Sulfonium salt-containing compounds and initiators of polymeriza

Details Sulfonium salt-containing compounds and initiators of polymeriza Sulfonium salt-containing compounds and initiators of polymeriza

1996-09-04

1998-08-25

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 25, 522 31, 522170, 522181, 522188, 522167, 526222, 528 90, 528408, 528410, 568 18, 568 39, 568 42, 568 43, 568 53, 568 54, 568 55, 568 56, 568 74, 568 75, 568 77, C08F 250, C08F 400, C07C38112

Patent

active

057983968

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

The present invention is related to novel sulfonium salt-containing compounds and hardening compositions comprising said compounds, and more particularly to cationic hardening compositions of which film with a thickness ranging from very thin to thick can harden in a short time under heating or irradiation of active energy ray, such as light, electronic ray and X-ray. The hardened-products of said cationic hardening compositions have excellent physical properties, and therefore, those can be used for coating materials, adhesives, photoresists, etc.


BACKGROUND ART

The sulfonium salt-containing compounds similar to the ones specified in the present invention are described in Japanese Patent Laid-Opened No. Sho 50-151997, No. Sho 50-158680 and No. Hei 2-178303, respectively, wherein it is disclosed that the sulfonium salt-containing compounds can be used as a catalyst for hardening of cationic polymerizable compounds, such as epoxy compounds, under the application of radiation, such as light, electronic ray and X-ray.
However, the sulfonium salt-containing compounds described in the Japanese Patent Laid-opened No. Sho 50-151997 is effective for photo-setting, but said compounds have problems such that those can be hardly used for the hardening of thick films due to almost no-effectiveness as a catalyst for thermo-setting, expensive production cost owing to complicated synthesizing processes, and low solubility to monomers. Also, the compounds disclosed in the Japanese Patent Laid-Opened No. Hei 2-178303 can harden thick films since those can work as a catalyst for thermo-setting, however, those have very poor activity as a catalyst for photo-setting and have less solubility to monomers. Again, aliphatic compounds containing sulfonium salt reported by Endo et al. (IUPAC MACRO 88 PREPR. 90 (1988)) can work as a catalyst for thermo-setting and are capable of hardening thick films, however, those activity as a catalyst for photo-setting is very poor.


DISCLOSURE OF THE INVENTION

It is an object of the present invention to provide sulfonium salt-containing compounds which have high sensitivity to either heat or irradiation of active energy ray, such as light, electronic ray and X-ray, as well as to provide cationic hardening compounds, of which film with a thickness ranging from very thin to thick can harden in a short time and the hardened-product thereof shows to have excellent physical properties.
The inventors of the present invention made various examinations for aiming at accomplishing the object described above, then found that a hardening composition comprising sulfonium salt-containing compound, sensitizer and cationic polymerizable compound, of which film with a thickness ranging from very thin to thick can harden when it is subjected to either heating or irradiation of active energy ray, such as light, electronic ray and X-ray and the hardened product thereof has excellent physical properties, thereby completed the present invention.
The present invention is directed to sulfonium salt-containing compounds as represented by a following general formula (I); ##STR3## wherein R.sub.1 is alkyl containing from 1 to 18 carbon atoms, hydroxy, alkoxy containing from 1 to 18 carbon atoms, alkylcarbonyl containing from 1 to 18 carbon atoms or halogen, n is any of 0, 1, 2 or 3, however, R may be different from the groups above when n is 2 or more, R.sub.2 is alkyl containing from 1 to 6 carbon atoms, R.sub.3 and R.sub.4 are each independently hydrogen or alkyl containing from 1 to 6 carbon atoms, R.sub.5 and R.sub.6 are each independently hydrogen, alkyl containing from 1 to 6 carbon atoms, hydroxy, alkoxy containing from 1 to 6 carbon atoms, alkylcarbonyl containing from 1 to 18 carbon atoms or aromatic carbonyl, R.sub.7 is alkyl containing from 4 to 20 carbon atoms or a group represented by a following formula; ##STR4## wherein R.sub.8 is alkyl containing from 1 to 18 carbon atoms, hydroxy, alkoxy containing from 1 to 18 carbon atoms, alkylcarbonyl containing from 1 to 18 carbon atoms

REFERENCES:
patent: 3133971 (1964-05-01), MacGregor
patent: 5159088 (1992-10-01), Schwalm
patent: 5399596 (1995-03-01), Kouge et al.
patent: 5648196 (1997-07-01), Frechet et al.
Japan. kOKAI No. 58-37003, P.T.O. translation, Mar. 4, 1983.

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