GB1100914A - Production of amide or ester interpolymers - Google Patents
Production of amide or ester interpolymersInfo
- Publication number
- GB1100914A GB1100914A GB4994/65A GB499465A GB1100914A GB 1100914 A GB1100914 A GB 1100914A GB 4994/65 A GB4994/65 A GB 4994/65A GB 499465 A GB499465 A GB 499465A GB 1100914 A GB1100914 A GB 1100914A
- Authority
- GB
- United Kingdom
- Prior art keywords
- esters
- alkyl
- amide
- carbon atoms
- radical
- 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
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
- C08F4/00—Polymerisation catalysts
- C08F4/28—Oxygen or compounds releasing free oxygen
- C08F4/32—Organic compounds
-
- 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
- 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
- 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
- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Amides or alkyl or hydroxyalkyl esters of a ,b -ethylenically unsaturated carboxylic acids are copolymerized with at least one other ethlenically unsaturated monomer in the presence of a peroxy-carbonate catalyst having the formula <FORM:1100914/C3/1> or <FORM:1100914/C3/2> or <FORM:1100914/C3/3> wherein R is either a tertiary alkyl radical having up to about 8 carbon atoms or a tertiary aralkyl radical whose alkyl moiety has up to about 8 carbon atoms, R1 is an alkyl radical of up to about 8 carbon atoms, an aryl radical, an aralkyl radical or an alkoxy alkyl radical, and R2 is an alkylene radical of up to about 12 carbon atoms or an oxaalkylene radical of up to about 10 carbon atoms, said radicals if desired containing substituents (e.g. nitro, halogen, ether or hydroxyl groups) inert to the reaction conditions, the temperature being at least about 200 DEG F. during the major part of the polymerization. (The term "alkyl" is used herein to include cycloalkyl radicals.) The peroxycarbonate may be used in combination with other catalysts such as di-t.-butyl peroxide, t.butyl hydroperoxide and azobisisobutyronitrile. Amide monomers specified are acrylamide, methacrylamide, itaconic acid diamide, a -ethyl-acrylamide, crotonamide, maleamic acid and esters, maleuric acid and esters and N-n-butoxymethyl acrylamide. Preferred esters are those of acrylic or methacrylic acid containing up to 12 carbon atoms in the alkyl or hydroxyalkyl group; also suitable are esters of ethacrylic, crotonic, maleic, fumaric and itaconic acids. Suitable comonomers include acrylate esters, styrene, vinyl toluene, acrylonitrile, methacrylonitrile, acrylic acid, methacrylic acid, butadiene, 2-chlorobutene, a -methylstyrene, a -chlorostyrene, 2-chlorobutadiene, 1,1-dichloroethylene, vinyl acetate and butyrate, allyl chloride, dimethyl maleate, divinylbenzene, diallyl itaconate and triallyl cyanurate. Polymerization is generally effected in solution, optionally in the presence of a chain transfer agent, e.g. dodecyl mercaptan; suitable polymerization solvents include n- or isobutanol and mixtures thereof with xylene or aromatic naphtha. The amide polymers may be alkylolated by reaction with an aldehyde (e.g. formaldehyde, acetaldehyde or butyraldehyde) and, if desired, some or all of the alkylol groups may be etherified with an alcohol; alternatively an N-alkylol amide monomer may be used in the polymerization process. The polymer solutions obtained may be combined with pigments (e.g. titanium dioxide), fillers &c., and used for coating substrates, e.g. steel, aluminium or tin plate, the coatings being curable by baking.ALSO:Polymers obtained by copolymerising amides or alkyl or hydroxyalkyl esters of a , b -ethylenically unsaturated carboxylic acids in solution in an organic solvent and in the presence of certain peroxy carbonate catalysts (see Division C3) are suitable for coating metal substrates, e.g. steel, aluminium and tin-plate. The amide polymers may have amide groups alkylolated by reaction with an aldehyde and the alkylol groups may be optionally etherified with an alcohol. The polymers can be admixed with the usual additives such as pigments and fillers. The coatings can be cured by baking at 150 DEG -300 DEG F for from 10 to 45 minutes. In Examples, coatings on tin-plate were obtained using an acrylamide/styrene/ethyl acrylate/methacrylic acid copolymer obtained by solution polymerisation in an n-butanol / aromatic naphtha solvent, and on aluminium using an acrylamide/styrene/ethyl acrylate/methacrylic acid/ acrylonitrile copolymer obtained by solution polymerisation in an n-butanol/xylene solvent; both these polymers had amide groups methylolated with formaldehyde and further etherified with n-butanol, and were pigmented with titanium dioxide in a 1:1 weight ratio.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US35298264A | 1964-03-18 | 1964-03-18 | |
US36043064A | 1964-04-16 | 1964-04-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1100914A true GB1100914A (en) | 1968-01-24 |
Family
ID=26997741
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4994/65A Expired GB1100914A (en) | 1964-03-18 | 1965-02-04 | Production of amide or ester interpolymers |
Country Status (7)
Country | Link |
---|---|
AT (1) | AT264822B (en) |
BE (1) | BE660383A (en) |
CH (1) | CH497471A (en) |
DE (1) | DE1301533B (en) |
GB (1) | GB1100914A (en) |
NL (2) | NL6502384A (en) |
SE (1) | SE345133B (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4929747A (en) * | 1985-08-21 | 1990-05-29 | Nippon Oil & Fats Company, Ltd. | Organic peroxide having a polymerization-regulating ability |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2173005A (en) * | 1936-07-08 | 1939-09-12 | Du Pont | Resinous products from aldehydes and acrylic amides |
-
0
- NL NL126218D patent/NL126218C/xx active
-
1965
- 1965-02-04 GB GB4994/65A patent/GB1100914A/en not_active Expired
- 1965-02-25 NL NL6502384A patent/NL6502384A/xx unknown
- 1965-02-26 BE BE660383D patent/BE660383A/xx unknown
- 1965-03-09 AT AT210365A patent/AT264822B/en active
- 1965-03-10 CH CH332065A patent/CH497471A/en not_active IP Right Cessation
- 1965-03-12 DE DEP36265A patent/DE1301533B/en active Pending
- 1965-03-12 SE SE3239/65A patent/SE345133B/xx unknown
Also Published As
Publication number | Publication date |
---|---|
NL126218C (en) | |
DE1301533B (en) | 1969-08-21 |
AT264822B (en) | 1968-09-10 |
NL6502384A (en) | 1965-09-20 |
BE660383A (en) | 1965-08-26 |
SE345133B (en) | 1972-05-15 |
CH497471A (en) | 1970-10-15 |
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