CA1231085A - Structural adhesive formulations - Google Patents
Structural adhesive formulationsInfo
- Publication number
- CA1231085A CA1231085A CA000476884A CA476884A CA1231085A CA 1231085 A CA1231085 A CA 1231085A CA 000476884 A CA000476884 A CA 000476884A CA 476884 A CA476884 A CA 476884A CA 1231085 A CA1231085 A CA 1231085A
- Authority
- CA
- Canada
- Prior art keywords
- group
- weight
- monomer
- polymeric material
- percent
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 107
- 239000000853 adhesive Substances 0.000 title claims description 67
- 230000001070 adhesive effect Effects 0.000 title claims description 67
- 238000009472 formulation Methods 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 17
- 239000003522 acrylic cement Substances 0.000 claims abstract description 7
- 150000003573 thiols Chemical class 0.000 claims abstract description 5
- 239000000178 monomer Substances 0.000 claims description 95
- 239000000463 material Substances 0.000 claims description 92
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 50
- 229920001577 copolymer Polymers 0.000 claims description 32
- 229920000642 polymer Polymers 0.000 claims description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 28
- 239000006188 syrup Substances 0.000 claims description 27
- 235000020357 syrup Nutrition 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 229920001519 homopolymer Polymers 0.000 claims description 21
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 19
- 239000007795 chemical reaction product Substances 0.000 claims description 15
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 claims description 13
- 239000012948 isocyanate Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 229920002554 vinyl polymer Polymers 0.000 claims description 11
- 229920001971 elastomer Polymers 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 10
- 150000002894 organic compounds Chemical class 0.000 claims description 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 9
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 150000002513 isocyanates Chemical class 0.000 claims description 9
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 9
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 8
- 150000002432 hydroperoxides Chemical class 0.000 claims description 8
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 8
- 238000007334 copolymerization reaction Methods 0.000 claims description 7
- 150000002484 inorganic compounds Chemical class 0.000 claims description 7
- 125000001741 organic sulfur group Chemical group 0.000 claims description 7
- 239000011145 styrene acrylonitrile resin Substances 0.000 claims description 7
- 229920006337 unsaturated polyester resin Polymers 0.000 claims description 7
- 150000003673 urethanes Chemical class 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000000806 elastomer Substances 0.000 claims description 6
- 239000013536 elastomeric material Substances 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 5
- 230000013011 mating Effects 0.000 claims description 4
- 230000033116 oxidation-reduction process Effects 0.000 claims description 3
- 150000002736 metal compounds Chemical class 0.000 claims description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims 4
- 150000005215 alkyl ethers Chemical class 0.000 claims 3
- 229960003280 cupric chloride Drugs 0.000 claims 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims 1
- 150000002902 organometallic compounds Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 8
- -1 unsaturated dicarboxylic acid ester Chemical class 0.000 description 39
- 229920000180 alkyd Polymers 0.000 description 29
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 25
- 150000003254 radicals Chemical class 0.000 description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- 150000003440 styrenes Chemical class 0.000 description 13
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 229920005862 polyol Polymers 0.000 description 11
- 150000003077 polyols Chemical class 0.000 description 11
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 9
- 150000002927 oxygen compounds Chemical class 0.000 description 9
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 8
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 7
- 229920001228 polyisocyanate Polymers 0.000 description 7
- 239000005056 polyisocyanate Substances 0.000 description 7
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- 208000037062 Polyps Diseases 0.000 description 6
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 229940106691 bisphenol a Drugs 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 150000003464 sulfur compounds Chemical class 0.000 description 5
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 4
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 4
- 235000011007 phosphoric acid Nutrition 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- 235000009434 Actinidia chinensis Nutrition 0.000 description 3
- 235000009436 Actinidia deliciosa Nutrition 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 230000000712 assembly Effects 0.000 description 3
- 238000000429 assembly Methods 0.000 description 3
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical class CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 2
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 2
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 2
- PSYGHMBJXWRQFD-UHFFFAOYSA-N 2-(2-sulfanylacetyl)oxyethyl 2-sulfanylacetate Chemical compound SCC(=O)OCCOC(=O)CS PSYGHMBJXWRQFD-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 2
- UGWULZWUXSCWPX-UHFFFAOYSA-N 2-sulfanylideneimidazolidin-4-one Chemical compound O=C1CNC(=S)N1 UGWULZWUXSCWPX-UHFFFAOYSA-N 0.000 description 2
- QPOZGXKWWKLJDK-UHFFFAOYSA-N 6-nitro-3h-1,3-benzothiazole-2-thione Chemical compound [O-][N+](=O)C1=CC=C2NC(=S)SC2=C1 QPOZGXKWWKLJDK-UHFFFAOYSA-N 0.000 description 2
- 244000298715 Actinidia chinensis Species 0.000 description 2
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- 241000282320 Panthera leo Species 0.000 description 2
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- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
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- GNBVPFITFYNRCN-UHFFFAOYSA-M sodium thioglycolate Chemical compound [Na+].[O-]C(=O)CS GNBVPFITFYNRCN-UHFFFAOYSA-M 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- RIPYNJLMMFGZSX-UHFFFAOYSA-N (5-benzoylperoxy-2,5-dimethylhexan-2-yl) benzenecarboperoxoate Chemical compound C=1C=CC=CC=1C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C1=CC=CC=C1 RIPYNJLMMFGZSX-UHFFFAOYSA-N 0.000 description 1
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- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 1
- PQCQUHTVHDSFDH-UHFFFAOYSA-N 2-[ethoxy(hydroxy)phosphoryl]oxyethyl prop-2-enoate Chemical compound CCOP(O)(=O)OCCOC(=O)C=C PQCQUHTVHDSFDH-UHFFFAOYSA-N 0.000 description 1
- WAJJFPMYKWCDNI-UHFFFAOYSA-N 2-[hydroxy(2-prop-2-enoyloxyethoxy)phosphoryl]oxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOP(=O)(O)OCCOC(=O)C=C WAJJFPMYKWCDNI-UHFFFAOYSA-N 0.000 description 1
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- CXOHVCKJGLFRKZ-AATRIKPKSA-N tert-butyl (e)-but-2-eneperoxoate Chemical compound C\C=C\C(=O)OOC(C)(C)C CXOHVCKJGLFRKZ-AATRIKPKSA-N 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
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- 239000011135 tin Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
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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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09J175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
-
- 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
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/40—Redox systems
-
- 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
- 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
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
- Graft Or Block Polymers (AREA)
- Catalysts (AREA)
- Polymerization Catalysts (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61474884A | 1984-05-29 | 1984-05-29 | |
| US614,748 | 1984-05-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1231085A true CA1231085A (en) | 1988-01-05 |
Family
ID=24462548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000476884A Expired CA1231085A (en) | 1984-05-29 | 1985-03-19 | Structural adhesive formulations |
Country Status (11)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5391602A (en) * | 1993-11-30 | 1995-02-21 | National Starch And Chemical Investment Holding Corporation | Radiation-cured pressure sensitive adhesives |
| US6812308B2 (en) | 2000-11-21 | 2004-11-02 | 3M Innovative Properties Company | Initiator systems and adhesive compositions made therewith |
| US6383655B1 (en) | 1998-06-12 | 2002-05-07 | 3M Innovative Properties Company | Low odor polymerizable compositions useful for bonding low surface energy substrates |
