GB973568A - Dispersions of acid-containing polymeric resins - Google Patents
Dispersions of acid-containing polymeric resinsInfo
- Publication number
- GB973568A GB973568A GB501261A GB501261A GB973568A GB 973568 A GB973568 A GB 973568A GB 501261 A GB501261 A GB 501261A GB 501261 A GB501261 A GB 501261A GB 973568 A GB973568 A GB 973568A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acrylic acid
- styrene
- copolymer
- ethyl acrylate
- water
- 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
- 239000006185 dispersion Substances 0.000 title abstract 5
- 239000002253 acid Substances 0.000 title abstract 4
- 239000002952 polymeric resin Substances 0.000 title 1
- 229920003002 synthetic resin Polymers 0.000 title 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 14
- 229920001577 copolymer Polymers 0.000 abstract 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 8
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical class CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 abstract 7
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 abstract 6
- 229910021529 ammonia Inorganic materials 0.000 abstract 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 abstract 3
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 abstract 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract 3
- 235000011118 potassium hydroxide Nutrition 0.000 abstract 3
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 3
- 239000000243 solution Substances 0.000 abstract 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 229920001807 Urea-formaldehyde Polymers 0.000 abstract 2
- 229920003180 amino resin Polymers 0.000 abstract 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 2
- 239000007859 condensation product Substances 0.000 abstract 2
- 238000010790 dilution Methods 0.000 abstract 2
- 239000012895 dilution Substances 0.000 abstract 2
- 239000003822 epoxy resin Substances 0.000 abstract 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 238000006386 neutralization reaction Methods 0.000 abstract 2
- 239000000049 pigment Substances 0.000 abstract 2
- 229920000647 polyepoxide Polymers 0.000 abstract 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 abstract 2
- 239000004408 titanium dioxide Substances 0.000 abstract 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000008199 coating composition Substances 0.000 abstract 1
- 238000007334 copolymerization reaction Methods 0.000 abstract 1
- XPNLOZNCOBKRNJ-UHFFFAOYSA-N ethyl prop-2-enoate;methyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C=C.COC(=O)C(C)=C XPNLOZNCOBKRNJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical class OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 abstract 1
- 125000005395 methacrylic acid group Chemical group 0.000 abstract 1
- BJILKNCQJSRBMC-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;prop-2-enamide Chemical compound NC(=O)C=C.COC(=O)C(C)=C BJILKNCQJSRBMC-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 229940072033 potash Drugs 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000005507 spraying Methods 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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D157/00—Coating compositions based on unspecified polymers obtained by reactions only involving carbon-to-carbon unsaturated 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
- 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
- C08F20/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives thereof
-
- 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
- C08F22/00—Homopolymers and 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 carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/44—Preparation of metal salts or ammonium salts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Paints Or Removers (AREA)
