GB831881A - Water-soluble copolymers derived from acrylamide, methacrylamide and acrylic acid esters - Google Patents
Water-soluble copolymers derived from acrylamide, methacrylamide and acrylic acid estersInfo
- Publication number
- GB831881A GB831881A GB856457A GB856457A GB831881A GB 831881 A GB831881 A GB 831881A GB 856457 A GB856457 A GB 856457A GB 856457 A GB856457 A GB 856457A GB 831881 A GB831881 A GB 831881A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methacrylamide
- acrylamide
- vinyl
- copolymer
- dispersed
- 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
- 229920001577 copolymer Polymers 0.000 title abstract 13
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 title abstract 12
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 title abstract 10
- 125000005396 acrylic acid ester group Chemical group 0.000 title 1
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 abstract 12
- 239000007864 aqueous solution Substances 0.000 abstract 7
- 239000000203 mixture Substances 0.000 abstract 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical class OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 4
- 239000000178 monomer Substances 0.000 abstract 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 3
- 239000007859 condensation product Substances 0.000 abstract 3
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 abstract 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 abstract 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- 239000004159 Potassium persulphate Substances 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 2
- MKUWVMRNQOOSAT-UHFFFAOYSA-N but-3-en-2-ol Chemical compound CC(O)C=C MKUWVMRNQOOSAT-UHFFFAOYSA-N 0.000 abstract 2
- 239000000084 colloidal system Substances 0.000 abstract 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 abstract 2
- 239000006185 dispersion Substances 0.000 abstract 2
- 239000003925 fat Substances 0.000 abstract 2
- 235000011187 glycerol Nutrition 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 239000000944 linseed oil Chemical class 0.000 abstract 2
- 235000021388 linseed oil Nutrition 0.000 abstract 2
- -1 methallyl alcohols Chemical class 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 239000003921 oil Substances 0.000 abstract 2
- 235000019198 oils Nutrition 0.000 abstract 2
- 239000004006 olive oil Substances 0.000 abstract 2
- 235000008390 olive oil Nutrition 0.000 abstract 2
- 239000012188 paraffin wax Substances 0.000 abstract 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 abstract 2
- 235000019394 potassium persulphate Nutrition 0.000 abstract 2
- 230000001681 protective effect Effects 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- 150000005846 sugar alcohols Polymers 0.000 abstract 2
- 239000001993 wax Substances 0.000 abstract 2
- 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 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- MXRGSJAOLKBZLU-UHFFFAOYSA-N 3-ethenylazepan-2-one Chemical compound C=CC1CCCCNC1=O MXRGSJAOLKBZLU-UHFFFAOYSA-N 0.000 abstract 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 abstract 1
- 239000000020 Nitrocellulose Substances 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical class C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 abstract 1
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 238000012674 dispersion polymerization Methods 0.000 abstract 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 abstract 1
- QJQZEJFUIOWFMS-UHFFFAOYSA-N formaldehyde;sulfanediol Chemical compound O=C.OSO QJQZEJFUIOWFMS-UHFFFAOYSA-N 0.000 abstract 1
- 239000001023 inorganic pigment Substances 0.000 abstract 1
- 125000005395 methacrylic acid group Chemical group 0.000 abstract 1
- 229920001220 nitrocellulos Polymers 0.000 abstract 1
- 239000012860 organic pigment Substances 0.000 abstract 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 abstract 1
- 239000000049 pigment Substances 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- 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
- C08F220/56—Acrylamide; Methacrylamide
-
- 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
- C08F20/52—Amides or imides
- C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F20/56—Acrylamide; Methacrylamide
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paper (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Aqueous dispersions of water-immiscible substances are prepared with the aid, as dispersing agents, of water-soluble copolymers of methyl and/or ethyl acrylate and acrylamide and methacrylamide which contain at least 8% and at most 50% of the acrylate esters and at most 92% of acrylamide and methacrylamide, the methacrylamide content being between 30 and 90% with reference to the total weight of acrylamide and methacrylamide. Substances which may be dispersed are oils, fats, waxes, hydrocarbons, nitrocellulose, condensation products of dicarboxylic acids and polyalcohols and organic and inorganic pigments. In examples: (7) paraffin wax is dispersed in an aqueous solution of a copolymer of methyl acrylate, methacrylamide, acrylamide and sodium vinyl sulphonate; (8) olive oil is dispersed in an aqueous solution of a copolymer of methyl acrylate, methacrylamide and acrylamide; and (9) a condensation product of phthalic acid, glycerine and linseed oil acids is dispersed in an aqueous solution of a copolymer as in (8).ALSO:Copolymers