# US 2019/0169341 A1 · Binder compositions and methods for making and using same

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- Number: US 2019/0169341 A1
- Document ID: US20190169341A1
- Status: Published application
- Kind: A1
- Application number: 16/273,305
- Filed: 2019-02-12
- Published: 2019-06-06
- Earliest claimed: 2013-03-14
- Assignees: Georgia-Pacific Chemicals LLC
- Applicants: Georgia-Pacific Chemicals LLC
- Inventors: Bobby L. Williamson; Adam K. Sniady; Brian L. Swift; Ramji Srinivasan; Feng Jing; Cornel Hagiopol
- Web page: https://patentgrep.com/patent/US20190169341A1

## CPC

- C08F 222/12: of phenols or saturated alcohols {(C08F222/1006 takes precedence)}
- B27N 3/002: {characterised by the type of binder (compositions of macromolecular compounds C08L)}
- C08F 122/38: Amides
- C09D 135/02: Homopolymers or copolymers of esters (C09D135/06, C09D135/08 take precedence)
- C09J 167/06: Unsaturated polyesters having carbon-to-carbon unsaturation
- C08F 222/1061: {of alcohol terminated polyesters or polycarbonates, e.g. polyester (meth)acrylates}
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- B27N: MANUFACTURE BY DRY PROCESSES OF ARTICLES, WITH OR WITHOUT ORGANIC BINDING AGENTS, MADE FROM PARTICLES OR FIBRES CONSISTING OF WOOD OR OTHER LIGNOCELLULOSIC OR LIKE ORGANIC MATERIAL (containing cementitious material B28B; shaping of substances in a plastic state B29C; fibreboards made from fibrous suspensions D21J; drying F26B17/00)
- 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)
- 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)

## Abstract

Binder compositions and methods for making and using same are provided. In at least one specific embodiment, the binder composition can include at least one unsaturated compound having two or more unsaturated carbon-carbon bonds and at least one free radical precursor. At least one of the unsaturated carbon-carbon bonds can be a pi-bond that is not conjugated with an aromatic moiety and can be capable of free radical addition. The free radical precursor can be present in an amount of about 7 wt % to about 99 wt %, based on the weight of the one or more unsaturated compounds.

## Claims

### Claim 1

A binder composition, comprising:
an unsaturated compound comprising a reaction product of an unsaturated epoxide and an unsaturated polyester prepolymer, wherein the unsaturated polyester prepolymer comprises a reaction product of a polyol and an acid anhydride, wherein:
the unsaturated epoxide comprises allyl glycidyl ether, 3,4-epoxy-1-butene, 1,2-epoxy-5-hexene, or a mixture thereof,
the polyol comprises ethylene glycol, diethylene glycol, triethylene glycol, glycerol, polyglycerol, pentaerythritol, trimethylolpropane, diethanolamine, triethanolamine, ethyl diethanolamine, methyl diethanolamine, sorbitol, glucose, fructose, sucrose, starch, dextrin, maltodextrin, polyvinyl alcohol, hydroxyethylcellulose, 1,4-cyclohexanediol, 2-butene-1,4-diol, hydroxyl-terminated polybutadiene, or a mixture thereof, and
the acid anhydride comprises phthalic anhydride, mellitic anhydride, pyromellitic anhydride, maleic anhydride, or a mixture thereof; and
a free radical precursor comprising an oxidant and a catalyst.

### Claim 2 (depends on 1)

The binder composition of claim 1, wherein the oxidant comprises hydrogen peroxide, an alkali metal salt of percarbonate, an alkali metal salt of perborate, an alkali metal salt of peroxysulfate, an alkali metal salt of peroxyphosphate, an alkali metal salt of peroxysilicate, t-butyl peroxide, benzoyl peroxide, peroxy carboxylic acids, peracetic acid, perbenzoic acid, t-butyl hydroperoxide, an alkali metal chlorite, an alkali metal hypochlorite, chlorine dioxide, a chloro sodium salt of cyanuric acid, dimethyloxirane, or a mixture thereof.

### Claim 3 (depends on 1)

The binder composition of claim 1, wherein the oxidant comprises an inorganic oxidant.

### Claim 4 (depends on 1)

The binder composition of claim 1, wherein a weight ratio of the free radical precursor to the unsaturated compound is about 0.05:1 to about 40:1.

### Claim 5 (depends on 1)

The binder composition of claim 1, wherein the catalyst comprises an iron containing catalyst comprising potassium ferricyanide, iron (II) sulfate, iron (III) sulfate, an iron complex of ethylenediamine tetraacetic acid, an iron complex of ethylenediamine-N,N′-disuccinic acid, an iron complex of diethylenetriamine pentaacetic acid, an iron complex of ethyleneglycol bis(2-aminoethylether)-N,N,N′,N′-tetraacetic acid, an iron complex of trans-1,2-diaminocyclohexanetetraacetic acid, or a mixture thereof.

### Claim 6 (depends on 1)

The binder composition of claim 1, wherein a weight ratio of the free radical precursor to the unsaturated compound is at least 0.23:1 to about 40:1.

### Claim 7 (depends on 6)

The binder composition of claim 6, wherein the oxidant comprises hydrogen peroxide and the catalyst comprises an iron containing catalyst.

### Claim 8 (depends on 1)

The binder composition of claim 1, wherein:
the unsaturated epoxide comprises allyl glycidyl ether,
the polyol comprises polyglycerol,
the acid anhydride comprises maleic anhydride,
the oxidant comprises hydrogen peroxide, and
the catalyst comprises an iron containing catalyst.

### Claim 9 (depends on 1)

The binder composition of claim 1, wherein:
the unsaturated epoxide comprises allyl glycidyl ether,
the polyol comprises pentaerythritol,
the acid anhydride comprises maleic anhydride,
the oxidant comprises hydrogen peroxide, and
the catalyst comprises an iron containing catalyst.

### Claim 10 (depends on 1)

The binder composition of claim 1, wherein:
the unsaturated epoxide comprises allyl glycidyl ether,
the polyol comprises sorbitol,
the acid anhydride comprises maleic anhydride,
the oxidant comprises hydrogen peroxide, and
the catalyst comprises an iron containing catalyst.

### Claim 11 (depends on 1)

The binder composition of claim 1, further comprising a second unsaturated compound comprising dicyclopentadiene, ethylene glycol diacrylate, ethylene glycol dimethacrylate, diethylene glycol diacrylate, diethylene glycol dimethacrylate, poly(ethylene glycol) diacrylate, poly(ethylene glycol) dimethacrylate, trimethylolpropane triacrylate, pentaerythritol tetraacrylate, pentaerythritol triacrylate, polyacrylate starch, or a mixture thereof.

### Claim 12

A process for making a binder composition, comprising:
reacting a polyol and an acid anhydride to produce an unsaturated polyester prepolymer, wherein:
the polyol comprises ethylene glycol, diethylene glycol, triethylene glycol, glycerol, polyglycerol, pentaerythritol, trimethylolpropane, diethanolamine, triethanolamine, ethyl diethanolamine, methyl diethanolamine, sorbitol, glucose, fructose, sucrose, starch, dextrin, maltodextrin, polyvinyl alcohol, hydroxyethylcellulose, 1,4-cyclohexanediol, 2-butene-1,4-diol, hydroxyl-terminated polybutadiene, or a mixture thereof, and
the acid anhydride comprises phthalic anhydride, mellitic anhydride, pyromellitic anhydride, maleic anhydride, or a mixture thereof;
reacting the unsaturated polyester prepolymer and an unsaturated epoxide to produce an unsaturated compound, wherein the unsaturated epoxide comprises allyl glycidyl ether, 3,4-epoxy-1-butene, 1,2-epoxy-5-hexene, or a mixture thereof; and
mixing the unsaturated compound with a free radical precursor comprising an oxidant and a catalyst to produce the binder composition.

### Claim 13 (depends on 12)

The process of claim 12, wherein:
the unsaturated epoxide comprises allyl glycidyl ether,
the polyol comprises polyglycerol, pentaerythritol, sorbitol, or a mixture thereof,
the acid anhydride comprises maleic anhydride,
the oxidant comprises hydrogen peroxide, and
the catalyst comprises an iron containing catalyst.

### Claim 14 (depends on 13)

The process of claim 13, wherein a weight ratio of the free radical precursor to the unsaturated compound is at least 0.23:1 to about 40:1, and wherein the oxidant comprises hydrogen peroxide and the catalyst comprises an iron containing catalyst.

### Claim 15 (depends on 14)

The process of claim 14, wherein the iron containing catalyst comprises potassium ferricyanide, iron (II) sulfate, iron (III) sulfate, an iron complex of ethylenediamine tetraacetic acid, an iron complex of ethylenediamine-N,N′-disuccinic acid, an iron complex of diethylenetriamine pentaacetic acid, an iron complex of ethyleneglycol bis(2-aminoethylether)-N,N,N′,N′-tetraacetic acid, an iron complex of trans-1,2-diaminocyclohexanetetraacetic acid, or a mixture thereof.

### Claim 16

A process for making a composite product, comprising:
combining a plurality of lignocellulose substrates, an unsaturated compound, and a free radical precursor to produce a resinated furnish, wherein:
the unsaturated compound comprises a reaction product of an unsaturated epoxide and an unsaturated polyester prepolymer, wherein the unsaturated polyester prepolymer comprises a reaction product of a polyol and an acid anhydride, wherein:
the unsaturated epoxide comprises allyl glycidyl ether, 3,4-epoxy-1-butene, 1,2-epoxy-5-hexene, or a mixture thereof,
the polyol comprises ethylene glycol, diethylene glycol, triethylene glycol, glycerol, polyglycerol, pentaerythritol, trimethylolpropane, diethanolamine, triethanolamine, ethyl diethanolamine, methyl diethanolamine, sorbitol, glucose, fructose, sucrose, starch, dextrin, maltodextrin, polyvinyl alcohol, hydroxyethylcellulose, 1,4-cyclohexanediol, 2-butene-1,4-diol, hydroxyl-terminated polybutadiene, or a mixture thereof, and
the acid anhydride comprises phthalic anhydride, mellitic anhydride, pyromellitic anhydride, maleic anhydride, or a mixture thereof; and
the free radical precursor comprises an oxidant and a catalyst; and
heating the resinated furnish to a temperature of about 60° C. to about 300° C. to produce the composite product.

### Claim 17 (depends on 16)

The process of claim 16, wherein the resinated furnish is compressed in a press under a pressure of about 0.5 MPa to about 11 MPa when the resinated furnish is heated.

### Claim 18 (depends on 17)

The process of claim 17, wherein the press is a closed press.

### Claim 19 (depends on 17)

The process of claim 17, wherein the press is an open press.

### Claim 20 (depends on 17)

The process of claim 17, wherein the composite product comprises particleboard, fiberboard, plywood, oriented strand board, parallel strand lumber, or laminated veneer lumber.