JP2022548196A - ポリウレタン組成物、それを用いて調製された製品およびその調製方法 - Google Patents
ポリウレタン組成物、それを用いて調製された製品およびその調製方法 Download PDFInfo
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- JP2022548196A JP2022548196A JP2022504188A JP2022504188A JP2022548196A JP 2022548196 A JP2022548196 A JP 2022548196A JP 2022504188 A JP2022504188 A JP 2022504188A JP 2022504188 A JP2022504188 A JP 2022504188A JP 2022548196 A JP2022548196 A JP 2022548196A
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- Prior art keywords
- polyurethane
- polyol
- groups
- ester
- polyol component
- Prior art date
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- 229920002635 polyurethane Polymers 0.000 title claims abstract description 73
- 239000004814 polyurethane Substances 0.000 title claims abstract description 73
- 239000000203 mixture Substances 0.000 title claims abstract description 57
- 238000002360 preparation method Methods 0.000 title description 8
- 229920005862 polyol Polymers 0.000 claims abstract description 203
- 150000003077 polyols Chemical class 0.000 claims abstract description 203
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 110
- 150000002148 esters Chemical class 0.000 claims abstract description 55
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 52
- 229920000570 polyether Polymers 0.000 claims abstract description 52
- 229920001400 block copolymer Polymers 0.000 claims abstract description 45
- 229920005830 Polyurethane Foam Polymers 0.000 claims abstract description 42
- 239000011496 polyurethane foam Substances 0.000 claims abstract description 42
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 24
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 24
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 17
- 230000020169 heat generation Effects 0.000 claims abstract description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 43
- -1 (C 2 -C 10 ) alkylene glycol Chemical compound 0.000 claims description 39
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 22
- 229920001577 copolymer Polymers 0.000 claims description 17
- 239000002202 Polyethylene glycol Substances 0.000 claims description 13
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 13
- 229920001223 polyethylene glycol Polymers 0.000 claims description 13
- 229920001451 polypropylene glycol Polymers 0.000 claims description 8
- 239000001294 propane Substances 0.000 claims description 7
- 150000005846 sugar alcohols Polymers 0.000 claims description 7
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 claims description 6
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 claims description 6
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 5
- 238000005299 abrasion Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 5
- 239000001730 (5R)-5-butyloxolan-2-one Substances 0.000 claims description 3
- WGPCZPLRVAWXPW-NSHDSACASA-N 5-octyloxolan-2-one Chemical compound CCCCCCCC[C@H]1CCC(=O)O1 WGPCZPLRVAWXPW-NSHDSACASA-N 0.000 claims description 3
- GSCLMSFRWBPUSK-UHFFFAOYSA-N beta-Butyrolactone Chemical group CC1CC(=O)O1 GSCLMSFRWBPUSK-UHFFFAOYSA-N 0.000 claims description 3
- IFYYFLINQYPWGJ-VIFPVBQESA-N gamma-Decalactone Natural products CCCCCC[C@H]1CCC(=O)O1 IFYYFLINQYPWGJ-VIFPVBQESA-N 0.000 claims description 3
- WGPCZPLRVAWXPW-LLVKDONJSA-N gamma-Dodecalactone Natural products CCCCCCCC[C@@H]1CCC(=O)O1 WGPCZPLRVAWXPW-LLVKDONJSA-N 0.000 claims description 3
- IPBFYZQJXZJBFQ-UHFFFAOYSA-N gamma-octalactone Chemical compound CCCCC1CCC(=O)O1 IPBFYZQJXZJBFQ-UHFFFAOYSA-N 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 230000000153 supplemental effect Effects 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000006260 foam Substances 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 18
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 12
- 239000004970 Chain extender Substances 0.000 description 10
- 150000002596 lactones Chemical class 0.000 description 10
- 239000000654 additive Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 229920005906 polyester polyol Polymers 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- 239000004604 Blowing Agent Substances 0.000 description 7
- 238000012512 characterization method Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 239000004698 Polyethylene Substances 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 229910052726 zirconium Inorganic materials 0.000 description 6
- 239000004971 Cross linker Substances 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 239000011246 composite particle Substances 0.000 description 4
- 239000011258 core-shell material Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000005096 rolling process Methods 0.000 description 4
- 238000002411 thermogravimetry Methods 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000004872 foam stabilizing agent Substances 0.000 description 3
- 235000019256 formaldehyde Nutrition 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 150000003141 primary amines Chemical group 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 229920005604 random copolymer Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 229920013701 VORANOL™ Polymers 0.000 description 2
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 2
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- PYBNTRWJKQJDRE-UHFFFAOYSA-L dodecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O PYBNTRWJKQJDRE-UHFFFAOYSA-L 0.000 description 2
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- SHXHPUAKLCCLDV-UHFFFAOYSA-N 1,1,1-trifluoropentane-2,4-dione Chemical compound CC(=O)CC(=O)C(F)(F)F SHXHPUAKLCCLDV-UHFFFAOYSA-N 0.000 description 1
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- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
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- GGSRTHRSSCWGGK-UHFFFAOYSA-L 2,2-dibutyl-5-hydroxy-1,3,2-dioxastannepane-4,7-dione Chemical compound CCCC[Sn]1(CCCC)OC(=O)CC(O)C(=O)O1 GGSRTHRSSCWGGK-UHFFFAOYSA-L 0.000 description 1
- BFXXDIVBYMHSMP-UHFFFAOYSA-L 2,2-diethylhexanoate;tin(2+) Chemical compound [Sn+2].CCCCC(CC)(CC)C([O-])=O.CCCCC(CC)(CC)C([O-])=O BFXXDIVBYMHSMP-UHFFFAOYSA-L 0.000 description 1
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 description 1
- VZDIRINETBAVAV-UHFFFAOYSA-N 2,4-diisocyanato-1-methylcyclohexane Chemical compound CC1CCC(N=C=O)CC1N=C=O VZDIRINETBAVAV-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
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- C08G18/4252—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups derived from polyols containing at least one ether group and polycarboxylic acids derived from polyols containing polyether groups and polycarboxylic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Abstract
Description
(A)少なくとも1つのポリイソシアネート化合物を第1のポリオール成分と反応させることによって調製された1つ以上のポリウレタンプレポリマーと、
(B)第2のポリオール成分と、を含み、
第1のポリオール成分および第2のポリオール成分のうちの少なくとも1つは、出発物質ポリエーテルポリオールを、任意選択で、C1-C12アルキル、C2-C12アルケニル、窒素含有基、リン含有基、硫黄含有基およびハロゲンからなる群から選択される1つ以上の置換基で置換されるC4-C20ラクトンと反応させることにより合成されたエステル/エーテルブロックコポリマーポリオールを含む。本開示の好ましい実施形態によれば、出発物質ポリエーテルポリオールは、ポリ(C2-C10)アルキレングリコール、複数の(C2-C10)アルキレングリコールのコポリマー、またはコア相とポリ(C2-C10)アルキレングリコールまたはそのコポリマーに基づくシェル相とを有するポリマーポリオールであり、ポリ(C2-C10)アルキレングリコールまたはそのコポリマーの例には、ポリエチレングリコール、ポリプロピレングリコール、ポリテトラメチレングリコール、ポリ(2-メチル-1,3-プロパングリコール)、およびポリ(エチレンオキシド-ポリプロピレンオキシド)グリコールが含まれ得、出発物質ポリエーテルポリオールは、100~5,000、好ましくは200~3,000の分子量および1.5~5.0の平均ヒドロキシル官能価を有し、C4-C20ラクトンは、β-ブチロラクトン、γ-ブチロラクトン、γ-バレロラクトン、ε-カプロラクトン、γ-カプロラクトン、γ-オクタラクトン、γ-デカラクトン、γ-ドデカラクトン、およびそれらの任意の組み合わせからなる群から選択され、C1-C12アルキル、C2-C12アルケニル、窒素含有基、リン含有基、硫黄含有基およびハロゲンからなる群で置換するなど、上記のすべてのラクトンは、任意選択で置換することができる。本開示の別の好ましい実施形態によれば、エステル/エーテルブロックコポリマーポリオールが、少なくとも800g/molの分子量および1.5~5.0の平均ヒドロキシル官能価を有し、出発物質ポリエーテルポリオールとC4-C20ラクトンとの重量比が、0.05/0.95~0.95/0.05である。
i)少なくとも1つのポリイソシアネート化合物を第1のポリオール成分と反応させてポリウレタンプレポリマーを形成するステップと、
ii)ポリウレタンプレポリマーを第2のポリオール成分と反応させてマイクロセルラーポリウレタンフォームを形成するステップと、を含み、
エステル/エーテルブロックコポリマーポリオールに由来する繰り返し単位が、ポリウレタンマイクロセルラーポリウレタンフォームのポリウレタン主鎖で共有結合している。
異なるポリオールおよびプレポリマーの粘度を、粘度分析器(CAP、Brookfield)を使用して様々な温度で測定した。酸価、ヒドロキシル価、およびNCO値は、それぞれASTMD4662、ASTMD4274、およびASTM D5155に従って決定された。引張強度、破断点伸び、および引裂強度は、試験方法DIN 53543に従ってGotech AI-7000S1万能試験機で測定された。動的機械分析(DMA)は、TA RSA G2分析器で、1Hzの周波数でひずみ制御モードで実施された。熱重量分析(TGA)は、TA-Q500分析器で、大気中0℃~600℃の温度範囲で実施された。示差走査熱量測定(DSC)は、N2雰囲気下で10℃/分の冷却速度および20℃/分の加熱速度でTA Q1500分析器で実施された。
本開示による2つのエステル/エーテルブロックコポリマーポリオールは、表2にリストされたレシピを使用することにより、ポリエーテルポリオール(Voranol 1000LMまたはVoranol WD2104、50重量%)、ラクトン(ε-カプロラクトン、50重量%)およびエステル化触媒(チタン酸n-ブチルTBT、エステル/エーテルブロックコポリマーポリオールの総重量に基づいて25ppm)を真空ポンプおよび油浴を備えた鋼の反応器に室温の窒素雰囲気下で供給するという一般的な手順に従って、ポリエーテルポリオールをマクロ開始剤として使用した、ε-カプロラクトンの開環反応を介して合成した。反応系は、17時間撹拌しながら120℃に保ち、続いて150mbar下で真空を適用し、さらに3時間にわたり135℃で加熱した。生成物は80℃に冷却され、濾過され、パッケージ化され、酸価、ヒドロキシル価、および粘度測定のためにサンプリングされた。これらの2つの調製例1~2で調製された生成物は、それぞれ、PCPC2000-1およびPCPC2000-2と呼ばれる。特性評価の結果は、すべて表2にも要約した。
表3に示されるレシピを用いた以下の一般的な手順に従って、上記の実施例で調製されたポリオールならびにPTMEG2000をMDIと反応させることにより、4つの異なるプレポリマーが調製された。MDI(ISONATE 125MH)および抑制剤(塩化ベンゾイル)を最初に真空ポンプと油浴を備えたタンク反応器に入れ、次に撹拌しながら60℃の温度に保った。反応器に投入する前に、ポリオールを60℃で12時間予熱した。上記ポリオールの供給中、反応器は75℃未満の温度に保たれた。次に、混合物を80℃に加熱し、撹拌しながら150分間反応させた。次に、反応系を50℃に冷却し、そこにIsonate 143LPおよびIsonate PR 7020を添加し、反応器内の内容物をさらに20分間撹拌した。続いて、NCO含有量を定量し、真空下で30分間脱気した後、最終的なプレポリマー生成物が得られた。得られたプレポリマーは、約19重量%のNCO含有量を有する。特性評価の結果を、表3に要約した。低温での貯蔵安定性を改善するために、2つのカルボジイミド修飾MDI Isonate 143LPおよびIsonate PR7020がプレポリマーに組み込まれた。
ポリオール成分は、ポリオール、鎖延長剤、触媒、界面活性剤、発泡剤、およびその他の添加剤を一緒に混合することにより、表4に示すレシピに従って事前に作製された。上記調製例で合成したポリウレタンプレポリマーを、50℃でポリオール成分と混合し、混合物を低圧機(緑)を用いて50℃で金型に注入した。ポリオール成分およびプレポリマーの反応は、混合した後即座に生じ、成形サンプルを5分間、50℃で硬化した後に離型した。後硬化ポリウレタンフォームサンプルは、試験前に室温で少なくとも24時間保管された。
直径24インチ、成形密度350kg/m3のポリウレタンソリッドタイヤを、上記の実施例1~6で得られたサンプルを使用して顧客の現場で製造し、その包括的な性能を評価するために転がり試験によって特性評価した。転がり試験は、30km/時のライン速度、65kgの荷重、2つの高さ10mmの障害物を用いて実施し、室温で1時間継続した。試験条件および特性評価の結果を、表5に要約した。
上記を考慮して、エステル/エーテルランダムコポリマーポリオールは、ウレタン系の優れた加工および貯蔵安定性、ならびに最終ポリウレタン材料の高い引裂強度、高い耐摩耗性、低い内部発熱および高い熱安定性の間の優れた性能バランスを与え、マイクロセルラー部品の製造を支持し、ソリッドタイヤのような多くの関連用途で役立つ。
Claims (11)
- ポリウレタン組成物であって、
(A)少なくとも1つのポリイソシアネート化合物を第1のポリオール成分と反応させることによって調製された1つ以上のポリウレタンプレポリマーと、
(B)第2のポリオール成分と、を含み、
前記第1のポリオール成分および前記第2のポリオール成分のうちの少なくとも1つは、出発物質ポリエーテルポリオールを、任意選択で、C1-C12アルキル、C2-C12アルケニル、窒素含有基、リン含有基、硫黄含有基およびハロゲンからなる群から選択される1つ以上の置換基で置換されるC4-C20ラクトンと反応させることにより合成されたエステル/エーテルブロックコポリマーポリオールを含む、ポリウレタン組成物。 - 前記ポリイソシアネート化合物が、少なくとも2つのイソシアネート基を含むC4-C12脂肪族ポリイソシアネート、少なくとも2つのイソシアネート基を含むC6-C15脂環式または芳香族ポリイソシアネート、少なくとも2つのイソシアネート基を含むC7-C15芳香脂肪族(araliphatic)ポリイソシアネート、およびそれらの任意の組み合わせからなる群から選択される、請求項1に記載のポリウレタン組成物。
- 前記出発物質ポリエーテルポリオールが、ポリ(C2-C10)アルキレングリコール、複数の(C2-C10)アルキレングリコールのコポリマー、またはコア相とポリ(C2-C10)アルキレングリコールまたはそのコポリマーからなるシェル相とを有するポリマーポリオールであって、前記出発物質ポリエーテルポリオールが、100~5,000の分子量および1.5~5.0の平均ヒドロキシル官能価を有する、請求項1に記載のポリウレタン組成物。
- 前記出発物質ポリエーテルポリオールが、ポリエチレングリコール、ポリプロピレングリコール、ポリテトラメチレングリコール、ポリ(2-メチル-1,3-プロパングリコール)、およびそれらの任意のコポリマーからなる群から選択され、前記出発物質ポリエーテルポリオールが、200~3,000の分子量および1.5~5.0の平均ヒドロキシル官能価を有する、請求項1に記載のポリウレタン組成物。
- 前記C4-C20ラクトンが、β-ブチロラクトン、γ-ブチロラクトン、γ-バレロラクトン、ε-カプロラクトン、γ-カプロラクトン、γ-オクタラクトン、γ-デカラクトン、γ-ドデカラクトン、およびそれらの任意の組み合わせからなる群から選択され、任意選択で、C1-C12アルキル、C2-C12アルケニル、窒素含有基、リン含有基、硫黄含有基およびハロゲンからなる群から選択される1つ以上の置換基で置換される、請求項1に記載のポリウレタン組成物。
- 前記エステル/エーテルブロックコポリマーポリオールが、少なくとも800g/molの分子量および1.5~5.0の平均ヒドロキシル官能価を有し、前記出発物質ポリエーテルポリオールと前記C4-C20ラクトンとの重量比が、0.05/0.95~0.95/0.05である、請求項1に記載のポリウレタン組成物。
- 前記第1のポリオール成分および前記第2のポリオール成分のうちの少なくとも1つが、少なくとも2つのヒドロキシル基を含むC2-C16脂肪族多価アルコール、少なくとも2つのヒドロキシル基を含むC6-C15脂環式または芳香族多価アルコール、少なくとも2つのヒドロキシル基を含むC7-C15芳香脂肪族多価アルコール、100~5,000の分子量および1.5~5.0の平均ヒドロキシル官能価を有するポリエステルポリオール、コア相とポリオールに基づくシェル相とを有するポリマーポリオール、ポリ(C2-C10)アルキレングリコールまたは複数の(C2-C10)アルキレングリコールのコポリマーである補足的な第2のポリエーテルポリオール、ならびにそれらの組み合わせからなる群から選択される、前記エステル/エーテルブロックコポリマーポリオール以外のポリオールを含み、前記補足的なポリエーテルポリオールが、前記出発物質ポリエーテルポリオールと同一または異なる、請求項1に記載のポリウレタン組成物。
- 請求項1~7のいずれか一項に記載のポリウレタン組成物で調製されたマイクロセルラーポリウレタンフォームであって、前記エステル/エーテルブロックコポリマーポリオールに由来する繰り返し単位が、前記ポリウレタンマイクロセルラーポリウレタンフォームのポリウレタン主鎖で共有結合し、前記マイクロセルラーポリウレタンフォームが100~900kg/m3の密度を有する、マイクロセルラーポリウレタンフォーム。
- 請求項8に記載のマイクロセルラーポリウレタンフォームで調製された成形品であって、タイヤ、履物、靴底、家具、枕、クッション、玩具および裏地からなる群から選択される、成形品。
- 請求項8に記載のマイクロセルラーポリウレタンフォームを調製するための方法であって、
i)少なくとも1つのポリイソシアネート化合物を第1のポリオール成分と反応させて前記ポリウレタンプレポリマーを形成するステップと、
ii)前記ポリウレタンプレポリマーを前記第2のポリオール成分と反応させて前記マイクロセルラーポリウレタンフォームを形成するステップと、を含み、
前記エステル/エーテルブロックコポリマーポリオールに由来する繰り返し単位が、前記ポリウレタンマイクロセルラーポリウレタンフォームのポリウレタン主鎖で共有結合している、方法。 - マイクロセルラーポリウレタンフォームの性能特性を改善するための方法であって、出発物質ポリエーテルポリオールを、ポリウレタンマイクロセルラーポリウレタンフォームのポリウレタン主鎖中のC4-C20ラクトンと反応させることによって合成されたエステル/エーテルブロックコポリマーポリオールに由来する繰り返し単位を、前記ポリウレタンマイクロセルラーポリウレタンフォームのポリウレタン主鎖で共有結合させるステップを含み、前記性能特性には、内部発熱、熱安定性、引裂強度、粘度、耐摩耗性、および耐加水分解性のうちの少なくとも1つが含まれる、方法。
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