IP Library Granted Patent US 8,217,133
Granted Patent B2
US 8,217,133 · App. 11/702,787 · Granted Jul 10, 2012

Storage stable one component polyurethane system

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Quick Facts
Patent No.
US 8,217,133
App. No.
11/702,787
Granted
Jul 10, 2012
Kind
B2
Abstract

In one aspect, the invention relates to storage-stable and flowable polyurethane compositions comprising (a) one or more isocyanate-terminated polyurethane prepolymers derived from one or more hydrocarbon ring-containing diisocyanates and/or triisocyanates and one or more polyols; (b) one or more metal salt complexes of methylenedianiline; and (c) one or more organic acid halide compounds having one or more acid halide groups, wherein the one or more organic acid halide compounds are in an amount wherein the acid halide groups are present in a minimum concentration of about 100 parts per million by weight of the polyurethane prepolymer. In other aspects, the invention relates to methods for storing the curable polyurethane compositions, as well as methods for producing polyurethane elastomers.

Claims (11)

1. A storage-stable flowable, one component polyurethane composition comprising

(a) one or more isocyanate-terminated polyurethane prepolymers derived from one or more hydrocarbon ring-containing diisocyanates or triisocyanates and one or more polyols;

(b) one or more metal salt complexes of methylenedianiline; and

(c) one or more organic acid halide compounds having one or more acid halide groups, wherein the acid halide groups are present in a concentration of from about 100 parts per million to about 20,000 parts per million by weight of the polyurethane prepolymer,

prepared by a process comprising adding one or more organic acid halide compounds having one or more acid halide groups, to one or more isocyanate-terminated polyurethane prepolymers, said prepolymer prepared from a polyol and a hydrocarbon ring-containing diisocyanate or triisocyanate, to form a prepolymer/acid halide mixture, mixing said mixture,

and then adding to the mixture, under agitation, one or more metal salt complexes of methylenedianiline and mixing to obtain the storage-stable flowable, one component polyurethane composition,

which composition has a viscosity below 100,000 centipoise at 50° C., and remains flowable and non-elastomeric, as determined at about 50° C., for at least ninety days at a temperature of about 35° C., and at least about fourteen days at a temperature of about 50° C. to about 70° C. which composition forms a polyurethane elastomer product upon heating to a temperature in a range of about 100° C. to 150° C.

2. The storage-stable flowable, one component polyurethane composition according to claim 1 , wherein the polyurethane prepolymer is prepared from a polyol and one or more hydrocarbon ring-containing diisocyanates selected from the group consisting of paraphenylene diisocyanate, tolidene diisocyanate, isophorone diisocyanate, isomers of methylene bis(phenylisocyanate), isomers of toluene diisocyanate, diphenyl-4,4′-diisocyanate, dibenzyl-4,4′-diisocyanate, stilbene-4,4′-diisocyanate, benzophenone-4,4′diisocyanate, 1,3- and 1,4-xylene diisocyanates, 1,3-cyclohexyl diisocyanate, 1,4-cyclohexyl diisocyanate, 4,4′-methylene bis(phenylisocyanate), isomers of 1,1′-methylene-bis(4-isocyanatocyclohexane), isomers of benzenetriisocyanate, toluene-2,4,6-triisocyanate, 2,4,4′-triisocyanatediphenylether, and tolylene and xylylene diisocyanate derivatives of trimethylolpropane.

3. The storage-stable flowable, one component polyurethane composition according to claim 1 , wherein the one or more organic acid halide compounds having one or more acid halide groups is selected from the group consisting of adipoyl chloride, benzoyl chloride, phthaloyl chloride, isophthaloyl chloride, terephthaloyl chloride, acetyl chloride, palmitoyl chloride, p-nitrobenzoyl chloride, 2-chlorobenzoyl chloride, 3-chlorobenzoyl chloride, 4-chlorobenzoyl chloride, oleoyl chloride, and stearoyl chloride.

4. The storage-stable flowable, one component polyurethane composition according to claim 1 wherein the polyurethane prepolymer is prepared from a polyol and one or more hydrocarbon ring-containing diisocyanates selected from the group consisting of methylene diphenyl diisocyanate, paraphenylene diisocyanate and toluene diisocyanate and the one or more organic acid halide compounds having one or more acid halide groups is selected from the group consisting of benzoyl chloride, phthaloyl chloride, isophthaloyl chloride, terephthaloyl chloride, p-nitrobenzoyl chloride, 2-chlorobenzoyl chloride, 3-chlorobenzoyl chloride and 4-chlorobenzoyl chloride.

5. The storage-stable flowable, one component polyurethane composition according to claim 1 having a viscosity below 30,000 centipoise at 50° C.

Assignments (12)
MERGER AND CHANGE OF NAME Recorded Sep 7, 2018
From: CHEMTURA CORPORATION; LANXESS SOLUTIONS US INC.
To: LANXESS SOLUTIONS US INC.
Reel/Frame 046811/0266 →
RELEASE OF AMENDED AND RESTATED SECOND LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded May 12, 2017
From: BANK OF AMERICA, N.A.
To: CHEMTURA CORPORATION; CROMPTON COLORS INCORPORATED; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION
Reel/Frame 042452/0759 →
RELEASE OF THIRD LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded May 12, 2017
From: BANK OF AMERICA, N.A.
To: CHEMTURA CORPORATION; CROMPTON COLORS INCORPORATED; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION
Reel/Frame 042452/0894 →
RELEASE OF FIRST LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded May 11, 2017
From: BANK OF AMERICA, N.A.
To: CHEMTURA CORPORATION; BIOLAB FRANCHISE COMPANY, LLC; BIO-LAB, INC.; CROMPTON COLORS INCORPORATED; CROMPTON HOLDING CORPORATION; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; GREAT LAKES CHEMICAL GLOBAL, INC.; GT SEED TREATMENT, INC.; HOMECARE LABS, INC.; LAUREL INDUSTRIES HOLDINGS, INC.; RECREATIONAL WATER PRODUCTS, INC.; WEBER CITY ROAD LLC
Reel/Frame 042447/0508 →
RELEASE OF SECOND LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded May 11, 2017
From: BANK OF AMERICA, N.A.
To: CHEMTURA CORPORATION; BIOLAB FRANCHISE COMPANY, LLC; BIO-LAB, INC.; CROMPTON COLORS INCORPORATED; CROMPTON HOLDING CORPORATION; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; GREAT LAKES CHEMICAL GLOBAL, INC.; GT SEED TREATMENT, INC.; HOMECARE LABS, INC.; LAUREL INDUSTRIES HOLDINGS, INC.; RECREATIONAL WATER PRODUCTS, INC.; WEBER CITY ROAD LLC
Reel/Frame 042449/0001 →
THIRD LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Jul 18, 2014
From: CHEMTURA CORPORATION; CROMPTON COLORS INCORPORATED; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION
To: BANK OF AMERICA, N.A.
Reel/Frame 033360/0325 →
AMENDED AND RESTATED SECOND LIEN INTELLECTUAL PROPERY SECURITY AGREEMENT Recorded Jul 18, 2014
From: CHEMTURA CORPORATION; CROMPTON COLORS INCORPORATED; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION
To: BANK OF AMERICA, N.A.
Reel/Frame 033360/0225 →
FIRST LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT. Recorded Mar 21, 2011
From: CHEMTURA CORPORATION; BIOLAB FRANCHISE COMPANY, LLC; BIO-LAB, INC.; CROMPTON COLORS INCORPORATED; CROMPTON HOLDING CORPORATION; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; GREAT LAKES CHEMICAL GLOBAL, INC.; GT SEED TREATMENT, INC.; HOMECARE LABS, INC.; LAUREL INDUSTRIES HOLDINGS, INC.; RECREATIONAL WATER PRODUCTS, INC.; WEBER CITY ROAD LLC
To: BANK OF AMERICA, N.A.
Reel/Frame 026028/0622 →
INTELLECTUAL PROPERTY SECURITY RELEASE AGREEMENT Recorded Mar 21, 2011
From: CITIBANK, N.A.
To: CHEMTURA CORPORATION; A & M CLEANING PRODUCTS, LLC; ASCK, INC; BIOLAB COMPANY STORE, LLC; AQUA CLEAR INDUSTRIES, LLC; ASEPSIS, INC.; BIOLAB TEXTILES ADDITIVES, LLC; BIOLAB, INC.; CROMPTON COLORS INCORPORATED; CROMPTON MONOCHEM, INC.; CNK CHEMICAL REALTY CORPORATION; CROMPTON HOLDING CORPORATION; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; GT SEED TREATMENT, INC.; ISCI, INC; GREAT LAKES CHEMICAL GLOBAL, INC.; HOMECARE LABS, INC.; KEM MANUFACTURING CORPORATION; LAUREL INDUSTRIES HOLDINGS, INC.; NAUGATUCK TREATMENT COMPANY; UNIROYAL CHEMICAL COMPANY LIMITED (DELAWARE); MONOCHEM, INC.; RECREATIONAL WATER PRODUCTS, INC.; WEBER CITY ROAD LLC; WRL OF INDIANA, INC.; BIOLAB FRANCHISE COMPANY, LLC
Reel/Frame 026039/0142 →
SECDOND LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Mar 21, 2011
From: CHEMTURA CORPORATION; BIOLAB FRANCHISE COMPANY, LLC; BIO-LAB, INC.; CROMPTON COLORS INCORORATED; CROMPTON HOLDING CORPORATION; CLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; GREAT LAKES CHEMICAL GLOBAL, INC.; GT SEED TREATMENT, INC.; HOMECARE LABS, INC.; HAOMECARE LABS, INC.; LAUREL INDUSTRIES HOLDINGS, INC.; RECREATIONAL WATER PRODUCTS, INC.; WEBER CITY ROAD LLC
To: BANK OF AMERICA, N. A.
Reel/Frame 027881/0347 →
AMENDED AND RESTATED INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Feb 22, 2010
From: CHEMTURA CORPORATION; A & M CLEANING PRODUCTS, LLC; AQUA CLEAR INDUSTRIES, LLC; ASCK, INC.; ASEPSIS, INC.; BIOLAB COMPANY STORE, LLC; BIOLAB FRANCHISE COMPANY, LLC; BIOLAB TEXTILE ADDITIVES, LLC; BIO-LAB, INC.; CNK CHEMICAL REALTY CORPORATION; CROMPTON COLORS INCORPORATED; CROMPTON HOLDING CORPORATION; CROMPTON MONOCHEM, INC.; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; GREAT LAKES CHEMICAL GLOBAL, INC.; GT SEED TREATMENT, INC.; HOMECARE LABS, INC.; ISCI, INC.; KEM MANUFACTURING CORPORATION; LAUREL INDUSTRIES HOLDINGS, INC.; MONOCHEM, INC.; NAUGATUCK TREATMENT COMPANY; RECREATIONAL WATER PRODUCTS, INC.; UNIROYAL CHEMICAL COMPANY LIMITED (DELAWARE); WEBER CITY ROAD LLC; WRL OF INDIANA, INC.
To: CITIBANK, N.A.
Reel/Frame 023998/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 12, 2007
From: NAGARAJ, PHANIRAJ T.; ARCHIBALD, R. SCOTT; DOYLE, THOMAS R.; ROSENBERG, RONALD O.
To: CHEMTURA CORPORATION
Reel/Frame 019150/0731 →