# US 2013/0156959 A1 · Single-layer film and hydrophilic material comprising the same

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- Number: US 2013/0156959 A1
- Document ID: US20130156959A1
- Status: Published application
- Kind: A1
- Application number: 13/812,779
- Filed: 2011-07-25
- Published: 2013-06-20
- Earliest claimed: 2010-07-29
- Assignees: Mitsui Chemicals, Inc.
- Inventors: Koju Okazaki
- Web page: https://patentgrep.com/patent/US20130156959A1

## CPC

- 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)
- C08F 2/38: Polymerisation using regulators, e.g. chain terminating agents {, e.g. telomerisation}
- C08F 222/102: {of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate}
- C08G 75/24: Polysulfonates
- C08J 7/0427: {with only one layer of a composition containing a polymer binder (with more layers C08J7/042)}
- C08J 7/044: Forming conductive coatings; Forming coatings having anti-static properties
- C08J 7/046: Forming abrasion-resistant coatings; Forming surface-hardening coatings
- C08J 7/054: Forming anti-misting or drip-proofing coatings
- C08J 7/056: Forming hydrophilic coatings
- 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: 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)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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)

## Abstract

There is stably provided a hydrophilic cured product, such as a single-layer film, in which anionic hydrophilic groups are concentrated at a surface that is in contact with the air and which is excellent in transparency and adhesion to a substrate and tends to be rarely cracked. The hydrophilic cured product or single-layer film comprising a resin composition is produced by applying a mixture containing a polyvalent monomer (II) having two or more (meth) acryloyl groups and a compound (IV) having a specific group and a sulfonic acid group to a substrate or the like, drying the mixture if necessary, and then performing polymerization.

## Claims

### Claim 1

A hydrophilic cured product obtained by polymerizing a mixture containing:
a polyvalent monomer (II) having two or more (meth)acryloyl groups, and a compound (IV) having at least one group selected from a mercapto group, a hydroxyl group and an amino group and having a sulfonic acid group (except a mono(meth)acrylate having at least one anionic hydrophilic group selected from a sulfonic acid group, a carboxyl group and a phosphoric acid group, and the polyvalent monomer (II)).

### Claim 2 (depends on 1)

The hydrophilic cured product as claimed in claim 1, wherein the compound (IV) contained in the mixture is at least one compound selected from a group of compounds represented by the following general formulas (100), (200) and (300):
wherein D1 is a mercapto group, an amino group, a methylamino group or an ethylamino group, Z is a hydrogen ion, an ammonium ion, an amine ion, an alkaline metal ion or an alkaline earth metal ion of ½ atom, R1 and R2 are each independently H, a methyl group, an ethyl group, a methoxy group or an ethoxy group, and nn is an integer of 1 to 10,
wherein D2, R3 and SO3Z are each a group bonded to carbon on a ring contained in the above formula, each D2 is independently a mercapto group, an amino group, a methylamino group, an ethylamino group or a hydroxyl group, Z is a hydrogen ion, an ammonium ion, an amine ion, an alkaline metal ion or an alkaline earth metal ion of ½ atom, each R3 is independently H, a methyl group, an ethyl group, a methoxy group, an ethoxy group, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, k is an integer of 0 to 10, l and m are each independently an integer of 1 to 11, k, l and m are numbers satisfying the condition of k+l+m=2 to 6+2n, and n is an integer of 0 to 3,
wherein D2, R3 and SO3Z are each a group bonded to carbon on a ring contained in the above formula, each D2 is independently a mercapto group, an amino group, a methylamino group, an ethylamino group or a hydroxyl group, Z is a hydrogen ion, an ammonium ion, an amine ion, an alkaline metal ion or an alkaline earth metal ion of ½ atom, each R3 is independently H, a methyl group, an ethyl group, a methoxy group, an ethoxy group, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, r is an integer of 0 to 6, q and p are each independently an integer of 1 to 7, and p, q and r are numbers satisfying the condition of p+q+r=an integer of 2 to 8.

### Claim 3 (depends on 1)

The hydrophilic cured product as claimed in claim 1, wherein the amount of the compound (IV) added based on 100 parts by weight of the polyvalent monomer (II) is in the range of 0.01 to 200 parts by weight.

### Claim 4 (depends on 1)

The hydrophilic cured product as claimed in claim 1, wherein the mixture further contains a mono(meth)acrylate (I) having at least one anionic hydrophilic group selected from a sulfonic acid group, a carboxyl group and a phosphoric acid group.

### Claim 5 (depends on 4)

The hydrophilic cured product as claimed in claim 4, wherein the amount of the compound (IV) added based on 100 parts by weight of the total amount of the mono(meth)acrylate (I) and the polyvalent monomer (II) is in the range of 0.01 to 200 parts by weight.

### Claim 6 (depends on 1)

A single-layer film formed from the hydrophilic cured product as claimed in claim 1.

### Claim 7 (depends on 6)

The single-layer film as claimed in claim 6, wherein the degree of inclination (anion concentration ratio) (Sa/Da) of a surface concentration (Sa) of sulfonic acid groups, carboxyl groups and phosphoric acid groups that are anionic hydrophilic groups in the single-layer film to a deep part concentration (Da) of these anionic hydrophilic groups at the position of ½ of the film thickness of the single layer film is not less than 1.1.

### Claim 8 (depends on 6)

The single-layer film as claimed in claim 6, which has a water contact angle of not more than 30°.

### Claim 9 (depends on 6)

The single-layer film as claimed in claim 6, which has a water contact angle of not more than 10°.

### Claim 10 (depends on 6)

The single-layer film as claimed in claim 6, which has a film thickness of 0.05 to 500 μm.

### Claim 11

A process for producing a laminate including a single-layer film having an anionic hydrophilic group and formed on at least one surface of a substrate, comprising:
a step of preparing a mixture which contains a monomer composition containing a polyvalent monomer (II) having two or more (meth)acryloyl groups and a compound (IV) having at least one group selected from a mercapto group, a hydroxyl group and an amino group and having a sulfonic acid group (except a mono(meth)acrylate having at least one anionic hydrophilic group selected from a sulfonic acid group, a carboxyl group and a phosphoric acid group, and the polyvalent monomer (II)) and contains a solvent containing a compound having a solubility parameter σ of not less than 9.3 (cal/cm3),
a step of applying the mixture to at least one surface of a substrate,
a step of removing at least a part of the solvent from the mixture applied, and
a step of polymerizing the mixture having passed through the above steps.

### Claim 12 (depends on 1)

A monomer composition used for obtaining the hydrophilic cured product as claimed in claim 1, which contains the polyvalent monomer (II) having two or more (meth)acryloyl groups and the compound (IV) having at least one group selected from a mercapto group, a hydroxyl group and an amino group and having a sulfonic acid group (except a mono(meth)acrylate having at least one anionic hydrophilic group selected from a sulfonic acid group, a carboxyl group and a phosphoric acid group, and the polyvalent monomer (II)), said polyvalent monomer (II) and said compound (IV) being described in claim 1.