CH575965A5 - Aromatic 1,2-diketone monoacetals - useful as photoinitiators and cross-linking agents - Google Patents

Aromatic 1,2-diketone monoacetals - useful as photoinitiators and cross-linking agents

Info

Publication number: CH575965A5
Authority: CH; Switzerland
Prior art keywords: alkyl; unsaturated; carbon atoms; compounds; monoacetals
Prior art date: 1972-07-28

Application number

CH1129572A

Other languages

German (de)

English (en)

Original Assignee

Ciba Geigy Ag

Priority date (The priority date 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 date listed.)

1972-07-28

Filing date

1972-07-28

Publication date

1976-05-31

1972-07-28 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1972-07-28 Priority to CH1129572A priority Critical patent/CH575965A5/de

1973-07-11 Priority to FI2211/73A priority patent/FI60194C/fi

1973-07-12 Priority to SE7309792A priority patent/SE417426B/sv

1973-07-17 Priority to CA176,687A priority patent/CA1054159A/fr

1973-07-19 Priority to AU58307/73A priority patent/AU483238B2/en

1973-07-24 Priority to NL7310297A priority patent/NL7310297A/xx

1973-07-25 Priority to DE2365497A priority patent/DE2365497C2/de

1973-07-25 Priority to DE2365852A priority patent/DE2365852C3/de

1973-07-25 Priority to DE2337813A priority patent/DE2337813C3/de

1973-07-26 Priority to DD172542A priority patent/DD105438A5/xx

1973-07-26 Priority to SU1953510A priority patent/SU508173A3/ru

1973-07-27 Priority to ZA735138A priority patent/ZA735138B/xx

1973-07-27 Priority to FR7327634A priority patent/FR2194698B1/fr

1973-07-27 Priority to DK416373A priority patent/DK152726C/da

1973-07-27 Priority to BE133928A priority patent/BE802867A/fr

1973-07-27 Priority to IT27241/73A priority patent/IT995086B/it

1973-07-27 Priority to AT649274A priority patent/AT324706B/de

1973-07-27 Priority to ES417307A priority patent/ES417307A1/es

1973-07-27 Priority to BR5741/73A priority patent/BR7305741D0/pt

1973-07-27 Priority to GB3584473A priority patent/GB1390006A/en

1973-07-28 Priority to JP48085362A priority patent/JPS5756456B2/ja

1974-06-20 Priority to SU742035589A priority patent/SU751329A3/ru

1975-08-22 Priority to AT652875A priority patent/AT341634B/de

1976-05-31 Publication of CH575965A5 publication Critical patent/CH575965A5/de

1976-06-01 Priority to SE7606164A priority patent/SE403119B/xx

1977-12-13 Priority to DK554777A priority patent/DK147052C/da

1978-06-22 Priority to US05/919,580 priority patent/US4190602A/en

1980-02-27 Priority to FI800580A priority patent/FI58927C/fi

1980-07-28 Priority to JP55103531A priority patent/JPS6026483B2/ja

Links

125000003118 aryl group Chemical group 0.000 title description 2
239000003431 cross linking reagent Substances 0.000 title 1
125000000217 alkyl group Chemical group 0.000 claims abstract description 13
229910052736 halogen Inorganic materials 0.000 claims abstract description 6
125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
150000002367 halogens Chemical class 0.000 claims abstract description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 23
150000001875 compounds Chemical class 0.000 claims description 19
229920000642 polymer Polymers 0.000 claims description 18
239000000178 monomer Substances 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 15
-1 vinyl compound Chemical class 0.000 claims description 15
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 6
238000007639 printing Methods 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
229920000098 polyolefin Polymers 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
239000000976 ink Substances 0.000 claims description 3
229920006305 unsaturated polyester Polymers 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 3
229920002554 vinyl polymer Polymers 0.000 claims 1
238000003860 storage Methods 0.000 abstract description 3
125000005843 halogen group Chemical group 0.000 abstract description 2
239000003795 chemical substances by application Substances 0.000 abstract 1
239000003999 initiator Substances 0.000 abstract 1
230000000977 initiatory effect Effects 0.000 abstract 1
239000003504 photosensitizing agent Substances 0.000 description 14
ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 11
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 description 9
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 8
238000004519 manufacturing process Methods 0.000 description 8
244000028419 Styrax benzoin Species 0.000 description 7
235000000126 Styrax benzoin Nutrition 0.000 description 7
235000008411 Sumatra benzointree Nutrition 0.000 description 7
150000001991 dicarboxylic acids Chemical class 0.000 description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
235000019382 gum benzoic Nutrition 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
229960002130 benzoin Drugs 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
238000000034 method Methods 0.000 description 5
238000000465 moulding Methods 0.000 description 5
238000006116 polymerization reaction Methods 0.000 description 5
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 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
238000000576 coating method Methods 0.000 description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000011248 coating agent Substances 0.000 description 3
239000008199 coating composition Substances 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
150000002148 esters Chemical group 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
229920000728 polyester Polymers 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
229920006337 unsaturated polyester resin Polymers 0.000 description 3
RURQFXYDNRAWNW-UHFFFAOYSA-N 1,2-diphenyl-2,2-bis(2-phenylethoxy)ethanone Chemical compound C=1C=CC=CC=1CCOC(C=1C=CC=CC=1)(OCCC=1C=CC=CC=1)C(=O)C1=CC=CC=C1 RURQFXYDNRAWNW-UHFFFAOYSA-N 0.000 description 2
JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
150000001408 amides Chemical group 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Chemical group 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
229940052303 ethers for general anesthesia Drugs 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000004922 lacquer Substances 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
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
238000006068 polycondensation reaction Methods 0.000 description 2
229920001225 polyester resin Polymers 0.000 description 2
239000004645 polyester resin Substances 0.000 description 2
229920005862 polyol Polymers 0.000 description 2
150000003077 polyols Chemical class 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000047 product Substances 0.000 description 2
YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
230000005855 radiation Effects 0.000 description 2
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
239000000758 substrate Substances 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
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VIFFKTKUPYOXJM-UHFFFAOYSA-N 1,2-diphenyl-2,2-dipropoxyethanone Chemical compound C=1C=CC=CC=1C(OCCC)(OCCC)C(=O)C1=CC=CC=C1 VIFFKTKUPYOXJM-UHFFFAOYSA-N 0.000 description 1
KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 1
TYMYJUHDFROXOO-UHFFFAOYSA-N 1,3-bis(prop-2-enoxy)-2,2-bis(prop-2-enoxymethyl)propane Chemical compound C=CCOCC(COCC=C)(COCC=C)COCC=C TYMYJUHDFROXOO-UHFFFAOYSA-N 0.000 description 1
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MWZJGRDWJVHRDV-UHFFFAOYSA-N 1,4-bis(ethenoxy)butane Chemical compound C=COCCCCOC=C MWZJGRDWJVHRDV-UHFFFAOYSA-N 0.000 description 1
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GIMQKKFOOYOQGB-UHFFFAOYSA-N 2,2-diethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)(OCC)C(=O)C1=CC=CC=C1 GIMQKKFOOYOQGB-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
OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
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239000012230 colorless oil Substances 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000002704 decyl 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])* 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
BDUPRNVPXOHWIL-UHFFFAOYSA-N dimethyl sulfite Chemical compound COS(=O)OC BDUPRNVPXOHWIL-UHFFFAOYSA-N 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
238000001035 drying Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
BLCTWBJQROOONQ-UHFFFAOYSA-N ethenyl prop-2-enoate Chemical compound C=COC(=O)C=C BLCTWBJQROOONQ-UHFFFAOYSA-N 0.000 description 1
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125000001033 ether group Chemical group 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
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239000003365 glass fiber Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
230000001678 irradiating effect Effects 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
125000001421 myristyl group Chemical group [H]C([*])([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])C([H])([H])[H] 0.000 description 1
ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
150000002832 nitroso derivatives Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical class C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920001748 polybutylene Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
229910052939 potassium sulfate Inorganic materials 0.000 description 1
235000011151 potassium sulphates Nutrition 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000012719 thermal polymerization Methods 0.000 description 1
239000013008 thixotropic agent Substances 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000001993 wax Substances 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/01—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to unsaturated polyesters

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Polymerisation Methods In General (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH1129572A 1972-07-28 1972-07-28 Aromatic 1,2-diketone monoacetals - useful as photoinitiators and cross-linking agents CH575965A5 (en)

Priority Applications (28)

