CN100549055C - 来自原子转移自由基聚合的大分子单体的梳形聚合物 - Google Patents
来自原子转移自由基聚合的大分子单体的梳形聚合物 Download PDFInfo
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- CN100549055C CN100549055C CNB2003101047562A CN200310104756A CN100549055C CN 100549055 C CN100549055 C CN 100549055C CN B2003101047562 A CNB2003101047562 A CN B2003101047562A CN 200310104756 A CN200310104756 A CN 200310104756A CN 100549055 C CN100549055 C CN 100549055C
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- Prior art keywords
- acid
- alkyl
- vinylformic acid
- salt
- ester
- Prior art date
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- 229910052801 chlorine Inorganic materials 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 8
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- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
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- 239000004584 polyacrylic acid Substances 0.000 description 1
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- 229920006254 polymer film Polymers 0.000 description 1
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- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 1
- ORIHZIZPTZTNCU-YVMONPNESA-N salicylaldoxime Chemical compound O\N=C/C1=CC=CC=C1O ORIHZIZPTZTNCU-YVMONPNESA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229960002668 sodium chloride Drugs 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229960004306 sulfadiazine Drugs 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- RKSOPLXZQNSWAS-UHFFFAOYSA-N tert-butyl bromide Chemical compound CC(C)(C)Br RKSOPLXZQNSWAS-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- GZBUMTPCIKCWFW-UHFFFAOYSA-N triethylcholine Chemical class CC[N+](CC)(CC)CCO GZBUMTPCIKCWFW-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
-
- 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
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such 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
- C08F2438/00—Living radical polymerisation
- C08F2438/01—Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
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)
- Graft Or Block Polymers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00810023 | 2000-01-11 | ||
| EP00810023.2 | 2000-01-11 |
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| CNB018036414A Division CN100497420C (zh) | 2000-01-11 | 2001-01-04 | 来自原子转移自由基聚合的大分子单体的梳形聚合物 |
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| CN1506390A CN1506390A (zh) | 2004-06-23 |
| CN100549055C true CN100549055C (zh) | 2009-10-14 |
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| CNB018036414A Expired - Fee Related CN100497420C (zh) | 2000-01-11 | 2001-01-04 | 来自原子转移自由基聚合的大分子单体的梳形聚合物 |
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| CNB018036414A Expired - Fee Related CN100497420C (zh) | 2000-01-11 | 2001-01-04 | 来自原子转移自由基聚合的大分子单体的梳形聚合物 |
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| KR (1) | KR100673429B1 (enExample) |
| CN (2) | CN100549055C (enExample) |
| AU (1) | AU2001237275A1 (enExample) |
| BR (1) | BR0107548A (enExample) |
| CA (1) | CA2394660A1 (enExample) |
| MX (1) | MXPA02006782A (enExample) |
| WO (1) | WO2001051534A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6376597B1 (en) * | 1999-12-16 | 2002-04-23 | Ppg Industries Ohio, Inc. | Pigment dispersions containing dispersants having pendent hydrophilic polymeric segments prepared by controlled radical polymerization |
| TW200407363A (en) | 2001-11-29 | 2004-05-16 | Ciba Sc Holding Ag | Pigment compositions with modified ATRP copolymer dispersants |
| US6582510B1 (en) * | 2002-04-16 | 2003-06-24 | Arco Chemical Technology, L.P. | Use of comb-branched copolymers as pigment dispersants |
| DE10237286A1 (de) * | 2002-08-14 | 2004-02-26 | Degussa Construction Chemicals Gmbh | Verwendung von Blockcopolymeren als Dilpergiermittel für wässrige Feststoff-Suspensionen |
| US20060178450A1 (en) * | 2003-02-20 | 2006-08-10 | Vincent Ruffieux | Easily dispersible pigment composition |
| WO2004078839A1 (en) * | 2003-03-03 | 2004-09-16 | Ciba Specialty Chemicals Holding Inc. | Process for intercalating natural or sznthetic clays with block or comb copolymers |
| RU2350632C2 (ru) * | 2003-06-24 | 2009-03-27 | Полимерс Острейлиа Пти. Лимитед | Акриловые диспергирующие агенты в нанокомпозитах |
| GB2418204A (en) * | 2004-09-21 | 2006-03-22 | Sun Chemical Ltd | Energy-curable intaglio printing inks |
| EP1734384A4 (en) * | 2004-04-09 | 2010-10-20 | Kimoto Kk | LIGHT CONTROL SHEET AND LIGHT SURFACE SOURCE USING THE SAME |
| WO2006007364A2 (en) * | 2004-06-10 | 2006-01-19 | Degussa Corporation | Heat-stable colorant compositions for polymers |
| JP2006016488A (ja) * | 2004-07-01 | 2006-01-19 | Toyo Ink Mfg Co Ltd | 樹脂のグラフトされた有機顔料およびその製造方法 |
| US20090275705A1 (en) * | 2005-03-28 | 2009-11-05 | Kaneka Corporation | Acrylic Block Copolymer and Reactive Hot-Melt Adhesive Compositions |
| JP2007002122A (ja) * | 2005-06-24 | 2007-01-11 | Fuji Xerox Co Ltd | インクジェット用インク、インクジェット用処理液、インクジェット用インクセット、インクジェット用インクタンク、インクジェット記録方法、及びインクジェット記録装置 |
| JP4963031B2 (ja) * | 2006-03-15 | 2012-06-27 | 花王株式会社 | 非水系顔料分散剤 |
| KR101399722B1 (ko) * | 2006-03-15 | 2014-05-26 | 카오카부시키가이샤 | 비수계 안료 분산 조성물 |
| CN101426861B (zh) | 2006-04-21 | 2011-12-28 | 日本板硝子株式会社 | 光辉性颜料及其制造方法以及含有该光辉性颜料的水性树脂组合物 |
| EP2058374B1 (en) * | 2006-08-29 | 2013-03-27 | Nippon Sheet Glass Company, Limited | Pearlescent pigment |
| EP2104694B1 (en) | 2006-12-28 | 2012-09-26 | Nuplex Resins B.V. | Waterborne polymeric dispersions |
| EP2147954B1 (en) * | 2007-04-18 | 2017-12-13 | Nippon Sheet Glass Company, Limited | Photoluminescent pigment and cosmetic composition using the same |
| US8440014B2 (en) * | 2007-04-27 | 2013-05-14 | Nippon Sheet Glass Company, Limited | Bright pigment, and bright coating composition and automotive body coating each containing the same |
| EP2213705B1 (en) * | 2007-10-18 | 2012-12-12 | Nippon Sheet Glass Company, Limited | Bright Pigment |
| JP5726164B2 (ja) | 2009-03-24 | 2015-05-27 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 成形金属粒子の製造およびその使用 |
| CN101845129B (zh) * | 2010-05-21 | 2012-07-04 | 中科院广州化学有限公司 | 有机硅(甲基)丙烯酸酯aba型嵌段共聚物及其制备方法和应用 |
| CN101899132B (zh) * | 2010-07-26 | 2012-04-25 | 鲁东大学 | 一种聚丙烯腈吸附材料的制备方法 |
| WO2012033226A1 (ja) * | 2010-09-08 | 2012-03-15 | 関西ペイント株式会社 | 水性エポキシ樹脂塗料組成物用キット、水性エポキシ樹脂塗料組成物、塗装物品の形成方法、及び塗装物品 |
| CN102010491B (zh) * | 2010-11-11 | 2012-05-30 | 常州大学 | 甲基丙烯酸二甲氨基乙酯-丙烯酸丁酯共聚物的制备方法 |
| CN102700260B (zh) * | 2012-05-27 | 2014-12-10 | 沈玉琴 | 一种瓷砖喷墨前的处理方法 |
| EP2935348A4 (en) | 2012-12-18 | 2016-06-29 | Henkel IP & Holding GmbH | METHOD FOR CONTROLLED RADICAL POLYMERIZATION OF BRANCHED POLYACRYLATES |
| EP3033361A4 (en) * | 2013-08-12 | 2017-05-03 | Henkel IP & Holding GmbH | Alkoxysilane-functionalized polyacrylate compositions and methods of preparation thereof |
| ES2665813T3 (es) | 2013-11-04 | 2018-04-27 | Lubrizol Advanced Materials, Inc. | Dispersantes acrílicos con grupos de anclaje imida aromáticos fusionados |
| US10570237B2 (en) | 2013-11-29 | 2020-02-25 | Mitsubishi Chemical Corporation | (Meth)acrylic copolymer, adhesive composition containing same, and adhesive sheet |
| FR3018814B1 (fr) * | 2014-03-24 | 2016-03-04 | Rhodia Operations | Polymeres amphiphiles multibloc |
| DE112015001730T5 (de) * | 2014-04-08 | 2016-12-29 | Toyo Tire & Rubber Co., Ltd. | Kautschukzusammensetzung und pneumatischer Reifen |
| TWI516520B (zh) | 2014-10-31 | 2016-01-11 | 財團法人工業技術研究院 | 波長轉換聚合物、其製法及包含其之波長轉換裝置 |
| CN104387841A (zh) * | 2014-11-11 | 2015-03-04 | 合肥皖为电气设备工程有限责任公司 | 一种添加聚乙烯蜡的新型印刷油墨及其制作方法 |
| CN104387846A (zh) * | 2014-11-11 | 2015-03-04 | 合肥皖为电气设备工程有限责任公司 | 一种性价比高的印刷油墨及其制作方法 |
| WO2017132380A1 (en) | 2016-01-29 | 2017-08-03 | Lubrizol Advanced Materials, Inc. | Polymeric dispersants containing multi-amine groups with improved chemical and thermal stability |
| CN105694564A (zh) * | 2016-04-27 | 2016-06-22 | 柳州申通汽车科技有限公司 | 汽车涂料及其加工工艺 |
| CN105694697A (zh) * | 2016-04-27 | 2016-06-22 | 柳州申通汽车科技有限公司 | 水性汽车纳米涂料及其加工工艺 |
| BR112019008281B1 (pt) * | 2016-11-04 | 2022-10-11 | Basf Se | Composto, método para preparar um composto, polímero, método para preparar o polímero, composição líquida, e, uso de pelo menos um polímero |
| CN108079980A (zh) * | 2016-11-21 | 2018-05-29 | 中国科学院大连化学物理研究所 | 一种具有疏水性刷型聚合物涂层的色谱柱及制备和应用 |
| WO2018132582A1 (en) * | 2017-01-12 | 2018-07-19 | Carnegie Mellon University | Surfactant assisted formation of a catalyst complex for emulsion atom transfer radical polymerization processes |
| WO2020046531A1 (en) * | 2018-08-31 | 2020-03-05 | Dow Global Technologies Llc | Branched polymeric dispersants, aqueous pigment dispersions, and aqueous coating compositions thereof |
| CN111704696B (zh) * | 2020-06-24 | 2022-10-18 | 新乡学院 | 一种氟硅接枝改性丙烯酸树脂的制备方法 |
| CN112608406A (zh) * | 2020-11-27 | 2021-04-06 | 浙江可思克高新材料股份有限公司 | 一种重钙研磨分散剂及其制备方法 |
| CN114262414B (zh) * | 2022-01-24 | 2024-07-05 | 长春市兆兴新材料技术有限责任公司 | 一种梳型超高分子量聚合物及合成方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5807937A (en) * | 1995-11-15 | 1998-09-15 | Carnegie Mellon University | Processes based on atom (or group) transfer radical polymerization and novel (co) polymers having useful structures and properties |
| CN1228789C (zh) * | 2003-06-05 | 2005-11-23 | 北京英纳超导技术有限公司 | 一种超导导线及其制备方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3486145T2 (de) * | 1983-07-11 | 1993-09-23 | Commw Scient Ind Res Org | Verfahren zur polymerisation und nach diesem verfahren hergestellte polymere. |
| US4656226A (en) * | 1985-09-30 | 1987-04-07 | E. I. Du Pont De Nemours And Company | Acrylic pigment dispersants made by group transfer polymerization |
| US5109075A (en) * | 1988-06-06 | 1992-04-28 | The B. F. Goodrich Company | Comb-shaped graft copolymers of allyl terminated macromolecular monomers of polyethers |
| ES2110321T3 (es) * | 1994-04-30 | 1998-02-01 | Wacker Chemie Gmbh | Producto de revestimiento acuoso y proceso para la preparacion de revestimientos barnizados multicapa cuya sensacion de color depende del angulo de observacion. |
| US5763548A (en) * | 1995-03-31 | 1998-06-09 | Carnegie-Mellon University | (Co)polymers and a novel polymerization process based on atom (or group) transfer radical polymerization |
| US5789487A (en) * | 1996-07-10 | 1998-08-04 | Carnegie-Mellon University | Preparation of novel homo- and copolymers using atom transfer radical polymerization |
| US5859113A (en) | 1997-07-17 | 1999-01-12 | E. I. Du Pont De Nemours And Company | Pigment dispersions containing hydroxylated AB-block polymer dispersant |
| FR2770219A1 (fr) | 1997-10-24 | 1999-04-30 | Atochem Elf Sa | Procede de fabrication de copolymeres a architecture controlee a l'aide d'amorceurs radicalaires fonctionnels en polymerisation radicalaire vivante, et composes amorceurs et copolymeres correspondants |
| EP1059308B1 (en) | 1998-02-27 | 2006-10-11 | Kaneka Corporation | Polymer and curable composition |
| CA2335777C (en) * | 1998-06-19 | 2008-08-19 | Kaneka Corporation | Process for producing branched polymer and polymer |
| WO2000011055A1 (fr) | 1998-08-21 | 2000-03-02 | Elf Atochem S.A. | Procede de fabrication de copolymers a architecture controlee et copolymeres obtenus |
| ATE279447T1 (de) * | 1998-09-29 | 2004-10-15 | Ciba Sc Holding Ag | Verfahren zur herstellung von polymeren enthaltend endständige n-0 gruppen |
| KR100642674B1 (ko) | 1998-12-31 | 2006-11-10 | 시바 스폐셜티 케미칼스 홀딩 인코포레이티드 | Ａｔｒｐ중합체를 함유하는 안료 조성물 |
| US6462125B1 (en) * | 1999-12-16 | 2002-10-08 | Ppg Industries Ohio, Inc. | Pigment dispersions containing dispersants prepared by controlled radical polymerization having hydrophilic and hydrophobic segments |
-
2001
- 2001-01-04 MX MXPA02006782A patent/MXPA02006782A/es not_active Application Discontinuation
- 2001-01-04 EP EP01909579A patent/EP1254185A1/en not_active Withdrawn
- 2001-01-04 CN CNB2003101047562A patent/CN100549055C/zh not_active Expired - Fee Related
- 2001-01-04 KR KR1020027008859A patent/KR100673429B1/ko not_active Expired - Fee Related
- 2001-01-04 CN CNB018036414A patent/CN100497420C/zh not_active Expired - Fee Related
- 2001-01-04 CA CA002394660A patent/CA2394660A1/en not_active Abandoned
- 2001-01-04 BR BR0107548-9A patent/BR0107548A/pt not_active Application Discontinuation
- 2001-01-04 JP JP2001551118A patent/JP5290485B2/ja not_active Expired - Fee Related
- 2001-01-04 US US10/169,884 patent/US6936656B2/en not_active Expired - Lifetime
- 2001-01-04 WO PCT/EP2001/000053 patent/WO2001051534A1/en not_active Ceased
- 2001-01-04 AU AU2001237275A patent/AU2001237275A1/en not_active Abandoned
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5807937A (en) * | 1995-11-15 | 1998-09-15 | Carnegie Mellon University | Processes based on atom (or group) transfer radical polymerization and novel (co) polymers having useful structures and properties |
| CN1228789C (zh) * | 2003-06-05 | 2005-11-23 | 北京英纳超导技术有限公司 | 一种超导导线及其制备方法 |
Non-Patent Citations (1)
| Title |
|---|
| 原子转移自由基聚合在聚合物分子设计中的应用. 傅志峰，石艳，刘海涛，焦书科.胶体与聚合物，第17卷第01期. 1999 * |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20020070335A (ko) | 2002-09-05 |
| US6936656B2 (en) | 2005-08-30 |
| CN100497420C (zh) | 2009-06-10 |
| JP5290485B2 (ja) | 2013-09-18 |
| CN1506390A (zh) | 2004-06-23 |
| CN1395587A (zh) | 2003-02-05 |
| AU2001237275A1 (en) | 2001-07-24 |
| MXPA02006782A (es) | 2002-10-23 |
| US20030166755A1 (en) | 2003-09-04 |
| CA2394660A1 (en) | 2001-07-19 |
| KR100673429B1 (ko) | 2007-01-24 |
| BR0107548A (pt) | 2002-10-08 |
| WO2001051534A1 (en) | 2001-07-19 |
| EP1254185A1 (en) | 2002-11-06 |
| JP2003519703A (ja) | 2003-06-24 |
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