Binder compositions and methods for making and using same

Patent metadata

Field	Value
Publication number	US-9815928-B2
Application number	US-201615056112-A
Country	US
Kind code	B2
Filing date	Feb 29, 2016
Priority date	Mar 14, 2013
Publication date	Nov 14, 2017
Grant date	Nov 14, 2017

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:
a free radical precursor;
an unsaturated compound having two or more unsaturated carbon-carbon bonds, wherein at least one of the unsaturated carbon-carbon bonds is a pi-bond that is not conjugated with an aromatic moiety and is capable of free radical addition, and 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 any mixture thereof, and
a reactive monomer.

2. The binder composition of claim 1 , wherein the free radical precursor comprises one or more inorganic oxidants and one or more catalysts.

3. The binder composition of claim 1 , wherein the free radical precursor comprises hydrogen peroxide and an iron containing catalyst, and wherein the iron containing catalyst comprises 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 any mixture thereof.

4. The binder composition of claim 1 , wherein the free radical precursor comprises hydrogen peroxide and a catalyst, and wherein the hydrogen peroxide is present in an amount of about 10 wt % to about 80 wt % and the catalyst is present in an amount of about 0.01 wt % to about 20 wt %, based on a combined weight of the unsaturated compound and the free radical precursor.

5. The binder composition of claim 1 , wherein the free radical precursor is present in an amount of about 7 wt % to about 99 wt %, based on a weight of the one or more unsaturated compounds.

6. The binder composition of claim 1 , wherein the free radical precursor comprises azobisisobutyronitrile.

7. 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.

8. The binder composition of claim 7 , 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 any 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 any mixture thereof, and
the anhydride comprises phthalic anhydride, mellitic anhydride, pyromellitic anhydride, maleic anhydride, or any mixture thereof.

9. The binder composition of claim 1 , 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 any mixture thereof.

10. 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.

11. The binder composition of claim 10 , 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 any mixture thereof.

12. The binder composition of claim 10 , 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 any mixture thereof.

13. 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.

14. 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.

15. A binder composition, comprising:
a free radical precursor; and
an unsaturated polyamide prepolymer, wherein:
the free radical precursor comprises a mixture of hydrogen peroxide and a catalyst,
the catalyst comprises a metal ion bound to a complexing agent,
the metal ion comprises iron, copper, manganese, tungsten, or molybdenum,
the complexing agent comprises cyanide, sulfate, ethylenediaminetetraacetic acid, ethylenediamine-N,N′-disuccinic acid, ethyleneglycol bis(2-aminoethylether)-N,N,N′,N′-tetraacetic acid, diethylenetriaminepentaacetic acid, trans-1,2-diaminocyclohexane tetraacetic acid, iminodisuccinate, or nitrilotriacetic acid,
the unsaturated polyamide prepolymer comprises a reaction product of a polyamine and a polyacid or a reaction product of a polyamine and an ester, and
the binder composition comprises about 10 wt % to about 80 wt % of the hydrogen peroxide and about 0.01 wt % to about 20 wt % of the catalyst, based on a combined weight of the unsaturated polyamide prepolymer and the free radical precursor.

16. A binder composition, comprising:
a free radical precursor;
an unsaturated polyamide prepolymer; and
a reactive monomer, 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 any mixture thereof.

17. The binder composition of claim 15 , wherein the metal ion comprises iron.

18. The binder composition of claim 16 , wherein the free radical precursor comprises a mixture of hydrogen peroxide and a catalyst.

19. The binder composition of claim 18 , where

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

• C09J167/06 Primary

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

• C08F122/38

  Amides · CPC title

• B27N3/002

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

• C09D135/02

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