# US 2020/0399512 A1 · Adhesive and its preparation and application

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- Number: US 2020/0399512 A1
- Document ID: US20200399512A1
- Status: Published application
- Kind: A1
- Application number: 16/903,466
- Filed: 2020-06-17
- Published: 2020-12-24
- Earliest claimed: 2019-06-19
- Assignees: Covestro Intellectual Property GmbH & Co. KG
- Applicants: Covestro Intellectual Property GmbH & Co. KG
- Inventors: Chenxi Zhang
- Web page: https://patentgrep.com/patent/US20200399512A1

## CPC

- C09J 175/08: from polyethers
- B29C 65/485: {Multi-component adhesives, i.e. chemically curing as a result of the mixing of said multi-components}
- B29C 66/7212: {characterised by the composition of the fibres}
- B32B 7/12: using interposed adhesives or interposed materials with bonding properties
- B32B 17/04: bonded with or embedded in a plastic substance
- C08F 283/006: {on to polymers provided for in C08G18/00 (C08F283/004 takes precedence)}
- C08G 18/12: using two or more compounds having active hydrogen in the first polymerisation step
- C08G 18/166: {Catalysts not provided for in the groups C08G18/18 - C08G18/26}
- C08G 18/3215: {containing aromatic groups or benzoquinone groups}
- C08G 18/348: {Hydroxycarboxylic acids}
- C08G 18/48: Polyethers
- C08G 18/4829: {Polyethers containing at least three hydroxy groups (C08G18/4833 - C08G18/5096 take precedence)}
- C08G 18/4883: {containing cyclic groups having at least one oxygen atom in the ring}
- C08G 18/6229: {Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols}
- C08G 18/672: {Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen}
- C08G 18/7657: {containing two or more aromatic rings}
- C08G 18/7664: {containing alkylene polyphenyl groups}
- C08J 5/043: {with glass fibres}
- C08K 5/14: Peroxides
- C08K 5/5425: containing at least one C=C bond
- C08K 7/14: Glass
- C09J 7/35: Heat-activated
- C09J 11/06: organic
- C09J 175/14: Polyurethanes having carbon-to-carbon unsaturated bonds
- C09J 175/16: having terminal carbon-to-carbon unsaturated bonds
- B29L 2031/082: {Blades, e.g. for helicopters}
- C08G 2190/00: Compositions for sealing or packing joints
- C09J 2475/00: Presence of polyurethane
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)
- B29C: SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING (making preforms B29B11/00; making laminated products by combining previously unconnected layers which become one product whose layers will remain together B32B37/00 - B32B41/00)
- B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- 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
- 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)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- B29L: INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES

## Abstract

The present invention relates to an adhesive, a preparation method and application thereof, particularly the application for bonding glass fiber composites, and a bonded article obtained by using the adhesive. The adhesive comprises: a polyisocyanate having an isocyanate functionality of not less than 2; an epoxy-modified polyether polyol; a hydroxyl-containing acrylate; a redox catalyst; a silane coupling agent; optionally a polyol containing bisphenol A structure; and optionally a polymer polyol different from the epoxy-modified polyether polyol. The adhesive according to the present invention has the advantages of being insensitive to moisture, good bonding properties and a long pot life.

## Claims

### Claim 1

An adhesive, comprising the following components:
a. a polyisocyanate having an isocyanate functionality of not less than 2;
b. an epoxy-modified polyether polyol;
c. a hydroxyl-containing acrylate;
d. a redox catalyst;
e. a silane coupling agent;
f. optionally a polyol containing bisphenol A structure; and
g. optionally a polymer polyol different from the epoxy-modified polyether polyol;
wherein the hydroxyl-containing acrylate conforms to the following general formula:
wherein R1 is hydrogen or methyl or —CH2—OH and R2 is a saturated or unsaturated, linear or branched, aliphatic or cycloaliphatic divalent residue, having up to 18 carbon atoms, wherein said saturated or unsaturated, linear or branched, aliphatic or cycloaliphatic divalent residue, having up to 18 carbon atoms, can optionally comprise oxygen atoms and/or hydroxyl groups;
and wherein the redox catalyst is one or more of the following: a peroxide, a persulfide, a peroxycarbonate, a peroxyboric acid, and an azide; the epoxy-modified polyether polyol is present in an amount of 50 wt % to 70 wt %, and the hydroxyl-containing acrylate is present in an amount of 25 wt % to 50 wt %, based on a sum of the weights of components b, c, f and gas 100 wt %.

### Claim 2 (depends on 1)

The adhesive according to claim 1, wherein the hydroxyl-containing acrylate is one or more of the following: a hydroxyl-containing acrylic acid or methacrylic acid derivative, 3-hydroxypropyl ester, 2-hydroxypropyl ester, hydroxybutyl ester, polyvinyl alcohol monohydroxy ester, methyl hydroxy acrylate hydroxyalkyl ester, and polypropylene glycol monohydroxy ester.

### Claim 3 (depends on 1)

The adhesive according to claim 1, wherein the hydroxyl-containing acrylate is present in an amount of 30 wt % to 50 wt %, based on the sum of the weights of the components b, c, f and g as 100 wt %.

### Claim 4 (depends on 1)

The adhesive according to claim 1, wherein the redox catalyst is one or more of the following: benzoyl peroxide, tert-butyl peroxybenzoate, methyl ethyl ketone peroxide, and dicumyl peroxide.

### Claim 5 (depends on 1)

The adhesive according to claim 1, wherein the silane coupling agent conforms to the general formula XSi(OR4)3, wherein X is one or more of the following: vinyl, γ-methacryloxypropyl, and γ-isocyanatopropyl; R4 is one or more of the following: methyl and ethyl.

### Claim 6 (depends on 1)

The adhesive according to claim 1, wherein the silane coupling agent is present in an amount of 0.5 wt % to 1.5 wt %, based on the a total amount of the adhesive as 100 wt %.

### Claim 7 (depends on 1)

The adhesive according to claim 1, wherein a weight ratio of a sum of weights of the epoxy-modified polyether polyol and the optional polyether polyol different from the epoxy-modified polyether polyol to that of the polyisocyanate is from 0.4 to 1.2.

### Claim 8 (depends on 1)

A method for producing an adhesive according to claim 1, comprising mixing in any manner the polyisocyanate having an isocyanate functionality of not less than 2 (a), the epoxy-modified polyether polyol (b), the hydroxyl-containing acrylate (c), the redox catalyst (d), the silane coupling agent (e), the optional polyol containing bisphenol A structure (f) and the optional polymer polyol different from the epoxy-modified polyether polyol (g) to obtain the adhesive;
wherein the hydroxyl-containing acrylate conforms to the following general formula:
wherein R1 is hydrogen or methyl or —CH2—OH and R2 is a saturated or unsaturated, linear or branched, aliphatic or cycloaliphatic divalent residue, having up to 18 carbon atoms, wherein said saturated or unsaturated, linear or branched, aliphatic or cycloaliphatic divalent residue, having up to 18 carbon atoms, can optionally comprise oxygen atoms and/or hydroxyl groups;
and wherein the redox catalyst is one or more of the following: a peroxide, a persulfide, a peroxycarbonate, a peroxyboric acid, and an azide; the epoxy-modified polyether polyol is present in an amount of 50 wt % to 70 wt %, and the hydroxyl-containing acrylate has is present in an amount of 25 wt % to 50 wt %, based on the sum of the weights of the components b, c, f and g as 100 wt %.

### Claim 9

(canceled)

### Claim 10

(canceled)

### Claim 11 (depends on 1)

A bonded article comprising an adhesive according to claim 1.

### Claim 12 (depends on 1)

A method for producing a bonded article, comprising:
i. injecting an adhesive according to claim 1 into a cavity of a part to be bonded or coating it onto a substrate to be bonded; and
ii. heating and curing the adhesive to obtain the bonded article.

### Claim 13 (depends on 12)

The method according to claim 12, wherein the cavity of the part to be bonded or the substrate to be bonded is made of a glass fiber composite.

### Claim 14 (depends on 12)

The method according to claim 12, wherein the bonded article is a fan blade or a sleeper.

### Claim 15 (depends on 12)

The method according to claim 12, wherein the adhesive has a thickness of from 5 mm to 20 mm after heating and curing.