Application Number	Priority Date	Filing Date	Title
CH1129572A CH575965A5 (en)	1972-07-28	1972-07-28	Aromatic 1,2-diketone monoacetals - useful as photoinitiators and cross-linking agents
FI2211/73A FI60194C (fi)	1972-07-28	1973-07-11	Foerfarande foer framstaellning av bensil-monoketaler
SE7309792A SE417426B (sv)	1972-07-28	1973-07-12	Forfarande for framstellning av monoacetaler av bensil
CA176,687A CA1054159A (fr)	1972-07-28	1973-07-17	Derives monoacetals de 1,2-dicetones aromatiques
AU58307/73A AU483238B2 (en)	1972-07-28	1973-07-19	Monoacetals of aromatic 1, 2-diketones
NL7310297A NL7310297A (fr)	1972-07-28	1973-07-24
DE2365497A DE2365497C2 (de)	1972-07-28	1973-07-25	Benzil-monoacetale und ihre Verwendung
DE2365852A DE2365852C3 (de)	1972-07-28	1973-07-25	Verfahren zur Herstellung von Monoacetalen aromatischen 1,2-Diketone
DE2337813A DE2337813C3 (de)	1972-07-28	1973-07-25	Verfahren zur Herstellung von Monoacetalen aromatischer 1,2-Diketone
DD172542A DD105438A5 (fr)	1972-07-28	1973-07-26
SU1953510A SU508173A3 (ru)	1972-07-28	1973-07-26	Способ получени моноацеталей ароматических 1,2-дикетонов
DK416373A DK152726C (da)	1972-07-28	1973-07-27	Fremgangsmaade til fremstilling af monoacetaler af aromatiske 1,2-diketoner
FR7327634A FR2194698B1 (fr)	1972-07-28	1973-07-27
ZA735138A ZA735138B (en)	1972-07-28	1973-07-27	Monoacetals of aromatic 1,2-diketones
BE133928A BE802867A (fr)	1972-07-28	1973-07-27	Monoacetals de 1,2-dicetones aromatiques, preparation de ces composes et leur utilisation, notamment comme photo-sensibilateurs
IT27241/73A IT995086B (it)	1972-07-28	1973-07-27	Monoacetali di 1 2 dichetoni aromatici
AT649274A AT324706B (de)	1972-07-28	1973-07-27	Sensibilisatoren zur photopolymerisation polymerisierbarer systeme die ungesättigte verbindungen enthalten oder zur photochemischen vernetzung linearer polymerisate
ES417307A ES417307A1 (es)	1972-07-28	1973-07-27	Procedimiento para la preparacion de monoacetales de 1,2- dicetonas aromaticas.
BR5741/73A BR7305741D0 (pt)	1972-07-28	1973-07-27	Processo para obtencao de monoacelais de 1, 2-dicetonas aromaticas
GB3584473A GB1390006A (en)	1972-07-28	1973-07-27	Monoacetals of aromatic 1,2-diketones
JP48085362A JPS5756456B2 (fr)	1972-07-28	1973-07-28
SU742035589A SU751329A3 (ru)	1972-07-28	1974-06-20	Способ получени (со) полимеров
AT652875A AT341634B (de)	1972-07-28	1975-08-22	Photopolymerisierbare gemische
SE7606164A SE403119B (sv)	1972-07-28	1976-06-01	Anvendning av bensil-monoacetaler sasom sensibilisatorer for fotopolymerisation av omettade foreningar
DK554777A DK147052C (da)	1972-07-28	1977-12-13	Anvendelse af benzil-monoacetaler som sensibilisatorer til fotopolymerisation af polymerisationsdygtige systemer, der indeholder umaettede forbindelser
US05/919,580 US4190602A (en)	1972-07-28	1978-06-22	Monoacetals or aromatic 1,2-diketones
FI800580A FI58927C (fi)	1972-07-28	1980-02-27	Anvaendning av monoacetaler av aromatiska 1,2-diketoner saosom fotosensibilisatorer
JP55103531A JPS6026483B2 (ja)	1972-07-28	1980-07-28	不飽和化合物を含む重合系の光重合反応用増感剤

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1129572A CH575965A5 (en)	1972-07-28	1972-07-28	Aromatic 1,2-diketone monoacetals - useful as photoinitiators and cross-linking agents

Publications (1)

Publication Number	Publication Date
CH575965A5 true CH575965A5 (en)	1976-05-31

Family

ID=4372073

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1129572A CH575965A5 (en)	1972-07-28	1972-07-28	Aromatic 1,2-diketone monoacetals - useful as photoinitiators and cross-linking agents

Country Status (7)

