Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Compositions to be polymerized by wave energy wherein said...
Patent
1995-10-06
1998-01-27
Lesmes, George F.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Compositions to be polymerized by wave energy wherein said...
522 8, 522 10, 522 48, 522 68, 502106, C08F26510
Patent
active
057123225
DESCRIPTION:
BRIEF SUMMARY
This application claims benefit of international application PCT/GB94/00730, filed Apr. 16, 1994.
This invention relates to compositions of matter, to photoinitiator compositions and photopolymerisable compositions derived therefrom and to their use in the production of polymeric materials.
It is known to polymerise olefinically unsaturated compounds by exposing such compounds to electromagnetic radiation such as visible or ultraviolet light in the presence of a photoinitiator which is capable of absorbing the radiation and thereby generating free radicals.
One known class of photoinitiators comprises ketones which are generally used in conjunction with a hydrogen donor such as an amine from which the photoinitiator, when subjected to and excited by radiation of appropriate wavelength, abstracts a hydrogen atom and so forms radicals. Certain ketone photoinitiators are described in United Kingdom Patent No 1408265, particular emphasis being placed on .alpha.-diketones one of which, camphorquinone, has achieved considerable commercial success as a component of visible light curable compositions in spite of its high cost and sensitivity to oxygen inhibition.
It has now been found that the disadvantages associated with camphorquinone can be minimised by using it in conjunction with certain anthraquinone compounds as hereinafter defined. In particular, it has been found that when the hereinafter defined combinations of camphorquinone and an anthraquinone compound are used, a satisfactory cure rate can be maintained at lower levels of camphorquinone, thus reducing costs, and also that the sensitivity to inhibition by oxygen is reduced.
Accordingly, in one aspect, the invention provides a composition of matter comprising 100 parts by weight of camphorquinone and from 1 to 50 parts by weight of an anthraquinone compound having in the 2-position a substituent of the formula: and X represents ##STR2## wherein R.sup.2 represents hydrogen or an optionally substituted hydrocarbyl radical.
Optionally substituted hydrocarbyl radicals which may be represented by R.sup.1 and R.sup.2 in the anthraquinone compound include optionally substituted alkyl, optionally substituted aryl and optionally substituted alkenyl.
Substituents which may optionally be present on the hydrocarbyl radicals include halogen atoms such as chlorine. As examples of optionally substituted alkyl radicals which may be represented by R.sup.1 and R.sup.2, there may be mentioned optionally substituted C.sub.1-4 -alkyl, for example methyl, chloroethyl and isobutyl, and also optionally substituted higher alkyl radicals which may be linear or branched and which may contain up to 10 carbon atoms, for example hexyl and 2-ethylpentyl, or even larger numbers of carbon atoms, for example up to 20. As examples of optionally substituted aryl radicals which may be represented by R.sup.1 and R.sup.2, there may be mentioned optionally substituted phenyl and, as examples of optionally substituted alkenyl radicals, there may be mentioned optionally substituted vinyl and also optionally substituted higher alkenyl radicals containing up to 20 carbon atoms, for example heptadecenyl. The presence, as R.sup.1 or R.sup.2, of alkyl or alkenyl radicals having more than 4 carbon atoms can provide the anthraquinone compound with increased solubility in the polymerisable olefinically unsaturated compound and therefore permit higher concentrations of photoinitiator to be present in compositions of the invention. The positions of the anthraquinone nucleus other than the 2-position may be unsubstituted or substituted.
As an example of a preferred anthraquinone compound there may be mentioned 2-acryloylaminoanthraquinone.
If desired, the compositions of the invention may contain a mixture of two or more of the 2-substituted anthraquinones.
Preferred compositions of the invention contain from 2 to 25 parts by weight of the anthraquinone compound for each 100 parts by weight of camphorquinone and particularly include compositions in which the anthraquinone compound and the camphorquinone
REFERENCES:
patent: 2989455 (1961-06-01), Neugebauer
patent: 4828583 (1989-05-01), Oxman et al.
patent: 5283160 (1994-02-01), Allen et al.
patent: 5321053 (1994-06-01), Hino et al.
patent: 5545676 (1996-08-01), Palazzotto et al.
Ghosh Pushpito Kumar
Weddell Iain Andrew
Yates John Edward
Lesmes George F.
Malia Victoria M.
VerSteeg Steven H.
Zeneca Limited
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