CH658255A5 - Verfahren zur herstellung von klebstoff auf basis eines methacrylat/diepoxid-polymerisationssystems. - Google Patents
Verfahren zur herstellung von klebstoff auf basis eines methacrylat/diepoxid-polymerisationssystems. Download PDFInfo
- Publication number
- CH658255A5 CH658255A5 CH451/84A CH45184A CH658255A5 CH 658255 A5 CH658255 A5 CH 658255A5 CH 451/84 A CH451/84 A CH 451/84A CH 45184 A CH45184 A CH 45184A CH 658255 A5 CH658255 A5 CH 658255A5
- Authority
- CH
- Switzerland
- Prior art keywords
- adhesive
- methacrylate
- polymerization
- stage
- component
- Prior art date
Links
- 239000000853 adhesive Substances 0.000 title claims description 40
- 230000001070 adhesive effect Effects 0.000 title claims description 40
- 238000006116 polymerization reaction Methods 0.000 title claims description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 238000000034 method Methods 0.000 claims description 18
- 230000003287 optical effect Effects 0.000 claims description 17
- -1 ester ethers Chemical class 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 9
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 8
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003822 epoxy resin Substances 0.000 claims description 7
- 229920000647 polyepoxide Polymers 0.000 claims description 7
- 239000012790 adhesive layer Substances 0.000 claims description 6
- 239000011521 glass Substances 0.000 claims description 5
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000003999 initiator Substances 0.000 claims description 5
- 238000010526 radical polymerization reaction Methods 0.000 claims description 5
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 claims description 4
- 230000008602 contraction Effects 0.000 claims description 4
- 239000010410 layer Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000001294 propane Substances 0.000 claims description 4
- 229910017048 AsF6 Inorganic materials 0.000 claims description 3
- 125000002091 cationic group Chemical group 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000012545 processing Methods 0.000 claims description 3
- 239000012955 diaryliodonium Substances 0.000 claims description 2
- 125000005520 diaryliodonium group Chemical group 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 6
- 150000002118 epoxides Chemical class 0.000 claims 4
- 239000000178 monomer Substances 0.000 claims 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 3
- 239000000975 dye Substances 0.000 claims 3
- 229920002554 vinyl polymer Polymers 0.000 claims 3
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 claims 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 2
- 238000012656 cationic ring opening polymerization Methods 0.000 claims 2
- 229920000193 polymethacrylate Polymers 0.000 claims 2
- 150000003254 radicals Chemical class 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- JPFPDGRVRGETED-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1COC(C)(C)O1 JPFPDGRVRGETED-UHFFFAOYSA-N 0.000 claims 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 claims 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 claims 1
- XXCVIFJHBFNFBO-UHFFFAOYSA-N 1-ethenoxyoctane Chemical compound CCCCCCCCOC=C XXCVIFJHBFNFBO-UHFFFAOYSA-N 0.000 claims 1
- NRDWOZOQMWQRIG-UHFFFAOYSA-N 2-(2-methylpropoxy)acridine Chemical compound C(C(C)C)OC1=CC2=CC3=CC=CC=C3N=C2C=C1 NRDWOZOQMWQRIG-UHFFFAOYSA-N 0.000 claims 1
- KFKRXESVMDBTNQ-UHFFFAOYSA-N 3-[18-(2-carboxylatoethyl)-8,13-bis(1-hydroxyethyl)-3,7,12,17-tetramethyl-22,23-dihydroporphyrin-21,24-diium-2-yl]propanoate Chemical compound N1C2=C(C)C(C(C)O)=C1C=C(N1)C(C)=C(C(O)C)C1=CC(C(C)=C1CCC(O)=O)=NC1=CC(C(CCC(O)=O)=C1C)=NC1=C2 KFKRXESVMDBTNQ-UHFFFAOYSA-N 0.000 claims 1
- 241001120493 Arene Species 0.000 claims 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims 1
- 230000001133 acceleration Effects 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 125000005410 aryl sulfonium group Chemical group 0.000 claims 1
- DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims 1
- 235000019400 benzoyl peroxide Nutrition 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000002131 composite material Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000010276 construction Methods 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 238000007334 copolymerization reaction Methods 0.000 claims 1
- 229920006037 cross link polymer Polymers 0.000 claims 1
- 150000004292 cyclic ethers Chemical class 0.000 claims 1
- 150000001993 dienes Chemical class 0.000 claims 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 229920001971 elastomer Polymers 0.000 claims 1
- 125000003700 epoxy group Chemical group 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 239000004744 fabric Substances 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 238000009434 installation Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 229940102838 methylmethacrylate Drugs 0.000 claims 1
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 229960002895 phenylbutazone Drugs 0.000 claims 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 claims 1
- 239000004033 plastic Substances 0.000 claims 1
- 229920003023 plastic Polymers 0.000 claims 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims 1
- 229920000728 polyester Polymers 0.000 claims 1
- 229920006254 polymer film Polymers 0.000 claims 1
- 239000004926 polymethyl methacrylate Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000007142 ring opening reaction Methods 0.000 claims 1
- 239000005060 rubber Substances 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 238000012719 thermal polymerization Methods 0.000 claims 1
- 238000007669 thermal treatment Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical class O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 5
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- SIJBDWPVNAYVGY-UHFFFAOYSA-N 2,2-dimethyl-1,3-dioxolane Chemical compound CC1(C)OCCO1 SIJBDWPVNAYVGY-UHFFFAOYSA-N 0.000 description 1
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical compound OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- TYPZZAUEUXWIRN-UHFFFAOYSA-N tert-butylbenzene hydroiodide Chemical class I.CC(C)(C)C1=CC=CC=C1.CC(C)(C)C1=CC=CC=C1 TYPZZAUEUXWIRN-UHFFFAOYSA-N 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/026—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from the reaction products of polyepoxides and unsaturated monocarboxylic acids, their anhydrides, halogenides or esters with low molecular weight
- C08F299/028—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from the reaction products of polyepoxides and unsaturated monocarboxylic acids, their anhydrides, halogenides or esters with low molecular weight photopolymerisable compositions
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C27/00—Joining pieces of glass to pieces of other inorganic material; Joining glass to glass other than by fusing
- C03C27/04—Joining glass to metal by means of an interlayer
- C03C27/048—Joining glass to metal by means of an interlayer consisting of an adhesive specially adapted for that purpose
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C27/00—Joining pieces of glass to pieces of other inorganic material; Joining glass to glass other than by fusing
- C03C27/06—Joining glass to glass by processes other than fusing
- C03C27/10—Joining glass to glass by processes other than fusing with the aid of adhesive specially adapted for that purpose
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Ceramic Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Geochemistry & Mineralogy (AREA)
- Materials Engineering (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD83247567A DD227861A3 (de) | 1983-01-31 | 1983-01-31 | Verfahren zur herstellung von klebstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH658255A5 true CH658255A5 (de) | 1986-10-31 |
Family
ID=5544662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH451/84A CH658255A5 (de) | 1983-01-31 | 1984-01-31 | Verfahren zur herstellung von klebstoff auf basis eines methacrylat/diepoxid-polymerisationssystems. |
Country Status (5)
| Country | Link |
|---|---|
| BG (1) | BG46081A1 (cs) |
| CH (1) | CH658255A5 (cs) |
| CS (1) | CS256916B1 (cs) |
| DD (1) | DD227861A3 (cs) |
| DE (1) | DE3339754A1 (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE55140T1 (de) * | 1987-02-12 | 1990-08-15 | Siemens Ag | Verfahren zum aushaerten von uv-haertenden materialien. |
| AU691083B2 (en) * | 1995-01-13 | 1998-05-07 | Minnesota Mining And Manufacturing Company | Method and composition for bonding components to glass |
| DE19727237C2 (de) * | 1996-07-05 | 1998-09-17 | Gsaenger Optoelektronik Gmbh | Kristallanordnung sowie deren Verwendung |
| DE10037626B4 (de) * | 2000-08-02 | 2005-07-07 | Weiss Chemie + Technik Gmbh & Co. Kg | Verbundsystem |
| US20050256219A1 (en) * | 2002-03-11 | 2005-11-17 | Hideaki Takase | Photocurable resin composition and optical component |
-
1983
- 1983-01-31 DD DD83247567A patent/DD227861A3/de not_active IP Right Cessation
- 1983-11-03 DE DE19833339754 patent/DE3339754A1/de not_active Withdrawn
- 1983-12-22 BG BG63546A patent/BG46081A1/xx unknown
- 1983-12-23 CS CS839884A patent/CS256916B1/cs unknown
-
1984
- 1984-01-31 CH CH451/84A patent/CH658255A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CS256916B1 (en) | 1988-04-15 |
| DE3339754A1 (de) | 1984-08-02 |
| BG46081A1 (en) | 1989-10-16 |
| DD227861A3 (de) | 1985-09-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |