JPH0469174B2 - - Google Patents
Info
- Publication number
- JPH0469174B2 JPH0469174B2 JP59038885A JP3888584A JPH0469174B2 JP H0469174 B2 JPH0469174 B2 JP H0469174B2 JP 59038885 A JP59038885 A JP 59038885A JP 3888584 A JP3888584 A JP 3888584A JP H0469174 B2 JPH0469174 B2 JP H0469174B2
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- polyol
- molecular weight
- vinyl
- polymers
- 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
- 229920000642 polymer Polymers 0.000 claims description 48
- 229920005862 polyol Polymers 0.000 claims description 41
- 150000003077 polyols Chemical class 0.000 claims description 41
- 239000000178 monomer Substances 0.000 claims description 21
- 239000007788 liquid Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- 238000004132 cross linking Methods 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 4
- 239000011952 anionic catalyst Substances 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 239000004721 Polyphenylene oxide Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229920000570 polyether Polymers 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- -1 cyanostyrene nitrostyrene Chemical compound 0.000 description 6
- 229920002635 polyurethane Polymers 0.000 description 6
- 239000004814 polyurethane Substances 0.000 description 6
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000000379 polymerizing effect Effects 0.000 description 5
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 5
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 239000005062 Polybutadiene Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- BFZOTKYPSZSDEV-UHFFFAOYSA-N 4-butan-2-yl-2,6-ditert-butylphenol Chemical compound CCC(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BFZOTKYPSZSDEV-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 2
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 2
- QWQNFXDYOCUEER-UHFFFAOYSA-N 2,3-ditert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1C(C)(C)C QWQNFXDYOCUEER-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- 229920002121 Hydroxyl-terminated polybutadiene Polymers 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 238000010420 art technique Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 239000011953 free-radical catalyst Substances 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000006069 physical mixture Substances 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- PDKAXHLOFWCWIH-UHFFFAOYSA-N 1,1-dichlorobuta-1,3-diene Chemical compound ClC(Cl)=CC=C PDKAXHLOFWCWIH-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
- UNMYKPSSIFZORM-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)butane Chemical compound CCCCOCCOC=C UNMYKPSSIFZORM-UHFFFAOYSA-N 0.000 description 1
- FPBWSPZHCJXUBL-UHFFFAOYSA-N 1-chloro-1-fluoroethene Chemical group FC(Cl)=C FPBWSPZHCJXUBL-UHFFFAOYSA-N 0.000 description 1
- GXZPMXGRNUXGHN-UHFFFAOYSA-N 1-ethenoxy-2-methoxyethane Chemical compound COCCOC=C GXZPMXGRNUXGHN-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 1
- OEVVKKAVYQFQNV-UHFFFAOYSA-N 1-ethenyl-2,4-dimethylbenzene Chemical compound CC1=CC=C(C=C)C(C)=C1 OEVVKKAVYQFQNV-UHFFFAOYSA-N 0.000 description 1
- UULPGUKSBAXNJN-UHFFFAOYSA-N 1-ethenyl-4-phenoxybenzene Chemical compound C1=CC(C=C)=CC=C1OC1=CC=CC=C1 UULPGUKSBAXNJN-UHFFFAOYSA-N 0.000 description 1
- KOCUMXQOUWPSLK-UHFFFAOYSA-N 1-methoxybuta-1,3-diene Chemical compound COC=CC=C KOCUMXQOUWPSLK-UHFFFAOYSA-N 0.000 description 1
