IP Library › Granted Patent US 7,442,732
Granted Patent B2
US 7,442,732 · App. 11/093,434 · Granted Oct 28, 2008

Hindered amine light stabilizers comprising neoalkanediol phosphites

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Quick Facts
Patent No.
US 7,442,732
App. No.
11/093,434
Granted
Oct 28, 2008
Kind
B2
Abstract

Disclosed herein are compounds of the structure: wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are independently selected alkyl groups, provided that R 1 is different from R 2 . The compounds are useful as stabilizers for thermoplastic resins.

Claims (25)

1. A compound of the structure:

wherein R 3 , R 4 , R 5 , and R 6 are independently selected alkyl groups, R 1 is ethyl, R 2 is butyl, and provided that said compound is a liquid at room temperature.

2. The compound of claim 1 wherein R 3 , R 4 , R 5 , and R 6 are independently selected from the group consisting of straight chain and branched chain alkyl moieties of from 1 to 8 carbon atoms.

3. The compound of claim 2 wherein R 3 , R 4 , R 5 , and R 6 are independently selected from the group consisting of straight chain and branched chain alkyl moieties of from 1 to 4 carbon atoms.

4. The compound of claim 3 wherein R 3 , R 4 , R 5 , and R 6 are all the same.

5. The compound of claim 1 wherein said compound is 2,2, 6,6-tetramethylpiperidin-4-ol-2-butyl-2-ethyl-1,3-propanediol-phosphite.

6. A stabilized composition comprising:

(A) a thermoplastic resin, and

(B) a stabilizing amount of:

(1) a compound having the structure:

wherein R 3 , R 4 , R 5 , and R 6 are independently selected alkyl groups, R 1 is ethyl, R 2 is butyl, and provided that said compound is a liquid at room temperature and, optionally,

(2) a co-stabilizer selected from the group consisting of phenolics, aromatic amines, hydroxylamines, alkylamine-N-oxides, lactones, and thioethers.

7. The composition of claim 6 wherein R 3 , R 4 , R 5 , and R 6 are independently selected from the group consisting of straight chain and branched chain alkyl moieties of from 1 to 8 carbon atoms.

8. The composition of claim 7 wherein R 3 , R 4 , R 5 , and R 6 are independently selected from the group consisting of straight chain and branched chain alkyl moieties of from 1 to 4 carbon atoms.

9. The composition of claim 8 wherein R 3 , R 4 , R 5 , and R 6 are all the same.

10. The composition of claim 6 wherein said compound is 2,2,6,6-tetramethylpiperidin-4-ol-2-butyl-2-ethyl-1,3-propanediol-phosphite.

11. A method for stabilizing a thermoplastic resin comprising adding to said resin a stabilizing amount of a stabilizer having the structure:

wherein R 3 , R 4 , R 5 , and R 6 are independently selected alkyl groups, R 1 is ethyl R 2 is butyl, and provided that said compound is a liquid at room temperature.

12. The method of claim 11 wherein R 3 , R 4 , R 5 , and R 6 are independently selected from the group consisting of straight chain and branched chain alkyl moieties of from 1 to 8 carbon atoms.

13. The method of claim 12 wherein R 3 , R 4 , R 5 , and R 6 are independently selected from the group consisting of straight chain and branched chain alkyl moieties of from 1 to 4 carbon atoms.

14. The method of claim 13 wherein R 3 , R 4 , R 5 , and R 6 are all the same.

15. The method of claim 12 wherein said stabilizer is 2,2,6,6-tetramethylpiperidin-4-ol-2-butyl-2-ethyl-1,3-propanediol-phosphite.

16. A method for the preparation of stabilizer having the structure:

wherein R 3 , R 4 , R 5 , and R 6 are independently selected alkyl groups, R 1 is ethyl, R 2 is butyl, and provided that said compound is a liquid at room temperature wherein the method comprises reacting a phosphorous trihalide with a tetraalkylpiperidinol and a 2-butyl-2-ethyl-1,3-propanediol.

17. The method of claim 16 wherein the 2-butyl-2-ethyl-1,3-propanediol is the first reacted with the phosphorous trihalide to yield the corresponding halophosphite, which is then reacted with the tetraalkylpiperidinol.

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 →
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
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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 →
CHANGE OF NAME Recorded Jan 14, 2013
From: CROMPTON CORPORATION
To: CHEMTURA CORPORATION
Reel/Frame 029699/0278 →
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
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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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 10, 2005
From: GELBIN, MICHAEL E.; GRAY, CARLOSS L.
To: CROMPTON CORPORATION
Reel/Frame 015989/0026 →