Binder compositions and methods for making and using same

Patent metadata

Field	Value
Publication number	US-10077328-B2
Application number	US-201715810127-A
Country	US
Kind code	B2
Filing date	Nov 12, 2017
Priority date	Mar 14, 2013
Publication date	Sep 18, 2018
Grant date	Sep 18, 2018

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.

First claim

What is claimed is:

1. A binder composition, comprising:
an 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, an unsaturated polyester prepolymer, an unsaturated polyether prepolymer, an unsaturated polyamide prepolymer, an unsaturated polyurethane prepolymer, or a mixture thereof; and
a free radical precursor comprising an inorganic oxidant and a catalyst, wherein a weight ratio of the free radical precursor to the unsaturated compound is at least 0.23:1 to about 40:1.

2. The binder composition of claim 1 , wherein the inorganic oxidant comprises hydrogen peroxide, and wherein the catalyst comprises an iron containing catalyst.

3. The binder composition of claim 1 , wherein the inorganic oxidant comprises hydrogen peroxide, and wherein the catalyst comprises an iron containing catalyst comprising potassium ferricyanide, iron 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.

4. The binder composition of claim 1 , wherein the weight ratio of the free radical precursor to the unsaturated compound is at least 0.23:1 to about 10:1.

5. The binder composition of claim 1 , wherein the weight ratio of the free radical precursor to the unsaturated compound is about 0.3:1 to about 10:1.

6. The binder composition of claim 1 , wherein the unsaturated compound comprises the unsaturated polyester prepolymer, and wherein the unsaturated polyester prepolymer comprises a reaction product of a polyol and a polyacid or a reaction product of a polyol and an anhydride.

7. The binder composition of claim 6 , wherein:
the polyol comprises ethylene glycol, diethylene glycol, triethylene glycol, glycerol, polyglycerol, pentaerythritol, trimethylolpropane, diethanolamine, triethanolamine, ethyl diethanolamine, methyl diethanolamine, sorbitol, a monosaccharide, a disaccharide, dextrin, maltodextrin, polyvinyl alcohol, hydroxyethyl cellulose, 1,4-cyclohexane diol, 2-butene-1,4-diol, hydroxyl-terminated polybutadiene, or a mixture thereof,
the polyacid comprises maleic acid, itaconic acid, fumaric acid, glutaconic acid, citraconic acid, traumatic acid, muconic acid, aconitic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, phthalic acid, isophthalic acid, terephthalic acid, cyclobutanedicarboxylic acid, cyclopentanedicarboxylic acid, cyclohexanedicarboxylic acid, or a mixture thereof, and
the anhydride comprises phthalic anhydride, mellitic anhydride, pyromellitic anhydride, maleic anhydride, or a mixture thereof.

8. The binder composition of claim 1 , wherein the unsaturated compound comprises the unsaturated polyamide prepolymer, and wherein the unsaturated polyamide prepolymer comprises a reaction product of a polyamine and a polyacid.

9. The binder composition of claim 8 , wherein the polyamine comprises ethylenediamine, propylenediamine, hexamethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, 1,3-propanediamine, 1,4-butanediamine, and wherein the polyacid comprises maleic acid, itaconic acid, fumaric acid, glutaconic acid, citraconic acid, traumatic acid, muconic acid, aconitic acid, or a mixture thereof.

10. The binder composition of claim 8 , wherein the polyamine has the chemical formula:

wherein R 2 and R 3 are independently an organic group having 1 carbon atom to about 24 carbon atoms, and wherein n is an integer of 2 to 12, and
wherein the polyacid comprises maleic acid, itaconic acid, fumaric acid, glutaconic acid, citraconic acid, traumatic acid, muconic acid, aconitic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, phthalic acid, isophthalic acid, terephthalic acid, cyclobutanedicarboxylic acid, cyclopentanedicarboxylic acid, cyclohexanedicarboxylic acid, or a mixture thereof.

11. The binder composition of claim 1 , wherein the unsaturated compound comprises the unsaturated polyamide prepolymer, and wherein the unsaturated polyamide prepolymer comprises a reaction product of a polyamine and an ester.

12. The binder composition of claim 1 , wherein the unsaturated compound comprises the unsaturated polyurethane prepolymer, and wherein the unsaturated polyurethane prepolymer comprises a reaction product of a polyisocyanate and a polyol.

13. The binder composition of claim 1 , further comprising a reactive monomer.

14. The binder composition of claim 13 , wherein the reactive monomer comprises styrene, methyl styrene, chlorostyrene, vinyl toluene, divinyl benzene, vinyl acetate, acrylic acid, methacrylic acid, a lower alkyl ester of acrylic acid, a lower alkyl ester of methacrylic acid, diallyl phthalate, a vegetable oil, or a mixture thereof.

15. A process for making a composite product, comprising:
contacting a plurality of lignocellulose substrates with a binder composition comprising an unsaturated compound and a free radical precursor, wherein:
the unsaturated compound comprises 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, an unsaturated polyester prepolymer, an unsaturated polyether prepolymer, an unsaturated polyamide prepolymer, an unsaturated polyurethane prepolymer, or a mixture thereof,
the free radical precursor comprises an inorganic oxidant and a catalyst, and
a weight ratio of the free radical precursor to the unsaturated compound is at least 0.23:1 to about 40:1; and
heating the mixture to a temperature of about 60° C. to about 300° C. to produce a composite lignocellulose product.

16. The process of claim 15 , wherein:
the inorganic oxidant comprises hydrogen peroxide, and
the catalyst comprises an iron containing catalyst, and
the weight ratio of the free radical precursor to the unsaturated compound is about 0.3:1 to about 10:1.

17. The process of claim 15 , wherein the binder composition further comprises a reactive monomer.

18. A composite lignocellulose product, comprising a plurality of lignocellulose substrates and an at least partially cured binder composition, wherein the binder composition, prior to curing, comprises an unsaturated compound and a free radical precursor, wherein:
the unsaturated compound comprises 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, an unsaturated polyester prepolymer, an unsaturated polyether prepolymer, an unsaturated polyamide prepolymer, an unsatura

Assignees

• Georgia Pacific Chemicals Llc

Inventors

• Williamson Bobby L
• Sniady Adam K
• Swift Brian L
• Srinivasan Ramji
• Jing Feng
• Hagiopol Cornel

Classifications

• C08F222/1061

  of alcohol terminated polyesters or polycarbonates, e.g. polyester (meth)acrylates · CPC title

• C08F122/38

  Amides · CPC title

• B27N3/002

  characterised by the type of binder (compositions of macromolecular compounds C08L) · CPC title

• C09J167/06 Primary

  Unsaturated polyesters having carbon-to-carbon unsaturation · CPC title

• C09D135/02

  Homopolymers or copolymers of esters (C09D135/06, C09D135/08 take precedence) · CPC title