- KUIZKZHDMPERHR-UHFFFAOYSA-N 1-phenylprop-2-en-1-one Chemical compound C=CC(=O)C1=CC=CC=C1 KUIZKZHDMPERHR-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- SXZSFWHOSHAKMN-UHFFFAOYSA-N 2,3,4,4',5-Pentachlorobiphenyl Chemical compound C1=CC(Cl)=CC=C1C1=CC(Cl)=C(Cl)C(Cl)=C1Cl SXZSFWHOSHAKMN-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- AQZABFSNDJQNDC-UHFFFAOYSA-N 2-[2,2-bis(dimethylamino)ethoxy]-1-n,1-n,1-n',1-n'-tetramethylethane-1,1-diamine Chemical compound CN(C)C(N(C)C)COCC(N(C)C)N(C)C AQZABFSNDJQNDC-UHFFFAOYSA-N 0.000 description 1
- BCYPDAYWIAJNIC-UHFFFAOYSA-N 2-but-3-en-2-yloxyethanethiol Chemical compound C=CC(C)OCCS BCYPDAYWIAJNIC-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 1
- MENUHMSZHZBYMK-UHFFFAOYSA-N 2-cyclohexylethenylbenzene Chemical compound C1CCCCC1C=CC1=CC=CC=C1 MENUHMSZHZBYMK-UHFFFAOYSA-N 0.000 description 1
- KBKNKFIRGXQLDB-UHFFFAOYSA-N 2-fluoroethenylbenzene Chemical compound FC=CC1=CC=CC=C1 KBKNKFIRGXQLDB-UHFFFAOYSA-N 0.000 description 1
- OZPOYKXYJOHGCW-UHFFFAOYSA-N 2-iodoethenylbenzene Chemical compound IC=CC1=CC=CC=C1 OZPOYKXYJOHGCW-UHFFFAOYSA-N 0.000 description 1
- BJUPZVQSAAGZJL-UHFFFAOYSA-N 2-methyloxirane;propane-1,2,3-triol Chemical compound CC1CO1.OCC(O)CO BJUPZVQSAAGZJL-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- HKADMMFLLPJEAG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-enylbenzene Chemical compound FC(F)(F)C=CC1=CC=CC=C1 HKADMMFLLPJEAG-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
- CEBRPXLXYCFYGU-UHFFFAOYSA-N 3-methylbut-1-enylbenzene Chemical compound CC(C)C=CC1=CC=CC=C1 CEBRPXLXYCFYGU-UHFFFAOYSA-N 0.000 description 1
- AIMDYNJRXHEXEL-UHFFFAOYSA-N 3-phenylprop-1-enylbenzene Chemical compound C=1C=CC=CC=1CC=CC1=CC=CC=C1 AIMDYNJRXHEXEL-UHFFFAOYSA-N 0.000 description 1
- ZMSQJSMSLXVTKN-UHFFFAOYSA-N 4-[2-(2-morpholin-4-ylethoxy)ethyl]morpholine Chemical compound C1COCCN1CCOCCN1CCOCC1 ZMSQJSMSLXVTKN-UHFFFAOYSA-N 0.000 description 1
- OIYTYGOUZOARSH-UHFFFAOYSA-N 4-methoxy-2-methylidene-4-oxobutanoic acid Chemical compound COC(=O)CC(=C)C(O)=O OIYTYGOUZOARSH-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-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
- YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical compound Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-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
- 230000032683 aging Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000011951 cationic catalyst Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 description 1
- 229960004419 dimethyl fumarate Drugs 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- NHOGGUYTANYCGQ-UHFFFAOYSA-N ethenoxybenzene Chemical compound C=COC1=CC=CC=C1 NHOGGUYTANYCGQ-UHFFFAOYSA-N 0.000 description 1
- XJELOQYISYPGDX-UHFFFAOYSA-N ethenyl 2-chloroacetate Chemical compound ClCC(=O)OC=C XJELOQYISYPGDX-UHFFFAOYSA-N 0.000 description 1
- AFIQVBFAKUPHOA-UHFFFAOYSA-N ethenyl 2-methoxyacetate Chemical compound COCC(=O)OC=C AFIQVBFAKUPHOA-UHFFFAOYSA-N 0.000 description 1
- FFYWKOUKJFCBAM-UHFFFAOYSA-N ethenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC=C FFYWKOUKJFCBAM-UHFFFAOYSA-N 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- GFJVXXWOPWLRNU-UHFFFAOYSA-N ethenyl formate Chemical compound C=COC=O GFJVXXWOPWLRNU-UHFFFAOYSA-N 0.000 description 1
- BLCTWBJQROOONQ-UHFFFAOYSA-N ethenyl prop-2-enoate Chemical compound C=COC(=O)C=C BLCTWBJQROOONQ-UHFFFAOYSA-N 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 description 1
- KETWBQOXTBGBBN-UHFFFAOYSA-N hex-1-enylbenzene Chemical compound CCCCC=CC1=CC=CC=C1 KETWBQOXTBGBBN-UHFFFAOYSA-N 0.000 description 1
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000007373 indentation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- AWJZTPWDQYFQPQ-UHFFFAOYSA-N methyl 2-chloroprop-2-enoate Chemical compound COC(=O)C(Cl)=C AWJZTPWDQYFQPQ-UHFFFAOYSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- SDYRIBONPHEWCT-UHFFFAOYSA-N n,n-dimethyl-2-phenylethenamine Chemical compound CN(C)C=CC1=CC=CC=C1 SDYRIBONPHEWCT-UHFFFAOYSA-N 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- VVZCVPJWQPOZJF-UHFFFAOYSA-N phenol;propane-1,2,3-triol Chemical compound OCC(O)CO.OC1=CC=CC=C1.OC1=CC=CC=C1 VVZCVPJWQPOZJF-UHFFFAOYSA-N 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Landscapes
- Processes Of Treating Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
Description
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The present invention relates to the production of polyols containing other polymers. The polyols of the present invention can be referred to as polymer polyols. Polyurethanes constitute a broad group of polymeric materials that have a wide range of physical properties. The polymer is produced by the interaction of a polyfunctional isocyanate with a polyfunctional chemical having active hydrogen within its structure, such as a polyester, polyether or a mixture of two or more such materials. . Conventionally, the materials used contain two or more hydroxyl groups and are therefore generally defined as polyols. It is known in the art that the physical properties of the resulting polyurethane composition can be improved to some extent by adding a high molecular weight polymer to the polyurethane composition. Significant efforts have been made to incorporate polymers into such polyurethane compositions. For example, U.S. Pat.
No. 3,383,351 discloses the in situ polymerization of ethylenically unsaturated monomers in the presence of the polyol component of a polyurethane composition. Prior art techniques include polymerizing ethylenically unsaturated monomers in the presence of an isocyanate-terminated prepolymer to form an isocyanate-terminated polymer prepolymer. This technology is described in U.S. Patent No.
No. 3,968,089 and the preparation of graft copolymer dispersions by in situ polymerization of vinyl monomers in the presence of polyols containing unsaturated bonds is also described, for example, in US Pat. No. 3,953,393. The present invention provides a method of forming polymers to achieve degrees of freedom not found in the prior art. According to the present invention, (a) an ethylenically unsaturated monomer is polymerized into a low molecular weight liquid polymer using an anionic catalyst in a selected medium; and (b) in a polyol different from the medium of step (a). A process for producing a polymer polyol is obtained, characterized in that the polymer from step (a) is mixed in step (a), and (c) the polymer is crosslinked in the polyol. The invention disclosed herein involves polymerizing monomers in a selected medium, stopping the polymerization at a selected time, and
This relatively low molecular weight polymer is then dispersed in a polyol and the polymer is then crosslinked to the desired level. By this method the microstructure of the initial polymer can be controlled by known techniques, including judicious selection of the medium along with the selection of initiators for the first stage polymerization. This pre-produced low molecular weight polymer is then
It is dispersed in a polyol and crosslinked to an appropriate level while retaining its internal structural properties.
Prior art techniques for polymerizing monomers in polyols are unable to incorporate such treatments into the polymer portion of the polymer polyol. Monomers useful in the practice of this invention are polymerizable ethylenically unsaturated monomers containing at least one polymerizable ethylene group. The monomers may be used singly to produce homopolymers/polyols or in combination to produce copolymers/polyols. These monomers are known and include butadiene, isoprene, 1,4-pentadiene, 1,
Hydrocarbon monomers such as 6-hexadiene, 1,7-octadiene, styrene, α-methylstyrene, 2,4-dimethylstyrene, ethylstyrene, isopropylstyrene, butylstyrene, phenylstyrene, cyclohexylstyrene and benzylstyrene; chloro Styrene, 2,5-dichlorostyrene, bromostyrene, fluorostyrene, trifluoromethylstyrene, iodostyrene, cyanostyrene nitrostyrene, N,N-
Substituted styrenes such as dimethylaminostyrene, p-vinyldiphenyl sulfide and p-vinylphenyl phenyl oxide; methyl acrylate, methyl methacrylate, cyclohexyl methacrylate, benzyl methacrylate, isopropyl methacrylate, octyl methacrylate,
Methacrylonitrile, methyl α-chloroacrylate, ethyl α-ethoxy acrylate, methyl α-acetaminoacrylate, butyl acrylate, 2-ethylhexyl acrylate,
Acrylic and substituted acrylic monomers such as phenyl acrylate, phenyl methacrylate and α-chloroacrylonitrile; vinyl acetate, vinyl chloroacetate, vinyl butyrate, isopropenyl acetate, vinyl formate, vinyl acrylate, vinyl methacrylate, vinyl methoxy acetate, Vinyl benzoate, vinyl naphthalene, vinyl bromide, vinyl fluoride, vinylidene bromide, 1-chloro-1-fluoro-ethylene, vinylidene fluoride, vinyl methyl ether, vinyl ethyl ether, vinyl propyl ether, vinyl butyl ether, vinyl 2-ethylhexyl ether , vinyl phenyl ether, vinyl 2-methoxyethyl ether, methoxybutadiene, vinyl 2-butoxyethyl ether, 3,4-dihydro-1,2
- vinyl esters and vinyl ethers such as pyran, 2-butoxy-2'-vinyloxy diethyl ether, vinyl 2-ethyl mercaptoethyl ether, vinyl methyl ketone, vinyl ethyl ketone and vinyl phenyl ketone; dimethyl fumarate, dimethyl maleate , monomethyl itaconate, dimethylaminoethyl methacrylate, glycidyl acrylate, dichlorobutadiene, vinylpyridine, and hydroxyethyl methacrylate. The compounds described above are illustrative and not limiting of suitable monomers for use in the present invention. Preferred ethylenically unsaturated monomers for the practice of this invention include hydrocarbon monomers such as butadiene, isoprene, styrene and alpha-methylstyrene and isocyanate groups such as methyl acrylate, methyl methacrylate, hydroxyethyl methacrylate, acrylonitrile and methacrylonitrile. Examples include acrylic monomers and substituted acrylic monomers that do not react with. The first stage polymerization or copolymerization of these monomers to produce low molecular weight liquids is accomplished by a variety of known techniques. These low molecular weight polymers should generally have a molecular weight of 1800-8000. One skilled in the art can select the polymerization method to obtain the desired microstructure for the polymer. Free radical and cationic catalysts give highly branched polymers, while anionic and Zieglev-Natta catalysts give products with a linear structure. Preferred low molecular weight polymers are obtained by anionic polymerization or copolymerization of ethylenically unsaturated monomers, most preferably butadiene. Such polymers include Revertex Ltd., Temple Fields, Harlow, Essex, UK;
LITHENE liquid polymer of butadiene manufactured by Harlow Essex, Great Britain). These preferred LITHENEs are prepared by anionic polymerization of butadiene, as described in the product data. An organolithium catalyst is used in a solvent. Although toluene is listed as a common solvent, it is only one of many solvents that can be used. Butadiene monomer (CH 2 = CHâ
Anionic polymerization of CH=CH 2 ) gives three different types of structures.
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ïŒAccuratioïŒæ©ãçšããŠè£œé ãããã1,4- 1,2- Cyclization By adjusting these structures by known methods, the overall microstructure of the polymer can be adjusted. For this reason, the person skilled in the art can then select the type of polymer that he wishes to further crosslink in the polyol. Other types of low molecular weight liquid polymers preferred for crosslinking in polyols include those terminated with hydroxy groups having internal unsaturation and having molecular weights from 1800 to 8000. for example,
Such polybutadiene and butadiene-ethylene copolymers are available from ARCO chemical CO., a division of Atlantic Richfield, Inc.
