JP5185297B2 - 1つまたはそれ以上の第四級アンモニウム基を有するアクリル系モノマーおよびそのポリマーの製造方法 - Google Patents
1つまたはそれ以上の第四級アンモニウム基を有するアクリル系モノマーおよびそのポリマーの製造方法 Download PDFInfo
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- JP5185297B2 JP5185297B2 JP2009554559A JP2009554559A JP5185297B2 JP 5185297 B2 JP5185297 B2 JP 5185297B2 JP 2009554559 A JP2009554559 A JP 2009554559A JP 2009554559 A JP2009554559 A JP 2009554559A JP 5185297 B2 JP5185297 B2 JP 5185297B2
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- group
- monomer
- alkyl group
- quaternary ammonium
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/12—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/62—Quaternary ammonium compounds
- C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/60—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/60—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen
- C08F220/606—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen and containing other heteroatoms
-
- 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
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
-
- 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
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a single or double bond to nitrogen
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
(a)分子当たりに少なくとも1つのエチレン性不飽和基および少なくとも1つの第三級アミノ基を有する過剰の単量体型反応物を、ハロヒドロキシアルキル(トリアルキル)第四級アンモニウム塩と、水性媒体中で反応させること、
(b)遅くとも全ての反応物が水性媒体中に加えられた時から反応の完結まで、この水性媒体のpHを監視すること、および
(c)全ての反応物が水性媒体に加えられた後の、この反応混合物の見掛けのpHが最小値を示す時から、反応の完結まで、水性媒体のpHを9以上の値に調整および維持すること、を含む製造方法を指向している。
(a)エチレン性不飽和基および分子当たりに2つまたはそれ以上の第四級アンモニウム基を有するモノマーを、
(i)分子当たりに少なくとも1つのエチレン性不飽和基および少なくとも1つの第三級アミノ基を有する過剰の単量体をハロヒドロキシアルキル(トリアルキル)第四級アンモニウム塩と、水性媒体中で反応させること、
(ii)遅くとも全ての反応物が水性媒体中に加えられた時から反応の完結まで、この水性媒体のpHを監視すること、および
(iii)全ての反応物が水性媒体に加えられた後の、この反応混合物の見掛けのpHが最小値を示す時から、反応の完結まで、水性媒体のpHを9以上の値に調整および維持すること、によって調製すること、ならびに
(b)工程(a)で形成されたモノマーを重合開始剤混合物の存在下で重合させること、を含む製造方法を指向している。
また、中間体(III)は次いでモノマー(I)と反応して、目的の生成物(IV)および水酸基イオンを形成すると信じられる。しかしながら、中間体化合物(III)を経由した化合物(IV)への並行の経路はまた、酸残基を発生し、これが反応物の完全な転換より以前での反応の失速まで、化合物(IV)の生成を減速させる。理論に拘束されることは望まないが、本発明の方法のpH調整工程は、酸残基を中和し、そしてそれに伴う反応速度への阻害効果を克服させると、我々は信じている。
エチレン性不飽和基および分子当たりに2つの第四級アンモニウム基を有するモノマーをスキームA−1に従って製造した。
ポリマーの1つまたはそれ以上の単量体単位がそれぞれ単量体単位当たりに2つの第四級アンモニウム基を含む共重合体をスキームC−1に従って製造し、
Claims (8)
- エチレン性不飽和基および分子当たりに2つまたはそれ以上の第四級アンモニウム基を有するモノマーの製造方法であって、
(a)分子当たりに少なくとも1つのエチレン性不飽和基および少なくとも1つの第三級アミノ基を有する単量体型反応物を、下記の構造(II)
で表されるハロヒドロキシアルキル(トリアルキル)第四級アンモニウム塩と、該ハロヒドロキシアルキル(トリアルキル)第四級アンモニウム塩のモル当たり、該単量体型反応物が1.01モル以上で、水性媒体中で反応させること、
(b)遅くとも全ての反応物が水性媒体中に加えられた時から反応の完結まで、この水性媒体のpHを監視すること、および
(c)全ての反応物が水性媒体に加えられた後の、この反応混合物のpHが最小値を示す時から、反応の完結まで、水性媒体のpHを9以上の値に調整および維持すること、を含む製造方法。 - モノマー(IV)が以下のスキームA、
- R8がクロロ基である、請求項3記載の方法。
- ポリマーの1つまたはそれ以上の単量体単位が、単量体単位当たりにそれぞれ2つまたはそれ以上の第四級アンモニウム基を含むポリマーの製造方法であって、
(a)エチレン性不飽和基および分子当たりに2つまたはそれ以上の第四級アンモニウム基を有するモノマーを、
(i)分子当たりに少なくとも1つのエチレン性不飽和基および少なくとも1つの第三級アミノ基を有する単量体を、下記の構造(II)
で表されるハロヒドロキシアルキル(トリアルキル)第四級アンモニウム塩と、該ハロヒドロキシアルキル(トリアルキル)第四級アンモニウム塩のモル当たり、該単量体が1.01モル以上で、水性媒体中で反応させること、
(ii)遅くとも全ての反応物が水性媒体中に加えられた時から反応の完結まで、この水性媒体のpHを監視すること、および
(iii)全ての反応物が水性媒体に加えられた後の、この反応混合物のpHが最小値を示す時から、反応の完結まで、水性媒体のpHを9以上の値に調整および維持すること、によって調製すること、ならびに
(b)工程(a)で形成されたモノマーを重合開始剤混合物の存在下で重合させること、を含む製造方法。 - ポリマーが下記のスキームB、
- ポリマーが下記のスキームC、
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US91970507P | 2007-03-23 | 2007-03-23 | |
US60/919,705 | 2007-03-23 | ||
PCT/US2008/003589 WO2008118315A1 (en) | 2007-03-23 | 2008-03-19 | Process for making an acrylic monomer having one or more quaternary ammonium groups and its polymers |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2010522167A JP2010522167A (ja) | 2010-07-01 |
JP2010522167A5 JP2010522167A5 (ja) | 2012-10-18 |
JP5185297B2 true JP5185297B2 (ja) | 2013-04-17 |
Family
ID=39775407
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009554559A Expired - Fee Related JP5185297B2 (ja) | 2007-03-23 | 2008-03-19 | 1つまたはそれ以上の第四級アンモニウム基を有するアクリル系モノマーおよびそのポリマーの製造方法 |
Country Status (9)
Country | Link |
---|---|
US (1) | US7858722B2 (ja) |
EP (1) | EP2139849A4 (ja) |
JP (1) | JP5185297B2 (ja) |
KR (1) | KR101572596B1 (ja) |
CN (1) | CN101687771B (ja) |
BR (1) | BRPI0809312A2 (ja) |
CA (1) | CA2681763A1 (ja) |
RU (1) | RU2471773C2 (ja) |
WO (1) | WO2008118315A1 (ja) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
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US8541523B2 (en) | 2010-04-05 | 2013-09-24 | Promerus, Llc | Norbornene-type polymers, compositions thereof and lithographic process using such compositions |
CN102580607B (zh) * | 2011-12-30 | 2014-02-19 | 武汉理工大学 | 双季铵盐慢裂快凝沥青乳化剂的合成工艺 |
CN103554526B (zh) * | 2013-10-18 | 2015-03-04 | 辽宁石油化工大学 | 一种引入双季铵阳离子分子的阴离子交换膜及其制备方法 |
US10519602B2 (en) | 2017-06-15 | 2019-12-31 | Ecolab Usa Inc. | Polymer for pitch and stickies deposition control in papermaking |
CN107619660B (zh) * | 2017-11-02 | 2020-04-14 | 中国石油化工股份有限公司 | 胶凝酸稠化剂及其制备方法 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2856384C3 (de) * | 1978-12-27 | 1981-11-19 | Chemische Fabrik Stockhausen & Cie, 4150 Krefeld | Quartäre Ammoniumgruppen enthaltende Acrylyl- bzw. Methacrylylharnstoffe und Verfahren zu ihrer Herstellung |
US4387017A (en) | 1981-12-02 | 1983-06-07 | Texaco Inc. | Demulsification of bitumen emulsions using polymers of diquaternary ammonium monomers containing hydroxyl groups |
US4495367A (en) | 1982-07-06 | 1985-01-22 | Celanese Corporation | High charge density, cationic methacrylamide based monomers and their _polymers |
CA1235140A (en) * | 1982-07-06 | 1988-04-12 | Laurence G. Dammann | High charge density, cationic methacrylamide based monomers and their polymers |
