TWI526463B - Polyurethane resin - Google Patents
Polyurethane resin Download PDFInfo
- Publication number
- TWI526463B TWI526463B TW100108738A TW100108738A TWI526463B TW I526463 B TWI526463 B TW I526463B TW 100108738 A TW100108738 A TW 100108738A TW 100108738 A TW100108738 A TW 100108738A TW I526463 B TWI526463 B TW I526463B
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- weight
- polyurethane resin
- polyol
- mixture
- Prior art date
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- 229920005749 polyurethane resin Polymers 0.000 title claims description 49
- 239000000203 mixture Substances 0.000 claims description 42
- 229920005862 polyol Polymers 0.000 claims description 31
- -1 polyoxypropylene propylene glycol Polymers 0.000 claims description 30
- 150000003077 polyols Chemical class 0.000 claims description 28
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 239000005056 polyisocyanate Substances 0.000 claims description 16
- 229920001228 polyisocyanate Polymers 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 7
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- 229920005903 polyol mixture Polymers 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 description 13
- 230000000704 physical effect Effects 0.000 description 11
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 150000002430 hydrocarbons Chemical group 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- 230000035882 stress Effects 0.000 description 6
- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 229910000019 calcium carbonate Inorganic materials 0.000 description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000004014 plasticizer Substances 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 4
- KTGXWDZUZLWXOF-UHFFFAOYSA-N NCCNCCCC(C(OC)(OC)C)CCCCCCCC Chemical compound NCCNCCCC(C(OC)(OC)C)CCCCCCCC KTGXWDZUZLWXOF-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- AIMIUEPYQVMFAS-UHFFFAOYSA-N azane;ethanamine Chemical compound N.CCN AIMIUEPYQVMFAS-UHFFFAOYSA-N 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000013065 commercial product Substances 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920005906 polyester polyol Polymers 0.000 description 3
- 239000004848 polyfunctional curative Substances 0.000 description 3
- 238000004321 preservation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 102100035474 DNA polymerase kappa Human genes 0.000 description 2
- 101710108091 DNA polymerase kappa Proteins 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- QZLZITSAKXSAMC-UHFFFAOYSA-N NCCCC(C(OC)(OC)C)CCCCCCCC Chemical compound NCCCC(C(OC)(OC)C)CCCCCCCC QZLZITSAKXSAMC-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 238000012644 addition polymerization Methods 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- CWZQYRJRRHYJOI-UHFFFAOYSA-N 1,1,1-trimethoxydecane Chemical compound CCCCCCCCCC(OC)(OC)OC CWZQYRJRRHYJOI-UHFFFAOYSA-N 0.000 description 1
- GDDPLWAEEWIQKZ-UHFFFAOYSA-N 1,1-diethoxydecane Chemical compound CCCCCCCCCC(OCC)OCC GDDPLWAEEWIQKZ-UHFFFAOYSA-N 0.000 description 1
- HIZVCIIORGCREW-UHFFFAOYSA-N 1,4-dioxene Chemical compound C1COC=CO1 HIZVCIIORGCREW-UHFFFAOYSA-N 0.000 description 1
- QGLRLXLDMZCFBP-UHFFFAOYSA-N 1,6-diisocyanato-2,4,4-trimethylhexane Chemical compound O=C=NCC(C)CC(C)(C)CCN=C=O QGLRLXLDMZCFBP-UHFFFAOYSA-N 0.000 description 1
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-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
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- LBIHNTAFJVHBLJ-UHFFFAOYSA-N 3-(triethoxymethyl)undec-1-ene Chemical compound C(=C)C(C(OCC)(OCC)OCC)CCCCCCCC LBIHNTAFJVHBLJ-UHFFFAOYSA-N 0.000 description 1
- GSNKRSKIWFBWEG-UHFFFAOYSA-N 3-ethylpentan-2-one Chemical compound CCC(CC)C(C)=O GSNKRSKIWFBWEG-UHFFFAOYSA-N 0.000 description 1
- QJIVRICYWXNTKE-UHFFFAOYSA-N 4-(8-methylnonoxy)-4-oxobutanoic acid Chemical compound CC(C)CCCCCCCOC(=O)CCC(O)=O QJIVRICYWXNTKE-UHFFFAOYSA-N 0.000 description 1
- GJNKQJAJXSUJBO-UHFFFAOYSA-N 9,10-diethoxyanthracene Chemical compound C1=CC=C2C(OCC)=C(C=CC=C3)C3=C(OCC)C2=C1 GJNKQJAJXSUJBO-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- JZHKIUBMQMDQRG-UHFFFAOYSA-N C(=C)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C(=C)C(C(OC)(OC)OC)CCCCCCCC JZHKIUBMQMDQRG-UHFFFAOYSA-N 0.000 description 1
- VPLKXGORNUYFBO-UHFFFAOYSA-N C1(CC2C(CC1)O2)CCC(C(OC)(OC)OC)CCCCCCCC Chemical compound C1(CC2C(CC1)O2)CCC(C(OC)(OC)OC)CCCCCCCC VPLKXGORNUYFBO-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- MLGYDIXISVOZKC-UHFFFAOYSA-N NCCNCCCC(C(OC)(OC)OC)(CCCCCCCC)C Chemical compound NCCNCCCC(C(OC)(OC)OC)(CCCCCCCC)C MLGYDIXISVOZKC-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 241000981595 Zoysia japonica Species 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
- NBJODVYWAQLZOC-UHFFFAOYSA-L [dibutyl(octanoyloxy)stannyl] octanoate Chemical compound CCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCC NBJODVYWAQLZOC-UHFFFAOYSA-L 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- BPSLVNCMKDXZPC-UHFFFAOYSA-N benzyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC1=CC=CC=C1 BPSLVNCMKDXZPC-UHFFFAOYSA-N 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- WVNYVWLYZRSLJZ-UHFFFAOYSA-H butyltin(3+);phthalate Chemical compound CCCC[Sn+3].CCCC[Sn+3].[O-]C(=O)C1=CC=CC=C1C([O-])=O.[O-]C(=O)C1=CC=CC=C1C([O-])=O.[O-]C(=O)C1=CC=CC=C1C([O-])=O WVNYVWLYZRSLJZ-UHFFFAOYSA-H 0.000 description 1
- UZYXHGXBGFRTHX-UHFFFAOYSA-N calcium;octanoic acid Chemical compound [Ca].CCCCCCCC(O)=O UZYXHGXBGFRTHX-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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Classifications
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- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
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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
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- 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
- C08G18/48—Polyethers
- C08G18/4825—Polyethers containing two hydroxy groups
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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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
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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
- C08G2190/00—Compositions for sealing or packing joints
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- Chemical & Material Sciences (AREA)
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- Polyurethanes Or Polyureas (AREA)
Description
本專利申請案，係主張日本專利申請案第2010-60779號(申請日2010年3月17日)之優先權，在此以參照方式，將該申請案全文併入本說明書中。
本發明係有關於聚胺基甲酸酯樹脂及其製造方法，詳言之，該樹脂係為適於使用在具有低模數高伸張之物性的硬化性組成物、且具有優良的接著性、物性、加工性及儲存安定性的無溶劑型聚胺基甲酸酯樹脂。
在習知上，由末端加成分子內具胺基之矽烷化合物的胺基甲酸酯預聚物所製成之聚胺基甲酸酯，由於在分子鏈內有胺基甲酸酯鏈結及尿素鏈結，因此具有優良的物性，如延伸性及強韌性(專利文獻1和2)。然而，上述的聚胺基甲酸酯，會因為預聚物中殘留的2級胺基而使預聚物呈鹼性，導致烷氧矽基進行加水分解，遂而有發生膠化或增黏、保存安定性不足等問題。
為此，作為除去呈鹼性之胺基的方法，有人提出可將含有胺基的矽烷化合物加成至α-β-不飽和羰基作成烷氧基矽烷化合物，再將其加成至胺基甲酸酯預聚物的方法(專利文獻3)。但是，在以上述方法製造低模數高伸張的聚胺基甲酸酯樹脂時，會造成該聚胺基甲酸酯樹脂高黏度化及加工性惡化，且該製程既複雜成本亦高昂。
專利文獻1：特開平03-047825號
專利文獻2：特開平03-157424號
專利文獻3：特開平2000-169544號
本發明之課題係提供一種無溶劑型聚胺基甲酸酯樹脂，其適於使用在硬化後物性為低模數高伸張之硬化性組成物，且具有良好的接著性、物性、加工性及保存安定性；以及提供簡便且低廉地製造該聚胺基甲酸酯樹脂的方法。
本發明人等發現，將平均末端羥基數為1.3~2.1之單元醇和多元醇的混合物與聚異氰酸酯反應所得之胺基甲酸酯預聚物，與分子內有交聯性矽烷基及胺基的化合物相互反應，最後得到的聚胺基甲酸酯樹脂即能解述上述課題，遂而完成本發明。
亦即，本發明包括以下之較佳實施態樣。
[1] 一種聚胺基甲酸酯樹脂，其係藉由使(1)胺基甲酸酯預聚物及(2)以下述(式1)表示之化合物反應而得者：(1)胺基甲酸酯預聚物，其由(a)平均末端羥基數為1.3~2.1的單元醇和多元醇之混合物，與(b)聚異氰酸酯反應而成；以及
(2)如下列(式1)所示，具有分子內交聯性矽烷基與亞胺基及胺基的化合物：
(R1O)n-SiR3-n-R2-NH-R3-NH2 (式1)
(式中，R表示甲基或乙基，R1表示甲基或乙基，R2表示碳數2~10之烴基，R3表示碳數2~10之烴基)
[2]如[1]所述之聚胺基甲酸酯樹脂，其中多元醇的數量平均分子量(Mn)為500~30000。
[3]如[1]或[2]所述之聚胺基甲酸酯樹脂，其中多元醇係聚氧伸丙基二醇。
[4]如[1]~[3]所述之聚胺基甲酸酯樹脂，其中單元醇和多元醇之混合物(a)及聚異氰酸酯(b)之反應係於NCO/OH之當量比為1.6~2.5的範圍內進行。
[5]如[1]~[4]所述之聚胺基甲酸酯樹脂，其中前述預聚物與(式1)所示化合物之反應，係於NCO/NH2之當量比為0.6~1.2的範圍內進行。
[6]聚胺基甲酸酯樹脂之製造方法，其特徵為使以下物質發生反應：(1)胺基甲酸酯預聚物，其由(a)平均末端羥基數為1.3~2.1的單元醇和多元醇之混合物，與(b)聚異氰酸酯反應而成；以及
(2)如下列(式1)所示，具有分子內交聯性矽烷基與亞胺基及胺基的化合物：
(R1O)n-SiR3-n-R2-NH-R3-NH2 (式1)
(式中，R表示甲基或乙基，R1表示甲基或乙基，R2表示碳數2~10之烴基，R3表示碳數2~10之烴基)。
本發明之聚胺基甲酸酯樹脂，具有優良的接著性、物性、加工性及保存安定性，因此可適於作為接著劑而使用之。其次，該聚胺基甲酸酯樹脂具有低黏度，因此適於作為不含溶劑之接著劑而使用之。再者，依據本發明之製造方法，並不需要將胺基去活性之製程，因此可低廉且簡單地製造前述之聚胺基甲酸酯樹脂。
以下說明本發明之實施態樣。
本發明係一種聚胺基甲酸酯樹脂，其係藉由使(1)胺基甲酸酯預聚物及(2)以下述(式1)表示之化合物反應而得者：(1)胺基甲酸酯預聚物，其由(a)平均末端羥基數為1.3~2.1的單元醇和多元醇之混合物，與(b)聚異氰酸酯反應而成；以及
(2)如下列(式1)所示，具有分子內交聯性矽烷基與亞胺基及胺基的化合物：
(R1O)n-SiR3-n-R2-NH-R3-NH2 (式1)
(式中，R表示甲基或乙基，R1表示甲基或乙基，R2表示碳數2~10之烴基，R3表示碳數2~10之烴基)。
本發明之聚胺基甲酸酯樹脂，由於該單元醇與多元醇之混合物(a)的平均末端羥基數為1.3~2.1，因而呈現優良的物性及安定性。
在本發明中，平均末端羥基之測定係依循JIS K 1667-1:2007之規範。
在本發明中，前述單元醇與多元醇之混合物(a)，從物性及安定性之觀點出發，若以該混合物(a)的總重為基準，則單元醇以20重量%~80重量%較佳，35重量%~65重量%更佳；多元醇以20重量%~80重量%較佳，35重量%~65重量%更佳，將兩者依比例混合即可得之。
前述之單元醇，舉例而言可為聚氧伸烷基單醇、聚酯型單醇、聚醚‧酯化單醇、高級飽和單醇、具有乙烯性不飽和雙鍵之單元醇等，且係其等之一種或2種以上之混合物均可。
前述之聚氧伸烷基單醇，舉例而言可為分子内含一個羥基的高分子量聚氧伸烷基系單醇，其係以含有1個活性氫之烷類化合物等為起始劑，將環氧乙烷、環氧丙烷、環氧丁烷、四氫呋喃等環氧烷類開環加成聚合而成者。
前述之聚酯型單醇，舉例而言可為：習知之聚酯型多醇之末端羥基經烷化的改質物；以單羥化合物為起始劑，對環狀內酯進行開環加成聚合反應或酯化反應而成的內酯系聚酯型單醇；從多價醇類以及飽和脂肪酸或具乙烯性不飽和雙鍵的羧酸(如(甲基)丙烯酸、桂皮酸、或為碳數10以上高級不飽和脂肪酸如油酸、亞麻油酸、次亞麻油酸等)而得之酯化單醇等。
前述之聚醚‧酯化單醇，係如將前述之(單)環氧烷類以脂肪酸酯單醇加成聚合而成之聚氧伸烷基脂肪酸酯單醇等。
尤其若由通用性及安全性的觀點出發，則以聚氧伸烷基單醇，特別是聚氧伸丙烷基單醇較佳。
前述之單醇以市售品為例，係如旭硝子公司製造的PML-S1006等商品。
前述之多元醇，舉而言之，例如將乙二醇、丙二醇、甘油、三羥甲基丙烷、季戊四醇、山梨醇、乳糖等多價醇類，以環氧丙烷、或環氧丙烷與環氧乙烷等環氧烷類加成聚合而成之聚醚多醇類；乙二醇、丙二醇及其等之二醇寡聚物類；丁二醇、己二醇、聚四氫呋喃類；聚己內酯多元醇類；如聚伸乙基己二酸酯之聚酯多醇類；聚丁二烯醚多醇類；如蓖麻油之具有羥基的高級脂肪酸酯類；以乙烯基單體將聚醚多醇類或聚酯多醇類接枝化而成的聚合物多醇類等，亦可使用其等之1種或2種以上的混合物。
前述之多元醇，若以可加工性、硬化性及物性的觀點出發，則以環氧丙烷、抑或是環氧丙烷及環氧乙烷之加成物的聚氧伸烷基多醇較佳。尤其，前述的多元醇，使用環氧丙烷之加成物，即聚氧伸丙基多醇，尤其是聚氧伸丙基二醇，在實用上較佳。
該等多元醇，可由習知方法製得，具體上可由日本專利特許第3076032號公報所記載的方法例示之。
前述之聚氧伸烷基多醇以市售品為例，係如旭硝子公司製PML-4011F和PML-4013F等。
於本發明中，前述單醇的數量平均分子量(Mn)，從其成本或黏度的觀點出發，係500以上較佳，而1,000以上更佳。又，前述單醇的數量平均分子量(Mn)，從所得聚胺基甲酸酯樹脂之黏度的觀點出發，係25,000以下較佳，而10,000以下更佳。
前述之多元醇的數量平均分子量(Mn)，從所得聚胺基甲酸酯樹脂之物性的觀點出發，係500以上較佳，而1,000以上更佳。其次，前述單醇的數量平均分子量(Mn)，從所得聚胺基甲酸酯樹脂之黏度的觀點出發，係30,000以下較佳，而20,000以下更佳。
在此，本發明的數量平均分子量(Mn)及重量平均分子量(Mw)，係以凝膠滲透層析法(GPC)測定的聚苯乙烯換算值。
其次，於本發明中，令聚異氰酸鹽(或酯)(b)與上述單元醇及多元醇之混合物(a)發生反應。
前述之聚異氰酸酯，舉例而言有芳香族聚異氰酸酯(二異氰酸甲苯酯、4-4'-二苯基甲烷二異氰酸酯、苯二甲基二異氰酸酯、聯甲苯胺二異氰酸酯等)、脂環族聚異氰酸酯(二環己基甲烷二異氰酸酯、異佛酮二異氰酸酯、亞異丙基雙(4-異氰酸環己酯)、氫化苯二甲基二異氰酸酯、環己基二異氰酸酯、異佛酮二異氰酸酯等)、脂肪族聚二異氰酸酯(六亞甲基二異氰酸酯、離胺酸二異氰酸酯、2,2,4及2,4,4-三甲基六亞甲基二異氰酸酯等)。
前述之聚異氰酸酯以市售品為例，係如拜耳公司製Desmodur I(IPDI)、Desmodur H(HDI)等商品。
於本發明中，係令單元醇及多元醇之混合物(a)與聚異氰酸酯(b)呈NCO/OH當量比1.6~2.5下反應較佳，而1.8~2.2更佳。前述令混合物(a)與聚異氰酸酯(b)於該範圍內反應者，係有利於聚胺基甲酸酯樹脂的物性及安定性。
該反應，若有必要，可在適當的反應觸媒(例如，二月桂酸二丁基錫等有機錫系觸媒、辛酸鉍等鉍系觸媒、1,4-二吖[2,2,2]雙環辛烷等三級胺系觸媒)的存在下，一般而言，以常溫~90℃(例如60~90℃)1~48小時的條件下進行之。
前述胺基甲酸酯預聚物(1)，係末端含異氰酸酯基之預聚物(以下稱為末端NCO預聚物)，其末端NCO含量，由預聚物的保存安定性和硬化物的柔軟性為考量，以0.2~6.0重量%較佳，而以0.4~4.5重量%更佳。
再者，前述末端NCO預聚物的數量平均分子量，一般為500~30,000，若以聚胺基甲酸酯樹脂的加工性為考量，則以1,000~20,000較佳。
本發明之聚胺基甲酸酯樹脂，係可藉由使前述胺基甲酸酯預聚物(1)與下述(式1)所示化合物(2)反應而製得者。
(R1O)n-SiR3-n-R2-NH-R3-NH2 (式1)
(式中，R表示甲基或乙基，以甲基較佳；R1表示甲基或乙基，以甲基較佳；R2表示碳數2~10之烴基，以伸烷基較佳；R3表示碳數2~10之烴基，以伸烷基較佳)。
前述(式1)所示化合物，舉例而言，可為胺乙基胺丙基甲基二甲氧基矽烷、胺乙基胺丙基甲基三甲氧基矽烷、胺乙基胺丙基甲基二乙氧基矽烷、胺乙基胺丙基甲基三乙氧基矽烷等。其中，由物性觀點，以胺乙基胺丙基甲基二甲氧基矽烷、胺乙基胺丙基甲基三甲氧基矽烷較佳。
前述(式1)所示化合物的市售品實例，係例如信越化學公司製KBM-602、KBM-603等商品。
本發明的聚胺基甲酸酯樹脂，係將前述胺基甲酸酯預聚物(1)與前述(式1)所示化合物(2)，在其NCO/NH2當量比較佳為0.6~1.2、更佳為1.0~1.2之下反應而得。將前述胺基甲酸酯預聚物(1)與前述(式1)所示化合物於前述範圍內反應，以安定性之觀點係為有利的。
本發明的聚胺基甲酸酯樹脂，視其必要性，可混入一般性的添加成分，例如填料、塑化劑、黏著性賦予劑、搖變劑、老化防止劑、吸濕劑、防垂流劑、整平劑、紫外線吸收劑、抗氧化劑、賦黏劑及硬化觸媒等，而作為用於黏著劑、密封材、彈性體材料(胺基甲酸酯系塗膜防水材、胺基甲酸酯系外壁塗裝材、胺基甲酸酯系地板塗料、胺基甲酸酯系電線包覆材、胺基甲酸酯系彈性體成型材)等之硬化性組成物。
前述之填料，舉例而言，可為重質碳酸鈣、經脂肪酸處理碳酸鈣、碳酸鎂、矽藻土、燒結黏土、黏土等、或玻璃珠、矽微細中空球(Silas Baloon)、玻璃中空球、二氧化矽中空球、塑料中空球、含粉體之塑料中空球等的中空球類、滑石、氧化鈦、膨土、有機膨土、氧化鐵、氧化鋅、氫化蓖麻油、石棉、玻璃纖維等，其中以重質碳酸鈣較佳。本發明的聚胺基甲酸酯樹脂作為硬化性組成物時，以該硬化性組成物總重為基準，填料若適當地含有0~70重量%為宜。
前述之塑劑，舉例而言，可為酞酸二辛酯、酞酸二丁酯、酞酸丁基芐基酯等酞酸酯類；己二酸二辛酯、琥珀酸異癸酯、癸二酸二丁酯、油酸丁酯等脂肪族羧酸酯；季戊四醇酯等二醇酯類；磷酸二辛酯、磷酸三辛酯、磷酸三甲苯基酯等磷酸酯；環氧化大豆油、環氧硬脂酸芐酯等環氧系塑化劑；氯化石蠟等，其中以酞酸二壬酯較佳。本發明的聚胺基甲酸酯作為硬化性組成物時，以該硬化性組成物總量為基準，塑化劑若適當含有0~70重量%為宜。
前述黏著性賦予劑，舉例而言，可為N-(beta-胺乙基)-N'-(gamma-三甲氧基矽烷基丙基)-伸乙基二胺、N-(beta-胺乙基)-gamma-胺丙基三甲氧基矽烷等胺烷氧基矽烷；乙烯基三乙氧基矽烷、乙烯基三甲氧基矽烷、gamma-環氧丙氧基丙基三甲氧基矽烷、gamma-環氧丙氧基丙基三乙氧基矽烷、beta-(3,4-環氧環己基)乙基三甲氧基矽烷，其中以胺基矽烷化合物較佳。本發明的聚胺基甲酸酯樹脂作為硬化性組合物時，以該硬化性組成物之總重為基準，黏著性賦予劑若適當地含有0~10重量%為宜。
硬化觸媒，係為有機錫化合物，例如辛酸錫、環烷酸錫、硬脂酸錫、二辛酸二丁基錫、二月桂酸二丁基錫、二叔碳酸二辛基錫、雙三乙氧矽酸二丁基錫、二油烯基馬來酸二丁基錫、二醋酸二丁基錫、1,1,3,3,-四丁基-1,3-二月桂基氧羰基-二錫氧烷、雙乙氧基矽酸二丁基錫氧酯、氧化二丁基錫、氧化二丁基錫與酞酸酯的反應物、氧化二丁基錫與馬來酸二酯的反應物、二乙醯丙酮二丁基錫等。其他的有機金屬化合物，舉而言之，可為鉍、鋇、鈣、銦、鈦、鋯、鈣、鋅、鐵、鈷、鉛的羧酸(例如辛酸)鹽類等，例如辛酸鋇、辛酸鈣等。其等可單獨使用亦可2種以上併用。
含本發明聚胺基甲酸酯樹脂之硬化性組成物，係由前述各成分所構成，並可利用例如高速攪拌混合機或球磨機將該等成分混合後製得。
前述之硬化性物成物，可將聚胺基甲酸酯樹脂及前述調和成分全部混合為一液型，或是有含聚胺基甲酸酯樹脂之基劑及含硬化觸媒之硬化劑的二液型、抑或是將著色劑與塑化劑等組成的調色劑另作一成分而為三液型以使用之。
其次，前述之硬化性物成物，若為二液型時，可令前述基劑及前述硬化劑由以下範圍中選擇至少一個重量比作計量混合，於硬化後使用之：100:0.5~20較佳、100:1~15更佳，100:5~10最佳。
以下接著列舉實施例及比較列，對本發明作更具體的說明。惟，不得以該等說明對本發明作任何限制。
混合458克的數量平均分子量5,000之聚氧化伸丙基單醇(旭硝子公司製PML-S-1005)、462g的數量平均分子量13,000之聚氧化伸丙基二醇(旭硝子胺基甲酸酯公司製PML-4013)、以及53g的異佛酮二異氰酸酯。將該混合物於90℃反應24小時而得聚胺基甲酸酯預聚物。
在515克的該預聚物中，加入21克的胺乙基胺丙基甲基二甲氧基矽烷(信越化學公司製KBM-602)，在30℃下攪拌30分鐘。接著，在該預聚物中加入7.3克的胺丙基甲基二甲氧基矽烷(信越化學公司製KBM-902)及0.3克的甲醇，於30℃下攪拌30分鐘後，即得聚胺基甲酸酯樹脂。
混合458克的數量平均分子量5,000之聚氧化伸丙基單醇(旭硝子公司製PML-S-1005)、462g的數量平均分子量13,000之聚氧化伸丙基二醇(旭硝子胺基甲酸酯公司製PML-4013)、以及53g的異佛酮二異氰酸酯。將該混合物於90℃反應24小時而得聚胺基甲酸酯預聚物。
在515克的該預聚物中，加入21克的胺乙基胺丙基甲基三甲氧基矽烷(信越化學公司製KBM-603)，在30℃下攪拌30分鐘。接著，在該預聚物中加入7.3克的胺丙基甲基二甲氧基矽烷(信越化學公司製KBM-902)及0.3克的甲醇，於30℃下攪拌30分鐘後，即得聚胺基甲酸酯樹脂。
將500克的數量平均分子量10,000之聚氧化伸丙基二醇(旭硝子公司製PML-4011)與異佛酮二異氰酸酯(住化拜耳胺基甲酸酯製Desmodur I)以NCO/OH當量比2.0於90℃反應42小時，即得聚胺基甲酸酯預聚物。
在444克的該預聚物中，加入51.3克的胺乙基胺丙基甲基二甲氧基矽烷(信越化學公司製KBM-602)。以91.5克的丙烯酸-2-乙基己酯於50℃下攪拌10日後，即得聚胺基甲酸酯樹脂。
將210克的數量平均分子量10,000之聚氧化伸丙基二醇(旭硝子公司製PML-4011)與異佛酮二異氰酸酯(住化拜耳胺基甲酸酯製Desmodur I)以NCO/OH當量比2.0於90℃反應42小時，即得在20℃下黏度20,000mPa*s的聚胺基甲酸酯預聚物。
在104克的該預聚物中，加入8克的胺乙基胺丙基甲基二甲氧基矽烷(信越化學公司製KBM-602)。於30℃下攪拌30分鐘後，得到具有高黏度而無法攪拌的聚胺基甲酸酯樹脂。
將第1表所示重量的調配原料加熱並送入附有減壓裝置的混合攪拌機中，攪拌30分鐘。接著在60℃下混合攪拌30分鐘，再於真空減壓下攪拌混合20分鐘後即得基劑。
將第1表所示重量的硬化觸媒及碳酸鈣在室溫下混合，即得硬化劑
將依上述調製而成的基劑與硬化劑以100:10(重量比)混合，即得硬化性組成物。
單位：克
(註1) 松本油脂公司製，平均粒徑60μm，Tg 140℃
(註2) 重質碳酸鈣，白石鈣公司製「WHITON SB」，平均粒徑3.7μm
(註3) 丸尾鈣公司製「CalFine 500」、一次粒子系0.05μm，BET比表面積17m2/g
(註4) DINP、新日本理化公司製「DINP」
(註5) 受阻胺系光安定劑(HALS)、施巴公司製「tinuvin123」
(註6) 旭電化(ADEKA)公司製「AO-60P」
(註7) 城北化學工業公司製「JF79」
(註8) 2價錫系觸媒，日東化成公司製「U-28」
(註9) 4價錫系觸媒，日東化成公司製「C-501」
(註10) 胺系觸媒，日油公司製「Amino BB」
對於如前述調製之各聚胺基甲酸酯樹脂及硬化性組成物，進行以下的性能試驗。其結果示於第2表及第3表。
依前述調製的聚胺基甲酸酯樹脂，使用旋轉式黏度計(brookfiled公司製數位黏度計)於20℃下測試。
於35℃ x90%RH的恆溫恆濕槽中，對依前述調製之聚胺基甲酸酯樹脂，觀察其保存安定性24小時。
在JIS H 4000規定之A5052鋁板(50x50x5mm)上塗佈底漆(商品名：Primer-US03：三司達技研公司製)，並施置依前述調製而成的2成分型硬化性組成物。固化(條件：20℃ x7日+50℃ x7日)後，依循JIS A 1439 5.20「拉伸黏著性試驗」(2004)，測定初期固化後(20℃ x7日+50℃ x7日)50%拉伸應力[N/mm2]、最大拉伸應力[N/mm2]以及最大荷重時的伸長率[%]。
在以上的結果中，於實施例1及2所製造之本發明之聚胺基甲酸酯樹脂，其黏度為50,000~70,000mPa‧s，與此相對，比較例1及2所製造之非本發明之聚胺基甲酸酯樹脂，其黏度在200,000以上。由此可知，本發明之聚胺基甲酸酯樹脂具有優良的加工性。其次，可知於實施例1及2所製造之本發明之聚胺基甲酸酯樹脂保存安定性良好，而與此相對，於比較例2所製造之聚胺基甲酸酯樹脂之保存安定性不足。再者，使用實施例3及4中本發明之聚胺基甲酸酯樹脂所製造的硬化性組成物，其50%拉伸應力係0.14 N/mm2以下且最大拉伸應力係0.51 N/mm2以下，與此相對，比較例3中使用非本發明之聚胺基甲酸酯樹脂所製造的硬化性組成物，其50%拉伸應力係0.30 N/mm2且最大拉伸應力係0.75 N/mm2以下。由此可知，藉由使用本發明之聚胺基甲酸酯樹脂，可製得較低模數之彈性體。
Claims (5)
- 一種聚胺基甲酸酯樹脂，其係藉由使(1)胺基甲酸酯預聚物及(2)以下述(式1)表示之化合物反應而得者：(1)胺基甲酸酯預聚物，其係使(a)平均末端羥基數為1.3~2.1的單元醇與多元醇之混合物，與(b)聚異氰酸酯反應而得；(2)以下述(式1)表示之在分子內具有交聯性矽烷基與亞胺基及胺基之化合物：(R1O)n-SiR3-n-R2-NH-R3-NH2 (式1)(式中，R表示甲基或乙基，R1表示甲基或乙基，R2表示碳數2~10之烴基，R3表示碳數2~10之烴基，n為1、2或3)；前述單元醇與多元醇之混合物(a)及聚異氰酸酯(b)之反應係於NCO/OH之當量比為1.6~2.5的範圍內進行，且，以該混合物(a)的總重為基準，該單元醇與多元醇之混合物(a)係使20重量%~80重量%之單元醇與20重量%~80重量%之多元醇混合而得。
- 如申請專利範圍第1項之聚胺基甲酸酯樹脂，其中多元醇的數量平均分子量(Mn)為500~30,000。
- 如申請專利範圍第1或2項之聚胺基甲酸酯樹脂，其中多元醇係聚氧伸丙基二醇。
- 如申請專利範圍第1項之聚胺基甲酸酯樹脂，其中與該預聚物與(式1)所示化合物之反應係於NCO/NH2之當量比為0.6~1.2的範圍內進行。
- 一種聚胺基甲酸酯樹脂之製造方法，其特徵為藉由使(1)胺基甲酸酯預聚物及(2)以下述(式1)表示之化合物反應：(1)胺基甲酸酯預聚物，其係由使(a)平均末端羥基數為1.3~2.1的的單元醇與多元醇之混合物，與(b)聚異氰酸酯反應而得；(2)以下述(式1)表示之在分子內具有交聯性矽烷基與亞胺基及胺基之化合物：(R1O)n-SiR3-n-R2-NH-R3-NH2 (式1)(式中，R表示甲基或乙基，R1表示甲基或乙基，R2表示碳數2~10之烴基，R3表示碳數2~10之烴基，n為1、2或3)；前述單元醇與多元醇之混合物(a)及聚異氰酸酯(b)之反應係於NCO/OH之當量比為1.6~2.5的範圍內進行，且，以該混合物(a)的總重為基準，該單元醇與多元醇之混合物(a)係使20重量%~80重量%之單元醇與20重量%~80重量%之多元醇混合而得。
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| CN103421160A (zh) * | 2012-05-25 | 2013-12-04 | 亨茨曼国际有限公司 | 聚氨酯灌浆组合物 |
| CN116836543A (zh) * | 2023-07-09 | 2023-10-03 | 东莞市进升五金制品有限公司 | 一种手表五金按键的制备方法 |
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| JPS6329954A (ja) | 1986-07-23 | 1988-02-08 | Toshiba Corp | 半導体装置の製造方法 |
| DE3629237A1 (de) | 1986-08-28 | 1988-03-03 | Henkel Kgaa | Alkoxysilanterminierte, feuchtigkeitshaertende polyurethane sowie ihre verwendung fuer klebe- und dichtungsmassen |
| US5068304A (en) | 1988-12-09 | 1991-11-26 | Asahi Glass Company, Ltd. | Moisture-curable resin composition |
| JP3042692B2 (ja) | 1988-12-09 | 2000-05-15 | 旭硝子株式会社 | 湿気硬化性樹脂組成物 |
| JP2906497B2 (ja) | 1988-12-09 | 1999-06-21 | 旭硝子株式会社 | 湿気硬化性樹脂組成物 |
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| DE59911016D1 (de) | 1998-07-10 | 2004-12-09 | Sanyo Chemical Ind Ltd | Neue polyoxyalkylenpolyole und verfahren zur herstellung eines polymers mit ringöffnung |
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| US7115696B2 (en) * | 2002-05-31 | 2006-10-03 | Bayer Materialscience Llc | Moisture-curable, polyether urethanes with reactive silane groups and their use as sealants, adhesives and coatings |
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| US7365145B2 (en) * | 2005-09-14 | 2008-04-29 | Momentive Performance Materials Inc. | Moisture curable silylated polymer containing free polyols for coating, adhesive and sealant application |
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| JP4937595B2 (ja) * | 2006-02-07 | 2012-05-23 | オート化学工業株式会社 | 一液型湿気硬化性組成物、シーリング材組成物及び接着剤組成物 |
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| JP5769929B2 (ja) | 2015-08-26 |
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