# US 9,040,650 B2 · Resins of the phenoplast type obtained from phenolic compounds and from macromolecular hardeners bearing aldehyde functions

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- Number: US 9,040,650 B2
- Document ID: US9040650B2
- Status: Granted
- Kind: B2
- Application number: 13/510,624
- Filed: 2010-11-19
- Published: 2012-11-01
- Granted: 2015-05-26
- Earliest claimed: 2009-11-20
- Assignees: Centre National de la Recherche Scientifique (CNRS); Universite Montpellier 2 Sciences Et Techniques; Ecole Nationale Superieure De Chimie De Montpellier
- Applicants: Sylvain Caillol; Bernard Boutevin; Ghislain David; Carine Burguiere
- Inventors: Sylvain Caillol; Bernard Boutevin; Ghislain David; Carine Burguiere
- Web page: https://patentgrep.com/patent/US9040650B2

## CPC

- C08G 8/04: of aldehydes
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

A method for preparing a formaldehyde-free phenolic plastic resin, includes a step of preparing a hardener via careful oxidation of a polyol and a step of reacting the hardener with phenolic compounds.

## Claims

### Claim 1

A method for preparing a phenoplast resin without using any formaldehyde, comprising:
preparing a macromolecular hardener bearing aldehyde functions by controlled oxidation of the primary alcohols of a polyol bearing primary alcohols, and
reacting phenolic compounds with said hardener, wherein said phenolic compounds are selected from the group consisting of acid-phenols, coumarins, naphthoquinones, stilbenoids, flavonoids, isoflavonoids, anthocyans, lignans, lignins, condensed tannins and hydrolyzable tannins.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the polyol is a natural polyol.

### Claim 3 (depends on 1)

The method according to claim 1, wherein the polyol is a synthetic polyol.

### Claim 4 (depends on 1)

The method according to claim 1, wherein the polyol has from 2 to 20 primary hydroxy groups.

### Claim 5 (depends on 1)

The method according to claim 1, wherein the polyol is selected from the group consisting of poly(allyl alcohol), poly (hydroxy ethyl acrylate) and polyethers.

### Claim 6 (depends on 1)

The method according to claim 1, wherein the phenolic compounds are of natural origin.

### Claim 7 (depends on 1)

The method according to claim 1, wherein the controlled oxidation of the primary alcohol of the polyol is carried out in water at 0° C. and in the presence of an oxidizer.

### Claim 8 (depends on 7)

The method according to claim 7, wherein the oxidizer is (2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl (TEMPO), accompanied by a hypohalite.

### Claim 9 (depends on 1)

A phenoplast resin obtained by the method according to claim 1.

### Claim 10 (depends on 1)

The method according to claim 1, wherein the phenolic compound is selected from the group consisting of: p-hydroxybenzoic acid; gallic acid; p-coumaric acid; umbelliferone; juglone; trans-resveratrol; kaempferol; daidzein; delphinidol; enterodiol; procyanidin; and gallotannins.

### Claim 11

A method for preparing a phenoplast resin without using any formaldehyde, comprising:
preparing a macromolecular hardener bearing aldehyde functions by controlled oxidation of the primary alcohols of a polyol, and
reacting phenolic compounds with said hardener, wherein said phenolic compounds are selected from the group consisting of acid-phenols, coumarins, naphthoquinones, stilbenoids, flavonoids, isoflavonoids, anthocyans, and lignans.

### Claim 12

A method for preparing a phenoplast resin without using any formaldehyde, comprising:
preparing a macromolecular hardener bearing aldehyde functions by controlled oxidation of the primary alcohols of a polyol, and
reacting phenolic compounds with said hardener, wherein said phenolic compounds are selected from the group consisting of stilbenoids, flavonoids, and isoflavonoids.

### Claim 13 (depends on 12)

The method according to claim 12, wherein the polyol is poly(hydroxyethylacrylate) that has been oxidized to contain the aldehyde functions.