IP Library Granted Patent US 8,183,311
Granted Patent B2
US 8,183,311 · App. 12/534,035 · Granted May 22, 2012

Liquid phosphite composition derived from cresols

Assignee: Chemtura Corporation
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Quick Facts
Patent No.
US 8,183,311
App. No.
12/534,035
Granted
May 22, 2012
Kind
B2
Abstract

A composition at least two different phosphites, one of which is derived from an alkylated cresol, wherein the composition is a liquid at ambient conditions. The other phosphites may be derived from alkylated cresol, alkylated phenol or other alkylated hydroxyaryl compounds. The cresol may be mono-alkylated or di-alkylated with a C 1 -C 18 alkyl group.

Claims (23)

1. A composition comprising a liquid phosphite, said liquid phosphite consisting of a mixture of at least two different phosphites of structure (I)

wherein R 1 , R 2 , and R 3 are independently selected alkylated aryl groups selected from the group consisting of t-butylphenyl, di-t-butylphenyl, t-amylphenyl, di-t-amylphenyl and cresyl of structure (III),

wherein R 4 , R 5 , and R 6 are independently selected from the group consisting of hydrogen, methyl, t-butyl and t-amyl; and

R 7 is hydrogen or methyl;

wherein one of R 4 , R 5 , R 6 , and R 7 is methyl and at least one of R 4 , R 5 , and R 6 , is t-butyl or t-amyl

provided that at least one of the phosphites comprises an alkylated cresyl of structure (III),

wherein the liquid phosphite consisting of a mixture of at least two different phosphites of structure (I) is a liquid at ambient conditions.

2. The composition of claim 1 , wherein the phosphite comprising an alkylated cresyl group is selected from the group consisting of tris(4-t-butyl-m-cresyl)phosphite, tris(2-t-butyl-m-cresyl)phosphite, tris(4,6-di-t-butyl-m-cresyl)phosphite, bis(4-t-butyl-m-cresyl)-4,6-di-t-butyl-m-cresyl phosphite, bis(2-t-butyl-m-cresyl)-4-t-butyl-m-cresyl phosphite, bis(2-t-butyl-m-cresyl)-4,6-di-t-butyl-m-cresyl phosphite, bis(4,6-di-t-butyl-m-cresyl)-4-t-butyl-m-cresyl phosphite, bis(4,6-di-t-butyl-m-cresyl)-2-t-butyl-m-cresyl phosphite, tris(4-t-amyl-m-cresyl)phosphite, tris(2-t-amyl-m-cresyl)phosphite, tris(4,6-di-t-amyl-m-cresyl)phosphite, bis(4-t-amyl-m-cresyl)-2-t-amyl-m-cresyl phosphite, bis(4-t-amyl-m-cresyl)-4,6-di-t-amyl-m-cresyl phosphite, bis(2-t-amyl-m-cresyl)-4-t-amyl-m-cresyl phosphite, bis(2-t-amyl-m-cresyl)-4,6-di-t-amyl-m-cresyl phosphite, bis(4,6-di-t-amyl-m-cresyl)-4-t-amyl-m-cresyl phosphite, and bis(4,6-di-t-amyl-m-cresyl)-2-t-amyl-m-cresyl phosphite.

3. The composition of claim 1 , wherein the phosphite comprises an alkylated cresyl group is selected from the group consisting of tris(2-t-butyl-p-cresyl)phosphite, tris(2,6-di-t-butyl-p-cresyl)phosphite, bis(2-t-butyl-p-cresyl)-2,6-di-t-butyl-p-cresyl phosphite, bis(2,6-di-t-butyl-p-cresyl)-2-t-butyl-p-cresyl phosphite, tris(2-t-amyl-p-cresyl)phosphite, tris(2,6-di-t-amyl-p-cresyl)phosphite, bis(2-t-amyl-p-cresyl)-2,6-di-t-amyl-p-cresyl phosphite, and bis(2,6-di-t-amyl-p-cresyl)-2-t-amyl-p-cresyl phosphite.

4. The composition of claim 1 , wherein the liquid phosphite is derived from a mixture of 5-95 wt % alkylated m-cresol and 5-95 wt % alkylated p-cresol.

5. The composition of claim 1 , wherein at least two different phosphites are derived from a mixture of 5-95 wt % of an alkylated cresol and 5-95 wt % of an alkylated phenol.

6. The composition of claim 1 , wherein the liquid phosphite comprises the following:

tris(monoalkylaryl)phosphite in an amount from 20 to 70 wt %;

bis(monoalkylaryl)dialkylaryl phosphite in an amount from 15 to 60 wt %,

tris(dialkylaryl)phosphite in an amount of from 0.1 to 20 wt %; or

bis(dialkylaryl)monoalkylaryl phosphite in an amount of from 2 to 20 wt %

wherein monoalkylaryl is selected from the group consisting of t-butylphenyl, t-amylphenol, and cresyl of structure (III) wherein one of R 4 , R 5 , and R 6 is t-butyl or t-amyl; and dialkylaryl is selected from the group consisting of di-t-butylphenyl, di-t-amylphenyl and cresyl of structure (III) wherein two of R 4 , R 5 , and R 6 are t-butyl or t-amyl.

7. A composition according to claim 1 comprising:

a polymer; and

the liquid phosiphite.

8. The composition of claim 7 , wherein the polymer is selected from the group consisting of polyolefin homopolymers and copolymers, thermoplastics, rubbers, polyesters, polyurethanes, polyalkylene terephthalates, polysulfones, polyimides, polyphenylene ethers, styrenic polymers and copolymers, polycarbonates, acrylic polymers, polyamides, polyacetals, halide-containing polymers, biodegradable polymers, and mixtures thereof.

9. The composition of claim 7 , further comprising a primary phenolic antioxidant.

10. The composition of claim 9 , wherein the primary phenolic antioxidants are selected from the group consisting of tetrakismethylene (3,5-di-t-butyl-4-hydroxylhydrocinnamate)methane, 1,3,5-tris(3,5-di-t-butyl-4-hydroxybenzyl)isocyanurate, 1,3,5-tris(4-t-butyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, octyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, bis(octadecyl)hydroxylamine, 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-4-hydroxybenzyl)benzene, 2,6-bis(α-methylbenzyl)-4-methylphenol, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-benzenepropanoic acid, and 2,6-di-t-butyl-4-ethyl-phenol and mixtures thereof.

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 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 →
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 →
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 →
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 13, 2011
From: GELBIN, MICHAEL E.; POWER, MAURICE; HILL, JONATHAN S.
To: CHEMTURA CORPORATION
Reel/Frame 025634/0783 →
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 →
Continuity (3)
Continuation In Part 11787531 · Apr 16, 2007
Provisional Application 60815819 · Jun 20, 2006
Related Publication 20100076125A1 · Mar 25, 2010