DE3041843C2 - Verwendung von 9-Borabicyclo[3.3.1]-nonan und dessen Additionsprodukten an ethylenisch ungesättigte Verbindungen als Polymerisationsinitiatoren für Reaktionsklebstoffe auf Basis ethylenische Doppelbindungen enthaltender Systeme - Google Patents
Verwendung von 9-Borabicyclo[3.3.1]-nonan und dessen Additionsprodukten an ethylenisch ungesättigte Verbindungen als Polymerisationsinitiatoren für Reaktionsklebstoffe auf Basis ethylenische Doppelbindungen enthaltender SystemeInfo
- Publication number
- DE3041843C2 DE3041843C2 DE3041843A DE3041843A DE3041843C2 DE 3041843 C2 DE3041843 C2 DE 3041843C2 DE 3041843 A DE3041843 A DE 3041843A DE 3041843 A DE3041843 A DE 3041843A DE 3041843 C2 DE3041843 C2 DE 3041843C2
- Authority
- DE
- Germany
- Prior art keywords
- borabicyclo
- nonane
- polymerization initiators
- double bonds
- ethylenically unsaturated
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 14
- 239000003505 polymerization initiator Substances 0.000 title claims abstract description 8
- 239000004823 Reactive adhesive Substances 0.000 title claims description 5
- FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo(3.3.1)nonane Chemical compound C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 title description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 4
- 239000000853 adhesive Substances 0.000 abstract description 17
- 230000001070 adhesive effect Effects 0.000 abstract description 17
- 239000000203 mixture Substances 0.000 abstract description 7
- 150000001639 boron compounds Chemical class 0.000 abstract description 3
- 230000000379 polymerizing effect Effects 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 230000002269 spontaneous effect Effects 0.000 abstract 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 9
- 239000002023 wood Substances 0.000 description 8
- -1 triethylboron Chemical class 0.000 description 7
- 241001070947 Fagus Species 0.000 description 6
- 235000010099 Fagus sylvatica Nutrition 0.000 description 6
- 239000003999 initiator Substances 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 210000000988 bone and bone Anatomy 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 229920000193 polymethacrylate Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- DWHJJLTXBKSHJG-HWKANZROSA-N (e)-5-hydroxy-2-methylpent-2-enoic acid Chemical compound OC(=O)C(/C)=C/CCO DWHJJLTXBKSHJG-HWKANZROSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229940095102 methyl benzoate Drugs 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- AQRQHYITOOVBTO-UHFFFAOYSA-N 2-[2-[2-[2-(2-hydroxypropoxy)propoxy]propoxy]propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)COC(C)COC(C)CO AQRQHYITOOVBTO-UHFFFAOYSA-N 0.000 description 1
- UDXXYUDJOHIIDZ-UHFFFAOYSA-N 2-phosphonooxyethyl prop-2-enoate Chemical compound OP(O)(=O)OCCOC(=O)C=C UDXXYUDJOHIIDZ-UHFFFAOYSA-N 0.000 description 1
- UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 description 1
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- QVHMSMOUDQXMRS-UHFFFAOYSA-N PPG n4 Chemical compound CC(O)COC(C)COC(C)COC(C)CO QVHMSMOUDQXMRS-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- IBKYGLUKLLUABM-UHFFFAOYSA-N [O].COC(=O)C(C)=C Chemical compound [O].COC(=O)C(C)=C IBKYGLUKLLUABM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 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 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 210000004268 dentin Anatomy 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- QZSKYMMIFBLVGO-UHFFFAOYSA-N ethane-1,2-diol;2-methylprop-2-enoic acid Chemical compound OCCO.CC(=C)C(O)=O QZSKYMMIFBLVGO-UHFFFAOYSA-N 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- MCVVUJPXSBQTRZ-ONEGZZNKSA-N methyl (e)-but-2-enoate Chemical compound COC(=O)\C=C\C MCVVUJPXSBQTRZ-ONEGZZNKSA-N 0.000 description 1
