# US 2022/0033581 A1 · Diterminally Amine-Modified Perfluoropolyether Compound and Preparation Thereof, and Liquid-Repelling Composition, Cured Product and Coated Substrate Containing the Same

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- Number: US 2022/0033581 A1
- Document ID: US20220033581A1
- Status: Published application
- Kind: A1
- Application number: 17/387,464
- Filed: 2021-07-28
- Published: 2022-02-03
- Earliest claimed: 2020-08-03
- Assignees: Shin-Etsu Chemical Co., Ltd.
- Applicants: Shin-Etsu Chemical Co., Ltd.
- Inventors: Masato KAWAKAMI
- Web page: https://patentgrep.com/patent/US20220033581A1

## CPC

- C08G 65/336: containing silicon
- C08G 65/007: {containing fluorine}
- C08G 65/33396: {having oxygen in addition to nitrogen}
- C09D 5/00: Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced {(electrically insulating plastics, resins or waxes H01B3/30)}; Filling pastes
- C09D 171/00: Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain (based on polyacetals C09D159/00; based on epoxy resins C09D163/00; based on polythioether-ethers C09D181/02; based on polyethersulfones C09D181/06); Coating compositions based on derivatives of such polymers
- C09D 171/02: Polyalkylene oxides
- 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

Diterminally amine-modified perfluoropolyether compounds of the general formula (wherein Rf is a perfluoropolyether group; each R1 is independently an unsubstituted divalent hydrocarbon group of 1 to 10 carbon atoms; R2, R3 and R4 are each independently substituted or unsubstituted monovalent hydrocarbon groups of 1 to 10 carbon atoms; each R5 is independently an unsubstituted divalent hydrocarbon group of 1 to 10 carbon atoms; each R6 is independently a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group of 1 to 50 carbon atoms which may include at least one oxygen, nitrogen, sulfur or silicon atom; each occurrence of ‘m’ is independently 0, 1 or 2; and each occurrence of ‘n’ is independently an integer from 0 to 8) are provided. Such compounds have a good solubility in solvents and reactive resins.

## Claims

### Claim 1

A diterminally amine-modified perfluoropolyether compound of general formula (1) below
(wherein Rf is a perfluoropolyether group; each R1 is independently an unsubstituted divalent hydrocarbon group of 1 to 10 carbon atoms; R2, R3 and R4 are each independently substituted or unsubstituted monovalent hydrocarbon groups of 1 to 10 carbon atoms; each R5 is independently an unsubstituted divalent hydrocarbon group of 1 to 10 carbon atoms; each R6 is independently a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group of 1 to 50 carbon atoms which may include at least one oxygen, nitrogen, sulfur or silicon atom; each occurrence of ‘m’ is independently 0, 1 or 2; and each occurrence of ‘n’ is independently an integer from 0 to 8).

### Claim 2 (depends on 1)

The perfluoropolyether compound of claim 1, wherein each R1 is independently a substituent of formula (5) or (6) below.

### Claim 3 (depends on 1)

The perfluoropolyether compound of claim 1, wherein Rf is a divalent group of any one of general formulas (7) to (10) below
(wherein ‘a’ and ‘b’ are each independently an integer from 1 to 50, and ‘c’ is an integer from 1 to 150).

### Claim 4 (depends on 1)

A method for preparing the diterminally amine-modified perfluoropolyether compound of claim 1, comprising the step of reacting a diterminally silanol-modified perfluoropolyether compound of general formula (2) below
(wherein Rf, R1, R2 and n are as defined above) with a cyclic silazane structure-containing organoxysilane compound of general formula (3) below
(wherein R3 to R6 and m are as defined above).

### Claim 5 (depends on 1)

A method for preparing the diterminally amine-modified perfluoropolyether compound of claim 1, comprising the step of reacting a diterminally silanol-modified perfluoropolyether compound of general formula (2) below
(wherein Rf, R1, R2 and n are as defined above) with an amino group-containing organoxysilane compound of general formula (4) below
(wherein R3 to R6 and m are as defined above).

### Claim 6 (depends on 1)

A liquid-repelling composition comprising the diterminally amine-modified perfluoropolyether compound of claim 1.

### Claim 7 (depends on 6)

A cured product obtained by curing the liquid-repelling composition of claim 6.

### Claim 8 (depends on 6)

A coated substrate comprising a substrate and a coating film formed thereon, wherein the coating film is formed with the liquid-repelling composition of claim 6.