JPH0240245B2 - - Google Patents
Info
- Publication number
- JPH0240245B2 JPH0240245B2 JP58117901A JP11790183A JPH0240245B2 JP H0240245 B2 JPH0240245 B2 JP H0240245B2 JP 58117901 A JP58117901 A JP 58117901A JP 11790183 A JP11790183 A JP 11790183A JP H0240245 B2 JPH0240245 B2 JP H0240245B2
- Authority
- JP
- Japan
- Prior art keywords
- vinyl
- diisocyanate
- reaction
- vinyl ether
- polyhydroxyl compound
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 27
- 229920005862 polyol Polymers 0.000 claims description 24
- 238000004519 manufacturing process Methods 0.000 claims description 23
- 150000003077 polyols Chemical class 0.000 claims description 23
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 22
- 229920000570 polyether Polymers 0.000 claims description 22
- 229920002554 vinyl polymer Polymers 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000004814 polyurethane Substances 0.000 claims description 16
- 229920002635 polyurethane Polymers 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 13
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 13
- 239000000178 monomer Substances 0.000 claims description 12
- 229920001228 polyisocyanate Polymers 0.000 claims description 11
- 239000005056 polyisocyanate Substances 0.000 claims description 11
- 238000005886 esterification reaction Methods 0.000 claims description 7
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 7
- 230000032050 esterification Effects 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 6
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 5
- 238000007259 addition reaction Methods 0.000 claims description 4
- 238000006317 isomerization reaction Methods 0.000 claims description 4
- 238000012719 thermal polymerization Methods 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 238000000034 method Methods 0.000 description 16
- -1 ester polyol Chemical class 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 8
- 239000004604 Blowing Agent Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 239000012752 auxiliary agent Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229920005830 Polyurethane Foam Polymers 0.000 description 3
- 125000003545 alkoxy group Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical class 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000001879 gelation Methods 0.000 description 3
- 125000005843 halogen group Chemical class 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical class [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000006353 oxyethylene group Chemical group 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000011496 polyurethane foam Substances 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
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 239000004872 foam stabilizing agent Substances 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- XOESUTAJRUJGHH-QXMHVHEDSA-N (Z)-1-ethenoxyoctadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOC=C XOESUTAJRUJGHH-QXMHVHEDSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- IZMZREOTRMMCCB-UHFFFAOYSA-N 1,4-dichloro-2-ethenylbenzene Chemical compound ClC1=CC=C(Cl)C(C=C)=C1 IZMZREOTRMMCCB-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WMVUYUVKNFDYAF-UHFFFAOYSA-N 1-(4-prop-1-en-2-ylphenyl)ethanone Chemical compound CC(=C)C1=CC=C(C(C)=O)C=C1 WMVUYUVKNFDYAF-UHFFFAOYSA-N 0.000 description 1
- LFSHREXVLSTLFB-UHFFFAOYSA-N 1-cyanoethenyl acetate Chemical compound CC(=O)OC(=C)C#N LFSHREXVLSTLFB-UHFFFAOYSA-N 0.000 description 1
- GXZPMXGRNUXGHN-UHFFFAOYSA-N 1-ethenoxy-2-methoxyethane Chemical compound COCCOC=C GXZPMXGRNUXGHN-UHFFFAOYSA-N 0.000 description 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- NSOAQRMLVFRWIT-UHFFFAOYSA-N 1-ethenoxydecane Chemical compound CCCCCCCCCCOC=C NSOAQRMLVFRWIT-UHFFFAOYSA-N 0.000 description 1
- UKDKWYQGLUUPBF-UHFFFAOYSA-N 1-ethenoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOC=C UKDKWYQGLUUPBF-UHFFFAOYSA-N 0.000 description 1
- YAOJJEJGPZRYJF-UHFFFAOYSA-N 1-ethenoxyhexane Chemical compound CCCCCCOC=C YAOJJEJGPZRYJF-UHFFFAOYSA-N 0.000 description 1
- MIMKRVLJPMYKID-UHFFFAOYSA-N 1-ethenoxynonane Chemical compound CCCCCCCCCOC=C MIMKRVLJPMYKID-UHFFFAOYSA-N 0.000 description 1
- QJJDJWUCRAPCOL-UHFFFAOYSA-N 1-ethenoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOC=C QJJDJWUCRAPCOL-UHFFFAOYSA-N 0.000 description 1
- XXCVIFJHBFNFBO-UHFFFAOYSA-N 1-ethenoxyoctane Chemical compound CCCCCCCCOC=C XXCVIFJHBFNFBO-UHFFFAOYSA-N 0.000 description 1
- LPYHXIHXJREIMY-UHFFFAOYSA-N 1-ethenoxytetradecane Chemical compound CCCCCCCCCCCCCCOC=C LPYHXIHXJREIMY-UHFFFAOYSA-N 0.000 description 1
- ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(C=2C=C(C)C(N=C=O)=CC=2)=C1 ICLCCFKUSALICQ-UHFFFAOYSA-N 0.000 description 1
- OGMSGZZPTQNTIK-UHFFFAOYSA-N 1-methyl-2-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1C OGMSGZZPTQNTIK-UHFFFAOYSA-N 0.000 description 1
- BZVILVRXAQDZJW-UHFFFAOYSA-N 2,2-dichloroethenyl acetate Chemical compound CC(=O)OC=C(Cl)Cl BZVILVRXAQDZJW-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- XYPHEDNABNFRBL-UHFFFAOYSA-N 2-chloroethenyl acetate Chemical compound CC(=O)OC=CCl XYPHEDNABNFRBL-UHFFFAOYSA-N 0.000 description 1
- REYKZNSVWAIXEG-UHFFFAOYSA-N 2-ethenoxy-4-methylpentane Chemical compound CC(C)CC(C)OC=C REYKZNSVWAIXEG-UHFFFAOYSA-N 0.000 description 1
- KCAHZJOADZUUDY-UHFFFAOYSA-N 2-ethenoxy-5-ethylnonane Chemical compound CCCCC(CC)CCC(C)OC=C KCAHZJOADZUUDY-UHFFFAOYSA-N 0.000 description 1
- TVDQSMSFFAXTJL-UHFFFAOYSA-N 2-ethenoxyoctane Chemical compound CCCCCCC(C)OC=C TVDQSMSFFAXTJL-UHFFFAOYSA-N 0.000 description 1
- GNUGVECARVKIPH-UHFFFAOYSA-N 2-ethenoxypropane Chemical compound CC(C)OC=C GNUGVECARVKIPH-UHFFFAOYSA-N 0.000 description 1
- YDNVDUXXZZLBPG-UHFFFAOYSA-N 2-methoxyethenyl acetate Chemical compound COC=COC(C)=O YDNVDUXXZZLBPG-UHFFFAOYSA-N 0.000 description 1
- CTHJQRHPNQEPAB-UHFFFAOYSA-N 2-methoxyethenylbenzene Chemical compound COC=CC1=CC=CC=C1 CTHJQRHPNQEPAB-UHFFFAOYSA-N 0.000 description 1
- BTOVVHWKPVSLBI-UHFFFAOYSA-N 2-methylprop-1-enylbenzene Chemical compound CC(C)=CC1=CC=CC=C1 BTOVVHWKPVSLBI-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- QZWKEPYTBWZJJA-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine-4,4'-diisocyanate Chemical compound C1=C(N=C=O)C(OC)=CC(C=2C=C(OC)C(N=C=O)=CC=2)=C1 QZWKEPYTBWZJJA-UHFFFAOYSA-N 0.000 description 1
- DSSAWHFZNWVJEC-UHFFFAOYSA-N 3-(ethenoxymethyl)heptane Chemical compound CCCCC(CC)COC=C DSSAWHFZNWVJEC-UHFFFAOYSA-N 0.000 description 1
- WDGNEDMGRQQNNI-UHFFFAOYSA-N 3-(ethenoxymethyl)pentane Chemical compound CCC(CC)COC=C WDGNEDMGRQQNNI-UHFFFAOYSA-N 0.000 description 1
- REEBWSYYNPPSKV-UHFFFAOYSA-N 3-[(4-formylphenoxy)methyl]thiophene-2-carbonitrile Chemical compound C1=CC(C=O)=CC=C1OCC1=C(C#N)SC=C1 REEBWSYYNPPSKV-UHFFFAOYSA-N 0.000 description 1
- FWLGYSGTHHKRMZ-UHFFFAOYSA-N 3-ethenoxy-2,2-dimethylbutane Chemical compound CC(C)(C)C(C)OC=C FWLGYSGTHHKRMZ-UHFFFAOYSA-N 0.000 description 1
- CWVCFFRZNFTMBC-UHFFFAOYSA-N 3-ethenoxy-2,4-dimethylpentane Chemical compound CC(C)C(C(C)C)OC=C CWVCFFRZNFTMBC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-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
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- JGCUIOIXGKBHJU-UHFFFAOYSA-N N=C=O.N=C=O.NC(N)=O Chemical compound N=C=O.N=C=O.NC(N)=O JGCUIOIXGKBHJU-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- QROGIFZRVHSFLM-QHHAFSJGSA-N [(e)-prop-1-enyl]benzene Chemical compound C\C=C\C1=CC=CC=C1 QROGIFZRVHSFLM-QHHAFSJGSA-N 0.000 description 1
- DQJJXEZXOYPSNJ-UHFFFAOYSA-N [2,3-bis(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=CC(CO)=C1CO DQJJXEZXOYPSNJ-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- ATMLPEJAVWINOF-UHFFFAOYSA-N acrylic acid acrylic acid Chemical compound OC(=O)C=C.OC(=O)C=C ATMLPEJAVWINOF-UHFFFAOYSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- IHXBXGHGYCSRAP-UHFFFAOYSA-N bis(ethenyl) benzene-1,4-dicarboxylate Chemical compound C=COC(=O)C1=CC=C(C(=O)OC=C)C=C1 IHXBXGHGYCSRAP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 239000012971 dimethylpiperazine Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- IYNRVIKPUTZSOR-HWKANZROSA-N ethenyl (e)-but-2-enoate Chemical compound C\C=C\C(=O)OC=C IYNRVIKPUTZSOR-HWKANZROSA-N 0.000 description 1
- LPUZTLKYAOOFDX-QXMHVHEDSA-N ethenyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC=C LPUZTLKYAOOFDX-QXMHVHEDSA-N 0.000 description 1
- YCUBDDIKWLELPD-UHFFFAOYSA-N ethenyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC=C YCUBDDIKWLELPD-UHFFFAOYSA-N 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- PQLFROTZSIMBKR-UHFFFAOYSA-N ethenyl carbonochloridate Chemical compound ClC(=O)OC=C PQLFROTZSIMBKR-UHFFFAOYSA-N 0.000 description 1
- JZRGFKQYQJKGAK-UHFFFAOYSA-N ethenyl cyclohexanecarboxylate Chemical compound C=COC(=O)C1CCCCC1 JZRGFKQYQJKGAK-UHFFFAOYSA-N 0.000 description 1
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 1
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Description
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This invention relates to an improved method of making polyurethane materials. More specifically, the present invention relates to a method for producing a polyurethane material using a polyether polyol substantially graft-polymerized with a vinyl monomer. Conventionally, methods for improving physical properties such as strength and rubber-like elasticity of polyurethane materials include methods of dispersing vinyl polymers in polyether polyols, methods of polymerizing vinyl monomers in polyether polyols, and methods of using polyether polyols. There have been methods such as partially grafting a vinyl polymer onto
15108), but polyurethane materials obtained using these polyols have not yet shown sufficiently satisfactory physical properties. In other words, the polyols obtained by the methods described in these publications have extremely low grafting rates, or are simply a mixture of vinyl polymer and polyether polyol, and may be used during storage or in a premix (polyol, urethanization catalyst, foaming catalyst, etc.). Since the vinyl polymer separates during the preparation (mixture of foam stabilizer, etc.) or during the urethanization reaction, the resulting polyurethane material becomes non-uniform, and furthermore, cell roughness occurs during the production of polyurethane foam. In addition, even in polyurethane materials obtained by careful manipulation so that the vinyl polymer does not separate, the vinyl polymer is essentially contained only as a mixture, and its physical properties may vary. We cannot expect much improvement. As a method to improve this drawback, polyhydroxyl, which improves the grafting rate of vinyl polymers, is produced by reacting an unsaturated ester polyol obtained by reacting a polyether polyol with an unsaturated dibasic acid and a vinyl monomer. Although there are methods to obtain compounds (Japanese Patent Publication No. 51-40914, Japanese Patent Publication No. 51-40915)
(No. Publication), thickening during the polymerization reaction of vinyl monomers,
Gelation occurs and it is difficult to obtain the desired product. If the amount of unsaturated acid used is reduced in order to avoid thickening and gelation, the grafting rate will decrease and the product will become non-uniform. There is also a method of using an ester obtained by combining a large amount of saturated acid or a vinyl monomer with an unsaturated acid with low copolymerizability, but this essentially reduces the amount of unsaturated acid used and produces a uniform result. It is difficult to obtain polyhydroxyl compounds with low viscosity. Furthermore, in the reaction between a polyol and a dicarboxylic acid, the number of functional groups is reduced due to the formation of intramolecular esters. In particular, the intramolecular diester produced from trifunctional polyether and dicarboxylic acid, which is often used for flexible urethane foams, becomes monofunctional and acts as a terminator for polymerization when reacting with polyisocyanate. In polyhydroxyl compounds obtained by conventional methods, contamination of hydroxyl compounds with monofunctional or low functional groups is unavoidable, and the physical properties of polyurethane materials using these compounds are not satisfactory. SUMMARY OF THE INVENTION An object of the present invention is to provide a method for producing polyurethane materials that overcomes the drawbacks of the conventional methods. More specifically, an object of the present invention is to provide a polyurethane material that is particularly excellent in physical properties such as strength and rubber elasticity. The requirements for the structure of the present invention are that polyisocyanate and polyhydroxyl compound are the main reaction components,
Polyester obtained by treating polyether polyol and itaconic acid at 170 to 230°C and simultaneously performing esterification, thermal polymerization, isomerization, and addition reaction as at least one component of a polyhydroxyl compound when producing a polyurethane substance. The purpose of this invention is to use a polyhydroxyl compound obtained by graft polymerizing a radically polymerizable vinyl monomer. The polyether polyol used to obtain the polyhydroxyl compound used in the present invention can be appropriately selected from the conventionally known polyether polyol groups, but examples of one representative group of compounds include active hydrogen atoms. General formula as obtained by reacting a compound and alkylene oxide: A[(R 1 O) o1 H] f1 (1) (where A is a compound residue containing an active hydrogen atom,
R1 is an alkylene group, n1 is a number indicating the number of polymerized oxyalkylene groups, and is preferably a number such that the hydroxyl value of the polyether polyol is 100 to 25 mgKOH/g, and n1 is different for each chain. You can leave it on. f1 is 1 or a number of 1 or more and has the same value as the number of functional groups in A, preferably an average of 2 to 6, and particularly preferably a number of 2 to 6. ) or a mixture thereof. Examples of compounds corresponding to A in the above general formula are alcohols, alkanediols (e.g., ethylene glycol, propene glycol), alkanetriols (e.g., glycerin, trimethylolpropane, hexanetriol), alkane polyols (e.g., pentaerythritol). , xylitol, sorbitol), alicyclic polyhydric alcohols (e.g. inositol, 2,2-bis-(4-hydroxylcyclohexyl)propane), monosaccharides or their derivatives (e.g. methyl glycoseed), aromatic polyhydric alcohols Hydrolic alcohols (e.g. trimethylolbenzene) and polyhydric phenols (e.g. phenol-formalin initial condensate) can be mentioned. In addition, the above general formula K(R 1 O) o1 is, for example, A polyoxypropylene chain represented by (-CH 2 -
A polyoxybutylene chain represented by CH 2 -CH 2 -CH 2 -O-) or a polyoxybutylene chain such as that obtained by polymerization of butylene oxide, or a polyoxybutylene chain such as that obtained by copolymerization or block polymerization of ethylene oxide and propylene oxide. polyoxyalkylene chains etc. obtained by Thermal polymerization, isomerization, and addition reactions of itaconic acid esters are described in J. Polymer. Sci. Part C, 1117-1137 (1969).
As reported in , this is already known, and in the conventional method, it was carried out at a relatively low temperature, for example, 150° C. or lower, in order to avoid the progress of reactions other than esterification. The feature of the present invention is that esters obtained by processing at 170 to 230â, that is, thermal polymerization at the same time as esterification,
The point is that polyester obtained by proceeding with isomerization and addition reactions is used. More specifically, by proceeding with a reaction other than esterification at the same time as esterification, the purpose is to obtain a polyester that is polyfunctionalized and has a large polyether chain relative to the unsaturated bond that is the itaconic acid residue. It's about using it. That is, polyfunctionalization of esters contributes to increasing the crosslinking density of polyurethane, and the use of polyesters with large polyether chains for unsaturated bonds reduces gelation and high In addition to avoiding viscosity, it is possible to obtain a polyhydroxyl compound that is a more homogeneous and more stable graft polymer by increasing the affinity with other polyhydroxyl compounds, polyether polyols, and using this polyurethane material. Its physical properties are extremely high. The reaction between polyether polyol and itaconic acid, which is the first step in obtaining the polyhydroxyl compound of the present invention, is carried out at 170°C to 230°C. 170â
At lower temperatures, the above-mentioned ester modification reaction does not proceed. Furthermore, if the temperature is higher than 230°C, the polyether polyol will deteriorate and good results will not be obtained. The charging ratio of itaconic acid and polyether polyol may be any ratio, but considering the efficiency of the reaction tank, the viscosity of the product, etc., it is 0.1 to 0.9 mol:
1 mol is preferred. The catalyst may be one commonly used, such as sulfuric acid, para-toluenesulfonic acid, tin chloride, tetraisopropyl titanate, and the like. The second step, the polymerization of the vinyl monomer, is usually carried out in a polyether polyol, and the amount of the above-mentioned characteristic ester used at this time is preferably 5 to 100 parts per 95 to 0 parts of the polyether polyol. Vinyl monomers to be graft copolymerized by the method of the present invention include methyl vinyl ether, isopropyl vinyl ether, ethyl vinyl ether, isobutyl vinyl ether, n-butyl vinyl ether, 2-chloroethyl vinyl ether,
2-ethylhexyl vinyl ether, 2-methoxyethyl vinyl ether, n-hexyl vinyl ether, n-octyl vinyl ether, 1-methyl-2,2-dimethylpropyl vinyl ether,
2-ethyl butyl vinyl ether, 1,3-dimethylbutyl vinyl ether, diisopropyl methyl vinyl ether, 1-methylheptyl vinyl ether, n-nonyl vinyl ether, n-decyl vinyl ether, 1-methyl-4-ethyloctyl vinyl ether, n-tetradecyl vinyl ether, Vinyl ethers such as n-hexadecyl vinyl ether, n-octadecyl vinyl ether, oleyl vinyl ether; vinyl acetate, monochlorovinyl acetate, dichlorovinyl acetate, methoxyvinyl acetate, vinyl thioacetate, phenyl vinyl acetate, isopropiovinyl acetate, α-cyanovinyl acetate , vinyl formate, vinyl chloroformate, vinyl propionate, vinyl butyrate, vinyl trimethyl acetate, vinyl α-ethyl caproate, vinyl laurate, vinyl stearate, vinyl acrylate,
Vinyl esters such as vinyl crotonate, vinyl oleate, vinyl cyclohexylcarboxylate, vinyl benzoate, divinyl terephthalate; acrylic acid, ethyl acrylate, n-propyl acrylate, isopropyl acrylate, n-acrylate
Butyl, isobutyl acrylate, tert acrylate
- Acrylic acid or its esters such as butyl, α-chloroacrylic acid ester; methacrylic acid,
Methacrylic acid or its esters such as methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, isopropyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, tert-butyl methacrylate; styrene, methylstyrene, dimethylstyrene, Ethylstyrene, methoxystyrene, divinylbenzene, α-methylstyrene, isopropenyltoluene, 4-acetyl-α-methylstyrene, β-methylstyrene,
Chlorstyrene, 2,5-dichlorostyrene, α
- Styrene derivatives such as chlorstyrene; examples include acrylonitrile, methacrylonitrile, acrylamide, methacrylamide or substituted products thereof. The vinyl monomer can be used in any proportion to the above polyester and polyether polyol if present, but in order to obtain a good polyurethane foam, preferably 3 to 40% by weight, particularly preferably 5 to 30% by weight. It is preferable to use vinyl monomers in proportions of % by weight. The grafting reaction may be carried out by a conventionally known method, and an appropriate catalyst may also be used. Further, depending on the case, a polyether polyol or the like may be added during or after the reaction. As is well known, a polyurethane substance is made by using polyisocyanate or a reactive substance such as polyisocyanate and a polyhydroxyl compound or this and other reactive substances as reaction raw materials and reacting them in an appropriate manner depending on the purpose. means a polymer containing a large number of urethane condensations, such as those obtained by a one-shot process in which a mixed polyisocyanate of polyurethane foam and a polyhydroxyl compound are reacted in one step in the presence of a blowing agent and a suitable auxiliary agent. is a total prepolymer method in which a prepolymer obtained by reacting an excess amount of polyisocyanate and a polyhydroxyl compound is reacted with water in the presence of a suitable auxiliary agent.
Alternatively, a semi-prepolymer method in which a prepolymer obtained by reacting an excess amount of polyisocyanate and a polyhydroxyl compound and an additional amount of the polyhydroxyl compound are reacted in the presence of a blowing agent and other suitable auxiliary agents. You can get it by twisting it. The blowing agent here includes reactive blowing agents such as water, but non-reactive blowing agents such as low-boiling point halogenated hydrocarbons are preferred in view of the physical properties of the resulting foam, especially brittleness. . Other auxiliary agents include catalysts, foaming regulators (foam stabilizers), colorants,
Fillers, flame retardants, etc. are used. Here, preferred polyisocyanates have the general formula (Here ã is a benzene ring or naphthalene ring, â
NCO is a nuclear-substituted isocyanate group; , 2,6-toluylene diisocyanate, 1,4-naphthylene diisocyanate,
1,5-naphthylene diisocyanate, 1,3-
Phenylene diisocyanate, 1,4-phenylene diisocyanate, 1-isopropylbenzole-2,4-diisocyanate): General formula (Here ã is a benzene ring or naphthalene ring, -
(CH 2 ) n NCO is a nuclear-substituted alkylene isocyanate group, X is a nuclear-substituted halogen atom or alkyl or alkoxyl group having 3 or less carbon atoms, m is 1 or 2, and n' is 0, 1 or 2). The indicated diisocyanate (e.g. Ï, Ïâ²-diisocyanate-1,2