- MRVWKSCQNHUHLZ-UHFFFAOYSA-N n-[2-(2-aminoethylamino)ethyl]prop-2-enamide Chemical compound NCCNCCNC(=O)C=C MRVWKSCQNHUHLZ-UHFFFAOYSA-N 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 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
- 239000000843 powder Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- 231100000732 tissue residue Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08K5/55—Boron-containing compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/30—Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
- A61K6/61—Cationic, anionic or redox initiators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/16—Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Plastic & Reconstructive Surgery (AREA)
- Dermatology (AREA)
- Transplantation (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Dental Preparations (AREA)
- Polymerization Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3041843A DE3041843C2 (de) | 1980-11-06 | 1980-11-06 | Verwendung von 9-Borabicyclo[3.3.1]-nonan und dessen Additionsprodukten an ethylenisch ungesättigte Verbindungen als Polymerisationsinitiatoren für Reaktionsklebstoffe auf Basis ethylenische Doppelbindungen enthaltender Systeme |
| DE8181109074T DE3163666D1 (en) | 1980-11-06 | 1981-10-28 | Process of curing reactive adhesives |
| AT81109074T ATE7510T1 (de) | 1980-11-06 | 1981-10-28 | Verfahren zum haerten von reaktionsklebstoffen. |
| EP81109074A EP0051797B1 (de) | 1980-11-06 | 1981-10-28 | Verfahren zum Härten von Reaktionsklebstoffen |
| JP56176591A JPS57108176A (en) | 1980-11-06 | 1981-11-05 | Reactive adhesive containing bron compound |
| US06/318,444 US4381386A (en) | 1980-11-06 | 1981-11-05 | Polymerizable adhesives containing boron initiators |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3041843A DE3041843C2 (de) | 1980-11-06 | 1980-11-06 | Verwendung von 9-Borabicyclo[3.3.1]-nonan und dessen Additionsprodukten an ethylenisch ungesättigte Verbindungen als Polymerisationsinitiatoren für Reaktionsklebstoffe auf Basis ethylenische Doppelbindungen enthaltender Systeme |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3041843A1 DE3041843A1 (de) | 1982-05-13 |
| DE3041843C2 true DE3041843C2 (de) | 1984-10-18 |
Family
ID=6116084
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3041843A Expired DE3041843C2 (de) | 1980-11-06 | 1980-11-06 | Verwendung von 9-Borabicyclo[3.3.1]-nonan und dessen Additionsprodukten an ethylenisch ungesättigte Verbindungen als Polymerisationsinitiatoren für Reaktionsklebstoffe auf Basis ethylenische Doppelbindungen enthaltender Systeme |
| DE8181109074T Expired DE3163666D1 (en) | 1980-11-06 | 1981-10-28 | Process of curing reactive adhesives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8181109074T Expired DE3163666D1 (en) | 1980-11-06 | 1981-10-28 | Process of curing reactive adhesives |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4381386A (enExample) |
| EP (1) | EP0051797B1 (enExample) |
| JP (1) | JPS57108176A (enExample) |
| AT (1) | ATE7510T1 (enExample) |
| DE (2) | DE3041843C2 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5914001B2 (ja) * | 1978-08-29 | 1984-04-02 | 株式会社クラレ | 歯科用材料 |
| DE3207263A1 (de) * | 1982-03-01 | 1983-09-08 | Henkel KGaA, 4000 Düsseldorf | Organo-borverbindungen enthaltende stoffgemische, verfahren zu ihrer herstellung und ihre verwendung |
| DE3201731A1 (de) * | 1982-01-21 | 1983-07-28 | Henkel KGaA, 4000 Düsseldorf | "aerob haertende kunststoffmassen" |
| DE3518965A1 (de) * | 1985-05-25 | 1986-11-27 | Henkel KGaA, 40589 Düsseldorf | Schmelzbare und dabei aerob aushaertende kunststoffmassen und verfahren zu ihrer herstellung |
| JPS61289006A (ja) * | 1985-06-17 | 1986-12-19 | Sunstar Inc | 歯科用接着性コ−テイングベ−ス組成物 |
| JP2887358B2 (ja) * | 1992-03-13 | 1999-04-26 | 三井化学株式会社 | 歯科用又は外科用接着充填剤 |
| BR9408536A (pt) * | 1994-02-22 | 1997-08-05 | Minnesota Mining & Mfg | Composição acrílica polimerizável compósito ligado processo para ligar entre si adesivamente dois substratos e para melhorar a adesão de um adesivo subsequentemente aplicado em um substrato de fluoroplástico |
| US5866632A (en) * | 1995-08-10 | 1999-02-02 | Sun Medical Co., Ltd. | Dental or surgical adhesive and polymerization initiator composition for the same |
| EP0889911B1 (en) | 1996-03-29 | 2000-11-02 | The Dow Chemical Company | Metallocene cocatalyst |
| JPH10302843A (ja) * | 1997-02-28 | 1998-11-13 | Mitsubishi Electric Corp | 電池用接着剤及びそれを用いた電池とその製造法 |
| DE19841342A1 (de) * | 1998-09-10 | 2000-04-20 | Merck Patent Gmbh | Neue Reaktivsysteme aus polymerisierbaren Monomeren , die Peroxide und stabilisierten Boralkylverbindungen enthalten |
| JP4538241B2 (ja) * | 2004-01-15 | 2010-09-08 | サンメディカル株式会社 | 歯科用接着剤およびそのための重合開始剤組成物 |
| JP5031180B2 (ja) * | 2004-03-29 | 2012-09-19 | サンメディカル株式会社 | 重合開始剤、それを用いたラジカル重合体の製造方法、ラジカル重合体およびラジカル重合性組成物 |
| CA2614050C (en) * | 2006-12-21 | 2015-04-21 | Hilti Aktiengesellschaft | Two-component reaction resin and method of fastening using the resin |
| TWI499429B (zh) * | 2012-11-26 | 2015-09-11 | Univ Nat Taiwan | 牙齒黏合劑及塗層劑 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT221813B (de) * | 1959-08-28 | 1962-06-25 | Solvay | Verfahren zur Polymerisation und bzw. oder Copolymerisation von eine Äthylendoppelbindung enthaltenden polaren Verbindungen |
| US3130185A (en) * | 1960-09-19 | 1964-04-21 | Union Carbide Corp | Trialkylboroxines as polymerization catalysts |
| US3452437A (en) * | 1964-11-06 | 1969-07-01 | Minnesota Mining & Mfg | Dental restorative material |
| JPS5137092B2 (enExample) * | 1972-04-28 | 1976-10-13 | ||
| JPS51123258A (en) * | 1975-04-19 | 1976-10-27 | Mochida Pharmaceut Co Ltd | Dental adherent composition for pretreating tooth face |
| US4182823A (en) * | 1978-08-18 | 1980-01-08 | National Starch And Chemical Corporation | Anionic polymerization inhibitor for cyanoacrylate adhesives |
-
1980
- 1980-11-06 DE DE3041843A patent/DE3041843C2/de not_active Expired
-
1981
- 1981-10-28 AT AT81109074T patent/ATE7510T1/de not_active IP Right Cessation
- 1981-10-28 EP EP81109074A patent/EP0051797B1/de not_active Expired
- 1981-10-28 DE DE8181109074T patent/DE3163666D1/de not_active Expired
- 1981-11-05 US US06/318,444 patent/US4381386A/en not_active Expired - Lifetime
- 1981-11-05 JP JP56176591A patent/JPS57108176A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0051797A1 (de) | 1982-05-19 |
| ATE7510T1 (de) | 1984-06-15 |
| JPH0212267B2 (enExample) | 1990-03-19 |
| EP0051797B1 (de) | 1984-05-16 |
| DE3163666D1 (en) | 1984-06-20 |
| JPS57108176A (en) | 1982-07-06 |
| DE3041843A1 (de) | 1982-05-13 |
| US4381386A (en) | 1983-04-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |