GB1003318A - Improvements in the manufacture of copolymers - Google Patents
Improvements in the manufacture of copolymersInfo
- Publication number
- GB1003318A GB1003318A GB30346/61A GB3034661A GB1003318A GB 1003318 A GB1003318 A GB 1003318A GB 30346/61 A GB30346/61 A GB 30346/61A GB 3034661 A GB3034661 A GB 3034661A GB 1003318 A GB1003318 A GB 1003318A
- Authority
- GB
- United Kingdom
- Prior art keywords
- copolymer
- ethyl acrylate
- methacrylic acid
- styrene
- preformed
- 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 18
- 238000004519 manufacturing process Methods 0.000 title 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 14
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 abstract 10
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 abstract 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 9
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 5
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 abstract 4
- 239000000839 emulsion Substances 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical class CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 229920000642 polymer Polymers 0.000 abstract 3
- 239000000243 solution Substances 0.000 abstract 3
- 239000004408 titanium dioxide Substances 0.000 abstract 3
- ZGHFDIIVVIFNPS-UHFFFAOYSA-N 3-Methyl-3-buten-2-one Chemical compound CC(=C)C(C)=O ZGHFDIIVVIFNPS-UHFFFAOYSA-N 0.000 abstract 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 2
- 229920000877 Melamine resin Polymers 0.000 abstract 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 239000002270 dispersing agent Substances 0.000 abstract 2
- 239000006185 dispersion Substances 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 239000000178 monomer Substances 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 239000002023 wood Substances 0.000 abstract 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 abstract 1
- SFPNZPQIIAJXGL-UHFFFAOYSA-N 2-ethoxyethyl 2-methylprop-2-enoate Chemical compound CCOCCOC(=O)C(C)=C SFPNZPQIIAJXGL-UHFFFAOYSA-N 0.000 abstract 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 abstract 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- 229910001209 Low-carbon steel Inorganic materials 0.000 abstract 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 abstract 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004159 Potassium persulphate Substances 0.000 abstract 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 abstract 1
- 239000004141 Sodium laurylsulphate Substances 0.000 abstract 1
- 229910000831 Steel Inorganic materials 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 230000001680 brushing effect Effects 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000008199 coating composition Substances 0.000 abstract 1
- 229960002887 deanol Drugs 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical class CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 abstract 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 abstract 1
- 229940117841 methacrylic acid copolymer Drugs 0.000 abstract 1
- 125000005395 methacrylic acid group Chemical group 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 239000003973 paint Substances 0.000 abstract 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 abstract 1
- 235000019394 potassium persulphate Nutrition 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- 150000003839 salts Chemical group 0.000 abstract 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 abstract 1
- HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 abstract 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 abstract 1
- 239000010959 steel Substances 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
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/003—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon 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
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paints Or Removers (AREA)
Abstract
Alkali-soluble copolymers are made by copolymerizing an acrylic or methacrylic ester with an unsaturated carboxylic acid to form an alkali-soluble copolymer in the presence of an aqueous solution or dispersion of a preformed alkali-soluble copolymer of an acrylic or methacrylic ester. The preformed copolymer has a composition which may or may not be the same as that of the copolymer subsequently formed. The copolymers are derived from esters such as methyl, ethyl, butyl and 2-ethylhexyl acrylates, or methyl and ethyl methacrylates, acids such as acrylic, methacrylic and itaconic acids, and, optionally, other monomers such as styrene, vinyl acetate, butadiene, isoprene, methyl iso propenyl ketone, allyl alcohol, hydroxyethyl acrylate, ethoxyethyl methacrylate, acrylamide, methacrylamide, methylol acrylamide and acrylonitrile. In the preparation of the preformed copolymer dispersing agents, e.g. sodium dodecyl benzene sulphonate, sodium naphthalene sulphonate/ formaldehyde condensate and sodium lauryl sulphate, are used, but in the second stage of polymerization no