Poly bd Liquid Resine (trade name) manufactured by Richfield Co., Ltd. has the following published structure. homopolymer (In the formula, n is 50) Copolymer HO [(---CH 2 -CH=CH-CH 2 ) a - (CH 2 -CH 2 ) b ]
--- o OH where a is 0.75, b is 0.25 and n is 54 These polymers are proposed to be used as suitable components to react with polyisocyanates to form polyurethanes. There is. In the present invention, these hydroxyl-terminated polymers are suitable for crosslinking in polyols, just like the non-hydroxyl-terminated polymers mentioned above. The same group of monomers that are useful for polymerizing non-hydroxy-terminated polymers are useful for polymerizing to obtain hydroxy-terminated polymers. Methods for producing these substances are known. Polyether polyol components useful in the preparation of polymer polyol compositions have a functionality of 2 to 6 and have a functionality of 2,000 to 10,000, preferably 2,000
Mention may be made of polyols with a molecular weight of ~7000. These polyether polyols include trimethylolpropane, glycerol, 1,2,6-
Well-known processes involving the reaction of polyvalent initiators such as hexanetriol, sorbitol or pentaerythritol with alkylene oxides such as ethylene oxide, propylene oxide, butylene oxide, or mixtures of ethylene oxide and propylene oxide and/or butylene oxide. Manufactured by. This reaction is carried out by well known methods using an alkoxylation catalyst, typically an alkali metal hydroxide, such as potassium hydroxide. The alkoxylation reaction is continued until the product reaches the desired molecular weight. Particularly preferred polyether polyols are polyether triols. Preferred polyether diols are, for example, polypropylene glycols or mixed polypropylene glycol/polyethylene glycol copolymers with a molecular weight of 2000 to 5000. These materials are produced by reacting ethylene oxide, propylene oxide or butylene oxide either sequentially or in admixture with initiators such as ethylene glycol, propylene glycol or butylene glycol. Another preferred polyol is one produced by impregnating the inside of a polyol with an epoxy resin. These polyols are described, for example, in US Pat. No. 4,316,991. The polyether polyol and the pre-prepared low molecular weight liquid polymer are mixed or dispersed together and then further crosslinked, for example by a catalyst such as a free radical catalyst or an azo compound. This crosslinking technique is generally performed under the following conditions. Usually, crosslinking of the pre-prepared liquid polymer takes place at a temperature of 100-150°C, preferably 110-140°C. Crosslinking may proceed under atmospheric or sub-atmospheric conditions. The following non-limiting examples illustrate the implementation of the invention. Example 1 Into a three-necked flask equipped with a stirrer, thermometer, condenser, and nitrogen supply port, a sample having a molecular weight of 5500
Propylene oxide/ethylene oxide (PO/EO) adduct of glycerol (THANOL SF-5505)
320 g, 80 g of butadiene liquid polymer having a molecular weight of 5000 (LITHENE N4-5000) and 4.0 g of 2,5-dimethyl-2,5-di(t-butylperoxy)hexane (LUPERSOL 101: trade name) were charged. The reaction mixture was heated at 125-135° C. for 5 hours while maintaining a nitrogen purge. The product was then stabilized with 1.3 g of 2,6-di-t-butyl-4-sec-butylphenol (ISONOX 132). The final product was a white, opaque, viscous liquid with the following characteristics: This polymer polyol was stable in glass for 3 months. Acid number (mg KOH/g) 0.015 Hydroxyl number (mg KOH/g) 32.6 Moisture (wt%) 0.01 PH (10:6 isopropanol/water) 6.8 Viscosity at 25°C (cps) 3720 The physical mixture of the above reactants is Initial viscosity is 25â
It was 1800 cps and separated into phases within a few days. Example 2 This example shows the production according to Example 1 in a scaled-up manner. THANOL SF for 30 reactors
â5505 polyol 3.63Kg, LITHENE N4â5000
0.91Kg and LUPERSOL 101 45.4g were input.
The reactor was then evacuated and purged with prepurified nitrogen. It was then heated at 128-130°C for 3 hours. The reaction was monitored by measuring the viscosity every hour. The results are shown below. Time (hours) Viscosity 25°C (cps) 0 1860 1 2100 2 2100 3 2340 The product was then stabilized with 6.8 g of di-t-butyl-p-cresol. According to GPC, the product was 10% of the polymer with 2-3 times the molecular weight of the starting material on the chromatogram. Example 3 This example describes the steps in the production of RIM elastomer.
Figure 2 illustrates the use of the polybutadiene polymer polyol of Example 2. Additionally, this example also demonstrates the improved hydrolytic stability and heat sag properties of elastomers made using these materials. These elastomers were manufactured using an Accuratio machine.
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žåãšãã¬ã³ïŒTHANOL â
3016ïŒåã³å®æœäŸïŒã®ããŒã¹ããªãªãŒã«ãã補é
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èè·éæ§ã¯ãã€ãã€ãã³ïŒChatillonïŒã²ãŒãžã
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äžã«ç€ºãã[Table] 1: PO/EO adduct of glycerin with a molecular weight of 5500:
Texaco Chemical Company 2: Obtained from Example 1 3: 80:20 EO/PO diol with molecular weight 11000:
BASF (Wyandotte) 4: Dimethylaminoethanol: Texaco Chemical Co. 5: SUL-4 (product name): Witco Chemical Co. 6: Thioorganotin compound: Witco Chemical Co. 7: Liquid MDI: Upjohn Chemical Co. 8: Isocyanate-rich pseudoprepolymer:
THANATE L-55-O (trade name): Texaco Chemical Company Example 4 This example demonstrates the use of a polybutadiene polymer polyol (prepared in Example 1) in the production of a high resiliency (HR) foam. Furthermore, this example shows that the foam has good properties throughout. The blending ratio, manufacturing details, and characteristics are shown below. Blending ratio, weight part A THANOL SF-5505 60 Polybutadiene polymer polyol 40 Water 2.8 Q2-5043 Silicone 1 2.0 THANCAT TD-33 2 0.25 NIAX A-1 3 0.25 THANCAT DM-70 4 0.25 Dibutyltin dilaurate 0.01 80:20TDI/PAPI 5 35.1 Isocyanate Index 1.02 Manufacturing Details Cream Time (sec) 6 Rise Time (sec) 120 Gel Time (sec) 195 Characteristic Density (g/ cm3 ) 0.038 Tensile Strength (MPa) 0.092 Elongation (%) 119 Tear Strength (N/m) 2.28 Compression set 50% 21.1 95% 18.2 Wet aging (5 hours at 121°C) Compression set (%) 22.1 CLD loss, 50% 6 9.99 1: Dow Corning
Corp. 2: 33% triethylene diamine in propylene glycol: Texaco Chemical Co. 3: Bis-dimethylaminoethyl ether: Union Carbide Chemical Co. 4: 70% dimorpholino diethyl ether/30%
N,N'-dimethylpiperazine: Texaco
Chemical Co. 5: High molecular weight isocyanate with functionality of 2.7: Mobay Chemical Co.
Product 6: Compressive Load Deflection Example 5 This example demonstrates the polymerization of a hydroxyl terminated polybutadiene liquid polymer in THANCL SF-5505 polyol. THANOL was added to a three-necked flask equipped with a stirrer, thermometer, condenser, and nitrogen inlet.
SF-5505 polyol 400g, hydroxy-terminated polybutadiene liquid polymer [poly bd
R-45M (trade name), ARCO Chemical Co.] 100g and
5.0 g of LUPERSOL 101 (trade name) was added. At this point, the reaction had a viscosity of 1340 cps at 25°C. The reaction mixture was heated at 128-135° C. for 4.75 hours while maintaining a nitrogen purge. The reaction mixture was then cooled and stabilized with 0.5 g of ISONOX 132. The final product was a white, opaque, viscous liquid with the following characteristics: Acid number (mg KOH/g) 0.13 Hydroxyl number (mg KOH/g) 36.6 Moisture (wt%) 0.01 Viscosity at 25°C (cps) 6300 Peroxide (ppm) 1.95 Example 6 Stirrer, thermometer, condenser and nitrogen In a three-necked flask equipped with a feed port, add a propylene oxide/ethylene oxide/diglycidyl ether adduct of glycerol bisphenol A with a molecular weight of 3500.
400 g, 100 g of butadiene liquid polymer with a molecular weight of 5000 (LITHENE N4 5000) and
5.0g of LUPERSOL101 was added. The reaction mixture was heated at 125-135° C. for 3 hours while maintaining a nitrogen purge. The product was then stabilized with 0.75 g of di-t-butyl-p-cresol. The final product was a white, opaque, viscous liquid with the following characteristics: Hydroxyl Number (mg KOH/g) 42.3 Viscosity, 25°C (cps) 1538 The physical mixture of the above reactants has a viscosity of 1275 cps at 25°C.
It had a viscosity of Example 7 This example demonstrates the use of the polymer polyol of Example 9 in the production of flexible foams. Furthermore, this example shows that glycerol propylene oxide/ethylene oxide (THANOL F-
3016) and the base polyol of Example 6, foams made from this polyol show improved load carrying capacity.
Load carrying capacity was measured using a Chatillon gauge (indentation: 33%). The blending ratio, manufacturing details, and foam characteristics are shown below.
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ãã³ïŒãããµã³ã»ã±ãã«ã«ç€Ÿã®è£œå
ïŒïŒãžãšã³ã»ãã€ãã€ãã³ïŒJohn ChatillonïŒå
ã³ãµã³ãºïŒSonsïŒã«ãã補é ããããããŠã¢
ã«ã»ã¢ãã«ã»ãšã«ã»ã¢ã€ã»ã·ã€ïŒManual
Model LICïŒå§çž®è©Šéšæ©[Table] 1: Union Carbide Co. product 2: Triethylenediamine in propylene glycol: Texaco Chemical Co. product 3: Manual model L manufactured by John Chatillon and Sonsã»Iã»C (Manual
Model LIC) Compression testing machine
Claims (1)
ãšãã¬ã³æ§äžé£œåã¢ãããŒãéåããŠäœååé
液ç¶ããªããŒãšãªãã (b) å·¥çš(a)ã®åªäœãšã¯ç°ãªãããªãªãŒã«äžã§å·¥çš
(a)ããã®ããªããŒãæ··åãã (c) åèšããªãªãŒã«äžã§åèšããªããŒãæ¶æ©ãã
ããã ããšãç¹åŸŽãšããããªããŒããªãªãŒã«ã®è£œé æ¹
æ³ã ïŒ å·¥çš(a)ããã®ããªããŒã®ååéã1800ä¹è³
8000ã§ããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé èšèŒã®æ¹æ³ã ïŒ å·¥çš(b)ã®ããªãªãŒã«ã¯2000ä¹è³7000ã®ç¯å²ã®
ååéãæããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé èšèŒã®æ¹
æ³ãClaims: 1. (a) polymerization of ethylenically unsaturated monomers into a low molecular weight liquid polymer using an anionic catalyst in a selected medium; (b) a polyol different from the medium of step (a); process inside
A method for producing a polymer polyol, comprising: (a) mixing the polymers; and (c) crosslinking the polymers in the polyol. 2 The molecular weight of the polymer from step (a) is 1800 to
8000, the method of claim 1. 3. The method according to claim 2, wherein the polyol in step (b) has a molecular weight in the range of 2,000 to 7,000.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US47234183A | 1983-03-04 | 1983-03-04 | |
US472344 | 1983-03-04 | ||
US472341 | 1983-03-04 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS59168021A JPS59168021A (en) | 1984-09-21 |
JPH0469174B2 true JPH0469174B2 (en) | 1992-11-05 |
Family
ID=23875125
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP59038885A Granted JPS59168021A (en) | 1983-03-04 | 1984-03-02 | Manufacture of composition containing free isocyanate group or free hydroxy group for making polyisocyanate |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS59168021A (en) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5439440A (en) * | 1977-09-02 | 1979-03-26 | Toyoda Gosei Co Ltd | Coating composition |
JPS57123212A (en) * | 1980-12-10 | 1982-07-31 | Union Carbide Corp | Polymer/polyisocyanate composition, manufacture and manufacture of polyurethane products |
-
1984
- 1984-03-02 JP JP59038885A patent/JPS59168021A/en active Granted
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5439440A (en) * | 1977-09-02 | 1979-03-26 | Toyoda Gosei Co Ltd | Coating composition |
JPS57123212A (en) * | 1980-12-10 | 1982-07-31 | Union Carbide Corp | Polymer/polyisocyanate composition, manufacture and manufacture of polyurethane products |
Also Published As
Publication number | Publication date |
---|---|
JPS59168021A (en) | 1984-09-21 |
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