Country	Link
JP (1)	JPS6026483B2 (fr)
AT (1)	AT324706B (fr)
BE (1)	BE802867A (fr)
BR (1)	BR7305741D0 (fr)
CH (1)	CH575965A5 (fr)
SE (1)	SE403119B (fr)
ZA (1)	ZA735138B (fr)

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1972
- 1972-07-28 CH CH1129572A patent/CH575965A5/de not_active IP Right Cessation
1973
- 1973-07-27 AT AT649274A patent/AT324706B/de not_active IP Right Cessation
- 1973-07-27 BR BR5741/73A patent/BR7305741D0/pt unknown
- 1973-07-27 BE BE133928A patent/BE802867A/fr not_active IP Right Cessation
- 1973-07-27 ZA ZA735138A patent/ZA735138B/xx unknown
1976
- 1976-06-01 SE SE7606164A patent/SE403119B/xx not_active IP Right Cessation
1980
- 1980-07-28 JP JP55103531A patent/JPS6026483B2/ja not_active Expired

Also Published As

Publication number	Publication date
SE403119B (sv)	1978-07-31
AT324706B (de)	1975-09-10
SE7606164L (sv)	1976-06-02
JPS6026483B2 (ja)	1985-06-24
BE802867A (fr)	1974-01-28
BR7305741D0 (pt)	1974-07-18
JPS5695904A (en)	1981-08-03
ZA735138B (en)	1974-07-31

Legal Events

Date	Code	Title	Description
1992-03-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
CH575965A5 (en)	1976-05-31	Aromatic 1,2-diketone monoacetals - useful as photoinitiators and cross-linking agents
DE2365497C2 (de)	1985-03-21	Benzil-monoacetale und ihre Verwendung
DE1769854C3 (de)	1982-08-19	Photoinitiatoren und Verfahren zur Photopolymerisation
EP0007508B1 (fr)	1983-06-01	Acylphosphinoxydes, leur préparation et leur utilisation
DE3114341A1 (de)	1982-11-11	Acylphosphinverbindungen, ihre herstellung und verwendung
EP0108037B1 (fr)	1989-06-07	Dérivés de propiophénone comme photo-initiateurs dans la photo-polymérisation
DE2639742C2 (de)	1986-12-11	Verwendung bestimmter Glyoxalate als Initatoren der Photopolymerisation
EP0106176B1 (fr)	1986-08-20	Compositions photopolymérisables et leur utilisation
US4743657A (en)	1988-05-10	Method for preparing polymer bound stabilizers made from non-homopolymerizable stabilizers
EP0057474A2 (fr)	1982-08-11	Composés d'oxydes d'acylphosphines, leur préparation et utilisation
DE2612132A1 (de)	1976-09-30	Durch strahlung und waerme haertbare formmassen auf der grundlage von melaminverbindungen
US3657088A (en)	1972-04-18	Moulding and coating masses hardenable by uv irradiation
DE60223689T2 (de)	2008-10-30	Multifunktionale alkoxyamine auf grundlage von polyalkylpiperidinen, polyalkylpiperazinonen und polyalkylmorpholinonen, und deren verwendung als polymerisationsregulatoren/-initiatoren
EP0037463B1 (fr)	1985-06-05	Résines de polyester photopolymérisables, procédé pour leur préparation et leur utilisation comme liants de peinture
DE1807301A1 (de)	1970-06-04	Neue Buttersaeurederivate
US3728377A (en)	1973-04-17	4,4-bis(alkoxycarbonyl)benzoin ethers
DE4014489A1 (de)	1991-11-14	Copolymerisierbare benzilketal-fotoinitiatoren
DE2625538C2 (de)	1984-03-22	Photopolymerisierbare Überzugsmassen
DE1945725A1 (de)	1971-03-11	Lagerfaehige,photosensibilisierte Polyesterform- und -ueberzugsmassen
US4082821A (en)	1978-04-04	1-oxo-2-(phosphona)-1,2-diphenylethanes
US4459192A (en)	1984-07-10	Photopolymerizable composition stabilized with epoxide compounds and process
DE1923266A1 (de)	1970-11-19	Alpha-Methylolbenzoinaether
CA1054159A (fr)	1979-05-08	Derives monoacetals de 1,2-dicetones aromatiques
DE1769853C3 (de)	1978-01-19	Durch UV-Bestrahlen polymerisierbare Massen
US4338172A (en)	1982-07-06	Photopolymerizable composition stabilized with epoxide compounds and process