JP2006525396A - シリルエステル、これらを結合剤系および塗料組成物で使用する方法およびそれらを製造する方法 - Google Patents
シリルエステル、これらを結合剤系および塗料組成物で使用する方法およびそれらを製造する方法 Download PDFInfo
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- JP2006525396A JP2006525396A JP2006505410A JP2006505410A JP2006525396A JP 2006525396 A JP2006525396 A JP 2006525396A JP 2006505410 A JP2006505410 A JP 2006505410A JP 2006505410 A JP2006505410 A JP 2006505410A JP 2006525396 A JP2006525396 A JP 2006525396A
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- Prior art keywords
- acetoxy
- acid
- binder
- silane
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- 239000011230 binding agent Substances 0.000 title claims abstract description 79
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims description 41
- 239000008199 coating composition Substances 0.000 title claims description 30
- -1 organosilyl ester Chemical class 0.000 claims abstract description 128
- 239000003973 paint Substances 0.000 claims abstract description 57
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000000203 mixture Substances 0.000 claims abstract description 34
- 230000003373 anti-fouling effect Effects 0.000 claims abstract description 24
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 20
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 19
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 18
- 150000002148 esters Chemical class 0.000 claims abstract description 11
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims abstract description 7
- 239000003380 propellant Substances 0.000 claims abstract description 6
- 230000003628 erosive effect Effects 0.000 claims abstract description 5
- 238000009472 formulation Methods 0.000 claims abstract description 5
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 68
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims description 59
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims description 59
- 239000002253 acid Substances 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 23
- 238000009835 boiling Methods 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 125000004104 aryloxy group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 12
- 229920002554 vinyl polymer Polymers 0.000 claims description 12
- 150000007513 acids Chemical class 0.000 claims description 11
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 11
- 238000000576 coating method Methods 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 229920001577 copolymer Polymers 0.000 claims description 10
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 9
- 239000011248 coating agent Substances 0.000 claims description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004423 acyloxy group Chemical group 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- KXJLGCBCRCSXQF-UHFFFAOYSA-N [diacetyloxy(ethyl)silyl] acetate Chemical compound CC(=O)O[Si](CC)(OC(C)=O)OC(C)=O KXJLGCBCRCSXQF-UHFFFAOYSA-N 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000001302 tertiary amino group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 238000006884 silylation reaction Methods 0.000 claims description 5
- QHUNJMXHQHHWQP-UHFFFAOYSA-N trimethylsilyl acetate Chemical compound CC(=O)O[Si](C)(C)C QHUNJMXHQHHWQP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 claims description 4
- NOZAQBYNLKNDRT-UHFFFAOYSA-N [diacetyloxy(ethenyl)silyl] acetate Chemical compound CC(=O)O[Si](OC(C)=O)(OC(C)=O)C=C NOZAQBYNLKNDRT-UHFFFAOYSA-N 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 235000019260 propionic acid Nutrition 0.000 claims description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- RQVFGTYFBUVGOP-UHFFFAOYSA-N [acetyloxy(dimethyl)silyl] acetate Chemical compound CC(=O)O[Si](C)(C)OC(C)=O RQVFGTYFBUVGOP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 239000000539 dimer Substances 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 3
- AAURKQPZJJMXER-UHFFFAOYSA-N triethylsilyl acetate Chemical compound CC[Si](CC)(CC)OC(C)=O AAURKQPZJJMXER-UHFFFAOYSA-N 0.000 claims description 3
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims description 2
- LAXPIARTVCARCF-UHFFFAOYSA-N 2-[tert-butyl(dimethyl)silyl]acetic acid Chemical compound CC(C)(C)[Si](C)(C)CC(O)=O LAXPIARTVCARCF-UHFFFAOYSA-N 0.000 claims description 2
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims description 2
- WEFMXJCNUJJPSM-UHFFFAOYSA-N [[[[[bis(2-methylpropyl)-[tris(2-methylpropyl)silyloxy]silyl]oxy-bis(2-methylpropyl)silyl]oxy-bis(2-methylpropyl)silyl]oxy-bis(2-methylpropyl)silyl]oxy-bis(2-methylpropyl)silyl] acetate Chemical compound CC(C)C[Si](CC(C)C)(CC(C)C)O[Si](CC(C)C)(CC(C)C)O[Si](CC(C)C)(CC(C)C)O[Si](CC(C)C)(CC(C)C)O[Si](CC(C)C)(CC(C)C)O[Si](CC(C)C)(CC(C)C)OC(C)=O WEFMXJCNUJJPSM-UHFFFAOYSA-N 0.000 claims description 2
- ZITFVSRYQMVPCJ-UHFFFAOYSA-N [[[[[di(propan-2-yl)-tri(propan-2-yl)silyloxysilyl]oxy-di(propan-2-yl)silyl]oxy-di(propan-2-yl)silyl]oxy-di(propan-2-yl)silyl]oxy-di(propan-2-yl)silyl] acetate Chemical compound CC(=O)O[Si](C(C)C)(C(C)C)O[Si](C(C)C)(C(C)C)O[Si](C(C)C)(C(C)C)O[Si](C(C)C)(C(C)C)O[Si](C(C)C)(C(C)C)O[Si](C(C)C)(C(C)C)C(C)C ZITFVSRYQMVPCJ-UHFFFAOYSA-N 0.000 claims description 2
- PMNBVVNXSQITNU-UHFFFAOYSA-N [[[[[dihexyl(trihexylsilyloxy)silyl]oxy-dihexylsilyl]oxy-dihexylsilyl]oxy-dihexylsilyl]oxy-dihexylsilyl] acetate Chemical compound CCCCCC[Si](CCCCCC)(CCCCCC)O[Si](CCCCCC)(CCCCCC)O[Si](CCCCCC)(CCCCCC)O[Si](CCCCCC)(CCCCCC)O[Si](CCCCCC)(CCCCCC)O[Si](CCCCCC)(CCCCCC)OC(C)=O PMNBVVNXSQITNU-UHFFFAOYSA-N 0.000 claims description 2
- BCWDWLWFKNOVMD-UHFFFAOYSA-N [[[[[dioctyl(trioctylsilyloxy)silyl]oxy-dioctylsilyl]oxy-dioctylsilyl]oxy-dioctylsilyl]oxy-dioctylsilyl] acetate Chemical compound CCCCCCCC[Si](CCCCCCCC)(CCCCCCCC)O[Si](CCCCCCCC)(CCCCCCCC)O[Si](CCCCCCCC)(CCCCCCCC)O[Si](CCCCCCCC)(CCCCCCCC)O[Si](CCCCCCCC)(CCCCCCCC)O[Si](CCCCCCCC)(CCCCCCCC)OC(C)=O BCWDWLWFKNOVMD-UHFFFAOYSA-N 0.000 claims description 2
- XBWPCJSVWRQADS-UHFFFAOYSA-N [[[[[diphenyl(triphenylsilyloxy)silyl]oxy-diphenylsilyl]oxy-diphenylsilyl]oxy-diphenylsilyl]oxy-diphenylsilyl] acetate Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(OC(=O)C)O[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)O[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)O[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)O[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)O[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XBWPCJSVWRQADS-UHFFFAOYSA-N 0.000 claims description 2
- GHYBZBLXCPMDCS-UHFFFAOYSA-N [[[[[dipropyl(tripropylsilyloxy)silyl]oxy-dipropylsilyl]oxy-dipropylsilyl]oxy-dipropylsilyl]oxy-dipropylsilyl] acetate Chemical compound CCC[Si](CCC)(CCC)O[Si](CCC)(CCC)O[Si](CCC)(CCC)O[Si](CCC)(CCC)O[Si](CCC)(CCC)O[Si](CCC)(CCC)OC(C)=O GHYBZBLXCPMDCS-UHFFFAOYSA-N 0.000 claims description 2
- PJPOQCWBBWGIPV-UHFFFAOYSA-N [[[[bis(2-methylpropyl)-[tris(2-methylpropyl)silyloxy]silyl]oxy-bis(2-methylpropyl)silyl]oxy-bis(2-methylpropyl)silyl]oxy-bis(2-methylpropyl)silyl] acetate Chemical compound CC(C)C[Si](CC(C)C)(CC(C)C)O[Si](CC(C)C)(CC(C)C)O[Si](CC(C)C)(CC(C)C)O[Si](CC(C)C)(CC(C)C)O[Si](CC(C)C)(CC(C)C)OC(C)=O PJPOQCWBBWGIPV-UHFFFAOYSA-N 0.000 claims description 2
- LBTVOCZAMLWNMT-UHFFFAOYSA-N [[[[di(propan-2-yl)-tri(propan-2-yl)silyloxysilyl]oxy-di(propan-2-yl)silyl]oxy-di(propan-2-yl)silyl]oxy-di(propan-2-yl)silyl] acetate Chemical compound CC(=O)O[Si](C(C)C)(C(C)C)O[Si](C(C)C)(C(C)C)O[Si](C(C)C)(C(C)C)O[Si](C(C)C)(C(C)C)O[Si](C(C)C)(C(C)C)C(C)C LBTVOCZAMLWNMT-UHFFFAOYSA-N 0.000 claims description 2
- CUWYXPUZOYOXPN-UHFFFAOYSA-N [[[[didodecyl(tridodecylsilyloxy)silyl]oxy-didodecylsilyl]oxy-didodecylsilyl]oxy-didodecylsilyl] acetate Chemical compound CCCCCCCCCCCC[Si](CCCCCCCCCCCC)(CCCCCCCCCCCC)O[Si](CCCCCCCCCCCC)(CCCCCCCCCCCC)O[Si](CCCCCCCCCCCC)(CCCCCCCCCCCC)O[Si](CCCCCCCCCCCC)(CCCCCCCCCCCC)O[Si](CCCCCCCCCCCC)(CCCCCCCCCCCC)OC(C)=O CUWYXPUZOYOXPN-UHFFFAOYSA-N 0.000 claims description 2
- KQZSQFYGPBUVSD-UHFFFAOYSA-N [[[[dihexyl(trihexylsilyloxy)silyl]oxy-dihexylsilyl]oxy-dihexylsilyl]oxy-dihexylsilyl] acetate Chemical compound CCCCCC[Si](CCCCCC)(CCCCCC)O[Si](CCCCCC)(CCCCCC)O[Si](CCCCCC)(CCCCCC)O[Si](CCCCCC)(CCCCCC)O[Si](CCCCCC)(CCCCCC)OC(C)=O KQZSQFYGPBUVSD-UHFFFAOYSA-N 0.000 claims description 2
- MHCUGNHJUHLJDE-UHFFFAOYSA-N [[[[dioctyl(trioctylsilyloxy)silyl]oxy-dioctylsilyl]oxy-dioctylsilyl]oxy-dioctylsilyl] acetate Chemical compound CCCCCCCC[Si](CCCCCCCC)(CCCCCCCC)O[Si](CCCCCCCC)(CCCCCCCC)O[Si](CCCCCCCC)(CCCCCCCC)O[Si](CCCCCCCC)(CCCCCCCC)O[Si](CCCCCCCC)(CCCCCCCC)OC(C)=O MHCUGNHJUHLJDE-UHFFFAOYSA-N 0.000 claims description 2
- QYQYBEFYUPQOMH-UHFFFAOYSA-N [[[[dipentyl(tripentylsilyloxy)silyl]oxy-dipentylsilyl]oxy-dipentylsilyl]oxy-dipentylsilyl] acetate Chemical compound CCCCC[Si](CCCCC)(CCCCC)O[Si](CCCCC)(CCCCC)O[Si](CCCCC)(CCCCC)O[Si](CCCCC)(CCCCC)O[Si](CCCCC)(CCCCC)OC(C)=O QYQYBEFYUPQOMH-UHFFFAOYSA-N 0.000 claims description 2
- NPKZCGKBUPXIBN-UHFFFAOYSA-N [[[[diphenyl(triphenylsilyloxy)silyl]oxy-diphenylsilyl]oxy-diphenylsilyl]oxy-diphenylsilyl] acetate Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(OC(=O)C)O[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)O[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)O[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)O[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 NPKZCGKBUPXIBN-UHFFFAOYSA-N 0.000 claims description 2
- FYTRWIDUFKPVDE-UHFFFAOYSA-N [[[[dipropyl(tripropylsilyloxy)silyl]oxy-dipropylsilyl]oxy-dipropylsilyl]oxy-dipropylsilyl] acetate Chemical compound CCC[Si](CCC)(CCC)O[Si](CCC)(CCC)O[Si](CCC)(CCC)O[Si](CCC)(CCC)O[Si](CCC)(CCC)OC(C)=O FYTRWIDUFKPVDE-UHFFFAOYSA-N 0.000 claims description 2
- GOWLVOLFTCUOMO-UHFFFAOYSA-N [[[bis(2-methylpropyl)-[tris(2-methylpropyl)silyloxy]silyl]oxy-bis(2-methylpropyl)silyl]oxy-bis(2-methylpropyl)silyl] acetate Chemical compound CC(C)C[Si](CC(C)C)(CC(C)C)O[Si](CC(C)C)(CC(C)C)O[Si](CC(C)C)(CC(C)C)O[Si](CC(C)C)(CC(C)C)OC(C)=O GOWLVOLFTCUOMO-UHFFFAOYSA-N 0.000 claims description 2
- CZHSFMWYPFXKHV-UHFFFAOYSA-N [[[di(propan-2-yl)-tri(propan-2-yl)silyloxysilyl]oxy-di(propan-2-yl)silyl]oxy-di(propan-2-yl)silyl] acetate Chemical compound CC(=O)O[Si](C(C)C)(C(C)C)O[Si](C(C)C)(C(C)C)O[Si](C(C)C)(C(C)C)O[Si](C(C)C)(C(C)C)C(C)C CZHSFMWYPFXKHV-UHFFFAOYSA-N 0.000 claims description 2
- RVKOVVONPIXMOB-UHFFFAOYSA-N [[[didodecyl(tridodecylsilyloxy)silyl]oxy-didodecylsilyl]oxy-didodecylsilyl] acetate Chemical compound CCCCCCCCCCCC[Si](CCCCCCCCCCCC)(CCCCCCCCCCCC)O[Si](CCCCCCCCCCCC)(CCCCCCCCCCCC)O[Si](CCCCCCCCCCCC)(CCCCCCCCCCCC)O[Si](CCCCCCCCCCCC)(CCCCCCCCCCCC)OC(C)=O RVKOVVONPIXMOB-UHFFFAOYSA-N 0.000 claims description 2
- JEGBJAPYBRWWRL-UHFFFAOYSA-N [[[dihexyl(trihexylsilyloxy)silyl]oxy-dihexylsilyl]oxy-dihexylsilyl] acetate Chemical compound CCCCCC[Si](CCCCCC)(CCCCCC)O[Si](CCCCCC)(CCCCCC)O[Si](CCCCCC)(CCCCCC)O[Si](CCCCCC)(CCCCCC)OC(C)=O JEGBJAPYBRWWRL-UHFFFAOYSA-N 0.000 claims description 2
- YWYIPYFYBBPDPF-UHFFFAOYSA-N [[[dimethyl(trimethylsilyloxy)silyl]oxy-dimethylsilyl]oxy-dimethylsilyl] acetate Chemical compound CC(=O)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C YWYIPYFYBBPDPF-UHFFFAOYSA-N 0.000 claims description 2
- AFMALIDOUSVBOY-UHFFFAOYSA-N [[[dioctyl(trioctylsilyloxy)silyl]oxy-dioctylsilyl]oxy-dioctylsilyl] acetate Chemical compound CCCCCCCC[Si](CCCCCCCC)(CCCCCCCC)O[Si](CCCCCCCC)(CCCCCCCC)O[Si](CCCCCCCC)(CCCCCCCC)O[Si](CCCCCCCC)(CCCCCCCC)OC(C)=O AFMALIDOUSVBOY-UHFFFAOYSA-N 0.000 claims description 2
- ORMGDOQLQIVLMA-UHFFFAOYSA-N [[[diphenyl(triphenylsilyloxy)silyl]oxy-diphenylsilyl]oxy-diphenylsilyl] acetate Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(OC(=O)C)O[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)O[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)O[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ORMGDOQLQIVLMA-UHFFFAOYSA-N 0.000 claims description 2
- KLUGINNNVJZEON-UHFFFAOYSA-N [[[dipropyl(tripropylsilyloxy)silyl]oxy-dipropylsilyl]oxy-dipropylsilyl] acetate Chemical compound CCC[Si](CCC)(CCC)O[Si](CCC)(CCC)O[Si](CCC)(CCC)O[Si](CCC)(CCC)OC(C)=O KLUGINNNVJZEON-UHFFFAOYSA-N 0.000 claims description 2
- FSSYAMFHMWQZGL-UHFFFAOYSA-N [[dimethyl(trimethylsilyloxy)silyl]oxy-dimethylsilyl] acetate Chemical compound CC(=O)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C FSSYAMFHMWQZGL-UHFFFAOYSA-N 0.000 claims description 2
- GEVLQTJAHGKELA-UHFFFAOYSA-N [acetyloxy(dibutyl)silyl] acetate Chemical compound CCCC[Si](OC(C)=O)(OC(C)=O)CCCC GEVLQTJAHGKELA-UHFFFAOYSA-N 0.000 claims description 2
- JQNJIBYLKBOSCM-UHFFFAOYSA-N [acetyloxy(diethyl)silyl] acetate Chemical compound CC(=O)O[Si](CC)(CC)OC(C)=O JQNJIBYLKBOSCM-UHFFFAOYSA-N 0.000 claims description 2
- CNOSCOOHMORKEM-UHFFFAOYSA-N [acetyloxy(dipropyl)silyl] acetate Chemical compound CCC[Si](CCC)(OC(C)=O)OC(C)=O CNOSCOOHMORKEM-UHFFFAOYSA-N 0.000 claims description 2
- LSDYFQXXPCPBQV-UHFFFAOYSA-N [diacetyloxy(butyl)silyl] acetate Chemical compound CCCC[Si](OC(C)=O)(OC(C)=O)OC(C)=O LSDYFQXXPCPBQV-UHFFFAOYSA-N 0.000 claims description 2
- DKGZKEKMWBGTIB-UHFFFAOYSA-N [diacetyloxy(propyl)silyl] acetate Chemical compound CCC[Si](OC(C)=O)(OC(C)=O)OC(C)=O DKGZKEKMWBGTIB-UHFFFAOYSA-N 0.000 claims description 2
- AIWOUSUCBNRWOQ-UHFFFAOYSA-N [dibutyl-[dibutyl-[dibutyl(tributylsilyloxy)silyl]oxysilyl]oxysilyl] acetate Chemical compound CCCC[Si](CCCC)(CCCC)O[Si](CCCC)(CCCC)O[Si](CCCC)(CCCC)O[Si](CCCC)(CCCC)OC(C)=O AIWOUSUCBNRWOQ-UHFFFAOYSA-N 0.000 claims description 2
- YMHPWLXPULJICW-UHFFFAOYSA-N [dibutyl-[dibutyl-[dibutyl-[dibutyl(tributylsilyloxy)silyl]oxysilyl]oxysilyl]oxysilyl] acetate Chemical compound CCCC[Si](CCCC)(CCCC)O[Si](CCCC)(CCCC)O[Si](CCCC)(CCCC)O[Si](CCCC)(CCCC)O[Si](CCCC)(CCCC)OC(C)=O YMHPWLXPULJICW-UHFFFAOYSA-N 0.000 claims description 2
- ZBJZQUBCWFODND-UHFFFAOYSA-N [dibutyl-[dibutyl-[dibutyl-[dibutyl-[dibutyl(tributylsilyloxy)silyl]oxysilyl]oxysilyl]oxysilyl]oxysilyl] acetate Chemical compound CCCC[Si](CCCC)(CCCC)O[Si](CCCC)(CCCC)O[Si](CCCC)(CCCC)O[Si](CCCC)(CCCC)O[Si](CCCC)(CCCC)O[Si](CCCC)(CCCC)OC(C)=O ZBJZQUBCWFODND-UHFFFAOYSA-N 0.000 claims description 2
- QSPUKCHZOMPBLM-UHFFFAOYSA-N [dimethyl(trimethylsilyloxy)silyl] acetate Chemical compound CC(=O)O[Si](C)(C)O[Si](C)(C)C QSPUKCHZOMPBLM-UHFFFAOYSA-N 0.000 claims description 2
- FMHFIWJSIWEUCF-UHFFFAOYSA-N [ditert-butyl-[ditert-butyl-[ditert-butyl(tritert-butylsilyloxy)silyl]oxysilyl]oxysilyl] acetate Chemical compound CC(=O)O[Si](C(C)(C)C)(C(C)(C)C)O[Si](C(C)(C)C)(C(C)(C)C)O[Si](C(C)(C)C)(C(C)(C)C)O[Si](C(C)(C)C)(C(C)(C)C)C(C)(C)C FMHFIWJSIWEUCF-UHFFFAOYSA-N 0.000 claims description 2
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- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- IZUPBVBPLAPZRR-UHFFFAOYSA-M pentachlorophenolate Chemical compound [O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-M 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- ONVABDHFQKWOSV-NDLGOLERSA-N phyllocladene Chemical compound C1C[C@@H](C2)C(=C)C[C@]32CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]31 ONVABDHFQKWOSV-NDLGOLERSA-N 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- YZVSLDRKXBZOMY-KNOXWWKRSA-N sandaracopimaric acid Natural products CC(=C)[C@]1(C)CCC[C@]2(C)[C@H]3CC[C@](C)(C=C)C=C3CC[C@@H]12 YZVSLDRKXBZOMY-KNOXWWKRSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- GRJISGHXMUQUMC-UHFFFAOYSA-N silyl prop-2-enoate Chemical class [SiH3]OC(=O)C=C GRJISGHXMUQUMC-UHFFFAOYSA-N 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
- JZLXVLPJZAGGNL-UHFFFAOYSA-N trifluorosilyl acetate Chemical compound CC(=O)O[Si](F)(F)F JZLXVLPJZAGGNL-UHFFFAOYSA-N 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- HAIZQIKYAKUOBN-UHFFFAOYSA-N trimethylsilyl 2,2,2-trichloroacetate Chemical compound C[Si](C)(C)OC(=O)C(Cl)(Cl)Cl HAIZQIKYAKUOBN-UHFFFAOYSA-N 0.000 description 1
- VIYXXANHGYSBLY-UHFFFAOYSA-N trimethylsilyl 2,2,2-trifluoroacetate Chemical compound C[Si](C)(C)OC(=O)C(F)(F)F VIYXXANHGYSBLY-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002348 vinylic group Chemical group 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- RKQOSDAEEGPRER-UHFFFAOYSA-L zinc diethyldithiocarbamate Chemical compound [Zn+2].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S RKQOSDAEEGPRER-UHFFFAOYSA-L 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- NRINZBKAERVHFW-UHFFFAOYSA-L zinc;dicarbamate Chemical compound [Zn+2].NC([O-])=O.NC([O-])=O NRINZBKAERVHFW-UHFFFAOYSA-L 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
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- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
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Abstract
Description
Zは、
各R4およびR5は、ヒドロキシルであってもよいか、或は独立して、アルキル、アリール、アルコキシル、アリールオキシル、−L’−SiR1R2R3、−L’−(SiR4R5L’)n−SiR1R2R3、−L’−SiR1R2−、−L’−(SiR4R5L’)n−SiR1R2−、アルケニル、アルキニル、アラルキルまたはアラルキルオキシル基から選択されてもよく、ここで、これらは場合によりアルキル、アルコキシル、アラルキル、アラルキルオキシル、ヒドロキシル、アリール、アリールオキシル、ハロゲン、アミノ(好適には第三級アミノ)またはアミノアルキル基を包含する群から独立して選択される1個以上の置換基で置換されていてもよく、或はR4またはR5は、独立して、−O−Z−R8基であってもよく、ここで、R8は以下に示すR7と同様に定義され、
各R1、R2およびR3は、独立して、水素、ヒドロキシル、アルキル、アルケニル、アルキニル、アルコキシル、アリール、アリールオキシル、アラルキルまたはアラルキルオキシル基を表してもよく、ここで、これらは場合によりアルキル、アルコキシル、アラルキル、アラルキルオキシル、アリール、アリールオキシル、ハロゲン、ヒドロキシル、アミノ(好適には第三級アミノ)またはアミノアルキル基を包含する群から独立して選択される1個以上の置換基で置換されていてもよく、或はR1、R2またはR3は、独立して、−O−Z−R8基であってもよく、
L’は、O、SまたはNR6(ここで、R6は以下に示すR9と同様に定義される)を表し、
各nは、独立して、0から1000の−Si(R4)(R5)−L’−基数を表し、
R7は、アラルキル、アリール、アルケニル、アルキニルまたはC2以上のアルキル基であり、ここで、これらは場合により置換されていてもよく、ヒドロカルビル基の場合には、この上でR1、R2、R3、R4およびR5に関して定義した置換基と同等な置換基から選択される1個以上の置換基で置換されていてもよいが、但しR7がアルケニルまたはアルキニルの場合にはこれがビニル型アルファ炭素を含まないことを条件とする]
で描写可能である。
で表される高沸点の酸と式(III)
R1、R2、R3、R4、R5、L’およびnは、この上で定義した通りであるが、但し式I中のR1、R2、R3、R4またはR5が−O−Z−R8基の場合にはそれらは式III中では−O−Z−R10基に置き換わっていてもよく、
R9は、この上に示したR7と同様に定義されるが、但しR9はまた水素またはC1アルキルであってもよく、かつR9を伴って前記エステルから生じる酸(R9ZOH)が沸騰する温度の方が式(II)の酸R7ZOHが沸騰する温度より低いことを条件とし、
R10は、この上に示したR7と同様に定義されるが、但しR10はまた水素またはC1アルキルであってもよく、かつR10を伴って前記エステルから生じる酸(R10ZOH)が沸騰する温度の方が式(II)の酸R7ZOHが沸騰する温度より低いことを条件とする]
で表される低沸点の酸のシリルエステルを反応させながら生じた式(IV)および/または(V)
R9ZOH (IV)
R10ZOH (V)
で表される酸基をその系から除去することで前記式(I)の少なくとも1種の保護された酸基を生じさせることで実施可能である。
A. 不飽和酸(例えばアクリル酸、マレイン酸またはフマル酸)および二酸のモノエステルとロジンの付加体。
B. ロジン自身の付加体(二量化したロジン、オリゴマー化または重合したロジン)。
C. 水添もしくは部分水添ロジン。
D. 不均化ロジン。
・ Ca、CuまたはZnの樹脂酸塩、
・ Ca、CuまたはZnのナフテン酸塩、
・ Laroflex MP(BASFから商業的に入手可能)の如きビニル、
・ Neocryl B725(Aveciaから商業的に入手可能)の如きアクリレート、
・ アクリル酸Cu/Zn/Ca、例えばEP 342276、EP 982324(Kansai)に記述されている如きアクリル酸Cu/Zn/Ca、またはポリエステル、例えばEP 1033392(Kansai)に記述されている如きポリエステル、
・ トリ−オルガノシリル(メタ)アクリレート共重合体、例えばEP 131626(M&T)、米国特許第4593055号(M&T)、EP 775773(Chugoku)、EP 646630(NOF)、米国特許第5436284号(NOF)、WO 0162811およびWO 0162858(SIGMA COATINGS)に記述されている如きトリ−オルガノシリル(メタ)アクリレート共重合体、親水性(メタ)アクリレート、例えばFR 2 557 585(Jotun)、EP 526441およびEP 289441(SIGMA COATINGS)に記述されている如き親水性(メタ)アクリレート。
Xは酸素または硫黄であり、Yは窒素、CHまたはC(C1−4アルコキシ)であり、そしてC6環はC1−4置換基を1個持っていてもよく、場合により5位もしくは6位にC1−4アルキルまたはベンジルから選択される2番目の置換基が存在していてもよい]
で表される置換基に相当する置換基を有する1,4,2−オキサチアジンのモノ−およびジ−オキサイドが含まれる。
製品1
冷却器と受け槽が付いている蒸留塔と機械的撹拌機を装備しておいた5Lの反応槽にForal AX−Eを2.66kgおよびエチルトリアセトキシシランを0.61kg入れた。この混合物を155℃、即ち酢酸の初期留出温度になるまで加熱した。温度をゆっくり上昇させることで蒸留を継続した。温度が175℃の時に酢酸の留出が終わった。蒸留を減圧(100−500ミリバール)下で1時間行うことで反応を完了させた。酢酸の収量は452ml(97%)であった。残存するオルガノシリルエステルをキシレンで固体量が69.1%になるまで希釈した。この溶液の粘度は7cPa.sであった。
製品2
冷却器と受け槽が付いている蒸留塔と機械的撹拌機を装備しておいた反応槽にインドンシアのゴムロジンを817g、エチルトリアセトキシシランを211gおよびキシレンを578g入れた。塔頂部温度を115℃にしながら前記混合物を135℃、即ちキシレン/酢酸共沸混合物の初期留出温度になるまで加熱した。温度を160℃になるまでゆっくり上昇させた。留出液を390ml得た後に追加的200mlのキシレンを前記反応混合物に加えた。その後、蒸留を650mlの留出液が得られかつ塔頂部温度が136℃の温度に到達するまで継続した。酢酸の収率は99.5%であった。残存する樹脂の固体量は78%で粘度は170cPa.sであった。
製品9(水添ロジンの転化)
機械的撹拌機と蒸留用冷却器を装備しておいた0.5LのフラスコにForal AX−Eを84g、キシレンを18g、アセトキシトリメチルシランを33gおよびシクロヘキサンを206g加えた。この混合物を撹拌しながら加熱(85−105℃)することでシクロヘキサンと酢酸の全部を留出させた。留出させる酢酸の最終収率である97.3%に到達させるにはシクロヘキサンを100mlと150mlの2回再添加する必要があった。残存する樹脂酸トリメチルシリル溶液の粘度は20cPa.sで固体量は83%であった(24時間、60℃)。
製品10
冷却器と受け槽が付いている小型カラムと機械的撹拌機と温度制御装置を装備しておいた1.2LのフラスコにForal AX−Eを263gおよびDymerexを308g入れた。この混合物を220℃になるまで加熱することで溶融させた。次に、エチルシリルトリアセテートを120g加えた。酢酸の留出が155℃の時に始まって175℃の時に終了した。操作を減圧(150ミリバール)下で1時間行うことで蒸留を継続した。酢酸が93g留出し、これは生じ得る酸の101%であった。残存する樹脂を400gのキシレンで溶解させた後、周囲温度になるまで冷却した。測定固体量は60%であった。この溶液の粘度は30cPa.sであった。
固体含有量の測定
サンプルを120℃に1時間加熱する前と後の重量を計ることで固体含有量を測定した(標準的試験方法ISO 3233/ASTM 2697/DIN 53219)。(表1、%)
粘度の測定
ブルックフィールドを25℃で用いて結合剤溶液および塗料の粘度を測定した(ASTM試験方法D2196−86)。(表1、cPa.s)
結合剤が示す加水分解性の評価
ドローダウン(draw−downs)をアルカリ溶液(NaOH、pH12.0−13.4)に浸漬しそして加水分解が観察されるまでの分(誘導時間)を測定することで加水分解性を評価した。
Claims (25)
- カルボン酸、スルホン酸もしくは燐酸のオルガノシリルエステルを塗料配合物の結合剤系用のアルカリ加水分解もしくは侵食推進剤として使用する方法。
- 前記塗料配合物のいずれかで2種以上のカルボン酸、スルホン酸もしくは燐酸シリルエステルを用いる、即ち前記シリルエステルの混合物を推進剤として用いる請求項1記載の使用方法。
- 前記オルガノシリルエステルのカルボン酸、スルホン酸もしくは燐酸部分が非ビニル型アルファ炭素を有する請求項1または2記載の使用方法。
- 前記結合剤系が膜形成結合剤を含んで成る請求項1−3のいずれか1項記載の使用方法。
- 本発明のオルガノシリルエステルもまた単独で膜を形成する請求項1〜4のいずれか1項記載の使用方法。
- 塗料組成物用膜もしくは樹脂性結合剤であって、ロジン以外であるアルファ炭素が非ビニル型のカルボン酸、スルホン酸もしくは燐酸のオルガノシリルエステルを含んで成る塗料組成物用膜もしくは樹脂性結合剤。
- ロジン以外であるアルファ炭素が非ビニル型のモノカルボン酸、スルホン酸もしくは燐酸のオルガノシリルエステルを塗料用結合剤系の結合剤成分として用いる使用方法。
- 塗料組成物であって、ロジン以外であるアルファ炭素が非ビニル型のモノカルボン酸、スルホン酸もしくは燐酸のオルガノシリルエステルを含んで成る塗料組成物。
- 該塗料が結合剤系を含んで成っていて前記結合剤系が前記モノカルボン酸、スルホン酸もしくは燐酸のオルガノシリルエステルを結合剤成分として含んで成る請求項8記載の塗料組成物。
- 塗料組成物であって、ロジン以外のモノカルボン酸、スルホン酸もしくは燐酸のシリルエステルを結合剤系の結合剤成分として含んで成る塗料組成物。
- カルボン酸、スルホン酸もしくは燐酸のオルガノシリルエステルの混合物が存在する請求項1〜10のいずれか1項記載の使用方法、結合剤もしくは塗料組成物。
- 塗料組成物の製造方法であって、該方法の1つの段階がロジン以外の酸のオルガノシリルエステルを含んで成る結合剤成分を結合剤系の結合剤成分として添加する段階であることを特徴とする塗料組成物の製造方法。
- 前記塗料が防汚塗料である請求項12記載の塗料組成物の製造方法。
- 前記カルボン酸、スルホン酸もしくは燐酸のオルガノシリルエステルがC3に等しいか或はそれ以上のヒドロカルビル残基が基になっている請求項1〜13のいずれか1項記載の使用方法、製造方法、結合剤もしくは塗料組成物。
- 前記酸のオルガノシリルエステルが一般式(I):
Zは、
各R4およびR5は、ヒドロキシルであってもよいか、或は独立して、アルキル、アリール、アルコキシル、アリールオキシル、−L’−SiR1R2R3、−L’−(SiR4R5L’)n−SiR1R2R3、−L’−SiR1R2−、−L’−(SiR4R5L’)n−SiR1R2−、アルケニル、アルキニル、アラルキルまたはアラルキルオキシル基から選択されてもよく、ここで、これらは場合によりアルキル、アルコキシル、アラルキル、アラルキルオキシル、ヒドロキシル、アリール、アリールオキシル、ハロゲン、アミノ(好適には第三級アミノ)またはアミノアルキル基を包含する群から独立して選択される1個以上の置換基で置換されていてもよく、或はR4またはR5は、独立して、−O−Z−R8基であってもよく、ここで、R8は以下に示すR7と同様に定義され、
各R1、R2およびR3は、独立して、水素、ヒドロキシル、アルキル、アルケニル、アルキニル、アルコキシル、アリール、アリールオキシル、アラルキルまたはアラルキルオキシル基を表してもよく、ここで、これらは場合によりアルキル、アルコキシル、アラルキル、アラルキルオキシル、アリール、アリールオキシル、ハロゲン、ヒドロキシル、アミノ(好適には第三級アミノ)またはアミノアルキル基を包含する群から独立して選択される1個以上の置換基で置換されていてもよく、或はR1、R2またはR3は、独立して、−O−Z−R8基であってもよく、
L’は、O、SまたはNR6(ここで、R6は以下に示すR9と同様に定義される)を表し、
各nは、独立して、0から1000の−Si(R4)(R5)−L’−基数を表し、
R7は、アラルキル、アリール、アルケニル、アルキニルまたはC2以上のアルキル基であり、ここで、これらは場合により置換されていてもよく、ヒドロカルビル基の場合には、この上でR1、R2、R3、R4およびR5に関して定義した置換基と同等な置換基から選択される1個以上の置換基で置換されていてもよい]
で表される請求項1〜14のいずれか1項記載の使用方法、製造方法、結合剤もしくは塗料組成物。 - 式(I)
Zは、
各R4およびR5は、ヒドロキシルであってもよいか、或は独立して、アルキル、アリール、アルコキシル、アリールオキシル、−L’−SiR1R2R3、−L’−(SiR4R5L’)n−SiR1R2R3、−L’−SiR1R2−、−L’−(SiR4R5L’)n−SiR1R2−、アルケニル、アルキニル、アラルキルまたはアラルキルオキシル基から選択されてもよく、ここで、これらは場合によりアルキル、アルコキシル、アラルキル、アラルキルオキシル、ヒドロキシル、アリール、アリールオキシル、ハロゲン、アミノ(好適には第三級アミノ)またはアミノアルキル基を包含する群から独立して選択される1個以上の置換基で置換されていてもよく、或はR4またはR5は、独立して、−O−Z−R8基であってもよく、ここで、R8は以下に示すR7と同様に定義され、
各R1、R2およびR3は、独立して、水素、ヒドロキシル、アルキル、アルケニル、アルキニル、アルコキシル、アリール、アリールオキシル、アラルキルまたはアラルキルオキシル基を表してもよく、ここで、これらは場合によりアルキル、アルコキシル、アラルキル、アラルキルオキシル、アリール、アリールオキシル、ハロゲン、ヒドロキシル、アミノ(好適には第三級アミノ)またはアミノアルキル基を包含する群から独立して選択される1個以上の置換基で置換されていてもよく、或はR1、R2またはR3は、独立して、−O−Z−R8基であってもよく、
L’は、O、SまたはNR6(ここで、R6は以下に示すR9と同様に定義される)を表し、
各nは、独立して、0から1000の−Si(R4)(R5)−L’−基数を表し、
R7は、アラルキル、アリール、アルケニル、アルキニルまたはC2以上のアルキル基であり、ここで、これらは場合により置換されていてもよく、ヒドロカルビル基の場合には、この上でR1、R2、R3、R4およびR5に関して定義した置換基と同等な置換基から選択される1個以上の置換基で置換されていてもよいが、但しR7がアルケニルまたはアルキニルの場合にはこれがビニル型アルファ炭素を含まないことを条件とする]
で表されるシリルエステルを製造する方法であって、式(II)
で表される高沸点の酸と式(III)
R1、R2、R3、R4、R5、L’およびnは、この上で定義した通りであるが、但し式I中のR1、R2、R3、R4またはR5が−O−Z−R8基の場合にはそれらは式III中では−O−Z−R10基に置き換わっていてもよく、
R9は、この上に示したR7と同様に定義されるが、但しR9はまた水素またはC1アルキルであってもよく、かつR9を伴って前記エステルから生じる酸(R9ZOH)が沸騰する温度の方が式(II)の酸R7ZOHが沸騰する温度より低いことを条件とし、
R10は、この上に示したR7と同様に定義されるが、但しR10はまた水素またはC1アルキルであってもよく、かつR10を伴って前記エステルから生じる酸(R10ZOH)が沸騰する温度の方が式(II)の酸R7ZOHが沸騰する温度より低いことを条件とする]
で表される低沸点の酸のシリルエステルを反応させながら生じた式(IV)および/または(V)
R9ZOH (IV)
R10ZOH (V)
で表される酸基をその系から除去することで前記式(I)の少なくとも1種の保護された酸基を生じさせる方法。 - 生じさせた式Iに従うアシル化シリルエステルが1個または数個のケイ素原子と結合しているアシルオキシ基を2個以上有する請求項15または16記載の使用方法、製造方法、結合剤または塗料組成物。
- 式(IV)のカルボキシル基部分がホルミル、アセチル、プロピオニルおよびブチリルから選択される請求項15−17のいずれか1項記載の使用方法、製造方法、結合剤または塗料組成物。
- 式R7ZOHのカルボキシル基部分の例に、独立して、これらに限定するものでないが、プロピオニル、ブチリル、ピバロイル、オクザロイル、マロニル、スクシニル、グルタリル、アジポイル、ベンゾイル、フタロイル、イソブチロイル、s−ブチロイル、オクタノイル、イソオクタノイル、ノナノイル、イソノナノイル、アビエチル、デヒドロアビエチル、ジヒドロアビエチル、ナフテニル、アントラセニル、アビエチル二量体[Dymerex(商標)]、完全水添ジヒドロアビエチル[Foral(商標)]などおよびこれらの重合体もしくは共重合体が含まれ得る請求項15−18のいずれか1項記載の使用方法、製造方法、結合剤または塗料組成物。
- 一般式(III)で表されるオルガノシリル化カルボキシレート化合物の例に、これらに限定するものでないが、トリメチルシリルホルメート、ジメチルシリルジホルメート、メチルシリルトリホルメート、トリ−n−ブチル 1−アセトキシ−シラン、ジ−n−ブチル 1,1−ジアセトキシ−シラン、n−ブチル 1,1,1−トリアセトキシ−シラン、トリ−n−プロピル−1−アセトキシシラン、ジ−n−プロピル 1,1−ジアセトキシ−シラン、n−プロピル 1,1,1−トリアセトキシ−シラン、トリ−t−ブチル−1−アセトキシ−シラン、トリ−イソプロピル−1−アセトキシ−シラン、トリ−イソブチル−1−アセトキシ−シラン、トリ−メチル−1−アセトキシ−シラン、ジ−メチル 1,1−ジアセトキシ−シラン、メチル 1,1,1−トリアセトキシ−シラン、トリエチル−1−アセトキシ−シラン、ジエチル−1,1−ジアセトキシ−シラン、エチル 1,1,1−トリアセトキシ−シラン、ビニル 1,1,1−トリアセトキシ−シラン、トリベンジル−1−アセトキシ−シラン、トリアミル−1−アセトキシ−シラン、トリフェニル−1−アセトキシ−シラン、トリメチルシリルプロピオネート、t−ブチルジメチルシリルアセテート、ペンタメチル−1−アセトキシ−ジシロキサン、ヘプタメチル−1−アセトキシ−トリシロキサン、ノナメチル−1−アセトキシ−テトラシロキサン、ノナエチル−1−アセトキシ−テトラシロキサン、ノナ−t−ブチル−1−アセトキシ−テトラシロキサン、ノナベンジル−1−アセトキシ−テトラシロキサン、ノナ−イソプロピル−1−アセトキシ−テトラシロキサン、ノナ−n−プロピル−1−アセトキシ−テトラシロキサン、ノナ−イソブチル−1−アセトキシ−テトラシロキサン、ノナ−アミル−1−アセトキシ−テトラシロキサン、ノナ−n−ブチル−1−アセトキシ−テトラシロキサン、ノナ−ドデシル−1−アセトキシ−テトラシロキサン、ノナ−ヘキシル−1−アセトキシ−テトラシロキサン、ノナ−フェニル−1−アセトキシ−テトラシロキサン、ノナ−オクチル−1−アセトキシ−テトラシロキサン、ウンデカメチル−1−アセトキシ−ペンタシロキサン、ウンデカエチル−1−アセトキシ−ペンタシロキサン、ウンデカ−t−ブチル−1−アセトキシ−ペンタシロキサン、ウンデカベンジル−1−アセトキシ−ペンタシロキサン、ウンデカ−イソプロピル−1−アセトキシ−ペンタシロキサン、ウンデカ−n−プロピル−1−アセトキシ−ペンタシロキサン、ウンデカ−イソブチル−1−アセトキシ−ペンタシロキサン、ウンデカ−アミル−1−アセトキシ−ペンタシロキサン、ウンデカ−n−ブチル−1−アセトキシ−ペンタシロキサン、ウンデカ−ドデシル−1−アセトキシ−ペンタシロキサン、ウンデカ−ヘキシル−1−アセトキシ−ペンタシロキサン、ウンデカ−フェニル−1−アセトキシ−ペンタシロキサン、ウンデカ−オクチル−1−アセトキシ−ペンタシロキサン、トリデカメチル−1−アセトキシ−ヘキサシロキサン、トリデカエチル−1−アセトキシ−ヘキサシロキサン、トリデカ−t−ブチル−1−アセトキシ−ヘキサシロキサン、トリデカベンジル−1−アセトキシ−ヘキサシロキサン、トリデカ−イソプロピル−1−アセトキシ−ヘキサシロキサン、トリデカ−n−プロピル−1−アセトキシ−ヘキサシロキサン、トリデカ−イソブチル−1−アセトキシ−ヘキサシロキサン、トリデカ−アミル−1−アセトキシ−ヘキサシロキサン、トリデカ−n−ブチル−1−アセトキシ−ヘキサシロキサン、トリデカ−ドデシル−1−アセトキシ−ヘキサシロキサン、トリデカ−ヘキシル−1−アセトキシ−ヘキサシロキサン、トリデカ−フェニル−1−アセトキシ−ヘキサシロキサン、トリデカ−オクチル−1−アセトキシ−ヘキサシロキサンが含まれる請求項16−19のいずれか1項記載の使用方法、製造方法、結合剤または塗料組成物。
- 一般式(III)で表されるオルガノシリル化カルボキシレート化合物がエチルトリアセトキシシラン、ビニルトリアセトキシシラン、ジメチルジアセトキシシランおよびトリメチルシリルアセテートから選択される請求項16−20のいずれか1項記載の使用方法、製造方法、結合剤または塗料組成物。
- 本発明のシリルエステルを生じさせる目的でシリル化を受けさせることができる高沸点酸の例にC3以上の酸、即ちプロピオン酸に等しいか或はそれ以上の脂肪酸同族体、例えばC4−C60酸、例えばイソステアリン酸など、環状脂肪酸、例えばナフテン酸など、およびC4−C60酸(芳香または不飽和酸を包含)、例えば水添ロジンなどが含まれる請求項15−21のいずれか1項記載の使用方法、製造方法、結合剤または塗料組成物。
- 本発明のシリルエステルと組合わせて使用可能な共結合剤が
・ Ca、CuまたはZnの樹脂酸塩、
・ Ca、CuまたはZnのナフテン酸塩、
・ Laroflex MP(BASFから商業的に入手可能)の如きビニル、
・ Neocryl B725(Aveciaから商業的に入手可能)の如きアクリレート、
・ アクリル酸Cu/Zn/Ca、例えばEP 342276、EP 982324(Kansai)に記述されている如きアクリル酸Cu/Zn/Ca、またはポリエステル、例えばEP 1033392(Kansai)に記述されている如きポリエステル、トリ−オルガノシリル(メタ)アクリレート共重合体、例えばEP 131626(M&T)、米国特許第4593055号(M&T)、EP 775773(Chugoku)、EP 646630(NOF)、米国特許第5436284号(NOF)、WO 0162811およびWO 0162858(SIGMA COATINGS)に記述されている如きトリ−オルガノシリル(メタ)アクリレート共重合体、親水性(メタ)アクリレート、例えばFR 2 557 585(Jotun)、EP 526441およびEP 289441(SIGMA COATINGS)に記述されている如き親水性(メタ)アクリレート、
から選択されてもよい請求項1〜22のいずれか1項記載の使用方法、製造方法、結合剤または塗料組成物。 - 本発明のシリルエステルと組合わせて使用可能な共結合剤がトリオルガノシリル(メタ)アクリレート共重合体から選択される請求項23記載の使用方法、製造方法、結合剤または塗料組成物。
- 前記結合剤が示す膜形成特性の向上に役立つように前記結合剤に多官能酸、例えばポリ(シリルエステル)またはDymerex(商標)などが混合されている請求項24記載の使用方法、製造方法、結合剤または塗料組成物。
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- 2004-05-07 JP JP2006505410A patent/JP2006525396A/ja active Pending
- 2004-05-07 KR KR1020057021085A patent/KR101233715B1/ko active IP Right Grant
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Also Published As
Publication number | Publication date |
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CN100393822C (zh) | 2008-06-11 |
NO20055366L (no) | 2005-11-11 |
US8148446B2 (en) | 2012-04-03 |
US20070161722A1 (en) | 2007-07-12 |
US20100249298A1 (en) | 2010-09-30 |
KR101233715B1 (ko) | 2013-02-18 |
CN1784478A (zh) | 2006-06-07 |
WO2004099326A3 (en) | 2005-05-06 |
WO2004099326A2 (en) | 2004-11-18 |
EP1620514A2 (en) | 2006-02-01 |
KR20060012594A (ko) | 2006-02-08 |
EP1475415A1 (en) | 2004-11-10 |
NO337528B1 (no) | 2016-05-02 |
US8153705B2 (en) | 2012-04-10 |
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