Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Compositions to be polymerized by wave energy wherein said...
Patent
1993-04-16
1995-04-18
Chapman, Mark A.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Compositions to be polymerized by wave energy wherein said...
522 64, 562 24, C08F 246
Patent
active
054079691
DESCRIPTION:
BRIEF SUMMARY
A number of photoinitiators based on acylphosphinic acid esters and acylphosphane oxides are already known (cf. EP Published Specification 7508). EP Published Specification 304 782 furthermore describes acyl-(6H)-dibenz[c,e][1,2]-oxaphosphorine 6-oxides for this purpose. However, these compounds are not suitable as photoinitiators in aqueous, photopolymerized compositions. Acylphosphonic acid salts are indeed already described in EP Published Specification 62 839 for use as photoinitiators in aqueous systems; a disadvantage here, however, is the expensive preparation of these salts, during which, for example, alkyl oxides occur as by-products.
The object of the invention was now to provide novel acyl-phosphorus compounds which do not have the disadvantages of the prior art and which be prepared, in particular, in a manner which is particularly simple industrially, but nevertheless meet the high requirements demanded in practice and also are particularly suitable for use in aqueous photopolymerizable compositions. The invention relates to a process for the preparation of acyl-(2'-hydroxybiphenyl-2-yl)-phosphinic acid salts of the formula (I) ##STR2## in which each of the radicals R.sup.1, R.sup.2 and R.sup.3 can be present once or several times, preferably not more than three times, and in which alkoxy radical having in each case 1 to 6, preferably 1 to 4, carbon atoms or halogen having an atomic number of 9 to 35, preferably chlorine, number of 3 to 19, or N(R.sup.4).sub.4.sup.+, in which the radicals R.sup.4 are identical or different and are an alkyl radical having in each case 1 to 6, preferably 1 to 4, carbon atoms.
These compounds (I), which have a very good reactivity as photoinitiators, are surprisingly readily water-soluble, although their molecule mainly comprises hydrophobic regions (hydrocarbon radicals). Furthermore, the very reactive ##STR3## grouping in them is surprisingly stable to hydrolysis.
Compounds (I) which are preferably prepared according to the invention are those which have at least one of the following features: both these radicals, is/are hydrogen, preferably one to three alkyl radicals, in particular methyl radicals, and
Alkyl or alkoxy in the radicals R.sup.1 to R.sup.3 is, in particular, methyl or ethyl.
Examples of alkyl groups are methyl, ethyl, propyl, isopropyl and the various butyl radicals, the two former, and especially methyl, being preferred. Preferred examples of alkoxy radicals are methoxy and ethoxy, in particular methoxy.
In addition to the compounds (I) described in the examples, the following may also be mentioned here as examples: the sodium salt of (4-methyl-benzoyl)(2'-hydroxybiphenyl-2-yl)-phosphinic acid, the sodium salt of (2,6-dimethyl-benzoyl)(2'-hydroxybiphenyl-2-yl)-phosphinic acid, the lithium salt of (4-ethyl-benzoyl)(2'hydroxybiphenyl-2-yl)-phosphinic acid, the lithium salt of (2,6-dichlorobenzoyl)(2'-hydroxybiphenyl-2-yl)-phosphinic acid and the potassium salt of (2,6-dichlorobenzoyl)(2'-hydroxybiphenyl-2-yl)-phosphinic acid.
The invention also relates to a process for the preparation of the compounds (I), which comprises reacting 6-acyl-(6H)-dibenz[c,e][1,2]oxaphosphorine 6-oxides of the formula (II) ##STR4## in which R.sup.1 to R.sup.3 and Ar have the meaning given in the above formula (I), with salts of carbonic acid of the formulae MeHCO.sub.3 (III) or Me.sub.2 CO.sub.3 (IV), in which Me in each case has the meaning according to formula (I), the reaction being carried out in the presence of water in the case of the carbonates (IV) (in this context, see also the attached sheet of formulae).
Surprisingly, the compounds (I) are obtained in good yields by this process.
The reaction is expediently carried out in the presence of a diluent, such as, for example, water, which must in any case be present in the case of the carbonates (IV). Other possible diluents are the usual, preferably water-miscible, polar organic solvents, such as ethers and glycol ethers, for example diethyl ether, 1,2-dimethoxyethane, ethylene glycol dibutyl ether, tetrahydrofur
REFERENCES:
patent: 3702878 (1972-11-01), Saito
patent: 4719297 (1988-01-01), Henne et al.
patent: 5008426 (1991-04-01), Kleiner et al.
patent: 5096935 (1992-03-01), Kleiner et al.
Bastian Udo
Gersdorf Joachim
Kleiner Hans-Jerg
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