# US 7,745,530 B2 · Aqueous emulsion resin compositions

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- Number: US 7,745,530 B2
- Document ID: US7745530B2
- Status: Granted
- Kind: B2
- Application number: 10/481,811
- Filed: 2002-06-28
- Published: 2004-09-30
- Granted: 2010-06-29
- Earliest claimed: 2001-06-28
- Assignees: Daikin Industries, Ltd.
- Inventors: Nobuo Mitsuhata; Tsunehiko Fuwa; Susumu Wada; Keiko Kunimasa; Haruhiko Mohri; Nobuo Fukita
- Web page: https://patentgrep.com/patent/US7745530B2

## CPC

- C09D 127/12: containing fluorine atoms
- C08F 259/08: on to polymers containing fluorine
- C08L 27/16: Homopolymers or copolymers or vinylidene fluoride
- C09D 127/16: Homopolymers or copolymers of vinylidene fluoride
- C08K 5/0025: {Crosslinking or vulcanising agents; including accelerators}
- C08L 33/06: of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L 2201/52: Aqueous emulsion or latex, e.g. containing polymers of a glass transition temperature (Tg) below 20°C
- Y10T 428/3154: Of fluorinated addition polymer from unsaturated monomers
- 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)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

The present invention provides an aqueous emulsion resin composition which comprises: (a) a resin composition containing at least one fluoroolefin polymer having crosslinkable group(s) at a terminus and/or a side chain of its molecule and at least one non-fluoroolefin polymer having crosslinkable group(s) at a terminus and/or a side chain of its molecule; and (b) at least one curing agent selected from the group consisting of isocyanates, melamines, hydrazides, carbodiimides, silanes and epoxides; and provides an aqueous emulsion resin compositions containing at least one chemically bonded product of a fluoroolefin polymer and a non-fluoroolefin polymer bonded to each other via at least one covalent bond at a terminus and/or a side chain of the molecules wherein one or both of the fluoroolefin polymer and the non-fluoroolefin polymer have crosslinkable group(s).

## Claims

### Claim 1

An aqueous emulsion resin composition which comprises:
(a) a resin composition containing at least one fluoroolefin polymer having crosslinkable group(s) at a terminus and/or a side chain of its molecule and at least one non-fluoroolefin polymer having crosslinkable group(s) at a terminus and/or a side chain of its molecule,
wherein the fluoroolefin polymer consists of a fluoroolefin and a crosslinkable group-containing fluoroolefin, the crosslinkable-group-containing fluoroolefin being at least one member selected from the group consisting of a compound represented by General formula (I):
CF2═CF(CF2)a—Y (I)
[wherein a is an integer from 1 to 10 and Y is SO3M or COOM (with M being H, NH4 or an alkali metal)];
a compound represented by General formula (II):
CF2=CF(CF2CFX)b—Y (II)
[wherein X is F or CF3, b is an integer from 1 to 5 and Y is SO3M or COOM (with M being H, NH4 or an alkali metal)];
a compound represented by General formula (III):
CF2=CF—O—(CFX)—Y (III)
[wherein X is F or CF3, c is an integer from 1 to 10 and Y is SO3M or COOM (with M being H, NH4 or an alkali metal)];
a compound represented by General formula (IV):
CF2═CF—O—(CF2CFX—O)d—CF2CF2Y (IV)
[wherein X is F or CF3, d is an integer from 1 to 10, and Y is SO3M or COOM (with M being H, NH4 or an alkali metal)];
a compound represented by General formula (V):
CH2CFCF2O—(CF(CF3)CF2—O)eCF(CF3)Y (V)
[wherein e is 0 or an integer from 1 to 10, and Y is SO3M or COOM (with M being H, NH4 or an alkali metal)];
a compound represented by General formula (VI):
CF2CFCF2—O—(CF(CF3)CF2—O)f—CF(CF3)Y (VI)
[wherein f is an integer from 1 to 10, and Y is SO3M or COOM (with M being H, NH4 or an alkali metal)]; and
a compound represented by General formula (VII):
CH2CFCF2Rf1-(CH2)gX1 (VII)
[wherein X1 is —CH2OH, —COOR1 (with R1 being H, C1 to C6 alkyl group, Na, K, Li or NH4),
and Rf1 represents a C1 to C40 alkylene group having atom/atoms substituted with fluorine or —ORf2-(Rf2 represents a C1 to C40 alkylene group having atom/atoms substituted with fluorine or a C3 to C50 ether group having atom/atoms substituted with fluorine); g is 0 or an integer from 1 to 6];
wherein the non-fluoroolefin polymer consists of a non-fluoroolefin monomer or non-fluoroolefin monomers, and
(b) an emulsifier-modified isocyanate wherein the modifying emulsifier is at least one member selected from the group consisting of polyoxyethylene alkyl ethers, polyoxyethylene monoalkylaryl ethers, polyoxyethylene sorbitan higher fatty acid esters, and polyoxyethylene mono higher fatty acid esters,
wherein the combination of the crosslinkable group in the fluoroolefin polymer and the crosslinkable group in the non-fluoroolefin polymer is hydroxyl group (fluoroolefin polymer)/hydroxyl group (non-fluoroolefin polymer), carboxyl group (fluoroolefin polymer)/hydroxyl group (non-fluoroolefin polymer), or sulfonic acid group (fluoroolefin polymer)/hydroxyl group (non-fluoroolefin polymer).

### Claim 2 (depends on 1)

A composition according to claim 1, wherein the fluoroolefin polymer is polyvinylidene fluoride.

### Claim 3 (depends on 1)

A composition according to claim 1, wherein the resin composition is prepared by a seed polymerization method.

### Claim 4 (depends on 1)

A composition according to claim 1, wherein the emulsifier-modified isocyanate is used in an amount of 1 to 50 parts by weight based on 100 parts by weight of the resin composition.

### Claim 5 (depends on 3)

A composition according to claim 3, wherein the resin composition has a particle size of from about 50 nm to about 400 nm.

### Claim 6 (depends on 5)

A composition according to claim 5, wherein the resin composition has a particle size of from about 50 nm to about 200 nm.

### Claim 7 (depends on 1)

A composition according to claim 1, wherein the non-fluoroolefin monomer contains a crosslinkable-group-containing non-fluoroolefin monomer.

### Claim 8 (depends on 1)

A composition according to claim 1, wherein the non-fluoroolefin monomer is at least one member selected from the group consisting of acrylic acid, methacrylic acid, maleic acid, crotonic acid, methyl acrylate, methyl methacrylate (MMA), acrylamide, methacrylamide, N-methylacrylamide, N-methylolacrylamide, N-butoxymethylacrylamide, N-methylolmethacrylamide, N-methylmethacrylamide, N-butoxymethylmethacrylamide, hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, glycidyl acrylate, glycidyl methacrylate, γ-trimethoxysilane methacrylate, y-triethoxysilane methacrylate, acrolein, and monomers represented by the general formula shown below:
CH2═CR1—COO—CHR2—CR3R4—CHO
(wherein R1 is H or CH3; R2 is H or a C1 to C3 alkyl group; R3 is a C1 to C3 alkyl group; and R4 is a C1 to C4 alkyl group).

### Claim 9 (depends on 5)

A composition according to claim 5, wherein the resin composition contains the non-fluoroolefin polymer in the range of 10 to 200 parts by weight based on 100 parts by weight of the fluoroolefin polymer.