CA2099347C - Cyanoacrylate adhesives with improved cured thermal properties - Google Patents
Cyanoacrylate adhesives with improved cured thermal propertiesInfo
- Publication number
- CA2099347C CA2099347C CA002099347A CA2099347A CA2099347C CA 2099347 C CA2099347 C CA 2099347C CA 002099347 A CA002099347 A CA 002099347A CA 2099347 A CA2099347 A CA 2099347A CA 2099347 C CA2099347 C CA 2099347C
- Authority
- CA
- Canada
- Prior art keywords
- formulation
- cyanoacrylate
- sulfur
- containing compound
- polymer
- 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 - Fee Related
Links
- 239000004830 Super Glue Substances 0.000 title description 16
- 239000000203 mixture Substances 0.000 claims abstract description 46
- 229920001651 Cyanoacrylate Polymers 0.000 claims abstract description 33
- 238000009472 formulation Methods 0.000 claims abstract description 31
- 239000000178 monomer Substances 0.000 claims abstract description 27
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229920000642 polymer Polymers 0.000 claims abstract description 24
- 239000000853 adhesive Substances 0.000 claims abstract description 22
- 230000001070 adhesive effect Effects 0.000 claims abstract description 22
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims abstract description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
- 239000011593 sulfur Substances 0.000 claims abstract description 14
- 230000002708 enhancing effect Effects 0.000 claims abstract description 5
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 15
- -1 sulfate compound Chemical class 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 230000004580 weight loss Effects 0.000 claims description 4
- 150000003462 sulfoxides Chemical class 0.000 claims description 3
- 125000002015 acyclic group Chemical group 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 1
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 description 16
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 description 10
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 239000004014 plasticizer Substances 0.000 description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000002562 thickening agent Substances 0.000 description 6
- 230000032683 aging Effects 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229920000800 acrylic rubber Polymers 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 229940053009 ethyl cyanoacrylate Drugs 0.000 description 4
- 229940098779 methanesulfonic acid Drugs 0.000 description 4
- 229920000058 polyacrylate Polymers 0.000 description 4
- WDXYVJKNSMILOQ-UHFFFAOYSA-N 1,3,2-dioxathiolane 2-oxide Chemical compound O=S1OCCO1 WDXYVJKNSMILOQ-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- IOODIIRXODOLHP-UHFFFAOYSA-N 1,3,2$l^{4}-benzodioxathiole 2-oxide Chemical compound C1=CC=C2OS(=O)OC2=C1 IOODIIRXODOLHP-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- CLHYKAZPWIRRRD-UHFFFAOYSA-N 1-hydroxypropane-1-sulfonic acid Chemical compound CCC(O)S(O)(=O)=O CLHYKAZPWIRRRD-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 230000003679 aging effect Effects 0.000 description 2
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 2
