IP Library Granted Patent US 9,650,742
Granted Patent B2
US 9,650,742 · App. 14/566,986 · Granted May 16, 2017

Process for making hydrogels from hemicaustic byproduct

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Quick Facts
Patent No.
US 9,650,742
App. No.
14/566,986
Granted
May 16, 2017
Kind
B2
Abstract

A process for making a hydrogel forming material from a kraft or sulfite pulping process cellulosic pulp slurry by extracting hemicellulose heteropolymers from the cellulosic pulp slurry as a hemicaustic extract by treating the cellulosic pulp slurry with a cold caustic solution, then isolating the hemicaustic extract and preparing a mixture of the hemicellulose extract and a derivatizing agent comprised of a monofunctional etherifying agent and/or a polyfunctional organic cross-linking agent, and reacting the mixture to produce the hydrogel forming material. A polyvalent metal cross-linking agent can optionally be reacted with the hydrogel forming material to enhance its gel strength.

Claims (21)

1. A process for making a hydrogel forming material from a kraft or sulfite pulping process cellulosic pulp slurry consisting essentially of:

extracting hemicellulose heteropolymers from the kraft or sulfite pulping process cellulosic pulp slurry as a hemicaustic extract by treating the cellulosic pulp slurry with a cold caustic solution;

isolating the hemicaustic extract, wherein the hemicaustic extract comprises 2% by weight to 12% by weight hemicellulose heteropolymers and 2% to 8% by weight of caustic;

concentrating the hemicaustic extract to 5% by weight to 15% by weight hemicellulose heteropolymers and about 3% by weight to about 20% by weight of caustic compounds by nanofiltration;

preparing a heterogeneous reaction mixture comprised of the hemicaustic extract and a derivatizing agent comprised of a monofunctional etherifying agent and/or a polyfunctional organic cross-linking agent; and

raising the temperature of the reaction mixture to a temperature from about 50° C. to the boiling point of the reaction mixture for a time period sufficient to react the hemicaustic extract and the derivatizing agent and producing a reaction product comprising a hydrogel forming material.

2. The process of claim 1 , wherein the derivatizing agent comprises both a monofunctional etherifying agent and a polyfunctional organic cross-linking agent and the weight ratio of the monofunctional etherifying agent to the polyfunctional organic cross-linking agent is from 1:1 to 99:1.

3. A process for making a hydrogel forming material from a kraft or sulfite pulping process cellulosic pulp slurry consisting essentially of:

extracting hemicellulose heteropolymers from the kraft or sulfite pulping process cellulosic pulp slurry as a hemicaustic extract by treating the cellulosic pulp slurry with a cold caustic solution;

isolating the hemicaustic extract, wherein the hemicaustic extract comprises 2% by weight to 12% by weight hemicellulose heteropolymers and 2% to 8% by weight of caustic;

concentrating the hemicaustic extract to 5% by weight to 15% by weight hemicellulose heteropolymers and about 3% by weight to about 20% by weight of caustic compounds by evaporation;

preparing a heterogeneous reaction mixture comprised of the hemicaustic extract and a derivatizing agent comprised of a monofunctional etherifying agent and/or a polyfunctional organic cross-linking agent;

raising the temperature of the reaction mixture to a temperature from about 50° C. to the boiling point of the reaction mixture for a time period sufficient to react the hemicaustic extract and the derivatizing agent and producing a reaction product comprising a hydrogel forming material; and

neutralizing the hydrogel forming material to a pH from 3 to 12 by treatment with an acid, wherein the water content of the neutralized reaction product is from 10% by weight to 90% by weight and the reaction product is dried to a water content from 20% by weight to 50% by weight.

4. A process for making a hydrogel forming material from a kraft or sulfite pulping process cellulosic pulp slurry consisting essentially of:

extracting hemicellulose heteropolymers from the kraft or sulfite pulping process cellulosic pulp slurry as a hemicaustic extract by treating the cellulosic pulp slurry with a cold caustic solution;

isolating the hemicaustic extract;

preparing a heterogeneous reaction mixture comprised of the hemicaustic extract and a derivatizing agent comprised of a monofunctional etherifying agent and a polyfunctional organic cross-linking agent, wherein the monofunctional etherifying agent comprises an alkyl halide, halocarboxylic acid, halofatty acid, haloalkylsulphonic acid, haloalkylammonium compound, halohydin, chloroacetic acid, a chloroacetic acid salt, chloromethane, an alkylene oxide, epoxychlorohdrin or an epoxy carboxylic acid and the polyfunctional organic cross-linking agent comprises ethylene glycol diglycidyl ether, glycerol triglycidyl ether, glycerol diglycidyl ether, glycerol propoxylate triglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol glycidyl ether, 1,4-cyclohexanoldimethanol diglycidyl ether, 1,2-dichloroacetic acid, a salt of 1,2-dichloroacetic or 1,3-dichloropropanol; and

raising the temperature of the reaction mixture to a temperature from about 50° C. to the boiling point of the reaction mixture for a time period sufficient to react the hemicaustic extract and the derivatizing agent and producing a reaction product comprising a hydrogel forming material.

5. The process of claim 4 , wherein the weight ratio of the monofunctional etherifying agent to the polyfunctional organic cross-linking agent is from 1:1 to 99:1.

6. The process of claim 5 , further comprising the step of adding a polyvalent metal cross-linking agent to the reaction product and reacting it with the hydrogel forming material and wherein the polyvalent metal cross-linking agent comprises titanium(IV) oxysulfate, titanium (IV) tetrachloride, titanium sulfate, tetrakis(isopropoxy)-titanium, aluminum sulfate, zirconium oxychloride, zirconium orthosulfate, zirconium acetate, zirconium tetrachloride, zirconium carbonate, zirconium ammonium carbonate, titanium dioxide, zirconium acetylacetonate, titanium citrate, titanium malate, titanium tartrate, zirconium lactate, and aluminum acetate, sodium borate, sodium tetraborate, disodium tetraborate, potassium borate or potassium tetraborate.

Assignments (7)
RELEASE OF SECURITY INTEREST Recorded Nov 7, 2024
From: COMPUTERSHARE TRUST COMPANY, N.A. AS SUCCESSOR TO WELLS FARGO BANK
To: RAYONIER ADVANCED MATERIALS INC.; RAYONIER PERFORMANCE FIBERS, LLC
Reel/Frame 069190/0878 →
RELEASE OF SECURITY INTEREST Recorded Dec 28, 2020
From: BANK OF AMERICA, N.A.
To: RAYONIER ADVANCED MATERIALS INC.; RAYONIER PERFOMANCE FIBERS, LLC
Reel/Frame 054752/0295 →
SECURITY AGREEMENT Recorded Dec 23, 2020
From: RAYONIER PERFORMANCE FIBERS, LLC; RAYONIER ADVANCED MATERIALS INC.
To: BANK OF AMERICA, N.A., AS COLLATERAL AGENT
Reel/Frame 054842/0950 →
SECURITY AGREEMENT Recorded Dec 23, 2020
From: RAYONIER PERFORMANCE FIBERS, LLC; RAYONIER ADVANCED MATERIALS INC.
To: WELLS FARGO BANK, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 054843/0044 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT SUPPLEMENT Recorded Nov 22, 2017
From: RAYONIER PERFORMANCE FIBERS, LLC; RAYONIER ADVANCED MATERIALS INC.
To: BANK OF AMERICA, N.A.
Reel/Frame 044803/0939 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 12, 2014
From: HAMED, OTHMAN A
To: RAYONIER PERFORMANCE FIBERS, LLC
Reel/Frame 034489/0725 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 12, 2014
From: KRZYWANSKI, ROMUALD S
To: RAYONIER PERFORMANCE FIBERS, LLC
Reel/Frame 034489/0793 →