# US 5,350,601 A · Process for making and using polymeric film coated with primer coating for silicone release applications

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- Number: US 5,350,601 A
- Document ID: US5350601A
- Status: Granted
- Kind: A
- Application number: 07/788,658
- Filed: 1991-11-06
- Granted: 1994-09-27
- Earliest claimed: 1991-11-06
- Assignees: Hoechst Celanese Corporation
- Inventors: Edwin C. Culbertson; Grover L. Farrar
- Web page: https://patentgrep.com/patent/US5350601A

## CPC

- C09D 167/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds (C09D167/06 takes precedence)
- B05D 5/08: to obtain an anti-friction or anti-adhesive surface (rendering particulate materials free-flowing in general, e.g. making them hydrophobic B01J2/30)
- C08J 7/0427: {with only one layer of a composition containing a polymer binder (with more layers C08J7/042)}
- C08J 7/043: Improving the adhesiveness of the coatings per se, e.g. forming primers (adhesives in the form of films or foils characterised by the primer layers between the polymer carriers and the adhesives C09J7/50)
- B05D 2201/00: Polymeric substrate or laminate
- C08J 2483/02: Polysilicates
- 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)
- B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02)
- 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

The present invention describes a process for priming a polymeric film with a primer coating composition and overcoating with a silicone release coating. Silicone release films are well known and serve as temporary supports for an adhesive or tacky surface such as for labels, pressure sensitive tape, etc. The primer coating composition, before dilution with water, comprises from about 25 to 75% by weight of a glycidoxy silane and from about 75 to 25% by weight of a copolyester. The copolyester comprises from about 40 to 98 mol percent isophthalic acid; from about 0 to about 50 mol percent of at least one aliphatic dicarboxylic acid; from about 2 to about 20 mol percent of at least one sulfonate group attached to a dicarboxylic nucleus; and about 100 mol percent of glycol having from about 2 to 11 carbon atoms. Typical glycidoxy silanes that can be employed in the primer coating composition include glycidoxypropyltrimethoxysilane.

## Claims

### Claim 1

A process for priming a polymeric film to bond to a silicone release coating, comprising:
a) priming a polymeric film with an aqueous-based primer coating, said primer coating comprising, before dilution:
i) from 25 to 75% by weight of a glycidoxy silane; and
ii) from 75 to 25% by weight of a copolyester mixture, said copolyester mixture comprising:
a) from about 40 to 98 mol percent isophthalic acid;
b) from about 0 to about 50 tool percent of at least one aliphatic dicarboxylic acid;
c) from about 2 to about 20 tool percent of at least one sulfomonomer containing a sulfonate group attached to a dicarboxylic nucleus;
d) about 100 mol percent of glycol having from about 2 to 11 carbon atoms; and
b) drying said primer coating on said polymeric film.

### Claim 2 (depends on 1)

The process of claim 1, wherein said glycidoxy silane is represented by the formula X--Y--Si--R.sub.1 R.sub.2 R.sub.3, wherein X is a glycidoxy group, Y is an alkylene group, R.sub.1 and R.sub.2 are hydrolyzable groups, and R.sub.3 is a hydrolyzable or non-hydrolyzable group.

### Claim 3 (depends on 2)

The process of claim 2, wherein said glycidoxy silane is glycidoxypropyltrimethoxysilane or glycidoxypropylmethyldiethoxysilane.

### Claim 4 (depends on 1)

The process of claim 1, wherein said aliphatic dicarboxylic acid is selected from the group consisting of malonic, adipic, azelaic, glutaric, sebacic, suberic, succinic, brassylic and mixtures thereof.

### Claim 5 (depends on 1)

The process of claim 1, wherein said sulfomonomer is represented by the formula: ##STR4## wherein M is a monovalent cation of an alkali metal, ammonium, substituted ammonium, or quaternary ammonium; Z is a trivalent radical; and X and Y are carboxyl groups or polyester forming equivalents.

### Claim 6 (depends on 5)

The process of claim 5, wherein said sulfomonomer is selected from the group consisting of ammonium sulfoterephthalic acid, alkali metal sulfoterephthalic acid, ammonium 5-sulfoisophthalic acid, alkali metal 5-sulfoisophthalic acid, ammonium sulfophthalic acid, alkali metal sulfophthalic acid, 5-(p-ammoniumsulfophenoxy)isophthalic acid, 5-(sulfopropoxy)-isophthalic acid and sodium salt.

### Claim 7 (depends on 1)

The process of claim 1, wherein glycol is selected from the group consisting of ethylene glycol; butanediol; 1,5-pentanediol; 1,6-hexanediol; neopentyl glycol; 1,10-decanediol; cyclohexanedimethanol; and diethylene glycol.

### Claim 8 (depends on 1)

The process of claim 1, wherein said glycidoxysilane is glycidoxypropyltrimethoxysilane, said sulfomonomer is sodium 5-sulfoisophthalic acid, and said glycol is ethylene glycol.

### Claim 9 (depends on 1)

The process of claim 1, wherein said polymeric film is coated on both sides with said primer coating.

### Claim 10 (depends on 1)

The process of claim 1, wherein said primer coating on said film after drying is from about 1.times.10.sup.-7 to 1.times.10.sup.-4 inch thick.

### Claim 11 (depends on 1)

The process of claim 1, wherein said polymeric film is polyamides, polyolefins, polyesters, polyacetal, or polycarbonate.

### Claim 12

A process for bonding a silicone release coating to a polymeric film, comprising:
a) priming a polymeric film with an aqueous-based primer coating, said primer coating comprising, before dilution:
i) from 25 to 75% by weight of a glycidoxy silane; and
ii) from 75 to 25% by weight of a copolyester mixture, said copolyester mixture comprising:
a) from about 40 to 98 mol percent isophthalic acid;
b) from about 0 to about 50 mol percent of at least one aliphatic dicarboxylic acid;
c) from about 2 to about 20 mol percent of at least one sulfomonomer containing a sulfonate group attached to a dicarboxylic nucleus;
d) about 100 mol percent of glycol having from about 2 to 11 carbon atoms;
b) drying said primer coating on said polymeric film thereby forming a dried primed film; and
c) coating said dried primed film with a silicone release composition such that it bonds to said dried primed film, said coating applied at an effective amount to prevent an adhesive backed article from adhering to said polymeric film.

### Claim 13 (depends on 12)

The process of claim 12 wherein said silicone release composition is solvent-based silicone coatings or, solvent-free silicone coatings.

### Claim 14 (depends on 12)

The process of claim 12, wherein said glycidoxy silane is represented by the formula X--Y--Si--R.sub.1 R.sub.2 R.sub.3, wherein X is a glycidoxy group, Y is an alkylene group, R.sub.1 and R.sub.2 are hydrolyzable groups, and R.sub.3 is a hydrolyzable or non-hydrolyzable group.

### Claim 15 (depends on 12)

The process of claim 12, wherein said glycidoxy silane is glycidoxypropyltrimethoxysilane glycidoxypropylmethyldiethoxysilane.

### Claim 16 (depends on 12)

The process of claim 12, wherein said aliphatic dicarboxylic acid is selected from the group consisting of malonic, adipic, azelaic, glutaric, sebacic, suberic, succinic, brassylic and mixtures thereof.

### Claim 17 (depends on 12)

The process of claim 12, wherein said sulfomonomer is represented by the formula: ##STR5## wherein M is a monovalent cation of an alkali metal, ammonium, substituted ammonium, or quaternary ammonium; Z is a trivalent radical; and X and Y are carboxyl groups or polyester forming equivalents.

### Claim 18 (depends on 17)

The process of claim 17, wherein said sulfomonomer is selected from the group consisting of ammonium sulfoterephthalic acid, alkali metal sulfoterephthalic acid, ammonium 5-sulfoisophthalic acid, alkali metal 5-sulfoisophthalic acid, ammonium sulfophthalic acid, alkali metal sulfophthalic acid, 5-(p-ammoniumsulfophenoxy)-isophthalic acid, 5-(sulfopropoxy)-isophthalic acid and sodium salt.

### Claim 19 (depends on 12)

The process of claim 12, wherein glycol is selected from the group consisting of ethylene glycol; butanediol; 1,5-pentanediol; 1,6-hexanediol; neopentyl glycol; 1,10-decanediol; cyclohexanedimethanol; and diethylene glycol.

### Claim 20 (depends on 12)

The process of claim 12, wherein said glycidoxysilane is glycidoxypropyltrimethoxysilane, said sulfomonomer is sodium 5-sulfoisophthalic acid, and said glycol is ethylene glycol.

### Claim 21 (depends on 12)

The process of claim 12, wherein said polymeric film is coated on both sides with said primer coating.

### Claim 22 (depends on 12)

The process of claim 12, wherein said primer coating on said film after drying is from about 1.times.10.sup.-7 to 1.times.10.sup.-4 inch thick.

### Claim 23 (depends on 12)

The process of claim 12, wherein said polymeric film is polyamides, polyolefins, polyesters, polyacetal, or polycarbonate.

### Claim 24 (depends on 12)

The process of claim 12, wherein said priming step, said drying step, and said coating step occur in-line during the manufacturing process for producing the polymeric film.

### Claim 25 (depends on 12)

The process of claim 12, wherein said priming said polymeric film occurs in-line during the manufacturing process of the polymeric film and said coating step occurs off-line after heat-setting the polymeric film.

### Claim 26 (depends on 13)

The process of claim 13 wherein said solvent based silicone coatings are aqueous based silicone coatings.

### Claim 27 (depends on 13)

The process of claim 13 wherein said solvent free silicone coatings are ultraviolet curable coatings or electron beam curable coatings.