- VTJUKNSKBAOEHE-UHFFFAOYSA-N calixarene Chemical class COC(=O)COC1=C(CC=2C(=C(CC=3C(=C(C4)C=C(C=3)C(C)(C)C)OCC(=O)OC)C=C(C=2)C(C)(C)C)OCC(=O)OC)C=C(C(C)(C)C)C=C1CC1=C(OCC(=O)OC)C4=CC(C(C)(C)C)=C1 VTJUKNSKBAOEHE-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 description 2
- LMEDOLJKVASKTP-UHFFFAOYSA-N dibutyl sulfate Chemical compound CCCCOS(=O)(=O)OCCCC LMEDOLJKVASKTP-UHFFFAOYSA-N 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- TZSZOUXLMCRLSU-UHFFFAOYSA-N octane-1,2,7,8-tetrol Chemical compound OCC(O)CCCCC(O)CO TZSZOUXLMCRLSU-UHFFFAOYSA-N 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 150000003464 sulfur compounds Chemical class 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 150000008053 sultones Chemical class 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- 229940083957 1,2-butanediol Drugs 0.000 description 1
- LOWMYOWHQMKBTM-UHFFFAOYSA-N 1-butylsulfinylbutane Chemical compound CCCCS(=O)CCCC LOWMYOWHQMKBTM-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 240000007182 Ochroma pyramidale Species 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229910019891 RuCl3 Inorganic materials 0.000 description 1
- 229910006024 SO2Cl2 Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- NVJBFARDFTXOTO-UHFFFAOYSA-N diethyl sulfite Chemical compound CCOS(=O)OCC NVJBFARDFTXOTO-UHFFFAOYSA-N 0.000 description 1
- AAJJZALPFWYOQU-UHFFFAOYSA-N diethyl sulfite;dimethyl sulfite Chemical compound COS(=O)OC.CCOS(=O)OCC AAJJZALPFWYOQU-UHFFFAOYSA-N 0.000 description 1
- BDUPRNVPXOHWIL-UHFFFAOYSA-N dimethyl sulfite Chemical compound COS(=O)OC BDUPRNVPXOHWIL-UHFFFAOYSA-N 0.000 description 1
- ZUGPRXZCSHTXTE-UHFFFAOYSA-N diphenyl sulfate Chemical compound C=1C=CC=CC=1OS(=O)(=O)OC1=CC=CC=C1 ZUGPRXZCSHTXTE-UHFFFAOYSA-N 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229920001973 fluoroelastomer Polymers 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920006294 polydialkylsiloxane Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 239000012745 toughening agent Substances 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US913,139 | 1992-07-14 | ||
| US07/913,139 US5328944A (en) | 1992-07-14 | 1992-07-14 | Cyanoacrylate adhesives with improved cured thermal properties |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2099347A1 CA2099347A1 (en) | 1994-01-15 |
| CA2099347C true CA2099347C (en) | 1998-12-15 |
Family
ID=25432961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002099347A Expired - Fee Related CA2099347C (en) | 1992-07-14 | 1993-06-28 | Cyanoacrylate adhesives with improved cured thermal properties |
Country Status (15)
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69431642T2 (de) * | 1993-08-26 | 2003-07-10 | Teijin Ltd., Osaka | Process for production of stabilized polycarbonate |
| US6646354B2 (en) | 1997-08-22 | 2003-11-11 | Micron Technology, Inc. | Adhesive composition and methods for use in packaging applications |
| US6353268B1 (en) | 1997-08-22 | 2002-03-05 | Micron Technology, Inc. | Semiconductor die attachment method and apparatus |
| US6673192B1 (en) | 1997-09-25 | 2004-01-06 | Loctite Corporation | Multi-amine compound primers for bonding of polyolefins with cyanoacrylate adhesives |
| DE19750802A1 (de) | 1997-11-17 | 1999-05-20 | Henkel Kgaa | Stabilisierte Cyanacrylatklebstoffe |
| US6093780A (en) * | 1998-10-02 | 2000-07-25 | Loctite Corporation | Cyanoacrylate adhesive compositions with improved cured thermal properties |
| DE19859638A1 (de) | 1998-12-23 | 2000-07-20 | Henkel Kgaa | Aktivator für Cyanacrylat-Klebstoffe |
| EP2060978B1 (en) * | 2000-12-11 | 2013-02-13 | Linear Technology Corporation | Circuits and methods for interconnecting bus systems |
| US7431793B2 (en) | 2001-11-14 | 2008-10-07 | Loctite (R&D) Limited | Process for bonding substrates or parts and system including cyanoacrylate adhesive and accelerator composition |
| US6867241B2 (en) * | 2002-01-31 | 2005-03-15 | Henkel Corporation | Radiation-curable, cyanoacrylate-containing compositions |
| WO2003065841A1 (en) * | 2002-02-05 | 2003-08-14 | Henkel Corporation | Luminescing and/or fluorescing radiation-curable, cyanoacrylate-containing compositions |
| WO2005028629A2 (en) * | 2003-09-19 | 2005-03-31 | Applera Corporation | Whole genome expression analysis system |
| KR101273821B1 (ko) * | 2005-07-11 | 2013-06-11 | 헨켈 코포레이션 | 강화 시아노아크릴레이트 조성물 |
| US7659423B1 (en) | 2006-04-18 | 2010-02-09 | Loctite (R&D) Limited | Method of preparing electron deficient olefins in polar solvents |
| 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 |
| CA2703603A1 (en) * | 2007-10-24 | 2009-04-30 | Loctite (R&D) Limited | Electron deficient olefins |
| WO2009053482A2 (en) * | 2007-10-24 | 2009-04-30 | Loctite (R & D) Limited | Activated methylene reagents and curable compositions prepared therefrom |
| US8053589B1 (en) | 2007-10-24 | 2011-11-08 | Henkel Ireland Limited | Imines and methods of preparing electron deficient olefins using such novel imines |
| 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 |
| 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 |
| US10196471B1 (en) | 2008-10-24 | 2019-02-05 | Henkel IP & Holding GmbH | Curable composition having an electron deficient olefin |
| JP5177679B2 (ja) * | 2009-01-29 | 2013-04-03 | 田岡化学工業株式会社 | ２−シアノアクリレート系接着剤組成物 |
| EP2424933B1 (en) | 2009-05-01 | 2013-08-21 | Henkel Ireland Limited | Cyanoacrylate compositions |
| US10196543B2 (en) | 2011-03-31 | 2019-02-05 | Adhezion Biomedical, Llc | Fast bonding hair/eyelash extension adhesive compositions based on medical grade high viscosity cyanoacrylates |
| GB2544101B (en) * | 2015-11-06 | 2020-07-15 | Henkel IP & Holding GmbH | Rubber toughened cyanoacrylate compositions and uses thereof |
| GB2544272B (en) * | 2015-11-06 | 2020-02-19 | Henkel IP & Holding GmbH | Cyanoacrylate compositions |
| KR102282605B1 (ko) | 2016-03-01 | 2021-07-29 | 헨켈 아이피 앤드 홀딩 게엠베하 | 광경화성 전자 결핍 올레핀-함유 조성물 |
| GB2550846B (en) | 2016-05-23 | 2021-01-13 | Henkel IP & Holding GmbH | Two-part Cyanoacrylate curable adhesive system |
| GB2562107B (en) | 2017-05-05 | 2021-08-11 | Henkel IP & Holding GmbH | Cyanoacrylate compositions |
| EP4011993A4 (en) * | 2019-08-08 | 2023-07-19 | Toagosei Co., Ltd. | ADHESIVE COMPOSITION THAT DISINTEGRATES EASILY IN WATER |
| GB2596355B (en) | 2020-06-26 | 2022-09-28 | Henkel Ag & Co Kgaa | Cyanoacrylate compositions |
| GB2613555A (en) | 2021-12-03 | 2023-06-14 | Henkel IP & Holding GmbH | Method of underwater bonding |
