CA1161586A - Prise de colles a base de caoutchouc par voie anaerobique - Google Patents

Prise de colles a base de caoutchouc par voie anaerobique

Info

Publication number: CA1161586A
Authority: CA; Canada
Prior art keywords: weight; range; article according; composition; group
Prior art date: 1979-10-19
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

CA000360082A

Other languages

English (en)

Inventor

James P. Moran, Jr.

Barbara B. Logvin

Frederick F. Newberth

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 Corp

Original Assignee

Henkel Loctite Corp

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.)

1979-10-19

Filing date

1980-09-11

Publication date

1984-01-31

1980-09-11 Application filed by Henkel Loctite Corp filed Critical Henkel Loctite Corp

1984-01-31 Application granted granted Critical

1984-01-31 Publication of CA1161586A publication Critical patent/CA1161586A/fr

Status Expired legal-status Critical Current

Links

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239000005060 rubber Substances 0.000 title claims abstract description 18
230000001070 adhesive effect Effects 0.000 title abstract description 8
239000000853 adhesive Substances 0.000 title abstract description 7
239000000178 monomer Substances 0.000 claims abstract description 34
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 49
239000000463 material Substances 0.000 claims description 43
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 24
229920001577 copolymer Polymers 0.000 claims description 19
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 18
239000003999 initiator Substances 0.000 claims description 17
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125000004432 carbon atom Chemical group C* 0.000 claims description 15
238000002360 preparation method Methods 0.000 claims description 14
239000004408 titanium dioxide Substances 0.000 claims description 12
150000003254 radicals Chemical group 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 10
239000011248 coating agent Substances 0.000 claims description 10
238000000576 coating method Methods 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
229920001778 nylon Polymers 0.000 claims description 10
239000004677 Nylon Substances 0.000 claims description 8
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
150000002978 peroxides Chemical class 0.000 claims description 7
239000003381 stabilizer Substances 0.000 claims description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
239000002202 Polyethylene glycol Substances 0.000 claims description 6
229920001223 polyethylene glycol Polymers 0.000 claims description 6
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical group COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 5
150000002432 hydroperoxides Chemical class 0.000 claims description 5
150000002791 naphthoquinones Chemical class 0.000 claims description 5
239000007787 solid Substances 0.000 claims description 5
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125000003277 amino group Chemical group 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 4
125000000864 peroxy group Chemical group O(O*)* 0.000 claims description 4
239000004215 Carbon black (E152) Substances 0.000 claims description 3
239000005062 Polybutadiene Substances 0.000 claims description 3
150000003857 carboxamides Chemical group 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
150000002429 hydrazines Chemical class 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
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150000002976 peresters Chemical class 0.000 claims description 3
150000002989 phenols Chemical class 0.000 claims description 3
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238000010526 radical polymerization reaction Methods 0.000 claims description 3
239000000565 sealant Substances 0.000 claims description 3
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150000003973 alkyl amines Chemical group 0.000 claims 2
125000002877 alkyl aryl group Chemical group 0.000 claims 2
125000003710 aryl alkyl group Chemical group 0.000 claims 2
UICBCXONCUFSOI-UHFFFAOYSA-N n'-phenylacetohydrazide Chemical group CC(=O)NNC1=CC=CC=C1 UICBCXONCUFSOI-UHFFFAOYSA-N 0.000 claims 2
229920001195 polyisoprene Polymers 0.000 claims 2
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical group C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims 2
235000019204 saccharin Nutrition 0.000 claims 2
239000002904 solvent Substances 0.000 abstract description 6
229920000126 latex Polymers 0.000 abstract description 3
239000004816 latex Substances 0.000 abstract description 3
238000007789 sealing Methods 0.000 abstract description 3
239000013047 polymeric layer Substances 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 14
239000000047 product Substances 0.000 description 12
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 11
229920003051 synthetic elastomer Polymers 0.000 description 8
239000005061 synthetic rubber Substances 0.000 description 8
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 7
238000000034 method Methods 0.000 description 7
125000003118 aryl group Chemical group 0.000 description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
239000001301 oxygen Substances 0.000 description 6
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239000007795 chemical reaction product Substances 0.000 description 5
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229920013646 Hycar Polymers 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
229920000572 Nylon 6/12 Polymers 0.000 description 4
239000004809 Teflon Substances 0.000 description 4
229920006362 Teflon® Polymers 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
239000011369 resultant mixture Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000008021 deposition Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000011521 glass Substances 0.000 description 3
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HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
125000001867 hydroperoxy group Chemical group [*]OO[H] 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000002156 mixing Methods 0.000 description 2
230000000704 physical effect Effects 0.000 description 2
229920000058 polyacrylate Polymers 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
150000004053 quinones Chemical class 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
239000002002 slurry Substances 0.000 description 2
238000003860 storage Methods 0.000 description 2
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
PVRSIFAEUCUJPK-UHFFFAOYSA-N (4-methoxyphenyl)hydrazine Chemical compound COC1=CC=C(NN)C=C1 PVRSIFAEUCUJPK-UHFFFAOYSA-N 0.000 description 1
WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 1
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 1
JFZBUNLOTDDXNY-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)propoxy]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)OCC(C)OC(=O)C(C)=C JFZBUNLOTDDXNY-UHFFFAOYSA-N 0.000 description 1
RIYDSTPQZDWTBD-UHFFFAOYSA-N 2-[2-[2-[2-(2-chloroprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-chloroprop-2-enoate Chemical compound ClC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(Cl)=C RIYDSTPQZDWTBD-UHFFFAOYSA-N 0.000 description 1
VRIWPZCNGVKMOF-UHFFFAOYSA-N 2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOCCO VRIWPZCNGVKMOF-UHFFFAOYSA-N 0.000 description 1
HQKURBRFOOUSNI-UHFFFAOYSA-N 2-[2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOCCOC(=O)C(C)=C HQKURBRFOOUSNI-UHFFFAOYSA-N 0.000 description 1
WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
HTWRFCRQSLVESJ-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCOC(=O)C(C)=C HTWRFCRQSLVESJ-UHFFFAOYSA-N 0.000 description 1
GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
229920006099 Vestamid® Polymers 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
230000001934 delay Effects 0.000 description 1
GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
210000005069 ears Anatomy 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229940071106 ethylenediaminetetraacetate Drugs 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
229940116336 glycol dimethacrylate Drugs 0.000 description 1
239000004519 grease Substances 0.000 description 1
238000007689 inspection Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
239000010705 motor oil Substances 0.000 description 1
GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
239000003973 paint Substances 0.000 description 1
239000012466 permeate Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
238000007639 printing Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 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
229940096522 trimethylolpropane triacrylate Drugs 0.000 description 1
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230000000007 visual effect Effects 0.000 description 1
238000004073 vulcanization Methods 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
- C09J109/00—Adhesives based on homopolymers or copolymers of conjugated diene hydrocarbons
- C09J109/02—Copolymers with acrylonitrile
- 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
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
- 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
- C08K5/14—Peroxides
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
- C08K5/24—Derivatives of hydrazine

