DE2201549B2 - Cyanoacrylat-Klebstoffzusammensetzung mit verbesserter Wärmebeständigkeit - Google Patents
Cyanoacrylat-Klebstoffzusammensetzung mit verbesserter WärmebeständigkeitInfo
- Publication number
- DE2201549B2 DE2201549B2 DE2201549A DE2201549A DE2201549B2 DE 2201549 B2 DE2201549 B2 DE 2201549B2 DE 2201549 A DE2201549 A DE 2201549A DE 2201549 A DE2201549 A DE 2201549A DE 2201549 B2 DE2201549 B2 DE 2201549B2
- Authority
- DE
- Germany
- Prior art keywords
- cyanoacrylate
- adhesive
- adhesive composition
- adhesives
- weight
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims description 28
- 239000004830 Super Glue Substances 0.000 title description 20
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 title description 16
- 239000000853 adhesive Substances 0.000 claims description 43
- 230000001070 adhesive effect Effects 0.000 claims description 43
- 150000002148 esters Chemical class 0.000 claims description 9
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000012360 testing method Methods 0.000 description 25
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 14
- 239000003112 inhibitor Substances 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- 239000003292 glue Substances 0.000 description 9
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 150000008065 acid anhydrides Chemical class 0.000 description 5
- ITCZEZQMUWEPQP-UHFFFAOYSA-N prop-2-enyl 2-cyanoprop-2-enoate Chemical compound C=CCOC(=O)C(=C)C#N ITCZEZQMUWEPQP-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 229920001651 Cyanoacrylate Polymers 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- -1 alkenyl radical Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-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
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 150000008053 sultones Chemical class 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZQHJVIHCDHJVII-OWOJBTEDSA-N (e)-2-chlorobut-2-enedioic acid Chemical compound OC(=O)\C=C(\Cl)C(O)=O ZQHJVIHCDHJVII-OWOJBTEDSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-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
- 125000001963 4 membered heterocyclic group Chemical group 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 229920001727 cellulose butyrate Polymers 0.000 description 1
- 238000005253 cladding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 description 1
- JJJFUHOGVZWXNQ-UHFFFAOYSA-N enbucrilate Chemical compound CCCCOC(=O)C(=C)C#N JJJFUHOGVZWXNQ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 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
- 229920002432 poly(vinyl methyl ether) polymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F22/30—Nitriles
-
- 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Table Devices Or Equipment (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IE39/71A IE34874B1 (en) | 1971-01-13 | 1971-01-13 | Cyanoacrylate adhesive compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2201549A1 DE2201549A1 (de) | 1973-08-02 |
| DE2201549B2 true DE2201549B2 (de) | 1979-10-18 |
Family
ID=11005773
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2201549A Withdrawn DE2201549B2 (de) | 1971-01-13 | 1972-01-13 | Cyanoacrylat-Klebstoffzusammensetzung mit verbesserter Wärmebeständigkeit |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3832334A (enExample) |
| JP (1) | JPS5212737B1 (enExample) |
| CA (1) | CA949249A (enExample) |
| DE (1) | DE2201549B2 (enExample) |
| FR (1) | FR2121825B1 (enExample) |
| GB (1) | GB1365195A (enExample) |
| IE (1) | IE34874B1 (enExample) |
| IT (1) | IT948171B (enExample) |
| NL (1) | NL173419C (enExample) |
| SE (1) | SE393117B (enExample) |
| SU (1) | SU574161A3 (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1467424A (en) * | 1973-06-16 | 1977-03-16 | Bostik Ltd | Adhesive compositions |
| US4134929A (en) * | 1976-07-23 | 1979-01-16 | Eastman Kodak Company | Allyl 2-cyanoacrylate-based orthodontic bracket adhesive |
| US4136138A (en) * | 1976-07-23 | 1979-01-23 | Eastman Kodak Company | Cyanoacrylate dental adhesive compositions |
| US4139693A (en) * | 1978-03-29 | 1979-02-13 | National Starch And Chemical Corporation | 2-Cyanoacrylate adhesive compositions having enhanced bond strength |
| US4444933A (en) * | 1982-12-02 | 1984-04-24 | Borden, Inc. | Adhesive cyanoacrylate compositions with reduced adhesion to skin |
| US4511686A (en) * | 1983-11-14 | 1985-04-16 | Minnesota Mining And Manufacturing Company | Cyanoacrylate adhesive composition containing tannins |
| JPS62153370A (ja) * | 1985-12-27 | 1987-07-08 | Alpha Giken:Kk | ２―シアノアクリレート系組成物および接着剤 |
| EP0585949B1 (de) * | 1992-09-04 | 1997-12-10 | Tomas Meinen | Verfahren und Vorrichtung zum Verarbeiten und Auftragen von Cyanacrylat-Klebstoffen |
| US5424343A (en) * | 1992-10-08 | 1995-06-13 | Loctite Corporation | Thermally resistant cyanoacrylates employing substituted napthasultone additive |
| US5288794A (en) * | 1992-10-23 | 1994-02-22 | Loctite Corporation | Cyanoacrylate adhesives with improved cured thermal properties utilizing substituted aromatic additive |
| 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 |
| US5861678A (en) | 1997-12-23 | 1999-01-19 | Micron Technology, Inc. | Method and system for attaching semiconductor dice to substrates |
| US6093780A (en) * | 1998-10-02 | 2000-07-25 | Loctite Corporation | Cyanoacrylate adhesive compositions with improved cured thermal properties |
| US6812296B1 (en) * | 2002-03-05 | 2004-11-02 | Newberth, Iii Frederick F. | Methods and compositions for incorporating free water into a sealant composition |
| DE10252564A1 (de) * | 2002-06-28 | 2004-01-22 | Polymaterials Ag | Kombination aus Baumaterial und Badflüssigkeit zur Verwendung in Rapid-Prototyping-Verfahren |
| US20060094833A1 (en) * | 2004-11-01 | 2006-05-04 | Loctite (R&D) Limited | Shock resistant cyanoacrylate compositions |
| US20070185229A1 (en) * | 2006-02-08 | 2007-08-09 | Bristol-Myers Squibb Company | Formulation for improving skin adhesive effectiveness |
| ES2706732T3 (es) | 2011-07-15 | 2019-04-01 | Henkel IP & Holding GmbH | Composiciones de cianoacrilato |
| US9657120B1 (en) | 2011-09-06 | 2017-05-23 | Henkel IP & Holding GmbH | Cyanoacrylate compositions |
| WO2013112315A1 (en) * | 2012-01-25 | 2013-08-01 | Henkel Corporation | Cyanoacrylate compositions |
| US9550883B2 (en) | 2012-01-25 | 2017-01-24 | Henkel IP & Holding GmbH | Cyanoacrylate compositions |
| US9783714B2 (en) | 2013-03-15 | 2017-10-10 | Henkel IP & Holding GmbH | Cyanoacrylate compositions |
| 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 |
| 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 |
| GB2567868B (en) | 2017-10-27 | 2020-05-06 | Henkel IP & Holding GmbH | Toughened low odour cyanoacrylate compositions |
| GB2576704B (en) | 2018-08-16 | 2022-01-12 | Henkel IP & Holding GmbH | Cyanoacrylate compositions |
| IT201900010053A1 (it) * | 2019-06-25 | 2020-12-25 | Permabond Eng Adhesives Ltd | Composizioni di adesivi cianoacrilici con resistenza migliorata alle alte temperature |
| GB2596355B (en) | 2020-06-26 | 2022-09-28 | Henkel Ag & Co Kgaa | Cyanoacrylate compositions |
| EP4194523A1 (en) | 2021-12-07 | 2023-06-14 | Cuantum Medical Cosmetics, S.L. | Cyanoacrylate adhesive composition |
-
1971
- 1971-01-13 IE IE39/71A patent/IE34874B1/xx unknown
- 1971-12-29 US US00213839A patent/US3832334A/en not_active Expired - Lifetime
-
1972
- 1972-01-04 CA CA131,596A patent/CA949249A/en not_active Expired
- 1972-01-05 SE SE7200112A patent/SE393117B/xx unknown
- 1972-01-10 IT IT47650/72A patent/IT948171B/it active
- 1972-01-11 SU SU7201736932A patent/SU574161A3/ru active
- 1972-01-12 NL NLAANVRAGE7200482,A patent/NL173419C/xx not_active IP Right Cessation
- 1972-01-13 FR FR727201109A patent/FR2121825B1/fr not_active Expired
- 1972-01-13 GB GB165472A patent/GB1365195A/en not_active Expired
- 1972-01-13 JP JP47006097A patent/JPS5212737B1/ja active Pending
- 1972-01-13 DE DE2201549A patent/DE2201549B2/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| NL173419C (nl) | 1984-01-16 |
| CA949249A (en) | 1974-06-11 |
| JPS5212737B1 (enExample) | 1977-04-09 |
| IE34874B1 (en) | 1975-09-03 |
| IT948171B (it) | 1973-05-30 |
| GB1365195A (en) | 1974-08-29 |
| NL7200482A (enExample) | 1972-07-17 |
| DE2201549A1 (de) | 1973-08-02 |
| FR2121825A1 (enExample) | 1972-08-25 |
| SE393117B (sv) | 1977-05-02 |
| US3832334A (en) | 1974-08-27 |
| FR2121825B1 (enExample) | 1974-06-21 |
| AU3780672A (en) | 1973-07-12 |
| NL173419B (nl) | 1983-08-16 |
| SU574161A3 (ru) | 1977-09-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8230 | Patent withdrawn |