalclehyde; Polyvinylformalclehyde; Polyvinylcarbazol; Polyvinylpyrroliclone; Silicon polymers; saturated polyester; ureaformaldehyde resins; unsaturated polyester; polyacrylate; polymethacrylate; polyacrylamide; maleinate resins; phenolic resins; aniline resins; furane resins; carbamide resins; epoxide resins and silicon resins.
Examples of suitable copolymers include:
9 Case 153-5550 Acrylon itril e/butadien e/acryl ate; Acrylonitrile/butadiene/styrene; Acrylonitrile/methylmeth- acrylate; Acrylonitrile/styrene/acrylic ester; Acrylonitrile/ethylenepropylenediene/styrene; Acrylonitrile/ chlorinated polyethylene/styrene; Ethylene/ethylacrylate; Ethylenemethacrylic acid ester; Ethylene/propylene; Ethylene/propylene-diene; Ethylenelvinyl acetate; Ethylene/vinyl alcohol; Ethylene/tetrafluoro-ethylene; Tetrafluoroethylene/ hexafluoropropylene; Methacrylate /butadiene/styrene; Melamine/phenol-formaidehyde; Polyester blockamide; Perfluoro-alkoxyalkane; Styrene/acrylonitrile; Styrene/butadiene; Styrene/ maleic acid anhydride; Styrene/a-methylstyrene; Vinylchloride/ethylene; Vinylchloride/ ethylene/methacrylate; Vinylchloride/ethylenelvinyl acetate; Vinylchloridel methyl-methacrylate; Vinylchloride/octylacrylate; Vinylchloride/vinyl acetate; and Vinylchloride/ vinylidene chloride.
Preferred polymeric materials that can be stabilized are polyolefins such as polypropylene, polyethylene (e.g. high density polyethylene, low density polyethylene, linear low density polyethylene or medium density polyethylene), polybutylene, poly-4-methylpentene and copolymers thereof and polyurethane.
Preferred polyurethanes are those prepared from isocyanate resins and polyols. Preferred isocyanates are those commercially available as Desmodur, Elastan, Lupranat, Tedimon, Scuranat, Suprasec, Systanat, Hylene, lsonate (-Papi), Multrathane, Nacconate and Sumidur.
Preferred Polyols are those commericially available as Desmophen, Lupranol, Lupraphen, Glendion, Napiol, Scuranol, Caradol, Daltolac, Daltorez, Diorez, Estolan, Propylan, Armol, Bermodol, lsonol, Metpol, Multron, Multranol, Niax Polyol, Pluracol, Quadrol, Thanol, Voranol and Sumiphen.
Case 153-5550 Such polyurethanes are as describes in Saechtling: Kunststoff Taschenbuch 23 Ausgabe - published by Carl Hansen Verlag 1986 (esp. p. 339-410). The contents of this book are incorporated herein by reference.
Further additives that can be added to a stabilizing or a polymeric composition according to the invention include antioxidants, such as sterically hindered phenols, secondary aromatic amines or thioethers, such as described in "Kunststoff-Additive" - Gachter /M0fler, Ed. 3, 1990 p.42-50, the contents of which are incorporated herein by reference; U.V. stabilizers such as sterically hindered amines (for example Nunsubstituted, Walkyl or N-acyl substituted 2,2,6,6-tetra methyl pipe ridi n e compounds) [also known as hindered amine light stabilizers - HALS] and U.V. absorbers (e.g. 2-(2'-hydroxyphenyi) -benztriazoles, 2hydroxybenzophenones, 1,3-bis-(2'-hydroxybenzoyi-) benzene saiicylates, cinnamates and oxalic acid diamides;), U.V. quenchers such as benzoates and substituted benzoates, antistatic agents, flameproofing agents, softeners, nucleating agents, metal deactivators, biocides, impact modifiers, fillers, pigments and fungicides.
