GB801411A - Improvements in the properties of aqueous emulsions and dispersions - Google Patents
Improvements in the properties of aqueous emulsions and dispersionsInfo
- Publication number
- GB801411A GB801411A GB19849/56A GB1984956A GB801411A GB 801411 A GB801411 A GB 801411A GB 19849/56 A GB19849/56 A GB 19849/56A GB 1984956 A GB1984956 A GB 1984956A GB 801411 A GB801411 A GB 801411A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methacrylamide
- potassium persulphate
- vinyl
- added
- polymerized
- 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
- 239000000839 emulsion Substances 0.000 title abstract 2
- 239000004159 Potassium persulphate Substances 0.000 abstract 11
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 abstract 11
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 abstract 11
- 235000019394 potassium persulphate Nutrition 0.000 abstract 11
- 239000000203 mixture Substances 0.000 abstract 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 abstract 6
- 238000006116 polymerization reaction Methods 0.000 abstract 6
- 239000012736 aqueous medium Substances 0.000 abstract 5
- 229920001577 copolymer Polymers 0.000 abstract 5
- 238000010438 heat treatment Methods 0.000 abstract 5
- 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 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 abstract 4
- 239000007795 chemical reaction product Substances 0.000 abstract 4
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 abstract 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 abstract 3
- 239000007859 condensation product Substances 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- BSSNZUFKXJJCBG-OWOJBTEDSA-N (e)-but-2-enediamide Chemical compound NC(=O)\C=C\C(N)=O BSSNZUFKXJJCBG-OWOJBTEDSA-N 0.000 abstract 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 2
- -1 acrylic ureas Chemical class 0.000 abstract 2
- 235000013877 carbamide Nutrition 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- SWPMNMYLORDLJE-UHFFFAOYSA-N n-ethylprop-2-enamide Chemical group CCNC(=O)C=C SWPMNMYLORDLJE-UHFFFAOYSA-N 0.000 abstract 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 2
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 abstract 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 abstract 1
- YBXYCBGDIALKAK-UHFFFAOYSA-N 2-chloroprop-2-enamide Chemical compound NC(=O)C(Cl)=C YBXYCBGDIALKAK-UHFFFAOYSA-N 0.000 abstract 1
- CMPLVXYOKPNUAI-UHFFFAOYSA-N 2-hydroperoxycyclohexan-1-one Chemical compound OOC1CCCCC1=O CMPLVXYOKPNUAI-UHFFFAOYSA-N 0.000 abstract 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 abstract 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 abstract 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-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
- 239000005642 Oleic acid Substances 0.000 abstract 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- 239000004372 Polyvinyl alcohol Substances 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- BCBHWVAFKCCWBG-UHFFFAOYSA-N chloroethene;ethenyl propanoate Chemical compound ClC=C.CCC(=O)OC=C BCBHWVAFKCCWBG-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 235000011187 glycerol Nutrition 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 150000003951 lactams Chemical class 0.000 abstract 1
- 239000000944 linseed oil Substances 0.000 abstract 1
- 235000021388 linseed oil Nutrition 0.000 abstract 1
- 125000005395 methacrylic acid group Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000012170 montan wax Substances 0.000 abstract 1
- OVHHHVAVHBHXAK-UHFFFAOYSA-N n,n-diethylprop-2-enamide Chemical compound CCN(CC)C(=O)C=C OVHHHVAVHBHXAK-UHFFFAOYSA-N 0.000 abstract 1
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 abstract 1
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 abstract 1
- CNPHCSFIDKZQAK-UHFFFAOYSA-N n-prop-2-enylprop-2-enamide Chemical compound C=CCNC(=O)C=C CNPHCSFIDKZQAK-UHFFFAOYSA-N 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 235000019198 oils Nutrition 0.000 abstract 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 1
- 239000004006 olive oil Substances 0.000 abstract 1
- 235000008390 olive oil Nutrition 0.000 abstract 1
- 239000000049 pigment Substances 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 229920002451 polyvinyl alcohol Polymers 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 150000005846 sugar alcohols Polymers 0.000 abstract 1
- 229920003002 synthetic resin Polymers 0.000 abstract 1
- 239000000057 synthetic resin Substances 0.000 abstract 1
- 239000004408 titanium dioxide Substances 0.000 abstract 1
- 229920001567 vinyl ester resin Polymers 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- 239000001993 wax Substances 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
- 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
-
- 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
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
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)
- Colloid Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Paper (AREA)
Abstract
The properties of water-containing dispersions or emulsions of substances which are not polymerizable and not miscible with water are improved by adding thereto a polymerizable ethylenically unsaturated carboxylic acid amide which is then polymerized. Unsaturated amides specified are acrylamide, methacrylamide, N-ethyl- and N,N-diethyl-acrylamide, N-methylolacrylamide and methacrylamide, N-hydroxyethylacrylamide, alpha-chloracrylamide, allylacrylamide, acrylic ureas and fumaric diamide and mixtures thereof; also present during polymerization may be other ethylenically unsaturated compounds such as unsaturated mono- or di-carboxylic acids, e.g. acrylic acid, and their salts, esters and nitriles, unsaturated alcohols and their esters and vinyl ethers, halides and lactams. The polymerization is carried out with the aid of catalysts such as hydrogen peroxide, potassium persulphate, acetyl peroxide, cyclohexanone hydroperoxide, azo-bis-isobutyronitrile, a potassium persulphate/sodium hydrosulphite redox system or ultra-violet light. The process may be applied to dispersions of waxes, pigments and synthetic resins, e.g. polyamides, urea/aldehyde condensation products, condensation products of polycarboxylic acids, polyalcohols and unsaturated oils and polymers of vinyl esters and ketones, vinyl and vinylidene halides, acrylic and methacrylic esters, N-vinyl compounds and C-vinyl compounds. In examples: (1) vinyl propionate is polymerized in an aqueous medium containing a methacrylamide/vinyl pyrrolidone copolymer and the reaction product of ethylene oxide and octadecyl alcohol in the presence of potassium persulphate, at the end of polymerization acrylamide is added and heating continued for four hours, after cooling titanium dioxide may be added to the dispersion; (2) a mixture of vinyl propionate vinyl-chloride and butyl acrylate is polymerized in an aqueous medium containing a saponified acrylonitrile/methyl acrylate copolymer and the reaction product of ethylene oxide and octadecyl alcohol in the presence of potassium persulphate, at the end of polymerization methacrylamide and a further quantity of potassium persulphate are added and heating continued for six hours; (3) vinyl propionate is polymerized in an aqueous medium containing polyvinyl alcohol in the presence of potassium persulphate, at the end of polymerization a mixture of acrylamide, methacrylamide and N-methylolmethacrylamide is added, together with azo-bis-isobutyronitrile, and then polymerized; (4) vinyl propionate is polymerized in an aqueous medium containing a vinyl pyrrolidone/methacrylamide copolymer, to the resulting dispersion there is added a mixture of methacrylamide, N-ethylacrylamide and potassium persulphate and heating is continued for six hours; (5) as in (4) but using a mixture of methacrylamide and fumaric diamide and a potassium persulphate/sodium hydrosulphite catalyst mixture; (6) olive oil or montan wax is emulsified in water containing a methacrylamide/vinyl pyrrolidone copolymer and there is added thereto methacrylamide, potassium persulphate and an oleic acid/ethylene oxide reaction product, followed by heating for five hours; (7) as in (6) but in which there is emuslified a condensation product of phthalic acid, glycerine and linseed oil and in which there is added with the methacrylamide an octadecyl alcohol/ethylene oxide reaction product; (8) a mixture of methyl acrylate and vinyl propionate is polymerized in an aqueous medium containing a saponified acrylonitrile/methyl acrylate copolymer in the presence of potassium persulphate, after polymerization there is added a mixture of methacrylamide, acrylic acid and potassium persulphate and heating is continued for four hours.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB36301A DE1040565B (en) | 1955-06-29 | 1955-06-29 | Process for the preparation of aqueous or water-containing emulsions and dispersions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB801411A true GB801411A (en) | 1958-09-10 |
Family
ID=6964845
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB19849/56A Expired GB801411A (en) | 1955-06-29 | 1956-06-27 | Improvements in the properties of aqueous emulsions and dispersions |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1040565B (en) |
| FR (1) | FR1154044A (en) |
| GB (1) | GB801411A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3177146A (en) * | 1961-10-17 | 1965-04-06 | Shell Oil Co | Fire-resistant hydraulic fluids |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1242858B (en) * | 1965-04-09 | 1967-06-22 | Basf Ag | Process for preparing polyamide dispersions |
| NL7610147A (en) * | 1975-09-18 | 1977-03-22 | Cassella Farbwerke Mainkur Ag | PROCESS FOR THE PREPARATION OF COPOLYMERS SOLUBLE IN COLD WATER. |
| DE3148785A1 (en) * | 1981-03-31 | 1983-02-10 | Showa Denko K.K., Tokyo | BINDERS FOR PAPER COATINGS |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE623404C (en) * | 1930-05-26 | |||
| BE452384A (en) * | 1942-10-05 | |||
| US2467192A (en) * | 1946-04-05 | 1949-04-12 | Du Pont | Coating compositions |
| US2458423A (en) * | 1947-11-22 | 1949-01-04 | Eastman Kodak Co | N-allyl derivatives of acrylic esteramides and polymers thereof |
| US2458420A (en) * | 1947-11-22 | 1949-01-04 | Eastman Kodak Co | Acrylic ester-amides and polymers thereof |
-
1955
- 1955-06-29 DE DEB36301A patent/DE1040565B/en active Pending
-
1956
- 1956-06-27 GB GB19849/56A patent/GB801411A/en not_active Expired
- 1956-06-29 FR FR1154044D patent/FR1154044A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3177146A (en) * | 1961-10-17 | 1965-04-06 | Shell Oil Co | Fire-resistant hydraulic fluids |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1040565B (en) | 1958-10-09 |
| FR1154044A (en) | 1958-04-01 |
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