Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Polymers from only ethylenic monomers or processes of...
Reexamination Certificate
1997-09-26
2003-01-21
Cain, Edward J. (Department: 1714)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Polymers from only ethylenic monomers or processes of...
C428S447000
Reexamination Certificate
active
06509430
ABSTRACT:
The present invention concerns a coating agent composition which has a rapid curing rate, and which can form a cured coating film that is superior in terms of water resistance, anti-static properties and gas barrier properties following curing, and a composite film which is formed by laminating a cured film of said coating agent composition.
It is known that composite films having superior gas barrier properties are obtained by coating an organic resin film with a composition consisting chiefly of an organosilane. Examples of such compositions include compositions consisting of tetramethyl orthosilicate, an alkoxysilane such as a vinyltrialkoxysilane and a polyvinyl alcohol (see Japanese Patent Application Kokai No.6-329821), and mixtures which consist of an amino-group-containingalkoxysilane and a compound which contains aromatic rings such as xylylene diisocyanate (see Japanese Patent Application Kokai No. 7-18221). Furthermore, a method is also known in which a packaging material with superior gas barrier properties is obtained by coating an organic resin film with vinylbenzyl(2-aminoethyl)-3-aminopropyltrimethoxysilane and curing this coating film by irradiation with high-energy radiation (see Japanese Patent Application Kokoku No. 5-73774). However, the compositions used in these methods all suffer from the drawback of a slow curing rate. Furthermore, the cured films obtained following curing have inferior water resistance, and show a drop in performance under conditions of high humidity.
It is an object of the present invention to provide a coating agent composition which has a rapid curing rate, and which can form a cured coating film that is superior in terms of water resistance, anti-static properties and gas barrier properties following curing, and a composite film which is formed by laminating a cured coating film of said coating agent composition.
The present invention provides a high-energy radiation curable coating agent composition which comprises (A) an amino-group-containingalkoxysilane, such as N-&bgr;-(N-vinylbenzylaminoethyl)-&ggr;-aminopropyltrimethoxysilane, which can be expressed by the general formula
wherein R
1
and R
2
are divalent hydrocarbon groups with 12 or fewer carbon atoms, R
3
is an alkyl group with 6 or fewer carbon atoms, a cycloalkyl group or a phenyl group, and R
4
is a hydrolyzable group selected from a set consisting of alkoxy groups and aryloxy groups, Q
1
, Q
2
and Q
3
are selected from the group consisting of hydrogen atoms and groups which can be expressed by the general formula X—C
6
H
4
—CH
2
— wherein X is a vinyl group or a hydrogen atom, with the proviso that at least one of said Q
1
, Q
2
and Q
3
groups are a group expressed by the general formula X—C
6
H
4
—CH
2
, n is 0, 1 or 2, and a is 0, 1 or 2, or a hydrochloride of the same, and (B) an organic compound which can be expressed by the general formula
wherein R
5
is a residue of an organic polyhydric alcohol containing alcoholic hydroxyl groups bonded to different carbon atoms, or a residue of an ester formed by such an organic polyhydric alcohol and a polybasic acid, R
6
is a hydrogen atom or a methyl group, and b is an integer from 2 to 6. Also in accordance with the present invention, a composite film is formed by laminating a cured coating film of the above-mentioned coating agent composition on at least one side of an organic resin film.
In the above general formula which describes (A), R
1
indicates a divalent hydrocarbon group which has 12 or fewer carbon atoms, e.g., an alkylene group such as a methylene group, ethylene group or propylene group, etc.; in particular, an ethylene group is especially desirable. R
2
indicates a divalent hydrocarbon group which has 12 or fewer carbon atoms, e.g., an alkylene group such as a methylene group, ethylene group or propylene group, etc., or an arylene group such as a phenylene group or tolylene group, etc.; in particular, a propylene group is especially desirable. R
3
indicates an alkyl group with 6 or fewer carbon atoms, a cycloalkyl group or a phenyl group; in particular, a methyl group is especially desirable. R
4
indicates a hydrolyzable group selected from a set consisting of alkoxy groups and aryloxy groups, e.g., methoxy groups, ethoxy groups and phenoxy groups; in particular, a methoxy group is especially desirable. Q
1
, Q
2
and Q
3
indicate groups which can be expressed by the general formula X—C
6
H
4
—CH
2
— (in the preceding formula, X indicates a vinyl group or a hydrogen atom, with a vinyl group being especially desirable) or hydrogen atoms, with at least one of said groups being a group expressed by the general formula X—C
6
H
4
—CH
2
— (in the preceding formula, X is the same as described above), n is 0, 1 or 2, and is preferably 1, a is 0,1 or 2, and is preferably 0.
Concrete examples of component (A) include N-&bgr;-(N-vinylbenzyl-N-benzyl)aminoethyl-&ggr;-aminopropyltrimethoxysilane or a hydrochloride of the same, N-&bgr;-N-vinylbenzylaminoethyl)-N-benzyl-&ggr;-aminopropyltrimethoxysilane or a hydrochloride of the same, N-&bgr;-(N-vinylbenzyl-N-benzyl)aminoethyl-N-benzyl-&ggr;-aminopropyltrimethoxysilane or a hydrochloride of the same, N-vinylbenzyl-N-benzyl-&ggr;-aminopropyltrimethoxysilane or a hydrochloride of the same, N-&bgr;-N-vinylbenzyl-N-benzyl)aminoethyl-N-benzyl-&ggr;-aminopropyltriethoxysilane or a hydrochloride of the same, N-&bgr;-(Nvinylbenzyl-N-benzyl)aminoethyl-N-benzyl-&ggr;-aminopropylmethyl-dimethoxysilane or a hycholride of the same, N-&bgr;-(N-vinylbenzyl-N-benzyl-&ggr;-aminopropylmethyl-dimethoxysilane or a hydrochloride of the same, N-&bgr;-(N-vinylbenzyl-N-benzyl)aminoethyl-N-benzyl-&ggr;-aminopropylmethoxydimethylsilane or a hydrochloride of the same, N-&bgr;-(N-vinylbenzyl-N-benzyl)aminoethyl-N-benzyl-&ggr;-aminobutyltrimethoxysilane or a hydrochloride of the same, N-&bgr;-(N-vinylbenzyl-N-benzyl) aminoethyl-N-benzyl-&ggr;-aminopentyltrimethoxysilane or a hydrochloride of the same, and N-&bgr;-(N-vinylbenzyl-N-benzyl)aminoethyl-N-benzyl-&ggr;-aminohexyl-trimethoxysilane or a hydrochloride of the same, etc. In cases where a high-viscosity compound is used, the compound may be diluted with a solvent prior to use. Examples of solvents which can be used include methanol, ethanol, 1-propanol, 2-propanol, toluene, xylene, hexane, 1,1,1-trichloroethane,n-butanol and dioxane, etc.
In the above general formula which describes (B), R
5
indicates a residue of an organic polyhydric alcohol containing alcoholic hydroxyl groups bonded to different carbon atoms, or a residue of an ester formed by such an organic polyhydric alcohol and a polybasic acid. Examples of such polyhydric alcohols include ethylene glycol, polyethylene glycols with a degree of polymerization of 2 to 30, propylene glycol, polypropylene glycols with a degree of polymerization of 2 to 30, 2,2,4-trimethyl-1,3-pentanediol,1,4-cyclohexanedimethanol,2,2-bis[4-(2-hydroxyethoxy)phenyl]propane,2,2-bis[4-(2-hydroxypropoxy)phenyl]propane,2,2-bis(4-hydroxyphenyl)propane,2,2-bis(4-hydroxycyclo-hexyl)propane,1,6-hexanediol, 1,5-pentadiol [sic], 2-ethyl-1,3-hexanediol, glycerol, trimethylolpropane and 1,2,6-hexanetriol, etc. Furthermore, examples of the above-mentioned poly basic acids include phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, terephthalic acid, adipic acid, sebacic acid, maleic acid and fumaric acid, etc. Concrete examples of such organic compounds include diethylene glycol diacrylate, tetraethylene glycol diacrylate, trimethylolpropanetriacrylate, pentaerythritol tetraacrylate and trimethylolpropanetrimethacrylate, etc.
It is desirable that the amount of component (B) that is used in the composition of the invention, be 1 to 10,000 parts by weight (preferably 50 to 2,000 parts by weight) per 100 parts by weight of component (A). In cases where the amount of component (B) that is added exceeds 10,000 parts by weight, there is a possibility that performance values of the cured product such as anti-static properties and gas barrier properties, etc., will be lost
Iwai Makoto
Naito Hiroyoshi
Cain Edward J.
De Cesare Jim L.
Dow Corning Toray Silicone Company, Ltd.
Jarnholm Alan R.
McKellar Robert L.
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