# US 5,348,771 A · Method of producing an oxygen barrier coating containing trimethoxysilyl functional pentadienoate

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- Number: US 5,348,771 A
- Document ID: US5348771A
- Status: Granted
- Kind: A
- Application number: 08/155,039
- Filed: 1993-11-19
- Granted: 1994-09-20
- Earliest claimed: 1993-11-19
- Assignees: Dow Corning Corporation
- Inventors: Chi-Long Lee; Ming-Hsiung Yeh
- Web page: https://patentgrep.com/patent/US5348771A

## CPC

- C09D 4/00: Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16}
- C08J 7/0427: {with only one layer of a composition containing a polymer binder (with more layers C08J7/042)}
- C08J 7/048: Forming gas barrier coatings
- C08J 2483/00: Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)

## Abstract

A composite films which exhibit low oxygen transmission rates. The film comprises a silane resin coated on a plastic substrate then cured by ultraviolet radiation. For the silane coating, this invention relies on a class of organosilicon compounds derived from 1) organohydrogensilanes or organohydrogensiloxanes and 2) propargyl esters of carboxylic acids containing a terminal aromatic hydrocarbon radical, where the carbopropynoxy group of the ester and the aromatic hydrocarbon radical are separated by at least two adjacent ethylenically unsaturated carbon atoms. If more than two of these carbon atoms are present they form a sequence of conjugated ethylenic double bonds which allows the polymer to cross-link upon exposure to ultraviolet radiation.

## Claims

### Claim 1

A method for producing a silane coated substrate, comprising:
(I) coating a plastic substrate with a silane solution comprising
(A) an organosilicon compound selected from the group consisting of silanes corresponding to the molecular formula
Q(R.sup.1 O).sub.3 Si
where Q represents the radical
R.sup.2 (CH.dbd.CH).sub.n --CH.dbd.CR.sup.3 C(O)R.sup.5 --,
each R.sup.1 is individually selected from the group consisting of unsubstituted monovalent. hydrocarbon radicals, R.sup.2 represents an aryl, alkoxyaryl or alkaryl radical, R.sup.3 is --C.dbd.N or --C(O)OR.sup.4 where R.sup.4 is hydrogen or an unsubstituted monovalent hydrocarbon radical selected from the same group as R.sup.1, R.sup.5 is O(CH.sub.2).sub.a CH.dbd.CH-- or --NR.sup.6 --(CH.sub.2).sub.b --, R.sup.6 is a hydrogen or hydrocarbon radical having from 1 to 6 carbon atoms, a is 1 to 5, b is 3 to 6, and n is 0 or a positive integer, with the proviso that n can be 0 only when R.sup.2 represents a naphthyl radical;
(B) itaconic acid;
(C) water; and
(D) a solvent; and
(II) curing the silane solution to a silicone resin with ultraviolet light.

### Claim 2 (depends on 1)

The method of claim 1 wherein the solvent methanol or methyl ethyl ketone.

### Claim 3 (depends on 1)

The method of claim 1, wherein said silane solution is made from the following reactants comprising:
(a) propargyl 2-cyano-5-phenyl-2,4,-pentadienoate;
(b) toluene;
(c) a platinum catalyst; and
(d) trimethoxy silane.

### Claim 4 (depends on 1)

The method of claim 1, wherein said silane solution is made from the following reactants comprising:
(a) methyl 2-cyano-5-phenyl-2,4-pentadienoate;
(b) 3-aminopropyltrimethoxysilane;
(c) toluene.

### Claim 5

A coating composition, comprising:
(A) an organosilicon compound selected from the group consisting of silanes corresponding to the molecular formula
Q(R.sup.1 O).sub.3 Si
where Q represents the radical
R.sup.2 (CH.dbd.CH).sub.n --CH.dbd.CR.sup.3 C(O)R.sup.5 --,
each R.sup.1 is individually selected from the group consisting of unsubstituted monovalent hydrocarbon radicals, R.sup.2 represents an aryl, alkoxyaryl or alkaryl radical, R.sup.3 is --C.dbd.N or --C(O)OR.sup.4 where R.sup.4 is hydrogen or an unsubstituted monovalent hydrocarbon radical selected from the same group as R.sup.1, R.sup.5 is --O(CH.sub.2).sub.a CH.dbd.CH-- or --NR.sup.6 --(CH.sub.2).sub.b ', R.sup.6 is a hydrogen or hydrocarbon radical having from 1 to 6 carbon atoms, a is 1 to 5, b is 3 to 6, and n is 0 or a positive integer, with the proviso that n can be 0 only when R.sup.2 represents a naphthyl radical;
(B) itaconic acid;
(C) water; and
(D) a solvent

### Claim 6 (depends on 5)

The coating composition of claim 5 wherein the solvent is methanol or methyl ethyl ketone.

### Claim 7 (depends on 5)

The coating composition of claim 5 wherein the composition is made from the following reactants comprising:
(a) propargyl 2-cyano-5-phenyl-2,4-pentadienoate;
(b) toluene;
(c) a platinum catalyst; and
(d) trimethoxy silane.

### Claim 8 (depends on 5)

The coating composition of claim 5 wherein the composition is made from the following reactants comprising:
(a) methyl 2-cyano-5-phenyl-2,4-pentadienoate;
(b) 3-aminopropyltrimethoxysilane;
(c) toluene.