DE3706095C2 - Polysiloxan-Makromonomer und dessen Verwendung zur Herstellung eines Polysiloxan-haltigen Harzes - Google Patents
Polysiloxan-Makromonomer und dessen Verwendung zur Herstellung eines Polysiloxan-haltigen HarzesInfo
- Publication number
- DE3706095C2 DE3706095C2 DE3706095A DE3706095A DE3706095C2 DE 3706095 C2 DE3706095 C2 DE 3706095C2 DE 3706095 A DE3706095 A DE 3706095A DE 3706095 A DE3706095 A DE 3706095A DE 3706095 C2 DE3706095 C2 DE 3706095C2
- Authority
- DE
- Germany
- Prior art keywords
- compound
- macromonomer
- polysiloxane
- groups
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- -1 Polysiloxane Polymers 0.000 title claims description 66
- 229920001296 polysiloxane Polymers 0.000 title claims description 52
- 239000011347 resin Substances 0.000 title claims description 14
- 229920005989 resin Polymers 0.000 title claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 54
- 229920002554 vinyl polymer Polymers 0.000 claims description 38
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 31
- 239000000178 monomer Substances 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000000524 functional group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 238000007334 copolymerization reaction Methods 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- FVHIPRFQVIAXIZ-UHFFFAOYSA-N 3-[disilanyl(hydroxy)silyl]propyl prop-2-enoate Chemical compound O[SiH](CCCOC(=O)C=C)[SiH2][SiH3] FVHIPRFQVIAXIZ-UHFFFAOYSA-N 0.000 claims description 5
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
- SXWUUUJQQVXKKY-UHFFFAOYSA-N disilanyl-hydroxy-phenylsilane Chemical compound [SiH3][SiH2][SiH](O)C1=CC=CC=C1 SXWUUUJQQVXKKY-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 claims description 2
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- GQSUIPLCCLCIDI-UHFFFAOYSA-N 4-triethoxysilylbutan-2-yl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCC(C)OC(=O)C(C)=C GQSUIPLCCLCIDI-UHFFFAOYSA-N 0.000 claims description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- 235000011054 acetic acid Nutrition 0.000 claims description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- SXPLZNMUBFBFIA-UHFFFAOYSA-N butyl(trimethoxy)silane Chemical compound CCCC[Si](OC)(OC)OC SXPLZNMUBFBFIA-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- SHEYKHMHFCPWCL-UHFFFAOYSA-N disilanyl-hydroxy-methylsilane Chemical compound C[SiH](O)[SiH2][SiH3] SHEYKHMHFCPWCL-UHFFFAOYSA-N 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 2
- 235000011167 hydrochloric acid Nutrition 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- 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 2
- GYZQBXUDWTVJDF-UHFFFAOYSA-N tributoxy(methyl)silane Chemical compound CCCCO[Si](C)(OCCCC)OCCCC GYZQBXUDWTVJDF-UHFFFAOYSA-N 0.000 claims description 2
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000000576 coating method Methods 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000001879 gelation Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 229920000578 graft copolymer Polymers 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000005375 organosiloxane group Chemical group 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000007870 radical polymerization initiator Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 1
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- GRPPLVAOYAMMRV-UHFFFAOYSA-N 3-(tert-butylamino)-2-methylprop-2-enoic acid Chemical compound C(C)(C)(C)NC=C(C(=O)O)C GRPPLVAOYAMMRV-UHFFFAOYSA-N 0.000 description 1
- LZMNXXQIQIHFGC-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C(C)=C LZMNXXQIQIHFGC-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 238000010559 graft polymerization reaction Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000479 mixture part Substances 0.000 description 1
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-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
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000005054 phenyltrichlorosilane Substances 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
- C08F283/124—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes on to polysiloxanes having carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Silicon Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Graft Or Block Polymers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61040923 | 1986-02-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3706095A1 DE3706095A1 (de) | 1987-08-27 |
| DE3706095C2 true DE3706095C2 (de) | 1994-05-19 |
Family
ID=12594018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3706095A Expired - Fee Related DE3706095C2 (de) | 1986-02-25 | 1987-02-25 | Polysiloxan-Makromonomer und dessen Verwendung zur Herstellung eines Polysiloxan-haltigen Harzes |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US5079312A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS62275132A (cg-RX-API-DMAC7.html) |
| DE (1) | DE3706095C2 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2603590B1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB2187747B (cg-RX-API-DMAC7.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8147923B2 (en) | 2001-06-27 | 2012-04-03 | Basf Coatings Gmbh | Method for producing coatings from coating materials that can be cured by the action of heat or actinic radiation |
Families Citing this family (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4693935A (en) * | 1986-05-19 | 1987-09-15 | Minnesota Mining And Manufacturing Company | Polysiloxane-grafted copolymer pressure sensitive adhesive composition and sheet materials coated therewith |
| JPS63221123A (ja) * | 1987-03-09 | 1988-09-14 | Kansai Paint Co Ltd | 低温硬化性樹脂組成物 |
| JP2791438B2 (ja) | 1988-09-09 | 1998-08-27 | 関西ペイント株式会社 | 樹脂組成物及びその硬化方法 |
| JPH0288639A (ja) * | 1988-09-27 | 1990-03-28 | Shin Etsu Chem Co Ltd | オルガノポリシロキサン化合物 |
| US4994538A (en) * | 1989-02-24 | 1991-02-19 | Avery International Corporation | Siliconized emulsion based pressure-sensitive adhesives |
| JPH02233752A (ja) * | 1989-03-08 | 1990-09-17 | Kansai Paint Co Ltd | 硬化性組成物 |
| DE4011044A1 (de) * | 1990-04-05 | 1991-10-10 | Fraunhofer Ges Forschung | Silane, verfahren zu ihrer herstellung und ihre verwendung zur herstellung von polymerisaten und polykondensaten |
| DE4119857A1 (de) * | 1991-06-17 | 1992-12-24 | Basf Lacke & Farben | Ueberzugsmittel auf der basis von carboxylgruppenhaltigen polymeren und epoxidharzen |
| JP3287475B2 (ja) * | 1991-12-27 | 2002-06-04 | 日本ペイント株式会社 | 硬化性樹脂組成物 |
| US5919885A (en) * | 1994-02-18 | 1999-07-06 | Fraunhofer-Gesellschaft Zur Foerderung Der Angewandten Forschung E.V. | Covalently and nucleophilically self-curing systems |
| US5491203A (en) * | 1994-09-08 | 1996-02-13 | Showa Denko K. K. | Polyorganosiloxane and process for producing the same |
| JPH08269293A (ja) * | 1995-03-30 | 1996-10-15 | Toray Dow Corning Silicone Co Ltd | 硬化性剥離剤組成物 |
| ATE282668T1 (de) * | 1995-06-05 | 2004-12-15 | Henkel Corp | Härtbare silicon-klebe- /abdichtungszusammensetzungen |
| US5605999A (en) * | 1995-06-05 | 1997-02-25 | Loctite Corporation | Anaerobically curable silicones |
| JPH1017624A (ja) * | 1996-06-28 | 1998-01-20 | Toray Dow Corning Silicone Co Ltd | シリコーン変性ビニル重合体およびその製造方法 |
| DE19723504C1 (de) | 1997-06-05 | 1998-10-15 | Basf Coatings Ag | Beschichtungsmittel, Verfahren zu seiner Herstellung und seine Verwendung als Decklack oder Klarlack, insbesondere zur Beschichtung von Kunststoffen |
| DE19728411C2 (de) | 1997-07-03 | 2001-09-27 | Basf Coatings Ag | Polyurethanharz, Verfahren zu seiner Herstellung und seine Verwendung in wäßrigen Zweikomponenten-Klarlacken |
| EP0998508B1 (de) | 1997-07-22 | 2002-10-02 | BASF Coatings AG | Beschichtungsmittel und verfahren zu dessen herstellung |
| JP3876946B2 (ja) * | 1998-01-20 | 2007-02-07 | 信越化学工業株式会社 | 帯電付与部材用コーティング剤及びそれを用いた電子写真用キャリア |
| DE19845740A1 (de) | 1998-10-05 | 2000-04-13 | Basf Coatings Ag | Beschichtungsmittel, Verfahren zu seiner Herstellung und seine Verwendung als Effekt-Klarlack, insbesondere zur Beschichtung von Kunststoffen |
| DE19846971A1 (de) | 1998-10-12 | 2000-04-20 | Basf Coatings Ag | Beschichtungsmittel, Verfahren zu seiner Herstellung und seine Verwendung als Decklack oder Klarlack, insbesondere zur Beschichtung von Kunststoffen |
| EP1137728A1 (de) | 1998-10-31 | 2001-10-04 | BASF Coatings AG | Beschichtungsmittel mit macromer-einheit für die herstellung mehrschichtiger überzüge |
| DE19850243A1 (de) | 1998-10-31 | 2000-05-11 | Basf Coatings Ag | Flüssige Stoffgemische und (Co)Polymerisate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von reaktiven Mehrstoffmischungen |
| US6180690B1 (en) * | 1998-11-04 | 2001-01-30 | E. I. Du Pont De Nemours And Company | Alkoxysilane binders as additives in ink jet inks |
| DE19904330A1 (de) | 1999-01-28 | 2000-08-10 | Basf Coatings Ag | Wäßriger Beschichtungsstoff und Modulsystem zu seiner Herstellung |
| JP2002537472A (ja) | 1999-02-25 | 2002-11-05 | ビーエーエスエフ コーティングス アクチェンゲゼルシャフト | 重ね塗り塗膜を製造するためのトリシクロデカンジメタノールの使用 |
| DE19909894A1 (de) | 1999-03-06 | 2000-09-07 | Basf Coatings Ag | Sol-Gel-Überzug für einschichtige oder mehrschichtige Lackierungen |
| DE19921457B4 (de) | 1999-05-08 | 2006-05-04 | Basf Coatings Ag | Modulsystem zur Herstellung wäßriger Beschichtungsstoffe, Verfahren zu deren Herstellung und Verwendung sowie damit hergestellte Lackierungen |
| DE19924172A1 (de) | 1999-05-25 | 2000-11-30 | Basf Coatings Ag | Beschichtungsstoff mit einer Mischung aus Kieselsäuren und Harnstoff und/oder Harnstoffderivaten |
| DE19932497A1 (de) | 1999-07-12 | 2001-01-18 | Basf Coatings Ag | Wäßriger Beschichtungsstoff, Verfahren zu seiner Herstellung und seine Verwendung |
| DE19938759A1 (de) | 1999-08-16 | 2001-02-22 | Basf Coatings Ag | Beschichtungsstoff und seine Verwendung zur Herstellung hochkratzfester mehrschichtiger Klarlackierungen |
| DE19940855A1 (de) | 1999-08-27 | 2001-03-01 | Basf Coatings Ag | Lösemittelhaltiger Beschichtungsstoff und seine Verwendung |
| DE19940857A1 (de) | 1999-08-27 | 2001-03-01 | Basf Coatings Ag | Sol-Gel-Überzug für einschichtige oder mehrschichtige Lackierungen |
| DE19940858A1 (de) | 1999-08-27 | 2001-03-01 | Basf Coatings Ag | Sol-Gel-Überzug für einschichtige oder mehrschichtige Lackierungen |
| DE19953203A1 (de) | 1999-11-05 | 2007-12-06 | Basf Coatings Ag | Verfahren zur Herstellung farb- und/oder effektgebender Mehrschichtlackierungen unter Verwendung selbstvernetzender Pfropfmischpolymerisate von Polyurethanen sowie neue selbstvernetzende Polyurethane und ihre Propfmischpolymerisate |
| DE10010405A1 (de) * | 2000-03-03 | 2001-09-13 | Basf Coatings Ag | Wäßrige (Meth)Acrylatcopolymerisat-Dispersionen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| JP2002012638A (ja) | 2000-06-30 | 2002-01-15 | Dow Corning Toray Silicone Co Ltd | 高エネルギー線硬化性組成物および樹脂成形体 |
| DE10043810A1 (de) | 2000-09-06 | 2002-04-04 | Basf Coatings Ag | Bindemittellösung und ihre Verwendung für die KFZ-Kleinstreparatur im Teil |
| US6685985B2 (en) | 2001-02-09 | 2004-02-03 | Basf Corporation | Method of improving the appearance of coated articles having both vertical and horizontal surfaces, and coating compositions for use therein |
| DE10126651A1 (de) | 2001-06-01 | 2002-12-12 | Basf Coatings Ag | Pulverlacksuspensionen (Pulverslurries) und Pulverlacke, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10200929A1 (de) * | 2002-01-12 | 2003-07-31 | Basf Coatings Ag | Polysiloxan-Sole, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10216608A1 (de) | 2002-04-15 | 2003-10-30 | Wacker Polymer Systems Gmbh | Extrudierbare, migrationsarme Silikonorganocopolymere mit hoher Transparenz, deren Herstellung und Verwendung |
| DE10321320A1 (de) * | 2003-05-13 | 2004-12-02 | Degussa Ag | Organofunktionelle Siloxangemische |
| JP4883275B2 (ja) * | 2006-02-28 | 2012-02-22 | 信越化学工業株式会社 | 硬化性組成物及び被覆物品 |
| DE102006032077A1 (de) * | 2006-07-11 | 2008-01-17 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Hybride Polymermaterialien durch Copolymerisation |
| DE102007008663A1 (de) | 2007-02-20 | 2008-08-21 | Merck Patent Gmbh | Bindemittel |
| WO2009047076A1 (de) | 2007-10-09 | 2009-04-16 | Basf Se | Mit fluoreszenzfarbstoffen markierte, pigmentfreie, wässrige polymerdispersionen, verfahren zu ihrer herstellung und ihre verwendung |
| WO2009060125A1 (en) * | 2007-11-06 | 2009-05-14 | Braggone Oy | Carbosilane polymer compositions for anti-reflective coatings |
| DE102008020441A1 (de) | 2008-04-23 | 2009-10-29 | Merck Patent Gmbh | Klebstoff |
| DE102008024868A1 (de) | 2008-05-23 | 2009-11-26 | Merck Patent Gmbh | Polymerisationsverfahren zur Herstellung von Kern-Hülle-Partikeln |
| EP2192136B1 (en) * | 2008-11-26 | 2019-02-27 | Corning Incorporated | Sol-gel-polymer nanocomposite and methods thereof |
| CN102666731B (zh) | 2009-12-04 | 2014-12-31 | 道康宁公司 | 硅倍半氧烷树脂的稳定化 |
| JP5704075B2 (ja) * | 2010-01-26 | 2015-04-22 | 日立化成株式会社 | 調光材料用（メタ）アクリロイル基含有ポリシロキサン樹脂の製造方法 |
| EP2960262A1 (en) | 2014-06-23 | 2015-12-30 | Henkel AG&Co. KGAA | Polymer system based on hydrophobically modified water soluble polymers |
| EP2960255A1 (en) | 2014-06-23 | 2015-12-30 | Henkel AG&Co. KGAA | Method of manufacturing pH responsive latexes and uses thereof |
| EP2960261A1 (en) | 2014-06-23 | 2015-12-30 | Henkel AG&Co. KGAA | Polymer system based on hydrophobically modified water soluble polymers |
| DE102014218599A1 (de) | 2014-09-16 | 2016-03-17 | Henkel Ag & Co. Kgaa | Waschmittel enthaltend vernetzte Acrylatpolymere |
| CN107636096B (zh) | 2015-05-21 | 2020-06-05 | 科思创德国股份有限公司 | 聚氨酯涂料组合物 |
| EP3133117A1 (en) | 2015-08-17 | 2017-02-22 | Henkel AG & Co. KGaA | Water-based polymer system for labeling adhesive applications |
| EP3222691A1 (en) | 2016-03-24 | 2017-09-27 | Henkel AG & Co. KGaA | Water-based polymer dispersions comprising hydrophobic antimony-free flame retardants |
| US11531269B2 (en) * | 2016-10-04 | 2022-12-20 | Nissan Chemical Corporation | Method for producing resist pattern coating composition with use of solvent replacement method |
| WO2019188426A1 (ja) * | 2018-03-26 | 2019-10-03 | 富士フイルム株式会社 | 音響波プローブ用樹脂材料、音響レンズ、音響波プローブ、音響波測定装置、超音波診断装置、光音響波測定装置及び超音波内視鏡、並びに、音響レンズの製造方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2486162A (en) * | 1942-02-26 | 1949-10-25 | Corning Glass Works | Organo-siloxanes |
| US4123472A (en) * | 1975-09-05 | 1978-10-31 | Sws Silicones Corporation | Oil resistant modified silicone composition |
| US4343927A (en) * | 1976-11-08 | 1982-08-10 | Chang Sing Hsiung | Hydrophilic, soft and oxygen permeable copolymer compositions |
| US4153641A (en) * | 1977-07-25 | 1979-05-08 | Bausch & Lomb Incorporated | Polysiloxane composition and contact lens |
| DE3106186A1 (de) * | 1981-02-19 | 1982-09-09 | Wacker-Chemie GmbH, 8000 München | Verfahren zur herstellung von organopolysiloxanen und verwendung dieser organop |
| JPH0629303B2 (ja) * | 1984-05-30 | 1994-04-20 | 三菱レイヨン株式会社 | ポリオルガノシロキサン系グラフト共重合体の製造法 |
| JPS61227509A (ja) * | 1985-04-02 | 1986-10-09 | G C Dental Ind Corp | 歯科用修復材 |
| US4618644A (en) * | 1985-04-16 | 1986-10-21 | General Electric Company | Novel silicone-containing interpenetrating polymer networks |
| JP3113231B2 (ja) * | 1998-06-23 | 2000-11-27 | キヤノン株式会社 | レンズ鏡筒 |
-
1987
- 1987-02-23 FR FR878702300A patent/FR2603590B1/fr not_active Expired - Lifetime
- 1987-02-24 JP JP62042067A patent/JPS62275132A/ja active Granted
- 1987-02-24 GB GB8704302A patent/GB2187747B/en not_active Expired - Fee Related
- 1987-02-25 DE DE3706095A patent/DE3706095C2/de not_active Expired - Fee Related
-
1990
- 1990-05-11 US US07/522,401 patent/US5079312A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8147923B2 (en) | 2001-06-27 | 2012-04-03 | Basf Coatings Gmbh | Method for producing coatings from coating materials that can be cured by the action of heat or actinic radiation |
Also Published As
| Publication number | Publication date |
|---|---|
| US5079312A (en) | 1992-01-07 |
| GB8704302D0 (en) | 1987-04-01 |
| JPH0564965B2 (cg-RX-API-DMAC7.html) | 1993-09-16 |
| JPS62275132A (ja) | 1987-11-30 |
| FR2603590A1 (fr) | 1988-03-11 |
| GB2187747A (en) | 1987-09-16 |
| FR2603590B1 (fr) | 1991-05-24 |
| GB2187747B (en) | 1990-05-09 |
| DE3706095A1 (de) | 1987-08-27 |
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| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: BARZ, P., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 80803 MUENCHEN |
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| 8339 | Ceased/non-payment of the annual fee |