# US 2021/0340416 A1 · Two-component polyurethane adhesive composition and bonding method thereof

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- Number: US 2021/0340416 A1
- Document ID: US20210340416A1
- Status: Published application
- Kind: A1
- Application number: 16/753,257
- Filed: 2019-12-04
- Published: 2021-11-04
- Earliest claimed: 2019-12-04
- Assignees: Hangzhou Zhijiang New Material Co., Ltd; Hangzhou Zhijiang Silicone Chemicals Co., Ltd.
- Applicants: Hangzhou Zhijiang New Material Co., Ltd; Hangzhou Zhijiang Silicone Chemicals Co., Ltd.
- Inventors: Hui SUN; Xiaole TAO; Yunlong LI; Yongfu HE
- Web page: https://patentgrep.com/patent/US20210340416A1

## CPC

- C08G 18/2063: {having two nitrogen atoms in the condensed ring system}
- C09J 175/08: from polyethers
- C08G 18/10: Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G 18/12: using two or more compounds having active hydrogen in the first polymerisation step
- C08G 18/165: {covered by C08G18/18 and C08G18/24}
- C08G 18/246: {containing also tin-carbon bonds}
- C08G 18/3206: {aliphatic}
- C08G 18/4018: {Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48}
- C08G 18/4238: {derived from dicarboxylic acids and dialcohols}
- C08G 18/4812: {Mixtures of polyetherdiols with polyetherpolyols having at least three hydroxy groups}
- C08G 18/4825: {Polyethers containing two hydroxy groups (C08G18/4833 - C08G18/5096 take precedence)}
- C08G 18/4829: {Polyethers containing at least three hydroxy groups (C08G18/4833 - C08G18/5096 take precedence)}
- C08G 18/5024: {containing primary and/or secondary amino groups}
- C08G 18/6674: {with compounds of group C08G18/3203}
- C08G 18/73: acyclic
- C08G 18/758: {containing two or more cycloaliphatic rings}
- C08G 18/7671: {containing only one alkylene bisphenyl group}
- C08G 18/792: {formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates}
- C08G 18/797: {containing carbodiimide and/or uretone-imine groups}
- C08G 18/80: Masked polyisocyanates
- C08K 3/013: Fillers, pigments or reinforcing additives
- C09J 5/06: involving heating of the applied adhesive
- C09J 175/06: from polyesters
- C08K 2201/005: Additives being defined by their particle size in general
- C08K 2201/011: Nanostructured additives
- C09J 2203/354: for automotive applications
- C09J 2475/00: Presence of polyurethane
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## Abstract

The present disclosure provides a two-component polyurethane adhesive composition and a bonding method thereof. The two-component polyurethane adhesive composition includes A) a polyol component, and B) an isocyanate component. The polyol component includes A1) one or more polyether polyols, and the isocyanate component includes B1) a first isocyanate prepolymer, wherein the first isocyanate prepolymer is polymerized from isocyanate and a non-linear chain extender. The two-component polyurethane adhesive composition of the present disclosure has good mechanical properties, in particular, high G modulus and high elongation. The polyol component in the two-component polyurethane adhesive composition has good phase stability, and good miscibility with the isocyanate component. The two-component polyurethane adhesive composition of the present disclosure can be used for the production and manufacture of mechanical parts such as automobile components.

## Claims

### Claim 1

A two-component polyurethane adhesive composition, comprising:
A) a polyol component; and
B) an isocyanate component,
wherein
the polyol component comprises A1) one or more polyether polyols;
the isocyanate component comprises B1) a first isocyanate prepolymer; and
the first isocyanate prepolymer is polymerized from isocyanate and a non-linear chain extender.

### Claim 2 (depends on 1)

The two-component polyurethane adhesive composition according to claim 1,
wherein,
the non-linear chain extender has a molecular weight less than 250 daltons; and
the non-linear chain extender is at least one selected from the group consisting of propylene glycol, dipropylene glycol, tripropylene glycol and tetrapropylene glycol.

