GB1226657A - - Google Patents
Info
- Publication number
- GB1226657A GB1226657A GB1226657DA GB1226657A GB 1226657 A GB1226657 A GB 1226657A GB 1226657D A GB1226657D A GB 1226657DA GB 1226657 A GB1226657 A GB 1226657A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acrylate
- coating
- acid
- unsaturated
- halogen
- 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
- 238000000576 coating method Methods 0.000 abstract 4
- 239000000178 monomer Substances 0.000 abstract 4
- -1 aging retardants Substances 0.000 abstract 3
- 239000011248 coating agent Substances 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- VNBVMEJAPNHJSI-UHFFFAOYSA-N 2,3-dichloropropyl prop-2-enoate Chemical compound ClCC(Cl)COC(=O)C=C VNBVMEJAPNHJSI-UHFFFAOYSA-N 0.000 abstract 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000000758 substrate Substances 0.000 abstract 2
- TXFMWXZBXNRSAD-OWOJBTEDSA-N (Z)-3-bromo-2,3-dichloroprop-2-enoic acid Chemical compound OC(=O)C(\Cl)=C(/Cl)Br TXFMWXZBXNRSAD-OWOJBTEDSA-N 0.000 abstract 1
- IAMALOVTVCLUKP-IHWYPQMZSA-N (z)-2-chlorobut-2-enoyl chloride Chemical compound C\C=C(/Cl)C(Cl)=O IAMALOVTVCLUKP-IHWYPQMZSA-N 0.000 abstract 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 abstract 1
- XMKLTEGSALONPH-UHFFFAOYSA-N 1,2,4,5-tetrazinane-3,6-dione Chemical class O=C1NNC(=O)NN1 XMKLTEGSALONPH-UHFFFAOYSA-N 0.000 abstract 1
- KCPLWWMMVXVWEO-UHFFFAOYSA-N 1h-inden-1-yl prop-2-enoate Chemical class C1=CC=C2C(OC(=O)C=C)C=CC2=C1 KCPLWWMMVXVWEO-UHFFFAOYSA-N 0.000 abstract 1
- MUKJDVAYJDKPAG-UHFFFAOYSA-N 2,3-dibromopropyl prop-2-enoate Chemical compound BrCC(Br)COC(=O)C=C MUKJDVAYJDKPAG-UHFFFAOYSA-N 0.000 abstract 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- YTGHIUMMBLPDEX-UHFFFAOYSA-N 2-bromoundec-2-enoic acid Chemical compound CCCCCCCCC=C(Br)C(O)=O YTGHIUMMBLPDEX-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 150000001252 acrylic acid derivatives Chemical class 0.000 abstract 1
- 150000001266 acyl halides Chemical class 0.000 abstract 1
- 230000032683 aging Effects 0.000 abstract 1
- 125000003158 alcohol group Chemical group 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 230000001680 brushing effect Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 229930016911 cinnamic acid Natural products 0.000 abstract 1
- 235000013985 cinnamic acid Nutrition 0.000 abstract 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 abstract 1
- 238000007598 dipping method Methods 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 230000005251 gamma ray Effects 0.000 abstract 1
- 239000003999 initiator Substances 0.000 abstract 1
- 230000001678 irradiating effect Effects 0.000 abstract 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 abstract 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000000025 natural resin Substances 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 239000000049 pigment Substances 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 230000001737 promoting effect Effects 0.000 abstract 1
- 230000005855 radiation Effects 0.000 abstract 1
- 238000005096 rolling process Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000005507 spraying Methods 0.000 abstract 1
- 150000003440 styrenes Chemical class 0.000 abstract 1
- 229920003002 synthetic resin Polymers 0.000 abstract 1
- 239000000057 synthetic resin Substances 0.000 abstract 1
- 238000010345 tape casting Methods 0.000 abstract 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 abstract 1
- 229920001567 vinyl ester resin Polymers 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- C08F220/10—Esters
- C08F220/22—Esters containing halogen
Abstract
1,226,657. Coating. BADISCHE ANILIN- & SODA-FABRIK A.G. 10 July, 1968 [11 July, 1967], No. 32871/68. Heading B2E. [Also in Division C3] Coatings are produced on substrates, e.g. metal articles, by coating the article with a mixture of olefinically unsaturated monomers containing 10-90% by weight of at least one ester derived from an α, #-olefinically unsaturated monocarboxylic acid and a chlorinated and/or brominated monohydric alcohol, and polymerising the coating by irradiating with high-energy radiation at atmospheric pressure. Preferably, polymerisation is effected in the absence of solvents. The substrate can be coated by spraying, brushing, pouring, rolling, knife-coating, flooding or dipping. The specified ester monomer is preferably a chloro (or bromo) alkyl ester of acrylic, methacrylic, crotonic or cinnamic acid; the alcohol moiety may additionally contain a double bond or nitro group and the acid moiety may be halosubstituted (including, e.g. bromoundecenoic acid). The other component(s) of the monomer mixture may be, for example, (meth)acrylate esters, vinylbenzenes, unsaturated nitriles; vinyl esters, olefins, halogen-containing compounds such as halogen-containing unsaturated acids, unsaturated acyl halides and halogen-containing unsaturated amides, and compounds containing two or more polymerisable double bonds. The polymerisable system may optionally include molecular weight regulators, e.g. mercaptans, acetoacetic esters, haloparaffins or aldehydes, pigments, dyes, optical brighteners, plasticisers, flow or gloss promoting agents, polymerisation initiators, aging retardants, and natural or synthetic resins. Irradiation can be effected with electron rays, X-rays or gammarays. In the Examples the following monomer systems are polymerised (1) and (2) 2, 3- dibromopropyl acrylate and N, N', N", N"'- tetra (allyloxymethyl)-acetylene-diurea; (3) 3a, 4, 5, 6, 7, 7a-hexahydro-4, 7-methanoindenyl acrylate-(5) and 2, 3-dichloropropyl acrylate; (4) 2, 3-dibromopropyl α-chloroacrylate, triethylene glycol diacrylate and the diurea derivative of (1) and (2); (5) the indenyl acrylate derivative of (3), 2, 3-dichloro-3-bromoacrylic acid and 2-chloroallyl acrylate; (6) 2- chlorocrotonyl chloride, 2, 3-dichloropropyl acrylate and trialllyl cyanurate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19671720283 DE1720283A1 (en) | 1967-07-11 | 1967-07-11 | Process for the production of crosslinked polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1226657A true GB1226657A (en) | 1971-03-31 |
Family
ID=5689762
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1226657D Expired GB1226657A (en) | 1967-07-11 | 1968-07-10 |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3627659A (en) |
| GB (1) | GB1226657A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4131580A (en) * | 1976-03-08 | 1978-12-26 | Rohm And Haas Company | Water-based coating compositions comprising a vinyl addition polymer and an acrylic ester of dicyclopentadiene |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS576578B2 (en) * | 1973-11-05 | 1982-02-05 | ||
| US4307155A (en) * | 1976-02-23 | 1981-12-22 | The Dow Chemical Co. | Process of making wood-polymer composite containing a dicyclopentenyl acrylate or methacrylate polymer and composite |
| US4250214A (en) * | 1976-02-23 | 1981-02-10 | The Dow Chemical Company | Wood-polymer composite containing a dicyclopentenyl acrylate or methacrylate polymer |
| US4263372A (en) * | 1976-05-19 | 1981-04-21 | Rohm And Haas Company | Method of coating and/or impregnating porous substrates, and products obtained thereby |
| US4400413A (en) * | 1980-08-29 | 1983-08-23 | Rohm And Haas Company | Acrylic polymer concrete compositions |
| US4460625A (en) * | 1981-07-16 | 1984-07-17 | Rohm And Haas Company | Method of coating and impregnating concrete substrates, and products obtained thereby |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE520401A (en) * | 1952-06-03 | |||
| US3213072A (en) * | 1961-08-07 | 1965-10-19 | American Cyanamid Co | Chlorination product of methylmethacrylate |
| US3255163A (en) * | 1963-08-22 | 1966-06-07 | Thiokol Chemical Corp | Halo butenyl acrylates and polymers thereof |
-
1968
- 1968-07-08 US US743033A patent/US3627659A/en not_active Expired - Lifetime
- 1968-07-10 GB GB1226657D patent/GB1226657A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4131580A (en) * | 1976-03-08 | 1978-12-26 | Rohm And Haas Company | Water-based coating compositions comprising a vinyl addition polymer and an acrylic ester of dicyclopentadiene |
Also Published As
| Publication number | Publication date |
|---|---|
| US3627659A (en) | 1971-12-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |