# US 9,751,968 B2 · Vinyl alcohol polymer, thickening agent, stabilizer for emulsion polymerization, stabilizer for suspension polymerization, coating agent, coated article, sizing agent for fibers, sized yarn, and production method of textile

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- Number: US 9,751,968 B2
- Document ID: US9751968B2
- Status: Granted
- Kind: B2
- Application number: 15/021,305
- Filed: 2014-09-11
- Published: 2016-09-01
- Granted: 2017-09-05
- Earliest claimed: 2013-09-13
- Assignees: Kuraray Co., Ltd.
- Applicants: Kuraray Co., Ltd.
- Inventors: Masaki Kato; Hideki Maki; Keishi Hachiya; Masako Kawagoe; Yoko Mori
- Web page: https://patentgrep.com/patent/US9751968B2

## CPC

- C08F 216/06: Polyvinyl alcohol {; Vinyl alcohol}
- B41M 5/337: Additives; Binders {(B41M5/46 takes precedence)}
- B41M 5/5254: {characterised by the use of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers}
- B65D 65/42: Applications of coated or impregnated materials
- C08F 8/12: Hydrolysis
- C08F 8/14: Esterification
- C08F 16/00: Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F 218/08: Vinyl acetate
- C09D 129/04: Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids
- D06M 15/333: of vinyl acetate; Polyvinylalcohol
- D21H 17/36: Polyalkenyalcohols; Polyalkenylethers; Polyalkenylesters
- D21H 19/20: comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D21H 19/60: Polyalkenylalcohols; Polyalkenylethers; Polyalkenylesters
- D21H 21/16: Sizing or water-repelling agents
- D21H 27/001: {Release paper}
- D21H 27/10: Packing paper (packaging materials of special type or form B65D65/38)
- B41M 2205/02: Dye diffusion thermal transfer printing (D2T2)
- B41M 2205/32: Thermal receivers
- C08F 2800/10: as molar percentages
- C08F 2800/20: as weight or mass percentages
- C08F 2810/20: leading to a crosslinking, either explicitly or inherently
- C08J 2429/04: Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- B41M: PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING, (correction of typographical errors B41J; processes for applying transfer pictures or the like B44C1/16; fluid media for correction of typographical errors by coating C09D10/00; printing textiles D06P)
- B65D: CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- 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)
- D06M: TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D21H: PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- 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

Provided by the present invention is a PVA having highly harmonized adequate water solubility, thickening property and coating film strength, and having superior storage stability in terms of the viscosity in an aqueous solution. A vinyl alcohol polymer having a ratio (Mw (A)/Mn (A)) of the weight average molecular weight (Mw (A)) to the number average molecular weight (Mn (A)) of 3 or greater and 8 or less, and being capable of giving a vinyl alcohol polymer having a ratio (Mw/Mn) of a weight average molecular weight (Mw) to a number average molecular weight (Mn) of 2 or greater and less than 3 when treated at 40° C. for 1 hour in a sodium hydroxide solution.

## Claims

### Claim 1

A vinyl alcohol polymer, wherein:
a ratio (Mw/Mn) of a weight average molecular weight (Mw) to a number average molecular weight (Mn) of the vinyl alcohol polymer is in a range of 3 to 8;
the vinyl alcohol polymer comprises a branched structure formed by binding, the binding being cleavable under an alkaline condition; and
when the vinyl alcohol polymer is treated at 40° C. for 1 hour in a sodium hydroxide solution to cleave the binding, a resulting vinyl alcohol polymer has a ratio (Mw/Mn) of 2 or greater and less than 3.

### Claim 2 (depends on 1)

The vinyl alcohol polymer according to claim 1, obtained by:
polymerizing a vinyl ester monomer in the presence of at least one monomer selected from the group consisting of a carboxylic acid having an unsaturated double bond, an alkyl ester thereof, an acid anhydride thereof, and a salt thereof, and a silyl compound having an unsaturated double bond; and
thereafter saponifying and carrying out a heat treatment of the polymerization product at a temperature of 70° C. to 150° C.

### Claim 3 (depends on 1)

A thickening agent comprising the vinyl alcohol polymer according to claim 1.

### Claim 4 (depends on 1)

A stabilizer comprising the vinyl alcohol polymer according to claim 1, wherein the stabilizer is suitable for emulsion polymerization.

### Claim 5 (depends on 4)

The stabilizer according to claim 4, further comprising water.

### Claim 6 (depends on 1)

A stabilizer comprising the vinyl alcohol polymer according to claim 1, wherein the stabilizer is suitable for suspension polymerization.

### Claim 7 (depends on 6)

The stabilizer according to claim 6, further comprising water.

### Claim 8 (depends on 1)

A coating agent comprising the vinyl alcohol polymer according to claim 1.

### Claim 9 (depends on 8)

The coating agent according to claim 8, further comprising a crosslinking agent.

### Claim 10 (depends on 8)

A coated article produced by applying the coating agent according to claim 8 on a surface of a base material.

### Claim 11 (depends on 10)

The coated article according to claim 10, which is a thermal recording paper.

### Claim 12 (depends on 10)

The coated article according to claim 10, which is a base paper for release paper.

### Claim 13 (depends on 10)

The coated article according to claim 10, which is an oil resistant paper.

### Claim 14 (depends on 1)

A sizing agent comprising the vinyl alcohol polymer according to claim 1.

### Claim 15 (depends on 14)

The sizing agent according to claim 14, further comprising a wax.

### Claim 16 (depends on 14)

A sized yarn comprising a raw yarn, and a binder with which the raw yarn is impregnated, wherein the binder comprises the sizing agent according to claim 14.

### Claim 17 (depends on 16)

A method of producing a textile, comprising weaving the sized yarn according to claim 16.

### Claim 18 (depends on 1)

The vinyl alcohol polymer according to claim 1, comprising a unit derived from at least one monomer selected from the group consisting of a carboxylic acid having an unsaturated double bond, an alkyl ester of the carboxylic acid, an acid anhydride of the carboxylic acid, a salt of the carboxylic acid, and a silyl compound having an unsaturated double bond, wherein the unit is present in an amount of 0.02 to 5 mol % based on a total number of moles of all monomer units constituting the vinyl alcohol polymer.