CZ199492A3 - Graft copolymers and process for preparing thereof - Google Patents
Graft copolymers and process for preparing thereof Download PDFInfo
- Publication number
- CZ199492A3 CZ199492A3 CS921994A CS199492A CZ199492A3 CZ 199492 A3 CZ199492 A3 CZ 199492A3 CS 921994 A CS921994 A CS 921994A CS 199492 A CS199492 A CS 199492A CZ 199492 A3 CZ199492 A3 CZ 199492A3
- Authority
- CZ
- Czechia
- Prior art keywords
- monomer
- vinyl
- macromonomer
- water
- ethylenically unsaturated
- Prior art date
Links
- 229920000578 graft copolymer Polymers 0.000 title claims abstract description 36
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000000178 monomer Substances 0.000 claims abstract description 97
- 238000000034 method Methods 0.000 claims abstract description 44
- 230000008569 process Effects 0.000 claims abstract description 26
- 229920001577 copolymer Polymers 0.000 claims abstract description 19
- 238000007720 emulsion polymerization reaction Methods 0.000 claims abstract description 15
- 125000000391 vinyl group Chemical class [H]C([*])=C([H])[H] 0.000 claims description 15
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 14
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 11
- -1 styrene Chemical class 0.000 claims description 11
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 6
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 4
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 4
- 229920001567 vinyl ester resin Chemical class 0.000 claims description 3
- IAUGBVWVWDTCJV-UHFFFAOYSA-N 1-(prop-2-enoylamino)propane-1-sulfonic acid Chemical compound CCC(S(O)(=O)=O)NC(=O)C=C IAUGBVWVWDTCJV-UHFFFAOYSA-N 0.000 claims description 2
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical class C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 claims description 2
- PRAMZQXXPOLCIY-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical compound CC(=C)C(=O)OCCS(O)(=O)=O PRAMZQXXPOLCIY-UHFFFAOYSA-N 0.000 claims description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 claims description 2
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 claims description 2
- GQTFHSAAODFMHB-UHFFFAOYSA-N 2-prop-2-enoyloxyethanesulfonic acid Chemical compound OS(=O)(=O)CCOC(=O)C=C GQTFHSAAODFMHB-UHFFFAOYSA-N 0.000 claims description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical class C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 2
- 150000003926 acrylamides Chemical class 0.000 claims description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000003440 styrenes Chemical class 0.000 claims description 2
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims 1
- 150000003460 sulfonic acids Chemical class 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 68
- 239000000839 emulsion Substances 0.000 description 47
- 239000000243 solution Substances 0.000 description 28
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 27
- 239000002245 particle Substances 0.000 description 20
- 229920000642 polymer Polymers 0.000 description 19
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 18
- 238000006116 polymerization reaction Methods 0.000 description 18
- 239000007787 solid Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000006185 dispersion Substances 0.000 description 12
- 239000004094 surface-active agent Substances 0.000 description 12
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 11
- 239000004793 Polystyrene Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 9
- 229920002554 vinyl polymer Polymers 0.000 description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- 239000012986 chain transfer agent Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 229940083542 sodium Drugs 0.000 description 7
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 7
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000001632 sodium acetate Substances 0.000 description 6
