Binder compositions and methods for making and using same

Patent metadata

Field	Value
Publication number	US-9193894-B2
Application number	US-201414205440-A
Country	US
Kind code	B2
Filing date	Mar 12, 2014
Priority date	Mar 14, 2013
Publication date	Nov 24, 2015
Grant date	Nov 24, 2015

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 method for making a composite product, comprising:
combining a plurality of lignocellulose substrates, at least one unsaturated compound, and at least one free radical precursor to produce a mixture, wherein the unsaturated compound has 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 an unsaturated polyester prepolymer, an unsaturated polyether prepolymer, an unsaturated polyamide prepolymer, an unsaturated polyurethane prepolymer, or any mixture thereof; and
heating the mixture to a temperature of about 60° C. to about 300° C. to produce a composite product.

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

3. The method of claim 1 , wherein the free radical precursor comprises a mixture of hydrogen peroxide and one or more iron containing catalysts.

4. The method of claim 1 , wherein the free radical precursor is present in an amount of at least 30 wt % to about 99 wt %, based on the weight of the one or more unsaturated compounds.

5. The method of claim 1 , further comprising maintaining the mixture at a temperature less than 60° C. for at least 10 minutes prior to heating the mixture to the temperature of about 60° C. to about 300° C. to produce the composite product.

6. The method of claim 5 , wherein at least 11 wt % of the one or more free radical precursors is present when the mixture is heated to at least 60° C.

7. The method of claim 3 , wherein the iron containing catalyst comprises potassium ferricyanide, iron sulfate, iron ethylenediamine tetraacetic acid, iron (S,S)-ethylenediamine-N,N′-disuccinic acid, iron diethylenetriamine pentaacetic acid, iron ethyleneglycol bis(2-aminoethylether)-N,N,N′,N′-tetraacetic acid, iron trans-1,2-diaminocyclohexanetetraacetic acid, or any mixture thereof.

8. The method of claim 7 , wherein the iron containing catalyst comprises iron (S,S)-ethylenediamine-N,N′-disuccinic acid, iron diethylenetriamine pentaacetic acid, iron ethyleneglycol bis(2-aminoethylether)-N,N,N′,N′-tetraacetic acid, iron trans-1,2-diaminocyclohexanetetraacetic acid, or any mixture thereof.

9. A method for making a composite product, comprising:
combining a plurality of lignocellulose substrates, at least one unsaturated compound, and at least one free radical precursor to produce a mixture; and
heating the mixture to a temperature of about 60° C. to about 300° C. to produce a composite product, wherein:
the unsaturated compound has two or more unsaturated carbon-carbon bonds,
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
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, or any mixture thereof.

10. The method of claim 9 , wherein the free radical precursor comprises a mixture of hydrogen peroxide and one or more iron containing catalysts.

11. The method of claim 10 , wherein the iron containing catalyst comprises potassium ferricyanide, iron sulfate, iron ethylenediamine tetraacetic acid, iron (S,S)-ethylenediamine-N,N′-disuccinic acid, iron diethylenetriamine pentaacetic acid, iron ethyleneglycol bis(2-aminoethylether)-N,N,N′,N′-tetraacetic acid, iron trans-1,2-diaminocyclohexanetetraacetic acid, or any mixture thereof.

12. The method of claim 10 , wherein the iron containing catalyst comprises iron (S,S)-ethylenediamine-N,N′-disuccinic acid, iron diethylenetriamine pentaacetic acid, iron ethyleneglycol bis(2-aminoethylether)-N,N,N′,N′-tetraacetic acid, iron trans-1,2-diaminocyclohexanetetraacetic acid, or any mixture thereof.

13. The method of claim 9 , wherein the free radical precursor is present in an amount of at least 30 wt % to about 99 wt %, based on the weight of the one or more unsaturated compounds.

14. The method of claim 9 , further comprising maintaining the mixture at a temperature less than 60° C. for at least 10 minutes prior to heating the mixture to the temperature of about 60° C. to about 300° C. to produce the composite product.

15. The method of claim 14 , wherein at least 11 wt % of the one or more free radical precursors is present when the mixture is heated to at least 60° C.

16. A method for making a composite product, comprising:
combining a plurality of lignocellulose substrates, at least one unsaturated compound, and at least one free radical precursor to produce a mixture; and
heating the mixture to produce a composite product, wherein:
the unsaturated compound has two or more unsaturated carbon-carbon bonds,
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,
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,
the free radical precursor comprises a mixture of hydrogen peroxide and one or more iron containing catalysts, and
the iron containing catalyst comprises potassium ferricyanide, iron sulfate, iron ethylenediamine tetraacetic acid, iron (S,S)-ethylenediamine-N,N′-disuccinic acid, iron diethylenetriamine pentaacetic acid, iron ethyleneglycol bis(2-aminoethylether)-N,N,N′,N′-tetraacetic acid, iron trans-1,2-diaminocyclohexanetetraacetic acid, or any mixture thereof.

17. The method of claim 16 , wherein:
the unsaturated compound comprises 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, or any mixture thereof, and
the iron containing catalyst comprises iron (S,S)-ethylenediamine-N,N′-disuccinic acid, iron diethylenetriamine pentaacetic acid, iron ethyleneglycol bis(2-aminoethylether)-N,N,N′,N′-tetraacetic acid, iron trans-1,2-diaminocyclohexanetetraacetic acid, or any mixture thereof.

18. The method of claim 16 , wherein the free radical precursor is present in an amount of at least 30 wt % to about 99 wt %, based on the weight of the one or more unsaturated compounds.

19. The method of claim 16 , wherein:
the mixture is heated to a temperature of about 60° C. to about 300° C. to produce the composite product, and
the mixture is maintained at a temperature less than 60° C. for at least 10 minutes prior to heating the mixture to the temperature of about 60° C. to about 300° C. to produce the composite product.

20. The method of claim 19 , wherein at least 25 wt % of the one or more free radical precursors is present wh

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

• C08F222/12 Primary

  of phenols or saturated alcohols {(C08F222/1006 takes precedence)} · 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