Acylphosphine oxides

Details Acylphosphine oxides Acylphosphine oxides

1997-03-05

1998-02-24

Ivy, C. Warren

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Compositions to be polymerized by wave energy wherein said...

568 14, 568 17, 546 22, 548530, 549 6, 549218, 522 63, C08G 1810, C07F 953

Patent

active

057212929

DESCRIPTION:

BRIEF SUMMARY
This is the National Stage Application of PCT/EP95/03392 filed Aug. 29, 1995 now WO96/07662 published Mar. 14, 1996.
The invention relates to novel trisacylphosphine oxides, to their use as photoinitiators and to photopolymerizable compositions comprising the compounds according to the invention.
Acylphosphine oxides are known as photoinitiators. U.S. Pat. No. 4,298,738 discloses monoacylphosphine oxides, while U.S. Pat. Nos. 4,737,593 and 4,792,632 disclose bisacylphosphine oxides, in all cases as photoinitiators. In Inorg. Chim. Acta 76(5-6), L273,274 (1983), C. M. Demanet describes trisdimethylamidophosphine oxide as a ligand in uranyl complexes for analysis by photoelectron spectroscopy. At. Energ. 28(5), 383-8 (1970) (=Chem. Abstr. Vol. 73, 92156p (1970)) discloses further tris-substituted phosphine oxides as extractants for uranium. Chem. Abstr. O).sub.3 --PO--!.sub.2 CO. From U.S. Pat. No. 3,668,093, trisbenzoylphosphine is known as a photoinitiator. In Phosphorus, Sulfur, and Silicon, 1993, Vol. 85, 193-205, J. R. Goerlich et al. describe the synthesis of tris(1-adamantoyl)phosphine oxide.
For the extensive range of application of photoinitiators, there continues to be a need for effective photoinitiators.
It has been found that trisacylphosphine oxide compounds are effective photoinitiators. The invention therefore specifically relates to compounds of the formula I ##STR2## X is oxygen or sulfur, R.sub.1, R.sub.2 and R.sub.3 independently of one another are a group ##STR3## C.sub.2 -C.sub.8 alkenyl, phenyl which is unsubstituted or is substituted from one to four times with C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -C.sub.6 alkylthio and/or halogen, or are naphthyl which is unsubstituted or is substituted from one to four times with C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -C.sub.6 alkylthio and/or halogen, or are biphenyl which is unsubstituted or is substituted from one to four times with C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -C.sub.6 alkylthio and/or halogen, or R.sub.1, R.sub.2 and R.sub.3 independently of one another are an O-, S- or N-containing 5- or 6-membered heterocyclic ring, ##STR4## or R.sub.1 and R.sub.2 are linked to form a ring containing 4 to 10 carbon atoms which is unsubstituted or substituted by 1 to 6 C.sub.1 -C.sub.4 alkyl groups, C.sub.1 -C.sub.18 alkyl, or R.sub.5 and R.sub.6, together with the carbon atom to which they are attached, form a cyclopropyl, cyclopentyl or cyclohexyl ring, and hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen.
C.sub.1 -C.sub.12 alkyl may be linear or branched and is for example methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, 2,4,4-trimethylpent-1-yl, 2-ethylhexyl, nonyl, decyl or dodecyl. In addition, C.sub.1 -C.sub.18 alkyl is for example tetradecyl, heptadecyl or octadecyl.
C.sub.1 -C.sub.12 Alkoxy is for example methoxy, ethoxy, n-propoxy, isopropoxy, butyloxy, octyloxy, decyloxy or dodecyloxy, especially C.sub.1 -C.sub.4 alkoxy and preferably methoxy.
C.sub.1 -C.sub.6 Alkylthio is for example methylthio, ethylthio, n-propylthio, isopropylthio, butylthio or hexylthio.
C.sub.2 -C.sub.8 Alkenyl is for example vinyl, allyl, methallyl, 1,1-dimethallyl, 2-butenyl, 2-hexenyl or octenyl.
Halogen is fluorine, chlorine, bromine or iodine, especially chlorine.
Phenyl substituted from one to four times with halogen, C.sub.1 -C.sub.12 alkyl and/or C.sub.1 -C.sub.12 alkoxy is for example chlorophenyl, dichlorophenyl, tetrachlorophenyl, tolyl, dimethylphenyl, mesityl, tetramethylphenyl, ethylphenyl, diethylphenyl, triethylphenyl, methylethylphenyl, dimethylethylphenyl, methoxyphenyl, dimethoxyphenyl, trimethoxyphenyl, dimethoxymethylphenyl, methoxymethylphenyl, dimethylmethoxyphenyl, ethoxyphenyl, diethoxyphenyl, diethoxymethylphenyl, propyloxyphenyl, butoxyphenyl, dibutoxyphenyl, butoxymethoxyphenyl, ethoxymethoxyphenyl, butoxyethoxyphenyl, preferably tolyl.
Phenyl, naphthyl or biphenyl radicals are unsubstituted or are su

REFERENCES:
patent: 4292152 (1981-09-01), Lechtken
patent: 4324744 (1982-04-01), Lechtken
patent: 4719297 (1988-01-01), Henne
patent: 4985472 (1991-01-01), Aosai
patent: 5218009 (1993-06-01), Rutsch
patent: 5399770 (1995-03-01), Leppard
patent: 5410060 (1995-04-01), Schroeder
patent: 5414133 (1995-05-01), Hall
patent: 5472992 (1995-12-01), Leppard
patent: 5532112 (1996-07-01), Kohler

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