- Paper (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Aqueous polymer dispersions are made by preforming a copolymer including at least 4% by weight of unsaturated carboxylic acid and having a Water Dilution Value (ml. of water required to produce cloudiness in a defined solution of copolymer) between 50 and 400, neutralizing between 25 and 90% of the acid groups in the copolymer, and dispersing the neutralized product in water. Specified acids are acrylic, methacrylic, crotonic, maleic, fumaric, crotonic and itaconic acids. Specified co-monomers are styrene, vinyl toluene, methyl and ethyl acrylates, methyl methacrylate acrylamide and acrylonitrile. The neutralization of the copolymers may be effected by caustic soda or potash, ammonia or amines, e.g. diethylamine and triethylamine. The resulting dispersions are used as coating compositions and may have added thereto pigments, e.g. titanium dioxide, epoxy resins, e.g. a condensation product of epichlorohydrin and diphenylol propane, and aminoplasts, e.g. a water-soluble urea-form-aldehyde resin. The examples describe the copolymerization in solution in ethanol or isopropanol of: (a) styrene, ethyl acrylate and acrylic acid; (b) styrene, ethyl acrylate, acrylamide and acrylic acid; (c) methyl methacrylate and methacrylic acid; (d) methyl methacrylate and acrylic acid; (e) vinyl toluene, ethyl acrylate and acrylic acid; and (f) styrene, methyl methacrylate ethyl acrylate, acrylic acid and, optionally, acrylamide, and the neutralization of the copolymers with ammonia, triethylamine, diethylamine, caustic soda and caustic potash. The neutralized copolymers may be hydroxy-ethylated or hydroxybutylated by treatment with ethylene oxide or butylene oxide.ALSO:Metal panels are coated by applying thereto aqueous dispersions of copolymers including at least 4% by weight of unsaturated carboxylic acid and having a Water Dilution Value (ml. of water required to produce cloudiness in a defined solution of copolymer) of between 50 and 400, between 25 and 90% of the acid groups in the copolymer having been neutralized by an organic or inorganic base (see Division C3). Other ingredients of the dispersions are pigments, solvents, aminoplasts and epoxy resins. In the examples metal panels are coated by spraying with aqueous compositions containing: (1) a copolymer of styrene, ethyl acrylate and acrylic acid neutralized with ammonia and hydroxybutylated with butylene oxide, a water-soluble urea-formaldehyde resin and ethanol; (2) a copolymer of styrene, ethyl acrylate, acrylic acid and acrylamide neutralized with ammonia, isopropanol, titanium dioxide and a water-soluble urea-formaldehyde resin and/or a condensation product of epichlorohydrin and diphenylol propane; and (3) copolymers of styrene, ethyl acrylate and acrylic acid which have been hydroxyethylated with ethylene oxide and neutralized with ammonia, diethylamine, triethylamine, caustic soda and caustic potash.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA792948 | 1960-02-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB973568A true GB973568A (en) | 1964-10-28 |
Family
ID=4141180
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB501261A Expired GB973568A (en) | 1960-02-20 | 1961-02-10 | Dispersions of acid-containing polymeric resins |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE600402A (en) |
| CA (1) | CA676155A (en) |
| DE (1) | DE1233603B (en) |
| GB (1) | GB973568A (en) |
| IT (1) | IT647987A (en) |
| NL (1) | NL261456A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4840985A (en) * | 1982-08-06 | 1989-06-20 | Coatex, S. A. | Grinding agent based and/or copolymers for aqueous suspension of coarse mineral materials for pigment applications |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3532613A (en) * | 1963-08-14 | 1970-10-06 | Ford Motor Co | Electrocoating process |
| US3434993A (en) * | 1964-11-16 | 1969-03-25 | Allied Chem | Aqueous emulsion of emulsifiable oxidized polyethylene |
| US4020219A (en) * | 1971-04-02 | 1977-04-26 | Rohm And Haas Company | Metal decorating method involving mechanical shaping |
| US4007306A (en) * | 1974-11-26 | 1977-02-08 | Inmont Corporation | Method of applying aqueous coating compositions |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE862956C (en) * | 1941-10-30 | 1953-01-15 | Basf Ag | Process for the production of copolymers |
-
0
- BE BE600402D patent/BE600402A/xx unknown
- NL NL261456D patent/NL261456A/xx unknown
- CA CA676155A patent/CA676155A/en not_active Expired
- IT IT647987D patent/IT647987A/it unknown
-
1961
- 1961-02-10 GB GB501261A patent/GB973568A/en not_active Expired
- 1961-02-17 DE DE1961C0023425 patent/DE1233603B/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4840985A (en) * | 1982-08-06 | 1989-06-20 | Coatex, S. A. | Grinding agent based and/or copolymers for aqueous suspension of coarse mineral materials for pigment applications |
Also Published As
| Publication number | Publication date |
|---|---|
| NL261456A (en) | |
| CA676155A (en) | 1963-12-17 |
| IT647987A (en) | |
| BE600402A (en) | |
| DE1233603B (en) | 1967-02-02 |
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