JP2022111452A - Room temperature-curable resin composition, coating agent, adhesive and sealing agent, and article - Google Patents
Room temperature-curable resin composition, coating agent, adhesive and sealing agent, and article Download PDFInfo
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- JP2022111452A JP2022111452A JP2021006885A JP2021006885A JP2022111452A JP 2022111452 A JP2022111452 A JP 2022111452A JP 2021006885 A JP2021006885 A JP 2021006885A JP 2021006885 A JP2021006885 A JP 2021006885A JP 2022111452 A JP2022111452 A JP 2022111452A
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- 239000011342 resin composition Substances 0.000 title claims abstract description 28
- 239000011248 coating agent Substances 0.000 title claims description 10
- 239000000853 adhesive Substances 0.000 title claims description 7
- 230000001070 adhesive effect Effects 0.000 title claims description 7
- 239000003795 chemical substances by application Substances 0.000 title description 5
- 238000007789 sealing Methods 0.000 title description 3
- -1 organosilane compound Chemical class 0.000 claims abstract description 69
- 125000003277 amino group Chemical group 0.000 claims abstract description 21
- 229920005573 silicon-containing polymer Polymers 0.000 claims abstract description 14
- 125000005372 silanol group Chemical group 0.000 claims abstract description 10
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 239000003054 catalyst Substances 0.000 claims description 14
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- 239000000945 filler Substances 0.000 claims description 7
- 239000004014 plasticizer Substances 0.000 claims description 6
- 239000000565 sealant Substances 0.000 claims description 6
- 239000002318 adhesion promoter Substances 0.000 claims description 4
- 239000011247 coating layer Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 abstract description 49
- 125000003118 aryl group Chemical group 0.000 abstract description 9
- 229920001971 elastomer Polymers 0.000 abstract description 8
- 230000009257 reactivity Effects 0.000 abstract description 6
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 229920001296 polysiloxane Polymers 0.000 description 14
- 238000001723 curing Methods 0.000 description 13
- 229920005645 diorganopolysiloxane polymer Polymers 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 229910000077 silane Inorganic materials 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical group 0.000 description 5
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- YGHWXXSYVWPXHA-UHFFFAOYSA-N n-[[dimethoxy(methyl)silyl]methyl]-n-ethylethanamine Chemical compound CCN(CC)C[Si](C)(OC)OC YGHWXXSYVWPXHA-UHFFFAOYSA-N 0.000 description 5
- KPIIDEIURMTGCD-UHFFFAOYSA-N n-ethyl-n-(trimethoxysilylmethyl)ethanamine Chemical compound CCN(CC)C[Si](OC)(OC)OC KPIIDEIURMTGCD-UHFFFAOYSA-N 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 4
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 4
- 230000001588 bifunctional effect Effects 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 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 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 4
- JQCXWCOOWVGKMT-UHFFFAOYSA-N diheptyl phthalate Chemical compound CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC JQCXWCOOWVGKMT-UHFFFAOYSA-N 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 125000004193 piperazinyl group Chemical group 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 4
- 125000001302 tertiary amino group Chemical group 0.000 description 4
- 125000003944 tolyl group Chemical group 0.000 description 4
- 125000005023 xylyl group Chemical group 0.000 description 4
- 239000004970 Chain extender Substances 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000006309 butyl amino group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000012188 paraffin wax Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 229920002545 silicone oil Polymers 0.000 description 3
- 229920002379 silicone rubber Polymers 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- ALKCLFLTXBBMMP-UHFFFAOYSA-N 3,7-dimethylocta-1,6-dien-3-yl hexanoate Chemical compound CCCCCC(=O)OC(C)(C=C)CCC=C(C)C ALKCLFLTXBBMMP-UHFFFAOYSA-N 0.000 description 2
- GPZYYYGYCRFPBU-UHFFFAOYSA-N 6-Hydroxyflavone Chemical compound C=1C(=O)C2=CC(O)=CC=C2OC=1C1=CC=CC=C1 GPZYYYGYCRFPBU-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 2
- VOWAEIGWURALJQ-UHFFFAOYSA-N Dicyclohexyl phthalate Chemical compound C=1C=CC=C(C(=O)OC2CCCCC2)C=1C(=O)OC1CCCCC1 VOWAEIGWURALJQ-UHFFFAOYSA-N 0.000 description 2
- 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 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
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical group NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- 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 2
- GTVWRXDRKAHEAD-UHFFFAOYSA-N Tris(2-ethylhexyl) phosphate Chemical compound CCCCC(CC)COP(=O)(OCC(CC)CCCC)OCC(CC)CCCC GTVWRXDRKAHEAD-UHFFFAOYSA-N 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000013466 adhesive and sealant Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- ZDWGXBPVPXVXMQ-UHFFFAOYSA-N bis(2-ethylhexyl) nonanedioate Chemical compound CCCCC(CC)COC(=O)CCCCCCCC(=O)OCC(CC)CCCC ZDWGXBPVPXVXMQ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 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 2
- JBSLOWBPDRZSMB-BQYQJAHWSA-N dibutyl (e)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C\C(=O)OCCCC JBSLOWBPDRZSMB-BQYQJAHWSA-N 0.000 description 2
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 2
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 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
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 2
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- 229960001826 dimethylphthalate Drugs 0.000 description 2
- MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- YCZJVRCZIPDYHH-UHFFFAOYSA-N ditridecyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCCCCC YCZJVRCZIPDYHH-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
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 2
- 125000003916 ethylene diamine group Chemical group 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 229910021485 fumed silica Inorganic materials 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical group NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001245 hexylamino group Chemical group [H]N([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- KFRKZCBSQCUBFP-UHFFFAOYSA-N n-propyl-n-(trimethoxysilylmethyl)propan-1-amine Chemical compound CCCN(CCC)C[Si](OC)(OC)OC KFRKZCBSQCUBFP-UHFFFAOYSA-N 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001400 nonyl 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])[H] 0.000 description 2
- YAFOVCNAQTZDQB-UHFFFAOYSA-N octyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCCCC)OC1=CC=CC=C1 YAFOVCNAQTZDQB-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl 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])[H] 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000004894 pentylamino group Chemical group C(CCCC)N* 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 125000006308 propyl amino group Chemical group 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 239000004945 silicone rubber Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 150000004992 toluidines Chemical group 0.000 description 2
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
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- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- WEAPVABOECTMGR-UHFFFAOYSA-N triethyl 2-acetyloxypropane-1,2,3-tricarboxylate Chemical compound CCOC(=O)CC(C(=O)OCC)(OC(C)=O)CC(=O)OCC WEAPVABOECTMGR-UHFFFAOYSA-N 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
- GTRSAMFYSUBAGN-UHFFFAOYSA-N tris(2-chloropropyl) phosphate Chemical compound CC(Cl)COP(=O)(OCC(C)Cl)OCC(C)Cl GTRSAMFYSUBAGN-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Silicon Polymers (AREA)
Abstract
Description
本発明は、シロキサン結合を形成することにより架橋し得るケイ素含有基（以下、「反応性ケイ素含有基」とも称す。）として、ケイ素原子に結合した水酸基（即ち、シラノール基）又は加水分解性シリル基を分子鎖両末端に有するシリコーンポリマー（オルガノポリシロキサン）を主剤として含有する室温硬化性樹脂組成物（室温硬化性オルガノポリシロキサン組成物）に関するものである。また、該室温硬化性樹脂組成物からなるコーティング剤、接着剤及びシーリング剤、並びに該室温硬化性樹脂組成物の硬化物でコーティング、接着及びシールの少なくともいずれかを施した物品に関する。 The present invention provides a silicon-bonded hydroxyl group (i.e., a silanol group) or a hydrolyzable silyl The present invention relates to a room-temperature-curable resin composition (room-temperature-curable organopolysiloxane composition) containing, as a main component, a silicone polymer (organopolysiloxane) having groups at both ends of its molecular chain. The present invention also relates to coating agents, adhesives and sealants comprising the room temperature curable resin composition, and articles coated, bonded and/or sealed with a cured product of the room temperature curable resin composition.
反応性ケイ素含有基、特に加水分解性シリル基は、水在下にて加水分解縮合する性質を有していることから、この反応性ケイ素含有基を有するポリマーは、大気中の水又は湿気の存在下で室温（２３℃±１５℃）において架橋硬化する種々の室温硬化性樹脂組成物に用いることができる。 Reactive silicon-containing groups, particularly hydrolyzable silyl groups, have the property of undergoing hydrolytic condensation in the presence of water. It can be used in various room temperature curable resin compositions that crosslink and cure at room temperature (23° C.±15° C.).
これらのポリマーの中でも、その主鎖がケイ素含有構造（特に、好ましくは直鎖状のオルガノポリシロキサン構造）であるものは、一般的にシリコーンポリマーとして知られている。これらのシリコーンポリマーを主剤（ベースシリコーンポリマー）として用いた室温硬化性（ＲＴＶ）オルガノポリシロキサン組成物は、室温（２３℃±１５℃）では液状であり、硬化（架橋反応）によりシリコーンゴム弾性体（シリコーンエラストマー）となる特徴を有しており、その特徴を利用してコーティング剤、接着剤、建築用シーリング剤等に広く用いられている。これらの室温硬化性（ＲＴＶ）オルガノポリシロキサン樹脂組成物には、架橋剤及び安定化剤として、加水分解性オルガノシラン化合物やその部分加水分解縮合物等が使用されている。特に１分子中に二つの加水分解性基をもつ２官能性の加水分解性オルガノシラン化合物は架橋剤の中でも鎖長延長剤と呼ばれ、主剤（ベースシリコーンポリマー）の鎖長を伸ばすことでシーリング剤やＲＴＶゴム硬化物に適度な伸びを与える。 Among these polymers, those whose main chain is a silicon-containing structure (preferably a linear organopolysiloxane structure) are generally known as silicone polymers. Room temperature vulcanizable (RTV) organopolysiloxane compositions using these silicone polymers as the main component (base silicone polymer) are liquid at room temperature (23°C ± 15°C), and cure (crosslinking reaction) to form a silicone rubber elastomer. (silicone elastomer) and is widely used in coating agents, adhesives, building sealants, etc. Hydrolyzable organosilane compounds and partially hydrolyzed condensates thereof are used as crosslinking agents and stabilizers in these room temperature curable (RTV) organopolysiloxane resin compositions. In particular, bifunctional hydrolyzable organosilane compounds with two hydrolyzable groups in one molecule are called chain extenders among cross-linking agents, and seal by extending the chain length of the base silicone polymer. Appropriate elongation is given to agents and RTV rubber cured products.
室温硬化性（ＲＴＶ）オルガノポリシロキサン組成物は、種々のタイプのものが公知である。とりわけ架橋時の加水分解・縮合反応によりアルコールを放出して硬化する脱アルコールタイプのものは不快臭がない、金属類を腐食しないという特徴により、電気・電子機器等のシーリング用、接着用、コーティング用に好んで使用されている（特許文献１及び２）。 Various types of room temperature vulcanizable (RTV) organopolysiloxane compositions are known. In particular, the dealcoholized type, which cures by releasing alcohol through hydrolysis and condensation reactions during cross-linking, has no unpleasant odor and does not corrode metals. (Patent Documents 1 and 2).
しかしながら、脱アルコールタイプのものは従来公知の他の硬化タイプである脱アセトンタイプ、脱オキシムタイプ、脱アミノキシタイプ等のものと比較すると、大気中の水（湿気）との反応性が低く、硬化速度が遅いことから、これまで工業的に実用可能な脱アルコールタイプの室温硬化性（ＲＴＶ）組成物においてシリコーンポリマー（主剤）の鎖長延長剤となる加水分解性オルガノシラン化合物はなく、それらを含む組成物もなかった。 However, the dealcoholized type has lower reactivity with atmospheric water (humidity) than other known curing types such as the deacetone type, the oxime type, and the deaminoxy type. Due to its slow curing speed, there have been no hydrolyzable organosilane compounds that can be used as chain extenders for silicone polymers (base ingredients) in commercially available dealcoholization type room temperature vulcanizing (RTV) compositions. There were also no compositions containing
したがって、本発明は、反応性が高く、速やかにゴム化し、鎖長延長効果により適度な伸びを発現する加水分解性オルガノシラン化合物を含有する室温硬化性樹脂組成物、該室温硬化性樹脂組成物からなるコーティング剤、接着剤及びシーリング剤、並びに該室温硬化性樹脂組成物の硬化物でコーティング、接着及びシールの少なくともいずれかを施した物品を提供することを目的とする。 Accordingly, the present invention provides a room-temperature-curable resin composition containing a hydrolyzable organosilane compound that exhibits high reactivity, rapidly rubberizes, and exhibits moderate elongation due to the effect of chain elongation, and the room-temperature-curable resin composition. The object is to provide a coating agent, an adhesive and a sealant, and an article subjected to at least one of coating, adhesion and sealing with a cured product of the room temperature curable resin composition.
本発明者らは、上記目的を達成するために鋭意研究した結果、下記一般式（１）、（２）で表される２種類（２官能性及び３官能性）の特定のアミノ基及び／又はアミン残基で置換されたメチレン基を有する特定のオルガノポリシロキサン化合物を併用して組成物中に配合することが、上述した課題の解決に有用であることを見出し、本発明を完成した。 The present inventors have made intensive studies to achieve the above objects, and found that two types (bifunctional and trifunctional) of specific amino groups represented by the following general formulas (1) and (2) and / Alternatively, the present inventors have found that it is useful to solve the above-described problems by combining a specific organopolysiloxane compound having a methylene group substituted with an amine residue and blending it in the composition, and completed the present invention.
即ち、本発明は、下記の室温硬化性樹脂組成物（具体的には、コーティング剤、接着剤及びシーリング剤）、並びに該組成物の硬化物を有する物品等を提供するものである。 That is, the present invention provides the following room-temperature-curable resin compositions (specifically, coating agents, adhesives and sealants), articles and the like comprising cured products of the compositions.
［１］
（Ａ）分子鎖両末端がシラノール基又は加水分解性シリル基で封鎖されたシリコーンポリマー：１００質量部、
（Ｂ）下記の式（１）で表されるオルガノシラン化合物：０．００１～３０質量部、
（Ｃ）下記の式（２）で表されるオルガノシラン化合物：０．００１～３０質量部、
を含有するものである室温硬化性樹脂組成物。
［２］
更に、（Ａ）成分１００質量部に対して、
（Ｄ）硬化触媒：０．００１～２０質量部
（Ｅ）充填剤：１～１，０００質量部
（Ｆ）接着促進剤：０．１～３０質量部
（Ｇ）可塑剤：１～１，０００質量部
から選ばれる１種又は２種以上の成分を含有する［１］に記載の室温硬化性樹脂組成物。
［３］
［１］又は［２］に記載の室温硬化性樹脂組成物からなるコーティング剤。
［４］
［１］又は［２］に記載の室温硬化性樹脂組成物からなる接着剤。
［５］
［１］又は［２］に記載の室温硬化性樹脂組成物からなるシーリング剤。
［６］
［１］又は［２］に記載の室温硬化性樹脂組成物の硬化物からなる被覆層を有する物品。
［７］
［１］又は［２］に記載の室温硬化性樹脂組成物の硬化物で接着及び／又はシールされた物品。
[1]
(A) a silicone polymer having both molecular chain ends blocked with silanol groups or hydrolyzable silyl groups: 100 parts by mass;
(B) an organosilane compound represented by the following formula (1): 0.001 to 30 parts by mass;
(C) an organosilane compound represented by the following formula (2): 0.001 to 30 parts by mass,
A room temperature curable resin composition containing
[2]
Furthermore, with respect to 100 parts by mass of component (A),
(D) Curing catalyst: 0.001 to 20 parts by mass (E) Filler: 1 to 1,000 parts by mass (F) Adhesion promoter: 0.1 to 30 parts by mass (G) Plasticizer: 1 to 1, The room temperature curable resin composition according to [1], containing one or more components selected from 000 parts by mass.
[3]
A coating agent comprising the room-temperature-curable resin composition according to [1] or [2].
[4]
An adhesive comprising the room temperature curable resin composition according to [1] or [2].
[5]
A sealant comprising the room-temperature-curable resin composition according to [1] or [2].
[6]
An article having a coating layer comprising a cured product of the room-temperature-curable resin composition according to [1] or [2].
[7]
An article adhered and/or sealed with a cured product of the room temperature curable resin composition according to [1] or [2].
本発明の室温硬化性樹脂組成物は、２種類（２官能性及び３官能性）の特定のアミノ基及び／又はアミン残基で置換されたメチレン基を有する特定のオルガノシラン化合物が配合されていることにより、極めて速やかに硬化し、ゴム硬化物に適度な伸びを発現するという効果を有する。 The room-temperature-curable resin composition of the present invention contains two types (bifunctional and trifunctional) of specific organosilane compounds having methylene groups substituted with specific amino groups and/or amine residues. Due to the presence of the rubber, it cures extremely quickly, and has the effect of exhibiting appropriate elongation in the cured rubber.
以下、本発明につき更に詳しく説明する。 The present invention will be described in more detail below.
（Ａ）成分
本発明に用いられる（Ａ）成分は、分子鎖両末端がシラノール基（ケイ素原子に結合した水酸基）又は、トリアルコキシシリル基やジアルコキシオルガノシリル基などのアルコキシシリル基等の加水分解性シリル基で封鎖されたシリコーンポリマー（主剤）である。
(A) Component The (A) component used in the present invention has both ends of the molecular chain containing silanol groups (hydroxyl groups bonded to silicon atoms) or alkoxysilyl groups such as trialkoxysilyl groups and dialkoxyorganosilyl groups. It is a silicone polymer (main ingredient) blocked with degradable silyl groups.
（Ａ）成分のシリコーンポリマーとしては、具体的には、下記式（３）又は（４）で表される分子鎖両末端がシラノール基又は加水分解性シリル基で封鎖された直鎖状ジオルガノポリシロキサンが好ましいものとして挙げられる。
なお、粘度は回転粘度計（例えば、ＢＬ型、ＢＨ型、ＢＳ型、コーンプレート型等）による数値である（以下、同じ。）。また、上記式（３）又は（４）で示されるジオルガノポリシロキサン中におけるジオルガノシロキサン単位の繰り返し数（ｍ）又は重合度は、トルエン等を展開溶媒としてゲルパーミエーションクロマトグラフィ（ＧＰＣ）分析におけるポリスチレン換算の数平均重合度（又は数平均分子量）等として求めたものである。
Specifically, the silicone polymer of component (A) is a straight-chain diorgano polymer represented by the following formula (3) or (4) in which both ends of the molecular chain are blocked with silanol groups or hydrolyzable silyl groups. Polysiloxanes are preferred.
The viscosity is a numerical value obtained by a rotational viscometer (for example, BL type, BH type, BS type, cone plate type, etc.) (hereinafter the same). In addition, the number of repeating diorganosiloxane units (m) or the degree of polymerization in the diorganopolysiloxane represented by the above formula (3) or (4) is determined by gel permeation chromatography (GPC) analysis using toluene or the like as a developing solvent. It is obtained as a polystyrene-equivalent number-average degree of polymerization (or number-average molecular weight).
上記式（３）及び（４）において、Ｒ3の非置換もしくは置換の炭素原子数１～１２のアルキル基又は非置換もしくは置換の炭素原子数６～１０のアリール基としては、メチル基、エチル基、ｎ－プロピル基、イソプロピル基、ブチル基、イソブチル基、ｔｅｒｔ－ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ノニル基、デシル基、ドデシル基等のアルキル基；シクロペンチル基、シクロヘキシル基等のシクロアルキル基；フェニル基、トリル基、キシリル基、α－，β－ナフチル基等のアリール基；また、これらの基の水素原子の一部又は全部が、Ｆ、Ｃｌ、Ｂｒ等のハロゲン原子やシアノ基等で置換された基、例えば、３－クロロプロピル基、３，３，３－トリフルオロプロピル基、２－シアノエチル基等を例示することができる。これらの中でも、メチル基、エチル基等のアルキル基が好ましく、メチル基が特に好ましい。 In the above formulas (3) and (4), the unsubstituted or substituted alkyl group having 1 to 12 carbon atoms or the unsubstituted or substituted aryl group having 6 to 10 carbon atoms for R 3 includes methyl group, ethyl Alkyl groups such as group, n-propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, dodecyl group; cyclopentyl group, cyclohexyl cycloalkyl groups such as groups; phenyl groups, tolyl groups, xylyl groups, α-, β-naphthyl groups and other aryl groups; Examples include groups substituted with halogen atoms, cyano groups, etc., such as 3-chloropropyl group, 3,3,3-trifluoropropyl group, 2-cyanoethyl group and the like. Among these, alkyl groups such as methyl group and ethyl group are preferred, and methyl group is particularly preferred.
上記式（３）及び（４）において、Ｙは酸素原子又は炭素数１～８の二価炭化水素基であり、－（ＣＨ2ＣＨ2）q－、又は－（ＣＨ＝ＣＨ）q－（ｑは１～４を表す）であることが好ましい。これらの中でも特に酸素原子、－ＣＨ2ＣＨ2－、又は－ＣＨ＝ＣＨ－が好ましい。 In the above formulas (3) and (4), Y is an oxygen atom or a divalent hydrocarbon group having 1 to 8 carbon atoms, and -(CH 2 CH 2 ) q - or -(CH=CH) q -( q represents 1 to 4). Among these, an oxygen atom, -CH 2 CH 2 -, or -CH=CH- is particularly preferred.
上記式（４）において、Ｚは加水分解性基であり、例えば、メトキシ基、エトキシ基、プロポキシ基等のアルコキシ基；メトキシエトキシ基、エトキシエトキシ基、メトキシプロポキシ基等のアルコキシアルコキシ基；アセトキシ基、オクタノイルオキシ基、ベンゾイルオキシ基等のアシロキシ基；ビニロキシ基、アリルオキシ基、プロペニルオキシ基、イソプロペニルオキシ基、１－エチル－２－メチルビニルオキシ基等のアルケニルオキシ基；ジメチルケトオキシム基、メチルエチルケトオキシム基、ジエチルケトオキシム基等のケトオキシム基；ジメチルアミノ基、ジエチルアミノ基、ブチルアミノ基、シクロヘキシルアミノ基等のアミノ基；ジメチルアミノキシ基、ジエチルアミノキシ基等のアミノキシ基；Ｎ－メチルアセトアミド基、Ｎ－エチルアセトアミド基、Ｎ－メチルベンズアミド基等のアミド基等が挙げられる。この中でも、アルコキシ基が好ましく、特には、メトキシ基、エトキシ基及びプロポキシ基がより好ましい。 In the above formula (4), Z is a hydrolyzable group, for example, an alkoxy group such as a methoxy group, an ethoxy group, and a propoxy group; an alkoxyalkoxy group such as a methoxyethoxy group, an ethoxyethoxy group, and a methoxypropoxy group; , octanoyloxy group, acyloxy group such as benzoyloxy group; vinyloxy group, allyloxy group, propenyloxy group, isopropenyloxy group, alkenyloxy group such as 1-ethyl-2-methylvinyloxy group; dimethylketoxime group, ketoxime groups such as methylethylketoxime group and diethylketoxime group; amino groups such as dimethylamino group, diethylamino group, butylamino group and cyclohexylamino group; aminoxy groups such as dimethylaminoxy group and diethylaminoxy group; N-methylacetamide group , an N-ethylacetamide group, an amide group such as an N-methylbenzamide group, and the like. Among these, an alkoxy group is preferable, and a methoxy group, an ethoxy group and a propoxy group are more preferable.
上記式（３）又は（４）で表される直鎖状ジオルガノポリシロキサンの構造としては、例えば、分子鎖両末端シラノール基封鎖ジオルガノポリシロキサン、分子鎖両末端ジオルガノヒドロキシシリルエチル基封鎖ジオルガノポリシロキサン、分子鎖両末端ジオルガノヒドロキシシリルプロピル基封鎖ジオルガノポリシロキサン、分子鎖両末端トリアルコキシシロキシ基封鎖ジオルガノポリシロキサン、分子鎖両末端ジアルコキシオルガノシロキシ基封鎖ジオルガノポリシロキサン、分子鎖両末端トリアルコキシシリルエチル基封鎖ジオルガノポリシロキサン、分子鎖両末端トリアルコキシシリルプロピル基封鎖ジオルガノポリシロキサン、分子鎖両末端ジアルコキシオルガノシリルエチル基封鎖ジオルガノポリシロキサン、分子鎖両末端ジアルコキシオルガノシリルプロピル基封鎖ジオルガノポリシロキサン等が挙げられる。 Examples of the structure of the linear diorganopolysiloxane represented by the above formula (3) or (4) include diorganopolysiloxane blocked with silanol groups at both ends of the molecular chain and diorganohydroxysilylethyl groups blocked at both ends of the molecular chain. diorganopolysiloxane, diorganopolysiloxane blocked with diorganohydroxysilylpropyl groups at both molecular chain terminals, diorganopolysiloxane blocked with trialkoxysiloxy groups at both molecular chain terminals, diorganopolysiloxane blocked with dialkoxyorganosiloxy groups at both molecular chain terminals, Diorganopolysiloxane blocked with trialkoxysilylethyl groups at both molecular chain ends, diorganopolysiloxane blocked with trialkoxysilylpropyl groups at both ends of the molecular chain, diorganopolysiloxane blocked with dialkoxyorganosilylethyl groups at both ends of the molecular chain, both ends of the molecular chain dialkoxyorganosilylpropyl group-blocked diorganopolysiloxane;
（Ａ）成分の分子鎖両末端がシラノール基又は加水分解性シリル基で封鎖されたシリコーンポリマーは、１種単独でも構造や重合度の異なる２種以上を組み合わせても使用してもよい。 The silicone polymers of component (A) having both molecular chain ends blocked with silanol groups or hydrolyzable silyl groups may be used singly or in combination of two or more with different structures and degrees of polymerization.
（Ｂ）成分
本発明の組成物は、下記式（１）で表される、ケイ素原子上にアミノ基及び／又はアミン残基で置換されたメチレン基を有すると共に、同一のケイ素原子上に直接結合した２個のオルガノキシ基（例えば、メトキシ基、エトキシ基等）を有する２官能性の加水分解性オルガノシラン化合物を含むものであり、（Ｂ）成分のアミノ基及び／又はアミン残基で置換されたメチレン基を有するオルガノシラン化合物は、本発明の組成物中において、（Ｂ）成分中のケイ素原子に直接結合した２個のオルガノキシ基が（Ａ）成分のシリコーンポリマーの両末端に存在するシラノール基又は加水分解性シリル基と縮合反応してＳｉ－Ｏ－Ｓｉ結合（シロキサン結合）を形成することによって（Ａ）成分のシリコーンポリマーの鎖長を延長する鎖長延長剤として作用するものである。
式（１）中、Ｒ1及びＲ2は、それぞれ独立して非置換もしくは置換の炭素原子数１～１２のアルキル基又は非置換もしくは置換の炭素原子数６～１０のアリール基を表す。上記Ｒ1及びＲ2において、炭素原子数１～１２のアルキル基としては、直鎖状、環状、分枝状のいずれでもよく、その具体例としては、メチル、エチル、ｎ－プロピル、ｉ－プロピル、ｎ－ブチル、ｓ－ブチル、ｔ－ブチル、ｎ－ペンチル、ネオペンチル、ｎ－ヘキシル、ｎ－ヘプチル、ｎ－オクチル、ｎ－ノニル、ｎ－デシル基、ｎ－ドデシル基等の直鎖又は分岐鎖アルキル基；シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、シクロヘプチル、シクロオクチル、イソボルニル基等のシクロアルキル基が挙げられる。また、炭素原子数６～１０のアリール基の具体例としては、フェニル、トリル、キシリル、α－ナフチル、β－ナフチル基等が挙げられる。なお、これらの基の水素原子の一部又は全部は、アルキル基、アリール基、Ｆ、Ｃｌ、Ｂｒ等のハロゲン原子やシアノ基等で置換されていてもよく、これらの中でも、Ｒ1及びＲ2としては、メチル基、エチル基等のアルキル基、フェニル基が好ましく、反応性や入手の容易さ、生産性、コストの面からメチル基がより好ましい。 In formula (1), R 1 and R 2 each independently represent an unsubstituted or substituted alkyl group having 1 to 12 carbon atoms or an unsubstituted or substituted aryl group having 6 to 10 carbon atoms. In R 1 and R 2 above, the alkyl group having 1 to 12 carbon atoms may be linear, cyclic or branched, and specific examples include methyl, ethyl, n-propyl, i- Linear or Branched-chain alkyl groups; cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and isobornyl groups. Specific examples of aryl groups having 6 to 10 carbon atoms include phenyl, tolyl, xylyl, α-naphthyl, β-naphthyl groups and the like. Incidentally, some or all of the hydrogen atoms in these groups may be substituted with an alkyl group, an aryl group, a halogen atom such as F, Cl, or Br, or a cyano group. 2 is preferably a methyl group, an alkyl group such as an ethyl group, or a phenyl group, and more preferably a methyl group in terms of reactivity, availability, productivity and cost.
上記一般式（１）において、Ｘは非置換又は置換のアミノ基であり、２級又は３級アミノ基（例えば、モノオルガノ置換アミノ基又はジオルガノ置換アミノ基）が好ましく、３級アミノ基（例えば、ジオルガノ置換アミノ基）がより好ましく、その具体例としては、メチルアミノ基、ジメチルアミノ基、エチルアミノ基、ジエチルアミノ基、プロピルアミノ基、イソプロピルアミノ基、ジプロピルアミノ基、ジイソプロピルアミノ基、ブチルアミノ基、イソブチルアミノ基、ｓｅｃ－ブチルアミノ基、ｔｅｒｔ－ブチルアミノ基、ジブチルアミノ基、ジイソブチルアミノ基、ジｓｅｃ－ブチルアミノ基、ジｔｅｒｔ－ブチルアミノ基、ペンチルアミノ基、ヘキシルアミノ基、ヘプチルアミノ基、オクチルアミノ基、ノニルアミノ基、エチレンジアミン残基、ヘキサメチレンジアミン残基、アニリン残基、フェネチルアミン残基、トルイジン残基、ピロリジン残基、ピペリジン残基、ピペラジン残基、モルホリン残基、ピロール残基、ピラゾール残基、イミダゾール残基等が挙げられる。特にジメチルアミノ基、ジエチルアミノ基や、ピロリジン残基、ピペラジン残基のような炭素数が少なく、合成時に反応しやすいものが好ましい。 In the general formula (1), X is an unsubstituted or substituted amino group, preferably a secondary or tertiary amino group (e.g., monoorgano-substituted amino group or diorgano-substituted amino group), a tertiary amino group (e.g., , a diorgano-substituted amino group) are more preferable, and specific examples thereof include a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a propylamino group, an isopropylamino group, a dipropylamino group, a diisopropylamino group, and a butylamino group. group, isobutylamino group, sec-butylamino group, tert-butylamino group, dibutylamino group, diisobutylamino group, disec-butylamino group, ditert-butylamino group, pentylamino group, hexylamino group, heptylamino group, octylamino group, nonylamino group, ethylenediamine residue, hexamethylenediamine residue, aniline residue, phenethylamine residue, toluidine residue, pyrrolidine residue, piperidine residue, piperazine residue, morpholine residue, pyrrole residue , pyrazole residue, imidazole residue and the like. In particular, dimethylamino group, diethylamino group, pyrrolidine residue, and piperazine residue, which have a small number of carbon atoms and are easily reactive during synthesis, are preferred.
（Ｂ）成分のオルガノシラン化合物は１種単独で使用してもよく、２種以上を併用してもよい。
（Ｂ）成分の配合量は、（Ａ）成分１００質量部に対して０．００１～３０質量部、好ましくは０．０１～２０質量部、より好ましくは０．１～１０質量部である。
The (B) component organosilane compound may be used alone or in combination of two or more.
Component (B) is added in an amount of 0.001 to 30 parts by mass, preferably 0.01 to 20 parts by mass, more preferably 0.1 to 10 parts by mass per 100 parts by mass of component (A).
（Ｃ）成分
本発明の組成物は、下記式（２）で表される、ケイ素原子上にアミノ基及び／又はアミン残基で置換されたメチレン基を有すると共に、同一のケイ素原子上に直接結合した３個のオルガノキシ基（例えば、メトキシ基、エトキシ基等）を有する３官能性の加水分解性オルガノシラン化合物を含むものであり、（Ｃ）成分のシラン化合物は、本発明の組成物中において、組成物を速やかに架橋、硬化する硬化剤（架橋剤）として作用する。
式（２）中、Ｒ2は、それぞれ独立して非置換もしくは置換の炭素原子数１～１２のアルキル基又は非置換もしくは置換の炭素原子数６～１０のアリール基を表す。上記Ｒ2において、炭素原子数１～１２のアルキル基としては、直鎖状、環状、分枝状のいずれでもよく、その具体例としては、メチル、エチル、ｎ－プロピル、ｉ－プロピル、ｎ－ブチル、ｓ－ブチル、ｔ－ブチル、ｎ－ペンチル、ネオペンチル、ｎ－ヘキシル、ｎ－ヘプチル、ｎ－オクチル、ｎ－ノニル、ｎ－デシル基、ｎ－ドデシル基等の直鎖又は分岐鎖アルキル基；シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、シクロヘプチル、シクロオクチル、イソボルニル基等のシクロアルキル基が挙げられる。また、炭素原子数６～１０のアリール基の具体例としては、フェニル、トリル、キシリル、α－ナフチル、β－ナフチル基等が挙げられる。なお、これらの基の水素原子の一部又は全部は、アルキル基、アリール基、Ｆ、Ｃｌ、Ｂｒ等のハロゲン原子やシアノ基等で置換されていてもよく、これらの中でも、Ｒ2としては、メチル基、エチル基等のアルキル基、フェニル基が好ましく、反応性や入手の容易さ、生産性、コストの面からメチル基がより好ましい。 In formula (2), each R 2 independently represents an unsubstituted or substituted alkyl group having 1 to 12 carbon atoms or an unsubstituted or substituted aryl group having 6 to 10 carbon atoms. In R 2 , the alkyl group having 1 to 12 carbon atoms may be linear, cyclic or branched, and specific examples include methyl, ethyl, n-propyl, i-propyl, n -Linear or branched chain alkyl such as butyl, s-butyl, t-butyl, n-pentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl group, n-dodecyl group, etc. Groups: Cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and isobornyl groups. Specific examples of aryl groups having 6 to 10 carbon atoms include phenyl, tolyl, xylyl, α-naphthyl, β-naphthyl groups and the like. Some or all of the hydrogen atoms in these groups may be substituted with alkyl groups, aryl groups, halogen atoms such as F, Cl , and Br, cyano groups, and the like. Alkyl groups such as , methyl and ethyl groups, and phenyl groups are preferable, and a methyl group is more preferable from the viewpoints of reactivity, availability, productivity and cost.
上記一般式（２）において、Ｘは非置換又は置換のアミノ基であり、２級又は３級アミノ基（例えば、モノオルガノ置換アミノ基又はジオルガノ置換アミノ基）が好ましく、３級アミノ基（例えば、ジオルガノ置換アミノ基）がより好ましく、その具体例としては、メチルアミノ基、ジメチルアミノ基、エチルアミノ基、ジエチルアミノ基、プロピルアミノ基、イソプロピルアミノ基、ジプロピルアミノ基、ジイソプロピルアミノ基、ブチルアミノ基、イソブチルアミノ基、ｓｅｃ－ブチルアミノ基、ｔｅｒｔ－ブチルアミノ基、ジブチルアミノ基、ジイソブチルアミノ基、ジｓｅｃ－ブチルアミノ基、ジｔｅｒｔ－ブチルアミノ基、ペンチルアミノ基、ヘキシルアミノ基、ヘプチルアミノ基、オクチルアミノ基、ノニルアミノ基、エチレンジアミン残基、ヘキサメチレンジアミン残基、アニリン残基、フェネチルアミン残基、トルイジン残基、ピロリジン残基、ピペリジン残基、ピペラジン残基、モルホリン残基、ピロール残基、ピラゾール残基、イミダゾール残基等が挙げられる。特にジメチルアミノ基、ジエチルアミノ基や、ピロリジン残基、ピペラジン残基のような炭素数が少なく、合成時に反応しやすいものが好ましい。 In the general formula (2), X is an unsubstituted or substituted amino group, preferably a secondary or tertiary amino group (e.g., monoorgano-substituted amino group or diorgano-substituted amino group), a tertiary amino group (e.g., , a diorgano-substituted amino group) are more preferable, and specific examples thereof include a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a propylamino group, an isopropylamino group, a dipropylamino group, a diisopropylamino group, and a butylamino group. group, isobutylamino group, sec-butylamino group, tert-butylamino group, dibutylamino group, diisobutylamino group, disec-butylamino group, ditert-butylamino group, pentylamino group, hexylamino group, heptylamino group, octylamino group, nonylamino group, ethylenediamine residue, hexamethylenediamine residue, aniline residue, phenethylamine residue, toluidine residue, pyrrolidine residue, piperidine residue, piperazine residue, morpholine residue, pyrrole residue , pyrazole residue, imidazole residue and the like. In particular, dimethylamino group, diethylamino group, pyrrolidine residue, and piperazine residue, which have a small number of carbon atoms and are easily reactive during synthesis, are preferred.
（Ｃ）成分の配合量は、上記（Ａ）成分１００質量部に対して０．００１～３０質量部であり、０．０１～１０質量部が好ましく、０．１～５質量部がより好ましい。（Ｃ）成分の配合量が少なすぎると十分な硬化性が得られず、多すぎると硬化性が速すぎる結果、十分な作業時間が得られず、また経済的に不利となる場合がある。
なお、（Ｂ）成分と（Ｃ）成分の配合比は、質量比率で（Ｂ）成分：（Ｃ）成分が、１：１００～１００：１が好ましく、１：１０～１０：１がより好ましく、１：１～５：１がさらに好ましい。
The amount of component (C) is 0.001 to 30 parts by mass, preferably 0.01 to 10 parts by mass, more preferably 0.1 to 5 parts by mass, per 100 parts by mass of component (A). . If the amount of component (C) is too small, sufficient curability cannot be obtained, and if it is too large, the curability will be too fast, resulting in insufficient working time and economic disadvantages.
The mixing ratio of component (B) and component (C) is preferably 1:100 to 100:1, more preferably 1:10 to 10:1, in mass ratio of component (B):component (C). , 1:1 to 5:1 are more preferred.
（Ｄ）成分
本発明の組成物で用いられる（Ｄ）成分は、硬化触媒（非金属系有機触媒及び／又は金属系触媒）であり、本発明の組成物に必要に応じて配合できる任意成分であり、本発明の室温硬化性樹脂組成物の硬化を更に促進するために使用するためのものである。
Component (D) Component (D) used in the composition of the present invention is a curing catalyst (non-metallic organic catalyst and/or metal catalyst), and an optional component that can be blended into the composition of the present invention as necessary. and is intended to be used to further accelerate the curing of the room temperature curable resin composition of the present invention.
該硬化触媒の非金属系有機触媒としては、縮合硬化型オルガノポリシロキサン組成物の硬化促進剤として公知のものを使用することができ、特に制限されるものではない。例えば、Ｎ，Ｎ，Ｎ’，Ｎ’，Ｎ’’，Ｎ’’－ヘキサメチル－Ｎ’’’－（トリメチルシリルメチル）－ホスホリミディックトリアミド等のホスファゼン含有化合物、ｎ－オクチルアミン、ヘキシルアミン、リン酸ドデシルアミン、テトラメチルグアニジン等のアミン化合物又はその塩、ベンジルトリエチルアンモニウムアセテート等の第４級アンモニウム塩、ジメチルヒドロキシルアミン、ジエチルヒドロキシルアミン等のジアルキルヒドロキシルアミン、テトラメチルグアニジルプロピルトリメトキシシラン、テトラメチルグアニジルプロピルメチルジメトキシシラン、テトラメチルグアニジルプロピルトリス（トリメチルシロキシ）シラン等のグアニジル基を有する加水分解性シラン及びシロキサン等が例示されるが、非金属系有機触媒はこれらに限定されない。また、非金属系有機触媒は１種単独でも２種以上を混合して使用してもよい。 As the non-metallic organic catalyst for the curing catalyst, those known as curing accelerators for condensation-curing organopolysiloxane compositions can be used, and are not particularly limited. For example, phosphazene-containing compounds such as N,N,N',N',N'',N''-hexamethyl-N'''-(trimethylsilylmethyl)-phosphorimidic triamide, n-octylamine, hexylamine , dodecylamine phosphate, amine compounds such as tetramethylguanidine or salts thereof, quaternary ammonium salts such as benzyltriethylammonium acetate, dialkylhydroxylamines such as dimethylhydroxylamine and diethylhydroxylamine, tetramethylguanidylpropyltrimethoxy Examples include hydrolyzable silanes and siloxanes having a guanidyl group such as silane, tetramethylguanidylpropylmethyldimethoxysilane, tetramethylguanidylpropyltris(trimethylsiloxy)silane, etc. Nonmetallic organic catalysts include these. is not limited to The nonmetallic organic catalysts may be used singly or in combination of two or more.
該硬化触媒の金属系触媒としては、縮合硬化型オルガノポリシロキサンの硬化促進剤として公知のものを使用することができ、特に制限されるものではない。例えば、ジブチルスズジアセテート、ジブチルスズジラウレート、ジブチルスズジオクトエート、ジオクチルスズジネオデカノエート、ジ－ｎ－ブチル－ジメトキシスズ等のアルキルスズエステル化合物、テトライソプロポキシチタン、テトラ－ｎ－ブトキシチタン、テトラキス（２－エチルヘキソキシ）チタン、ジプロポキシビス（アセチルアセトナト）チタン、チタニウムイソプロポキシオクチレングリコール等のチタン酸エステル又はチタンキレート化合物、ナフテン酸亜鉛、ステアリン酸亜鉛、亜鉛－２－エチルオクトエート、鉄－２－エチルヘキソエート、コバルト－２－エチルヘキソエート、マンガン－２－エチルヘキソエート、ナフテン酸コバルト、アルミニウムイソプロピレート、アルミニウムセカンダリーブチレートなどのアルコレートアルミニウム化合物、アルミニウムアルキルアセテート・ジイソプロピレート、アルミニウムビスエチルアセトアセテート・モノアセチルアセトネート等のアルミニウムキレート化合物、ネオデカン酸ビスマス（ＩＩＩ）、２－エチルヘキサン酸ビスマス（ＩＩＩ）、クエン酸ビスマス（ＩＩＩ）、オクチル酸ビスマス等の有機金属化合物、酢酸カリウム、酢酸ナトリウム、シュウ酸リチウム等のアルカリ金属の低級脂肪酸塩が例示されるが、金属系触媒はこれらに限定されない。また、金属系触媒は、１種類単独でも２種類以上を混合して使用してもよい。 As the metal-based catalyst for the curing catalyst, those known as curing accelerators for condensation-curable organopolysiloxane can be used, and are not particularly limited. For example, alkyltin ester compounds such as dibutyltin diacetate, dibutyltin dilaurate, dibutyltin dioctate, dioctyltin dineodecanoate, di-n-butyl-dimethoxytin, tetraisopropoxytitanium, tetra-n-butoxytitanium, tetrakis (2-ethylhexoxy)titanium, dipropoxybis(acetylacetonato)titanium, titanium isopropoxyoctylene glycol and other titanate esters or titanium chelate compounds, zinc naphthenate, zinc stearate, zinc-2-ethyloctoate, iron alcoholate aluminum compounds such as 2-ethylhexoate, cobalt-2-ethylhexoate, manganese-2-ethylhexoate, cobalt naphthenate, aluminum isopropylate, aluminum secondary butyrate; Aluminum chelate compounds such as isopropylate, aluminum bisethylacetoacetate/monoacetylacetonate, organic metals such as bismuth (III) neodecanoate, bismuth (III) 2-ethylhexanoate, bismuth (III) citrate, and bismuth octylate Compounds, potassium acetate, sodium acetate, alkali metal lower fatty acid salts such as lithium oxalate are exemplified, but the metal-based catalyst is not limited to these. The metal-based catalysts may be used singly or in combination of two or more.
（Ｄ）成分の硬化触媒の配合量は、上記（Ａ）成分１００質量部に対して０～２０質量部であり、好ましくは０．００１～２０質量部であり、０．０１～１０質量部がより好ましい。（Ｄ）成分の配合量が多すぎると硬化性が速すぎる結果、十分な作業時間が得られず、また経済的に不利となる場合がある。 The amount of the curing catalyst of component (D) is 0 to 20 parts by mass, preferably 0.001 to 20 parts by mass, and 0.01 to 10 parts by mass based on 100 parts by mass of component (A). is more preferred. If the amount of component (D) is too large, the curability will be too fast, resulting in insufficient working time and economic disadvantages.
（Ｅ）成分
（Ｅ）成分は充填剤（無機質充填剤及び／又は有機樹脂充填剤）であり、本発明の組成物に必要に応じて配合できる任意成分であり、この組成物から形成される硬化物に十分な機械的強度を与えるために使用される。この充填剤としては公知のものを使用することができ、例えば、微粉末シリカ、煙霧質シリカ、沈降性シリカ、これらのシリカ表面を有機ケイ素化合物で疎水化処理したシリカ、ガラスビーズ、ガラスバルーン、透明樹脂ビーズ、シリカエアロゲル、珪藻土、酸化鉄、酸化亜鉛、酸化チタン、煙霧状金属酸化物などの金属酸化物、湿式シリカあるいはこれらの表面をシラン処理したもの、石英粉末、カーボンブラック、タルク、ゼオライト及びベントナイト等の補強剤、アスベスト、ガラス繊維、炭素繊維、炭酸カルシウム、重質炭酸カルシウム、炭酸マグネシウム、炭酸亜鉛などの金属炭酸塩、ガラスウール、微粉マイカ、溶融シリカ粉末、ポリスチレン、ポリ塩化ビニル、ポリプロピレンなどの合成樹脂粉末等が使用される。これらの充填剤のうち、シリカ、炭酸カルシウム、ゼオライトなどの無機質充填剤が好ましく、特に表面を疎水化処理した煙霧質シリカ、炭酸カルシウムが好ましい。
(E) component (E) component is a filler (inorganic filler and / or organic resin filler), an optional component that can be blended in the composition of the present invention as necessary, formed from this composition It is used to give sufficient mechanical strength to cured products. Known fillers can be used, for example, finely powdered silica, fumed silica, precipitated silica, silica obtained by hydrophobizing the surface of these silicas with an organosilicon compound, glass beads, glass balloons, Transparent resin beads, silica airgel, diatomaceous earth, iron oxide, zinc oxide, titanium oxide, metal oxides such as fumed metal oxides, wet silica or those whose surfaces are treated with silane, quartz powder, carbon black, talc, zeolite And reinforcing agents such as bentonite, asbestos, glass fiber, carbon fiber, calcium carbonate, ground calcium carbonate, magnesium carbonate, metal carbonate such as zinc carbonate, glass wool, fine mica, fused silica powder, polystyrene, polyvinyl chloride, Synthetic resin powder such as polypropylene is used. Among these fillers, inorganic fillers such as silica, calcium carbonate and zeolite are preferred, and fumed silica and calcium carbonate having a hydrophobic surface are particularly preferred.
（Ｅ）成分の充填剤の配合量は、前記（Ａ）成分１００質量部に対して０～１，０００質量部、特に１～１，０００質量部、とりわけ１～４００質量部とすることが好ましい。未配合の場合より配合した方が、この組成物から得られる硬化物が十分な機械的強度を示す傾向があり、また１，０００質量部よりも多量に使用すると、組成物の粘度が増大して作業性が悪くなるばかりでなく、硬化後のゴム強度が低下してゴム弾性が得難くなる傾向がある。 The amount of the filler of component (E) to be blended is 0 to 1,000 parts by mass, particularly 1 to 1,000 parts by mass, particularly 1 to 400 parts by mass, per 100 parts by mass of component (A). preferable. The cured product obtained from this composition tends to exhibit sufficient mechanical strength when it is blended rather than when it is not blended. Not only does the workability deteriorate when cured, but the strength of the rubber after curing tends to decrease, making it difficult to obtain rubber elasticity.
（Ｆ）成分
（Ｆ）成分は接着促進剤（カーボンファンクショナルシラン（シランカップリング剤））であり、本発明の組成物に必要に応じて配合できる任意成分であり、この組成物から形成される硬化物に十分な接着性を与えるために使用される。具体的には、γ－アミノプロピルトリエトキシシラン、３－２－（アミノエチルアミノ）プロピルトリメトキシシラン等のアミノシラン類、γ－グリシドキシプロピルトリメトキシシラン、β－（３，４－エポキシシクロヘキシル）エチルトリメトキシシラン等のエポキシシラン類、γ－（メタ）アクリロキシプロピルトリメトキシシラン、γ－（メタ）アクリロキシプロピルトリエトキシシラン等の（メタ）アクリルシラン類、γ－メルカプトプロピルトリメトキシシラン等のメルカプトシラン類、γ－イソシアネートプロピルトリメトキシシラン等のイソシアネートシラン類などの、窒素原子、酸素原子、硫黄原子等のヘテロ原子を有する官能性基（但し、グアニジル基を除く）を有する１価炭化水素基を分子中に有する加水分解性オルガノシラン化合物（いわゆるカーボンファンクショナルシラン、又はシランカップリング剤）等を配合することが好ましい。
Component (F) Component (F) is an adhesion promoter (carbon functional silane (silane coupling agent)) and is an optional component that can be blended into the composition of the present invention as necessary. It is used to give sufficient adhesion to cured products. Specifically, aminosilanes such as γ-aminopropyltriethoxysilane and 3-2-(aminoethylamino)propyltrimethoxysilane, γ-glycidoxypropyltrimethoxysilane, β-(3,4-epoxycyclohexyl ) epoxysilanes such as ethyltrimethoxysilane, (meth)acrylsilanes such as γ-(meth)acryloxypropyltrimethoxysilane, γ-(meth)acryloxypropyltriethoxysilane, γ-mercaptopropyltrimethoxysilane mercaptosilanes such as γ-isocyanatopropyltrimethoxysilane, etc., monovalent having a functional group (excluding guanidyl group) having a heteroatom such as a nitrogen atom, an oxygen atom, a sulfur atom, etc. It is preferable to blend a hydrolyzable organosilane compound (so-called carbon functional silane or silane coupling agent) having a hydrocarbon group in the molecule.
（Ｆ）成分の接着促進剤の配合量は、前記（Ａ）成分１００質量部に対して０～３０質量部、特に０．１～２５質量部、とりわけ０．１～２０質量部が好ましい。３０質量部を超えると硬化性が不十分になったり、経済的に不利となる場合がある。 The amount of the adhesion promoter as component (F) is preferably 0 to 30 parts by mass, more preferably 0.1 to 25 parts by mass, particularly preferably 0.1 to 20 parts by mass, per 100 parts by mass of component (A). If the amount exceeds 30 parts by mass, the curability may be insufficient, or it may be economically disadvantageous.
（Ｇ）成分
（Ｇ）成分は可塑剤であり、本発明の組成物に必要に応じて配合できる任意成分であり、この組成物から形成される硬化物の機械特性や難燃性を損なうことなく、施工上取り扱い易い粘度に調整することができる。
Component (G) Component (G) is a plasticizer, which is an optional component that can be blended in the composition of the present invention as necessary, and does not impair the mechanical properties and flame retardancy of the cured product formed from this composition. It is possible to adjust the viscosity to be easy to handle in construction.
本発明の組成物に使用される可塑剤としては、例えば、フタル酸ジメチル（ＤＭＰ）、フタル酸ジエチル（ＤＥＰ）、フタル酸ジ－ｎ－ブチル（ＤＢＰ）、フタル酸ジヘプチル（ＤＨＰ）、フタル酸ジオクチル（ＤＯＰ）、フタル酸ジイソノニル（ＤＩＮＰ）、フタル酸ジイソデシル（ＤＩＤＰ）、フタル酸ジトリデシル（ＤＴＤＰ）、フタル酸ブチルベンジル（ＢＢＰ）、フタル酸ジシクロヘキシル（ＤＣＨＰ）、テトラヒドロフタル酸エステル、アジピン酸ジオクチル（ＤＯＡ）、アジピン酸ジイソノニル（ＤＩＮＡ）、アジピン酸ジイソデシル（ＤＩＤＡ）、アジピン酸ジ－ｎ－アルキル、ジブチルジグリコールアジペート（ＢＸＡ）、アゼライン酸ビス（２－エチルヘキシル）（ＤＯＺ）、セバシン酸ジブチル（ＤＢＳ）、セバシン酸ジオクチル（ＤＯＳ）、マレイン酸ジブチル（ＤＢＭ）、マレイン酸ジ－２－エチルヘキシル（ＤＯＭ）、フマル酸ジブチル（ＤＢＦ）、リン酸トリクレシル（ＴＣＰ）、トリエチルホスフェート（ＴＥＰ）、トリブチルホスフェート（ＴＢ２０Ｐ）、トリス（２－エチルヘキシル）ホスフェート（ＴＯＰ）、トリ（クロロエチル）ホスフェート（ＴＣＥＰ）、トリスジクロロプロピルホスフェート（ＣＰＰ）、トリブトキシエチルホスフェート（ＴＢＸＰ）、トリス（β－クロロプロピル）ホスフェート（ＴＭＣＰＰ）、トリフェニルホスフェート（ＴＰＰ）、オクチルジフェニルホスフェート（ＯＤＰ）、クエン酸アセチルトリエチル、アセチルクエン酸トリブチルなどが挙げられ、その他にはトリメリット酸系可塑剤、ポリエステル系可塑剤、塩素化パラフィン、ステアリン酸系可塑剤など、更にジメチルポリシロキサン等のシリコーンオイル（無官能性オルガノポリシロキサン）、ポリオキシプロピレングリコール系、パラフィン系、ナフテン系、イソパラフィン系等の石油系高沸点溶剤なども用いることができる。これらは１種単独で又は２種以上を組み合わせて用いることができる。その中でも特にシリコーンオイルが好ましい。 Examples of plasticizers used in the composition of the present invention include dimethyl phthalate (DMP), diethyl phthalate (DEP), di-n-butyl phthalate (DBP), diheptyl phthalate (DHP), and phthalic acid. Dioctyl (DOP), diisononyl phthalate (DINP), diisodecyl phthalate (DIDP), ditridecyl phthalate (DTDP), benzyl butyl phthalate (BBP), dicyclohexyl phthalate (DCHP), tetrahydrophthalates, dioctyl adipate ( DOA), diisononyl adipate (DINA), diisodecyl adipate (DIDA), di-n-alkyl adipate, dibutyl diglycol adipate (BXA), bis(2-ethylhexyl) azelate (DOZ), dibutyl sebacate (DBS) ), dioctyl sebacate (DOS), dibutyl maleate (DBM), di-2-ethylhexyl maleate (DOM), dibutyl fumarate (DBF), tricresyl phosphate (TCP), triethyl phosphate (TEP), tributyl phosphate ( TB20P), tris(2-ethylhexyl)phosphate (TOP), tri(chloroethyl)phosphate (TCEP), trisdichloropropylphosphate (CPP), tributoxyethylphosphate (TBXP), tris(β-chloropropyl)phosphate (TMCPP) , triphenyl phosphate (TPP), octyl diphenyl phosphate (ODP), acetyl triethyl citrate, acetyl tributyl citrate, etc. Others include trimellitic acid plasticizers, polyester plasticizers, chlorinated paraffin, stearic acid In addition to silicone oils such as dimethylpolysiloxane (non-functional organopolysiloxane), petroleum-based high boiling point solvents such as polyoxypropylene glycol, paraffin, naphthene, and isoparaffin may also be used. These can be used individually by 1 type or in combination of 2 or more types. Among these, silicone oil is particularly preferred.
なお、上記のシリコーンオイル（無官能性オルガノポリシロキサン）として、下記式（５）で表されるオルガノポリシロキサン（分子鎖両末端トリオルガノシロキシ基封鎖ジオルガノポリシロキサン）を使用することが好ましい。
上記式（５）において、Ｒ4は、それぞれ独立して、非置換もしくは置換の、脂肪族不飽和結合を有しない炭素原子数１～２０の１価炭化水素基であり、具体的には、メチル基、エチル基、ｎ－プロピル基、イソプロピル基、ブチル基、イソブチル基、ｔｅｒｔ－ブチル基、ペンチル基、ネオペンチル基、ヘキシル基、シクロヘキシル基、オクチル基、ノニル基、デシル基、ドデシル基等のアルキル基、フェニル基、トリル基、キシリル基、ナフチル基等のアリール基、ベンジル基、フェニルエチル基、フェニルプロピル基等のアラルキル基や、これらの基の水素原子の一部又は全部を、Ｆ、Ｃｌ、Ｂｒ等のハロゲン原子で置換したもの、例えばクロロメチル基、クロロプロピル基、ブロモエチル基、トリフルオロプロピル基等が挙げられる。 In the above formula (5), each R 4 is independently an unsubstituted or substituted monovalent hydrocarbon group having 1 to 20 carbon atoms and having no aliphatic unsaturated bond, specifically: methyl group, ethyl group, n-propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group, cyclohexyl group, octyl group, nonyl group, decyl group, dodecyl group, etc. aryl groups such as alkyl groups, phenyl groups, tolyl groups, xylyl groups and naphthyl groups; aralkyl groups such as benzyl groups, phenylethyl groups and phenylpropyl groups; Examples thereof include those substituted with halogen atoms such as Cl and Br, such as chloromethyl group, chloropropyl group, bromoethyl group and trifluoropropyl group.
なお、上記式（５）で表されるオルガノポリシロキサンにおいて、ジオルガノシロキサン単位の繰り返し数（重合度）を示すｎの値としては、３～３，０００、好ましくは５～２，０００、より好ましくは１０～１，０００程度の整数であればよい。 In the organopolysiloxane represented by the above formula (5), the value of n, which indicates the number of repeating diorganosiloxane units (degree of polymerization), is 3 to 3,000, preferably 5 to 2,000, and more. An integer of about 10 to 1,000 is preferable.
（Ｇ）成分の配合量は、（Ａ）成分１００質量部に対して０～１，０００質量部であることが好ましく、より好ましくは１～１，０００質量部、更に好ましくは１～２００質量部である。（Ｇ）成分の量が上記範囲内にあると本発明の組成物の機械特性や難燃性を損なうことなく、施工上取り扱い易い粘度に調整することができるため好ましい。 The amount of component (G) is preferably 0 to 1,000 parts by mass, more preferably 1 to 1,000 parts by mass, and still more preferably 1 to 200 parts by mass per 100 parts by mass of component (A). Department. When the amount of component (G) is within the above range, the viscosity can be adjusted to be easy to handle in construction without impairing the mechanical properties and flame retardancy of the composition of the present invention, which is preferable.
［その他の成分］
また、本発明の組成物には、添加剤として、顔料、染料、老化防止剤、酸化防止剤、帯電防止剤、酸化アンチモン、塩化パラフィン等の難燃剤など公知の添加剤を必要に応じて配合することができる。更に、チクソ性向上剤としてのポリエーテル、防かび剤、抗菌剤を配合することもできる。
[Other ingredients]
In addition, known additives such as pigments, dyes, anti-aging agents, antioxidants, antistatic agents, antimony oxide, and flame retardants such as paraffin chloride are added to the composition of the present invention as necessary. can do. Furthermore, a polyether as a thixotropic agent, an antifungal agent, and an antibacterial agent can be blended.
更に、本発明の組成物は、必要に応じて有機溶剤を用いてもよい。有機溶剤としては、ｎ－ヘキサン、ｎ－ヘプタン、イソオクタン、イソドデカンなどの脂肪族炭化水素系化合物、トルエン、キシレンなどの芳香族炭化水素系化合物、ヘキサメチルジシロキサン、オクタメチルトリシロキサン、デカメチルテトラシロキサン、ドデカメチルペンタシロキサン、２－（トリメチルシロキシ）－１，１，１，２，３，３，３－ヘプタメチルトリシロキサンなどの鎖状シロキサン、オクタメチルシクロペンタシロキサン、デカメチルシクロペンタシロキサンなどの環状シロキサンなどが挙げられる。有機溶剤の量は本発明の効果を妨げない範囲で適宜調整すればよい。 Furthermore, the composition of this invention may use an organic solvent as needed. Examples of organic solvents include aliphatic hydrocarbon compounds such as n-hexane, n-heptane, isooctane and isododecane; aromatic hydrocarbon compounds such as toluene and xylene; hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane; siloxane, chain siloxane such as dodecamethylpentasiloxane, 2-(trimethylsiloxy)-1,1,1,2,3,3,3-heptamethyltrisiloxane, octamethylcyclopentasiloxane, decamethylcyclopentasiloxane, etc. and the like. The amount of the organic solvent may be appropriately adjusted within a range that does not impair the effects of the present invention.
本発明の組成物は、１成分型の組成物、又は２成分型以上の多成分型の組成物等として使用することができる。 The composition of the present invention can be used as a one-component composition, a two-component or more multi-component composition, or the like.
本発明の組成物は、上記各成分、更にはこれに上記各種添加剤の所定量を、乾燥雰囲気中において均一に混合することにより得ることができる。また、本発明の組成物は、室温で放置することにより硬化するが、その成形方法、硬化条件などは、組成物の種類に応じた公知の方法、条件を採用することができる。 The composition of the present invention can be obtained by uniformly mixing each of the components described above and predetermined amounts of the various additives described above in a dry atmosphere. The composition of the present invention is cured by standing at room temperature, and known methods and conditions can be employed for the molding method and curing conditions according to the type of composition.
本発明の組成物、特に１成分型の組成物は、水（湿気）の非存在下、即ち湿気を遮断した密閉容器中で保存し、使用時に空気中の水に曝すことによって室温（２３℃±１５℃）で容易に硬化する。２成分型以上の多成分型の組成物は、水の非存在下、即ち湿気を遮断した密閉容器中で保存し、使用に際して個別に保存された複数の組成物同士を空気中の水の存在下で混合することにより室温（２３℃±１５℃）で容易に硬化する。 The compositions of the present invention, particularly the one-component compositions, can be stored in the absence of water (humidity), i.e., in closed containers protected from moisture, and when used, can be stored at room temperature (23°C) by exposure to water in the air. ±15°C). Two or more multi-component compositions are stored in the absence of water, i.e., in a moisture-proof closed container. Cures readily at room temperature (23°C ± 15°C) by mixing below.
また、本発明の組成物の硬化物（シリコーンゴム硬化物）は良好な柔軟性を示し、ゴム弾性を有することから、コーティング剤、接着剤、シーリング剤（例えば、建築用シーラント等）として有用である。本発明の組成物をコーティング剤、接着剤、シーリング剤として使用する方法は、従来公知の使用方法に従えばよく、特に制限されるものでない。 In addition, since the cured product (cured product of silicone rubber) of the composition of the present invention exhibits good flexibility and has rubber elasticity, it is useful as a coating agent, an adhesive, a sealing agent (for example, a building sealant, etc.). be. The method of using the composition of the present invention as a coating agent, an adhesive, or a sealant is not particularly limited as long as it follows conventionally known methods of use.
本発明の組成物の硬化物からなる被覆層を有する物品としては、例えば、ガラス類、各種樹脂類、各種金属類等で構成された物品などが例示できるが、基材の材質及び形状については特に限定されない。 Examples of articles having a coating layer comprising a cured product of the composition of the present invention include articles made of glass, various resins, various metals, and the like. It is not particularly limited.
本発明の組成物の硬化物で接着及び／又はシールされた物品としては、例えば、ガラス類、各種金属類等で構成された物品などが例示できるが、基材の材質及び形状については特に限定されない。 Examples of articles adhered and/or sealed with the cured product of the composition of the present invention include articles made of glass, various metals, etc., but the material and shape of the substrate are particularly limited. not.
以下、実施例及び比較例を示し、本発明を具体的に説明するが、本発明は下記の実施例に制限されるものではない。なお、下記の具体例において、「部」は「質量部」を意味し、また粘度は２３℃での回転粘度計による測定値を示したものである。 EXAMPLES The present invention will be specifically described below by showing examples and comparative examples, but the present invention is not limited to the following examples. In the following specific examples, "parts" means "parts by mass", and the viscosity is measured at 23°C with a rotational viscometer.
［実施例１－１］
粘度５，０００ｍＰａ・ｓの分子鎖両末端がケイ素原子に結合した水酸基（シラノール基）で封鎖されたジメチルポリシロキサン１００質量部に、ジメトキシ（メチル）（ジエチルアミノメチル）シラン１．５質量部、（ジエチルアミノメチル）トリメトキシシラン０．８質量部を加え、湿気遮断下で均一に混合し、組成物１を得た。
[Example 1-1]
To 100 parts by mass of dimethylpolysiloxane having a viscosity of 5,000 mPa s and both molecular chain ends blocked with hydroxyl groups (silanol groups) bonded to silicon atoms, 1.5 parts by mass of dimethoxy(methyl)(diethylaminomethyl)silane, ( Diethylaminomethyl)trimethoxysilane (0.8 parts by mass) was added and uniformly mixed in the absence of moisture to obtain composition 1.
［実施例１－２］
ジメトキシ（メチル）（ジエチルアミノメチル）シラン１．５質量部の代わりにジメトキシ（メチル）（ジプロピルアミノメチル）シラン１．８質量部を用い、（ジエチルアミノメチル）トリメトキシシラン０．８質量部の代わりに（ジプロピルアミノメチル）トリメトキシシラン０．９質量部を用いた以外は実施例１－１と同様にして組成物２を得た。
[Example 1-2]
Using 1.8 parts by weight of dimethoxy(methyl)(dipropylaminomethyl)silane instead of 1.5 parts by weight of dimethoxy(methyl)(diethylaminomethyl)silane and replacing 0.8 parts by weight of (diethylaminomethyl)trimethoxysilane A composition 2 was obtained in the same manner as in Example 1-1, except that 0.9 parts by mass of (dipropylaminomethyl)trimethoxysilane was used.
［比較例１－１］
（ジエチルアミノメチル）トリメトキシシラン０．８質量部の代わりにビニルトリメトキシシラン０．６質量部を用いた以外は実施例１－１と同様にして組成物３を得た。
[Comparative Example 1-1]
Composition 3 was obtained in the same manner as in Example 1-1, except that 0.6 parts by mass of vinyltrimethoxysilane was used instead of 0.8 parts by mass of (diethylaminomethyl)trimethoxysilane.
［比較例１－２］
（ジプロピルアミノメチル）トリメトキシシラン０．９質量部の代わりにビニルトリメトキシシラン０．６質量部を用いた以外は実施例１－２と同様にして組成物４を得た。
[Comparative Example 1-2]
Composition 4 was obtained in the same manner as in Example 1-2, except that 0.6 parts by mass of vinyltrimethoxysilane was used instead of 0.9 parts by mass of (dipropylaminomethyl)trimethoxysilane.
［比較例２－１］
ジメトキシ（メチル）（ジエチルアミノメチル）シラン１．５質量部の代わりにジメチルジメトキシシラン１．２質量部を用いた以外は実施例１－１と同様にして組成物５を得た。
[Comparative Example 2-1]
Composition 5 was obtained in the same manner as in Example 1-1, except that 1.2 parts by mass of dimethyldimethoxysilane was used instead of 1.5 parts by mass of dimethoxy(methyl)(diethylaminomethyl)silane.
［比較例３－１］
（ジエチルアミノメチル）トリメトキシシラン０．８質量部を添加しないこと以外は実施例１－１と同様にして組成物６を得た。
[Comparative Example 3-1]
A composition 6 was obtained in the same manner as in Example 1-1, except that 0.8 parts by mass of (diethylaminomethyl)trimethoxysilane was not added.
［比較例４－１］
ジメトキシ（メチル）（ジエチルアミノメチル）シラン１．５質量部を添加しないこと以外は実施例１－１と同様にして組成物７を得た。
[Comparative Example 4-1]
Composition 7 was obtained in the same manner as in Example 1-1, except that 1.5 parts by mass of dimethoxy(methyl)(diethylaminomethyl)silane was not added.
［比較例５－１］
ジメトキシ（メチル）（ジエチルアミノメチル）シラン１．５質量部の代わりに、ジメチルジメトキシシラン１．２質量部を用い、（ジエチルアミノメチル）トリメトキシシラン０．８質量部の代わりに、ビニルトリメトキシシラン０．６質量部を配合した以外は実施例１－１と同様にして組成物８を得た。
[Comparative Example 5-1]
1.2 parts by weight of dimethyldimethoxysilane was used instead of 1.5 parts by weight of dimethoxy(methyl)(diethylaminomethyl)silane, and 0 parts by weight of (diethylaminomethyl)trimethoxysilane was replaced by 0 parts by weight of vinyltrimethoxysilane. Composition 8 was obtained in the same manner as in Example 1-1, except that .6 parts by mass was added.
〔物性評価試験〕
実施例１－１、１－２及び比較例１－１～５－１で調製した調製直後の各組成物を厚さ２ｍｍのシート状に押し出し、２３℃、５０％ＲＨの空気に曝し、次いで、該シートを同じ雰囲気下に７日間放置して得た硬化物の物性（初期物性）を、ＪＩＳ Ｋ－６２４９に準拠して測定した。なお、該硬化物の硬さは、ＪＩＳ Ｋ－６２４９のデュロメーターＡ硬度計又はアスカーＣ硬度計を用いて測定した。それらの結果を表１、表２に示す。
[Physical property evaluation test]
Each composition immediately after preparation prepared in Examples 1-1, 1-2 and Comparative Examples 1-1 to 5-1 was extruded into a sheet having a thickness of 2 mm, exposed to air at 23 ° C. and 50% RH, and then The physical properties (initial physical properties) of a cured product obtained by leaving the sheet under the same atmosphere for 7 days were measured according to JIS K-6249. The hardness of the cured product was measured using a JIS K-6249 Durometer A hardness tester or Asker C hardness tester. The results are shown in Tables 1 and 2.
表１の結果より、実施例１－１～１－２は対応する比較例１－１～１－２と比べて、反応性が良好であり、速やかにゴム化し、より適度な伸びを発現することが明らかとなった。
一方、表２の結果より、比較例２－１と４－１では反応の進行を制御することができず、各成分の混合時に（混合途中で）ゴム化してしまい、均一な硬化被膜を得ることができなかった。また、比較例３－１と５－１では調製した組成物を硬化することができなかった。
From the results in Table 1, Examples 1-1 and 1-2 have better reactivity than the corresponding Comparative Examples 1-1 and 1-2, quickly rubberize, and exhibit more moderate elongation. It became clear.
On the other hand, from the results in Table 2, it was not possible to control the progress of the reaction in Comparative Examples 2-1 and 4-1, and the components were rubberized during mixing (during mixing), resulting in a uniform cured film. I couldn't. Also, the compositions prepared in Comparative Examples 3-1 and 5-1 could not be cured.
Claims (7)
（Ｂ）下記の式（１）で表されるオルガノシラン化合物：０．００１～３０質量部、
（Ｃ）下記の式（２）で表されるオルガノシラン化合物：０．００１～３０質量部、
を含有するものである室温硬化性樹脂組成物。 (A) a silicone polymer having both molecular chain ends blocked with silanol groups or hydrolyzable silyl groups: 100 parts by mass;
(B) an organosilane compound represented by the following formula (1): 0.001 to 30 parts by mass;
(C) an organosilane compound represented by the following formula (2): 0.001 to 30 parts by mass,
A room temperature curable resin composition containing
（Ｄ）硬化触媒：０．００１～２０質量部
（Ｅ）充填剤：１～１，０００質量部
（Ｆ）接着促進剤：０．１～３０質量部
（Ｇ）可塑剤：１～１，０００質量部
から選ばれる１種又は２種以上の成分を含有する請求項１に記載の室温硬化性樹脂組成物。 Furthermore, with respect to 100 parts by mass of component (A),
(D) Curing catalyst: 0.001 to 20 parts by mass (E) Filler: 1 to 1,000 parts by mass (F) Adhesion promoter: 0.1 to 30 parts by mass (G) Plasticizer: 1 to 1, 2. The room temperature curable resin composition according to claim 1, containing one or more components selected from 000 parts by mass.
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