| EP1098943B1 (en) * | 1998-06-12 | 2004-01-21 | Minnesota Mining And Manufacturing Company | Low odor polymerizable compositions useful for bonding low surface energy substrates |
| US6479602B1 (en) | 2000-03-15 | 2002-11-12 | 3M Innovative Properties | Polymerization initiator systems and bonding compositions comprising vinyl aromatic compounds |
| DE102014103920A1 (de) | 2013-04-05 | 2014-10-09 | Fischerwerke Gmbh & Co. Kg | Biogene flüssige nichtreaktive Verdünner in Kunstharz-Verklebungs mitteln |
| CN106398552A (zh) * | 2015-07-30 | 2017-02-15 | 电气化学工业株式会社 | 组合物和粘合剂组合物 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB674144A (en) * | 1949-05-12 | 1952-06-18 | Phillips Petroleum Co | Improvements in or relating to process of producing polymers of high molecular weight |
| GB685855A (en) * | 1950-03-02 | 1953-01-14 | Turley & Williams Ltd | Improvements in and connected with gas burners |
| GB714868A (en) * | 1951-12-24 | 1954-09-01 | Dental Fillings Ltd | Improvements in or relating to polymerisation products |
| GB766562A (en) * | 1954-02-04 | 1957-01-23 | British Geon Ltd | Polymerisation process |
| BE537434A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1954-05-07 | |||
| US2834760A (en) * | 1954-12-14 | 1958-05-13 | Polymer Corp | Redox type polymerization |
| GB829213A (en) * | 1956-02-09 | 1960-03-02 | Hercules Powder Co Ltd | Improvements in or relating to low temperature emulsion polymerization of unsaturated compounds |
| NL243459A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1958-09-22 | |||
| NL128613C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1960-03-03 | |||
| BE607559A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1960-08-26 | |||
| US3084068A (en) * | 1960-11-08 | 1963-04-02 | Du Pont | Process for acrylic polymerizations |
| NL271517A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1960-11-17 | |||
| NL280929A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1961-07-17 | |||
| FR1463520A (fr) * | 1965-01-13 | 1966-12-23 | Du Pont | Procédé de polymérisation d'esters de l'acide méthacrylique, catalyseurs-accélérateurs pour la mise en oeuvre de ce procédé et articles conformés obtenus à l'aide de ceux-ci |
| GB1170983A (en) * | 1967-08-04 | 1969-11-19 | Bp Chem Int Ltd | Process for the Production of Cured Products. |
| NL155270B (nl) * | 1967-12-19 | 1977-12-15 | Chatillon Italiana Fibre | Werkwijze voor het polymeriseren in de massa van vinylchloride, eventueel gemengd met ten minste een ander copolymeriseerbaar monomeer. |
| DE2046086C3 (de) * | 1970-09-18 | 1983-11-17 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Acrylnitrilcopolymerisaten |
| NL7609074A (nl) * | 1976-08-16 | 1978-02-20 | Akzo Nv | Werkwijze ter bereiding van sbr-rubbers. |
| US4223115A (en) * | 1978-04-24 | 1980-09-16 | Lord Corporation | Structural adhesive formulations |
| GB2060660B (en) * | 1979-10-18 | 1983-11-23 | Bostik Ltd | Adhesives containing pyrazoline activators |
-
1985
- 1985-03-19 CA CA000476884A patent/CA1231085A/en not_active Expired
- 1985-03-20 ZA ZA852098A patent/ZA852098B/xx unknown
- 1985-03-21 GB GB08507298A patent/GB2159525B/en not_active Expired
- 1985-03-21 EP EP85301966A patent/EP0167223B1/en not_active Expired
- 1985-03-21 AT AT85301966T patent/ATE34763T1/de not_active IP Right Cessation
- 1985-04-11 NO NO851454A patent/NO851454L/no unknown
- 1985-04-24 JP JP60086622A patent/JPS60258205A/ja active Pending
- 1985-05-22 DE DE19853518438 patent/DE3518438A1/de active Granted
- 1985-05-28 DK DK235985A patent/DK235985A/da not_active Application Discontinuation
- 1985-05-28 FR FR8507976A patent/FR2565595B1/fr not_active Expired
- 1985-05-28 KR KR1019850003653A patent/KR850008501A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| ZA852098B (en) | 1986-01-29 |
| DE3518438A1 (de) | 1985-12-05 |
| KR850008501A (ko) | 1985-12-18 |
| ATE34763T1 (de) | 1988-06-15 |
| NO851454L (no) | 1985-12-02 |
| GB8507298D0 (en) | 1985-05-01 |
| JPS60258205A (ja) | 1985-12-20 |
| FR2565595A1 (fr) | 1985-12-13 |
| DE3518438C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-12-13 |
| EP0167223B1 (en) | 1988-06-01 |
| DK235985D0 (da) | 1985-05-28 |
| FR2565595B1 (fr) | 1987-10-09 |
| DK235985A (da) | 1985-11-30 |
| GB2159525B (en) | 1988-03-02 |
| GB2159525A (en) | 1985-12-04 |
| EP0167223A1 (en) | 1986-01-08 |
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