CA1195022A - Adhesive compositions and bonding method employing the same - Google Patents
Adhesive compositions and bonding method employing the sameInfo
- Publication number
- CA1195022A CA1195022A CA000412357A CA412357A CA1195022A CA 1195022 A CA1195022 A CA 1195022A CA 000412357 A CA000412357 A CA 000412357A CA 412357 A CA412357 A CA 412357A CA 1195022 A CA1195022 A CA 1195022A
- Authority
- CA
- Canada
- Prior art keywords
- cation
- adhesive composition
- accordance
- alpha
- accelerator
- 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
- 239000000853 adhesive Substances 0.000 title claims abstract description 77
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 77
- 239000000203 mixture Substances 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims abstract description 18
- 150000001768 cations Chemical class 0.000 claims abstract description 39
- 239000000758 substrate Substances 0.000 claims abstract description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 150000001450 anions Chemical class 0.000 claims abstract description 29
- 230000002378 acidificating effect Effects 0.000 claims abstract description 18
- 239000000178 monomer Substances 0.000 claims abstract description 18
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical class OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000003381 stabilizer Substances 0.000 claims abstract description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000002023 wood Substances 0.000 claims description 21
- -1 methyl alpha-cyanacrylate Chemical compound 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 238000010526 radical polymerization reaction Methods 0.000 claims description 3
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 claims 4
- 125000001814 trioxo-lambda(7)-chloranyloxy group Chemical group *OCl(=O)(=O)=O 0.000 claims 4
- 125000001832 dioxo-lambda(5)-chloranyloxy group Chemical group *OCl(=O)=O 0.000 claims 2
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 claims 2
- ZCWKIFAQRXNZCH-UHFFFAOYSA-M tetramethylazanium;perchlorate Chemical compound C[N+](C)(C)C.[O-]Cl(=O)(=O)=O ZCWKIFAQRXNZCH-UHFFFAOYSA-M 0.000 claims 2
- MANNXDXMUHZSRP-UHFFFAOYSA-M tetramethylazanium;trifluoromethanesulfonate Chemical compound C[N+](C)(C)C.[O-]S(=O)(=O)C(F)(F)F MANNXDXMUHZSRP-UHFFFAOYSA-M 0.000 claims 2
- 229950010048 enbucrilate Drugs 0.000 claims 1
- SQGOMFWCSGKGEP-UHFFFAOYSA-N propan-2-yl 2-cyanoprop-2-enoate Chemical compound CC(C)OC(=O)C(=C)C#N SQGOMFWCSGKGEP-UHFFFAOYSA-N 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 150000002500 ions Chemical class 0.000 description 12
- 238000010998 test method Methods 0.000 description 10
- 241000208140 Acer Species 0.000 description 8
- 229920001651 Cyanoacrylate Polymers 0.000 description 5
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 239000004830 Super Glue Substances 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 150000008040 ionic compounds Chemical class 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000008053 sultones Chemical class 0.000 description 2
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000018185 Betula X alpestris Nutrition 0.000 description 1
- 235000018212 Betula X uliginosa Nutrition 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000219492 Quercus Species 0.000 description 1
- 244000180577 Sambucus australis Species 0.000 description 1
- 235000018734 Sambucus australis Nutrition 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229920000800 acrylic rubber Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229940107816 ammonium iodide Drugs 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006664 bond formation reaction Methods 0.000 description 1
- IUNCEDRRUNZACO-UHFFFAOYSA-N butyl(trimethyl)azanium Chemical compound CCCC[N+](C)(C)C IUNCEDRRUNZACO-UHFFFAOYSA-N 0.000 description 1
- 229960001948 caffeine Drugs 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001913 cellulose Chemical class 0.000 description 1
- 229920002678 cellulose Chemical class 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229940053009 ethyl cyanoacrylate Drugs 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 229920000058 polyacrylate Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- KLYDBHUQNXKACI-UHFFFAOYSA-M sodium;2-[2-(2-tridecoxyethoxy)ethoxy]ethyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCOCCOCCOCCOS([O-])(=O)=O KLYDBHUQNXKACI-UHFFFAOYSA-M 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- KBLZDCFTQSIIOH-UHFFFAOYSA-M tetrabutylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC KBLZDCFTQSIIOH-UHFFFAOYSA-M 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000010792 warming Methods 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
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
- C09J5/04—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving separate application of adhesive ingredients to the different surfaces to be joined
-
- 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US323,400 | 1981-11-20 | ||
| US06/323,400 US4460759A (en) | 1981-11-20 | 1981-11-20 | Adhesive compositions and bonding methods employing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1195022A true CA1195022A (en) | 1985-10-08 |
Family
ID=23259055
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000412357A Expired CA1195022A (en) | 1981-11-20 | 1982-09-28 | Adhesive compositions and bonding method employing the same |
Country Status (6)
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4533446A (en) * | 1983-07-20 | 1985-08-06 | Loctite (Ireland) Ltd. | Radiation-activatable anaerobic adhesive composition |
| US4718966A (en) * | 1984-01-30 | 1988-01-12 | Loctite (Ireland) Ltd. | Bonding method utilizing cyanoacrylate adhesive having calixarene accelerator |
| KR910001027B1 (ko) * | 1985-05-17 | 1991-02-19 | 와렌 그레고리 레자르 | 시아노아크릴레이트 중합 억제 조성물 |
| US5290825A (en) * | 1985-05-17 | 1994-03-01 | Lazar Warren G | Composition and method for inhibiting the cure of cyanoacrylate adhesives and cure inhibited cyanoacrylate adhesive compositions |
| JPH078977B2 (ja) * | 1986-07-02 | 1995-02-01 | セメダイン株式会社 | 接着方法 |
| CA1332658C (en) * | 1988-03-16 | 1994-10-25 | Ju Chao Liu | Primer for bonding low surface energy plastics with cyanoacrylate adhesives |
| US5079098A (en) * | 1988-03-16 | 1992-01-07 | Loctite Corporation | Primer for bonding low surface energy plastics with cyanoacrylate adhesives and bonding method employing same |
| US5066743A (en) * | 1989-03-27 | 1991-11-19 | Loctite Corporation | Two-part composition comprising a cyanoacrylate adhesive and a primer comprising a tertiary ammonium carboxylate compound |
| US4979993A (en) * | 1989-03-27 | 1990-12-25 | Loctite Corporation | Trialkylammonium alkyl carboxylate primer for cyanoacrylate bonding of polymeric substrates |
| JPH05179207A (ja) * | 1991-12-28 | 1993-07-20 | Nichias Corp | フリーアクセスフロアー板の製造方法 |
| US5643982A (en) * | 1994-10-13 | 1997-07-01 | Loctite Corporation | Non-ozone depleting co-solvent compositions |
| US5567266A (en) * | 1994-10-13 | 1996-10-22 | Loctite Corporation | Non-environmentally hazardous, non-volatile adhesive promoter composition for curing adhesives |
| US6001213A (en) * | 1994-10-13 | 1999-12-14 | Loctite Corporation | Methods for forming non-environmentally hazardous, non-volatile adhesive promoter compositions for curing adhesives |
| EP0918831A1 (en) * | 1996-08-16 | 1999-06-02 | Loctite (Ireland) Limited | Cyanoacrylate compositions with improved thermal and glass bonding performance |
| ATE230429T1 (de) | 1996-08-16 | 2003-01-15 | Loctite R & D Ltd | Cyanoakrylat klebezusammensetzungen zur glasleimung |
| DE19859638A1 (de) | 1998-12-23 | 2000-07-20 | Henkel Kgaa | Aktivator für Cyanacrylat-Klebstoffe |
| US6620846B1 (en) | 2000-08-02 | 2003-09-16 | Closure Medical Corporation | Absorbable adhesive compositions |
| US7569634B2 (en) * | 2002-02-14 | 2009-08-04 | The Glidden Company | Curable adhesive composition, adhesive kit and method of adhering substrates |
| US6765112B1 (en) * | 2003-03-25 | 2004-07-20 | E. I. Du Pont De Nemours And Company | Fluorinated onium salts |
| US8729121B2 (en) * | 2007-06-25 | 2014-05-20 | Adhezion Biomedical, Llc | Curing accelerator and method of making |
| WO2009064291A1 (en) | 2007-11-14 | 2009-05-22 | Spartan Medical Products, Llc | Cyanoacrylate tissue adhesives |
| US8293838B2 (en) * | 2008-06-20 | 2012-10-23 | Adhezion Biomedical, Llc | Stable and sterile tissue adhesive composition with a controlled high viscosity |
| US8198344B2 (en) | 2008-06-20 | 2012-06-12 | Adhezion Biomedical, Llc | Method of preparing adhesive compositions for medical use: single additive as both the thickening agent and the accelerator |
| US20110117047A1 (en) | 2008-06-23 | 2011-05-19 | Adhezion Biomedical, Llc | Cyanoacrylate tissue adhesives with desirable permeability and tensile strength |
| US9254133B2 (en) | 2008-10-31 | 2016-02-09 | Adhezion Biomedical, Llc | Sterilized liquid compositions of cyanoacrylate monomer mixtures |
| US8652510B2 (en) | 2008-10-31 | 2014-02-18 | Adhezion Biomedical, Llc | Sterilized liquid compositions of cyanoacrylate monomer mixtures |
| US8609128B2 (en) * | 2008-10-31 | 2013-12-17 | Adhezion Biomedical, Llc | Cyanoacrylate-based liquid microbial sealant drape |
| US9309019B2 (en) | 2010-05-21 | 2016-04-12 | Adhezion Biomedical, Llc | Low dose gamma sterilization of liquid adhesives |
| ES2443163T3 (es) | 2011-04-12 | 2014-02-18 | Henkel Ireland Ltd. | Adhesivo de cianoacrilato con resistencia al agua mejorada |
| TWI608069B (zh) * | 2012-09-11 | 2017-12-11 | 東亞合成股份有限公司 | 2-cyanoacrylate (salt) adhesive composition |
| JP6112121B2 (ja) * | 2012-12-14 | 2017-04-12 | 東亞合成株式会社 | 接着剤組成物 |
| JP6032193B2 (ja) * | 2012-12-26 | 2016-11-24 | 東亞合成株式会社 | ２−シアノアクリレート系接着剤組成物 |
| JP6354836B2 (ja) * | 2014-03-11 | 2018-07-11 | 東亞合成株式会社 | ２−シアノアクリレート系接着剤組成物 |
| JP6273538B2 (ja) * | 2014-03-12 | 2018-02-07 | 東亞合成株式会社 | ２−シアノアクリレート系接着剤組成物 |
| US9421297B2 (en) | 2014-04-02 | 2016-08-23 | Adhezion Biomedical, Llc | Sterilized compositions of cyanoacrylate monomers and naphthoquinone 2,3-oxides |
| JP6319897B2 (ja) * | 2014-05-27 | 2018-05-09 | 田岡化学工業株式会社 | ２−シアノアクリレート系接着剤用プライマー |
| TWI752043B (zh) * | 2016-06-28 | 2022-01-11 | 日商東亞合成股份有限公司 | 2-氰基丙烯酸酯系接著劑組成物 |
| US11603482B2 (en) | 2018-03-12 | 2023-03-14 | Donald W. Meyers | Polymer bonding process |
| US10577521B2 (en) * | 2018-03-12 | 2020-03-03 | Donald W. Meyers | Polymer bonding process |
| JP2024514387A (ja) | 2021-03-05 | 2024-04-02 | エイチ．ビー．フラー カンパニー | 害のない安定剤を有するシアノアクリレート組成物 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2768109A (en) * | 1954-06-02 | 1956-10-23 | Eastman Kodak Co | Alcohol-catalyzed alpha-cyanoacrylate adhesive compositions |
| US3260637A (en) * | 1960-10-19 | 1966-07-12 | Eastman Kodak Co | Method of bonding using amine solutions as catalysts with alpha-cyanoacrylate adhesives |
| US3640072A (en) * | 1968-07-20 | 1972-02-08 | Lutz Tilo Kayser | Rocket engine |
| IE36799B1 (en) * | 1971-12-14 | 1977-03-02 | Loctite Ltd | Cyanoacrylate adhesive composition |
| US3940362A (en) * | 1972-05-25 | 1976-02-24 | Johnson & Johnson | Cross-linked cyanoacrylate adhesive compositions |
| US3903055A (en) * | 1972-12-21 | 1975-09-02 | Johnson & Johnson | Method for initiating polymerization of cyanoacrylate monomers and comonomer blends thereof to give reproducible and predetermined gel/transition time characteristics |
| US4012402A (en) * | 1974-10-04 | 1977-03-15 | Johnson & Johnson | Modified cyanoacrylate monomers and methods for preparation |
| JPS5340027A (en) * | 1976-09-27 | 1978-04-12 | Toagosei Chem Ind Co Ltd | Primer for alpha-cyanoacrylate adhesive |
| US4042442A (en) * | 1976-11-29 | 1977-08-16 | Eastman Kodak Company | 2-Cyanoacrylate adhesive composition |
| JPS53129231A (en) * | 1977-04-19 | 1978-11-11 | Toagosei Chem Ind Co Ltd | Adhesion composition |
| JPS6037836B2 (ja) * | 1977-08-05 | 1985-08-28 | 東亞合成株式会社 | 接着剤組成物 |
| US4215173A (en) * | 1978-08-07 | 1980-07-29 | Pacer Technology And Resources | Bonded joints and method and material for forming same |
| JPS565873A (en) * | 1979-06-29 | 1981-01-21 | Taoka Chem Co Ltd | Adhesive composition |
| JPS5647474A (en) * | 1979-09-27 | 1981-04-30 | Taoka Chem Co Ltd | Bonding method |
| JPS5853676B2 (ja) * | 1979-12-24 | 1983-11-30 | 東亞合成株式会社 | 接着剤組成物 |
| JPS5887170A (ja) * | 1981-11-19 | 1983-05-24 | Toagosei Chem Ind Co Ltd | 接着剤組成物 |
-
1981
- 1981-11-20 US US06/323,400 patent/US4460759A/en not_active Expired - Fee Related
-
1982
- 1982-09-28 CA CA000412357A patent/CA1195022A/en not_active Expired
- 1982-10-26 EP EP82305680A patent/EP0080269B1/en not_active Expired
- 1982-10-26 DE DE8282305680T patent/DE3266224D1/de not_active Expired
- 1982-11-16 JP JP57199864A patent/JPS5889674A/ja active Granted
- 1982-11-19 BR BR8206690A patent/BR8206690A/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5889674A (ja) | 1983-05-28 |
| US4460759A (en) | 1984-07-17 |
| JPH0340751B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-06-19 |
| EP0080269A1 (en) | 1983-06-01 |
| DE3266224D1 (en) | 1985-10-17 |
| EP0080269B1 (en) | 1985-09-11 |
| BR8206690A (pt) | 1983-10-04 |
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry |