IP Library Granted Patent US 7,217,765
Granted Patent B2
US 7,217,765 · App. 10/739,598 · Granted May 15, 2007

Styrenic polymer composites

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Quick Facts
Patent No.
US 7,217,765
App. No.
10/739,598
Granted
May 15, 2007
Kind
B2
Abstract

A composite composition is disclosed that comprises the reaction product of a mixture of a styrenic polymer, as defined herein, a polar component having nucleophilic functional groups, and from 0.5 to 10 wt % of a compatibilizer having the formula: R y (I)-(styrene) n -[(styrene) m (X)] p —I(R y ) wherein: R is the residue of a nitroxide used to regulate the polymerization of the compatibilizer; I is the residue of a radical initiator used to initiate polymerization of the compatibilizer; n is an integer from 50 to 750; m is an integer from 0 to 10; p is an integer from 1 to 50; and y is an integer from 0 to 1; and X is any polymerized monomeric moiety having at least one functional group capable of reacting with the nucleophilic functional groups present in the polar component of the composite at the temperature at which the composite components are mixed.

Claims (25)

1. A composite composition comprising the reaction product of a mixture of a styrenic polymer; a polar component having nucleophilic functional groups and selected from the group consisting of glass, polyamides, and mixtures thereof, and from 1–3 wt % of a compatibilizer having the formula:

R y (I)-(styrene) n -[(styrene) m (X)] p —I(R y )

wherein:

R is the residue of a nitroxide used to regulate the polymerization of the compatibilizer;

I is the residue of a radical initiator used to initiate polymerization of the compatibilizer;

n is an integer from 50 to 750;

m is an integer from 0 to 10; p is an integer from 1 to 50;

y is an integer from 0 to 1; and

X is selected from the group consisting of maleic anhydride, tert.-butyl acrylate, and glycidyl methacrylate.

2. The composition of claim 1 wherein the polar component having nucleophilic functional groups is selected from the group consisting of glass fibers, polyamide-6, polyamide-66, polyamide-12, and mixtures thereof.

3. The composition of claim 1 wherein the polar component having nucleophilic functional groups is selected from the group consisting of polyamide-6, polyamide-66, polyamide-12, and mixtures thereof.

4. The composition of claim 1 wherein m is 0 and X is maleic anhydride.

5. The composition of claim 1 wherein m is 0 and X is tert.-butyl acrylate.

6. The composition of claim 1 wherein m is 0 and X is glycidyl methacrylate.

7. The composition of claim 3 wherein m is 0 and X is maleic anhydride.

8. The composition of claim 3 wherein m is 0 and X is tert.-butyl acrylate.

9. The composition of claim 3 wherein m is 0 and X is glycidyl methacrylate.

10. The composition of claim 1 wherein the compatibilizer is (polystyrene-co-maleic anhydride)-block-polystyrene or polystyrene-block-tert-butyl acrylate polymer wherein the number average molecular weight, M n , of the polystyrene block is 25,000–45,000 and the maleic anhydride or butyl acrylate is either a single unit on the end of the polystyrene chain or is present in a poly(styrene-co-maleic anhydride) or poly(butyl acrylate) block having an M n of from 1000–7000.

11. The composition of claim 1 wherein I is the residue of a peroxide, an alkyl-azo compound, or an alkoxyamine compound.

12. The composition of claim 1 wherein y is 1 and R is the residue of stable free radical compound that is a polymerization inhibitor having the structural formula:

wherein: R 1 and R 4 are independently selected from the group consisting of hydrogen, alkyl, and heteroatom-substituted alkyl and 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, COOR 11 (wherein R 11 is alkyl or aryl), amido, —S—C 6 H 5 , —S—COCH 3 , —OCOC 2 H 5 , carbonyl, alkenyl, or alkyl of 1 to 15 carbon atoms, or

(2) can be taken together to form a ring structure with the nitrogen of five, six, or seven members.

13. The composition of claim 12 wherein the stable free radical compound is 2,2,6,6-tetramethyl-piperidin-4-one-1-oxyl.

14. The composition of claim 1 wherein the styrenic polymer is a polymer or copolymer of styrene.

Assignments (14)
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 →
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 →
CHANGE OF NAME Recorded Feb 26, 2013
From: CROMPTON CORPORATION
To: CHEMTURA CORPORATION
Reel/Frame 029878/0378 →
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 →
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 →
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 →
SECURITY AGREEMENT Recorded May 12, 2009
From: CHEMTURA CORPORATION; A & M CLEANING PRODUCTS, LLC; AQUA CLEAR INDUSTRIES, LLC; ASCK, INC.; ASEPSIS, INC.; BIOLAB TEXTILE ADDITIVES, LLC; BIO-LAB, INC.; CNK CHEMICAL REALTY CORPORATION; CROMPTON HOLDING CORPORATION; CROMPTON COLORS INCORPORATED; CROMPTON MONOCHEM, INC.; 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.; BIOLAB COMPANY STORE, LLC; BIOLAB FRANCHISE COMPANY, LLC; GLCC LAUREL, LLC
To: CITIBANK, N.A.
Reel/Frame 022668/0658 →
RELEASE OF LIEN IN PATENTS Recorded Jul 13, 2005
From: DEUTSCHE BANK AG, NEW YORK BRANCH
To: CROMPTON CORPORATION
Reel/Frame 016513/0745 →
SECURITY AGREEMENT Recorded Nov 10, 2004
From: CROMPTON CORPORATION
To: DEUTSCHE BANK AG NEW YORK BRANCH
Reel/Frame 015370/0467 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 30, 2004
From: HONG, SUNG C.; MA, QINGGAO; STOTT, PAUL E.; WEFER, JOHN M.; ALLEN, LEIGH C.
To: CROMPTON CORPORATION
Reel/Frame 014919/0934 →