CA2525011A1 - Cyanoacrylate compositions - Google Patents

Cyanoacrylate compositions Download PDF

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Publication number
CA2525011A1
CA2525011A1 CA002525011A CA2525011A CA2525011A1 CA 2525011 A1 CA2525011 A1 CA 2525011A1 CA 002525011 A CA002525011 A CA 002525011A CA 2525011 A CA2525011 A CA 2525011A CA 2525011 A1 CA2525011 A1 CA 2525011A1
Authority
CA
Canada
Prior art keywords
cyanoacrylate
composition according
accelerator
composition
component
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.)
Granted
Application number
CA002525011A
Other languages
French (fr)
Other versions
CA2525011C (en
Inventor
Brendan J. Kneafsey
Harry J. Woolfson
David P. Birkett
Hanns R. Misiak
Kiernan Mulcahy
Ruth A. Kelly
Fergal W. Tierney
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.)
Henkel Loctite Ireland Ltd
Original Assignee
Loctite (R & D) Limited
Brendan J. Kneafsey
Harry J. Woolfson
David P. Birkett
Hanns R. Misiak
Kiernan Mulcahy
Ruth A. Kelly
Fergal W. Tierney
Loctite (Ireland) Limited
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 Loctite (R & D) Limited, Brendan J. Kneafsey, Harry J. Woolfson, David P. Birkett, Hanns R. Misiak, Kiernan Mulcahy, Ruth A. Kelly, Fergal W. Tierney, Loctite (Ireland) Limited filed Critical Loctite (R & D) Limited
Publication of CA2525011A1 publication Critical patent/CA2525011A1/en
Application granted granted Critical
Publication of CA2525011C publication Critical patent/CA2525011C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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
    • C08F22/00—Homopolymers and 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
    • C08F22/30—Nitriles
    • C08F22/32—Alpha-cyano-acrylic acid; Esters 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
    • 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
    • C08F222/30—Nitriles
    • C08F222/32—Alpha-cyano-acrylic acid; Esters thereof
    • C08F222/322—Alpha-cyano-acrylic acid ethyl ester, e.g. ethyl-2-cyanoacrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • 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

Abstract

This invention relates to cyanoacrylate-containing compositions that include, in addition to the cyanoacrylate component, certain accelerators to improve fixture speeds on certain substrates.

Claims (14)

1. A cyanoacrylate adhesive composition comprising:
a cyanoacrylate component; and an accelerator represented by the following chemical structure wherein R is a member selected from the group consisting of hydrogen, alkyl, alkyloxy, alkyl thioethers, haloalkyl, carboxylic acid and esters thereof, sulfinic, sulfonic and sulfurous acids and esters, phosphinic, phosphonic and phosphorous acids and esters thereof, X is an aliphatic or aromatic hydrocarbyl linkage, which may be substituted by oxygen or sulfur, Z is a single or double bond, n is 1-12, m is 1-4, and p is 1-3.
2. The composition of Claim 1, wherein the accelerator is represented by the following chemical structure wherein R, X, n, m, and p are as defined above.
3. The composition of Claim 1, wherein the accelerator is represented by the following chemical structure wherein R, Z, n, and p are as defined above, R' is the same as R, and g is 1-12.
4. The composition of Claim 1, wherein the accelerator is represented by the following chemical structure wherein n and m combined are greater than or equal to 12.
5. The composition according to Claim 1, wherein the cyanoacrylate component is selected from materials within the structure H2C=C(CN)-COOR, wherein R is selected from C1-15 alkyl, alkoxyalkyl, cycloalkyl, alkenyl, aralkyl, aryl, allyl and haloalkyl groups.
6. The composition according to Claim 1, wherein the cyanoacrylate component comprises ethyl-2-cyanoacrylate.
7. The composition according to Claim 1, further comprising an additional accelerator component selected from the group consisting of calixarenes, oxacalixarenes, silacrowns, cyclodextrins, crown ethers, poly(ethyleneglycol) di(meth)acrylates, ethoxylated hydric compounds, and combinations thereof.
8. The composition according to Claim 1, wherein the accelerator is used in an amount within the range of from about 0.01% by weight to about 5% by weight based on the total composition.
9. The composition according to Claim 7, wherein the additional accelerator component is used in an amount within the range of from about 0.01% by weight to about 5% by weight based on the total composition.
10. The composition according to Claim 1, further comprising additives selected from the group consisting of free radical stabilizers, anionic stabilizers, plasticizers, thixotropy conferring agents, thickeners, dyes, toughening agents, thermal degradation enhancers, and combinations thereof.
11. A cyanoacrylate adhesive composition comprising:
(a) a cyanoacrylate component; and (b) an accelerator component consisting essentially of (i) calixarenes, oxacalixarenes, or a combination thereof, and (ii) at least one crown ether, wherein said composition exhibits a fixturing speed of less than 20 seconds for bonding two substrates, at least one of which is constructed of a material selected from the group consisting of steel, epoxy glass, and balsawood.
12. Reaction products of the composition according to Claim 1.
13. A method of bonding together two substrates, at least one of which is constructed of a material selected from the group consisting of wood and ceramic, comprising the steps of:
applying a cyanoacrylate-containing adhesive composition according to Claim 1, to at least one of the substrates and mating together the substrates for a time sufficient to permit the adhesive to fixture.
14. A method of preparing a cyanoacrylate-containing composition according to Claim 1, comprising the steps of:

providing a cyanoacrylate component, and combining therewith with mixing an accelerator component.
CA2525011A 2003-06-18 2004-06-18 Cyanoacrylate compositions Expired - Fee Related CA2525011C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US10/463,461 US6835789B1 (en) 2003-06-18 2003-06-18 Cyanoacrylate compositions
US10/463,461 2003-06-18
PCT/IE2004/000086 WO2004111147A2 (en) 2003-06-18 2004-06-18 Cyanoacrylate compositions