CA1235141A (en) * | 1984-03-28 | 1988-04-12 | Laurence G. Dammann | High charge density, cationic methacrylamide based monomers and their polymers |
JPH0768678B2 (ja) * | 1985-10-04 | 1995-07-26 | 日本ピー・エム・シー株式会社 | 製紙用添加剤 |
US4973637A (en) * | 1989-02-23 | 1990-11-27 | Hi-Tek Polymers, Inc. | Polymers made from quaternary ammonium acrylic monomers |
RU2061679C1 (ru) * | 1993-01-19 | 1996-06-10 | Нижегородский политехнический институт | Соли n-[1,1-r,r-3-диметиламинопропил(поли-1,1-r,r,-7-оксо-4,4-диметил-4,8-диазаоктаметилен)]пропенамидов и способ их получения |
FR2796392B1 (fr) * | 1999-07-15 | 2003-09-19 | Rhodia Chimie Sa | Composition nettoyante comprenant un polymere hydrosoluble ou hydrodispersable |
US6596261B1 (en) | 2000-01-25 | 2003-07-22 | Aeropharm Technology Incorporated | Method of administering a medicinal aerosol formulation |
CA2682799A1 (en) | 2002-06-04 | 2003-12-11 | The Procter & Gamble Company | Conditioning shampoo compositions containing surfactant and cationic copolymer combination that forms liquid crystals |
BR0311469A (pt) | 2002-06-04 | 2005-03-15 | Rhodia | Composto de monÈmero que compreende diversos grupos catiÈnicos e polìmeros que compreendem unidades obtidas a partir deste |
US7064232B2 (en) | 2003-12-08 | 2006-06-20 | Rhodia Inc. | Hydrophobic modified diquaternary monomers and polymers as thickening agents of acidic aqueous compositions |
-
2008
- 2008-03-19 CN CN200880009512.7A patent/CN101687771B/zh not_active Expired - Fee Related
- 2008-03-19 CA CA002681763A patent/CA2681763A1/en not_active Abandoned
- 2008-03-19 BR BRPI0809312-1A2A patent/BRPI0809312A2/pt not_active Application Discontinuation
- 2008-03-19 KR KR1020097019448A patent/KR101572596B1/ko not_active IP Right Cessation
- 2008-03-19 EP EP08726971A patent/EP2139849A4/en not_active Withdrawn
- 2008-03-19 JP JP2009554559A patent/JP5185297B2/ja not_active Expired - Fee Related
- 2008-03-19 RU RU2009139076/04A patent/RU2471773C2/ru not_active IP Right Cessation
- 2008-03-19 WO PCT/US2008/003589 patent/WO2008118315A1/en active Application Filing
- 2008-03-19 US US12/077,326 patent/US7858722B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
JP2010522167A (ja) | 2010-07-01 |
KR101572596B1 (ko) | 2015-11-27 |
EP2139849A4 (en) | 2012-07-04 |
CN101687771B (zh) | 2014-06-18 |
US7858722B2 (en) | 2010-12-28 |
US20080234432A1 (en) | 2008-09-25 |
EP2139849A1 (en) | 2010-01-06 |
BRPI0809312A2 (pt) | 2014-10-14 |
CN101687771A (zh) | 2010-03-31 |
RU2009139076A (ru) | 2011-04-27 |
KR20100014452A (ko) | 2010-02-10 |
WO2008118315A1 (en) | 2008-10-02 |
CA2681763A1 (en) | 2008-10-02 |
RU2471773C2 (ru) | 2013-01-10 |
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