DE2646416A1 - Durch uv-licht polymerisierbare massen auf basis von acrylsaeureester - Google Patents
Durch uv-licht polymerisierbare massen auf basis von acrylsaeureesterInfo
- Publication number
- DE2646416A1 DE2646416A1 DE19762646416 DE2646416A DE2646416A1 DE 2646416 A1 DE2646416 A1 DE 2646416A1 DE 19762646416 DE19762646416 DE 19762646416 DE 2646416 A DE2646416 A DE 2646416A DE 2646416 A1 DE2646416 A1 DE 2646416A1
- Authority
- DE
- Germany
- Prior art keywords
- benzoin
- phosphite
- weight
- polymerization
- ether
- 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- Withdrawn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
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 title claims abstract description 80
- 244000028419 Styrax benzoin Species 0.000 title claims abstract description 33
- 235000000126 Styrax benzoin Nutrition 0.000 title claims abstract description 33
- 235000008411 Sumatra benzointree Nutrition 0.000 title claims abstract description 33
- 229960002130 benzoin Drugs 0.000 title claims abstract description 33
- 235000019382 gum benzoic Nutrition 0.000 title claims abstract description 33
- 239000012190 activator Substances 0.000 title claims abstract description 5
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 title abstract description 32
- -1 acrylic ester Chemical class 0.000 title abstract description 28
- 231100000489 sensitizer Toxicity 0.000 title 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000945 filler Substances 0.000 claims abstract description 11
- 239000003999 initiator Substances 0.000 claims abstract description 10
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003381 stabilizer Substances 0.000 claims abstract description 7
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 32
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical class CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 claims description 6
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 20
- 239000000463 material Substances 0.000 abstract description 8
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000654 additive Substances 0.000 abstract description 5
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 abstract description 5
- 239000011248 coating agent Substances 0.000 abstract description 4
- 238000000576 coating method Methods 0.000 abstract description 3
- 238000007789 sealing Methods 0.000 abstract description 3
- LMWVCJZYRYMGSL-UHFFFAOYSA-N 2-methylprop-2-enoic acid;propane Chemical compound CCC.CC(=C)C(O)=O.CC(=C)C(O)=O LMWVCJZYRYMGSL-UHFFFAOYSA-N 0.000 abstract 1
- 208000002925 dental caries Diseases 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 description 52
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 16
- 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 14
- 150000001875 compounds Chemical class 0.000 description 13
- 238000000034 method Methods 0.000 description 11
- 239000010453 quartz Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 9
- XBLRPWWTIKQRQI-UHFFFAOYSA-N CCCCCCCCCCC1=CC=CC(P(O)(O)O)=C1CCCCCCCCCC Chemical compound CCCCCCCCCCC1=CC=CC(P(O)(O)O)=C1CCCCCCCCCC XBLRPWWTIKQRQI-UHFFFAOYSA-N 0.000 description 8
- SPLAVQGQXNFORD-UHFFFAOYSA-N methyl 4-methoxy-5-oxo-4,5-diphenylpentanoate Chemical compound COC(C(C1=CC=CC=C1)=O)(C1=CC=CC=C1)CCC(=O)OC SPLAVQGQXNFORD-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 230000005855 radiation Effects 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 6
- 230000001133 acceleration Effects 0.000 description 5
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 5
- 229920006305 unsaturated polyester Polymers 0.000 description 5
- DZZAHLOABNWIFA-UHFFFAOYSA-N 2-butoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCC)C(=O)C1=CC=CC=C1 DZZAHLOABNWIFA-UHFFFAOYSA-N 0.000 description 4
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 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 description 3
- DIVXVZXROTWKIH-UHFFFAOYSA-N 2-hydroxy-1,2-diphenylpropan-1-one Chemical compound C=1C=CC=CC=1C(O)(C)C(=O)C1=CC=CC=C1 DIVXVZXROTWKIH-UHFFFAOYSA-N 0.000 description 3
- CFMSRWFPFKCHCR-UHFFFAOYSA-N 4-methoxy-5-oxo-4,5-diphenylpentanenitrile Chemical compound COC(C(C1=CC=CC=C1)=O)(C1=CC=CC=C1)CCC#N CFMSRWFPFKCHCR-UHFFFAOYSA-N 0.000 description 3
- HINPQOHOYSXOAP-UHFFFAOYSA-N 4-methoxy-5-oxo-4,5-diphenylpentanoic acid Chemical compound C=1C=CC=CC=1C(CCC(O)=O)(OC)C(=O)C1=CC=CC=C1 HINPQOHOYSXOAP-UHFFFAOYSA-N 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- 206010070834 Sensitisation Diseases 0.000 description 3
- 239000006059 cover glass Substances 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- NMAKPIATXQEXBT-UHFFFAOYSA-N didecyl phenyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OC1=CC=CC=C1 NMAKPIATXQEXBT-UHFFFAOYSA-N 0.000 description 3
- XMQYIPNJVLNWOE-UHFFFAOYSA-N dioctyl hydrogen phosphite Chemical compound CCCCCCCCOP(O)OCCCCCCCC XMQYIPNJVLNWOE-UHFFFAOYSA-N 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 150000003003 phosphines Chemical class 0.000 description 3
- 150000008301 phosphite esters Chemical class 0.000 description 3
- 230000002028 premature Effects 0.000 description 3
- 230000008313 sensitization Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 3
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 3
- 229920006337 unsaturated polyester resin Polymers 0.000 description 3
- WDFCIMPKVFWSRF-UHFFFAOYSA-N (2,3-didecylphenyl) dihydrogen phosphite Chemical compound CCCCCCCCCCC1=CC=CC(OP(O)O)=C1CCCCCCCCCC WDFCIMPKVFWSRF-UHFFFAOYSA-N 0.000 description 2
- NICBEWDPKDDXRY-UHFFFAOYSA-N 1,2-diphenyl-2-trimethylsilyloxyethanone Chemical compound C=1C=CC=CC=1C(O[Si](C)(C)C)C(=O)C1=CC=CC=C1 NICBEWDPKDDXRY-UHFFFAOYSA-N 0.000 description 2
- AVDOODBEVYTHNU-UHFFFAOYSA-N 1,2-diphenyl-2-trimethylsilyloxypropan-1-one Chemical compound C=1C=CC=CC=1C(O[Si](C)(C)C)(C)C(=O)C1=CC=CC=C1 AVDOODBEVYTHNU-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- KUMNEOGIHFCNQW-UHFFFAOYSA-N diphenyl phosphite Chemical compound C=1C=CC=CC=1OP([O-])OC1=CC=CC=C1 KUMNEOGIHFCNQW-UHFFFAOYSA-N 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000005461 organic phosphorous group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 2
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- QOPBTFMUVTXWFF-UHFFFAOYSA-N tripropyl phosphite Chemical compound CCCOP(OCCC)OCCC QOPBTFMUVTXWFF-UHFFFAOYSA-N 0.000 description 2
- 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
- IMAHLMWOKFATMM-UHFFFAOYSA-N 2-methoxy-1,2-diphenylpropan-1-one Chemical compound C=1C=CC=CC=1C(C)(OC)C(=O)C1=CC=CC=C1 IMAHLMWOKFATMM-UHFFFAOYSA-N 0.000 description 1
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 229910010199 LiAl Inorganic materials 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 229910052916 barium silicate Inorganic materials 0.000 description 1
- HMOQPOVBDRFNIU-UHFFFAOYSA-N barium(2+);dioxido(oxo)silane Chemical compound [Ba+2].[O-][Si]([O-])=O HMOQPOVBDRFNIU-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000005548 dental material Substances 0.000 description 1
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 235000021190 leftovers Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940086559 methyl benzoin Drugs 0.000 description 1
- KCRLWVVFAVLSAP-UHFFFAOYSA-N octyl dihydrogen phosphite Chemical compound CCCCCCCCOP(O)O KCRLWVVFAVLSAP-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000005368 silicate glass Substances 0.000 description 1
- QOQNJVLFFRMJTQ-UHFFFAOYSA-N trioctyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OCCCCCCCC QOQNJVLFFRMJTQ-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Inorganic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Dental Preparations (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB47951/76A GB1553580A (en) | 1975-11-21 | 1976-11-17 | Photopolymerisable acrylic or methacrylic acid ester-containing compositions |
| FR7634755A FR2332290A1 (fr) | 1975-11-21 | 1976-11-18 | Masses a base d'esters acryliques, polymerisables au moyen de rayons ultra-violets |
| SE7612895A SE424872B (sv) | 1975-11-21 | 1976-11-18 | Genom uv-ljus polymeriserbara massor pa basis av akrylsyraestrar innehallande bensoin och organiska fosfiter |
| AU19807/76A AU508267B2 (en) | 1975-11-21 | 1976-11-19 | Photopolymerizable acrylic composition |
| AT864676A AT355304B (de) | 1975-11-21 | 1976-11-19 | Durch uv-licht polymerisierbare massen auf basis von acrylsaeureestern |
| US05/743,323 US4116788A (en) | 1975-11-21 | 1976-11-19 | Process for the photopolymerization of acrylic acid ester-containing compositions |
| CA266,084A CA1075067A (en) | 1975-11-21 | 1976-11-19 | Photopolymerizable composition containing an ester, benzoin compound and an organic phosphite |
| NL7612904A NL7612904A (nl) | 1975-11-21 | 1976-11-19 | Door ultraviolet licht polymeriseerbare mengsels op basis van acrylzuuresters. |
| JP13963776A JPS5313692A (en) | 1975-11-21 | 1976-11-22 | Polymerizable material by ultraviolet |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1513875A CH606235A5 (enrdf_load_stackoverflow) | 1975-11-21 | 1975-11-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2646416A1 true DE2646416A1 (de) | 1977-05-26 |
Family
ID=4406681
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762646416 Withdrawn DE2646416A1 (de) | 1975-11-21 | 1976-10-14 | Durch uv-licht polymerisierbare massen auf basis von acrylsaeureester |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH606235A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2646416A1 (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0002831A3 (en) * | 1978-01-03 | 1979-07-25 | Espe Fabrik Pharmazeutischer Praparate Gmbh | Opaque photopolymerisable dental filling material |
| FR2912748A1 (fr) * | 2007-02-16 | 2008-08-22 | Centre Nat Rech Scient | Alkyl h-phosphonates de n,n'-dialkylimidazouliums, d'ammoniums quaternaires et leurs utilisations |
-
1975
- 1975-11-21 CH CH1513875A patent/CH606235A5/xx not_active IP Right Cessation
-
1976
- 1976-10-14 DE DE19762646416 patent/DE2646416A1/de not_active Withdrawn
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0002831A3 (en) * | 1978-01-03 | 1979-07-25 | Espe Fabrik Pharmazeutischer Praparate Gmbh | Opaque photopolymerisable dental filling material |
| US4372836A (en) | 1978-01-03 | 1983-02-08 | Espe Fabrik Parmazeutischer Praparate Gmbh | Light curable acrylic dental composition with calcium fluoride pigment |
| WO1983002557A1 (en) * | 1978-01-03 | 1983-08-04 | Werner Schmitt | Photopolymerizable opaque amalgam |
| FR2912748A1 (fr) * | 2007-02-16 | 2008-08-22 | Centre Nat Rech Scient | Alkyl h-phosphonates de n,n'-dialkylimidazouliums, d'ammoniums quaternaires et leurs utilisations |
| WO2008101881A3 (fr) * | 2007-02-16 | 2008-10-23 | Centre Nat Rech Scient | Alkyl h-phosphonates de n,n'-dialkylimidazoliums, d'ammoniums quaternaires et leurs utilisations |
| US8309736B2 (en) | 2007-02-16 | 2012-11-13 | Centre National De La Recherche Scientifique (Cnrs) | Alkyl H-phosphonates of N,N′-dialkylimidazoliums and of quaternary ammoniums and uses thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CH606235A5 (enrdf_load_stackoverflow) | 1978-10-31 |
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