US20010003763A1 - Curable polymer composition - Google Patents
Curable polymer composition Download PDFInfo
- Publication number
- US20010003763A1 US20010003763A1 US09/011,449 US1144998A US2001003763A1 US 20010003763 A1 US20010003763 A1 US 20010003763A1 US 1144998 A US1144998 A US 1144998A US 2001003763 A1 US2001003763 A1 US 2001003763A1
- Authority
- US
- United States
- Prior art keywords
- group
- silicon
- polymer composition
- curable polymer
- groups
- 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.)
- Granted
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 67
- 239000000203 mixture Substances 0.000 title claims abstract description 53
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 52
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 50
- 239000010703 silicon Substances 0.000 claims abstract description 43
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 39
- 125000005702 oxyalkylene group Chemical group 0.000 claims abstract description 34
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 28
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000006482 condensation reaction Methods 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 14
- 229920001296 polysiloxane Polymers 0.000 claims description 9
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 150000003377 silicon compounds Chemical class 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 239000000463 material Substances 0.000 abstract description 19
- -1 polyoxypropylene Polymers 0.000 description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- 238000000034 method Methods 0.000 description 10
- 239000004014 plasticizer Substances 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 8
- 238000009833 condensation Methods 0.000 description 8
- 230000005494 condensation Effects 0.000 description 8
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 6
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 6
- 0 *[SiH](C)O[Si](*)(C)C Chemical compound *[SiH](C)O[Si](*)(C)C 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- BKUSIKGSPSFQAC-RRKCRQDMSA-N 2'-deoxyinosine-5'-diphosphate Chemical compound O1[C@H](CO[P@@](O)(=O)OP(O)(O)=O)[C@@H](O)C[C@@H]1N1C(NC=NC2=O)=C2N=C1 BKUSIKGSPSFQAC-RRKCRQDMSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- 239000002210 silicon-based material Substances 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- SEEOMASXHIJCDV-UHFFFAOYSA-N 3-methyloctane Chemical compound CCCCCC(C)CC SEEOMASXHIJCDV-UHFFFAOYSA-N 0.000 description 3
- ZVFDTKUVRCTHQE-UHFFFAOYSA-N Diisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C ZVFDTKUVRCTHQE-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- PLZDDPSCZHRBOY-UHFFFAOYSA-N inaktives 3-Methyl-nonan Natural products CCCCCCC(C)CC PLZDDPSCZHRBOY-UHFFFAOYSA-N 0.000 description 3
- 229940094933 n-dodecane Drugs 0.000 description 3
- 239000012188 paraffin wax Substances 0.000 description 3
- 239000003348 petrochemical agent Substances 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 3
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- SGVYKUFIHHTIFL-UHFFFAOYSA-N 2-methylnonane Chemical compound CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 description 2
- LAIUFBWHERIJIH-UHFFFAOYSA-N 3-Methylheptane Chemical compound CCCCC(C)CC LAIUFBWHERIJIH-UHFFFAOYSA-N 0.000 description 2
- SOMJQWRITYTQJL-UHFFFAOYSA-N 6-methyltridecane Chemical compound CCCCCCCC(C)CCCCC SOMJQWRITYTQJL-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 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
- IGHXQNDUQCTKSH-UHFFFAOYSA-N CCC(C)(C)C(=O)OC Chemical compound CCC(C)(C)C(=O)OC IGHXQNDUQCTKSH-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003302 alkenyloxy group Chemical group 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 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
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- ZUBZATZOEPUUQF-UHFFFAOYSA-N isononane Chemical compound CCCCCCC(C)C ZUBZATZOEPUUQF-UHFFFAOYSA-N 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000005498 phthalate group Chemical class 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229920005573 silicon-containing polymer Polymers 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 125000002889 tridecyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])[H] 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- YOBOXHGSEJBUPB-MTOQALJVSA-N (z)-4-hydroxypent-3-en-2-one;zirconium Chemical compound [Zr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O YOBOXHGSEJBUPB-MTOQALJVSA-N 0.000 description 1
- TYKCBTYOMAUNLH-MTOQALJVSA-J (z)-4-oxopent-2-en-2-olate;titanium(4+) Chemical compound [Ti+4].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O TYKCBTYOMAUNLH-MTOQALJVSA-J 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
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 1
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-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
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 1
- QHVBLSNVXDSMEB-UHFFFAOYSA-N 2-(diethylamino)ethyl prop-2-enoate Chemical compound CCN(CC)CCOC(=O)C=C QHVBLSNVXDSMEB-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-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
- CEYHHQSTMVVZQP-UHFFFAOYSA-N 2-ethenoxyethanamine Chemical compound NCCOC=C CEYHHQSTMVVZQP-UHFFFAOYSA-N 0.000 description 1
- NLHRRMKILFRDGV-UHFFFAOYSA-N 3-methyltridecane Chemical compound CCCCCCCCCCC(C)CC NLHRRMKILFRDGV-UHFFFAOYSA-N 0.000 description 1
- QGEPIAWTQXRCGQ-UHFFFAOYSA-N 4,5-dipropyloctane Chemical compound CCCC(CCC)C(CCC)CCC QGEPIAWTQXRCGQ-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 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
- 239000005995 Aluminium silicate Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- 229920000742 Cotton Polymers 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
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 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
- 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
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001253 acrylic acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- IKHOZNOYZQPPCK-UHFFFAOYSA-K aluminum;4,4-diethyl-3-oxohexanoate Chemical compound [Al+3].CCC(CC)(CC)C(=O)CC([O-])=O.CCC(CC)(CC)C(=O)CC([O-])=O.CCC(CC)(CC)C(=O)CC([O-])=O IKHOZNOYZQPPCK-UHFFFAOYSA-K 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([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])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])[H] 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- NUMHJBONQMZPBW-UHFFFAOYSA-K bis(2-ethylhexanoyloxy)bismuthanyl 2-ethylhexanoate Chemical compound [Bi+3].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O NUMHJBONQMZPBW-UHFFFAOYSA-K 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
- 150000001621 bismuth Chemical class 0.000 description 1
- NSPSPMKCKIPQBH-UHFFFAOYSA-K bismuth;7,7-dimethyloctanoate Chemical compound [Bi+3].CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O NSPSPMKCKIPQBH-UHFFFAOYSA-K 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([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])[H] 0.000 description 1
- 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 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- SRXOCFMDUSFFAK-UHFFFAOYSA-N dimethyl peroxide Chemical compound COOC SRXOCFMDUSFFAK-UHFFFAOYSA-N 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
- 239000013013 elastic material Substances 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000962 organic 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
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
- CZMAXQOXGAWNDO-UHFFFAOYSA-N propane-1,1,2-triol Chemical compound CC(O)C(O)O CZMAXQOXGAWNDO-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 150000003682 vanadium compounds Chemical class 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
Definitions
- Polymers having a silicon-containing group which has a hydroxyl or hydrolyzable group bonded to the silicon atom and can be crosslinked through a silanol condensation reaction (hereinafter referred to as “reactive silicon-containing group”), are crosslinked and cured in the presence of moisture.
- Curable compositions comprising polymers having backbones of oxyalkylene polymers such as polyoxypropylene and the reactive silicon-containing group among the above polymers are widely used, for example, as sealants for construction, since they are in the liquid state at room temperature, and are cured to provide rubbery elastic materials.
- tack stickinginess
- dirts or dusts adhere to the surfaces, which deteriorate the appearance of the cured materials.
- the present invention provides a curable polymer composition
- a curable polymer composition comprising
- the particularly preferable reactive silicon-containing group is —Si(CH 3 )—(OCH 3 ) 2 .
- the amount of the paraffinic hydrocarbon (b) is preferably between 0.1 and 150 wt. parts, more preferably between 1 and 60 wt. parts per 100 wt. parts of the oxyalkylene polymer (a).
- the amount of the paraffinic hydrocarbon is less than 0.1 wt. parts, the effects of the addition of the paraffinic hydrocarbon are not sufficiently achieved.
- the amount of the paraffinic hydrdocarbon exceeds 150 wt. parts, the mechanical strength of the cured material deteriorate.
- the amount of the silanol condensation catalyst is too small in relation to the oxyalkylene polymer, the curing rate becomes too low so that the curing reaction may not proceed sufficiently.
- the amount of the silanol condensation catalyst is too large in relation to the oxyalkylene polymer, the composition is partly heated or foamed during curing and thus good cured materials may not be obtained.
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
- The present invention relates to a curable polymer composition which is curable in the presence of moisture and has improved surface tack (stickiness).
- Polymers having a silicon-containing group, which has a hydroxyl or hydrolyzable group bonded to the silicon atom and can be crosslinked through a silanol condensation reaction (hereinafter referred to as “reactive silicon-containing group”), are crosslinked and cured in the presence of moisture. Curable compositions comprising polymers having backbones of oxyalkylene polymers such as polyoxypropylene and the reactive silicon-containing group among the above polymers are widely used, for example, as sealants for construction, since they are in the liquid state at room temperature, and are cured to provide rubbery elastic materials. However, tack (stickiness) remains on the surfaces of the cured materials of such compositions according to the compositions of the curable compositions or curing conditions, and dirts or dusts adhere to the surfaces, which deteriorate the appearance of the cured materials.
- To overcome such defects, for example, JP-A-55-21453 discloses the addition of organic silicone polymers to the polymers having the reactive silicon-containing group. The addition of the organic silicone polymer deteriorate mechanical properties such as modulus, strength at break, elongation, and the like, although the tack is improved.
- JP-A-55-36241 discloses the addition of photocurable materials, JP-A-1-149851 discloses the addition of liquid diene polymers, and JP-A-1-188557 discloses the addition of silicone compounds having long chain hydrocarbon groups, to the polymers having the reactive silicon-containing group. However, the addition of such materials increases the cost of the curable compositions, and also has drawbacks that the tack is insufficient in a relatively early stage of curing, and satisfactory effects are not obtained with some compositions or under some curing conditions.
- One object of the present invention is to provide a curable composition comprising a polymer having a reactive silicon-containing group, which is less expansive and can decrease the tack of a cured product without deteriorating modulus and elongation at break of the cured material.
- Accordingly, the present invention provides a curable polymer composition comprising
- (a) an oxyalkylene polymer having a silicon-containing group which has a hydroxyl or hydrolyzable group bonded to the silicon atom and can be crosslinked through a silanol condensation reaction, and
- (b) a paraffinic hydrocarbon.
- The curable polymer composition of the present invention may additionally contain (c) a silicone compound having a long chain hydrocarbon group, which is preferably a silicone compound having a C8-20 alkyl group.
- The backbone of the oxyalkylene polymer having the reactive silicon-containing group (a) which is contained in the composition of the present invention comprises a repeating unit of the formula (1):
- —R1—O— (1)
- wherein R1 is a divalent organic group, preferably a straight or branched alkylene group having 1 to 1 4 carbon atoms.
- Examples of the repeating unit of the formula (1) are —CH2O—, —CH2CH2O—, —CH2CH(CH3)O—, —CH2CH(C2H5)O—, —CH2C(CH3)2O—, —CH2CH2CH2CH2O—, and the like.
- The backbone of the oxyalkylene polymer may consist of the single kind of the repeating unit, while it may comprise two or more kinds of repeating units in which the R1 groups are different. In particular, polymers comprising propylene oxide, particularly polyoxypropylene are preferable, when the compositions are used as sealants, and the like.
-
- wherein R2 and R3 are the same or different and represent a C1-20 alkyl group, a C6-20 aryl group, a C7-20 aralkyl group or a triorganosiloxy group of the formula: (R4)3SiO— in which three R4 groups are the same or different and represent a C1-20 alkyl group, provide that when two or more R2 or R3 groups are present, they may be the same or different; the X groups are the same or different and represent a hydroxyl group or a hydrolyzable group; a is 0, 1 or 2;
-
- may be the same or different.
- The hydrolyzable group X in the formula (2) may not be limited, and may be any conventional hydrolyzable group. Examples of such a group are a hydrogen atom, a halogen atom, an alkoxy group, an acyloxy group, a ketoxymate group, an amino group, an amido group, an acid amide group, an aminoxy group, a mercapto group, an alkenyloxy group, and the like. Among them, a hydrogen atom, alkoxy, acyloxy, ketoximate, amino, amido, aminoxy, mercapto and alkenyloxy groups are preferable. In particular, the alkoxy group is preferable in view of its mild hydrolyzability and easy handling.
- One, two or three hydrolyzable groups and/or hydroxyl groups can be attached to one silicon atom, and the total number of the hydrolyzable groups and/or hydroxyl groups, that is, (na+b) is preferably between, 1 and 5. When two or more hydrolyzable or hydroxyl groups are present in the reactive silicon-containing group, they may be the same or different.
- The reactive silicon-containing group contains at least one silicon atom. When the silicon atoms are bonded through siloxane bonds or the like, the number of silicon atoms is preferably about 20.
-
- wherein R3, X and b are the same as defined above, because of easy availability.
- Specific examples of the R2 and R3 groups are alkyl groups (e.g. a methyl group, an ethyl group, etc.), cycloalkyl groups (e.g. a cyclohexyl group, etc.), aryl groups (e.g. a phenyl group, etc.), aralkyl groups (e.g. a benzyl group, etc.), triorganosiloxy groups of the formula (R4)3SiO— in which R4 is a methyl group or a phenyl group. In particular, a methyl group is preferable as the R2 and R3 groups.
- The particularly preferable reactive silicon-containing group is —Si(CH3)—(OCH3)2.
- The reactive silicon-containing group may be introduced in the polymers by any known methods. The following methods are exemplified:
- (i) An oxyalkylene polymer having a functional group such as a hydroxyl group in a molecule is reacted with an organic compound having an unsaturated group and an active group which is reactive with the functional group in the oxyalkylene polymer, to obtain the oxyalkylene polymer having unsaturated groups. Alternatively, an epoxy compound having an unsaturated group and an alkylene oxide are copolymerized to obtain an oxyalkylene polymer having an unsaturated groups. Then, the reaction product is reacted with a hydrosilane having a reactive silicon-containing group for the hydrosilylation of the reaction product.
- (ii) The oxyalkylene polymer having the unsaturated groups, which has been obtained in the same manner as in the method (i), is reacted with a compound having a mercapto group and a reactive silicon-containing group.
- (iii) An oxyalkylene polymer having a functional group such as a hydroxyl group, an epoxy group, an isocyanate group, etc. is reacted with a compound having a reactive silicon-containing group and a functional group reactive with the above functional group.
- Among these methods, the method (i) and the method (iii) in which a polymer having a hydroxyl group at a chain end and a compound having an isocyanate group and a reactive silicon-containing group are reacted, are preferable.
- The oxyalkylene polymer as the component (a) used according to the present invention may be a linear or branched one, and its molecular weight is preferably between about 500 and about 50,000, preferably between 1000 and 20,000.
- The number of the reactive silicon-containing groups contained in the oxyalkylene polymer is at least one, preferably between 1.1 and 5, on the average, per one molecule of the polymer. When the number of the reactive silicon-containing groups in the molecule is less than one, the polymer has insufficient curing properties. When the number is too large, the network becomes overly dense, and thus the cured material does not have good mechanical properties.
- Specific examples of the oxyalkylene polymers as the component (a) according to the present invention are those disclosed in JP-B-45-36319, JP-B-46-12154, JP-A-50-156599, JP-A-54-6096, JP-A-55-13767, JP-A-55-13768, JP-A-57-164123, JP-B-3-2450, U.S. Pat. No. 3,632,557, U.S. Pat. No. 4,345,053, U.S. Pat. No. 4,366,307 and U.S. Pat. No. 4,960,844, and oxyalkylene polymers having a large number average molecular weight of at least 6000 and a narrow molecular weight distribution Mw/Mn of 1.6 or less which are disclosed in JP-A-61-197631, JP-A-61-215622, JP-A-61-215623 and JP-A-61-218632. The disclosures of the above US patents are hereby incorporated by reference.
- The oxyalkylene polymers having the reactive silicon-containing group may be used independently, or as a mixture of two or more of them. Blends of the oxyalkylene polymers with vinyl polymers having a reactive silicon-containing group may be used.
- Methods for the production of the blends of the oxyalkylene polymers and vinyl polymers having the reactive silicon-containing group are disclosed in JP-A-59-122541, JP-A-63-112642, JP-A-6-172631, and the like.
- Preferable examples of the vinyl polymer having the reactive silicon-containing group are copolymers of acrylate and/or methacrylate ester monomeric units molecular chain of which is represented by the following formula (5) and which has a reactive silicon-containing group and an alkyl group having 1 to 8 carbon atoms, and acrylate and/or methacrylate ester monomeric units molecular chain of which is represented by the following formula (6) and which has an alkyl group having at least 10 carbon atoms:
-
- wherein R6 is the same as defined above, and R7 is an alkyl group having at least 10 carbon atoms.
- Examples of R5 in the formula (5) are alkyl groups having 1 to 8 carbon atoms, preferably 1 to 4 carbon atoms, more preferably 1 or 2 carbon atoms, such as a methyl group, an ethyl group, a propyl group, a n-butyl group, a tert.-butyl group, 2-ethylhexyl group, etc. The kind of the alkyl group R5 may be a single kind alkyl group, or a combination of two or more alkyl groups.
- Examples of R7 in the formula (6) are long chain alkyl groups having at least 10 carbon atoms, usually 10 to 30 carbon atoms, preferably 10 to 20 carbon atoms, such as a lauryl group, a tridecyl group, a cetyl group, a stearyl group, etc. The kind of the alkyl group R7 may be a single kind alkyl group, or a combination of two or more alkyl groups.
- The backbone of the above vinyl copolymer comprises substantially the repeating units of the formulas (5) and (6). Herein, the term “substantially” means that the total weight of the repeating units of the formulas (5) and (6) exceeds 50 wt. %. Preferably, the total weight of the repeating units of the formulas (5) and (6) is at least 70 wt. %.
- A weight ratio of the repeating units of the formula (5) to those of the formula (6) is preferably between 95:5 and 40:60, more preferably between 90:10 and 60:40.
- The copolymer may comprise other repeating units in addition to the repeating units of the formulas (5) and (6). Examples of monomers which provide the other repeating units are acrylic acids (e.g. acrylic acid, methacrylic acid, etc.), monomers having an amide group (e.g. acrylamide, methacrylamide, N-methylolacrylamide, N-methylolmethacrylamide, etc.), monomers having an epoxy group (e.g. glycidyl acrylate, glycidyl methacrylate, etc.), monomers having an amino group (e.g. diethylaminoethyl acrylate, diethylaminoethyl methacrylate, aminoethyl vinyl ether, etc.), acrylonitrile, styrene, α-methylstyrene, alkyl vinyl ethers, vinyl chloride, vinyl acetate, vinyl propionate, ethylene, and the like.
- The number average molecular weight of the copolymer is preferably between 500 and 100,000 in view of the easy handing.
- The reactive silicon-containing group contained in the copolymer may be the same as that contained in the oxyalkylene polymer.
- For the preparation of the blend of the oxyalkylene polymer and the vinyl polymer having the reactive silicon-containing group, the (meth)acrylate ester monomers may be polymerized in the presence of the oxyalkylene polymer having the reactive silicon-containing group. This method is disclosed in JP-A-59-78223, JP-A-59-168014, JP-A-60-228516, JP-A-60-228517, and the like. The preparation method is not limited to the above method.
- The curable composition of the present invention may contain other polymers having a reactive silicon-containing group, for example, polydimethylsiloxane and the like, in addition to the oxyalkylene polymer (a) having at least one reactive silicon-containing group in a molecule.
- The paraffinic hydrocarbon (b) may be any known paraffinic hydrocarbon. The paraffinic hydrocarbon may be a straight or branched one. The significant effects can be achieved, when the paraffinic hydrocarbon having at least 6 carbon atoms, preferably 8 to 18 carbon atoms is used. Hydrocarbons having too small or too large number of carbon atoms may not achieve the effects of the present invention sufficiently under the employed temperature conditions, since those having too small number of carbon atoms evaporate at high temperature, while those having too large number of carbon atoms solidify at low temperature.
- The specific gravity of the paraffinic hydrocarbon used according to the present invention is 0.85 or less, preferably 0.83 or less, in particular 0.80 or less.
- The paraffinic hydrocarbon used according to the present invention does not include one having a hetero atom such as chlorinated paraffin.
- Specific examples of the paraffinic hydrocarbon are n-octane, 2-ethylheptane, 3-methylheptane, n-nonane, 2-methyloctane, 3-methyloctane, n-decane, 2-methylnonane, 3-methylnonane, n-undecane, n-dodecane, n-tridecane, n-tetradecane, 4,5-dipropyloctane, 3-methyltridecane, 6-methyltridecane, n-hexadecane, n-heptadecane, n-octadecane, and the like. They may be used independently or as a mixture of two or more of them.
- The amount of the paraffinic hydrocarbon (b) is preferably between 0.1 and 150 wt. parts, more preferably between 1 and 60 wt. parts per 100 wt. parts of the oxyalkylene polymer (a). When the amount of the paraffinic hydrocarbon is less than 0.1 wt. parts, the effects of the addition of the paraffinic hydrocarbon are not sufficiently achieved. When the amount of the paraffinic hydrdocarbon exceeds 150 wt. parts, the mechanical strength of the cured material deteriorate.
- The composition of the present invention may contain hydrocarbons other than the paraffinic hydrocarbons. Examples of such hydrocarbons are olefinic, diolefinic, polyolefinic and acetylenic hydrocarbons. Furthermore, reaction products obtained by hydrogenating polymers of unsaturated hydrocarbons may be used.
- The composition of the present invention may optionally contain (c) a silicone compound having a long chain hydrocarbon group. The addition of the silicone compound having the long chain hydrocarbon group can further improve the tack on the surface of the cured material.
- The long chain hydrocarbon group in the silicon compound (c) includes long chain alkyl groups, long chain alkenyl groups, cycloalkyl groups having a long chain alkyl or alkenyl group, which have a silicon-containing group bonded to one chain end, and long chain alkylene groups having silicon-containing groups bonded to both chain ends. The hydrocarbon group contains at least 8 carbon atoms, preferably 8 to 20 carbon atoms in the hydrocarbon part contained in the straight chain (excluding a cyclic hydrocarbon group).
- Specific examples of the long chain alkyl group are a n-octyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a cetyl group, a stearyl group, an eicosyl group, and the like. Specific examples of the long chain alkenyl group are an octenyl group, a nonenyl group, a decenyl group, a dodecenyl group, a tetradecenyl group, a hexadecenyl group, an octadecenyl group, an eicosenyl group, an octadecadienyl group, a 9,12,15-octadecatrienyl group, a 9,11,13-octadecatrienyl group, and the like. Specific examples of the long chain alkylene group are —(CH2)11—, —(CH2)13—, —(CH2)15—, —(CH2)19—, —(CH2)20—, and the like.
- The silicon-containing compound having the long chain hydrocarbon group has also a reactive silicon-containing group. This reactive silicon-containing group may be the same as that contained in the oxyalkylene polymer. A reactive silicon-containing group having one silicon atom is preferable in view of the cost.
- Specific examples of the silicon-containing compound having the long chain hydrocarbon group are CH3(CH2)9Si(OCH3)3, CH3(CH2)17Si(OCH3)3, CH3(CH2)11Si(OC2H5)3, CH3(CH2)17Si(OC2H5)3, CH3(CH2)9Si(CH3)(OCH3)2, CH3(CH2)17Si(CH3)(OCH3)2, (CH3O)3Si(CH2)10 Si(OCH3)3, (CH3O)2(CH3)Si(CH2)10Si(CH3)(OCH3)2, and the like.
- The amount of the silicon-containing compound having the long chain hydrocarbon group is preferably between 0.1 and 30 wt. parts, more preferably between 0.5 and 20 wt. parts per 100 wt. parts of the oxyalkylene polymer. When the amount of this silicon-containing compound is less than 0.1 wt. parts, the effects of the addition of this compound may not be achieved. When this amount exceeds 30 wt. parts, the cost increases, and the tensile properties of the cured material may deteriorate.
- The composition of the present invention may optionally contain a plasticizer. In such a case, the amount of the plasticizer should be adjusted in accordance with the amount of the paraffinic hydrocarbon (b) contained in the composition. The amount of the plasticizer is selected so that the total amount of the paraffinic hydrocarbon and plasticizer is in the range between 0.1 and 150 wt. parts, preferably around 100 wt. parts, per 100 wt. parts of the oxyalkylene polymer, in which range the preferable effects are achieved. When the amount of the plasticizer exceeds 150 wt. parts, the mechanical strength of the cured material decreases, and the effect for improving the tack is not achieved.
- Specific examples of the plasticizer are phthalates (e.g. dioctyl phthalate, diisodecyl phthalate, dibutyl phthalate, butylbenzyl phthalate, etc.), epoxy plasticizers (e.g. epoxidized soybean oil, epoxidized linseed oil, benzyl epoxystearate, etc.), polyester plasticizers (e.g. polyesters of dibasic acids and dihydric alcohols, etc.), polyethers (e.g. polypropylene glycol and its derivatives, etc.), styrenic polymers (e.g. poly-α-methylstyrene, polystyrene, etc.), polybutadiene, butadiene-acrylonitrile copolymers, polychloroprene, polyisobutylene, polybutene, chlorinated paraffins, and the like. They may be used independently or as a mixture of two or more of them.
- The curable composition of the present invention may contain a silanol condensation catalyst for accelerating the reaction of the reactive silicon-containing group. Preferable examples of the silanol condensation catalyst are titanates (e.g. tetrabutyl titanate, tetrapropyl titanate, etc.); organic tin compounds (e.g. dibutyltin dilaurate, dibutyltin maleate, dibutyltin diacetate, tin octylate, tin naphthenate, reaction products of dibutyltin oxide and phthalates, dibutyltin diacetylacetonate, etc.); organic aluminum compounds (e.g. aluminum trisacetylacetonate, aluminum trisethylacetoacetate, diisopropoxyaluminum ethylacetoacetate, etc.); reaction products of bismuth salts and carboxylic acids (e.g. bismuth-tris(2-ethyl-hexanoate), bismuth-tris(neodecanoate), etc.); chelating agents (e.g. zirconium tetraacetylacetonate, titanium tetraacetylacetonate, etc.), organic lead compounds (e.g. lead octylate, etc.); organic vanadium compounds; amine compounds (e.g. butylamine, octylamine, dibutylamine, monoethanolamine, diethanolamine, triethanolamine, diethylenetriamine, triethylenetetramine, oleylamine, cyclohexyl-amine, benzylamine, diethylaminopropylamine, xylylenediamine, triethylenediamine, guanidine, diphenylguanidine, 2,4,6-tris(dimethylaminomethyl)phenol, morpholine, N-methylmorpholine, 2-ethyl-4-methylimidazole, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), etc.) and salts of these amine compounds with carboxylic acid and the like; low molecular weight polyamide resins obtained from excessive polyamines and polybasic acids; reaction products of excessive polyamines and epoxy compounds; and the like. Furthermore, conventionally used other condensation catalysts may be used.
- The silanol condensation catalysts may be used independently or as a mixture of two or more of them.
- Among the above silanol condensation catalysts, organic metal compounds, or combinations of organic metal compounds and amine compounds are preferable in view of the curing properties.
- The amount of the silanol condensation catalyst is preferably between 0.01 and 20 wt. parts, more preferably between 0.1 and 10 wt. parts per 100 wt. parts of the oxyalkylene polymer having the reaction silicon-containing group.
- When the amount of the silanol condensation catalyst is too small in relation to the oxyalkylene polymer, the curing rate becomes too low so that the curing reaction may not proceed sufficiently. When the amount of the silanol condensation catalyst is too large in relation to the oxyalkylene polymer, the composition is partly heated or foamed during curing and thus good cured materials may not be obtained.
- If desired, the curable composition of the present invention may contain various additives such as dehydrating agents, compatibilizers, adhesion-improvers, physical property-modifiers, storage stability improvers, fillers, anti-aging agents, UV ray absorbers, metal-deactivating agents, antiozonants, light-stabilizers, amine base radical chain transfer inhibitors, phosphorus base peroxide-decomposers, lubricants, pigments, foaming agents, flame retardants, anti-static agents, and the like.
- When the fillers are used as the additives, the following fillers can be used:
- wood meal, walnut shell flour, rice hull powder, pulp, cotton chips, mica, graphite, diatomaceous earth, china clay, kaolin, clay, talk, fumed silica, precipitated silica, silica, quartz, glass beads, calcium carbonate, magnesium carbonate, titanium oxide, aluminum powder, zinc powder, asbestos, glass fiber, carbon fiber, and the like. These fillers may be used independently or as a mixture of two or more of them.
- The method for the preparation of the curable polymer composition of the present invention is not limited, and any conventional method may be used. For example, the components (a) and (b) and optional components are compounded, and dissolved and mixed with a mixer, rolls or a kneader.
- The curable polymer composition of the present invention may be prepared in the form of a two pack type curable composition, and also a one pack type curable composition. In the latter case, the composition is prepared substantially in the absence of moisture, and can be stored stably for a long time, when it is stored in a sealed state. When the composition is exposed to an air after the storage, the curing of the composition starts from its surface.
- The composition of the present invention is useful as an elastic sealing material in the fields of building, construction and industries. It can be used as a coating, an adhesive, a caulking material, a coating material, and the like.
- The curable composition of the present invention will be explained more in detail by the following examples, which do not limit the present invention in any way.
- Surface treated glued calcium carbonate (average particle size of 0.08 μm) (120 wt. parts), titanium oxide (20 wt. parts), hydrogenated castor oil (2 wt. parts), dibutyltin diacetylacetonate (1 wt. part), and further a hydrocarbon shown in Table 1, DIDP (diisodecyl phthalate) or NEW POLE LB 285 (oxypropylene glycol monoether manufactured by SANYO CHEMICAL Co., Ltd.) in amounts shown in Table 1 were added to 100 wt. parts of a propylene oxide polymer having an average molecular weight of 8000 and two methyldimethoxysilyl groups [—Si(CH3)(OCH3)2] per one molecule on the average. Then, the mixture was thoroughly kneaded in an atmosphere containing substantially no moisture. Thus, a curable resin composition was obtained.
- In Table 1, octane, undecane and tridecane are supplied from WAKO JUNYAKU Co., Ltd., N-12 is normal paraffin (n-dodecane 99.0%) available from NIKKO PETROCHEMICALS, YH-NP is normal paraffins (n-dodecane: 18%, n-tridecane: 59%, n-tetradecane: 19%, and n-heptadecane: 4%) available from NIKKO PETROCHEMICALS, and SH-NP is normal paraffin (n-tetradecane: 5%, n-heptadecane: 37%, and n-hexadecane: 8%) available from NIKKO PETROCHEMICALS.
- The obtained composition was spread in a thickness of 3 mm and cured at 23° C., 55% RH. Then, the residual tack on the surface of the cured material was evaluated by finger touching after 1 day and 7 days. The results are shown in Table 1.
TABLE 1 Comp. Example Ex. No. 1 2 3 4 5 6 7 8 9 10 11 12 1 2 Hydrocarbon Octane 10 — — — — — — — — — — — — — Undecane — 10 — — — — 20 — 45 — — — — — Tridecane — — 10 — — — — 20 — — — — — — N-12 — — — 10 — — — — — 10 — — — — YH-NP — — — — 10 — — — — — 10 — — — SH-NP — — — — — 10 — — — — — 10 — — Plasticizer DIDP 45 45 45 45 45 45 35 35 10 — — — 55 — LB-285 — — — — — — — — — 45 45 45 — 55 Tack after 1 day C C C-B C C C C C C-B C C C D-C D-C 7 days B B B-A B B C-B B B A B B B C C - From the results in Table 1, it is understood that the addition of the paraffinic hydrocarbons to the oxyalkylene polymer can provide the cured materials having improved tack which remains on the surface.
- Surface treated glued calcium carbonate (average particle size of 0.08 μm) (120 wt. parts), titanium oxide (20 wt. parts), hydrogenated castor oil (2 wt. parts), dibutyltin diacetylacetonate (1 wt. part), and further a hydrocarbon shown in Table 2, KBM 3103C (CH3(CH2)9Si(OCH3)3 manufactured by SHINETSU SILICONE Co., Ltd.) or TSL 8185 (CH3(CH2)17Si(OCH3)3 manufactured by TOSHIBA SILICONE Co., Ltd.) and DIDP (diisodecyl phthalate) in amounts shown in Table 2 were added to 100 wt. parts of a propylene oxide polymer having an average molecular weight of 8000 and two methyldimethoxysilyl groups per one molecule on the average. Then, the mixture was thoroughly kneaded in an atmosphere containing substantially no moisture. Thus, a curable resin composition was obtained.
- In Table 2, undecane is supplied from WAKO JUNYAKU Co., Ltd., and YH-NP and SH-NP are the same as those in Table 1.
- The obtained composition was spread in a thickness of 3 mm and cured at 23° C., 55% RH. Then, the residual tack on the surface of the cured material was evaluated by finger touching after 1 day and 7 days. The results are shown in Table 2.
TABLE 2 Comp. Example No. Ex. No. 13 14 15 16 17 18 19 20 3 4 Hydrocarbon Undecane 5 5 — — — — 10 20 — — YH-NP — — 5 5 — — — — — — SH-NP — — — — 5 5 — — — — Silane compound KBM 3103C 5 — 5 — 5 — 5 5 5 — TSL 8185 — 5 — 5 — 5 — — — 5 Plasticizer DIDP 50 50 50 50 50 50 45 35 55 55 Tack after 1 day B B B B B B B-A A C C 7 days B-A B-A B-A B-A B-A B-A A A B C-B - From the results in Table 2, it is understood that the addition of the paraffinic hydrocarbons and silicon compounds having the long chain hydrocarbon group to the oxyalkylene polymer can provide the cured materials having improved tack which remains on the surface after one day from the start of curing.
Claims (8)
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP20446795A JP3676440B2 (en) | 1995-08-10 | 1995-08-10 | Curable composition |
JP7-204466 | 1995-08-10 | ||
JP204466/1995 | 1995-08-10 | ||
JP7-204467 | 1995-08-10 | ||
JP20446695A JP3637109B2 (en) | 1995-08-10 | 1995-08-10 | Curable resin composition |
PCT/JP1996/002249 WO1997006212A1 (en) | 1995-08-10 | 1996-08-08 | Curable polymer composition |
Publications (2)
Publication Number | Publication Date |
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US20010003763A1 true US20010003763A1 (en) | 2001-06-14 |
US6300404B2 US6300404B2 (en) | 2001-10-09 |
Family
ID=26514481
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US09/011,449 Expired - Lifetime US6300404B2 (en) | 1995-08-10 | 1996-08-08 | Curable polymer composition |
Country Status (6)
Country | Link |
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US (1) | US6300404B2 (en) |
EP (1) | EP0844282B1 (en) |
AU (1) | AU6669496A (en) |
CA (1) | CA2229048A1 (en) |
DE (1) | DE69617439T2 (en) |
WO (1) | WO1997006212A1 (en) |
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US20100022692A1 (en) * | 2006-12-26 | 2010-01-28 | Idemitsu Kosan Co., Ltd. | Plasticizer for resin and resin composition containing the same |
US20130142949A1 (en) * | 2011-12-02 | 2013-06-06 | Cpfilms Inc. | Catalysts for Thermal Cure Silicone Release Coatings |
US20130197141A1 (en) * | 2011-02-01 | 2013-08-01 | Henkel Ag & Co. Kgaa | Curable composition having combined stabilizers |
TWI555802B (en) * | 2011-12-02 | 2016-11-01 | Cp薄膜股份有限公司 | Catalysts for thermal cure silicone release coatings |
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WO2000037534A1 (en) * | 1998-12-22 | 2000-06-29 | Adco Products, Inc. | One component, moisture curable insulation adhesive |
US6668478B2 (en) * | 2000-12-01 | 2003-12-30 | Jason Bergstrom | Firearm pneumatic counter-recoil modulator & airgun thrust-adjustor |
US6596402B2 (en) † | 2000-12-29 | 2003-07-22 | Kimberly-Clark Worldwide, Inc. | Absorbent, lubricious coating and articles coated therewith |
US6664323B2 (en) * | 2001-02-02 | 2003-12-16 | General Electric Company | Moisture curable sealants |
WO2005007745A1 (en) * | 2003-07-18 | 2005-01-27 | Kaneka Corporation | Curable composition |
JP4885544B2 (en) * | 2003-11-19 | 2012-02-29 | 株式会社カネカ | Curable resin composition |
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- 1996-08-08 EP EP96926603A patent/EP0844282B1/en not_active Expired - Lifetime
- 1996-08-08 AU AU66694/96A patent/AU6669496A/en not_active Abandoned
- 1996-08-08 WO PCT/JP1996/002249 patent/WO1997006212A1/en active IP Right Grant
- 1996-08-08 CA CA002229048A patent/CA2229048A1/en not_active Abandoned
- 1996-08-08 DE DE69617439T patent/DE69617439T2/en not_active Expired - Lifetime
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100022692A1 (en) * | 2006-12-26 | 2010-01-28 | Idemitsu Kosan Co., Ltd. | Plasticizer for resin and resin composition containing the same |
US8017677B2 (en) | 2006-12-26 | 2011-09-13 | Idemitsu Kosan Co., Ltd. | Plasticizer for resin and resin composition containing the same |
US20130197141A1 (en) * | 2011-02-01 | 2013-08-01 | Henkel Ag & Co. Kgaa | Curable composition having combined stabilizers |
US9695297B2 (en) * | 2011-02-01 | 2017-07-04 | Henkel Ag & Co. Kgaa | Curable composition having combined stabilizers |
US20130142949A1 (en) * | 2011-12-02 | 2013-06-06 | Cpfilms Inc. | Catalysts for Thermal Cure Silicone Release Coatings |
US9469782B2 (en) * | 2011-12-02 | 2016-10-18 | Cpfilms Inc. | Catalysts for thermal cure silicone release coatings |
TWI555802B (en) * | 2011-12-02 | 2016-11-01 | Cp薄膜股份有限公司 | Catalysts for thermal cure silicone release coatings |
Also Published As
Publication number | Publication date |
---|---|
EP0844282A4 (en) | 1998-11-11 |
CA2229048A1 (en) | 1997-02-20 |
WO1997006212A1 (en) | 1997-02-20 |
DE69617439T2 (en) | 2002-08-08 |
AU6669496A (en) | 1997-03-05 |
EP0844282A1 (en) | 1998-05-27 |
EP0844282B1 (en) | 2001-11-28 |
US6300404B2 (en) | 2001-10-09 |
DE69617439D1 (en) | 2002-01-10 |
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