# US 2023/0068751 A1 · Curable composition

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- Number: US 2023/0068751 A1
- Document ID: US20230068751A1
- Status: Published application
- Kind: A1
- Application number: 17/785,414
- Filed: 2020-12-10
- Published: 2023-03-02
- Earliest claimed: 2019-12-19
- Assignees: Momentive Performance Materials Japan LLC; Daikin Industries, Ltd.
- Applicants: Momentive Performance Materials Japan LLC; Daikin Industries, Ltd.
- Inventors: Isao IIDA; Kazuhisa ONO; Tetsuo FUJIMOTO; Kazuki MARUHASHI; Hisashi MITSUHASHI
- Web page: https://patentgrep.com/patent/US20230068751A1

## CPC

- C08G 77/46: containing polyether sequences
- C08L 83/08: containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G 65/007: {containing fluorine}
- C08G 65/336: containing silicon
- C08L 71/00: Compositions of polyethers obtained by reactions forming an ether link in the main chain (of polyacetals C08L59/00; of epoxy resins C08L63/00; of polythioether-ethers C08L81/02; of polyether-sulfones C08L81/06); Compositions of derivatives of such polymers
- C08G 77/24: halogen-containing groups
- C08G 77/26: nitrogen-containing groups
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

A curable composition includes: (A) a perfluoro(poly)ether group-containing silane compound having two or more Si atoms bonded to at least one group selected from the group consisting of a hydroxyl group and hydrolyzable groups; (B) a compound having at least two OR2 groups (in the formula, R2 is independently a hydrogen atom or a monovalent organic group at each occurrence) bonded to an Si atom (provided that (A) and (D) are excluded) or a partially hydrolyzed condensate thereof; (C) a condensation catalyst; and (D) a compound containing two or more alkoxysilyl groups in one molecule or a partially hydrolyzed condensate thereof (provided that (A) is excluded), with the linking group between the alkoxysilyl groups being a group other than that selected from the group consisting of an —O— group and a group having a siloxane bond.

## Claims

### Claim 1

A curable composition comprising:
(A) a perfluoro(poly)ether group-containing silane compound having two or more Si atoms bonded to at least one group selected from the group consisting of a hydroxyl group and a hydrolyzable group,
(B) a compound having at least two OR2 groups bonded to an Si atom, wherein R2s are each independently a hydrogen atom or a monovalent organic group at each appearance, provided that (A) and (D) are excluded, or a partially hydrolyzed condensate thereof,
(C) a condensation catalyst, and
(D) a compound containing two or more alkoxysilyl groups in one molecule, with the linking group between the alkoxysilyl groups being a group other than that selected from the group consisting of an —O— group and a group having a siloxane bond, or a partially hydrolyzed condensate thereof, provided that (A) is excluded.

### Claim 2 (depends on 1)

The curable composition according to claim 1, wherein
Component (A) is a compound represented by the formula (1)
wherein,
Rfs are at each appearance each independently a perfluoro(poly)ether group represented by the formula:
—(CfF2f)—(OCF2)a1—(OC2F4)a2—(OC3X106)a3—(OC4F8)a4—(OC5F10)a5—(OC6F12)a6—(OC7F14)a7—(OC8F16)a8—
wherein, f is an integer of 1 to 10, a1, a2, a3, a4, a5, a6, a7 and a8 are each independently an integer of 0 or more and 200 or less, a sum of a1, a2, a3, a4, a5, a6, a7 and a8 is an integer of 5 or more and 200 or less, the unit represented by (CfF2f) is located at the left end of the group, the order of existence of each repeating unit enclosed in parentheses with the subscript a1, a2, a3, a4, a5, a6, a7 or a8 is arbitrary in the formula, and X10s are each independently a hydrogen atom, a fluorine atom or a chlorine atom at each appearance, provided that when all X10s are hydrogen atoms or chlorine atoms, at least one of a1, a2, a4, a5, a6, a7 and a8 is an integer of 1 or more,
g is an integer of 0 or more,
j and k are each an integer of 1 to 9,
h and i are each independently an integer of 0 to 3 at each appearance, provided that at least two among h and i existing with a number of j+k are made to be 0 or 1,
X1s each independently represent a single bond or a divalent organic group at each appearance,
X1′s each independently represent a divalent organic group at each appearance,
X2 represents a j+l valent organic group,
X2′ represents a k+l valent organic group,
R3s each independently represent a hydrogen atom or a monovalent organic group at each appearance, and
R4s each independently represent a hydrogen atom or a monovalent organic group at each appearance, provided that R4 is not to be OR3.

### Claim 3 (depends on 2)

The curable composition according to claim 2, wherein
in the formula (1), Rfs are at each appearance each independently a perfluoro(poly)ether group represented by the formula:
—(CfF2f)—(OCF2)a1—(OCF2CF2)a21—(OCF(CF3))a2′—(OCF2CF2CF2)a31—(OCF2CF(CF3))a3′—(OCF(CF3)CF2)a3″—(OCF2CF2CF2CF2)a4—
wherein, f is an integer of 1 or more and 4 or less, a sum of a2l and a2′ equals to a2, a sum of a3l, a3′ and a3″ equals to a3, a1 is an integer of 0 or more and 50 or less, a2 is an integer of 0 or more and 50 or less, a3 is an integer of 0 or more and 30 or less, a4 is an integer of 0 or more and 30 or less, a sum of a1, a2, a3 and a4 is 5 or more and 200 or less, and the order of existence of each repeating unit is arbitrary in the formula,
g is an integer of 0 or more and 5 or less,
j and k are each 1,
h and i are each independently 0 or 1 at each appearance,
X1s are each independently a urethane bond or an amide bond at each appearance,
X1's are each independently a divalent alkylene group having amide bonds at both ends at each appearance,
X2s and X2's are each independently a divalent alkylene group at each appearance,
R3s are each independently an alkyl group having 1 to 4 carbon atoms or an alkoxyalkyl group at each appearance, and
R4s are each independently a hydrogen atom or an alkyl group having 1 to 22 carbon atoms at each appearance.

### Claim 4 (depends on 1)

The curable composition according to claim 1, wherein
Component (A) is a compound represented by any of the following formulae:
wherein:
PFPE1s are at each appearance each independently a group represented by the formula:
—(CfF2f)—(OCF2)a1—(OC2F4)a2—(OC3F6)a3—(OC4F8)a4—(OC5F10)a5—(OC6F12)a6—(OC7F14)a7—(OC8F16)a8—
wherein, f is an integer of 1 to 10, a1 and a2 are each independently an integer of 1 or more and 200 or less, a3, a4, a5, a6, a7 and a8 are each independently an integer of 0 or more and 30 or less, a sum of a1, a2, a3, a4, a5, a6, a7 and a8 is an integer of 5 or more and 200 or less, the unit represented by (CfF2f) is located at the left end of the group, and the order of existence of each repeating unit enclosed in parentheses with the subscript a1, a2, a3, a4, a5, a6, a7 or a8 is arbitrary in the formula,
R3s are each independently an alkyl group having 1 to 4 carbon atoms at each appearance,
ds are each independently an integer of 1 to 4 at each appearance,
and e is an integer of 1 to 4.

### Claim 5 (depends on 1)

The curable composition according to claim 1, wherein
Component (B) contains a compound represented by the following formula:
R1nSi(OR2)4-n
wherein,
R1s are each independently a substituted or unsubstituted monovalent hydrocarbon group at each appearance,
R2s are each independently a hydrogen atom or a monovalent organic group at each appearance, and
n is 0, 1 or 2,
or a partially hydrolyzed condensate thereof.

### Claim 6 (depends on 5)

The curable composition according to claim 5, wherein
Component (B) further contains a compound represented by the following formula (B2):
wherein,
Rg3s each independently represent a hydrogen atom or a monovalent organic group at each appearance,
Rg4 is a substituted or unsubstituted monovalent hydrocarbon group,
Rg6s are each independently Rg8-Rg7—at each appearance,
Rg7s are each independently an alkylene group having 1 to 10 carbon atoms, or a group having 1 to 10 carbon atoms and containing a nitrogen atom or an oxygen atom in a main chain at each appearance,
Rg8 s are each independently a primary amino group, an epoxy group, a (meth)acryloyl group, a (meth)acryloxy group, a mercapto group or an isocyanato group at each appearance,
ε4 is 2 or 3,
ε5 is 0 or 1, and
ε6 is 1 or 2, provided that a sum of ε4, ε5 and ε6 is 4,
or a partially hydrolyzed condensate thereof.

### Claim 7 (depends on 1)

The curable composition according to claim 1, wherein the linking group between the alkoxysilyl groups of Component (D) is a group containing a nitrogen atom and/or a carbonyl group.

### Claim 8 (depends on 7)

The curable composition according to claim 7, wherein the linking group between the alkoxysilyl groups of Component (D) is a group further containing an —O— group, an alkenylene group and/or an alkylene group.

### Claim 9 (depends on 1)

The curable composition according to claim 1, wherein Component (D) is selected from the group consisting of an alkoxysilyl group-containing isocyanurate compound, an alkoxysilyl group-containing carbasilatrane compound, an alkoxysilyl group-containing fumaric acid ester compound and an alkoxysilyl group-containing amine compound.

### Claim 10 (depends on 2)

The curable composition according to claim 2, wherein the linking group between the alkoxysilyl groups of Component (D) is a group containing a nitrogen atom and/or a carbonyl group.

### Claim 11 (depends on 10)

The curable composition according to claim 10, wherein the linking group between the alkoxysilyl groups of Component (D) is a group further containing an —O— group, an alkenylene group and/or an alkylene group.

### Claim 12 (depends on 2)

The curable composition according to claim 2, wherein Component (D) is selected from the group consisting of an alkoxysilyl group-containing isocyanurate compound, an alkoxysilyl group-containing carbasilatrane compound, an alkoxysilyl group-containing fumaric acid ester compound and an alkoxysilyl group-containing amine compound.

### Claim 13 (depends on 3)

The curable composition according to claim 3, wherein the linking group between the alkoxysilyl groups of Component (D) is a group containing a nitrogen atom and/or a carbonyl group.

### Claim 14 (depends on 13)

The curable composition according to claim 13, wherein the linking group between the alkoxysilyl groups of Component (D) is a group further containing an —O— group, an alkenylene group and/or an alkylene group.

### Claim 15 (depends on 3)

The curable composition according to claim 3, wherein Component (D) is selected from the group consisting of an alkoxysilyl group-containing isocyanurate compound, an alkoxysilyl group-containing carbasilatrane compound, an alkoxysilyl group-containing fumaric acid ester compound and an alkoxysilyl group-containing amine compound.

### Claim 16 (depends on 4)

The curable composition according to claim 4, wherein the linking group between the alkoxysilyl groups of Component (D) is a group containing a nitrogen atom and/or a carbonyl group.

### Claim 17 (depends on 16)

The curable composition according to claim 16, wherein the linking group between the alkoxysilyl groups of Component (D) is a group further containing an —O— group, an alkenylene group and/or an alkylene group.

### Claim 18 (depends on 4)

The curable composition according to claim 4, wherein Component (D) is selected from the group consisting of an alkoxysilyl group-containing isocyanurate compound, an alkoxysilyl group-containing carbasilatrane compound, an alkoxysilyl group-containing fumaric acid ester compound and an alkoxysilyl group-containing amine compound.

### Claim 19 (depends on 2)

The curable composition according to claim 2, wherein
Component (A) is a compound represented by any of the following formulae:
wherein:
PFPE1s are at each appearance each independently a group represented by the formula:
—(CfF2f)—(OCF2)a1—(OC2F4)a2—(OC3F6)a3—(OC4F8)a4—(OC5F10)a5—(OC6F12)a6—(OC7F14)a7—(OC8F16)a8—
wherein, f is an integer of 1 to 10, a1 and a2 are each independently an integer of 1 or more and 200 or less, a3, a4, a5, a6, a7 and a8 are each independently an integer of 0 or more and 30 or less, a sum of a1, a2, a3, a4, a5, a6, a7 and a8 is an integer of 5 or more and 200 or less, the unit represented by (CfF2f) is located at the left end of the group, and the order of existence of each repeating unit enclosed in parentheses with the subscript a1, a2, a3, a4, a5, a6, a7 or a8 is arbitrary in the formula,
R3s are each independently an alkyl group having 1 to 4 carbon atoms at each appearance,
ds are each independently an integer of 1 to 4 at each appearance,
and e is an integer of 1 to 4.

### Claim 20 (depends on 2)

The curable composition according to claim 2, wherein
Component (B) contains a compound represented by the following formula:
R1nSi(OR2)4-n
wherein,
R1s are each independently a substituted or unsubstituted monovalent hydrocarbon group at each appearance,
R2s are each independently a hydrogen atom or a monovalent organic group at each appearance, and
n is 0, 1 or 2,
or a partially hydrolyzed condensate thereof.