GB1121418A - Copolymeric coating compositions - Google Patents
Copolymeric coating compositionsInfo
- Publication number
- GB1121418A GB1121418A GB3038967A GB3038967A GB1121418A GB 1121418 A GB1121418 A GB 1121418A GB 3038967 A GB3038967 A GB 3038967A GB 3038967 A GB3038967 A GB 3038967A GB 1121418 A GB1121418 A GB 1121418A
- Authority
- GB
- United Kingdom
- Prior art keywords
- copolymer
- methyl
- oxazolone
- vinyl
- acid
- 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 15
- 239000008199 coating composition Substances 0.000 title abstract 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 6
- 229920002554 vinyl polymer Polymers 0.000 abstract 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexamethylene diamine Natural products NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 abstract 3
- 239000000178 monomer Substances 0.000 abstract 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 abstract 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 abstract 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 abstract 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 abstract 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 abstract 2
- -1 N-substituted amides Chemical class 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 abstract 2
- 238000004132 cross linking Methods 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 150000002825 nitriles Chemical class 0.000 abstract 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 2
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 abstract 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 abstract 1
- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 abstract 1
- IEJPPSMHUUQABK-UHFFFAOYSA-N 2,4-diphenyl-4h-1,3-oxazol-5-one Chemical compound O=C1OC(C=2C=CC=CC=2)=NC1C1=CC=CC=C1 IEJPPSMHUUQABK-UHFFFAOYSA-N 0.000 abstract 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- MKIAUMDWNFQZPL-UHFFFAOYSA-N C(CCCCCC(C)C)C1=C(C=CC=C1)O.C1CO1 Chemical compound C(CCCCCC(C)C)C1=C(C=CC=C1)O.C1CO1 MKIAUMDWNFQZPL-UHFFFAOYSA-N 0.000 abstract 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 1
- 239000002202 Polyethylene glycol Substances 0.000 abstract 1
- 229920002873 Polyethylenimine Polymers 0.000 abstract 1
- 239000004372 Polyvinyl alcohol Substances 0.000 abstract 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000003431 cross linking reagent Substances 0.000 abstract 1
- 125000004367 cycloalkylaryl group Chemical group 0.000 abstract 1
- IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 239000003822 epoxy resin Substances 0.000 abstract 1
- GPQWKLDEDGOJQH-UHFFFAOYSA-N ethane-1,1,1,2-tetramine Chemical compound NCC(N)(N)N GPQWKLDEDGOJQH-UHFFFAOYSA-N 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 abstract 1
- 125000005395 methacrylic acid group Chemical class 0.000 abstract 1
- WFKDPJRCBCBQNT-UHFFFAOYSA-N n,2-dimethylprop-2-enamide Chemical compound CNC(=O)C(C)=C WFKDPJRCBCBQNT-UHFFFAOYSA-N 0.000 abstract 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 abstract 1
- LGYJSPMYALQHBL-UHFFFAOYSA-N pentanedihydrazide Chemical compound NNC(=O)CCCC(=O)NN LGYJSPMYALQHBL-UHFFFAOYSA-N 0.000 abstract 1
- 235000011007 phosphoric acid Nutrition 0.000 abstract 1
- 229920000647 polyepoxide Polymers 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 229920001223 polyethylene glycol Polymers 0.000 abstract 1
- 229920002451 polyvinyl alcohol Polymers 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 150000003440 styrenes Chemical class 0.000 abstract 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 abstract 1
- 229920001567 vinyl ester resin Polymers 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
- C09D157/04—Copolymers in which only the monomer in minority is defined
-
- 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
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
-
- 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
- C09D125/00—Coating compositions based on homopolymers or 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 an aromatic carbocyclic ring; Coating compositions based on derivatives of such polymers
- C09D125/02—Homopolymers or copolymers of hydrocarbons
- C09D125/04—Homopolymers or copolymers of styrene
- C09D125/08—Copolymers of styrene
- C09D125/14—Copolymers of styrene with unsaturated esters
-
- 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
- C09D133/00—Coating compositions based on homopolymers or 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/062—Copolymers with monomers not covered by C09D133/06
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
A copolymer is derived from a monomer mixture containing at least 50% by weight of acrylic and/or methacrylic acid esters, from 0.5 to 30% of an azlactone of formula <FORM:1121418/C3/1> (in which R1 and R2 represent alkyl, cycloalkyl aryl or aralkyl groups, or R1 and R2 together with the adjacent carbon atom represent a carbocyclic or heterocyclic ring system, and R3 represents a group containing a polymerizable carbon-carbon double bond), and, if desired, up to 49.5% of one or more further comonomers. Specified comonomers are acrylic and methacrylic acids, nitriles, amides, or N-substituted amides thereof, styrenes, vinyl esters and olefins. The copolymers may be cross-linked with a compound containing a primary or secondary amino group, or a hydroxyl, mercapto and/or hydrazide group, e.g. ethylene diamine, triaminoethylamine, N,N1-di - (tert. - butylhdroxycarbonyl) - hexamethylenediamine, N - aminoethylpiperazine, ethylene glycol, butanediol, glycerol, dimercaptoethane, ethanolamine, glutaric acid dihydrazide, polyethylene glycol, polyvinyl alcohol, polyethyleneimine, an epoxy resin or a polyester. Alternatively, the copolymer may contain functional groups capable of interacting to effect cross-linking, e.g. when b -hydroxyethyl methacrylate is one of the monomers. Cross-linking catalysts such as H3PO4 or a sodium alcoholate may be used, for instance when the composition is employed as a coating composition. In Examples 1 to 8 the copolymers are produced in solution in one or more solvents selected from ethyl acetate, methyl ethyl ketone and ethyl glycol acetate, the catalyst (azoisobutyric acid nitrile or dilauroyl peroxide) being added in two stages and the cross-linking agents being ethylene diamine, hexamethylene diamine, butanediol, adipic acid dihydrazide and p-toluene sulphonic acid, or a vinyl acetate-vinyl alcohol copolymer and said acid, or trichloroacetic acid. The copolymers are as follows: Examples 1 and 8, an ethyl acrylate, methyl methacrylate, 2-isopropenyl - 4,4-dimethyl oxazolone-5 copolymer; Example 2, a n-butyl acrylate, acrylonitrile, methyl methacrylate, styrene, 2-isopropenyl-4-methyl-4-n-propyl oxazolone-5 copolymer; Example 3, a n-butyl methacrylate, N-methyl methacrylamide, 2 - vinyl - 4,4 - pentamethylene - oxazolone-5 copolymer; Example 4, a 2-ethylhexyl acrylate, methyl methacrylate, methacrylic acid, 2 - vinyl - 4 - methyl - 4 - phenyl - oxazolone-5 copolymer; Example 5, a methyl acrylate, vinyl acetate, diethyl fumarate, 2 - vinyl - 4 - methyl - 4 - benzyl - oxazolone - 5 copolymer; Example 6, a 2-ethylhexyl acrylate, methyl methacrylate, 2-hydroxyethyl methacrylate, 2 - acryloxyethyl - 4 - methyl - 4 - cyclohexyl - oxazolone-5 copolymer, and Example 7, an ethyl acrylate, methyl methacrylate, methacrylic acid, 2-isopropenyl-4,4-dimethyloxazolone - 5 copolymer. In Example 9, a copolymer of ethyl acrylate, methyl methacrylate and 2-isopropenyl-4,4-dimethyloxazolone-5 is produced in an aqueous emulsion containing an ethylene oxide-isononyl phenol condensate as emulsifier and the sodium salt of 4,41 - dicyano - 4,41 - azodivaleric acid as catalyst. Other oxazolone monomers specified are 2 - isopropenyl - 4,4 - di - n - propyl - oxazolone - 5 and 2 - vinyl - 4 - methyl - 4 - benzyl-oxazolone-5.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1966R0043605 DE1645214B2 (en) | 1966-07-01 | 1966-07-01 | Process for the production of crosslinking coating agents |
| DE1967R0045886 DE1745330A1 (en) | 1966-07-01 | 1967-04-27 | Process for the production of crosslinking coating compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1121418A true GB1121418A (en) | 1968-07-24 |
Family
ID=25991987
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3038967A Expired GB1121418A (en) | 1966-07-01 | 1967-06-30 | Copolymeric coating compositions |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1745330A1 (en) |
| GB (1) | GB1121418A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4288523A (en) | 1980-03-14 | 1981-09-08 | Polaroid Corporation | Diffusion control layers in diffusion transfer photographic products |
| WO1982003131A1 (en) * | 1981-03-02 | 1982-09-16 | Corp Polaroid | Cleavable polymers and photographic products and processes employing same |
| US4546159A (en) * | 1980-03-14 | 1985-10-08 | Polaroid Corporation | Eliminating polymers useful in diffusion control layers |
| US4619867A (en) * | 1983-06-14 | 1986-10-28 | Minnesota Mining And Manufacturing Company | Azlactone-containing pressure-sensitive adhesives |
| US4639286A (en) * | 1982-09-27 | 1987-01-27 | Minnesota Mining And Manufacturing Company | Curable compositions containing azlactone-functional compounds |
| US4695608A (en) * | 1984-03-29 | 1987-09-22 | Minnesota Mining And Manufacturing Company | Continuous process for making polymers having pendant azlactone or macromolecular moieties |
| US4699843A (en) * | 1983-06-14 | 1987-10-13 | Minnesota Mining And Manufacturing Company | Azlactone-containing pressure-sensitive adhesives |
| US4981933A (en) * | 1989-06-23 | 1991-01-01 | Polaroid Corporation | Azlactone copolymers |
| US5523080A (en) * | 1993-05-18 | 1996-06-04 | Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. | Cosmetic treatment of substrates |
| CN100500994C (en) * | 2006-10-23 | 2009-06-17 | 上海东升新材料有限公司 | Method for preparing aqueous base material for treating vacuum aluminum plated paper |
-
1967
- 1967-04-27 DE DE1967R0045886 patent/DE1745330A1/en active Pending
- 1967-06-30 GB GB3038967A patent/GB1121418A/en not_active Expired
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4288523A (en) | 1980-03-14 | 1981-09-08 | Polaroid Corporation | Diffusion control layers in diffusion transfer photographic products |
| US4546159A (en) * | 1980-03-14 | 1985-10-08 | Polaroid Corporation | Eliminating polymers useful in diffusion control layers |
| WO1982003131A1 (en) * | 1981-03-02 | 1982-09-16 | Corp Polaroid | Cleavable polymers and photographic products and processes employing same |
| US4639286A (en) * | 1982-09-27 | 1987-01-27 | Minnesota Mining And Manufacturing Company | Curable compositions containing azlactone-functional compounds |
| US4619867A (en) * | 1983-06-14 | 1986-10-28 | Minnesota Mining And Manufacturing Company | Azlactone-containing pressure-sensitive adhesives |
| US4699843A (en) * | 1983-06-14 | 1987-10-13 | Minnesota Mining And Manufacturing Company | Azlactone-containing pressure-sensitive adhesives |
| US4695608A (en) * | 1984-03-29 | 1987-09-22 | Minnesota Mining And Manufacturing Company | Continuous process for making polymers having pendant azlactone or macromolecular moieties |
| US4981933A (en) * | 1989-06-23 | 1991-01-01 | Polaroid Corporation | Azlactone copolymers |
| US5523080A (en) * | 1993-05-18 | 1996-06-04 | Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. | Cosmetic treatment of substrates |
| US5525332A (en) * | 1993-05-18 | 1996-06-11 | Chesebrough-Pond's Usa Co. | Cosmetic treatment of substrates |
| CN100500994C (en) * | 2006-10-23 | 2009-06-17 | 上海东升新材料有限公司 | Method for preparing aqueous base material for treating vacuum aluminum plated paper |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1745330A1 (en) | 1971-08-26 |
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