Stabilizing compositions according to the invention may be added to the polymeric material before, during or after the polymerization step and may be added in solid or molten form, in solution preferably as a liquid concentrate containing from 10 to 80 % by weight of the composition and 90 to 20 % by weight of solvent or as a solid masterbatch composition containing 10 to 80 % (more preferably 40 to 70 %) by weight of the composition and 90 to 20 % (more preferably 60 to 30 %) by weight of a solid polymeric material which is identical with or compatible with the material to be stabilized.
The stabilizing compositions according to the invention may be incorporated by known methods into the polymeric material to be stabilized. Of particular importance is dry-blending of the compositions according to the invention with the polymer or coating Case 153-5550 shaped polymer particles, e.g. polymer spheres, with the present compositions in the form of a liquid, a solution or a suspension/dispersion. Of particular importance is blending of the compounds with thermoplastic polymers in the melt, for example in a melt blender or during the formation of shaped articles, including films, tubes, fibres and foams by extrusion, injection moulding, blow moulding, spinning or wire coating. The compositions according to the invention are particularly useful for polypropylene and polyethylene articles of every type and polyurethane.
Further, in this specification, where a range is given, the figures defining the range are included therein. Any group capable of being linear or branched is linear or branched unless indicated to the contrary.
For the avoidance of doubt, in this specification t-butyl means tertiary butyl, (-C(CHI).
The new stabilizer compositions are especially suitable for use in polyolefins and especially a- polyolefins prepared using processing catalysts known as Generation 11 to Generation V catalysts and which have not been subjected to a catalyst removal step. By the term "catalyst removal step" used herein is meant a step for the purpose of positively removing the catalyst residues contained in the polymerized polyolefins or treating the polyolefins with the compound which can react with the catalyst residue and inactivate or solubilize the residue, such as alcohols or water, and then removing the inactivated or solubilized catalyst residue by physical means such as filtration, washing and centrifuging. Thus, in the case of suspension polymerization, the step of separating the resulting polymer from a dispersion medium, such as a solvent or a liquefied monomer, does not fall under the above-mentioned definition of the catalyst residue removal step, although the catalyst dissolved in the dispersion medium may be removed by a separation step. The step of adding a small amount of catalyst poisons such as ethers, alcohols, ketones, esters and water to the resulting polymer, to inactivate the catalyst remaining after the 12 Case 153-5550 completion of polymerization, or the step of treating the resulting polymer suspension with gas such as steam or nitrogen to remove the dispersion medium also does not fall under the above-mentioned definition of the "catalyst residue-removal" step.
What we mean by Generation 1 catalysts are titanium halide catalysts and an organo aluminium compound or an organo aluminium halide.
What we mean by Generation 11 catalysts are Generation 1 catalysts supported on an organo magnesium compound or based on an organo chromium compound supported onSA.
What we mean by a Generation III catalyst is a Ziegler type complex catalyst supported on a halogen containing magnesium compound.
What we mean by a Generation IV catalyst is a Generation III catalyst with a silane donor.
What we mean by Generation V catalysts is a bis-indenyl organo titanium compound supported on alumoxane or bis cyclopentadienyl titanium halides activated by aluminium alkyl compound.
Further generations of highly specific catalysts, especially useful for manufacturing highly stereoregular poly-a-olefins, which are presently underdevelopment, belong in the sense of the present invention also to the aforementioned generations of supported catalyst systems. Examples for the microstructure of such highly stereoregular polyolefins are given by syndiotactic polypropylene, isotactic stereoblock polymers, isotactic polypropylene containing stearic defects randomly distributed along the polymer chain (so called anisotactic polypropylene) or stereoirregular steroblock polymers. Due to the 13 Case 153-5550 rapid progress in the development of newer generation catalyst systems the commercial significance of these polymers with novel, highly interesting properties increases more and more. However, residues of such further catalyst generations, as long as they contain metals of the 3d, 4d and 5d series of the periodic system supported analogously to the earlier catalyst generations, can also cause disadvantageous properties in the polymer, as long as such residues are still present in the polymer even if in a deactivated form. Due to this, it can therefore be expected that the new compositions according to the invention are also suitable for overcoming such disadvantageous properties of the polymer. This means that any disadvantageous interaction between processing stabilizers and the aforementioned residues of catalysts of further generations, particularly the hydrolysis of phosphites and phosphonites, is most effectively inhibited.
These generations of catalysts are described in the Twelfth Annual International Conference on Advances in the stabilization and Controlled Degradation of Polymers held in Luzern, Switzerland, 21-23 May 1990 in an article on pages 181 to 196 inclusive by Rolf M01haupt entitled "New Trends in Polyolefin Catalysts and Influence on Polymer Stability". The contents of this article is incorporated herein by reference and especially Table I on page 184 describing the Generation of Catalysts:
14 Case 153-5550 TABLE 1 Polyolefin Catalyst Evolution Generation Example Cat.Act. % Act.Ti Stereoreg. Process Technology (gPP/gTi h atm) (%hept.ins.) 1. TiCI4/AIR, 40 0.01 45% removal of cat.residues and atactic PP TiCl./AIEt2Cl 30 0.1 92% removal of catalyst residues 11 Mg(OEtJITO4/AIR, 40000 50% no removal of cat.residues.
S'02/CP2Cr 40000 HDPE (mainly H13PE/LI-13PE) Ill Mod.MC13cat. 5000 1 95% no purification MgC1J04/AIR3 20000 10 92% + ester donor IV MgC12/TiCI4/AIR3 40000 18 99% no purification + silane donor no extrusion V Bis-indeny]-TiR, on 40000 100 99% novel PPs, narrow MWID (AICH30)2 in which R is an organo group; HDPE is high density polyethylene, LLDPE is linear low density polyethyene, Cp is cyclopentadienyl, Et is ethyl, PP is polypropylene, MWID is molecular weight distribution and x is an integer above 2.
Case 153-5550 Polymeric compositions according to the invention have both good stabilizing properties and good light fastness properties.
The invention will be illustrated by the following Example.
16 Example
Samples preparation Ground formulation:
parts by weight parts by weight Case 153-5550 thermoplastic polyurethane (TPU) granules ("Pellethane 2355-65W from Dow Chemical, USA) Additive and "CarrieC' parts of Additive being light stabilizing compounds 1 or 11 or non-light stabilizing additives A and B being liquid, are previously incorporated in a solid and opaque system (the so-called "CarrieC) consisting of:
37.0 parts by weight SBS granules ("Cariflex TR1 102" from Shell Chemical, U.K.) 19.5 parts by weight LIDPE powder MFI:70 from Verplast, Italy -24.7 parts by weight PE WAX 520 from BASF, Germany &-ak 8.8 parts by weight an antiblocking agent Silica compound ("Syloblock 44" from Grace, USA) 100.0 parts by weight Note: The Tarrier" enables TPU to be used to mould opaque sporting shoe soles.
Preparation:
g of the above blend (of the carder and additive) are homogeneously processed on a two-roll laboratory open mill (Meccaniche Moderne, Italy) at 1 1TA 15C for about 5-7 17 minutes.
Case 153-5550 The resulting rough crepe (2-3 mm thick) is hand-cut by scissors in very small irregular pieces and added to 900 g of TPU granules in a laboratory tumbler and tumbled for about 5 minutes.
This mixture is then fed to the hopper of a "Negri & Bossi V5-8FA" (Italy) laboratory injection moulding machine. Operating at a temperature of 200-220C (cold mould) 1.5 mm thick specimens are moulded for the subsequent accelerated light degradation exposure.
Light exposure The above specimens are exposed in an Atlas Weather-0-MeterWRCi 65, cam 7(LISA) (Black panel 63'C; 50% R.H., according to ASTM D 2565), for 20-70- 162 hours and visually examined for comparative yellowing discoloration and classified by the Vool Blue Scale" (ranking from 8, the best (no discoloration) to 1, the worst (total discoloration)):
Carrier + Additive After 20 h After 70 h After 162 h 6 4 4 6 5 4 A 5 3 2 B 5 3 2 Additive used:
18 Additive 1 is a) 50% of a composition comprising 57% of the compound QNI+CO-CONH-C2H2E OG2H5 29% of (CHX) \k, r CHP" CH2 C-0 CH3 CH3 CH CH3 3 H where R is nCl2H25and n-C14H2. (Composition A); and 14% xylene and Case 153-5550 b) 5 0% of a composition comprising 80% trilaurylphosphite and 20% a- tocopherol (Composition B).
Additive 11 is a composition comprising a) 50% of Composition B and b) 50% of po lym ethyl propyl 3-oxy [4(2,2,6,6-tetramet hyl) pipe ridi nyll siloxane, a compound of the formula 19 PH2 H cCH3 CR3 CH3 RI CH3 where na is a number from 1 to 30.
Additive A is TPU alone ("Pellethane 2355-65D") from Dow Chemical, USA.
Additive B is 90% TPU + 10% Carrier.
Case 153-5550
Claims (12)
1.
Case 153-5550 A stabilizing composition comprising:
a) a mono- or di- phosphite or mono- or diphosphonite (component a) b) a chroman derivative (component b); and c) a light stabilizer (component c) selected from i) a polymer containing at least one hindered amine light stabilizer group (component i) and/or ii) the combination of an oxanilide and a hindered amine light stabilizer (HALS) compound (component ii).
2. A stabilizing composition according to Claim 1 in which the mono- or di- phosphites are of formula I or 11 0-131 RI-0-P, O-R, 0- CH2 CH,--- 0 1 % R,- 0- P C P- 0- IR, 1 CHi----d ()- CH2 (1) (11) in which each R, independently is a group derived from an aliphatic, alicyclic or aromatic alcohol containing one or two OH groups.
3. A stabilizing compositions according to Claim 1 in which the mono- or diphosphonites are selected from compounds of formula III 21 Case 153-5550 R10- 0- p Rje-0 in which m is 0 or 1; n is 0 or 1; p is 0 or 1; P-1%,,, P, 0-% m each Rq, independently, is a group derived from an aliphatic, alicyclic or aromatic alcohol containing one or two OH groups; whereby the two -OH groups are not positioned to be able to form a P-containing ring; (hereinafter defined as the monovalent significances of Rq); or both groups R. form a group derived from an aliphatic, alicyclic or aromatic alcohol containing two OH groups in such a position that they can form a cyclic group with a single phosphorus atom (hereinafter defined as the divalent significances of R,):
R,. is a monovalent or divalent significance of IR,; Y is -0-, -S-, -CH(R3)- or C^-', where R3 is hydrogen or Cl_.alkyl or COOR4and R4 'SC1_.alky].
4. A stabilizing composition according to any one of the preceding claims in which the chroman derivatives are selected from compounds of formula IV 22 Case 153-5550 C'H3 HO R2 a13 C113 CH, (IV) in which R2 is -(CH2)3-CH-(CH2)3-CH-(CH2)3-CH-CH3 1 CH3 CH3 CH3 or -CH 2-CH2-0-CO-R6where R6 'Sselected from C7-30alky], -CH2CH2-S-(C1- 30alkyi) or C(CH3 -CH2-0OH C(CH3b
5. A stabilizing composition according to any one of the preceding claims in which the polysiloxanes are selected from compounds of formula V 23 Case 153-5550 9, -,aikyi 1 4 ? 0.)% fH2)2 - 8 0 H CH3 CH3 K' "' CH3 CH3 RI (V) in which na 1 to 100, R is selected from hydrogen, Cl_.alkyl, oxygen -CO- R5 or OR,, where R. is -C(RJ=CH2, Cl_.alkyl, phenyl, -COCK, -CH2C66H.. - CO0C1-12alkyl, COOH or NR7R,3, where R7 is hydrogen, Cl-12alky], C5-6C0o aikyl, phenyl, phenyl Cl-4alkyl or Cl-12alkylphenyl and R. is Cl-12alkyl or hydrogen.
