# US 9,040,638 B2 · Use of hydroxycarboxylic acid oligomers as adhesives, manufacturing method and hydroxycarboxylic acid oligomers obtained

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- Number: US 9,040,638 B2
- Document ID: US9040638B2
- Status: Granted
- Kind: B2
- Application number: 13/503,882
- Filed: 2010-10-27
- Published: 2012-08-30
- Granted: 2015-05-26
- Earliest claimed: 2009-10-30
- Assignees: Valagro Carbone Renouvelable Poitou-Charentes
- Applicants: Antoine Piccirilli; Cedric Dever
- Inventors: Antoine Piccirilli; Cedric Dever
- Web page: https://patentgrep.com/patent/US9040638B2

## CPC

- C09J 167/04: Polyesters derived from hydroxycarboxylic acids, e.g. lactones (C09J167/06 takes precedence)
- C08G 18/4283: {Hydroxycarboxylic acid or ester}
- C08G 63/06: derived from hydroxycarboxylic acids
- C09J 175/06: from polyesters
- C08G 2230/00: Compositions for preparing biodegradable polymers
- 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)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

Disclosed is a method of using at least one functionalized hydroxycarboxylic acid oligomer as an adhesive for bonding materials. Also described is a process for manufacturing functionalized hydroxycarboxylic acid oligomers including at least one stage for polycondenzation of a hydroxycarboxylic acid and a functional agent, as well as functionalized hydroxycarboxylic acid oligomers that can be obtained and the adhesive compositions that include them.

## Claims

### Claim 1

A method for bonding materials, comprising steps of:
providing an adhesive comprising at least one functionalized hydroxycarboxylic acid oligomer that is obtained by at least one stage for polycondensation of a hydroxycarboxylic acid in the presence of a functional agent that is derived from an oil or a fat of natural origin; and
suitably applying the adhesive to the materials to be bonded.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the materials to be bonded are lignocellulosic materials.

### Claim 3 (depends on 1)

The method according to claim 1, wherein the functionalized hydroxycarboxylic acid oligomer is a hydroxycarboxylic acid oligomer with at least one acid or hydroxyl group.

### Claim 4 (depends on 1)

The method according to claim 1, wherein the functionalized hydroxycarboxylic acid oligomer is an esterified hydroxycarboxylic acid oligomer.

### Claim 5 (depends on 1)

The method according to claim 1, wherein the adhesive further comprises at least one polyisocyanate.

### Claim 6

A process for manufacturing a functionalized hydroxycarboxylic acid oligomer, comprising a step of carrying out polycondensation of a hydroxycarboxylic acid in the presence of a functional agent that is derived from an oil or a fat of natural origin.

### Claim 7 (depends on 6)

The process according to claim 6, wherein the functional agent is an acid or hydroxyl functional agent.

### Claim 8 (depends on 6)

The process according to claim 6, wherein the polycondensation is carried out in the presence of a catalyst.

### Claim 9 (depends on 6)

The process according to claim 6, wherein the polycondensation is carried out at a pressure of between 1 and 900 mbar and at a temperature of between 70 and 140° C.

### Claim 10 (depends on 6)

The process according to claim 6, wherein the polycondensation is carried out by direct dehydration in the presence of a hydroxyl-containing compound or acid.

### Claim 11 (depends on 6)

The process according to claim 6, wherein the molar ratio of functional agent to hydroxycarboxylic acid is between 0.01 and 50%.

### Claim 12 (depends on 2)

The method according to claim 2, wherein the functionalized hydroxycarboxylic acid oligomer is a hydroxycarboxylic acid oligomer with at least one acid or hydroxyl group.

### Claim 13 (depends on 1)

The method according to claim 1, wherein the functionalized hydroxycarboxylic acid oligomer is represented by the formula:
R-(-(-M-R2)n)x
wherein:
R represents a carbon-containing chain derived from said functional agent,
R2 represents a reactive group,
x is an integer greater than or equal to 1,
M represents a hydroxycarboxylic acid, and
n is an integer greater than 1 and less than or equal to 1,000.

### Claim 14 (depends on 13)

The method according to claim 13, wherein R2 is OH or COOH.

### Claim 15 (depends on 13)

The method according to claim 13, wherein x is between 1 and 10.

### Claim 16 (depends on 1)

The method according to claim 1, wherein the adhesive comprises between 10 and 90% of the functionalized hydroxycarboxylic oligomer.

### Claim 17 (depends on 1)

The method according to claim 1, wherein the functional agent is a fatty acid.

### Claim 18 (depends on 1)

The method according to claim 1, wherein the oligomer has a degree of polymerization greater than 1 and less than or equal to 1000.

### Claim 19 (depends on 1)

The method according to claim 1, wherein the functional agent is derived from a C12-C32 fatty acid.