### Claim 3 (depends on 1)

The two-component polyurethane adhesive composition according to claim 1, wherein the first isocyanate prepolymer is 2-8% of the isocyanate component by weight.

### Claim 4 (depends on 1)

The two-component polyurethane adhesive composition according to claim 1, wherein at least one of the polyol component and the isocyanate component further comprises a crystalline polyester polyol,
wherein
the crystalline polyester polyol is copolymerized from a linear dicarboxylic acid having an even number of carbon atoms and a linear diol having an even number of carbon atoms;
the linear dicarboxylic acid having an even number of carbon atoms is at least one selected from the group consisting of succinic acid, adipic acid, suberic acid and sebacic acid;
the linear diol having an even number of carbon atoms is at least one selected from the group consisting of 1,2-ethanediol, 1,4-butanediol, 1,6-hexanediol and 1,8-octanediol;
the crystalline polyester polyol has a molecular weight of 2000-8000 dalton; and
the crystalline polyester polyol is 0-10% of the polyol component by weight.

### Claim 5 (depends on 1)

The two-component polyurethane adhesive composition according to claim 1, wherein one or more polyether polyols in the polyol component is at least one selected from the group consisting of a homopolymer of propylene oxide, and a copolymer of propylene oxide and ethylene oxide,
wherein
the copolymer of propylene oxide and ethylene oxide is a copolymer of 80-99% propylene oxide and 1-20% ethylene oxide;
an OH equivalent of the one or more polyether polyols is 400-2000 g/mol;
the one or more polyether polyols have a functionality of 2-4; and
the one or more polyether polyols are 30-60% of the polyol component by weight.

### Claim 6 (depends on 1)

The two-component polyurethane adhesive composition according to claim 1, wherein the polyol component further comprises A2) an aliphatic chain extender,
wherein,
the aliphatic chain extender is linear;
the aliphatic chain extender is at least one selected from the group consisting of ethylene glycol, 1,4-butanediol and 1,6-hexanediol;
an OH equivalent of the aliphatic chain extender is not greater than 200 g/mol; and
the aliphatic chain extender is 2-15% of the polyol component by weight.

### Claim 7 (depends on 1)

The two-component polyurethane adhesive composition according to claim 1, wherein the polyol component further comprises A3-1) an organometallic catalyst,
wherein,
the organometallic catalyst is a catalyst having a property of delaying reaction; and
the organometallic catalyst is 0.03-1% of the polyol component by weight.

### Claim 8 (depends on 1)

The two-component polyurethane adhesive composition according to claim 1, wherein the polyol component further comprises A3-2) an amine catalyst,
wherein,
the amine catalyst has a property of delaying reaction; and
the amine catalyst is 0.05-1% of the polyol component by weight.

### Claim 9 (depends on 1)

The two-component polyurethane adhesive composition according to claim 1, wherein the polyol component further comprises A4) a particulate filler,
wherein,
the particulate filler is an inorganic mineral filler;
the particulate filler has a particle size of 100 nm-100 μm; and
the particulate filler is 10-60% of the polyol component by weight.

### Claim 10 (depends on 1)

The two-component polyurethane adhesive composition according to claim 1, wherein the polyol component further comprises A5) polyetheramine,
wherein,
the polyetheramine at least has two primary or secondary amine groups; and
the polyetheramine is 0-5% of the polyol component by weight.

### Claim 11 (depends on 1)

The two-component polyurethane adhesive composition according to claim 1, wherein the polyol component further comprises A6) a crystalline polyester polyol,
wherein,
the crystalline polyester polyol has a molecular weight of 2000-8000 daltons;
the crystalline polyester polyol is copolymerized from a linear dicarboxylic acid having an even number of carbon atoms and a linear diol having an even number of carbon atoms;
the linear dicarboxylic acid having an even number of carbon atoms is at least one selected from the group consisting of succinic acid, adipic acid, suberic acid and sebacic acid;
the linear diol having an even number of carbon atoms is at least one selected from the group consisting of 1,2-ethanediol, 1,4-butanediol, 1,6-hexanediol and 1,8-octanediol; and
the crystalline polyester polyol is 0-10% of the polyol component by weight.

### Claim 12 (depends on 1)

The two-component polyurethane adhesive composition according to claim 1,
wherein
the isocyanate component further comprises B2) a second isocyanate prepolymer;
the second isocyanate prepolymer is polymerized from isocyanate and a crystalline polyester polyol;
crystalline polyester polyol has a molecular weight of 2000-8000 daltons;
the crystalline polyester polyol is copolymerized from a linear dicarboxylic acid having an even number of carbon atoms and a linear diol having an even number of carbon atoms;
the linear dicarboxylic acid having an even number of carbon atoms is at least one selected from the group consisting of succinic acid, adipic acid, suberic acid and sebacic acid;
the linear diol having an even number of carbon atoms is at least one selected from the group consisting of 1,2-ethanediol, 1,4-butanediol, 1,6-hexanediol and 1,8-octanediol; and
the crystalline polyester polyol is 0-10% of the isocyanate component by weight.

### Claim 13 (depends on 1)

The two-component polyurethane adhesive composition according to claim 1, wherein the isocyanate component further comprises B3) a third isocyanate prepolymer, and one or more isocyanate-capped isocyanate prepolymers are polymerized from isocyanate and polyether polyol,
wherein,
an isocyanate equivalent of the third isocyanate prepolymer is greater than 800 g/mol;
the third isocyanate prepolymer has a molecular weight of 2000-6000, and
the third isocyanate prepolymer is 0-60% of the isocyanate component by weight.

### Claim 14 (depends on 1)

The two-component polyurethane adhesive composition according to claim 1, wherein the isocyanate component further comprises B4) a non-prepolymeric isocyanate,
wherein,
an isocyanate equivalent of the non-prepolymeric isocyanate is 125-200 g/mol;
the non-prepolymeric isocyanate is at least one selected from the group consisting of pure MDI, polymeric MDI, and modified MDI incorporated with carbodiimide, uretonimine, isocyanurate, carbamate, allophanate and urea and/or biuret groups; and
the non-prepolymeric isocyanate is 20-50% of the isocyanate component by weight.

### Claim 15 (depends on 1)

The two-component polyurethane adhesive composition according to claim 1,
wherein,
the isocyanate component further comprises B5) an aliphatic isocyanate,
the aliphatic isocyanate comprises 2 isocyanate groups; and
the aliphatic isocyanate is 0-8% of the isocyanate component by weight.

### Claim 16 (depends on 1)

The two-component polyurethane adhesive composition according to claim 1, wherein the isocyanate component further comprises B6) a particulate filler,
wherein,
the particulate filler is an inorganic mineral filler;
the particulate filler has a particle size of 100 nm-100 μm; and
the particulate filler is 10-60% of the isocyanate component by weight.

### Claim 17 (depends on 1)

The two-component polyurethane adhesive composition according to claim 1, wherein the isocyanate component further comprises B7) a plasticizer,
wherein,
the plasticizer is at least one selected from the group consisting of alkyl sulfonate, diisooctyl phthalate (DIOP), diisodecyl phthalate (DIDP), diisononyl phthalate (DINP), tricresyl phosphate and trioctyl phosphate; and
the plasticizer is 0-30% of the isocyanate component by weight.

### Claim 18 (depends on 1)

The two-component polyurethane adhesive composition according to claim 1, wherein the first isocyanate prepolymer, the second isocyanate prepolymer and the one or more isocyanate-capped isocyanate prepolymers are synthesized in situ, or obtained by first separately preparing respective prepolymers and then mixing them.

### Claim 19 (depends on 1)

The two-component polyurethane adhesive composition according to claim 1, wherein a ratio of A) the polyol component to B) the isocyanate component is 1:2 to 10:1.

### Claim 20

(canceled)

### Claim 21

(canceled)

### Claim 22 (depends on 1)

A method for bonding at least two substrates, comprising:
curing, between the at least two substrates, a mixture of A) the polyol component and B) the isocyanate component of the two-component polyurethane adhesive composition according to claim 1.

### Claim 23

(canceled)

### Claim 24

(canceled)