IP Library › Granted Patent US 7,553,896
Granted Patent B2
US 7,553,896 · App. 11/156,214 · Granted Jun 30, 2009

Ortho-nitrosophenols as polymerization inhibitors

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Quick Facts
Patent No.
US 7,553,896
App. No.
11/156,214
Granted
Jun 30, 2009
Kind
B2
Abstract

Disclosed herein is a method for inhibiting the premature polymerization of ethylenically unsaturated monomers comprising adding to said monomers an effective amount of at least one nitroso inhibitor of the structure: wherein R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of hydrogen, nitro, nitroso, halogen, COOR wherein R is hydrogen or alkyl, alkyl, and heteroatom-substituted alkyl; or adjacent groups R 1 , R 2 , R 3 , and R 4 can be taken together to form a substituted or unsubstituted fused six-membered ring. Also disclosed is a composition of matter comprising: A) an ethylenically unsaturated monomer and B) at least one nitroso compound of the above-described structure.

Claims (10)

1. A method for inhibiting and retarding the premature polymerization of ethylenically unsaturated monomers in a distillation process comprising

adding to said monomers an effective amount of a compound for inhibiting and retarding the premature polymerization of the ethylenically unsaturated monomers consisting of the structure:

wherein R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of hydrogen, nitro, nitroso, halogen, COOR wherein R is hydrogen or alkyl, alkyl, and heteroatom-substituted alkyl; or adjacent groups R 1 , R 2 , R 3 , and R 4 can be taken together to form a substituted or unsubstituted fused six-membered ring.

2. The method of claim 1 carried out in the presence of oxygen.

3. The method of claim 1 carried out in the absence of oxygen.

4. The method of claim 1 wherein the compound is 2-nitroso-naphthol.

5. The method of claim 1 wherein the compound is 1-nitroso-2-naphthol.

6. The method of claim 1 wherein the effective amount of the compound is from 1 to 2000 ppm based on the weight of the ethylenically unsaturated monomers.

7. The method of claim 1 wherein the ethylenically unsaturated monomer is selected from the group consisting of styrene, α -methylstyrene, styrene sulfonic acid, vinyltoluene, divinylbenzenes, polyvinylbenzenes, alkylated styrene, 2-vinylpyridine, acrylonitrile, methacrylonitrile, methyl acrylate, ethyl acrylate, methyl methacrylate, ethyl methacrylate, acrylic acid, methacrylic acid, butadiene, chloroprene, and isoprene.

8. The method of claim 1 wherein the distillation process is a continuous vacuum distillation process.

Assignments (14)
RELEASE OF SECURITY INTEREST RECORDED AT REEL 037207 FRAME 0959 Recorded Oct 16, 2018
From: CERBERUS BUSINESS FINANCE, LLC
To: ADDIVANT USA, LLC
Reel/Frame 047775/0963 →
RELEASE OF SECURITY INTEREST RECORDED AT REEL 030872 FRAME 0810 Recorded Oct 16, 2018
From: WELLS FARGO BANK
To: ADDIVANT USA, LLC
Reel/Frame 047240/0580 →
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 →
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 →
PATENT SECURITY AGREEMENT Recorded Dec 3, 2015
From: ADDIVANT USA, LLC
To: CERBERUS BUSINESS FINANCE, LLC, AS AGENT
Reel/Frame 037207/0959 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 1, 2014
From: CHEMTURA CORPORATION
To: ADDIVANT USA LLC
Reel/Frame 031895/0895 →
SECURITY INTEREST Recorded Jul 19, 2013
From: ADDIVANT USA, LLC
To: WELLS FARGO BANK, NATIONAL ASSOCIATION
Reel/Frame 030872/0810 →
PARTIAL RELEASE OF IP SECURITY AGREEMENT ABL Recorded May 8, 2013
From: BANK OF AMERICA, N.A.
To: CHEMTURA CORPORATION; BIO-LAB INC.; CROMPTON COLORS INCORPORATED; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; HOMECARE LABS, INC.; RECREATIONAL WATER PRODUCTS, INC.; WEBER CITY ROAD LLC; AQUA CLEAR INDUSTRIES, LLC; ASEPSIS, INC.; NAUGATUCK TREATMENT COMPANY; CNK CHEMICAL REALTY CORPORATION; KEM MANUFACTURING CORPORATION
Reel/Frame 030407/0063 →
PARTIAL RELEASE OF IP SECURITY AGREEMENT TL Recorded May 8, 2013
From: BANK OF AMERICA, N.A.
To: CHEMTURA CORPORATION; BIO-LAB INC.; CROMPTON COLORS INCORPORATED; GLCC LAUREL, LLC; GREAT LAKES CHEMICAL CORPORATION; HOMECARE LABS, INC.; RECREATIONAL WATER PRODUCTS, INC.; WEBER CITY ROAD LLC; AQUA CLEAR INDUSTRIES, LLC; ASEPSIS, INC.; NAUGATUCK TREATMENT COMPANY; CNK CHEMICAL REALTY CORPORATION; KEM MANUFACTURING CORPORATION
Reel/Frame 030411/0062 →
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 Aug 30, 2005
From: MA, QINGGAO; WORTMAN, WILLIAM; WANG, JAY; STOTT, PAUL E.
To: CHEMTURA CORPORATION
Reel/Frame 016469/0918 →