Betaketosulphones derivatives suitable to the use as polymerizat

Details Betaketosulphones derivatives suitable to the use as polymerizat Betaketosulphones derivatives suitable to the use as polymerizat

1998-03-03

2000-12-19

Berman, Susan W.

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

Synthetic resins

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

522 16, 522 17, 522 26, 522 27, 522 53, 522 55, 522 59, 522 75, 522 81, 522 83, 522 92, 522 96, 522182, C08F 250, C08F 400, C08K 322, C09D 1110

Patent

active

061628417

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

The present invention concerns new betaketosulphones suitable to the use as polymerization photoinitiators, the process for their preparation and the photopolymerizable systems containing the same.
Said systems find application in the inks field and particularly in the field of the inks having high content in pigments.


PRIOR ART

The photochemical polymerization of monomers and unsaturated prepolymers is a widespread technique used in various technological fields, such as those of paints and lacquers, of printing inks, in the making of printing plates and electronic circuits, stencils for ceramics and textile printing, and in the manufacture of dental apparatuses.
In particular, in the production of printing inks, the photocross-linkable systems used are based on active monomers, such as derivatives of the acrylic and methacrylic acid, N-vinylpyrrolidone, vinyl ethers, styrene, allyl derivatives, maleic and fumaric acid derivatives; on ethylenic unsaturated polyester, polyether, polyurethane, silicone, epoxy oligomers and polymers; on pigments, fillers, additives, various auxiliares, on a photoinitiator or on a system composed of a mixture of photoinitiators, some of them particularly suitable to the pigmented system and other acting as adjuvants (benzophenone, benzyldimethylketale etc.). The constituent parts of these systems of photoinitiators are generally:
a) a photoinitiator at least, which must show an absorption spectrum in the spectral region where resins and pigments have a minimum in absorpion or reflection of the incident light (optical window) and where the light source used for the process emits a peak or a radiation band (light).
For the photoinitiator systems at present in use, this region is located between 360 and 420 nm.
b) a coinitiator at least, generally a tertiary amine with hydrogen atoms available on carbon in alpha position with respect to nitrogen, which is essential when the photoinitiator acts by a hydrogen extraction mechanism, such as benzophenone and thioxanthones.
Said coinitiator in any case turns out to be very useful even in the case of photoinitiators acting by homolytic breaking: in fact the tertiary amines eliminate the oxygen inhibitory effect, increasing the speed of the whole photopolymerization process.
The polymerization inhibition owing to oxygen is a problem particularly important for printing inks, considering their limited thickness and their high surface/volume ratio.
For such purposes aromatic aliphatic or entirely aliphatic amines are generally used, such as for instance triethylamine, N-methyldiethanolamine, N,N-dimethylethanolamine, p-dimethylaminoethylbenzoate, as is for instance described in the U.S. Pat. No. 4,318,791.
The photopolymerization of pigmented printing inks has always shown various technical problems connected to the existence of some necessities: with the industrial application in printing and graphic arts; tone of the pigments added to the system, such as an undesired yellowing of the obtained film; needed, about 20-60% by weight; photolysis products or to not reacted monomers, particularly to acrylates, and limiting the presence of volatile substances during the photopolymerization stages.
Among the photoinitiators which have found grater use in the ink field there is the isopropyl thioxanthone (ITX), having the following formula ##STR1## and similar derivatives (for instance the diethyl thioxanthone), as described in the American U.S. Pat. No. 4,434,035.
However the compound has the drawback to be coloured and consequently to give an undesired colouring to the white or light tone inks. Some attempts to correct such defects have been carried out, as described in the European Patent EP 88050, with the introduction of the photoinitiators belonging to the class of the aminoketones, among which the 2-methyl-1-[4-(methylthio)phenyl]-2-morpholino-1-propanone (MMMP) has been developed.
In this case the yellowing of the film turns out to be very low, but a serious limitation is presented by the residual odour due to the

REFERENCES:
patent: 3903322 (1975-09-01), Ravve et al.
patent: 4318791 (1982-03-01), Felder et al.
patent: 4374984 (1983-02-01), Eichler et al.
patent: 4434035 (1984-02-01), Eichler et al.
patent: 4582862 (1986-04-01), Berner et al.
patent: 5026740 (1991-06-01), Li Bassi et al.
AN 83-760394 WPINDEX Abstract of EP 88050A Sep. 25, 1993.

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