- 235000017281 sodium acetate Nutrition 0.000 description 6
- PMNLUUOXGOOLSP-UHFFFAOYSA-M 2-sulfanylpropanoate Chemical compound CC(S)C([O-])=O PMNLUUOXGOOLSP-UHFFFAOYSA-M 0.000 description 5
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 5
- 238000011010 flushing procedure Methods 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 230000000977 initiatory effect Effects 0.000 description 4
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 4
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 4
- 235000010262 sodium metabisulphite Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004945 emulsification Methods 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 229940001584 sodium metabisulfite Drugs 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 235000004431 Linum usitatissimum Nutrition 0.000 description 2
- 240000006240 Linum usitatissimum Species 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 235000019395 ammonium persulphate Nutrition 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 235000004426 flaxseed Nutrition 0.000 description 2
- 229920002959 polymer blend Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- DAFHKNAQFPVRKR-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)C DAFHKNAQFPVRKR-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004160 Ammonium persulphate Substances 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 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
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-isoascorbic acid Chemical compound OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-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
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 238000012662 bulk polymerization Methods 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
- 150000001721 carbon Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 206010013023 diphtheria Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000010556 emulsion polymerization method Methods 0.000 description 1
- 235000010350 erythorbic acid Nutrition 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229940017705 formaldehyde sulfoxylate Drugs 0.000 description 1
- ISXSFOPKZQZDAO-UHFFFAOYSA-N formaldehyde;sodium Chemical compound [Na].O=C ISXSFOPKZQZDAO-UHFFFAOYSA-N 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- SBGKURINHGJRFN-UHFFFAOYSA-N hydroxymethanesulfinic acid Chemical compound OCS(O)=O SBGKURINHGJRFN-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229940026239 isoascorbic acid Drugs 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000004597 plastic additive Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 235000019394 potassium persulphate Nutrition 0.000 description 1
- 239000008237 rinsing water Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229940001607 sodium bisulfite Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000001433 sodium tartrate Substances 0.000 description 1
- 229960002167 sodium tartrate Drugs 0.000 description 1
- 235000011004 sodium tartrates Nutrition 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- RVUXIPACAZKWHU-UHFFFAOYSA-N sulfuric acid;heptahydrate Chemical compound O.O.O.O.O.O.O.OS(O)(=O)=O RVUXIPACAZKWHU-UHFFFAOYSA-N 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000002604 ultrasonography Methods 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
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/04—Polymers provided for in subclasses C08C or C08F
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/04—Polymers provided for in subclasses C08C or C08F
- C08F290/046—Polymers of unsaturated carboxylic acids or derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Graft Or Block Polymers (AREA)
- Polymerisation Methods In General (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Organic Insulating Materials (AREA)
- Materials For Medical Uses (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/722,562 US5247040A (en) | 1991-06-27 | 1991-06-27 | Graft copolymers prepared by two staged aqueous emulsion polymerization |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CZ199492A3 true CZ199492A3 (en) | 1993-01-13 |
Family
ID=24902378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS921994A CZ199492A3 (en) | 1991-06-27 | 1992-06-26 | Graft copolymers and process for preparing thereof |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US5247040A (enExample) |
| EP (1) | EP0520668B1 (enExample) |
| JP (1) | JP3549902B2 (enExample) |
| KR (1) | KR930000555A (enExample) |
| CN (1) | CN1068124A (enExample) |
| AT (1) | ATE156138T1 (enExample) |
| AU (1) | AU657542B2 (enExample) |
| BR (1) | BR9202400A (enExample) |
| CA (1) | CA2071401C (enExample) |
| CZ (1) | CZ199492A3 (enExample) |
| DE (1) | DE69221222T2 (enExample) |
| FI (1) | FI922971A7 (enExample) |
| HK (1) | HK1000304A1 (enExample) |
| HU (1) | HU9202136D0 (enExample) |
| IE (1) | IE922116A1 (enExample) |
| IL (1) | IL102291A0 (enExample) |
| MX (1) | MX9203302A (enExample) |
| NO (1) | NO922472L (enExample) |
| PL (1) | PL295052A1 (enExample) |
| TR (1) | TR26079A (enExample) |
| TW (1) | TW200497B (enExample) |
| ZA (1) | ZA924518B (enExample) |
Families Citing this family (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5306744A (en) * | 1992-12-18 | 1994-04-26 | Rohm And Haas Company | Functionalized multistage polymers |
| DE4244386A1 (de) * | 1992-12-29 | 1994-06-30 | Basf Ag | Vinylpyrrolidon- und Vinylimidazol-Copolymerisate, Verfahren zur ihrer Herstellung und ihre Verwendung in Waschmitteln |
| TW325482B (en) * | 1994-01-31 | 1998-01-21 | Himont Inc | A process for sequentially grafting olefin polymer materials and grafted polymer therefrom |
| CA2188552A1 (en) * | 1994-05-19 | 1995-11-30 | Jozef Huybrechts | Coatings comprising self-stabilized lattices prepared in an aqueous carrier |
| FR2720751B1 (fr) * | 1994-06-03 | 1996-07-19 | Rhone Poulenc Chimie | Copolymère polyoléfinique greffe. |
| US5700873A (en) * | 1995-03-07 | 1997-12-23 | Adhesives Research, Inc. | Method of preparation of water-soluble copolymer |
| DE19524053A1 (de) * | 1995-07-01 | 1997-01-02 | Roehm Gmbh | Verfahren zur Herstellung von verzweigten Polymerisaten |
| US6028155A (en) * | 1997-05-21 | 2000-02-22 | Eastman Chemical Company | Surfactant-containing acetoacetoxy-functional and enamine-functional polymers |
| US5891950A (en) * | 1996-05-28 | 1999-04-06 | Eastman Chemical Company | Use of stable amino-functional latexes in water-based inks |
| US5998543A (en) * | 1996-05-28 | 1999-12-07 | Eastman Chemical Company | Stable amino-containing polymer latex blends |
| US6417267B1 (en) | 1996-05-28 | 2002-07-09 | Eastman Chemical Company | Adhesive compositions containing stable amino-containing polymer latex blends |
| US5962556A (en) * | 1996-10-22 | 1999-10-05 | Eastman Chemical Company | Functional latexes resistant to hydrolysis |
| US5782972A (en) * | 1997-03-21 | 1998-07-21 | W.R. Grace & Co.-Conn. | Additive for production of highly workable mortar cement |
| BR9809152A (pt) * | 1997-05-21 | 2000-08-01 | Eastman Chem Co | Processo para preparação de misturas de látex reativo que são quimicamente e fisicamente estáveis até a formação de pelìcula |
| US6649679B1 (en) | 1997-09-18 | 2003-11-18 | Eastman Chemical Company | Stable waterborne polymer compositions containing poly(alkylenimines) |
| KR100387311B1 (ko) * | 1997-12-26 | 2003-08-21 | 제일모직주식회사 | 분지구조를갖는스티렌계열가소성수지및그제조방법 |
| US6391992B1 (en) * | 1998-09-18 | 2002-05-21 | Celanese International Corporation | Sulfonate-terminated oligomers of vinyl esters and their vinyl alcohol oligomer derivatives |
| DE69943379D1 (de) | 1998-11-23 | 2011-06-01 | Grace W R & Co | Verbesserte verarbeitung und lebensdauer von mörtelplatten aus maurermörtel und verfahren zu dessen herstellung |
| EP1211269B1 (en) * | 1999-05-07 | 2009-08-26 | Sekisui Chemical Co., Ltd. | Acrylic copolymer, acrylic pressure-sensitive adhesive composition, acrylic pressure-sensitive adhesive tape or sheet, and acrylic adhesive composition |
| US6462109B1 (en) | 1999-10-12 | 2002-10-08 | Eastman Chemical Company | Surfactantless latex compositions and methods of making polymer blends using these compositions |
| US6410005B1 (en) | 2000-06-15 | 2002-06-25 | Pmd Holdings Corp. | Branched/block copolymers for treatment of keratinous substrates |
| AU2001290978A1 (en) | 2000-09-14 | 2002-03-26 | Rohm And Haas Company | Adhesive compositions containing low molecular weight polymeric additives |
| US6670419B2 (en) | 2000-09-14 | 2003-12-30 | Rohm And Haas Company | Method of toughening thermoplastic polymers and thermoplastic compositions produced thereby |
| DE60131992T2 (de) * | 2000-09-14 | 2008-12-18 | Rohm And Haas Co. | Pfropfcopolymere enthaltende klebstoffe |
| US20040024144A1 (en) * | 2000-09-14 | 2004-02-05 | Robert Solomon | Aqueous dispersions of comb copolymers and coatings produced therefrom |
| DE60135668D1 (de) | 2000-09-14 | 2008-10-16 | Rohm & Haas | Aus segmenten bestehende polymere und wässrige dispersionen und filme davon |
| US20090005476A1 (en) * | 2001-04-09 | 2009-01-01 | Eastman Chemical Company | Polyol latex compositions and process of making them |
| US6844390B2 (en) * | 2001-04-09 | 2005-01-18 | Eastman Chemical Company | Modified alkyd compositions comprising polyol latex compositions and processes of making them |
| US6699931B2 (en) | 2001-04-09 | 2004-03-02 | Eastman Chemical Company | Modified alkyd compositions comprising diol latex compositions and processes of making the same |
| JP4643895B2 (ja) | 2002-06-28 | 2011-03-02 | 株式会社カネカ | ペースト用塩化ビニル系共重合樹脂、組成物及び樹脂の製造方法 |
| US7189780B2 (en) * | 2003-08-12 | 2007-03-13 | Hexion Specialty Chemicals, Inc. | Processes to produce water-dispersible polyester stabilized, acid-treated, fluoroalkyl compositions |
| US7101924B2 (en) * | 2003-08-12 | 2006-09-05 | Hexion Specialty Materials, Inc. | Water-dispersible polyester stabilized, acid-treated, fluoroalkyl compositions |
| US7173081B2 (en) * | 2003-08-12 | 2007-02-06 | Hexion Specialty Chemicals, Inc. | Processes to produce water-dispersible polyester stabilized fluoroalkyl compositions |
| US7186769B2 (en) * | 2003-08-12 | 2007-03-06 | Hexion Specialty Chemicals, Inc. | Water-dispersible polyester stabilized fluoroalkyl compositions |
| JP2005281570A (ja) * | 2004-03-30 | 2005-10-13 | Kaneka Corp | 射出成形品用塩化ビニル系樹脂組成物 |
| JP2005281567A (ja) * | 2004-03-30 | 2005-10-13 | Kaneka Corp | カレンダー加工用塩化ビニル系樹脂組成物 |
| JP2005281571A (ja) * | 2004-03-30 | 2005-10-13 | Kaneka Corp | 押出加工用硬質塩化ビニル系樹脂組成物 |
| JP2005281569A (ja) * | 2004-03-30 | 2005-10-13 | Kaneka Corp | 塩化ビニル系樹脂組成物 |
| EP1894950A1 (en) | 2006-08-31 | 2008-03-05 | Rohm and Haas France SAS | Aqueous dispersion of polymeric particles |
| EP1894951B1 (en) | 2006-08-31 | 2018-11-28 | Rohm and Haas Company | Aqueous dispersion of polymeric particles |
| US9034964B2 (en) | 2010-10-21 | 2015-05-19 | Eastman Chemical Company | Waterborne coating compositions containing low-VOC coalescents that are hydroxypivalyl hydroxypivalate esters |
| US8383710B2 (en) | 2010-10-21 | 2013-02-26 | Eastman Chemical Company | Waterborne coating compositions containing low-VOC coalescents |
| US9029451B2 (en) | 2010-12-15 | 2015-05-12 | Eastman Chemical Company | Waterborne coating compositions that include 2,2,4-trimethyl-3-oxopentanoate esters as reactive coalescents |
| US8809446B2 (en) | 2010-12-15 | 2014-08-19 | Eastman Chemical Company | Substituted 3-oxopentanoates and their uses in coating compositions |
| US8809447B2 (en) | 2010-12-15 | 2014-08-19 | Eastman Chemical Company | Acetoacetate-functional monomers and their uses in coating compositions |
| EP2607102B1 (en) * | 2011-12-21 | 2016-09-14 | The Goodyear Tire & Rubber Company | Method of making a graft polymer, copolymer and tire |
| US9156932B2 (en) | 2011-12-21 | 2015-10-13 | The Goodyear Tire & Rubber Company | Method of making a graft copolymer |
| US8759451B2 (en) * | 2011-12-21 | 2014-06-24 | The Goodyear Tire & Rubber Company | Method of making a graft copolymer |
| US9040619B2 (en) | 2012-11-08 | 2015-05-26 | Eastman Chemical Company | 1,3-diketoamide functional polymers and compositions employing the same |
| JP6541952B2 (ja) * | 2014-09-26 | 2019-07-10 | 株式会社日本触媒 | マクロモノマー及びその製造方法 |
| US10889536B1 (en) | 2019-09-04 | 2021-01-12 | Eastman Chemical Company | Enol ethers |
| US10550057B1 (en) | 2019-09-04 | 2020-02-04 | Eastman Chemical Company | Method of making a dialdeyhde |
| US11518899B2 (en) | 2019-09-04 | 2022-12-06 | Eastman Chemical Company | Aromatic enol ether paint additives |
| US20210062017A1 (en) | 2019-09-04 | 2021-03-04 | Eastman Chemical Company | Branched acetal coalescing aids |
| US10858304B1 (en) | 2019-09-04 | 2020-12-08 | Eastman Chemical Company | Aromatic enol ethers |
| US10865172B1 (en) | 2019-09-04 | 2020-12-15 | Eastman Chemical Company | Aromatic enol ethers |
| US10544076B1 (en) | 2019-09-04 | 2020-01-28 | Eastman Chemical Company | Method of making a dialdeyhde |
| US10865171B1 (en) | 2019-09-04 | 2020-12-15 | Eastman Chemical Company | Process to make aromatic enol ethers and olefin isomers of aromatic enol ethers |
| US11312873B2 (en) | 2019-09-04 | 2022-04-26 | Eastman Chemical Company | Aromatic enol ether paint additives |
| US10815179B1 (en) | 2019-09-04 | 2020-10-27 | Eastman Chemical Company | Aromatic dicarbinols |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA572522A (en) * | 1959-03-17 | Canadian Industries Limited | Block and graft copolymerization with polymers containing mercapto groups | |
| GB1096912A (en) * | 1963-08-06 | 1967-12-29 | Ici Ltd | Synthetic polymers |
| US3503940A (en) * | 1966-11-15 | 1970-03-31 | Exxon Research Engineering Co | Polymerization of unsaturated mercaptans to polythioethers |
| US3862102A (en) * | 1971-02-22 | 1975-01-21 | Cpc International Inc | Alpha-olefin terminated polydiene macromolecular monomers having a substantially uniform molecular weight distribution |
| US5028677A (en) * | 1986-09-23 | 1991-07-02 | E. I. Du Pont De Nemours And Company | Novel macromonomer compositions |
| JP2677994B2 (ja) * | 1986-10-06 | 1997-11-17 | 株式会社クラレ | 接着剤 |
| JPS6448202A (en) * | 1987-08-18 | 1989-02-22 | Mitsubishi Electric Corp | Magnetic tape recording and reproducing device |
| JP2662800B2 (ja) * | 1987-09-07 | 1997-10-15 | 三菱電機株式会社 | 半導体記憶装置 |
| US4937297A (en) * | 1988-05-02 | 1990-06-26 | Amoco Corporation | Polyarylate-polyamide block copolymers |
| JPH01289293A (ja) * | 1988-05-17 | 1989-11-21 | Fujitsu Ltd | プリント回路基板の製造方法 |
| JPH0645697B2 (ja) * | 1988-06-02 | 1994-06-15 | 昭和高分子株式会社 | 硬化可能な樹脂組成物 |
-
1991
- 1991-06-27 US US07/722,562 patent/US5247040A/en not_active Expired - Fee Related
-
1992
- 1992-06-16 DE DE69221222T patent/DE69221222T2/de not_active Expired - Fee Related
- 1992-06-16 AT AT92305506T patent/ATE156138T1/de not_active IP Right Cessation
- 1992-06-16 EP EP92305506A patent/EP0520668B1/en not_active Expired - Lifetime
- 1992-06-17 CA CA002071401A patent/CA2071401C/en not_active Expired - Fee Related
- 1992-06-17 AU AU18274/92A patent/AU657542B2/en not_active Ceased
- 1992-06-19 ZA ZA924518A patent/ZA924518B/xx unknown
- 1992-06-23 NO NO92922472A patent/NO922472L/no unknown
- 1992-06-24 IL IL102291A patent/IL102291A0/xx unknown
- 1992-06-24 TR TR92/0607A patent/TR26079A/xx unknown
- 1992-06-25 BR BR929202400A patent/BR9202400A/pt not_active IP Right Cessation
- 1992-06-25 MX MX9203302A patent/MX9203302A/es not_active IP Right Cessation
- 1992-06-26 CN CN92105155A patent/CN1068124A/zh active Pending
- 1992-06-26 KR KR1019920011266A patent/KR930000555A/ko not_active Withdrawn
- 1992-06-26 FI FI922971A patent/FI922971A7/fi not_active Application Discontinuation
- 1992-06-26 HU HU9202136A patent/HU9202136D0/hu unknown
- 1992-06-26 PL PL29505292A patent/PL295052A1/xx unknown
- 1992-06-26 JP JP16963692A patent/JP3549902B2/ja not_active Expired - Fee Related
- 1992-06-26 CZ CS921994A patent/CZ199492A3/cs unknown
- 1992-07-01 IE IE211692A patent/IE922116A1/en not_active Application Discontinuation
- 1992-08-07 TW TW081106246A patent/TW200497B/zh active
-
1993
- 1993-06-03 US US08/071,902 patent/US5314977A/en not_active Expired - Fee Related
-
1997
- 1997-09-25 HK HK97101836A patent/HK1000304A1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR930000555A (ko) | 1993-01-15 |
| FI922971A0 (fi) | 1992-06-26 |
| TW200497B (enExample) | 1993-02-21 |
| TR26079A (tr) | 1994-12-15 |
| IL102291A0 (en) | 1993-01-14 |
| JP3549902B2 (ja) | 2004-08-04 |
| BR9202400A (pt) | 1993-01-26 |
| HK1000304A1 (en) | 1998-02-20 |
| CN1068124A (zh) | 1993-01-20 |
| FI922971L (fi) | 1992-12-28 |
| EP0520668A1 (en) | 1992-12-30 |
| CA2071401C (en) | 2004-06-15 |
| US5314977A (en) | 1994-05-24 |
| NO922472L (no) | 1992-12-28 |
| AU1827492A (en) | 1993-01-07 |
| IE922116A1 (en) | 1992-12-30 |
| NO922472D0 (no) | 1992-06-23 |
| PL295052A1 (en) | 1993-05-31 |
| DE69221222T2 (de) | 1998-02-12 |
| DE69221222D1 (de) | 1997-09-04 |
| AU657542B2 (en) | 1995-03-16 |
| ATE156138T1 (de) | 1997-08-15 |
| JPH05186542A (ja) | 1993-07-27 |
| HU9202136D0 (en) | 1992-10-28 |
| CA2071401A1 (en) | 1992-12-28 |
| FI922971A7 (fi) | 1992-12-28 |
| EP0520668B1 (en) | 1997-07-30 |
| MX9203302A (es) | 1992-12-01 |
| ZA924518B (en) | 1993-03-31 |
| US5247040A (en) | 1993-09-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CZ199492A3 (en) | Graft copolymers and process for preparing thereof | |
| HK1000304B (en) | Graft copolymers | |
| US4876313A (en) | Grafted core-shell polymer compositions using polyfunctional compounds | |
| KR0149877B1 (ko) | 재분산 가능한 코어-셸 폴리머 분말의 제조방법 | |
| FI95585B (fi) | Polymeeripartikkelit ja niiden valmistaminen | |
| EP0176609A1 (en) | Process for preparing latexes of polymers having pendant coreactive and oxazoline groups | |
| EP0338486A2 (en) | Stable emulsion polymers and methods of preparing same | |
| US5399621A (en) | Process for the preparation of a graft copolymer latex of core/shell dispersion particles having improved phase binding between core and shell | |
| EP0279572A2 (en) | High gloss acrylate rubber-modified weatherable resins and preparation thereof | |
| MXPA04012445A (es) | Polimeros de revestimiento-nucleo que tienen revestimientos hidrofilicos para proteccion de revestimiento mejorada y propiedades anti bloqueo. | |
| JPH07216025A (ja) | アルカリ可溶性エマルジョンコポリマーの製造方法 | |
| US4703090A (en) | Method for the preparation of graft copolymers by emulsion copolymerization | |
| JPH05247148A (ja) | メタクリレート‐ブタジエン‐スチレングラフトポリマー、ならびに低い黄色度、良好な透明度および向上した衝撃強さを有する前記グラフトポリマーとｐｖｃのブレンド | |
| JPH08253538A (ja) | グラフトポリマー組成物 | |
| JPH06313018A (ja) | エラストマー性の粒状グラフト重合体の製法 | |
| US5340874A (en) | Modified polyvinyl alcohol and a solid state process for modification of polyvinyl alcohol by free radical grafting | |
| JPH0651733B2 (ja) | 樹脂強化乳化重合体の製造方法 | |
| JP2002514231A (ja) | 耐加水分解性官能性ラテックス | |
| US5605972A (en) | Graft and core-shell copolymers having improved phase bonding between graft substrate and grafted-on polymer phase | |
| CS212792B2 (cs) | Termoplastický materiál a způsob jeho výroby | |
| JPH0449841B2 (enExample) | ||
| JP2986909B2 (ja) | 安定な乳化重合体及びその製法 | |
| JP2021531368A (ja) | シリコーンモノマー及びアクリルモノマーの重合プロセス | |
| JPS6348884B2 (enExample) | ||
| JPH044323B2 (enExample) |