Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Compositions to be polymerized by wave energy wherein said...
Reexamination Certificate
2002-09-27
2004-09-28
Seidleck, James J. (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Compositions to be polymerized by wave energy wherein said...
C522S008000, C522S009000, C522S016000, C522S026000, C522S063000, C544S180000, C544S193000
Reexamination Certificate
active
06797739
ABSTRACT:
BACKGROUND OF THE INVENTION
(a) Field of the Invention
The present invention relates to a photosensitive composition, more particularly to a triazine-based compound comprising functionalized alkylthio groups of which long-term storage characteristics at room temperature as well as effects as a photopolymerization initiator are superior when it is used as a photosensitive composition.
(b) Description of the Related Art
Photosensitive compositions are polymerizable compounds having ethylenically unsaturated bonds containing photopolymerization initiators, and are being used in photo-curable inks, photosensitive printing plates, varieties of photoresists and color filters for Liquid Crystal Displays, etc., since photosensitive compositions can be polymerized and cured by irradiating light on them.
Although various types of photopolymerization initiators used in these photosensitive compositions include acetophenone derivatives, benzophenone derivatives, acrylphosphine oxide derivatives, triazine derivatives, etc., halomethyl triazine compounds which are decomposed by right irradiation thus generating halogen radicals are frequently among them. Particularly, the sensitivities of 2-aryl-4,6-bis(trihalomethyl)-s-triazine among halomethyl trazine compounds are known to be relatively superior.
For example, the use of a compound using two ringed or multi-ringed aromatic groups, or complex ring type aromatic groups such as No. 2 position aryl group is disclosed, and particularly it is written in Japanese Laid-open Patent Publication No. Showa 53-133428 that good results are obtained by using a naphthyl group as an aryl group. However, the sensitivities of compounds disclosed in Japanese Laid-open Patent Publication No. Showa 53-133428 are not to a degree of satisfaction in the practical applications, and the composition has demerits in that stabilities according to the time lapse of a photosensitive composition are lowered due to its use in large quantities or with a long light irradiation time, as well as insufficient solubility into a polymerizable compound having ethylenically unsaturated bonds.
Furthermore, although it is disclosed in Japanese Laid-open Patent Publication No. Showa 63-70243 that stabilities according to the time lapse of a photosensitive composition can be improved by employing substituents having amide bonds or ester bonds at No. 2 position naphthyl groups in the composition, the sensitivity as a photoinitiator was not satisfactory in that case as well. Additionally, a photoinitiator having less molecular weight and large crystallinity has a problem in that it migrates onto the coated film surface or crystallizes in the film after coatings decreasing the photoinitiation efficiencies.
Methods used to solve these problems include using initiators having strong interactions with binders, photoinitiators with large molecular weights, and multi-functional or poly-functional triazine-based photoinitiators.
A photoinitiator having two or more photoactive triazine groups is disclosed in U.S. Pat. No. 5,298,361 wherein triazine groups are coupled with aliphatic ether, urethane, ester, and amide bonds. 2-Aryl-4,6,-bis(trihalomethyl)-s-triazine based derivatives in which an amino group substituted phenyl group is employed at the No. 2 position are disclosed in U.S. Pat. No. 4,837,128. However, these compounds have limits in the applications requiring color purity since they have maximum absorbance over 350 nm and absorb light within the scope of visible rays despite their superior photoactivities.
Furthermore, 2-aryl-4,6-bis(trihalomethyl)-s-triazine based s derivatives in which phenyl groups coupled with simple alkyl or aryl groups by S, Se, or Te are employed at the No. 2 position are disclosed in European Patent No. 271195 A1. However, these compounds have problems in compatibility with binder polymers used in a photopolymerization composition, and with sublimation in the high temperature process when alkyl groups having less numbers of carbons are substituted, and they have limits in photoiniteation efficiencies with various light sources.
SUMMARY OF THE INVENTION
It is an object of the present invention to provide a triazine-based photoinitiator having functionalized alkylthio groups showing strong absorbance at 360 nm in order to solve existing photoinitiator problems such as compatibility, photoinitiation efficiency, and development process problems.
It is another object of the present invention to provide a compound of which long term storage characteristics at room temperature and effects as a photopolymerization initiator as well as coating characteristics are superior, and in which the development time can be controlled when it is used as a photosensitive composition.
The present invention provides a triazine compound having a functionalized alkylthio group represented in the following Chemical Formula 1, and a photopolymerization initiator comprising an active ingredient of the compound in order to accomplish the above objects.
wherein R
1
is selected from the group consisting of C
n
H
2n
CONH
2
(n is an integer from 1 to 12), C
n
H
2n
COOC
m
H
2m+1
(n is an integer from 1 to 12 and m is an integer from 0 to 12), (CH
2
)
n
COOC
m
H
2m
OC
l
H
2l+1
(n, m, and l are each independent integers from 1 to 12), (CH
2
)
n
COO-cyclo-C
m
H
2m+1
(n is an integer from 1 to 12, and m is an integer from 3 to 12), C
n
H
2n
COOR
f
(n is an integer from 1 to 12, and R
f
is an alkyl group of which all or some of the hydrogen atoms are substituted with fluorine), and C
n
H
2n
COOR
6
(n is an integer from 1 to 12, and R
6
is an aryl group having from 6 to 14 carbon atoms or a C
1
~C
6
alkyl group having a C
6
~C
14
aryl group); and R
2
, R
3
, R
4
, and R
5
are each independently a hydrogen, a halogen, or an alkyl having from 1 to 6 carbon atoms, or alkoxyl groups having from 1 to 6 carbon atoms.
Halomethyl triazine compounds synthesized in order to accomplish the above objects have superior long term storage characteristics at mom temperature, can control the development time according to the employed functionalized alkylthio groups, and have photobleaching effects so that effects as a photopolymerization initiator do not greatly influence color filter photoresists when they are used in manufacturing color filters for liquid crystal displays.
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Cha Hyuk-Jin
Choi Dong-Chang
Kim Jin-Seuk
Kim Sung-Hyun
Lee Chul-Woo
Birch & Stewart Kolasch & Birch, LLP
LG Chemical Co. Ltd.
McClendon Sanza L.
Seidleck James J.
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