additional dispersing agent is used. Both stages of polymerization may be carried out with gradual addition of monomers and catalyst, e.g. potassium persulphate, to the reaction medium. The preformed copolymer may be used either in the free-acid or salt form. The examples describe the preparation of the following first stage copolymers (a), and second stage copolymers (G): (1) (a) and (b) ethyl acrylate / methyl methacrylate / methacrylic acid, (2) (a) and (b) ethyl acrylate/vinyl acetate/ methacrylic acid, (3) (a) and (b) ethyl acrylate/ styrene/methacrylic acid, and (4) (a) ethyl acrylate/styrene/methacrylic acid and (b) ethyl acrylate / styrene / 2 - ethylhexyl acrylate/ methacrylic acid. The polymer emulsion of (4) is formed into a coating composition by neutralization with dimethylaminoethanol, followed by the addition to the resulting polymer solution of titanium dioxide and a water-soluble melamine-formaldehyde resin.ALSO:Surfaces of wood and steel are coated by applying thereto an emulsion or solution of an alkali-soluble copolymer made by copolymerizing an acrylic or methacrylic ester with an unsaturated acid in the presence of an aqueous solution or dispersion of a preformed alkali-soluble copolymer of an acrylic or methacrylic ester, which preformed polymer may have the same composition as the copolymer subsequently formed (see Division C3). In Examples (1-3), wood boards primed with matt black paint are coated by brushing with emulsions containing titanium dioxide and first- and second-stage copolymers which are of identical composition and which are: (i) ethyl acrylate/methyl methacrylate/methacrylic acid, (ii) ethyl acrylate/vinyl acetate/methacrylic acid, and (iii) ethyl acrylate/ styrene/methacrylic acid. In Example (4) mild steel panels are coated with a composition comprising titanium dioxide, a water-soluble melamine-formaldehyde resin and a copolymer solution obtained by adding diethylaminoethanol to a copolymer emulsion containing an ethyl acrylate/styrene/methacrylic acid first-stage copolymer and an ethyl acrylate/styrene/2-ethylhexyl acrylate/methacrylic acid copolymer, and finally baked.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL282018D NL282018A (en) | 1961-08-23 | ||
| GB30346/61A GB1003318A (en) | 1961-08-23 | 1961-08-23 | Improvements in the manufacture of copolymers |
| DE19621495425 DE1495425A1 (en) | 1961-08-23 | 1962-08-22 | Process for the preparation of an alkali-soluble copolymer of an acrylic ester |
| FR907592A FR1335264A (en) | 1961-08-23 | 1962-08-23 | Improvements in the manufacture of copolymers, in particular acrylic copolymers |
| GB975264A GB1083184A (en) | 1961-08-23 | 1964-03-07 | Improvements in and relating to coating compositions |
| NL6502810A NL6502810A (en) | 1961-08-23 | 1965-03-05 | |
| FR8042A FR87480E (en) | 1961-08-23 | 1965-03-05 | Improvements in the manufacture of copolymers, in particular acrylic copolymers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB30346/61A GB1003318A (en) | 1961-08-23 | 1961-08-23 | Improvements in the manufacture of copolymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1003318A true GB1003318A (en) | 1965-09-02 |
Family
ID=10306188
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB30346/61A Expired GB1003318A (en) | 1961-08-23 | 1961-08-23 | Improvements in the manufacture of copolymers |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE1495425A1 (en) |
| FR (1) | FR1335264A (en) |
| GB (1) | GB1003318A (en) |
| NL (1) | NL282018A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5070164A (en) * | 1987-07-02 | 1991-12-03 | Mobil Oil Corporation | Cold sealable cohesive terpolymers |
| US5567773A (en) * | 1995-04-04 | 1996-10-22 | Mobil Oil Corporation | Cold sealable cohesive polymers |
| US6077602A (en) * | 1996-03-21 | 2000-06-20 | Mobil Oil Corporation | Heat sealable film |
| US6802673B1 (en) | 1999-08-12 | 2004-10-12 | Mbt Holding Ag | Tunnel boring with foamed composition |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO141367C (en) * | 1976-11-22 | 1980-02-27 | Sintef | PROCEDURE FOR THE PREPARATION OF FINALLY SHARED EMULSIONS OF A LITTLE WATER-SOLUBLE MATERIAL |
-
0
- NL NL282018D patent/NL282018A/xx unknown
-
1961
- 1961-08-23 GB GB30346/61A patent/GB1003318A/en not_active Expired
-
1962
- 1962-08-22 DE DE19621495425 patent/DE1495425A1/en active Pending
- 1962-08-23 FR FR907592A patent/FR1335264A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5070164A (en) * | 1987-07-02 | 1991-12-03 | Mobil Oil Corporation | Cold sealable cohesive terpolymers |
| US5567773A (en) * | 1995-04-04 | 1996-10-22 | Mobil Oil Corporation | Cold sealable cohesive polymers |
| US6077602A (en) * | 1996-03-21 | 2000-06-20 | Mobil Oil Corporation | Heat sealable film |
| US6802673B1 (en) | 1999-08-12 | 2004-10-12 | Mbt Holding Ag | Tunnel boring with foamed composition |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1495425A1 (en) | 1969-02-06 |
| NL282018A (en) | |
| FR1335264A (en) | 1963-08-16 |
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