JP2003533563A5 - - Google Patents
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- Publication number
- JP2003533563A5 JP2003533563A5 JP2001585219A JP2001585219A JP2003533563A5 JP 2003533563 A5 JP2003533563 A5 JP 2003533563A5 JP 2001585219 A JP2001585219 A JP 2001585219A JP 2001585219 A JP2001585219 A JP 2001585219A JP 2003533563 A5 JP2003533563 A5 JP 2003533563A5
- Authority
- JP
- Japan
- Prior art keywords
- diaminohexane
- methyl
- group
- combinations
- monomer
- 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.)
- Granted
Links
- 239000000178 monomer Substances 0.000 description 133
- 239000000203 mixture Substances 0.000 description 99
- 239000004816 latex Substances 0.000 description 82
- 229920000126 latex Polymers 0.000 description 82
- 238000009472 formulation Methods 0.000 description 75
- 229920000642 polymer Polymers 0.000 description 68
- 238000004383 yellowing Methods 0.000 description 58
- 230000001747 exhibiting effect Effects 0.000 description 44
- -1 alkyl methacrylates Chemical class 0.000 description 39
- 125000004432 carbon atom Chemical group C* 0.000 description 27
- 150000001412 amines Chemical class 0.000 description 23
- 238000004519 manufacturing process Methods 0.000 description 22
- 229920002554 vinyl polymer Polymers 0.000 description 22
- 125000005250 alkyl acrylate group Chemical group 0.000 description 18
- 239000002245 particle Substances 0.000 description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
- 229910052799 carbon Inorganic materials 0.000 description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 14
- 125000003277 amino group Chemical group 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- 239000003638 chemical reducing agent Substances 0.000 description 12
- WTSXICLFTPPDTL-UHFFFAOYSA-N pentane-1,3-diamine Chemical compound CCC(N)CCN WTSXICLFTPPDTL-UHFFFAOYSA-N 0.000 description 12
- 239000004094 surface-active agent Substances 0.000 description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 8
- 229910021529 ammonia Inorganic materials 0.000 description 8
- 239000000908 ammonium hydroxide Substances 0.000 description 8
- 230000000379 polymerizing effect Effects 0.000 description 8
- 239000007870 radical polymerization initiator Substances 0.000 description 8
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 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 description 6
- QSMCLIWFRATFMT-UHFFFAOYSA-N 2-methylhexane-1,4-diamine Chemical compound CCC(N)CC(C)CN QSMCLIWFRATFMT-UHFFFAOYSA-N 0.000 description 6
- ACEKLXGWCBIDGA-UHFFFAOYSA-N 2-methylpentane-1,4-diamine Chemical compound CC(N)CC(C)CN ACEKLXGWCBIDGA-UHFFFAOYSA-N 0.000 description 6
- BWVXSUHAWILBTN-UHFFFAOYSA-N 3-methylhexane-1,3-diamine Chemical compound CCCC(C)(N)CCN BWVXSUHAWILBTN-UHFFFAOYSA-N 0.000 description 6
- LZEHBXAZHLVXLW-UHFFFAOYSA-N 3-methylhexane-1,4-diamine Chemical compound CCC(N)C(C)CCN LZEHBXAZHLVXLW-UHFFFAOYSA-N 0.000 description 6
- NNPBMDHKRNKXAM-UHFFFAOYSA-N 3-methylhexane-1,5-diamine Chemical compound CC(N)CC(C)CCN NNPBMDHKRNKXAM-UHFFFAOYSA-N 0.000 description 6
- OLTBRQIRRDQOTO-UHFFFAOYSA-N 3-methylpentane-1,4-diamine Chemical compound CC(N)C(C)CCN OLTBRQIRRDQOTO-UHFFFAOYSA-N 0.000 description 6
- HKTQMCDAQDHXDJ-UHFFFAOYSA-N 4-methylhexane-1,3-diamine Chemical compound CCC(C)C(N)CCN HKTQMCDAQDHXDJ-UHFFFAOYSA-N 0.000 description 6
- NYCNZFKSGAOSCE-UHFFFAOYSA-N 4-methylhexane-1,5-diamine Chemical compound CC(N)C(C)CCCN NYCNZFKSGAOSCE-UHFFFAOYSA-N 0.000 description 6
- FAKVQKOINPDRTH-UHFFFAOYSA-N 4-methylpentane-1,3-diamine Chemical compound CC(C)C(N)CCN FAKVQKOINPDRTH-UHFFFAOYSA-N 0.000 description 6
- VIZDVWMUBSZSMV-UHFFFAOYSA-N 5-methylhexane-1,3-diamine Chemical compound CC(C)CC(N)CCN VIZDVWMUBSZSMV-UHFFFAOYSA-N 0.000 description 6
- ULEAQRIQMIQDPJ-UHFFFAOYSA-N butane-1,2-diamine Chemical compound CCC(N)CN ULEAQRIQMIQDPJ-UHFFFAOYSA-N 0.000 description 6
- RGTXVXDNHPWPHH-UHFFFAOYSA-N butane-1,3-diamine Chemical compound CC(N)CCN RGTXVXDNHPWPHH-UHFFFAOYSA-N 0.000 description 6
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical group [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 6
- DNDUSOASNMMTNN-UHFFFAOYSA-N heptane-1,3-diamine Chemical compound CCCCC(N)CCN DNDUSOASNMMTNN-UHFFFAOYSA-N 0.000 description 6
- RPLXGDGIXIJNQD-UHFFFAOYSA-N hexane-1,3-diamine Chemical compound CCCC(N)CCN RPLXGDGIXIJNQD-UHFFFAOYSA-N 0.000 description 6
- HYQBVSXBLGKEDT-UHFFFAOYSA-N hexane-1,4-diamine Chemical compound CCC(N)CCCN HYQBVSXBLGKEDT-UHFFFAOYSA-N 0.000 description 6
- XTBMQKZEIICCCS-UHFFFAOYSA-N hexane-1,5-diamine Chemical compound CC(N)CCCCN XTBMQKZEIICCCS-UHFFFAOYSA-N 0.000 description 6
- HZJYYGGZHQIQKL-UHFFFAOYSA-N hexane-2,4-diamine Chemical compound CCC(N)CC(C)N HZJYYGGZHQIQKL-UHFFFAOYSA-N 0.000 description 6
- BBPXVYVXKAYBSS-UHFFFAOYSA-N hexane-2,5-diamine Chemical compound CC(N)CCC(C)N BBPXVYVXKAYBSS-UHFFFAOYSA-N 0.000 description 6
- GAZIERBSBYYJJW-UHFFFAOYSA-N octane-1,3-diamine Chemical compound CCCCCC(N)CCN GAZIERBSBYYJJW-UHFFFAOYSA-N 0.000 description 6
- YWUZKDXKGNGBKS-UHFFFAOYSA-N octane-1,4-diamine Chemical compound CCCCC(N)CCCN YWUZKDXKGNGBKS-UHFFFAOYSA-N 0.000 description 6
- BVTYNAVVDFBATM-UHFFFAOYSA-N octane-1,5-diamine Chemical compound CCCC(N)CCCCN BVTYNAVVDFBATM-UHFFFAOYSA-N 0.000 description 6
- UEICEJLUNGARHQ-UHFFFAOYSA-N pentane-1,4-diamine Chemical compound CC(N)CCCN UEICEJLUNGARHQ-UHFFFAOYSA-N 0.000 description 6
- JGQDLMSXMOGEMC-UHFFFAOYSA-N pentane-2,4-diamine Chemical compound CC(N)CC(C)N JGQDLMSXMOGEMC-UHFFFAOYSA-N 0.000 description 6
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical group CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 6
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 5
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 150000003973 alkyl amines Chemical class 0.000 description 4
- 125000005265 dialkylamine group Chemical group 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- APWFJLJAQRZQIV-UHFFFAOYSA-N heptane-1,4-diamine Chemical compound CCCC(N)CCCN APWFJLJAQRZQIV-UHFFFAOYSA-N 0.000 description 4
- 125000005270 trialkylamine group Chemical group 0.000 description 4
- 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 description 3
- VQGRILOLJITFOR-UHFFFAOYSA-N 2-methylhexane-1,5-diamine Chemical compound CC(N)CCC(C)CN VQGRILOLJITFOR-UHFFFAOYSA-N 0.000 description 3
- PGXBLKMCNUKABP-UHFFFAOYSA-N 2-methylpentane-1,3-diamine Chemical compound CCC(N)C(C)CN PGXBLKMCNUKABP-UHFFFAOYSA-N 0.000 description 3
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 3
- NMUAPCBYDLETHO-UHFFFAOYSA-N 3-prop-2-enoyloxypentyl prop-2-enoate Chemical compound C=CC(=O)OC(CC)CCOC(=O)C=C NMUAPCBYDLETHO-UHFFFAOYSA-N 0.000 description 3
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 3
- XJMFFJYZSJMGGP-UHFFFAOYSA-N 5-methylhexane-1,4-diamine Chemical compound CC(C)C(N)CCCN XJMFFJYZSJMGGP-UHFFFAOYSA-N 0.000 description 3
- XAMCLRBWHRRBCN-UHFFFAOYSA-N 5-prop-2-enoyloxypentyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCOC(=O)C=C XAMCLRBWHRRBCN-UHFFFAOYSA-N 0.000 description 3
- CKDIBPOOPFHEAK-UHFFFAOYSA-N 7-prop-2-enoyloxyheptyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCOC(=O)C=C CKDIBPOOPFHEAK-UHFFFAOYSA-N 0.000 description 3
- IHNQLRURNALWRJ-UHFFFAOYSA-N 8-prop-2-enoyloxyoctyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCCOC(=O)C=C IHNQLRURNALWRJ-UHFFFAOYSA-N 0.000 description 3
- PGDIJTMOHORACQ-UHFFFAOYSA-N 9-prop-2-enoyloxynonyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCCCOC(=O)C=C PGDIJTMOHORACQ-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- IZKZIDXHCDIZKY-UHFFFAOYSA-N heptane-1,1-diamine Chemical group CCCCCCC(N)N IZKZIDXHCDIZKY-UHFFFAOYSA-N 0.000 description 3
- ZOMZNNQGMGBLHO-UHFFFAOYSA-N heptane-1,5-diamine Chemical compound CCC(N)CCCCN ZOMZNNQGMGBLHO-UHFFFAOYSA-N 0.000 description 3
- BFHYUNGMDZAKAQ-UHFFFAOYSA-N 2-methylprop-2-enoyl 3-oxobutaneperoxoate Chemical compound CC(=O)CC(=O)OOC(=O)C(C)=C BFHYUNGMDZAKAQ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical group CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 2
- 229940043264 dodecyl sulfate Drugs 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/570,199 | 2000-05-12 | ||
| US09/570,199 US6355720B1 (en) | 2000-05-12 | 2000-05-12 | Latex formulations with reduced yellowing |
| PCT/US2001/007403 WO2001088002A1 (en) | 2000-05-12 | 2001-03-08 | Latex formulations with reduced yellowing |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003533563A JP2003533563A (ja) | 2003-11-11 |
| JP2003533563A5 true JP2003533563A5 (enExample) | 2008-05-01 |
| JP4746248B2 JP4746248B2 (ja) | 2011-08-10 |
Family
ID=24278665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001585219A Expired - Fee Related JP4746248B2 (ja) | 2000-05-12 | 2001-03-08 | 黄変が軽減されたラテックス配合物 |
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 |
| CN102089070A (zh) * | 2008-06-10 | 2011-06-08 | 水技术国际公司 | 高性能超滤中空纤维膜的制备 |
| 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 |
| MX2019009492A (es) * | 2017-02-08 | 2019-09-27 | Swimc Llc | Composicion de revestimiento acuosa que no daña el medio ambiente. |
| 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 |
| JP7471418B2 (ja) * | 2019-12-17 | 2024-04-19 | アグファ・ナームローゼ・フェンノートシャップ | 高分子カプセルの水性分散体 |
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 |
| 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 |
| ES2179349T3 (es) * | 1996-05-28 | 2003-01-16 | Eastman Chem Co | Polimeros con grupos funcionales acetoacetoxi y enamina que contienen tensioactivos. |
-
2000
- 2000-05-12 US US09/570,199 patent/US6355720B1/en not_active Expired - Lifetime
-
2001
- 2001-03-08 DE DE60123421T patent/DE60123421T2/de not_active Expired - Lifetime
- 2001-03-08 CA CA002408787A patent/CA2408787C/en not_active Expired - Fee Related
- 2001-03-08 AU AU2001247318A patent/AU2001247318A1/en not_active Abandoned
- 2001-03-08 CN CNB018093701A patent/CN1239546C/zh not_active Expired - Lifetime
- 2001-03-08 MX MXPA02011148A patent/MXPA02011148A/es active IP Right Grant
- 2001-03-08 JP JP2001585219A patent/JP4746248B2/ja not_active Expired - Fee Related
- 2001-03-08 KR KR1020027015167A patent/KR100684681B1/ko not_active Expired - Fee Related
- 2001-03-08 WO PCT/US2001/007403 patent/WO2001088002A1/en not_active Ceased
- 2001-03-08 EP EP01920240A patent/EP1287051B9/en not_active Expired - Lifetime
- 2001-03-22 TW TW090106748A patent/TW583237B/zh not_active IP Right Cessation
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