IP Library Granted Patent US 8,013,083
Granted Patent B2
US 8,013,083 · App. 11/345,194 · Granted Sep 6, 2011

Means for controlling the exothermic reaction of styrenic monomers with sulfonic acids

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Quick Facts
Patent No.
US 8,013,083
App. No.
11/345,194
Granted
Sep 6, 2011
Kind
B2
Abstract

A method for inhibiting the premature polymerization of styrenic monomers is disclosed wherein the method comprises adding to said monomers a combination of: (A) at least one inhibitor that is a sulfonic acid compound in a concentration sufficient to initiate cationic polymerization of said styrenic monomers at any point of the manufacturing or purification process and cause a resulting temperature increase; and (B) at least one amine in a concentration sufficient to reduce said cationic polymerization and said temperature increase; whereby an uncontrolled exothermic reaction between said sulfonic acid compound and said styrenic monomers will be prevented.

Claims (10)

1. A method for inhibiting the premature polymerization of styrenic monomers comprising adding to said monomers a combination of:

(A) from about 0.5 percent by weight to about 3 percent by weight of at least one sulfonic acid compound selected from the group consisting of toluenesulfonic acid, xylenesulfonic acid, cumenesulfonic acid, dodecylbenzenesulfonic acid, pentadecylbenzenesulfonic acid, dinonylnaphthalenesulfonic acid; and

(B ) about 0.25 to about 0.5 molar equivalents per molar equivalent of said sulfonic acid compound of at least one amine selected from the group consisting of pyridine, 2,6-dimethyl-4-aminopyridine, 2,6-lutidine, N-(1,4-dimethylpentyl)aniline, and methyl aniline; and,

(C) at least one inhibitor selected from the group consisting of a nitrophenol, a nitroxyl compound, and a nitrosoaniline

whereby an uncontrolled exothermic reaction of styrenic monomer will be prevented.

2. The method of claim 1 wherein said inhibitor (C) is 2,4-dinitro-6-sec-butylphenol.

3. The method of claim 1 wherein said inhibitor (C) is a nitrosoaniline of the structure:

wherein R 21 and R 22 are independently selected from the group consisting of hydrogen, alkyl, aryl, acyl, hydroxyl, alkoxy, nitroso, and sulfonyl, or R 21 and R 22 can form a cyclic ring that is aryl, cycloalkyl, polyaryl, or heterocyclic;

R 23 through R 27 are independently selected from the group consisting of hydrogen, alkyl, aryl, acyl, hydroxyl, alkoxy, acyloxy, NR 28 (R 29 ), nitro, nitroso, halogen, and sulfonyl, or any two adjacent R's can form a cyclic ring that is aryl, cycloalkyl, polyaryl, or heterocyclic, provided that at least one of R 23 through R 27 must be a nitroso group; and

R 28 and R 29 are independently selected from the group consisting of hydrogen, alkyl, aryl, acyl, and nitroso.

Assignments (17)
RELEASE OF SECURITY INTEREST Recorded Nov 1, 2024
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: SI GROUP, INC.; ADDIVANT USA, LLC; SI GROUP USA (USAA), LLC (F/K/A ADDIVANT USA, LLC)
Reel/Frame 069290/0057 →
CHANGE OF NAME Recorded Dec 2, 2019
From: ADDIVANT USA, LLC
To: SI GROUP USA (USAA), LLC
Reel/Frame 051159/0077 →
SECURITY INTEREST Recorded Nov 16, 2018
From: SI GROUP, INC.; ADDIVANT USA, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 048822/0965 →
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 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 →
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 Mar 15, 2006
From: KOSOVER, VILEN; FABIAN, JESUS R.; LIPPAI, ISTVAN; BENAGE, BRIGITTE; ABRUSCATO, GERALD J.
To: CHEMTURA CORPORATION
Reel/Frame 017306/0705 →