IP Library Granted Patent US 7,943,809
Granted Patent B2
US 7,943,809 · App. 12/582,419 · Granted May 17, 2011

Composition and method for inhibiting polymerization and polymer growth

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 7,943,809
App. No.
12/582,419
Granted
May 17, 2011
Kind
B2
Abstract

A method for inhibiting the premature polymerization and the polymer growth of ethylenically unsaturated monomers is disclosed wherein the method comprises adding to said monomers an effective amount of at least one hydrogen donor or electron acceptor. In a preferred embodiment, the hydrogen donor or electron acceptor is used in combination with a stable nitroxyl free radical.

Claims (25)

1. A method for inhibiting polymer growth of a polymer present in ethylenically unsaturated monomers, said monomers selected from the group consisting of styrene, α-methylstyrene, styrene sulfonic acid, divinylbenzene, polyvinylbenzene, alkylated styrene, butadiene and isoprene monomers, said process comprising

(A) providing the polymer to the ethylenically unsaturated monomers; and

(B) adding to the ethylenically unsaturated monomers, an inhibitor composition consisting of:

(i) at least one first inhibitor consisting of a hydrogen donor of the structure

wherein R 104 , R 105 , R 106 , R 107 , R 108 , and R 109 are independently selected from the group consisting of hydrogen, alkyl, aryl, cycloalkyl, heterocyclic, substituted alkyl, substituted aryl, OR 110 , —SR 110 , NO, NO 2 , CN, COR 112 , halogen, and/or any two adjacent groups can be taken together to form ring structure(s), respectively of five to seven members, provided that at least one of R 104 , R 105 , R 106 , R 107 , R 108 , and R 109 is OH;

R 110 and R 111 are independently selected from the group consisting of hydrogen, alkyl, aryl, benzyl, cyclic, heterocyclic, substituted alkyl or aryl where the substituents are C, O, N, S, or P, and COR 102 , or R 110 and R 111 can be taken together to form a ring structure of five to seven members;

R 112 is R 102 , OR 102 , or NR 102 R 103 ,

R 102 and R 103 are independently selected from the group consisting of hydrogen, alkyl, aryl, benzyl, cyclic, heterocyclic, and substituted alkyl or aryl where the substituents are C, O, N, S, or P, or R 102 and R 103 can be taken together to form a ring structure of five to seven members, and

(ii) at least one second inhibitor having the following structural formula:

wherein

R 1 and R 4 are independently selected from the group consisting of hydrogen, alkyl, and heteroatom-substituted alkyl,

R 2 and R 3 are independently selected from the group consisting of alkyl and heteroatom-substituted alkyl, and

X 1 and X 2

(1) are independently selected from the group consisting of halogen, cyano, amido, —S—C 6 H 5 , carbonyl, alkenyl, alkyl of 1 to 15 carbon atoms COOR 7 , —S—COR 7 , —OCOR 7 , wherein R 7 is alkyl or aryl, or

(2) taken together, form a ring structure with the nitrogen; and

(iii) N-phenyl-N′-(1,4-dimethylpentyl)-para-phenylenediamine and wherein the polymer's growth is decreased by the presence of the inhibitor composition.

2. The method of claim 1 , wherein the at least one first inhibitor is 2,4-di-nitro-sec-butyl-phenol.

3. The method of claim 1 , wherein the at least one second inhibitor is 4-oxo-2,2,6,6-tetramethyl-piperidinyloxy.

4. The method of claim 1 , wherein the weight ratio of the at least one first inhibitor and the least one second inhibitor is 10:1.

5. The method of claim 1 , wherein the at least one first inhibitor is present in an amount of 1500 ppm and the at least one second inhibitor is present in an amount of 150 ppm.

6. The method of claim 1 , wherein the polymer's growth is decreased by 2%.

7. The method of claim 1 , wherein the ethylenically unsaturated monomers are selected from the group consisting of styrene, α-methylstyrene, divinylbenzene, polyvinylbenzene and alkylated styrene monomers.

8. The method of claim 1 , wherein the polymer comprises monomers selected from the group consisting of styrene, α-methylstyrene, styrene sulfonic acid, divinylbenzene, polyvinylbenzene, alkylated styrene, butadiene and isoprene monomers.

9. The method of claim 7 , wherein the polymer comprises monomers selected from the group consisting of styrene, α-methylstyrene, divinylbenzene, polyvinylbenzene and alkylated styrene monomers.

10. The method of claim 1 , wherein the monomers which form the polymer are the same as the monomers in which the polymer is present.

Assignments (13)
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 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 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 →