GB1048906A - Cyanoacrylate esters - Google Patents

Cyanoacrylate esters

Info

Publication number
GB1048906A
GB1048906A GB2968464A GB2968464A GB1048906A GB 1048906 A GB1048906 A GB 1048906A GB 2968464 A GB2968464 A GB 2968464A GB 2968464 A GB2968464 A GB 2968464A GB 1048906 A GB1048906 A GB 1048906A
Authority
GB
United Kingdom
Prior art keywords
glycol
dicyanoacrylates
parts
compounds
condensing
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
Application number
GB2968464A
Inventor
Benjamin David Halpern
Jack Dickstein
Rose-Marie Hoegerle
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hexion Inc
Original Assignee
Borden Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Borden Inc filed Critical Borden Inc
Priority to GB2968464A priority Critical patent/GB1048906A/en
Publication of GB1048906A publication Critical patent/GB1048906A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J135/00—Adhesives 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 a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J135/04—Homopolymers or copolymers of nitriles

Abstract

The invention comprises compounds of the formula <FORM:1048906/C2/1> where R is <FORM:1048906/C2/2> <FORM:1048906/C2/3> or <FORM:1048906/C2/4> wherein x is 2-30. The compounds are made by esterifying the appropriate glycol or polyethylene glycol with cyanoacetic acid and condensing the resulting dicyanoacetate with formaldehyde in the presence of a condensing agent, e.g. zinc acetate, piperidine, piperidine acetate. The dicyanoacrylates and polymers thereof are used in adhesive compositions (see Division C3). Examples relate to the dicyano-acrylates of ethylene glycol, diethylene glycol and neopentyl glycol.ALSO:The invention comprises dicyanoacrylates of the formula <FORM:1048906/C3/1> where R is <FORM:1048906/C3/2> or <FORM:1048906/C3/3> wherein x is 2-30, and homopolymers thereof and copolymers of 10 parts by wt. thereof and 1-9 parts by wt. of vinyl chloride, vinyl acetate, methyl acrylate, ethyl acrylate, methyl methacrylate, ethyl methacrylate, styrene and/or vinyl toluene. The dicyanoacrylates of polyethylene glycol are made by esterifying the PEG with cyanoacetic acid and condensing the resulting dicyanoacetate with formaldehyde. Some carbon-to-carbon polymerization may occur during the preparation of the monomers, but the homopolymers and copolymers are also made by heating to higher temperatures, e.g. 80-150 DEG C., the presence of an initiator, e.g. Na or K persulphate, benzoyl peroxide or azobisisobutyronitrile. The compounds and polymers are used in adhesive compositions in admixture with 2-10 parts by wt. of a volatile, inert solvent, e.g. acetone, methyl ethyl ketone or N,N-dimethylformamide.
GB2968464A 1964-07-23 1964-07-23 Cyanoacrylate esters Expired GB1048906A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2968464A GB1048906A (en) 1964-07-23 1964-07-23 Cyanoacrylate esters

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2968464A GB1048906A (en) 1964-07-23 1964-07-23 Cyanoacrylate esters

Publications (1)

Publication Number Publication Date
GB1048906A true GB1048906A (en) 1966-11-23

Family

ID=10295457

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2968464A Expired GB1048906A (en) 1964-07-23 1964-07-23 Cyanoacrylate esters

Country Status (1)

Country Link
GB (1) GB1048906A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0168563A2 (en) * 1984-06-23 1986-01-22 Hüls Aktiengesellschaft Process for the preparation of alkylidene and arylidene compounds
WO1994015907A1 (en) * 1993-01-11 1994-07-21 Eurotax Limited Process for the preparation of esters of 2-cyanoacrylic acid and use of the esters so prepared as adhesives
WO2010023229A1 (en) * 2008-09-01 2010-03-04 Loctite (R&D) Limited Transferable curable non-liquid film on a release substrate
WO2013064059A1 (en) 2011-11-02 2013-05-10 中国人民解放军军事医学科学院毒物药物研究所 Biodegradable medical adhesive and preparation method and use thereof
WO2014131650A1 (en) 2013-02-26 2014-09-04 Henkel Ag & Co. Kgaa Hot melt adhesive comprising cyanoacrylate curing compounds
WO2017210084A1 (en) * 2016-06-03 2017-12-07 Sirrus, Inc. Water absorbing or water soluble polymers, intermediate compounds, and methods thereof
CN109153866A (en) * 2016-06-03 2019-01-04 赛鲁斯股份有限公司 Water imbibition or water-soluble polymer, intermediate compound and its method
US10428177B2 (en) 2016-06-03 2019-10-01 Sirrus, Inc. Water absorbing or water soluble polymers, intermediate compounds, and methods thereof

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0168563A2 (en) * 1984-06-23 1986-01-22 Hüls Aktiengesellschaft Process for the preparation of alkylidene and arylidene compounds
EP0168563A3 (en) * 1984-06-23 1986-02-05 Huels Chemische Werke Ag Process for the preparation of alkylidene and arylidene compounds
WO1994015907A1 (en) * 1993-01-11 1994-07-21 Eurotax Limited Process for the preparation of esters of 2-cyanoacrylic acid and use of the esters so prepared as adhesives
CN102369252B (en) * 2008-09-01 2015-03-11 汉高知识产权控股有限责任公司 Transferable curable non-liquid film on a release substrate
GB2463065B (en) * 2008-09-01 2012-11-07 Loctite R & D Ltd Transferable curable non-liquid film on a release substrate
US8425999B2 (en) 2008-09-01 2013-04-23 Henkel Ireland Limited Transferable curable non-liquid film on a release substrate
WO2010023229A1 (en) * 2008-09-01 2010-03-04 Loctite (R&D) Limited Transferable curable non-liquid film on a release substrate
WO2013064059A1 (en) 2011-11-02 2013-05-10 中国人民解放军军事医学科学院毒物药物研究所 Biodegradable medical adhesive and preparation method and use thereof
US20140369952A1 (en) * 2011-11-02 2014-12-18 Institute Of Pharmacology And Toxicology Academy Of Military Medical Sciences P.L.A. Biodegradable medical adhesive and preparation method and use thereof
US9750841B2 (en) * 2011-11-02 2017-09-05 Institute Of Pharmacology And Toxicology Academy Of Military Medical Sciences P.L.A. Biodegradable medical adhesive and preparation method and use thereof
WO2014131650A1 (en) 2013-02-26 2014-09-04 Henkel Ag & Co. Kgaa Hot melt adhesive comprising cyanoacrylate curing compounds
WO2017210084A1 (en) * 2016-06-03 2017-12-07 Sirrus, Inc. Water absorbing or water soluble polymers, intermediate compounds, and methods thereof
CN109153866A (en) * 2016-06-03 2019-01-04 赛鲁斯股份有限公司 Water imbibition or water-soluble polymer, intermediate compound and its method
JP2019522064A (en) * 2016-06-03 2019-08-08 シラス・インコーポレイテッド Water-absorbing or water-soluble polymers, intermediate compounds, and methods thereof
US10428177B2 (en) 2016-06-03 2019-10-01 Sirrus, Inc. Water absorbing or water soluble polymers, intermediate compounds, and methods thereof

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