Family Cites Families (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA845247A (en) * | 1970-06-23 | E.R. Squibb And Sons | Cyanoacrylate-silicon dioxide adhesive compositions | |
| US2665299A (en) * | 1952-05-07 | 1954-01-05 | Goodrich Co B F | Stabilized compositions comprising monomeric 1, 1-dicyano ethylene |
| US3355482A (en) * | 1966-06-20 | 1967-11-28 | Eastman Kodak Co | Stabilized cyanoacrylate adhesives |
| US3557185A (en) * | 1967-03-06 | 1971-01-19 | Toa Gosei Chem Ind | Stabilized alpha-cyanoacrylate adhesive compositions |
| CH540329A (de) * | 1967-11-10 | 1973-08-15 | Intercontinental Chem Co Ltd | Klebstoff |
| SE353344B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1967-11-10 | 1973-01-29 | Int Chem Co Ltd | |
| BE726628A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1968-01-10 | 1969-06-16 | ||
| US3652635A (en) * | 1968-08-09 | 1972-03-28 | Toa Gosei Chem Ind | Stabilized alpha-cyanoacrylate adhesive compositions |
| NL163797C (nl) * | 1969-10-10 | Loctite Ireland Ltd | Werkwijze voor het bereiden van hechtmiddelsamen- stellingen op basis van esters van alfa-cyaanacrylzuur, die een weekmaker bevatten. | |
| US3640792A (en) * | 1970-08-07 | 1972-02-08 | Rca Corp | Apparatus for chemically etching surfaces |
| IE35430B1 (en) * | 1971-01-06 | 1976-02-18 | Intercontinental Chem Co Ltd | High-viscosity cyanoacrylate adhesive compositions and processes for their preparation |
| IE36799B1 (en) * | 1971-12-14 | 1977-03-02 | Loctite Ltd | Cyanoacrylate adhesive composition |
| JPS4922432A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-06-21 | 1974-02-27 | ||
| JPS4922433A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-06-21 | 1974-02-27 | ||
| US3793221A (en) * | 1972-09-13 | 1974-02-19 | Basf Wyandotte Corp | Thickened acid cleaner |
| GB1413132A (en) * | 1972-10-20 | 1975-11-05 | Vni I Ispygatelny I Med Tekhn | Surgical adhesive |
| DE2349799C3 (de) * | 1973-10-04 | 1980-07-24 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Klebstoffe auf Basis von a - Cyanacrylsäure-Estern |
| US4196271A (en) * | 1975-12-24 | 1980-04-01 | Toagosei Chemical Industry Co., Ltd. | Adhesive composition |
| JPS5818955B2 (ja) * | 1975-12-27 | 1983-04-15 | 東亞合成株式会社 | セツチヤクザイソセイブツ |
| US4062827A (en) * | 1976-10-26 | 1977-12-13 | Eastman Kodak Company | Colored cyanoacrylate adhesive compositions |
| JPS6037836B2 (ja) * | 1977-08-05 | 1985-08-28 | 東亞合成株式会社 | 接着剤組成物 |
| US4139693A (en) * | 1978-03-29 | 1979-02-13 | National Starch And Chemical Corporation | 2-Cyanoacrylate adhesive compositions having enhanced bond strength |
| US4182823A (en) * | 1978-08-18 | 1980-01-08 | National Starch And Chemical Corporation | Anionic polymerization inhibitor for cyanoacrylate adhesives |
| JPS5536243A (en) * | 1978-09-05 | 1980-03-13 | Taoka Chem Co Ltd | Coloring of alpha-cyanoacrylate adhesive |
| JPS5566980A (en) * | 1978-11-14 | 1980-05-20 | Toagosei Chem Ind Co Ltd | Adhesive composition |
| JPS5566978A (en) * | 1978-11-15 | 1980-05-20 | Shion Kagaku Kogyo Kk | Ink for writing utensil |
| JPS565873A (en) * | 1979-06-29 | 1981-01-21 | Taoka Chem Co Ltd | Adhesive composition |
| US4377490A (en) * | 1979-06-29 | 1983-03-22 | Sumitomo Chemical Company, Limited | Adhesive composition |
| JPS5853676B2 (ja) * | 1979-12-24 | 1983-11-30 | 東亞合成株式会社 | 接着剤組成物 |