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Compositions Of Macromolecular Compounds (AREA)
Adhesives Or Adhesive Processes (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Macromonomer-Based Addition Polymer (AREA)
Laminated Bodies (AREA)

CA000360082A 1979-10-19 1980-09-11 Prise de colles a base de caoutchouc par voie anaerobique Expired CA1161586A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US8633679A	1979-10-19	1979-10-19
US86,336		1979-10-19

Publications (1)

Publication Number	Publication Date
CA1161586A true CA1161586A (fr)	1984-01-31

Family

ID=22197915

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000360082A Expired CA1161586A (fr)	1979-10-19	1980-09-11	Prise de colles a base de caoutchouc par voie anaerobique

Country Status (12)

Country	Link
JP (1)	JPS5665065A (fr)
AU (1)	AU526311B2 (fr)
BR (1)	BR8006239A (fr)
CA (1)	CA1161586A (fr)
CH (1)	CH656888A5 (fr)
DE (1)	DE3039323C2 (fr)
ES (1)	ES495958A0 (fr)
FR (1)	FR2467875A1 (fr)
GB (1)	GB2060669B (fr)
IT (1)	IT1144012B (fr)
NL (1)	NL8005771A (fr)
SE (1)	SE8007228L (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH10237420A (ja) *	1997-02-20	1998-09-08	Three Bond Co Ltd	嫌気硬化性シール剤組成物
JP5501241B2 (ja) *	2007-10-29	2014-05-21	ヘンケルコーポレイション	耐熱性、嫌気硬化性組成物
KR101612585B1 (ko)	2009-04-08	2016-04-14	헨켈 아이피 앤드 홀딩 게엠베하	필름 형태의 혐기성 접착제 및 밀봉제 조성물, 필름 형태의 이러한 조성물을 함유하는 필름 스풀 조립체 및 교합가능한 부품 상에 예비도포된 그의 변형물
GB2546320B (en) *	2016-01-15	2018-02-14	Henkel IP & Holding GmbH	Cure of anaerobic compositions
GB2548918B (en) *	2016-04-01	2020-07-15	Henkel IP & Holding GmbH	Anaerobically curable (meth)acrylate compositions

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3625875A (en) *	1968-02-29	1971-12-07	Loctite Corp	Anaerobic adhesive and sealant compositions in nonflowable form
GB1505348A (en) *	1974-05-13	1978-03-30	Avdel Adhesives	Anaerobically curable compositions
US4243791A (en) *	1978-01-25	1981-01-06	Rocol Limited	Anaerobic adhesives

1980
- 1980-09-11 CA CA000360082A patent/CA1161586A/fr not_active Expired
- 1980-09-29 BR BR8006239A patent/BR8006239A/pt unknown
- 1980-10-03 JP JP13864380A patent/JPS5665065A/ja active Pending
- 1980-10-06 AU AU62986/80A patent/AU526311B2/en not_active Ceased
- 1980-10-07 IT IT49832/80A patent/IT1144012B/it active
- 1980-10-14 CH CH7642/80A patent/CH656888A5/de not_active IP Right Cessation
- 1980-10-15 SE SE8007228A patent/SE8007228L/xx not_active Application Discontinuation
- 1980-10-15 ES ES495958A patent/ES495958A0/es active Granted
- 1980-10-16 GB GB8033376A patent/GB2060669B/en not_active Expired
- 1980-10-17 FR FR8022267A patent/FR2467875A1/fr active Granted
- 1980-10-17 DE DE3039323A patent/DE3039323C2/de not_active Expired
- 1980-10-20 NL NL8005771A patent/NL8005771A/nl not_active Application Discontinuation

Also Published As

Publication number	Publication date
AU526311B2 (en)	1983-01-06
CH656888A5 (de)	1986-07-31
DE3039323A1 (de)	1981-05-07
IT8049832A0 (it)	1980-10-07
AU6298680A (en)	1981-04-30
FR2467875B1 (fr)	1985-02-15
JPS5665065A (en)	1981-06-02
GB2060669B (en)	1984-02-08
DE3039323C2 (de)	1985-07-18
SE8007228L (sv)	1981-04-20
BR8006239A (pt)	1981-04-22
NL8005771A (nl)	1981-04-22
ES8202858A1 (es)	1982-03-01
GB2060669A (en)	1981-05-07
FR2467875A1 (fr)	1981-04-30
ES495958A0 (es)	1982-03-01
IT1144012B (it)	1986-10-29

Legal Events

Date	Code	Title	Description
2001-01-31	MKEX	Expiry

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US20220119685A1 (en)	2022-04-21	Pressure-sensitive adhesive sheet
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EP0576544A1 (fr)	1994-01-05	Compositions de matiere auto-adhesive a base d'acrylate/de silicone et durcissable par rayonnement.
EP0342808A1 (fr)	1989-11-23	Adhésif collant sensible à la pression
CA1161586A (fr)	1984-01-31	Prise de colles a base de caoutchouc par voie anaerobique
JP2024515112A (ja)	2024-04-04	嫌気硬化性組成物
US4151055A (en)	1979-04-24	Radiation curable adhesive compositions
US4591618A (en)	1986-05-27	Anaerobic adhesive composition comprising modified unsaturated polymer and (meth)acrylic acid
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US4138449A (en)	1979-02-06	Anaerobic curing compositions
US4432848A (en)	1984-02-21	Radiation cured, high temperature pressure-sensitive adhesive
JP3052972B2 (ja)	2000-06-19	感圧性接着剤とその接着シ―ト類
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CA2267130C (fr)	2003-10-14	Adhesif autocollant et materiau de protection de surface
JPS6026079A (ja)	1985-02-08	感圧接着剤の改質方法
GB1561180A (en)	1980-02-13	Nontacky coating and adhesive compositions
WO2025186335A1 (fr)	2025-09-12	Composition durcissable double