GB1112912A - Monomers with hydroxyl and quaternary ammonium functionality and polymers thereof - Google Patents
Monomers with hydroxyl and quaternary ammonium functionality and polymers thereofInfo
- Publication number
- GB1112912A GB1112912A GB3653065A GB3653065A GB1112912A GB 1112912 A GB1112912 A GB 1112912A GB 3653065 A GB3653065 A GB 3653065A GB 3653065 A GB3653065 A GB 3653065A GB 1112912 A GB1112912 A GB 1112912A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- quaternary ammonium
- formula
- esters
- anion
- 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
Links
- 239000000178 monomer Substances 0.000 title abstract 3
- 125000001453 quaternary ammonium group Chemical group 0.000 title abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title 1
- 229920000642 polymer Polymers 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 150000001450 anions Chemical class 0.000 abstract 4
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 239000000463 material Substances 0.000 abstract 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- -1 alkali metal salt Chemical class 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 150000003512 tertiary amines Chemical class 0.000 abstract 2
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 1
- 229920002472 Starch Polymers 0.000 abstract 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 1
- LOPVAWVHGAWUPS-UHFFFAOYSA-M [2-hydroxy-3-(2-methylprop-2-enoyloxy)propyl]-trimethylazanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC(O)C[N+](C)(C)C LOPVAWVHGAWUPS-UHFFFAOYSA-M 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 230000003385 bacteriostatic effect Effects 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 238000005189 flocculation Methods 0.000 abstract 1
- 230000016615 flocculation Effects 0.000 abstract 1
- 239000003999 initiator Substances 0.000 abstract 1
- 238000005342 ion exchange Methods 0.000 abstract 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 abstract 1
- 238000005956 quaternization reaction Methods 0.000 abstract 1
- 235000019698 starch Nutrition 0.000 abstract 1
- 239000008107 starch Substances 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
- 229920001567 vinyl ester resin Polymers 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/16—Anti-static materials
-
- 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
- C08F20/00—Homopolymers and 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
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Quaternary ammonium acrylic esters of the formula <FORM:1112912/C3/1> wherein R is hydrogen or C1- 3 alkyl, R1, R2 and R3 each represent C1- 18 alkyl, phenyl or C7- 24 aralkyl or hydrocarbon-substituted aralkyl, and X represents an anion, are polymerized alone or with at least one ethylenically unsaturated copolymerizable compound in the presence of an initiator such as azodiisobutyronitrile and, if desired, in the presence of cellulosic materials such as starch, paper and cotton; the cellulosic material may be immersed in an aqueous or non-aqueous solution or dispersion of the monomer. Suitable comonomers include acrylate, methacrylate, itaconate, maleate and fumarate esters, vinyl esters and ethers, amides and nitriles of (meth)acrylic acid, vinyltoluene, vinyl-naphthalene, styrene and vinyl chloride. In an example 3-methacryloxy-2-hydroxypropyl - trimethylammonium chloride is homopolymerized in dimethylformamide using azodiisobutyronitrile as a catalyst.ALSO:Novel quaternary ammonium esters of the formula <FORM:1112912/C2/1> wherein R is hydrogen or C1- 3 alkyl, R1, R2 and R3 each represent C1- 18 alkyl, phenyl or C7- 24 aralkyl or hydrocarbon-substituted aralkyl, and X represents an anion, are prepared by reacting an acid CH2 = C(R)COOH with an epihalohydrin and a tertiary amine R1R2R3N or, alternatively, by reacting an alkali metal salt of an acid CH2 = C(R)COOH with a chlorohydroxypropyl quaternary ammonium salt of the formula <FORM:1112912/C2/2> or with a tertiary amine of the formula <FORM:1112912/C2/3> followed by quaternization with R3X. The anion X may be exchanged for other anions by ion exchange treatment. The above compounds have bacteriostatic, bactericidal, anti-static and flocculation properties. The monomers may be homo- or co-polymerized, if desired in the presence of cellulosic materials.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39403664A | 1964-09-02 | 1964-09-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1112912A true GB1112912A (en) | 1968-05-08 |
Family
ID=23557289
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3653065A Expired GB1112912A (en) | 1964-09-02 | 1965-08-25 | Monomers with hydroxyl and quaternary ammonium functionality and polymers thereof |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE668940A (en) |
| DE (1) | DE1468931A1 (en) |
| GB (1) | GB1112912A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK154423B (en) * | 1969-10-20 | 1988-11-14 | Kendall & Co | QUATERNES AMMONIUM COMPOUND FOR SIMILAR USE AS EMULSION STABILIZER AND AS COMONOMS BY EMULSION POLYMERIZATION OF ETHYLENIC Saturated MONOMERS |
| US5008444A (en) * | 1988-11-30 | 1991-04-16 | Polypure, Inc. | Process for the production of substituted acryloyloxyhydroxypropyltrialkylammonium chloride |
| US5132383A (en) * | 1988-11-30 | 1992-07-21 | Polypure, Inc. | Copolymers of 3-methacryloyloxy-2-hydroxypropyl trimethylammonium chloride monomer and vinyl monomer |
| EP0537774A1 (en) * | 1991-10-18 | 1993-04-21 | Kuraray Co., Ltd. | Antimicrobial polymerizable composition, the polymer and article obtained from the same |
| CN106866438A (en) * | 2017-01-16 | 2017-06-20 | 淮海工学院 | A kind of acrylate functional monomer and preparation method thereof |
| CN107746446A (en) * | 2016-10-14 | 2018-03-02 | 中国石油大学(华东) | A kind of preparation method of ternary polymerization amphiprotic polyacrylamide |
| CN107746378A (en) * | 2016-10-14 | 2018-03-02 | 中国石油大学(华东) | A kind of polymerizable quaternaries cation monomer and preparation method thereof |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1593421C3 (en) * | 1966-08-29 | 1981-10-15 | Shell Internationale Research Maatschappij B.V., 2596 's-Gravenhage | Process for the preparation of cationic ester compounds |
| CN116655149B (en) * | 2023-06-02 | 2024-08-09 | 浙江鸿盛化工有限公司 | Decoloring and filtering method for phenol-containing wastewater for preparing m-aminophenol |
-
1965
- 1965-08-25 GB GB3653065A patent/GB1112912A/en not_active Expired
- 1965-08-30 BE BE668940A patent/BE668940A/xx unknown
- 1965-09-01 DE DE1965R0041454 patent/DE1468931A1/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK154423B (en) * | 1969-10-20 | 1988-11-14 | Kendall & Co | QUATERNES AMMONIUM COMPOUND FOR SIMILAR USE AS EMULSION STABILIZER AND AS COMONOMS BY EMULSION POLYMERIZATION OF ETHYLENIC Saturated MONOMERS |
| US5008444A (en) * | 1988-11-30 | 1991-04-16 | Polypure, Inc. | Process for the production of substituted acryloyloxyhydroxypropyltrialkylammonium chloride |
| US5132383A (en) * | 1988-11-30 | 1992-07-21 | Polypure, Inc. | Copolymers of 3-methacryloyloxy-2-hydroxypropyl trimethylammonium chloride monomer and vinyl monomer |
| EP0537774A1 (en) * | 1991-10-18 | 1993-04-21 | Kuraray Co., Ltd. | Antimicrobial polymerizable composition, the polymer and article obtained from the same |
| CN107746446A (en) * | 2016-10-14 | 2018-03-02 | 中国石油大学(华东) | A kind of preparation method of ternary polymerization amphiprotic polyacrylamide |
| CN107746378A (en) * | 2016-10-14 | 2018-03-02 | 中国石油大学(华东) | A kind of polymerizable quaternaries cation monomer and preparation method thereof |
| CN106866438A (en) * | 2017-01-16 | 2017-06-20 | 淮海工学院 | A kind of acrylate functional monomer and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1468931A1 (en) | 1969-01-02 |
| BE668940A (en) | 1966-02-28 |
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