6. A stabilizing composition according to any one of the preceding claims in which the oxanilides are of formula V11 /& N- CO 00 1 B R R13 1 R,, R13 R, 1 (R1 A (V11) in which each R,, independently is selected from hydrogen, Cl-1.alkyl, Cl- 18alkoxy, halogen, hydroxy, phenyl and phenoxy; and 24 Case 153-5550 each R12, independently, is selected from hydrogen, halogen, hydroxy, Cl,, alkyl and Cl_.alkoxy; and each R13, independently, is hydrogen or methyl.
7. A stabilizing composition according to Claim 6 in which R,, is R,,' where R,,' is selected from hydrogen, hydroxy, C,-4alkyl andCl-4alkoxy; R12is R12' where R12' is selected from hydrogen, hydroxy, Cl-4alkyl andCl4alkoxy; and R,. is hydrogen.
8. A stabilizing composition according to any one of the preceding claims in which the HALS compoound is of formula V1 CH3 CH3 R N R18 R15 CH3 (H (V1) in which R is selected from hydrogen, Cl_.alkyl, oxygen, -COR5 or OR,; where R5 is C(RJ=CH2, Cl_.alkyl, phenyl, -NRA, -CO-C61-15, -CH2C61-15, - CO0C1-1.alkyi or -COOH; where R7 is hydrogen, Cl-12alkyl, Q,-6cycloalkyl phenyl, phenyl Cl-4alkyl or Cl-12alkylphenyl and R8 is hydrogen orCl-12alkyl; R15 is hydrogen, Cl-22alky], Cl-22alkoxy, -N(R),5-CO-CO-R20; or - NWC(R)5=WR21; Case 153-5550 R3 is hydrogen, Cl-1.alkyl or -COOR4where R4 'SC1_.alkyl R20 is an amide forming group and R21 is Cl-1.alky], phenyl, unsubstituted or substituted by 1 to 3 groups selected from Cl-1.alkyl, Cl,aRoxy and halogen; or R,. is (M CH3 RIO W- R "C()0"(CH2)8'12 CO.0 CM3 CH3 R16 is hydrogen or Cl_.alkyl; or JR,. and R16 together with the C-atom to which they are attached, form a group of formula a) r (CH2)11 O-C./ ce.. 1 / \ CO- N-C2-4a1Wene-(X)OC,-22alky It
9. A stabilizing composition substantially as herein described with reference to the Example.
10. A polymeric composition comprising a polymeric material and a stabilizing amount of a composition according to any one of the preceding claims.
11. A polymeric composition comprising 0.2-8% of a stabilizing composition according to any one of Claims 1 to 9.
26 Case 153-5550
12. A polymeric composition substantially as herein described with reference to the Example.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB919121575A GB9121575D0 (en) | 1991-10-11 | 1991-10-11 | Improvements in or relating to organic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB9221154D0 GB9221154D0 (en) | 1992-11-25 |
| GB2260764A true GB2260764A (en) | 1993-04-28 |
Family
ID=10702749
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB919121575A Pending GB9121575D0 (en) | 1991-10-11 | 1991-10-11 | Improvements in or relating to organic compounds |
| GB9221154A Withdrawn GB2260764A (en) | 1991-10-11 | 1992-10-08 | Stabilizing composition for polymers |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB919121575A Pending GB9121575D0 (en) | 1991-10-11 | 1991-10-11 | Improvements in or relating to organic compounds |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPH05214254A (en) |
| DE (1) | DE4233973A1 (en) |
| FR (1) | FR2682392A1 (en) |
| GB (2) | GB9121575D0 (en) |
| IT (1) | IT1263005B (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2278362A (en) * | 1993-05-24 | 1994-11-30 | Sandoz Ltd | Processing stabiliser compositions |
| GB2283490A (en) * | 1993-11-03 | 1995-05-10 | Sandoz Ltd | Processing stabilizers for polymers |
| WO1996017886A1 (en) * | 1994-12-06 | 1996-06-13 | Basf Aktiengesellschaft | Stabilized styrene/butadiene block copolymers |
| GB2263280B (en) * | 1992-01-17 | 1996-07-31 | Sandoz Ltd | Use of a phosphonite and optionally a phosphite for clarifying propylene polymers |
| EP0781805A1 (en) * | 1995-12-29 | 1997-07-02 | General Electric Company | Stabilized thermoplastic polymer composition |
| EP0805178A1 (en) * | 1996-05-03 | 1997-11-05 | Ciba SC Holding AG | Tocopherol-containing composition as stabiliser for thermoplastic materials |
| US5695689A (en) * | 1994-10-04 | 1997-12-09 | Bayer Aktiengesellschaft | Polyether polyols stabilized with tocopherol |
| US5969014A (en) * | 1997-09-23 | 1999-10-19 | Clariant Finance (Bvi) Limited | Synergistic polyamide stabilization method |
| WO2000052090A1 (en) * | 1999-02-26 | 2000-09-08 | Yoshitomi Fine Chemicals, Ltd. | Polymeric material composition and stabilizer composition both containing spirochroman compound |
| US20120146257A1 (en) * | 2010-12-13 | 2012-06-14 | Cytec Technology Corp. | Processing additives and uses of same in rotational molding |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7083743B2 (en) | 1999-12-20 | 2006-08-01 | Clariant Finance (Bvi) Limited | Mixture of phosphanes and chromane derivatives |
| DE19961464A1 (en) * | 1999-12-20 | 2001-06-21 | Clariant Internat Ltd Muttenz | Mixtures containing phosphane and chromane derivatives are useful as stabilizers against the thermo-oxidate decomposition of polymers. |
| CN101182372B (en) * | 2002-07-05 | 2010-12-01 | 沙伯基础创新塑料知识产权有限公司 | Weather-resistant polycarbonate containing N,N'-oxalyl diphenylamine structure unit, manufacturing method therefore and products made thereby |
| KR102081524B1 (en) * | 2015-09-16 | 2020-02-25 | 미쯔이가가꾸가부시끼가이샤 | Polymerizable composition for optical materials, optical material and plastic lens obtained from the composition |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0263524A2 (en) * | 1986-10-10 | 1988-04-13 | BASF Aktiengesellschaft | Stabilizer compositions for plastics |
| JPS63137941A (en) * | 1986-12-01 | 1988-06-09 | Mitsui Toatsu Chem Inc | Polyolefin composition |
| DE3725926A1 (en) * | 1987-08-05 | 1989-02-16 | Basf Ag | Mixture for the stabilisation of polyurethanes |
| EP0312927A2 (en) * | 1987-10-21 | 1989-04-26 | BASF Aktiengesellschaft | Mixture for stabilisation of polyurethanes |
| JPH02225542A (en) * | 1988-08-16 | 1990-09-07 | Chisso Corp | Stabilized polyolefin composition |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8727452D0 (en) * | 1987-11-24 | 1987-12-23 | Sandoz Ltd | Organic compounds |
-
1991
- 1991-10-11 GB GB919121575A patent/GB9121575D0/en active Pending
-
1992
- 1992-10-08 GB GB9221154A patent/GB2260764A/en not_active Withdrawn
- 1992-10-08 DE DE4233973A patent/DE4233973A1/en not_active Withdrawn
- 1992-10-09 FR FR9212199A patent/FR2682392A1/en not_active Withdrawn
- 1992-10-09 JP JP4272027A patent/JPH05214254A/en active Pending
- 1992-10-12 IT ITRM920734A patent/IT1263005B/en active IP Right Grant
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0263524A2 (en) * | 1986-10-10 | 1988-04-13 | BASF Aktiengesellschaft | Stabilizer compositions for plastics |
| US4806580A (en) * | 1986-10-10 | 1989-02-21 | Basf Aktiengesellschaft | Stabilizer mixtures for plastics |
| JPS63137941A (en) * | 1986-12-01 | 1988-06-09 | Mitsui Toatsu Chem Inc | Polyolefin composition |
| DE3725926A1 (en) * | 1987-08-05 | 1989-02-16 | Basf Ag | Mixture for the stabilisation of polyurethanes |
| EP0312927A2 (en) * | 1987-10-21 | 1989-04-26 | BASF Aktiengesellschaft | Mixture for stabilisation of polyurethanes |
| US4925888A (en) * | 1987-10-21 | 1990-05-15 | Basf Aktiengesellschaft | Mixture for stabilizing polyurethanes |
| JPH02225542A (en) * | 1988-08-16 | 1990-09-07 | Chisso Corp | Stabilized polyolefin composition |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2263280B (en) * | 1992-01-17 | 1996-07-31 | Sandoz Ltd | Use of a phosphonite and optionally a phosphite for clarifying propylene polymers |
| GB2278362B (en) * | 1993-05-24 | 1997-08-13 | Sandoz Ltd | Processing stabiliser composition for polymers |
| GB2278362A (en) * | 1993-05-24 | 1994-11-30 | Sandoz Ltd | Processing stabiliser compositions |
| GB2283490A (en) * | 1993-11-03 | 1995-05-10 | Sandoz Ltd | Processing stabilizers for polymers |
| US5695689A (en) * | 1994-10-04 | 1997-12-09 | Bayer Aktiengesellschaft | Polyether polyols stabilized with tocopherol |
| WO1996017886A1 (en) * | 1994-12-06 | 1996-06-13 | Basf Aktiengesellschaft | Stabilized styrene/butadiene block copolymers |
| US6362258B1 (en) | 1995-12-29 | 2002-03-26 | General Electric Company | Stabilized thermoplastic polymer composition |
| EP0781805A1 (en) * | 1995-12-29 | 1997-07-02 | General Electric Company | Stabilized thermoplastic polymer composition |
| EP0805178A1 (en) * | 1996-05-03 | 1997-11-05 | Ciba SC Holding AG | Tocopherol-containing composition as stabiliser for thermoplastic materials |
| US5844027A (en) * | 1996-05-03 | 1998-12-01 | Ciba Specialty Chemicals Corporation | Stabilizer composition for thermoplastic materials |
| US5969014A (en) * | 1997-09-23 | 1999-10-19 | Clariant Finance (Bvi) Limited | Synergistic polyamide stabilization method |
| WO2000052090A1 (en) * | 1999-02-26 | 2000-09-08 | Yoshitomi Fine Chemicals, Ltd. | Polymeric material composition and stabilizer composition both containing spirochroman compound |
| US20120146257A1 (en) * | 2010-12-13 | 2012-06-14 | Cytec Technology Corp. | Processing additives and uses of same in rotational molding |
| US11312043B2 (en) * | 2010-12-13 | 2022-04-26 | Cytec Technology Corp. | Processing additives and uses of same in rotational molding |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2682392A1 (en) | 1993-04-16 |
| JPH05214254A (en) | 1993-08-24 |
| ITRM920734A1 (en) | 1994-04-12 |
| GB9221154D0 (en) | 1992-11-25 |
| GB9121575D0 (en) | 1991-11-27 |
| IT1263005B (en) | 1996-07-23 |
| DE4233973A1 (en) | 1993-04-15 |
| ITRM920734A0 (en) | 1992-10-12 |
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