Radiation imagery chemistry: process – composition – or product th – Imaging affecting physical property of radiation sensitive... – Radiation sensitive composition or product or process of making
Patent
1996-05-21
1997-10-28
Hamilton, Cynthia
Radiation imagery chemistry: process, composition, or product th
Imaging affecting physical property of radiation sensitive...
Radiation sensitive composition or product or process of making
522 14, 522 16, 548427, G03F 729, G03F 728
Patent
active
056816855
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a photopolymerizable composition containing a squarylium compound. Since the photopolymerizable composition has the high sensitivity to from visible lights having the wavelength of not less than 600 nm near infrared lights, it is useful as a red light sensitive component in visible laser recording materials such as PS plate for laser direct plate making, dry film resist, digital proof, holograph and the like, and panchromatic photosensitive materials such as color hologram photosensitive material, full color designation photosensitive material containing a photopolymerizable composition in a microcapsule, as well as light sensitive materials such as coating agent, adhesive and the like for which visible to near infrared lights sources are used.
BACKGROUND ART
There is disclosed a photopolymerizable composition using a squarylium compound as a sensitizing dye and using a s-triazine compound as a radical generator in JP-A 2-48665, JP-A 2-229802, JP-A 2-306247, JP-A 4-106548, JP-A 5-5005 and the like.
There are known a photopolymerizable composition using a squarylium compound as a sensitizing dye and an azinium salt as a radical generator (for example, JP-A 63-142346), a photopolymerizable composition using hexaarylbisimidazole (for example, JP-A 5-27436), a photopolymerizable composition using a metal-allene complex (for example, JP-A 5-17525) and the like, respectively. ##STR2##
It is disclosed in JP-A 63-138345, JP-A 63-142346, JP-A 2-48665 and the like that a benzoindolenium salt compound represented by the above formula (A) has the maximum absorption wavelength at 673 nm. The benzoindolenium salt compound has a problem that, although it can effectively sensitize various red lasers, for example, He--Ne laser, Kr laser, short wavelength semiconductor laser due to the above property, since it has the low solubility in an organic solvent or a monomer, the higher concentration in a photosensitizer solution can not be obtained and, therefore, the use of solvents having the low toxicity, for example, methyl ethyl ketone is limited. In addition, the benzoindolenium salt compound has also a problem that, since it is easily degraded in the dark even when stored with the light screened in a photosensitizer solution, the photosensitizer solution is discolored in a red region and the photosensitivity of the solution to the red light is remarkably lowered in a short period of time.
DISCLOSURE OF THE INVENTION
The present invention relates to a photopolymerizable composition which comprises a squarylium compound represented by the formula (I): ##STR3## wherein R represents lower alkyl having 2 to 8 carbon atoms, a radical generator and an addition-polymerizable compound having at least one ethylenic unsaturated double bond.
According to the present invention, there is also provided a squarylium compound represented by the formula (Ia): ##STR4## wherein R.sup.a represents propyl, isopropyl, isobutyl, pentyl, isopentyl or hexyl.
Hereinafter, compounds represented by the formula (I) and (Ia) are referred to as "Compound (I)" and "Compound (Ia)", respectively. The same applies to the compounds of other formula numbers.
In the definition of the formula (I), examples of lower alkyl having 2 to 8 carbon atoms are straight or branched alkyls such as ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, 2-ethylbutyl, pentyl, isopentyl, neopentyl, 3-ethylpentyl, tert-pentyl, hexyl, isohexyl, heptyl, octyl and the like.
Then, a process for preparation of Compound (I) is described below: ##STR5## (In the formula, R has the same meaning as defined above, and X represents halogen or p-toluenesulfonyloxy.)
As used herein, halogen represents chlorine, bromine or iodine.
A raw compound (II) can be obtained according to a process described in Monatsh. Chem., 31, 123 (1910) or a similar process thereto.
Step 1
Compound (III) can be prepared by reacting Compound (II) with an equivalent to a large excess amount of compound RX in a solvent or without a solvent under heatin
REFERENCES:
patent: 4743530 (1988-05-01), Farid et al.
patent: 4743531 (1988-05-01), Farid et al.
patent: 4997745 (1991-03-01), Kawamura et al.
patent: 5147758 (1992-09-01), Smothers et al.
patent: 5275917 (1994-01-01), Inaishi
World Patent Index Acct. No. C92-1468, Abstract of Japanese Document JP 04106548A Date 920408.
Kinoshita Hirotaka
Koseki Kenichi
Matsushita Shoshiro
Shimizu Ikuo
Toyoda Hiroshi
Hamilton Cynthia
Kyowa Hakko Kogyo Co. Ltd.
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