GB885840A - Selective monoepoxidation of diunsaturated esters of acrylic and methacrylic acids - Google Patents
Selective monoepoxidation of diunsaturated esters of acrylic and methacrylic acidsInfo
- Publication number
- GB885840A GB885840A GB10242/58A GB1024258A GB885840A GB 885840 A GB885840 A GB 885840A GB 10242/58 A GB10242/58 A GB 10242/58A GB 1024258 A GB1024258 A GB 1024258A GB 885840 A GB885840 A GB 885840A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methacrylate
- ester
- group
- alkyl
- methyl
- 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
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/34—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/38—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing crosslinkable groups
- D21H17/40—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing crosslinkable groups unsaturated
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- 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
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
- D06M15/273—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof of unsaturated carboxylic esters having epoxy groups
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/34—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/38—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing crosslinkable groups
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Paper (AREA)
Abstract
Epoxy esters of the formula <FORM:0885840/IV (a)/1> where R1 and R2 represent hydrogen or a methyl group, R3 represents hydrogen or a C1-C11 alkyl group and R4 represents a C1-C13 alkylene group, with the proviso that R2 and R3 are such that one is alkyl and the other is hydrogen and that R3 and R4 together contain no more than 20 carbon atoms, may be polymerized or copolymerized with other compounds containing a CH2 = C< group in bulk, in solution or in emulsion at a temperature of from 0 DEG to 100 DEG C., preferably 40 DEG -80 DEG C. in the presence of freeradical catalysts, e.g. a , a 1-bis-azoisobutyronitrile, benzoyl peroxide and stearoyl peroxide, in an amount of 0,01 to 5%, preferably 0,02 to 2%, based on the weight of the polymerizable compound. Suitable copolymerizable materials are alkyl esters of acrylic and methacrylic acids, the alkyl group of which are straight or branched, of one to eight carbon atoms. Illustrative alkyl groups are methyl, ethyl, isopropyl, n-butyl, n-octyl and 2-ethylhexyl. The copolymers are useful in coating compositions, paper-treating and shrink-proofing and felt-proofing of textiles.ALSO:A mono-epoxy ester is made by selective epoxidation of the ethylenic bond in the alkenyl moiety of an ester of the formula <FORM:0885840/IV (b)/1> where R1 and R2 represent hydrogen or a methyl group, R3 represents hydrogen or a C1-C11 alkyl group, and R4 represents a C1-C13 alkylene group, with the proviso that R2 and R3 are such that one is alkyl and the other is hydrogen and that R3 and R4 together contain no more than 20 carbon atoms, which method comprises bringing together and reacting at a temperature in the range from about 30 DEG C. to about 50 DEG C., preferably 40 DEG C. to 50 DEG C., said ester and at least one mole of an epoxidizing peracid per mole of ester and reacting said ester and peracid until monoepoxidation is substantially complete, the reaction being carried out in the presence of a substantially water-soluble basic agent which when present in a 0.1 N concentration in water, imparts thereto a pH of at least 8 at 25 DEG C. The peracid is preferably added gradually, in continuous or portionwise fashion, to the unsaturated ester. Peracids specified are perbenzoic, monoperphthalic and peracetic acid in chloroform, ether and acetic acid respectively. Suitable basic agents are oxides and hydroxides of alkali metals and alkaline earth metals or salts of alkali metals and weak aliphatic carboxylic acids, e.g. sodium acetate. The starting materials are made by acidcatalyzed esterification of unsaturated alcohols with excess glacial methacrylic or acrylic acid in an inert solvent with a polymerization inhibitor, or by base-catalyzed transesterification of monoolefinic alcohols with an ester of acrylic or methacrylic acid using a polymerization inhibitor. The alcohols may also be reacted with the appropriate acid chloride or anhydride. Suitable starting materials are specified. Examples describe the preparation of crotyl methacrylate, methallyl methacrylate and 4-methyl-4-penten-1-yl methacrylate, and the epoxidation of these esters and of 10 - methyl - 10 - undecenyl methacrylate, 3-pentenyl methacrylate, methallyl acrylate, oleyl methacrylate, 8-eicosenyl methacrylate; 13,14-epoxytetracosyl-, 12,13-epoxyeicosyl-, 8,9-epoxy-dodecyl and 4,5-epoxyhexyl methacrylate 13,14-epoxytetracosyl acrylate and 9,10-epoxyoctadecyl acrylate are similarly prepared. The products are readily polymerized or copolymerized (see Group IV(a)).
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US885839XA | 1957-04-05 | 1957-04-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB885840A true GB885840A (en) | 1961-12-28 |
Family
ID=22212220
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB10242/58A Expired GB885840A (en) | 1957-04-05 | 1958-03-31 | Selective monoepoxidation of diunsaturated esters of acrylic and methacrylic acids |
GB10196/58A Expired GB885839A (en) | 1957-04-05 | 1958-03-31 | Monoepoxidation of diunsaturated esters of acrylic and methacrylic acids |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB10196/58A Expired GB885839A (en) | 1957-04-05 | 1958-03-31 | Monoepoxidation of diunsaturated esters of acrylic and methacrylic acids |
Country Status (1)
Country | Link |
---|---|
GB (2) | GB885840A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5756777A (en) * | 1994-10-11 | 1998-05-26 | Daicel Chemical Industries, Ltd. | (Meth)acrylate having an alkenyl group, an epoxy (meth)acrylate, a (meth)acrylic resin having alkenyl groups, a (meth)acrylic resin having epoxy groups, a thermosetting resin composition, a coating composition, a powder coating composition |
-
1958
- 1958-03-31 GB GB10242/58A patent/GB885840A/en not_active Expired
- 1958-03-31 GB GB10196/58A patent/GB885839A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
GB885839A (en) | 1961-12-28 |
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