Publications (2)

Publication Number Publication Date
CA2525011A1 true CA2525011A1 (en) 2004-12-23
CA2525011C CA2525011C (en) 2012-07-31

Family

ID=33517106

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2525011A Expired - Fee Related CA2525011C (en) 2003-06-18 2004-06-18 Cyanoacrylate compositions

Country Status (9)

Country Link
US (1) US6835789B1 (en)
EP (1) EP1633827A2 (en)
JP (1) JP4624997B2 (en)
KR (1) KR100964088B1 (en)
CN (1) CN1791649B (en)
BR (1) BRPI0411472A (en)
CA (1) CA2525011C (en)
MX (1) MXPA05012296A (en)
WO (1) WO2004111147A2 (en)

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US7270932B2 (en) * 2004-02-06 2007-09-18 Rohm And Haas Electronic Materials Llc Imaging composition and method
RU2394059C2 (en) 2005-07-11 2010-07-10 Хенкель Корпорейшн Packed cyanoacrylate compositions
CN101305040A (en) * 2005-11-10 2008-11-12 汉高两合股份公司 Binding agent, sealant and paint containing glass particle as filling material
EP1951831B1 (en) * 2005-11-10 2011-02-23 Henkel AG & Co. KGaA Adhesives, sealants and coatings containing glass particles as a filler
US7659423B1 (en) 2006-04-18 2010-02-09 Loctite (R&D) Limited Method of preparing electron deficient olefins in polar solvents
EP2069446B1 (en) * 2006-09-08 2010-03-17 3M Innovative Properties Company Color change cyanoacrylate adhesives
US7569719B1 (en) 2006-10-25 2009-08-04 Loctite (R&D) Limited Method of preparing electron deficient olefins
US7718821B1 (en) 2006-12-19 2010-05-18 Loctite (R&D) Limited Method of preparing electron deficient olefins
US7973119B1 (en) 2007-10-24 2011-07-05 Loctite (R&D) Limited Adhesive systems using imines and salts thereof and precursurs to electron deficient olefins
ES2662644T3 (en) * 2007-10-24 2018-04-09 Henkel IP & Holding GmbH Methylene reagents
US8053589B1 (en) 2007-10-24 2011-11-08 Henkel Ireland Limited Imines and methods of preparing electron deficient olefins using such novel imines
ES2634631T3 (en) * 2007-10-24 2017-09-28 Henkel IP & Holding GmbH Electron deficient olefins
EP2116126A1 (en) 2008-05-06 2009-11-11 Henkel AG & Co. KGaA Method and apparatus for grafting plants with fast-curing adhesives
US8207264B2 (en) * 2008-07-11 2012-06-26 Tyco Healthcare Group Lp Functionalized inclusion complexes as crosslinkers
EP2337825B1 (en) * 2008-09-26 2016-12-21 Henkel IP & Holding GmbH Cyanoacrylate compositions in non-flowable forms
US10196471B1 (en) 2008-10-24 2019-02-05 Henkel IP & Holding GmbH Curable composition having an electron deficient olefin
US8399698B1 (en) 2008-10-24 2013-03-19 Henkel Ireland Limited Substituted activated methylene reagents and methods of using such reagents to form electron deficient olefins
EP2424933B1 (en) 2009-05-01 2013-08-21 Henkel Ireland Limited Cyanoacrylate compositions
JP5618194B2 (en) * 2010-09-09 2014-11-05 国立大学法人筑波大学 Azacalix [3] pyridinium salt, method for producing the same, and method for producing polyalkylene glycol using the same
EP2511355B1 (en) 2011-04-12 2013-10-23 Henkel Ireland Ltd. Cyanoacrylate adhesive with improved water resistance
JP5878631B2 (en) * 2011-07-15 2016-03-08 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 Cyanoacrylate composition
JP6246734B2 (en) * 2012-01-25 2017-12-13 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 Cyanoacrylate composition
CN103980397B (en) * 2014-04-30 2016-02-24 中国科学院化学研究所 A kind of 3D printings composition and preparing and using method and goods
CN104193919A (en) * 2014-08-26 2014-12-10 太仓碧奇新材料研发有限公司 Polyethylene terephthalate composite material for 3D printing and preparation method thereof
GB2534548B (en) 2014-12-29 2020-08-12 Adv Med Solutions Ltd Adhesive applicator
TWI752043B (en) * 2016-06-28 2022-01-11 日商東亞合成股份有限公司 2-cyanoacrylate-based adhesive composition
GB2567868B (en) * 2017-10-27 2020-05-06 Henkel IP & Holding GmbH Toughened low odour cyanoacrylate compositions

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DE3209238A1 (en) * 1982-03-13 1983-09-15 Henkel KGaA, 4000 Düsseldorf ADHESIVES BASED ON CYANACRYLIC ACID ESTERS
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Also Published As

Publication number Publication date
CA2525011C (en) 2012-07-31
EP1633827A2 (en) 2006-03-15
MXPA05012296A (en) 2006-07-03
WO2004111147A3 (en) 2005-03-24
JP2006527782A (en) 2006-12-07
US6835789B1 (en) 2004-12-28
KR100964088B1 (en) 2010-06-16
KR20060024799A (en) 2006-03-17
WO2004111147A2 (en) 2004-12-23
BRPI0411472A (en) 2006-07-11
JP4624997B2 (en) 2011-02-02
US20040260045A1 (en) 2004-12-23
CN1791649B (en) 2010-05-26
CN1791649A (en) 2006-06-21

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Effective date: 20160620