| AT365623B (de) * | 1980-03-10 | 1982-02-10 | Teroson Gmbh | Cyanoacrylat-klebstoffzusammensetzung |
| IE51863B1 (en) * | 1980-08-28 | 1987-04-15 | Loctite Corp | Additive for cyanoacrylate adhesives |
| US4405750A (en) * | 1981-03-31 | 1983-09-20 | Sumitomo Chemical Company, Ltd. | Colored cyanoacrylate adhesive composition |
| US4440910A (en) * | 1982-01-18 | 1984-04-03 | Loctite Corporation | Toughened cyanoacrylates containing elastomeric rubbers |
| DE3239776C2 (de) * | 1982-10-27 | 1987-01-02 | Teroson Gmbh, 6900 Heidelberg | Cyanacrylat-Klebstoffzusammensetzung |
| US4444933A (en) * | 1982-12-02 | 1984-04-24 | Borden, Inc. | Adhesive cyanoacrylate compositions with reduced adhesion to skin |
| JPS59147067A (ja) * | 1983-02-09 | 1984-08-23 | Alpha Giken:Kk | α−シアノアクリレ−ト系耐熱性瞬間接着剤組成物 |
| US4490051A (en) * | 1983-11-10 | 1984-12-25 | Gebruder Junghans Gmbh | Electromechanical short interval timer |
| US4560723A (en) * | 1983-11-14 | 1985-12-24 | Minnesota Mining And Manufacturing Company | Cyanoacrylate adhesive composition having sustained toughness |
| US4837260A (en) * | 1986-05-23 | 1989-06-06 | Toagosei Chemical Industry Co., Ltd. | Cyanoacrylate compositions |
| JP2955304B2 (ja) * | 1989-09-29 | 1999-10-04 | 株式会社ブリヂストン | 液体入りブツシユ形防振装置 |
-
1992
- 1992-07-14 US US07/913,139 patent/US5328944A/en not_active Expired - Fee Related
-
1993
- 1993-06-28 CA CA002099347A patent/CA2099347C/en not_active Expired - Fee Related
- 1993-07-09 JP JP19393993A patent/JP3164464B2/ja not_active Expired - Fee Related
- 1993-07-13 ES ES93305471T patent/ES2083826T3/es not_active Expired - Lifetime
- 1993-07-13 BR BR9302841A patent/BR9302841A/pt not_active Application Discontinuation
- 1993-07-13 DE DE69301381T patent/DE69301381T2/de not_active Expired - Lifetime
- 1993-07-13 DK DK93305471.0T patent/DK0579476T3/da active
- 1993-07-13 EP EP93305471A patent/EP0579476B1/en not_active Expired - Lifetime
- 1993-07-13 AT AT93305471T patent/ATE133440T1/de not_active IP Right Cessation
- 1993-07-13 MX MX9304227A patent/MX9304227A/es not_active IP Right Cessation
- 1993-07-13 KR KR1019930013129A patent/KR100227459B1/ko not_active Expired - Fee Related
- 1993-07-13 AU AU41891/93A patent/AU660099B2/en not_active Ceased
- 1993-07-20 TW TW082105758A patent/TW264510B/zh active
-
1996
- 1996-01-25 GR GR960400149T patent/GR3018793T3/el unknown
-
1998
- 1998-04-24 HK HK98103430A patent/HK1004280A1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR100227459B1 (ko) | 1999-11-01 |
| AU4189193A (en) | 1994-01-20 |
| BR9302841A (pt) | 1994-02-16 |
| EP0579476B1 (en) | 1996-01-24 |
| US5328944A (en) | 1994-07-12 |
| DE69301381T2 (de) | 1996-08-29 |
| ATE133440T1 (de) | 1996-02-15 |
| EP0579476A1 (en) | 1994-01-19 |
| JPH06108014A (ja) | 1994-04-19 |
| TW264510B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1995-12-01 |
| ES2083826T3 (es) | 1996-04-16 |
| MX9304227A (es) | 1995-01-31 |
| DE69301381D1 (de) | 1996-03-07 |
| GR3018793T3 (en) | 1996-04-30 |
| KR940005776A (ko) | 1994-03-22 |
| AU660099B2 (en) | 1995-06-08 |
| JP3164464B2 (ja) | 2001-05-08 |
| DK0579476T3 (da) | 1996-02-26 |
| CA2099347A1 (en) | 1994-01-15 |
| HK1004280A1 (en) | 1998-11-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |