Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Compositions to be polymerized by wave energy wherein said...
Patent
1998-10-26
2000-07-18
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 2, 522 15, 522 25, 522 26, 522 28, 522 29, 522 48, 522 63, 522 74, 522 75, 522 78, 522 81, 522170, 522182, 522187, 522908, 522909, 427510, 427511, 430269, 4302701, 546152, 546153, 546178, 546180, 546183, 544349, C08F 250, C08F 400, C07D21500, C07D24136, C08J 704
Patent
active
060908653
DESCRIPTION:
BRIEF SUMMARY
This invention relates to a photoinitiator system, a polymerisable composition, comprising the photoinitiator system and to new dyes usable as photoinitiators and precursors of such dyes.
For free radical polymerisation of an olefinically unsaturated compound one method is to irradiate a composition containing it and a photoinitiator with electromagnetic radiation such as visible or ultraviolet light, the photoinitiator generating free radicals when so irradiated. It has now been found that in photoinitiated compositions containing certain styryl-substituted heterocycles provide rapid photopolymerisation and are also bleachable by electro-magnetic radiation, so that they can cause little or no discoloration of the resulting polymer and can provide a means of forming polymer in relatively thick layers.
The present invention pertains to a photoinitiator system comprising (a) at least one O-alkylated aromatic nitrogen-heterocycle amine oxide cation salt and optionally (b) at least one electron donor compound.
Preferably the O-alkylated aromatic nitrogen-heterocycle amine oxide cation, carries a styryl substituent in at least one of its 2-, 4- and 6-positions. Such an oxide is cationic and is of course accompanied by an anion, which can be any convenient one, provided it does not interfere with the polymerisation process or introduce unwanted components; it may enhance the photoinitiator activity, as shown below. The parent heterocycle of the oxide should be one incapable of absorbing light absorbed by the photoinitiator and preferably colourless. disclosed in EP-A 441 232 and especially in EP-A 498 194. Further compounds of that kind are disclosed by W. Schnabel in Macromolecular Engineering, edited by M. K. Mishra et al, Plenum Press, New York (1995), pages 67-83 and in Adv. Polym. Sci. 1997, 127, 59-86.
The parent heterocycle of the oxide cation preferably contains a pyridine or 1,4-diazine ring, especially a condensed ring system such as quinoline or 5,6-benz-1,4-diazine. The term "aromatic" as used herein includes any such heterocycles having conjugated double bonds in the ring.
The oxide cation preferably has the structure of the formula I as described below. Especially preferred are photoinitiator systems comprising as O-alkylated aromatic nitrogen-heterocycle amine oxide cation a compound of the formula I ##STR2## wherein X is CH, C--CH.sub.3, C--Cl, C--O--C.sub.1 -C.sub.8 alkyl or N; ##STR3## R.sub.1 is C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.12 alkyl, halogen, NO.sub.2, benzyloxy or phenyloxy, wherein the phenylring in the benzyloxy or phenyloxy group is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.6 alkoxy, halogen or CF.sub.3 ; phenyloxy, wherein the phenylring in the benzyloxy or phenyloxy group is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.6 alkoxy, halogen or CF.sub.3 ; alkyl, or Y is C.sub.1 -C.sub.6 alkoxy, halogen, CF.sub.3, NO.sub.2, CF.sub.3 O, benzyloxy or phenyloxy, wherein the phenylring in the benzyloxy or phenyloxy group is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.6 alkoxy, halogen or CF.sub.3 or, if n is two and both Y are alkoxy these alkoxy groups may form a dioxane or dioxane fused to the phenyl of the styryl residue;
Both n of (R.sub.1).sub.n and (Y).sub.n are meant to be independently of one another 1 to 4. (R.sub.1).sub.n in the context of this application may be n different R.sub.1, independently of one another having one of the meanings given above. The same applies for (Y).sub.n.
If n in the formula I is two and both Y are C.sub.1 -C.sub.6 alkoxy and these alkoxy groups form a dixolane or dioxane fused to the phenyl of the styryl residue a structure of the following formula Ia is meant ##STR4## wherein n1 is an integer 1 or 2 and R, R.sub.1, R.sub.2, X and n are as defined above.
The oxide cation preferably has the structure Ib; ##STR5## where X is CH or N; 4-position but possibly the residue of one or more condensed rings; bathochromic: 4-C.sub.1-6 alkyl, for example isopropyl (440); 4-C.s
REFERENCES:
patent: 5912257 (1999-06-01), Prasad et al.
Yagci et al., Macromol. Symp., vol. 85, pp. 115-127, (1994).
Iwakura et al., Radioisotope Sample Meas. Tech. Med. Biol., Proc. Symp., Vienna 1965, "Carbon-14 and Hydrogen-3 Measurement by Means of a Liquid Scintillation Spectrometer: Colour Quenching", pp.447-455.
Shatzmiller et al., Liebigs Annalen Der Chemie, No. 6, 1983, pp. 897-905 (Abstract).
Cunningham Allan Francis
Dudman Christopher Curtis
Kunz Martin
Berman Susan W.
Ciba Specialty Chemicals Corporation
Hall Luther A. R.
Stevenson Tyler A.
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