-dimethylbenzole, Ï,Ï'-diisocyanate-1,3-dimethylbenzole): General formula (Here Aâ² is âCH 2 â,
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ã«ç€ºãã[Formula] An alkylene group having 3 or less carbon atoms, ã is a benzene ring or naphthalene ring, and X is a nuclear-substituted halogen atom or an alkyl or alkoxyl group having 3 or less carbon atoms,
m' and n'' are respectively 0, 1 or 2) diisocyanate (e.g. 4,4'-diphenylmethane diisocyanate, 2,2'-dimethyldiphenylmethane-4,4'-diisocyanate, diphenyldimethyl Methane-4,4'-diisocyanate, 3,
3'-dichlorodiphenyldimethylmethane-4,
4'-Diisocyanate): General formula (Here, X is a nuclear-substituted halogen atom or an alkyl or alkoxyl group having 3 or less carbon atoms, mâ³ is 0
or 1, n is 0, 1 or 2) (e.g. biphenyl-2,4'-diisocyanate, 3,3'-dimethylbiphenyl-4,
4'-diisocyanate, 3,3'-dimethoxybiphenyl-4,4'-diisocyanate): diphenylsulfone-4,4'-diisocyanate, benzene-1,2,4-triisocyanate, 2,4,
6-triisocyanate, 4,4',4''-triphenylmethane triisocyanate, 2,4,4'-triisocyanate diphenyl ether, polyisocyanate in which about 3 phenyl isocyanates are linked with a methylene bridge, Diisocyanates such as those obtained by hydrogenating the aromatic ring contained in the above isocyanates (e.g., dicyclohexane-4,4'-diisocyanate, Ï,Ï-diisocyanate-1,2-
Dimethylbenzene, Ï,Ïâ²-diisocyanate-1,3-dimethylbenzene): Diisocyanate containing substituted urea groups obtained by reaction of 2 mol of diisocyanate and 1 mol of water (e.g. 1 mol of water and 2 mol of water) Urea diisocyanate obtained by reaction with 2,4-toluylene diisocyanate): Uretdione diisocyanate obtained by bimolecular polymerization of aromatic diisocyanate by a known method. Incidentally, aliphatic polyisocyanates can also be used. Preferred blowing agents include halogenated lower hydrocarbons, examples of which include molar trichloromethane, difluorodichloromethane, monofluorodichloromethane, difluoromonochloromethane, difluorodibromemethane, and tetrafluorodichloroethane. , difluoropromethane, and the like. Examples of the foam stabilizer include conventionally known polydimethylsiloxanes, or so-called silicone oils such as compounds containing polydimethylsiloxane chains and polyoxyethylene chains. Catalysts that promote the reaction of the -NCO group include, for example, tertiary amine catalysts (e.g., N-dimethylpiperazine, endoethylenepiperazine, N-ethylmorpholine, triethylenediamine), tin catalysts (e.g., dibutyltin dilaurate, Dibutyltin diethylhexoate, stannous octoate,
stannous oleate), etc. Examples and comparative examples are listed below. In addition, all "parts" in each example represent "parts by weight", and the units of hydroxyl value and acid value are mgKOH/g.
It is. Production of polyhydroxyl compound 1 Example of esterification reaction production 1 4700 parts of poly(oxyethylene/oxypropylene) glycerol with a hydroxyl value of 36, 65 parts of itaconic acid, and 15 parts of paratoluenesulfonic acid were placed in a flask and heated at 170 to 180°C under nitrogen. The reaction was carried out at normal pressure for 10 hours and at the same temperature and 50 mmHg for 15 hours. product yield,
The analysis results are shown in Table-1. Production Examples 2 to 5, Comparative Production Examples 1 to 4 Products of Production Examples 2 to 5 and Comparative Production Examples 1 to 4 were obtained in the same manner as Production Example 1. Table 1 shows the results.
Shown below.
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å¿ããããåå¿æž©åºŠã¯70ã110âã«ä¿ã€ãã次ã
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ãã®ãã®ã®åæçµæè¡šãè¡šâïŒã«ç€ºãã[Table] 2 Vinyl monomer polymerization reaction production example 30 parts of the ester obtained in Production Example-1, 50 parts of poly(oxyethylene/oxypropylene) glycerol with a hydroxyl value of 35, 20 parts of styrene, benzoyl peroxide
0.5 part was charged into a flask and reacted at 80-120°C for 5 hours, followed by degassing at 100-120°C and below 10 mmHg for 1 hour. The resulting product was a homogeneous white emulsion. The analysis results are shown in Table-2. Manufacturing example~, Comparative manufacturing example~ Manufacturing example~, using the same method as Manufacturing example~,
, Comparative Preparation Example - The products of ~ were obtained. The results are shown in Table-2. Production example 50 parts of poly(oxyethylene/oxypropylene) glycerol with a hydroxyl value of 35 and 1.0 part of lauroyl peroxide were placed in a flask, and 30 parts of the ester obtained in Production Example-2 and 20 parts of styrene were added dropwise over 5 hours to react. Ta. The reaction temperature was kept at 70-110°C. Next, deaeration was performed at 100 to 110°C to obtain a uniform white emulsion. The analysis results of this product are shown in Table-2.
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ããããã·ã«ååç©ãçºæ³¡å€ãæŽæ³¡å€ã觊åªã容
åšã«ãšãããããŸãæ··åããŠãããæåãšãã
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蟌ã¿åå¿ã泡åãããçºæ³¡äœã補é ãããçµæã
è¡šâïŒã«ç€ºãã[Table] Production Examples 1 to 8 and Comparative Examples 1 to 2 of Polyurethane Materials Polyhydroxyl compounds and other polyhydroxyl compounds produced by Production Examples and Comparative Production Examples, blowing agents, foam stabilizers, Place the catalyst in a container, stir and mix to make this the A component,
A compound containing an isocyanate group was used as component B. Components A and B were rapidly mixed, charged into a mold, reacted, and foamed to produce a foam. The results are shown in Table-3.
ãè¡šããtableã
Claims (1)
ç©ãåå¿äž»æåãšããŠããªãŠã¬ã¿ã³ç©è³ªã補é ã
ãã«éããŠãããªããããã·ã«ååç©ã®å°ãªããš
ãäžæåãšããŠãããªãšãŒãã«ããªãªãŒã«ãšã€ã¿
ã³ã³é žã170âã230âã§åŠçããŠãšã¹ãã«åãšå
æã«ç±éåãç°æ§åãä»å åå¿ãè¡ãªã€ãŠåŸãã
ãããªãšã¹ãã«ã«ã©ãžã«ã«éåå¯èœãªããã«åé
äœãã°ã©ããéåãããŠåŸãããããªããããã·
ã«ååç©ãçšããããšãç¹åŸŽãšããããªãŠã¬ã¿ã³
ç©è³ªã®è£œé æ¹æ³ã1 When producing a polyurethane material using a polyisocyanate and a polyhydroxyl compound as the main reaction components, polyether polyol and itaconic acid are treated at 170°C to 230°C as at least one component of the polyhydroxyl compound to undergo thermal polymerization at the same time as esterification. A method for producing a polyurethane material, comprising using a polyhydroxyl compound obtained by graft polymerizing a radically polymerizable vinyl monomer to a polyester obtained by performing isomerization and addition reactions.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP58117901A JPS6011522A (en) | 1983-06-29 | 1983-06-29 | Production of polyurethane material |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP58117901A JPS6011522A (en) | 1983-06-29 | 1983-06-29 | Production of polyurethane material |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS6011522A JPS6011522A (en) | 1985-01-21 |
JPH0240245B2 true JPH0240245B2 (en) | 1990-09-11 |
Family
ID=14723003
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP58117901A Granted JPS6011522A (en) | 1983-06-29 | 1983-06-29 | Production of polyurethane material |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6011522A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0483916U (en) * | 1990-11-30 | 1992-07-21 |
-
1983
- 1983-06-29 JP JP58117901A patent/JPS6011522A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS6011522A (en) | 1985-01-21 |
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