DE69221222T2 - Propfkopolymere - Google Patents
PropfkopolymereInfo
- Publication number
- DE69221222T2 DE69221222T2 DE69221222T DE69221222T DE69221222T2 DE 69221222 T2 DE69221222 T2 DE 69221222T2 DE 69221222 T DE69221222 T DE 69221222T DE 69221222 T DE69221222 T DE 69221222T DE 69221222 T2 DE69221222 T2 DE 69221222T2
- Authority
- DE
- Germany
- Prior art keywords
- ethylenically unsaturated
- monomer
- macromonomer
- stage
- graft copolymer
- 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
- 229920000578 graft copolymer Polymers 0.000 title claims abstract description 45
- 239000000178 monomer Substances 0.000 claims abstract description 105
- 238000000034 method Methods 0.000 claims abstract description 35
- 229920001577 copolymer Polymers 0.000 claims abstract description 21
- 238000007720 emulsion polymerization reaction Methods 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 23
- 239000002245 particle Substances 0.000 claims description 21
- 238000006116 polymerization reaction Methods 0.000 claims description 21
- 229920000642 polymer Polymers 0.000 claims description 19
- 239000006185 dispersion Substances 0.000 claims description 15
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-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 14
- -1 vinyl aromatic compounds Chemical class 0.000 claims description 13
- 125000000391 vinyl group Chemical class [H]C([*])=C([H])[H] 0.000 claims description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 12
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 10
- 229920002554 vinyl polymer Polymers 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 9
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 3
- 230000001070 adhesive effect Effects 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
- 101100097467 Arabidopsis thaliana SYD gene Proteins 0.000 claims description 2
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-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
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- 101100495925 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr3 gene Proteins 0.000 claims description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-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
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001721 carbon Chemical class 0.000 claims description 2
- 239000013521 mastic Substances 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
- 150000003460 sulfonic acids Chemical class 0.000 claims description 2
- 229920001567 vinyl ester resin Chemical class 0.000 claims description 2
- 239000006069 physical mixture Substances 0.000 claims 1
- 239000000565 sealant Substances 0.000 claims 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 71
- 239000000839 emulsion Substances 0.000 description 51
- 239000000243 solution Substances 0.000 description 31
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 30
- 238000007792 addition Methods 0.000 description 24
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 20
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical group CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 239000004094 surface-active agent Substances 0.000 description 16
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000003999 initiator Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000007795 chemical reaction product Substances 0.000 description 10
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 10
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000001632 sodium acetate Substances 0.000 description 8
- 235000017281 sodium acetate Nutrition 0.000 description 8
- 239000012986 chain transfer agent Substances 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 6
- 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 6
- 239000003960 organic solvent Substances 0.000 description 6
- 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 5
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical group CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-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
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 5
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 5
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 5
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 5
- 229940001584 sodium metabisulfite Drugs 0.000 description 5
- 235000010262 sodium metabisulphite Nutrition 0.000 description 5
- XMRUJYGYYCLRGJ-UHFFFAOYSA-N azanium;2-[2-[2-[2-(4-nonylphenoxy)ethoxy]ethoxy]ethoxy]ethyl sulfate Chemical compound [NH4+].CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOS([O-])(=O)=O)C=C1 XMRUJYGYYCLRGJ-UHFFFAOYSA-N 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- NFJNJCYJOUZNSO-UHFFFAOYSA-M sodium;ethenyl sulfate Chemical compound [Na+].[O-]S(=O)(=O)OC=C NFJNJCYJOUZNSO-UHFFFAOYSA-M 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 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
- 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
- 239000003054 catalyst Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- 238000004519 manufacturing process Methods 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
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229940083542 sodium Drugs 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
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 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
- 239000004908 Emulsion polymer Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 238000012662 bulk polymerization Methods 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
- 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
- 235000010350 erythorbic acid Nutrition 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229940026239 isoascorbic acid Drugs 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000004597 plastic additive Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000007789 sealing Methods 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
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 125000002348 vinylic group Chemical group 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Polymerisation Methods In General (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Paints Or Removers (AREA)
- Organic Insulating Materials (AREA)
- Materials For Medical Uses (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Liquid Crystal Substances (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (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 (2)
| Publication Number | Publication Date |
|---|---|
| DE69221222D1 DE69221222D1 (de) | 1997-09-04 |
| DE69221222T2 true DE69221222T2 (de) | 1998-02-12 |
Family
ID=24902378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69221222T Expired - Fee Related DE69221222T2 (de) | 1991-06-27 | 1992-06-16 | Propfkopolymere |
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) | FI922971L (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 |
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| CA572522A (en) * | 1959-03-17 | Canadian Industries Limited | Block and graft copolymerization with polymers containing mercapto groups | |
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-
1991
- 1991-06-27 US US07/722,562 patent/US5247040A/en not_active Expired - Fee Related
-
1992
- 1992-06-16 EP EP92305506A patent/EP0520668B1/en not_active Expired - Lifetime
- 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
- 1992-06-17 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 TR TR92/0607A patent/TR26079A/xx unknown
- 1992-06-24 IL IL102291A patent/IL102291A0/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 JP JP16963692A patent/JP3549902B2/ja not_active Expired - Fee Related
- 1992-06-26 FI FI922971A patent/FI922971L/fi not_active Application Discontinuation
- 1992-06-26 CZ CS921994A patent/CZ199492A3/cs unknown
- 1992-06-26 CN CN92105155A patent/CN1068124A/zh active Pending
- 1992-06-26 KR KR1019920011266A patent/KR930000555A/ko not_active Withdrawn
- 1992-06-26 HU HU9202136A patent/HU9202136D0/hu unknown
- 1992-06-26 PL PL29505292A patent/PL295052A1/xx 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 |
|---|---|
| MX9203302A (es) | 1992-12-01 |
| TW200497B (enExample) | 1993-02-21 |
| US5247040A (en) | 1993-09-21 |
| EP0520668A1 (en) | 1992-12-30 |
| AU657542B2 (en) | 1995-03-16 |
| EP0520668B1 (en) | 1997-07-30 |
| US5314977A (en) | 1994-05-24 |
| ZA924518B (en) | 1993-03-31 |
| FI922971A0 (fi) | 1992-06-26 |
| IE922116A1 (en) | 1992-12-30 |
| IL102291A0 (en) | 1993-01-14 |
| CA2071401A1 (en) | 1992-12-28 |
| FI922971A7 (fi) | 1992-12-28 |
| BR9202400A (pt) | 1993-01-26 |
| HU9202136D0 (en) | 1992-10-28 |
| NO922472D0 (no) | 1992-06-23 |
| CN1068124A (zh) | 1993-01-20 |
| JP3549902B2 (ja) | 2004-08-04 |
| KR930000555A (ko) | 1993-01-15 |
| CZ199492A3 (en) | 1993-01-13 |
| FI922971L (fi) | 1992-12-28 |
| JPH05186542A (ja) | 1993-07-27 |
| NO922472L (no) | 1992-12-28 |
| TR26079A (tr) | 1994-12-15 |
| HK1000304A1 (en) | 1998-02-20 |
| PL295052A1 (en) | 1993-05-31 |
| DE69221222D1 (de) | 1997-09-04 |
| CA2071401C (en) | 2004-06-15 |
| ATE156138T1 (de) | 1997-08-15 |
| AU1827492A (en) | 1993-01-07 |
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