# US 11,440,304 B2 · Laminate and its production method

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- Number: US 11,440,304 B2
- Document ID: US11440304B2
- Status: Granted
- Kind: B2
- Application number: 16/775,339
- Filed: 2020-01-29
- Published: 2020-05-28
- Granted: 2022-09-13
- Earliest claimed: 2017-08-28
- Assignees: AGC Inc.
- Applicants: AGC Inc.
- Inventors: Kenji Ishizeki
- Web page: https://patentgrep.com/patent/US11440304B2

## CPC

- B32B 27/322: {comprising halogenated polyolefins, e.g. PTFE}
- C08J 7/0423: {with at least one layer of inorganic material and at least one layer of a composition containing a polymer binder}
- 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)
- B05D 5/083: {involving the use of fluoropolymers}
- B05D 7/546: {each layer being cured, at least partially, separately}
- B32B 7/04: Interconnection of layers
- B32B 15/04: comprising metal as the main or only constituent of a layer, {which is} next to another layer of {the same or of} a {different material (next to a bituminous or tarry layer B32B11/08; next to a water-setting substance layer B32B13/06; next to a glass layer B32B17/061; next to a cellulosic plastic layer B32B23/042)}
- B32B 27/08: of synthetic resin
- B32B 37/26: with at least one layer which influences the bonding during the lamination process, e.g. release layers or pressure equalising layers
- C03C 17/34: with at least two coatings having different compositions (C03C17/44 takes precedence)
- C08G 65/336: containing silicon
- C08J 7/06: with compositions not containing macromolecular substances
- C08J 7/12: Chemical modification
- C08K 5/3492: Triazines
- C09K 3/18: for application to surfaces to minimize adherence of ice, mist or water thereto (rendering particulate materials free flowing, in general, e.g. making them hydrophobic B01J2/30); Thawing or antifreeze materials for application to surfaces (used in liquids for heat-transfer, heat-exchange or heat-storage or for the production of heat or cold other than by combustion, e.g. radiator liquids, C09K5/00)
- B05D 3/0493: {using vacuum}
- B05D 2502/005: modified
- B05D 2506/10: Fluorinated polymers
- B05D 2518/10: Silicon-containing polymers
- B32B 2250/03: 3 layers
- B32B 2255/24: Organic non-macromolecular coating
- B32B 2307/73: Hydrophobic
- B32B 2307/756: Refurbishable, i.e. marks or scratches can be removed
- B32B 2313/04: Carbon
- B32B 2315/00: Other materials containing non-metallic inorganic compounds not provided for in groups B32B2311/00 - B32B2313/04
- B32B 2327/12: containing fluorine
- B32B 2419/00: Buildings or parts thereof
- B32B 2551/00: Optical elements
- B32B 2605/00: Vehicles
- C08J 2333/04: esters
- C08J 2475/14: Polyurethanes having carbon-to-carbon unsaturated bonds
- C08K 5/5477: {containing nitrogen in a heterocyclic ring}
- B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- 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)
- B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02)
- C03C: CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

To provide a laminate having a surface layer with a small water sliding angle. A laminate comprising a substrate, an interlayer formed on the substrate, and a surface layer formed on the interlayer, wherein the interlayer is a layer formed by using a triazine compound having at least one of a M-OH group (wherein M is a metal atom or a silicon atom) and a group capable of forming the M-OH group, at least one of an amino group and a mercapto group, and a triazine ring, and the surface layer is a layer formed by using a fluorinated ether compound having a poly(oxyperfluoroalkylene) chain, and at least one of a hydrolyzable group bonded to a silicon atom and a hydroxy group bonded to a silicon atom.

## Claims

### Claim 1

A laminate comprising:
a substrate,
an interlayer formed on the substrate, and
a surface layer formed on the interlayer,
wherein the interlayer is a layer formed of at least one triazine compound selected from the group consisting of compounds of formula TN-1, compounds of formula TN-2 and compounds of formula TS, and
the surface layer is a layer formed of a fluorinated ether compound having a poly(oxyperfluoroalkylene) chain, and at least one of a hydrolyzable group bonded to a silicon atom and a hydroxy group bonded to a silicon atom,
wherein AN1 is —N(RN1)—RN2—Si(RN3)Nn(ORN4)3-Nn or —N{RN2—Si(RN3)Nn(ORN4)3-Nn}2,
AN2 is —N(RN5)—RN6(NH2)Nm or —N{RN6 (NH2)Nm}2,
AN3 is AN1, AN2 or —N(RN7)—RN8,
AN4 is a bivalent linking group,
RN1, RN5 and RN7 are each independently a hydrogen atom or a monovalent hydrocarbon group,
RN2 is a bivalent linking group,
RN3 and RN8 are each independently a monovalent hydrocarbon group,
RN4 is a hydrogen atom or a monovalent hydrocarbon group,
RN6 is a (Nm+1) valent linking group,
Nn is an integer of from 0 to 2, and Nm is 1 or 2, and,
wherein AS is —N(RS4)—RS1—Si(RS2)Sn(ORS3)3-Sn or —N{RS1—Si(RS2)Sn(ORS3) 3-Sn}2,
RS1 is a single bond or a bivalent linking group,
RS2 is a monovalent hydrocarbon group,
RS3 and RS4 are each independently a hydrogen atom or a monovalent hydrocarbon group,
MS1 is a hydrogen atom or an alkali metal atom, and
Sn is an integer of from 0 to 2.

### Claim 2 (depends on 1)

The laminate according to claim 1, wherein the fluorinated ether compound is represented by formula 1:
[A—O—Z1—(RfO)m—]jZ2[—SiRnL3-n]q Formula 1
wherein A is a perfluoroalkyl group or -Q[—SiRnL3-n]k,
Q is a (k+1) valent linking group,
k is an integer of from 1 to 10,
R is a monovalent hydrocarbon group,
L is a hydrolyzable group or a hydroxy group,
is an integer of from 0 to 2,
Z1 is a single bond, a C1-20 oxyfluoroalkylene group having at least one hydrogen atom substituted by a fluorine atom, or a C1-20 poly(oxyfluoroalkylene) group having at least one hydrogen atom substituted by a fluorine atom,
Rf is a perfluoroalkylene group,
m is an integer of from 2 to 200,
Z2 is a (j+q) valent linking group, and
j and q are each independently an integer of at least 1.

### Claim 3 (depends on 2)

The laminate according to claim 2, wherein A is a perfluoroalkyl group.

### Claim 4 (depends on 1)

The laminate according to claim 1, wherein the substrate has, on the outermost surface on the interlayer side, a sapphire layer, a metal layer, a metal oxide layer, a diamond-like carbon layer or a resin layer.

### Claim 5 (depends on 1)

An article comprising the laminate according claim 1, wherein the article is an article for an electronic device, an article for a transport device, an article for a precision device, an article for an optical device or an article for building.

### Claim 6 (depends on 1)

A method for producing the laminate according to claim 1, comprising:
forming on the substrate by dry coating method or wet coating method the interlayer of at least one triazine compound selected from the group consisting of compounds of formula TN-1, compounds of formula TN-2 and compounds of formula TS, and
forming on the interlayer by dry coating method or wet coating method the surface layer of the all fluorinated ether compound having a poly(oxyperfluoroalkylene) chain, and at least one of a hydrolyzable group bonded to a silicon atom and a hydroxy group bonded to a silicon atom.

### Claim 7 (depends on 6)

The method according to claim 6, wherein the dry coating method is employed and the dry coating method comprises vacuum deposition.

### Claim 8 (depends on 6)

The method according to claim 6, wherein the method of forming the interlayer is by the wet coating method and the wet coating method comprises applying a composition containing the at least one triazine compound and a liquid medium on the substrate, and removing the liquid medium from an obtained coating film containing the liquid medium, and
the method of forming the surface layer is by the wet coating method and the wet coating method comprises applying a composition containing the fluorinated ether compound and a liquid medium to the interlayer, and removing the liquid medium from an obtained coating film containing the liquid medium.