GB1015868A - Improved adhesive compositions based on glycol acrylate esters - Google Patents

Improved adhesive compositions based on glycol acrylate esters

Info

Publication number
GB1015868A
GB1015868A GB11?533/64A GB1153364A GB1015868A GB 1015868 A GB1015868 A GB 1015868A GB 1153364 A GB1153364 A GB 1153364A GB 1015868 A GB1015868 A GB 1015868A
Authority
GB
United Kingdom
Prior art keywords
diester
glycol
compositions
drying oil
hydroquinone
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
GB11?533/64A
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.)
Leicester Lovell and Co Ltd
Original Assignee
Leicester Lovell and Co Ltd
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 Leicester Lovell and Co Ltd filed Critical Leicester Lovell and Co Ltd
Priority to GB11?533/64A priority Critical patent/GB1015868A/en
Publication of GB1015868A publication Critical patent/GB1015868A/en
Expired legal-status Critical Current

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
    • C08F222/00—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 one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
    • 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
    • C08F291/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
    • 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
    • C09J133/00—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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • 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
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
    • C08L91/005—Drying oils

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

Adhesive compositions comprise a diester of acrylic acid or a substituted acrylic acid, e.g. methacrylic acid, and a water-soluble glycol in admixture with a fatty glyceride drying oil. Suitable glycols for forming the diester are 2,2 - dimethyl - 1,3 - propanediol (neopentyl glycol), tetraethylene glycol, triethylene glycol, ethylene glycol, diethylene glycol and the propylene and butylene homologues thereof. Drying oils specified are perilla, oiticica, linseed, tung and soybean oils. The composition may also comprise a polymer which is soluble in the diester and in the interpolymer of the diester and drying oil, e.g. polystyrene, polymethyl methacrylate, styrene-maleic acid (or anhydride) copolymer, polydiallyl phthalate, chlorinated rubber and copolymers of ethyl or methyl acrylate or methacrylate with acrylonitrile; alternatively, the composition may comprise a corresponding monomer. Preferably, the diester, drying oil and additional monomer, if present, are partially interpolymerized. The compositions can be cured by adding thereto a polymerization initiator, e.g. a peroxide or hydroperoxide (several specified). A polymerization inhibitor may also be included, e.g. hydroquinone, pyrogallol, quinhydrone, or the monoethyl, monophenyl or monotertiary butyl ether of hydroquinone. The compositions are suitable for bonding nuts and bolts, and also for joining ends of pipes which would normally be welded or soldered together. An example illustrates compositions based on tetraethylene glycol dimethacrylate and linseed oil, with or without polystyrene, and including as polymerization initiator a mixture of diisopropylbenzene hydroperoxide and methyl ethyl ketone peroxide.ALSO:Adhesive compositions comprise a diester of acrylic acid or a substituted acrylic acid, e.g. methacrylic acid, and a water-soluble glycol in admixture with a fatty glyceride drying oil. Suitable glycols for forming the diester are 2,2-dimethyl-1,3-propanediol (neopentyl glycol), tetraethylene glycol, triethylene glycol, ethylene glycol, diethylene glycol and the propylene and butylene homologues thereof. Drying oils specified are perilla, oiticica, linseed, tung and soybean oils. The composition may also comprise a polymer which is soluble in the diester and in the interpolymer of the diester and drying oil, e.g. polystyrene, polymethyl methacrylate, styrene-maleic acid (or anhydride) copolymer, polydiallyl phthalate, chlorinated rubber and copolymers of ethyl or methyl acrylate or methacrylate with acrylonitrile; alternatively, the composition may comprise a corresponding monomer. Preferably, the diester, drying oil and additional monomer, if present, are partially interpolymerized. The compositions can be cured by adding thereto a polymerization initiator, e.g. a peroxide or hydroperoxide (several specified). A polymerization inhibitor may also be included, e.g. hydroquinone, pyrogallol, quinhydrone, or the monoethyl, monophenyl or monotertiary butyl ether of hydroquinone. The compositions are suitable for bonding nuts and bolts, and also for joining ends of pipes which would normally be welded or soldered together. An example illustrates compositions based on tetraethylene glycol dimethacrylate and linseed oil, with or without polystyrene, and including as polymerization initiator a mixture of diisopropyl benzene hydroperoxide and methyl ethyl ketone peroxide.
GB11?533/64A 1964-03-18 1964-03-18 Improved adhesive compositions based on glycol acrylate esters Expired GB1015868A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB11?533/64A GB1015868A (en) 1964-03-18 1964-03-18 Improved adhesive compositions based on glycol acrylate esters

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB11?533/64A GB1015868A (en) 1964-03-18 1964-03-18 Improved adhesive compositions based on glycol acrylate esters

Publications (1)

Publication Number Publication Date
GB1015868A true GB1015868A (en) 1966-01-05

Family

ID=9987988

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11?533/64A Expired GB1015868A (en) 1964-03-18 1964-03-18 Improved adhesive compositions based on glycol acrylate esters

Country Status (1)

Country Link
GB (1) GB1015868A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016512851A (en) * 2013-03-15 2016-05-09 ヘンケル アイピー アンド ホールディング ゲゼルシャフト ミット ベシュレンクテル ハフツング Anaerobic curable composition
CN107001685A (en) * 2014-12-09 2017-08-01 阿科玛股份有限公司 The composition and method of cross-linked polymer in the presence of aerial oxygen

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016512851A (en) * 2013-03-15 2016-05-09 ヘンケル アイピー アンド ホールディング ゲゼルシャフト ミット ベシュレンクテル ハフツング Anaerobic curable composition
EP2970540A4 (en) * 2013-03-15 2016-08-24 Henkel IP & Holding GmbH Anaerobic curable compositions
CN107001685A (en) * 2014-12-09 2017-08-01 阿科玛股份有限公司 The composition and method of cross-linked polymer in the presence of aerial oxygen
JP2017537202A (en) * 2014-12-09 2017-12-14 アーケマ・インコーポレイテッド Compositions and methods for crosslinking polymers in the presence of atmospheric oxygen
US10563039B2 (en) * 2014-12-09 2020-02-18 Arkema Inc. Compositions and methods for crosslinking polymers in the presence of atmospheric oxygen

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