JPH0533247B2 - - Google Patents
Info
- Publication number
- JPH0533247B2 JPH0533247B2 JP60143341A JP14334185A JPH0533247B2 JP H0533247 B2 JPH0533247 B2 JP H0533247B2 JP 60143341 A JP60143341 A JP 60143341A JP 14334185 A JP14334185 A JP 14334185A JP H0533247 B2 JPH0533247 B2 JP H0533247B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- macromonomer
- carbon atoms
- methacrylate
- 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 - Lifetime
Links
- 125000005370 alkoxysilyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- -1 mercaptosilane compound Chemical class 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 10
- 229920002554 vinyl polymer Polymers 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000178 monomer Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 5
- 238000012643 polycondensation polymerization Methods 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- IKYAJDOSWUATPI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propane-1-thiol Chemical compound CO[Si](C)(OC)CCCS IKYAJDOSWUATPI-UHFFFAOYSA-N 0.000 description 4
- BVFSYZFXJYAPQJ-UHFFFAOYSA-N butyl(oxo)tin Chemical compound CCCC[Sn]=O BVFSYZFXJYAPQJ-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000013508 migration Methods 0.000 description 4
- 230000005012 migration Effects 0.000 description 4
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-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
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- ZNJXRXXJPIFFAO-UHFFFAOYSA-N 2,2,3,3,4,4,5,5-octafluoropentyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)C(F)(F)C(F)(F)C(F)F ZNJXRXXJPIFFAO-UHFFFAOYSA-N 0.000 description 2
- RMCCONIRBZIDTH-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 1,3-dioxo-2-benzofuran-5-carboxylate Chemical compound CC(=C)C(=O)OCCOC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 RMCCONIRBZIDTH-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 description 2
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- IDXCKOANSQIPGX-UHFFFAOYSA-N (acetyloxy-ethenyl-methylsilyl) acetate Chemical compound CC(=O)O[Si](C)(C=C)OC(C)=O IDXCKOANSQIPGX-UHFFFAOYSA-N 0.000 description 1
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 1
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- VHJHZYSXJKREEE-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropyl prop-2-enoate Chemical compound FC(F)C(F)(F)COC(=O)C=C VHJHZYSXJKREEE-UHFFFAOYSA-N 0.000 description 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- UNNCLSDBQFXTAK-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 2,4-dimethylpentanenitrile Chemical compound N(=NC(C#N)(C)C)C(C#N)(C)C.CC(C#N)CC(C)C UNNCLSDBQFXTAK-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-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
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- MTLWTRLYHAQCAM-UHFFFAOYSA-N 2-[(1-cyano-2-methylpropyl)diazenyl]-3-methylbutanenitrile Chemical compound CC(C)C(C#N)N=NC(C#N)C(C)C MTLWTRLYHAQCAM-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
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- YXYJVFYWCLAXHO-UHFFFAOYSA-N 2-methoxyethyl 2-methylprop-2-enoate Chemical compound COCCOC(=O)C(C)=C YXYJVFYWCLAXHO-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- HXLAEGYMDGUSBD-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN HXLAEGYMDGUSBD-UHFFFAOYSA-N 0.000 description 1
- ITSZNKWGCBRYQB-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propanenitrile Chemical compound CCO[Si](C)(OCC)CCC#N ITSZNKWGCBRYQB-UHFFFAOYSA-N 0.000 description 1
- KNTKCYKJRSMRMZ-UHFFFAOYSA-N 3-chloropropyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CCCCl KNTKCYKJRSMRMZ-UHFFFAOYSA-N 0.000 description 1
- NUXLDNTZFXDNBA-UHFFFAOYSA-N 6-bromo-2-methyl-4h-1,4-benzoxazin-3-one Chemical compound C1=C(Br)C=C2NC(=O)C(C)OC2=C1 NUXLDNTZFXDNBA-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 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
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical class [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- AJDTZVRPEPFODZ-PAMPIZDHSA-J [Sn+4].[O-]C(=O)\C=C/C([O-])=O.[O-]C(=O)\C=C/C([O-])=O Chemical compound [Sn+4].[O-]C(=O)\C=C/C([O-])=O.[O-]C(=O)\C=C/C([O-])=O AJDTZVRPEPFODZ-PAMPIZDHSA-J 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229940117913 acrylamide Drugs 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003373 anti-fouling effect Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- GYQKYMDXABOCBE-UHFFFAOYSA-N chloro-dimethoxy-methylsilane Chemical compound CO[Si](C)(Cl)OC GYQKYMDXABOCBE-UHFFFAOYSA-N 0.000 description 1
- XGLLBUISUZEUMW-UHFFFAOYSA-N chloromethyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(CCl)OCC XGLLBUISUZEUMW-UHFFFAOYSA-N 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- YOQPKXIRWPWFIE-UHFFFAOYSA-N ctk4c8335 Chemical compound CC(=C)C(=O)OCCOP(=O)=O YOQPKXIRWPWFIE-UHFFFAOYSA-N 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- ZMAPKOCENOWQRE-UHFFFAOYSA-N diethoxy(diethyl)silane Chemical compound CCO[Si](CC)(CC)OCC ZMAPKOCENOWQRE-UHFFFAOYSA-N 0.000 description 1
- ZZNQQQWFKKTOSD-UHFFFAOYSA-N diethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OCC)(OCC)C1=CC=CC=C1 ZZNQQQWFKKTOSD-UHFFFAOYSA-N 0.000 description 1
- GAURFLBIDLSLQU-UHFFFAOYSA-N diethoxy(methyl)silicon Chemical compound CCO[Si](C)OCC GAURFLBIDLSLQU-UHFFFAOYSA-N 0.000 description 1
- VJYNTADJZPKUAF-UHFFFAOYSA-N diethoxy-methyl-(3,3,3-trifluoropropyl)silane Chemical compound CCO[Si](C)(OCC)CCC(F)(F)F VJYNTADJZPKUAF-UHFFFAOYSA-N 0.000 description 1
- DJVQMRRXRRBRIH-UHFFFAOYSA-N diethoxy-methyl-octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](C)(OCC)OCC DJVQMRRXRRBRIH-UHFFFAOYSA-N 0.000 description 1
- MNFGEHQPOWJJBH-UHFFFAOYSA-N diethoxy-methyl-phenylsilane Chemical compound CCO[Si](C)(OCC)C1=CC=CC=C1 MNFGEHQPOWJJBH-UHFFFAOYSA-N 0.000 description 1
- ZXPDYFSTVHQQOI-UHFFFAOYSA-N diethoxysilane Chemical compound CCO[SiH2]OCC ZXPDYFSTVHQQOI-UHFFFAOYSA-N 0.000 description 1
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 1
- CVQVSVBUMVSJES-UHFFFAOYSA-N dimethoxy-methyl-phenylsilane Chemical compound CO[Si](C)(OC)C1=CC=CC=C1 CVQVSVBUMVSJES-UHFFFAOYSA-N 0.000 description 1
- YQGOWXYZDLJBFL-UHFFFAOYSA-N dimethoxysilane Chemical compound CO[SiH2]OC YQGOWXYZDLJBFL-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-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
- AILBOMWJRYLVFG-UHFFFAOYSA-N dodecyl-diethoxy-methylsilane Chemical compound CCCCCCCCCCCC[Si](C)(OCC)OCC AILBOMWJRYLVFG-UHFFFAOYSA-N 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- MBGQQKKTDDNCSG-UHFFFAOYSA-N ethenyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(C=C)OCC MBGQQKKTDDNCSG-UHFFFAOYSA-N 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- NPOYZXWZANURMM-UHFFFAOYSA-N ethoxy-[ethoxy(dimethyl)silyl]oxy-dimethylsilane Chemical compound CCO[Si](C)(C)O[Si](C)(C)OCC NPOYZXWZANURMM-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
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 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
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical compound CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pentâ4âenâ2âone Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000007717 redox polymerization reaction Methods 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- KEROTHRUZYBWCY-UHFFFAOYSA-N tridecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C(C)=C KEROTHRUZYBWCY-UHFFFAOYSA-N 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- DJXRIQMCROIRCZ-XOEOCAAJSA-N vibegron Chemical compound C1([C@H]([C@@H]2N[C@H](CC=3C=CC(NC(=O)[C@H]4N5C(=O)C=CN=C5CC4)=CC=3)CC2)O)=CC=CC=C1 DJXRIQMCROIRCZ-XOEOCAAJSA-N 0.000 description 1
Landscapes
- Silicon Polymers (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
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å¯çæ§ãä»äžãããæ°èŠãªããªããŒã§ãããDETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention is useful as an alkoxysilyl group-containing condensable macromonomer, more specifically, as an intermediate for a comb-shaped polymer having an organopolysiloxane as a main chain and a vinyl polymer as a side chain. This invention relates to a novel macromonomer and its production method. The above-mentioned comb-shaped polymer is a novel polymer that has surface migration properties and can impart water repellency (for paint) and adhesion.
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ã³ã¹ãçã«ãé«ãã€ããªã©ã®æ¬ ç¹ããã€ããPrior Art and Problems to be Solved In recent years, various functional polymers have been synthesized in the field of polymer synthesis. Among these, certain types of block polymers, graft polymers, and comb-shaped polymers are already known as having surface migration properties. However, the synthesis of these polymers has disadvantages such as poor yields of the desired product, complex reactions involving multiple steps, and high costs.
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ããã Therefore, the present inventors conducted intensive research to create a new polymer with surface migration properties easily and at low cost. As a result, the present inventors used a mercaptosilane compound having a dialkoxysilyl group as a chain transfer agent and a vinyl monomer. The polymer obtained by polymerization and having an alkoxysilyl group at the end functions as a condensable macromonomer, and the desired comb-shaped polymer can be obtained by condensation polymerization of this polymer alone or in combination with a dialkoxysilane compound. I found it.
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ããããšã«ããã The present invention was completed based on this knowledge, and its purpose is to provide an intermediate for the above-mentioned comb-shaped polymer.
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ã§ãããStructure and Effects of the Invention In other words, the present invention has the following features: [In the formula, R 1 and R 2 are the same or different alkyl groups each having 1 to 4 carbon atoms, and R 3 is -
OR 1 , -OR 2 or an alkyl group having 1 to 4 carbon atoms,
and R 4 is an alkylene group having 1 to 4 carbon atoms]; and at least one mercaptosilane compound represented by the formula, [In the formula, R 5 is hydrogen or a methyl group, and X 1
is an alkyloxycarbonyl group, a substituted alkyloxycarbonyl group, a cycloalkyloxycarbonyl group, or a phenyl group. , [In the formula, R 5 and X 1 have the same meanings as above] Consisting of 10,000 to 10,000 repeating units of at least one of the following, and CH 2 at one end has the formula, To obtain an alkoxysilyl group-containing condensable macromonomer having a dialkoxysilyl group [wherein R 1 , R 2 , R 3 and R 4 have the same meanings as above] and having H at the other end. The present invention provides a method for producing an alkoxysilyl group-containing condensable macromonomer characterized by the following, and (2) the above-mentioned alkoxysilyl group-containing condensable macromonomer obtained by the production method.
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0.01ãïŒéšã®ç¯å²ã§éžå®ããã°ããã Specific examples of the zircaptosilane compound of the above formula [] used in the present invention include mercaptomethylmethyldime(et)toxysilane (dimethoxysilane and diethoxysilane are referred to hereinafter), mercaptomethylethyldime(et)toxysilane, 2 -mercaptoethylmethyldime(eth)toxysilane, 2-mercaptoethylethyldime(eth)toxysilane, 3-
Mercaptopropylmethyldime(et)toxysilane, 3-mercaptopropylethyldime(et)toxysilane, 4-mercaptobutylmethyldime(et)toxysilane, 4-mercaptobutylethyldime(et)toxysilane
Examples include toxisilane, and one or more of these may be used. The amount used is usually per 100 parts (parts by weight, same below) of vinyl monomer.
It may be selected within the range of 0.01 to 5 parts.
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ãã¯ïŒçš®ä»¥äžã䜿çšã«äŸããã Vinyl monomer used in the present invention []
refers to monomers having a vinyl group, vinylene group, or vinylidene group, and specifically, for example, ethyl acrylate, propyl acrylate, n-butyl acrylate, isobutyl acrylate, amyl acrylate, hexyl acrylate, 2-
Ethylhexyl acrylate, cyclohexyl acrylate, n-octyl acrylate, methyl acrylate, glycidyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, 2-ethylhexyl methacrylate, lauryl methacrylate ,
Tridecyl methacrylate, benzyl methacrylate, cyclohexyl methacrylate, tetrahydrofurfuryl methacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, glycidyl methacrylate, 2
-Methoxyethyl methacrylate, 2-ethoxyethyl methacrylate, 2,2,3,3-tetrafluoropropyl acrylate, octafluoropentyl acrylate, octafluoropentyl methacrylate, styrene, etc., and in place of or in combination with these. For example, maleic anhydride, vinyl acetate, 4-META (4-methacryloxyethyl trimellitic anhydride),
HEMAP (acid phosphooxyethyl methacrylate), methacrylic acid, acrylic acid, vinyl propionate, vinyl versatate (trade name Beova, manufactured by Ciel Chemical), vinyl chloride, acrylonitrile, acryl amide, N-methylol acrylic amide, vinyl Examples include pyridine, vinylpyrrolidone, butadiene, and the like. One or more of these may be used.
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ãšãã§ããã The alkoxysilyl group-containing condensable macromonomer according to the present invention can be produced according to the following procedure.
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ããŠãããªããŠãããã A predetermined proportion of the mercaptosilane compound [ ] is blended with the above vinyl monomer [ ], and these are polymerized by heat or light under conventional conditions in the presence of a radical initiator if necessary. This polymerization may be carried out without a solvent or in a solution, but emulsion polymerization or suspension polymerization in which water coexists is not very preferable because the alkoxysilyl group of the mercaptosilane compound [] may be hydrolyzed. The above radical initiator is usually used per 100 parts of vinyl monomer.
It may be used in the range of 0.005 to 0.1 part, and specific examples include 2,2'-azobisisobutyronitrile (AIBN), 2,2'-azobisisovaleronitrile, 2,2'-azobisisobutyronitrile (2,4-dimethylvaleronitrile), benzoyl peroxide (BPO), t-
Butyloperoxide, methyl ethyl ketone peroxide, etc., or a combination of a redox catalyst (transition metal salt, amine, etc.) used in redox polymerization and a peroxide radical initiator may be employed.
In addition, in the case of photopolymerization, the radical initiator may or may not be used.
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ããšãã§ããã By polymerizing the vinyl monomer [] and the mercaptosilane compound [], the condensable macromonomer of the present invention having an alkoxysilyl group at the terminal can be obtained. The structure when one type of monomer [] and one type of mercaptosilane compound [] are used can be shown by the following formula [I].
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ãåŸãããšãã§ããã [In the formula, R 1 , R 2 , R 3 , R 4 , R 5 and X 1 have the same meanings as above, and n is an integer from 10,000 to 10,000] In addition, when BPO is used as a radical initiator teeth,
Benzoic acid decomposed and generated during radical polymerization acts as a catalyst, and if water is present in the system, condensation polymerization described below occurs simultaneously, making it possible to obtain a comb-shaped polymer in a one-step reaction.
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ã補é ãããã The condensable macromonomer of the present invention is useful as an intermediate for a comb-shaped polymer, which is the final objective. That is, the condensable macromonomer may be used alone or with the formula, [In the formula, R 6 is an alkyl group having 1 to 4 carbon atoms or a phenyl group, R 7 and R 8 are the same or different alkyl groups having 1 to 4 carbon atoms, and
X 2 is hydrogen, alkyl group, phenyl group, chlorine, alkoxysilyl group or -NH 2 , -NH-, -SH
or an alkyl group having a -CN group] At least one dialkoxysilane compound represented by the formula is used in combination, and if necessary, the condensation polymerization is carried out in the presence of a polycondensation catalyst, for example, the above-mentioned condensable macromonomer [I] and, if necessary, one type of dialkoxysilane compound [], the formula, [In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , X 1 , X 2
and n is as defined above, is an integer of 1 to 20, and m is 0 or an integer of 1 to 10.] A silicon-containing comb-shaped polymer is produced.
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ãªã©ïŒãæãããžã¢ã«ã³ãã·ã·ã©ã³ãéžã°ããã The above dialkoxysilane compound [] can further improve various physical properties such as adhesion by introducing its functional group into the main chain of the desired comb-shaped polymer. Specific examples thereof include N-(2-amino ethyl)-3-
Aminopropylmethyldimethoxysilane, 3-
Aminopropylmethyldiethoxysilane, chloromethylmethyldiethoxysilane, 3-chloropropylmethyldimethoxysilane, 2-cyanoethylmethyldiethoxysilane, diethyldiethoxysilane, dimethyldiethoxysilane, diphenyldiethoxysilane, diphenyl Dimethoxysilane, 3-mercaptopropylmethyldimethoxysilane, methyldiethoxysilane, methyldimethoxychlorosilane, methyldimethoxysilane, methyldodecyldiethoxysilane, methyloctadecyldiethoxysilane, methylphenyldiethoxysilane, methylphenyldimethoxysilane,
Dialkoxysilane compounds such as (3,3,3-trifluoropropyl)methyldiethoxysilane, vinylmethyldiacetoxysilane, vinylmethyldiethoxysilane, and 1,1,4,4-tetramethyl-1,4 -diethoxysilylethylene,
Examples include 1,1,3,3-tetramethyl-1,3-diethoxydisiloxane, and one or more of these may be used. The amount used is usually
The amount may be selected at 100 parts or less, preferably 5 parts or less, based on 100 parts of the condensable macromonomer. By using this dialkoxysilane compound, for example, dialkyldialkoxysilane is selected to improve water repellency, and dialkoxysilane having an adhesive group (-NH 2 , -SH group, etc.) is selected to improve adhesion. It will be done.
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éšã®ç¯å²ã§éžå®ããã°ããã The above condensation polymerization may be carried out under the conditions of usually room temperature to 80°C for 48 to 5 hours, and the catalysts used include, for example, titanate esters such as tetrabutyl titanate and tetrapropyl titanate; dibutyltin dilaurate, dibutyl Organotin compounds such as tin maleate, dibutyltin diacetate, tin octylate, tin naphthenate, n-butyltin oxide;
Lead octylate; butylamine, octylamine,
Dibutylamine, monoethanolamine, diethanolamine, triethanolamine, diethylenetriamine, triethylenetetramine, oleylamine, octylamine, cyclohexylamine, benzylamine, diethylaminopropylamine, xylylenediamine, triethylenediamine, guanidine, diphenylguanidine, 2,
4,6-tris(dimethylaminomethyl)phenol, morpholine, N-methylmorpholine, 1,
3-diazabicyclo(5,4,6)undecene-
7 (DBU) or salts of these carboxylic acids, etc.
The species or species are provided for use. The amount used is usually 0.01 to 1 per 100 parts of condensable macromonomer.
The selection can be made within the scope of the department.
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ã©ã¹ç¶çœè²ç²æ«ã®åºäœã§ããã Through such condensation polymerization, for example, in the case of solution polymerization, a viscous solution system is obtained, but when this solution is removed by a normal method, the desired comb-shaped polymer is obtained in the form of a solid at room temperature or a highly viscous oil. Manufactured. The comb-shaped polymer is highly viscous with a low glass transition point when butyl acrylate is used as the vinyl monomer, but in other cases it is mostly a glassy white powder solid.
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ãã The comb-shaped polymer obtained as described above can be efficiently produced by a relatively simple two-step reaction (in some cases, a one-step reaction), and because of its surface migration property, it can be easily produced on the surface or interface by adding a small amount. It is possible to exhibit a modification effect (for example, an anti-fouling effect). Furthermore, those having a functional group of a dialkoxysilane compound [] introduced into the main chain have improved physical properties such as water repellency and adhesion. As described above, the comb-shaped polymer may be used as a water repellent agent for paints, an adhesion agent (particularly for glass surfaces), and a release agent, and may also be used as a surface-active agent.
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ããã Next, the present invention will be described in more detail with reference to Examples.
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ã9.8Ã103ã§ãã€ããExample 1 Methyl methacrylate (MMA) 50g, 3-mercaptopropylmethyldimethoxysilane 0.9
g, AIBN0.08g and toluene 25g are placed in a glass polymerization tube, cooled and degassed, and then melt-sealed. This is 60
Polymerization is carried out with shaking in a â bath, and a highly viscous toluene solution of the condensable macromonomer is obtained after about 8 hours. The yield determined by the weight change method (105°C, 4 hours) was 96%. This macromonomer is IR
It was confirmed by a spectrometer (manufactured by JASCO Corporation) that it was polyMMA. Furthermore, gel permeation chromatography (GPC) revealed that the number average molecular weight was 9.8Ã10 3 .
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ãèªãããããReference Example 1 0.5 part of dibutyltin dilaurate is added to 100 parts of the polyMMA toluene solution of Example 1, spread on a shear plate as thinly as possible, and left at room temperature for 7 days. The toluene as a solvent evaporates and a solid polymer film is obtained. When a part of this was dissolved in tetrahydrofuran and GPC was measured in the same manner as in Example 1, the number average molecular weight was 4.5Ã10 4 . From this, it is recognized that it is a comb-shaped polymer represented by the following formula.
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ããããšãèªããããã Additionally, 2 parts of dimethyldiethoxysilane, 5 parts of ion-exchanged water, and 0.5 parts of n-butyltin oxide were added to 100 parts of the same polyMMA toluene solution, and 8 parts of the solution was heated at 60°C.
The viscosity became higher after stirring for a longer time. of this
GPC measurements revealed that it was a polymer with a molecular weight of 7.8Ã10 4 . From this, it is assumed that organopolysiloxane is the main chain and the average molecular weight is 9.8Ã10 3
It is recognized that it is a comb-shaped polymer with about 8 polyMMA side chains.
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åååéã¯4.5Ã103ã§ãã€ããExample 2 10 g of butyl acrylate and 0.5 g of 3-mercaptopropylmethyldimethoxysilane are placed in a glass polymerization tube, cooled and degassed, and then melt-sealed. This is approx.
Place it in a water tank at 15â and apply UV (Toshiba SHL-100) for 10 minutes.
Photopolymerization is performed while irradiating from a distance of cm. After 10 hours, the contents were taken out and the yield was determined by the weight change method and was found to be 95%. Furthermore, the number average molecular weight was 4.5Ã10 3 as determined by GPC.
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ãŒã§ããããšãèªãããããReference Example 2 To 100 parts of the product of Example 2, 5 parts of methyldimethoxysilane, 0.5 parts of n-butyltin oxide, and a small amount of ion-exchanged water were added, the water was well dispersed, and the mixture was left at 80°C for one day. do. The number average molecular weight of this polymer was measured by GPC and was found to be 3.8Ã10 4 . From this, it is recognized that it is a comb-shaped polymer represented by the following formula.
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åãæããŠããã This comb-shaped polymer has strong adhesion to glass surfaces.
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0.01 g of AIBN is polymerized at 60°C for 8 hours to obtain a condensable macromonomer for the copolymer resin. Then n-
When 0.05 g of butyltin oxide was blended and this was applied onto a glass surface and left for 7 days, the resulting comb-shaped polymer had excellent water repellency and oil repellency.
Claims (1)
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ãªã«åºå«æçž®åæ§ãã¯ãã¢ãããŒã®è£œé æ³ã[Claims] 1 formula, [In the formula, R 5 is hydrogen or a methyl group, and X 1
is an alkyloxycarbonyl group, a substituted alkyloxycarbonyl group, a cycloalkyloxycarbonyl group, or a phenyl group] and consists of 10,000 to 10,000 repeating units of at least one type of [In the formula, R 1 and R 2 are the same or different alkyl groups each having 1 to 4 carbon atoms, and R 3 is -
OR 1 , -OR 2 or an alkyl group having 1 to 4 carbon atoms,
and R 4 is an alkylene group having 1 to 4 carbon atoms]
An alkoxysilyl group-containing condensable macromonomer having a dialkoxysilyl group and H at the other end. 2 formulas, [In the formula, R 1 and R 2 are the same or different alkyl groups each having 1 to 4 carbon atoms, and R 3 is -
OR 1 , -OR 2 or an alkyl group having 1 to 4 carbon atoms,
and R 4 is an alkylene group having 1 to 4 carbon atoms]
At least one mercaptosilane compound represented by the formula, [In the formula, R 5 hydrogen or a methyl group, and X 1 are an alkyloxycarbonyl group, a substituted alkyloxycarbonyl group, a cycloalkyloxycarbonyl group, or a phenyl group] Then, by polymerization in the presence of a radical initiator, the formula: [In the formula, R 5 and X 1 have the same meanings as above] Consisting of 10,000 to 10,000 repeating units of at least one of the following, and CH 2 at one end has the formula, To obtain an alkoxysilyl group-containing condensable macromonomer having a dialkoxysilyl group [wherein R 1 , R 2 , R 3 and R 4 have the same meanings as above] and having H at the other end. A method for producing an alkoxysilyl group-containing condensable macromonomer, characterized by:
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14334185A JPS624706A (en) | 1985-06-29 | 1985-06-29 | Alkoxysilyl group-containing condensible macromonomer |
US07/296,305 US5079298A (en) | 1985-06-11 | 1989-01-09 | Silicon-containing polymer having comb-shape structure |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14334185A JPS624706A (en) | 1985-06-29 | 1985-06-29 | Alkoxysilyl group-containing condensible macromonomer |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS624706A JPS624706A (en) | 1987-01-10 |
JPH0533247B2 true JPH0533247B2 (en) | 1993-05-19 |
Family
ID=15336533
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP14334185A Granted JPS624706A (en) | 1985-06-11 | 1985-06-29 | Alkoxysilyl group-containing condensible macromonomer |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS624706A (en) |
Families Citing this family (2)
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---|---|---|---|---|
DE60232701D1 (en) * | 2001-07-20 | 2009-08-06 | Rohm & Haas | Polymer compound containing silicon ester groups and compositions containing them |
JP2008050620A (en) * | 2007-10-25 | 2008-03-06 | Daikin Ind Ltd | Copolymer for cosmetic |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5978220A (en) * | 1982-10-26 | 1984-05-07 | Sunstar Giken Kk | Room temperature-curable elastic composition |
JPS6088014A (en) * | 1983-09-20 | 1985-05-17 | ã¬ãŒã ã»ã²ãŒã«ã·ã€ããã»ãããã»ãã·ãŠã¬ã³ã¯ãã«ã»ãããã³ã° | Radiation sensitive polymer material and manufacture |
-
1985
- 1985-06-29 JP JP14334185A patent/JPS624706A/en active Granted
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5978220A (en) * | 1982-10-26 | 1984-05-07 | Sunstar Giken Kk | Room temperature-curable elastic composition |
JPS6088014A (en) * | 1983-09-20 | 1985-05-17 | ã¬ãŒã ã»ã²ãŒã«ã·ã€ããã»ãããã»ãã·ãŠã¬ã³ã¯ãã«ã»ãããã³ã° | Radiation sensitive polymer material and manufacture |
Also Published As
Publication number | Publication date |
---|---|
JPS624706A (en) | 1987-01-10 |
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