GB935018A - Aqueous dispersions of monoepoxycyclic acrylates for treating textile materials - Google Patents
Aqueous dispersions of monoepoxycyclic acrylates for treating textile materialsInfo
- Publication number
- GB935018A GB935018A GB3985559A GB3985559A GB935018A GB 935018 A GB935018 A GB 935018A GB 3985559 A GB3985559 A GB 3985559A GB 3985559 A GB3985559 A GB 3985559A GB 935018 A GB935018 A GB 935018A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- vinyl
- methacrylate
- formula
- butyl
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- 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
- D06M15/267—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 amino or quaternary ammonium groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (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)
Abstract
Relates to an aqueous dispersion of a water-insoluble, linear polymer containing at least 3% by weight of units derived from one or more monoethylenically unsaturated monomeric cyclic epoxides of the formula <FORM:0935018/IV(a)/1> by polymerization through the terminal <FORM:0935018/IV(a)/2> group, where, in the formula, R represents hydrogen or methyl and M represents hydrogen or one or more methyl substituents which may or may not be bonded to the same carbon of the ring. The cyclic epoxide units may be derived from 1,2-, 2,3- or 3,4-epoxyhexahydrobenzyl acrylate or methacrylate, 6-methyl-3,4-, 2,3-dimethyl-1,2- or 2,3-dimethyl-2,3-hexahydrobenzyl methacrylate or 5-methyl-2,3-epoxyhexahydrobenzyl acrylate. Polymerization is preferably effected in aqueous dispersion in the presence of a non-ionic dispersing agent and a peroxide catalyst or a redox catalyst system, preferably in the presence of polymerizable monoethylenically unsaturated compounds such as vinyl ethyl, butyl, octyl, dodecyl or stearyl ether, allyl butyl, vinyl, octyl or decyl ether, methyl, ethyl, butyl, octyl or stearyl acrylate or methacrylate, methyl or butyl acrylamide or methacrylamide, vinyl acetate, butyrate or stearate, allyl butyrate, palmitate or stearate, butyl, octyl or dodecyl maleate, octyl, dodecyl or octadecyl itaconate, vinyl toluene, maleic anhydride, acrylonitrile, N-vinyl-pyrrolidone, N-vinyl-caprolactam, N-vinyl-N,N1-ethylene urea, and styrene. An example describes the copolymerization of various acrylates and methacrylates with 1,2-, 2,3- and 3,4-epoxyhexahydrobenzyl methacrylates using, as non-ionic dispersing agent, a tert.-octylphenoxypolyethoxyethanol and as catalyst a mixture of ammonium persulphate and sodium hydrosulphite. The aqueous dispersions of the invention may be used for stablizing textile materials comprising or consisting of protein fibres, particularly wool, against shrinking and felting, by impregnating the textile material with the dispersion and then curing by heating. The curing reaction may be accelerated by adding to the dispersion with which the textile is treated an acid such as formic, oxalic, sulphuric or phosphoric acid.ALSO:Cyclic epoxides of the formula <FORM:0935018/IV(a)/1> where R represents hydrogen or methyl and M represents hydrogen or one or more methyl substituents which may or may not be bonded to the same carbon of the ring, may be prepared by introducing an epoxy group into the ring of a compound represented by the formula <FORM:0935018/IV(a)/2> e.g. by treatment with perbenzoic or peracetic acid or with a mixture of hydrogen peroxide and acetic or formic acid. The preparation of 3,4-epoxyhexahydrobenzyl methacrylate from 1,2,5,6-tetrahydrobenzyl methacrylate is described. Other compounds are mentioned.ALSO:Textile materials comprising or consisting of scale-surfaced protein fibres are stabilized against shrinking and felting by treating the materials with an aqueous dispersion of a water-insoluble linear polymer containing at least 3% by weight of units derived from one or more monoethyleni cally unsaturated monomeric cyclic epoxides of the formula <FORM:0935018/IV(a)/1> by polymerization through the terminal <FORM:0935018/IV(a)/2> group, where, in the formula, R represents hydrogen or methyl and M represents hydrogen or one or more methyl substituents which may or may not be bonded to the same carbon of the ring, drying the material to deposit the dispersed polymer thereon and then heating the treated material to cure the deposited polymer. The textile materials may contain wool, silk, mohair, or synthetic fibres produced e.g., from casein or collagen, either alone or in admixture with other fibres such as cotton, linen, rayon, nylon or an acrylonitrile polymer. In a typical example pieces of flannel are treated with an aqueous dispersion of a copolymer of 3,4-epoxyhexahydrobenzyl methacrylate and n-butyl acrylate. Curing may be effected at a temperature from 212 DEG to 700 DEG F. for from five seconds to 30 minutes, the higher the temperature the shorter the period required. The curing reaction may be accelerated by adding to the dispersion with which the textile is treated an acid such as formic, oxalic, sulphuric or phosphoric acid.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US77828858A | 1958-12-05 | 1958-12-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB935018A true GB935018A (en) | 1963-08-28 |
Family
ID=25112839
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3985559A Expired GB935018A (en) | 1958-12-05 | 1959-11-24 | Aqueous dispersions of monoepoxycyclic acrylates for treating textile materials |
GB3985459A Expired GB935756A (en) | 1958-12-05 | 1959-11-24 | Monoepoxybicyclic acrylates and methacrylates and their polymers |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3985459A Expired GB935756A (en) | 1958-12-05 | 1959-11-24 | Monoepoxybicyclic acrylates and methacrylates and their polymers |
Country Status (3)
Country | Link |
---|---|
BE (1) | BE585307A (en) |
FR (2) | FR1243106A (en) |
GB (2) | GB935018A (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1297575B (en) * | 1960-04-15 | 1969-06-19 | Little Inc A | Process for the production of shrink-resistant wool |
NL292382A (en) * | 1962-05-18 | Laederich Ets | ||
US4440850A (en) * | 1981-07-23 | 1984-04-03 | Ciba-Geigy Corporation | Photopolymerisation process with two exposures of a single layer |
FR2664272B3 (en) * | 1990-07-06 | 1992-11-27 | Norsolor | PROCESS FOR THE SELECTIVE EPOXIDATION OF UNSATURATED (METH) ACRYLATES, NEW FUNCTIONAL (METH) ACRYLATES OBTAINED AND THEIR APPLICATION TO THE SYNTHESIS OF NEW POLYMERS. |
TWI614239B (en) * | 2012-11-28 | 2018-02-11 | 捷恩智股份有限公司 | Norbornene derivative and manufacturing method of norbornene derivative |
-
0
- BE BE585307D patent/BE585307A/xx unknown
-
1959
- 1959-11-24 GB GB3985559A patent/GB935018A/en not_active Expired
- 1959-11-24 GB GB3985459A patent/GB935756A/en not_active Expired
- 1959-12-05 FR FR812228A patent/FR1243106A/en not_active Expired
- 1959-12-05 FR FR812229A patent/FR1244610A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
FR1243106A (en) | 1960-10-07 |
FR1244610A (en) | 1960-10-28 |
BE585307A (en) | |
GB935756A (en) | 1963-09-04 |
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