are made by homogeneously dissolving in water a mixture of monomers comprising 8 to 50% of methyl and/or ethyl acrylate and up to 92% of acrylamide and methacrylamide, the mixture of amides containing at least 30% and at most 90% of methacrylamide, and then polymerizing the monomer mixture which may optionally contain other polymerizable monomers such as acrylic, methacrylic and crotonic acids and their salts, acrolein, allyl and methallyl alcohols, methyl vinyl carbinol, N-vinyl pyrrolidone, vinyl caprolactam, sodium vinylsulphonate and N-methyl, N-ethyl, N-dimethyl and N-diethyl acrylamides. Polymerization may be carried out with the aid of catalysts such as hydrogen peroxide, acetyl peroxide; potassium persulphate, azo-di-isobutyronitrile and redox systems, e.g. a mixture of potassium persulphate and formaldehyde sulphoxylate; in addition, polymerization may be initiated by ultraviolet light. The copolymers are water-resistance of which may be improved by reaction with formaldehyde or condensate containing methylol groups; the copolymers are also used as protective colloids in the preparation of dispersions of oils, fats, waxes, hydrocarbons, acids and polyalcohols and pigments, and in the aqueous dispersion polymerization of monomers such as vinyl acetate and propionate, vinyl chloride, styrene, vinyl ketones and mono- and di-carboxylic acids and their derivatives. In examples of the protective colloid application of the copolymers: (5) vinyl propionate is polymerized by gradual addition to an aqueous solution of a copolymer of methyl acrylate, methacrylamide and acrylamide containing sodium persulphate, (6) a mixture of vinyl acetate and vinyl chloride is polymerized as in (5), (7) paraffin wax is dispersed in an aqueous solution of a copolymer of methyl acrylate, methacrylamide, acrylamide and sodium vinyl sulphonate, (8) olive oil is dispersed in an aqueous solution of a copolymer of methyl acrylate, methacrylamide and acrylamide, and (9) a condensation product of phthalic acid, glycerine and linseed oil acids is dispersed in an aqueous solution of a copolymer as in (8).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB39542A DE1037128B (en) | 1956-03-17 | 1956-03-17 | Process for the preparation of copolymers containing amide and ester groups which are soluble in water |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB831881A true GB831881A (en) | 1960-04-06 |
Family
ID=6965836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB856457A Expired GB831881A (en) | 1956-03-17 | 1957-03-15 | Water-soluble copolymers derived from acrylamide, methacrylamide and acrylic acid esters |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1037128B (en) |
| FR (1) | FR1173009A (en) |
| GB (1) | GB831881A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3673280A (en) * | 1967-06-14 | 1972-06-27 | Rohm & Haas | Elastomeric materials and process therefor |
| US4074039A (en) * | 1970-03-26 | 1978-02-14 | Ceskoslovenska Akademie Ved | Hydrophilic N,N-diethyl acrylamide copolymers |
| EP0066078A3 (en) * | 1981-06-01 | 1985-03-20 | American Cyanamid Company | Process for sizing textile materials |
| US4906716A (en) * | 1988-05-17 | 1990-03-06 | Exxon Chemical Patents Inc. | Method of incorporating hydrophobic monomers into acrylamide solutions |
| CN115572559A (en) * | 2022-03-15 | 2023-01-06 | 中国科学院福建物质结构研究所 | Anti-freezing optical cement and preparation method thereof |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1102410B (en) * | 1958-12-20 | 1961-03-16 | Roehm & Haas Gmbh | Process for the production of solvent-resistant, hardenable plastics which form a film from dispersions or solutions |
| DE1195050B (en) * | 1961-01-07 | 1965-06-16 | Basf Ag | Process for the production of water-soluble copolymers |
| DE1222611B (en) * | 1961-02-07 | 1966-08-11 | Basf Ag | Coating compounds hardening through the action of heat on the basis of aqueous solutions |
| CA1177589A (en) * | 1981-03-31 | 1984-11-06 | Eiichi Yoshida | Binder composition for paper-coating materials |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE697481C (en) * | 1936-05-29 | 1940-10-15 | I G Farbenindustrie Akt Ges | Process for the production of high molecular weight polymerisation products which are soluble in cold water |
-
1956
- 1956-03-17 DE DEB39542A patent/DE1037128B/en active Pending
-
1957
- 1957-03-15 FR FR1173009D patent/FR1173009A/en not_active Expired
- 1957-03-15 GB GB856457A patent/GB831881A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3673280A (en) * | 1967-06-14 | 1972-06-27 | Rohm & Haas | Elastomeric materials and process therefor |
| US4074039A (en) * | 1970-03-26 | 1978-02-14 | Ceskoslovenska Akademie Ved | Hydrophilic N,N-diethyl acrylamide copolymers |
| EP0066078A3 (en) * | 1981-06-01 | 1985-03-20 | American Cyanamid Company | Process for sizing textile materials |
| US4906716A (en) * | 1988-05-17 | 1990-03-06 | Exxon Chemical Patents Inc. | Method of incorporating hydrophobic monomers into acrylamide solutions |
| CN115572559A (en) * | 2022-03-15 | 2023-01-06 | 中国科学院福建物质结构研究所 | Anti-freezing optical cement and preparation method thereof |
| CN115572559B (en) * | 2022-03-15 | 2023-11-17 | 中国科学院福建物质结构研究所 | Anti-freezing optical cement and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1037128B (en) | 1958-08-21 |
| FR1173009A (en) | 1959-02-18 |
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