CA2408787C - Latex formulations with reduced yellowing - Google Patents
Latex formulations with reduced yellowing Download PDFInfo
- Publication number
- CA2408787C CA2408787C CA002408787A CA2408787A CA2408787C CA 2408787 C CA2408787 C CA 2408787C CA 002408787 A CA002408787 A CA 002408787A CA 2408787 A CA2408787 A CA 2408787A CA 2408787 C CA2408787 C CA 2408787C
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- diaminohexane
- group
- combinations
- exhibits reduced
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 248
- 239000004816 latex Substances 0.000 title claims abstract description 245
- 229920000126 latex Polymers 0.000 title claims abstract description 244
- 238000009472 formulation Methods 0.000 title claims abstract description 152
- 238000004383 yellowing Methods 0.000 title claims abstract description 129
- 150000001412 amines Chemical class 0.000 claims abstract description 60
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 26
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 15
- 239000000178 monomer Substances 0.000 claims description 378
- 229920000642 polymer Polymers 0.000 claims description 142
- -1 alkyl methacrylates Chemical class 0.000 claims description 91
- 229910001868 water Inorganic materials 0.000 claims description 83
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 82
- 239000002245 particle Substances 0.000 claims description 79
- 125000004432 carbon atom Chemical group C* 0.000 claims description 76
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 63
- 239000000908 ammonium hydroxide Substances 0.000 claims description 63
- 229920002554 vinyl polymer Polymers 0.000 claims description 61
- 229910052799 carbon Inorganic materials 0.000 claims description 56
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 49
- 125000003277 amino group Chemical group 0.000 claims description 48
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 43
- IBDVWXAVKPRHCU-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 3-oxobutanoate Chemical group CC(=O)CC(=O)OCCOC(=O)C(C)=C IBDVWXAVKPRHCU-UHFFFAOYSA-N 0.000 claims description 35
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 30
- 239000004094 surface-active agent Substances 0.000 claims description 29
- 150000002148 esters Chemical class 0.000 claims description 28
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 23
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 21
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 21
- WTSXICLFTPPDTL-UHFFFAOYSA-N pentane-1,3-diamine Chemical compound CCC(N)CCN WTSXICLFTPPDTL-UHFFFAOYSA-N 0.000 claims description 17
- 229910021529 ammonia Inorganic materials 0.000 claims description 15
- 238000006116 polymerization reaction Methods 0.000 claims description 15
- 150000004985 diamines Chemical class 0.000 claims description 14
- 230000000379 polymerizing effect Effects 0.000 claims description 14
- 239000007870 radical polymerization initiator Substances 0.000 claims description 14
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 13
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 12
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 11
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 11
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical group [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 claims description 9
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims description 9
- QSMCLIWFRATFMT-UHFFFAOYSA-N 2-methylhexane-1,4-diamine Chemical compound CCC(N)CC(C)CN QSMCLIWFRATFMT-UHFFFAOYSA-N 0.000 claims description 8
- VQGRILOLJITFOR-UHFFFAOYSA-N 2-methylhexane-1,5-diamine Chemical compound CC(N)CCC(C)CN VQGRILOLJITFOR-UHFFFAOYSA-N 0.000 claims description 8
- PGXBLKMCNUKABP-UHFFFAOYSA-N 2-methylpentane-1,3-diamine Chemical compound CCC(N)C(C)CN PGXBLKMCNUKABP-UHFFFAOYSA-N 0.000 claims description 8
- ACEKLXGWCBIDGA-UHFFFAOYSA-N 2-methylpentane-1,4-diamine Chemical compound CC(N)CC(C)CN ACEKLXGWCBIDGA-UHFFFAOYSA-N 0.000 claims description 8
- BWVXSUHAWILBTN-UHFFFAOYSA-N 3-methylhexane-1,3-diamine Chemical compound CCCC(C)(N)CCN BWVXSUHAWILBTN-UHFFFAOYSA-N 0.000 claims description 8
- LZEHBXAZHLVXLW-UHFFFAOYSA-N 3-methylhexane-1,4-diamine Chemical compound CCC(N)C(C)CCN LZEHBXAZHLVXLW-UHFFFAOYSA-N 0.000 claims description 8
- OLTBRQIRRDQOTO-UHFFFAOYSA-N 3-methylpentane-1,4-diamine Chemical compound CC(N)C(C)CCN OLTBRQIRRDQOTO-UHFFFAOYSA-N 0.000 claims description 8
- HKTQMCDAQDHXDJ-UHFFFAOYSA-N 4-methylhexane-1,3-diamine Chemical compound CCC(C)C(N)CCN HKTQMCDAQDHXDJ-UHFFFAOYSA-N 0.000 claims description 8
- NYCNZFKSGAOSCE-UHFFFAOYSA-N 4-methylhexane-1,5-diamine Chemical compound CC(N)C(C)CCCN NYCNZFKSGAOSCE-UHFFFAOYSA-N 0.000 claims description 8
- FAKVQKOINPDRTH-UHFFFAOYSA-N 4-methylpentane-1,3-diamine Chemical compound CC(C)C(N)CCN FAKVQKOINPDRTH-UHFFFAOYSA-N 0.000 claims description 8
- XJMFFJYZSJMGGP-UHFFFAOYSA-N 5-methylhexane-1,4-diamine Chemical compound CC(C)C(N)CCCN XJMFFJYZSJMGGP-UHFFFAOYSA-N 0.000 claims description 8
- ULEAQRIQMIQDPJ-UHFFFAOYSA-N butane-1,2-diamine Chemical compound CCC(N)CN ULEAQRIQMIQDPJ-UHFFFAOYSA-N 0.000 claims description 8
- RGTXVXDNHPWPHH-UHFFFAOYSA-N butane-1,3-diamine Chemical compound CC(N)CCN RGTXVXDNHPWPHH-UHFFFAOYSA-N 0.000 claims description 8
- DNDUSOASNMMTNN-UHFFFAOYSA-N heptane-1,3-diamine Chemical compound CCCCC(N)CCN DNDUSOASNMMTNN-UHFFFAOYSA-N 0.000 claims description 8
- APWFJLJAQRZQIV-UHFFFAOYSA-N heptane-1,4-diamine Chemical compound CCCC(N)CCCN APWFJLJAQRZQIV-UHFFFAOYSA-N 0.000 claims description 8
- ZOMZNNQGMGBLHO-UHFFFAOYSA-N heptane-1,5-diamine Chemical compound CCC(N)CCCCN ZOMZNNQGMGBLHO-UHFFFAOYSA-N 0.000 claims description 8
- HYQBVSXBLGKEDT-UHFFFAOYSA-N hexane-1,4-diamine Chemical compound CCC(N)CCCN HYQBVSXBLGKEDT-UHFFFAOYSA-N 0.000 claims description 8
- XTBMQKZEIICCCS-UHFFFAOYSA-N hexane-1,5-diamine Chemical compound CC(N)CCCCN XTBMQKZEIICCCS-UHFFFAOYSA-N 0.000 claims description 8
- HZJYYGGZHQIQKL-UHFFFAOYSA-N hexane-2,4-diamine Chemical compound CCC(N)CC(C)N HZJYYGGZHQIQKL-UHFFFAOYSA-N 0.000 claims description 8
- BBPXVYVXKAYBSS-UHFFFAOYSA-N hexane-2,5-diamine Chemical compound CC(N)CCC(C)N BBPXVYVXKAYBSS-UHFFFAOYSA-N 0.000 claims description 8
- GAZIERBSBYYJJW-UHFFFAOYSA-N octane-1,3-diamine Chemical compound CCCCCC(N)CCN GAZIERBSBYYJJW-UHFFFAOYSA-N 0.000 claims description 8
- YWUZKDXKGNGBKS-UHFFFAOYSA-N octane-1,4-diamine Chemical compound CCCCC(N)CCCN YWUZKDXKGNGBKS-UHFFFAOYSA-N 0.000 claims description 8
- BVTYNAVVDFBATM-UHFFFAOYSA-N octane-1,5-diamine Chemical compound CCCC(N)CCCCN BVTYNAVVDFBATM-UHFFFAOYSA-N 0.000 claims description 8
- JGQDLMSXMOGEMC-UHFFFAOYSA-N pentane-2,4-diamine Chemical compound CC(N)CC(C)N JGQDLMSXMOGEMC-UHFFFAOYSA-N 0.000 claims description 8
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 8
- BFHYUNGMDZAKAQ-UHFFFAOYSA-N 2-methylprop-2-enoyl 3-oxobutaneperoxoate Chemical class CC(=O)CC(=O)OOC(=O)C(C)=C BFHYUNGMDZAKAQ-UHFFFAOYSA-N 0.000 claims description 7
- NNPBMDHKRNKXAM-UHFFFAOYSA-N 3-methylhexane-1,5-diamine Chemical compound CC(N)CC(C)CCN NNPBMDHKRNKXAM-UHFFFAOYSA-N 0.000 claims description 7
- VIZDVWMUBSZSMV-UHFFFAOYSA-N 5-methylhexane-1,3-diamine Chemical compound CC(C)CC(N)CCN VIZDVWMUBSZSMV-UHFFFAOYSA-N 0.000 claims description 7
- RPLXGDGIXIJNQD-UHFFFAOYSA-N hexane-1,3-diamine Chemical compound CCCC(N)CCN RPLXGDGIXIJNQD-UHFFFAOYSA-N 0.000 claims description 7
- UEICEJLUNGARHQ-UHFFFAOYSA-N pentane-1,4-diamine Chemical compound CC(N)CCCN UEICEJLUNGARHQ-UHFFFAOYSA-N 0.000 claims description 7
- HGWZSJBCZYDDHY-UHFFFAOYSA-N 1-prop-2-enoyloxydecyl prop-2-enoate Chemical compound CCCCCCCCCC(OC(=O)C=C)OC(=O)C=C HGWZSJBCZYDDHY-UHFFFAOYSA-N 0.000 claims description 5
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 claims description 5
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 claims description 5
- XAMCLRBWHRRBCN-UHFFFAOYSA-N 5-prop-2-enoyloxypentyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCOC(=O)C=C XAMCLRBWHRRBCN-UHFFFAOYSA-N 0.000 claims description 5
- CKDIBPOOPFHEAK-UHFFFAOYSA-N 7-prop-2-enoyloxyheptyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCOC(=O)C=C CKDIBPOOPFHEAK-UHFFFAOYSA-N 0.000 claims description 5
- 150000003973 alkyl amines Chemical class 0.000 claims description 5
- 125000005265 dialkylamine group Chemical group 0.000 claims description 5
- 125000005270 trialkylamine group Chemical group 0.000 claims description 5
- IHNQLRURNALWRJ-UHFFFAOYSA-N 8-prop-2-enoyloxyoctyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCCOC(=O)C=C IHNQLRURNALWRJ-UHFFFAOYSA-N 0.000 claims description 4
- PGDIJTMOHORACQ-UHFFFAOYSA-N 9-prop-2-enoyloxynonyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCCCOC(=O)C=C PGDIJTMOHORACQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000006185 dispersion Substances 0.000 claims description 4
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical group CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 claims description 3
- 229940043264 dodecyl sulfate Drugs 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims 1
- 125000004386 diacrylate group Chemical group 0.000 claims 1
- 238000005065 mining Methods 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract description 32
- 239000010410 layer Substances 0.000 description 93
- 239000011541 reaction mixture Substances 0.000 description 74
- 239000000243 solution Substances 0.000 description 39
- 239000007864 aqueous solution Substances 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 33
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 24
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 24
- 239000002585 base Substances 0.000 description 24
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 19
- 239000000523 sample Substances 0.000 description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 18
- 239000003999 initiator Substances 0.000 description 16
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 15
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 15
- 239000000839 emulsion Substances 0.000 description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 12
- 239000004793 Polystyrene Substances 0.000 description 12
- 229920002223 polystyrene Polymers 0.000 description 12
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 12
- 238000003860 storage Methods 0.000 description 12
- 238000010992 reflux Methods 0.000 description 11
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 6
- 229940001584 sodium metabisulfite Drugs 0.000 description 6
- 235000010262 sodium metabisulphite Nutrition 0.000 description 6
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 229910017974 NH40H Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- 230000016507 interphase Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 3
- 238000007720 emulsion polymerization reaction Methods 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- IAXXETNIOYFMLW-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) 2-methylprop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C(=C)C)CC1C2(C)C IAXXETNIOYFMLW-UHFFFAOYSA-N 0.000 description 2
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 2
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 239000004908 Emulsion polymer Substances 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000013068 control sample Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- FDPPXZRLXIPXJB-UHFFFAOYSA-N (2-methyl-2-nitropropyl) prop-2-enoate Chemical compound [O-][N+](=O)C(C)(C)COC(=O)C=C FDPPXZRLXIPXJB-UHFFFAOYSA-N 0.000 description 1
- POTYORUTRLSAGZ-UHFFFAOYSA-N (3-chloro-2-hydroxypropyl) prop-2-enoate Chemical compound ClCC(O)COC(=O)C=C POTYORUTRLSAGZ-UHFFFAOYSA-N 0.000 description 1
- MNSWITGNWZSAMC-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl prop-2-enoate Chemical compound FC(F)(F)C(C(F)(F)F)OC(=O)C=C MNSWITGNWZSAMC-UHFFFAOYSA-N 0.000 description 1
- VBHXIMACZBQHPX-UHFFFAOYSA-N 2,2,2-trifluoroethyl prop-2-enoate Chemical compound FC(F)(F)COC(=O)C=C VBHXIMACZBQHPX-UHFFFAOYSA-N 0.000 description 1
- WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 1
- GSQIVVSEVORPJF-UHFFFAOYSA-N 2-(butylamino)ethyl prop-2-enoate Chemical compound CCCCNCCOC(=O)C=C GSQIVVSEVORPJF-UHFFFAOYSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- WHBAYNMEIXUTJV-UHFFFAOYSA-N 2-chloroethyl prop-2-enoate Chemical compound ClCCOC(=O)C=C WHBAYNMEIXUTJV-UHFFFAOYSA-N 0.000 description 1
- ISRGONDNXBCDBM-UHFFFAOYSA-N 2-chlorostyrene Chemical compound ClC1=CC=CC=C1C=C ISRGONDNXBCDBM-UHFFFAOYSA-N 0.000 description 1
- FWWXYLGCHHIKNY-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate Chemical compound CCOCCOC(=O)C=C FWWXYLGCHHIKNY-UHFFFAOYSA-N 0.000 description 1
- JGRXEBOFWPLEAV-UHFFFAOYSA-N 2-ethylbutyl prop-2-enoate Chemical compound CCC(CC)COC(=O)C=C JGRXEBOFWPLEAV-UHFFFAOYSA-N 0.000 description 1
- NJRHMGPRPPEGQL-UHFFFAOYSA-N 2-hydroxybutyl prop-2-enoate Chemical compound CCC(O)COC(=O)C=C NJRHMGPRPPEGQL-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
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- FURRSXHPLKQVIR-UHFFFAOYSA-N 2-methoxybutyl prop-2-enoate Chemical compound CCC(OC)COC(=O)C=C FURRSXHPLKQVIR-UHFFFAOYSA-N 0.000 description 1
- IXPWKHNDQICVPZ-UHFFFAOYSA-N 2-methylhex-1-en-3-yne Chemical compound CCC#CC(C)=C IXPWKHNDQICVPZ-UHFFFAOYSA-N 0.000 description 1
- HVVPYFQMCGANJX-UHFFFAOYSA-N 2-methylprop-2-enyl prop-2-enoate Chemical compound CC(=C)COC(=O)C=C HVVPYFQMCGANJX-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
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 1
- HPSGLFKWHYAKSF-UHFFFAOYSA-N 2-phenylethyl prop-2-enoate Chemical compound C=CC(=O)OCCC1=CC=CC=C1 HPSGLFKWHYAKSF-UHFFFAOYSA-N 0.000 description 1
- GQTFHSAAODFMHB-UHFFFAOYSA-N 2-prop-2-enoyloxyethanesulfonic acid Chemical compound OS(=O)(=O)CCOC(=O)C=C GQTFHSAAODFMHB-UHFFFAOYSA-N 0.000 description 1
- YHSYGCXKWUUKIK-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC(=O)C=C YHSYGCXKWUUKIK-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
- NPYMXLXNEYZTMQ-UHFFFAOYSA-N 3-methoxybutyl prop-2-enoate Chemical compound COC(C)CCOC(=O)C=C NPYMXLXNEYZTMQ-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- HAUXPEUSOPGTJM-UHFFFAOYSA-N 5,6-dihydroxyhexyl prop-2-enoate Chemical compound OCC(O)CCCCOC(=O)C=C HAUXPEUSOPGTJM-UHFFFAOYSA-N 0.000 description 1
- OCIFJWVZZUDMRL-UHFFFAOYSA-N 6-hydroxyhexyl prop-2-enoate Chemical compound OCCCCCCOC(=O)C=C OCIFJWVZZUDMRL-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920001651 Cyanoacrylate Polymers 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- PCVSIMQAFWRUEC-UHFFFAOYSA-N N2-[1-[methyl-(phenylmethyl)amino]-3-(2-naphthalenyl)-1-oxopropan-2-yl]-N1-(2-nitrophenyl)pyrrolidine-1,2-dicarboxamide Chemical compound C=1C=C2C=CC=CC2=CC=1CC(NC(=O)C1N(CCC1)C(=O)NC=1C(=CC=CC=1)[N+]([O-])=O)C(=O)N(C)CC1=CC=CC=C1 PCVSIMQAFWRUEC-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- QMEMFEMQJJOZGM-RMKNXTFCSA-N [(e)-3-phenylprop-2-enyl] prop-2-enoate Chemical compound C=CC(=O)OC\C=C\C1=CC=CC=C1 QMEMFEMQJJOZGM-RMKNXTFCSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- RNOOHTVUSNIPCJ-UHFFFAOYSA-N butan-2-yl prop-2-enoate Chemical compound CCC(C)OC(=O)C=C RNOOHTVUSNIPCJ-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- BTQLDZMOTPTCGG-UHFFFAOYSA-N cyclopentyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCC1 BTQLDZMOTPTCGG-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 description 1
- XWNVSPGTJSGNPU-UHFFFAOYSA-N ethyl 4-chloro-1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OCC)=CC2=C1Cl XWNVSPGTJSGNPU-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004890 malting Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- AWJZTPWDQYFQPQ-UHFFFAOYSA-N methyl 2-chloroprop-2-enoate Chemical compound COC(=O)C(Cl)=C AWJZTPWDQYFQPQ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002736 nonionic surfactant Substances 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
- 239000003973 paint Substances 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 pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- WPBNLDNIZUGLJL-UHFFFAOYSA-N prop-2-ynyl prop-2-enoate Chemical compound C=CC(=O)OCC#C WPBNLDNIZUGLJL-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
- 230000000246 remedial effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 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
- C08F285/00—Macromolecular compounds obtained by polymerising monomers on to preformed graft polymers
-
- 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
- C08F257/00—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00
- C08F257/02—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00 on to polymers of styrene or alkyl-substituted styrenes
-
- 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
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/003—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/570,199 US6355720B1 (en) | 2000-05-12 | 2000-05-12 | Latex formulations with reduced yellowing |
| US09/570,199 | 2000-05-12 | ||
| PCT/US2001/007403 WO2001088002A1 (en) | 2000-05-12 | 2001-03-08 | Latex formulations with reduced yellowing |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2408787A1 CA2408787A1 (en) | 2001-11-22 |
| CA2408787C true CA2408787C (en) | 2006-10-10 |
Family
ID=24278665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002408787A Expired - Fee Related CA2408787C (en) | 2000-05-12 | 2001-03-08 | Latex formulations with reduced yellowing |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6355720B1 (enExample) |
| EP (1) | EP1287051B9 (enExample) |
| JP (1) | JP4746248B2 (enExample) |
| KR (1) | KR100684681B1 (enExample) |
| CN (1) | CN1239546C (enExample) |
| AU (1) | AU2001247318A1 (enExample) |
| CA (1) | CA2408787C (enExample) |
| DE (1) | DE60123421T2 (enExample) |
| MX (1) | MXPA02011148A (enExample) |
| TW (1) | TW583237B (enExample) |
| WO (1) | WO2001088002A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7168084B1 (en) | 1992-12-09 | 2007-01-23 | Sedna Patent Services, Llc | Method and apparatus for targeting virtual objects |
| US20040176507A1 (en) * | 2003-03-07 | 2004-09-09 | Douglas Schoon | Covalently bonding nail primer |
| US20050131176A1 (en) * | 2003-12-10 | 2005-06-16 | Cheng-Le Zhao | Process for production of polymer dispersions containing an acetoacetate moiety |
| US7470751B2 (en) * | 2004-09-21 | 2008-12-30 | Basf Corporation | Stabilized water-borne polymer compositions for use as water-based coatings |
| US7576149B2 (en) * | 2006-05-31 | 2009-08-18 | Xerox Corporation | Varnish |
| EP2285475A4 (en) * | 2008-06-10 | 2012-10-10 | Aquatech Int Corp | MANUFACTURE OF A HIGH PERFORMANCE ULTRAFILTRATION MEMBRANE IN HOLLOW FIBERS |
| DE102009048978A1 (de) | 2009-10-09 | 2011-04-14 | Beiersdorf Ag | Gilbfreie Haarbehandlungsmittel mit Aminosilikonen |
| EP2508555B1 (en) | 2011-03-21 | 2015-05-13 | Electrolux Home Products Corporation N.V. | Process for producing pre-expandable plastic beads and beads obtainable according to said process |
| JP7428511B2 (ja) * | 2014-09-30 | 2024-02-06 | 株式会社日本触媒 | 樹脂エマルション |
| JP6387901B2 (ja) * | 2015-05-27 | 2018-09-12 | 京セラドキュメントソリューションズ株式会社 | 静電潜像現像用トナー |
| BR112019016443A2 (pt) * | 2017-02-08 | 2020-04-07 | Swimc Llc | método para produção de uma dispersão aquosa, composição de revestimento, e, artigo revestido |
| CN106957579A (zh) * | 2017-03-28 | 2017-07-18 | 北京华腾东光科技发展有限公司 | 具有防腐、耐磨性能的单组份丙烯酸酯涂料 |
| KR102385401B1 (ko) | 2017-09-26 | 2022-04-08 | 다우 글로벌 테크놀로지스 엘엘씨 | 수성 중합체 조성물 |
| EP4077554A2 (en) * | 2019-12-17 | 2022-10-26 | Agfa Nv | Aqueous dispersion of polymeric capsules |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2264224C3 (de) | 1972-12-30 | 1981-11-19 | Röhm GmbH, 6100 Darmstadt | Herstellung eines vernetzten Polystyrol-Emulsionspolymerisats und seine Verwendung zum Trüben von Kunststoffen auf Methacrylatbasis |
| US4133788A (en) | 1978-01-23 | 1979-01-09 | Borg-Warner Corporation | Polymer latex which is cross-linked with a dialkyl tin diacrylate in the preparation of grafted copolymers |
| US4308912A (en) | 1979-03-28 | 1982-01-05 | Knecht Bernath L | Heat transfer system |
| US4391928A (en) | 1981-09-04 | 1983-07-05 | Nl Industries, Inc. | Opacifying polymeric particle and uses |
| US4537916A (en) | 1984-06-25 | 1985-08-27 | The Dow Chemical Company | Structured latex particles which are film forming and a process for their preparation |
| US5106903A (en) | 1984-12-17 | 1992-04-21 | Lehigh University | Preparation of large particle size monodisperse latexes |
| US4717750A (en) | 1985-07-29 | 1988-01-05 | The Dow Chemical Company | Structure reinforced latex particles |
| US4683269A (en) | 1985-12-18 | 1987-07-28 | Reichhold Chemicals, Inc. | Opaque binder system |
| US4876313A (en) | 1986-08-29 | 1989-10-24 | Rohm And Haas Company | Grafted core-shell polymer compositions using polyfunctional compounds |
| US4939190A (en) | 1987-05-25 | 1990-07-03 | Dainippon Ink And Chemicals, Inc. | Aqueous emulsion-type pressure sensitive adhesives |
| US5219900A (en) | 1987-07-02 | 1993-06-15 | Imperial Chemical Industries Plc | Coatings |
| US4942201A (en) | 1988-08-29 | 1990-07-17 | Illinois Tool Works, Inc. | Adhesive for low temperature applications |
| US5053441A (en) | 1988-09-23 | 1991-10-01 | Union Oil Company Of California | Core/shell particles and process for making same |
| US4906684A (en) * | 1988-12-09 | 1990-03-06 | Rtz Chemicals, Ltd. | Ambient temperature curing polymer compositions containing acetoacetoxyethyl methacrylate, glycidyl methacrylate and a polymerizable acid |
| US5212251A (en) | 1990-09-24 | 1993-05-18 | Rohm And Haas Company | Alkali-resistant core-shell polymers |
| US5391624A (en) | 1992-02-10 | 1995-02-21 | S. C. Johnson & Son, Inc. | Thermosettable compositions |
| GB9408725D0 (en) * | 1994-05-03 | 1994-06-22 | Zeneca Resins Bv | Production of aqueous polymer compositions |
| DE69520916T2 (de) * | 1994-08-30 | 2001-11-08 | Agfa-Gevaert N.V., Mortsel | Neuer Kern-Hülle Latex zur Verwendung in photographischen Materialien |
| AU729319B2 (en) * | 1996-05-28 | 2001-02-01 | Eastman Chemical Company | Surfactant-containing acetoacetoxy-functional and enamine-functional polymers |
| US6028155A (en) * | 1997-05-21 | 2000-02-22 | Eastman Chemical Company | Surfactant-containing acetoacetoxy-functional and enamine-functional polymers |
| US5998543A (en) * | 1996-05-28 | 1999-12-07 | Eastman Chemical Company | Stable amino-containing polymer latex blends |
-
2000
- 2000-05-12 US US09/570,199 patent/US6355720B1/en not_active Expired - Lifetime
-
2001
- 2001-03-08 CA CA002408787A patent/CA2408787C/en not_active Expired - Fee Related
- 2001-03-08 DE DE60123421T patent/DE60123421T2/de not_active Expired - Lifetime
- 2001-03-08 JP JP2001585219A patent/JP4746248B2/ja not_active Expired - Fee Related
- 2001-03-08 CN CNB018093701A patent/CN1239546C/zh not_active Expired - Lifetime
- 2001-03-08 WO PCT/US2001/007403 patent/WO2001088002A1/en not_active Ceased
- 2001-03-08 AU AU2001247318A patent/AU2001247318A1/en not_active Abandoned
- 2001-03-08 EP EP01920240A patent/EP1287051B9/en not_active Expired - Lifetime
- 2001-03-08 KR KR1020027015167A patent/KR100684681B1/ko not_active Expired - Fee Related
- 2001-03-08 MX MXPA02011148A patent/MXPA02011148A/es active IP Right Grant
- 2001-03-22 TW TW090106748A patent/TW583237B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2003533563A (ja) | 2003-11-11 |
| EP1287051A1 (en) | 2003-03-05 |
| TW583237B (en) | 2004-04-11 |
| CN1439025A (zh) | 2003-08-27 |
| DE60123421D1 (de) | 2006-11-09 |
| US6355720B1 (en) | 2002-03-12 |
| JP4746248B2 (ja) | 2011-08-10 |
| WO2001088002A1 (en) | 2001-11-22 |
| EP1287051B1 (en) | 2006-09-27 |
| CN1239546C (zh) | 2006-02-01 |
| DE60123421T2 (de) | 2007-08-23 |
| KR20020091286A (ko) | 2002-12-05 |
| CA2408787A1 (en) | 2001-11-22 |
| EP1287051B9 (en) | 2007-04-25 |
| AU2001247318A1 (en) | 2001-11-26 |
| KR100684681B1 (ko) | 2007-02-22 |
| MXPA02011148A (es) | 2004-01-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2408787C (en) | Latex formulations with reduced yellowing | |
| US5859112A (en) | Production of aqueous polymer compositions | |
| WO2005049184A2 (en) | Aqueous dispersions containing multi-stage emulsion polymers | |
| CA2286855C (en) | Aqueous self-crosslinking copolymer dispersions, a process for preparing them and their use in binders for coating materials | |
| CA2441478A1 (en) | Aqueous resin dispersion and method for producing the same | |
| CA2465715C (en) | Cross-linkable polymer composition | |
| JP3895827B2 (ja) | 共重合体水分散液及びこれを含む水性塗料用樹脂組成物 | |
| KR100290596B1 (ko) | 양이온성 에멀젼의 제조방법 | |
| US6174963B1 (en) | Method for producing amphoteric resin having dispersing function | |
| JP4038392B2 (ja) | 耐水性カチオン性微粒子樹脂組成物及びその製造方法 | |
| JP2004099823A (ja) | 水性被覆組成物 | |
| JP3592959B2 (ja) | 水性樹脂分散体の製造方法 | |
| JPH08311407A (ja) | アセトアセテート官能性ポリマー及び多官能性アミンを含有する水性組成物 | |
| JPH09143447A (ja) | 硝子瓶等の紫外線吸収剤 | |
| US20040068043A1 (en) | Aqueous resin dispersion and method for producing the same | |
| JPH06107713A (ja) | 共重合体水性エマルジョンおよび該エマルジョンを用いたシリコーン塗布紙の下曳剤 | |
| JPH06212094A (ja) | 水性オーバープリントワニス組成物 | |
| GB2413330A (en) | Vinyl graft polymer composition | |
| JPH0211607B2 (enExample) | ||
| JPH10114884A (ja) | コーティング剤 | |
| JP2010024456A (ja) | 水性被覆組成物 | |
| MXPA96005505A (en) | Production of aqueous compositions of polim | |
| CZ370999A3 (cs) | Vodné, samozesíťující disperse kopolymerů, způsob jejich výroby a jejich použití v lékařských pojivech | |
| MXPA96005526A (en) | Production of aqueous compositions of polim | |
| JPS6128699B2 (enExample) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |