IP Library Granted Patent US 8,633,267
Granted Patent B2
US 8,633,267 · App. 12/804,680 · Granted Jan 21, 2014

Liquid phosphite compositions having different alkyl groups

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Quick Facts
Patent No.
US 8,633,267
App. No.
12/804,680
Granted
Jan 21, 2014
Kind
B2
Abstract

A composition comprising a mixture of at least two different alkylaryl phosphites, wherein some alkyl groups have a different number of carbon atoms than other alkyl groups and wherein the mixture is a liquid at ambient conditions.

Claims (40)

1. A composition comprising a mixture of alkylaryl phosphites and from 0 to 10% by weight of one or more free phenol based on the combined weight of all phosphites and said free phenol in the composition,

said mixture of alkylaryl phosphites comprising;

one or more phosphites of structure

one or more phosphites of structure

and one or more phosphites of structure

wherein

a, b, c, and d are independently selected from 0, 1, 2, and 3, provided that a+b=3 and c+d=3,

e, f, g and h are independently selected from 0, 1 and 2, provided that e+f+g+h=3, e+f=1 or 2, and g+h=1 or 2,

each Ar is phenyl,

each R 8 is a straight or branched C 1 -C 18 alkyl group having the same number of carbon atoms,

each R 9 is a straight or branched C 1 -C 18 alkyl group having the same number of carbon atoms, provided that R 8 has a different number of carbon atoms than R 9 , and the molar ratio of R 8 groups to R 9 groups in the phosphite mixture is from 1:10 to 10:1,

which mixture of alkylaryl phosphites comprises

one or more tris(monoalkylaryl) phosphites in an amount from 20 to 80 weight percent

one or more bis(monoalkylaryl)dialkylaryl phosphites in an amount from 15 to 60 weight percent,

one or more bis(dialkylaryl)alkylaryl phosphites in an amount from 2 to 20 weight percent,

one or more tris(dialkylaryl) phosphites in an amount from 0.1 to 20 weight percent based on the total weight of all phosphites in the phosphite composition,

and said one or more free phenol is selected from the group consisting of

wherein R 8 and R 9 are as defined above,

wherein the composition consisting of the mixture of alkylaryl phosphites and free phenol is a liquid at ambient conditions.

2. The composition of claim 1 , wherein R 8 and R 9 are selected from n-butyl, sec-butyl, t-butyl, n-amyl, sec-amyl, neo-amyl and t-amyl.

3. The composition of claim 2 , wherein R 8 is t-butyl and R 9 is t-amyl.

4. The composition of claim 3 , comprising from 0.01 to 5 weight percent of said free phenol.

5. The composition of claim 3 , comprising less than 1 weight percent of said free phenol.

6. The composition of claim 1 , comprising from 0.01 to 5 weight percent of said free phenol.

7. The composition of claim 1 , comprising less than 1 weight percent of said free phenol.

8. The composition of claim 1 , wherein said mixture of alkylaryl phosphites comprises

one or more tris(monoalkylaryl) phosphites in an amount from 37 to 54 weight percent

one or more bis(monoalkylaryl)dialkylaryl phosphites in an amount from 31 to 50 weight percent,

one or more bis(dialkylaryl)alkylaryl phosphites in an amount from 5 to 10 weight percent,

one or more tris(dialkylaryl) phosphites in an amount from 0.3 to 5 weight percent based on the total weight of all phosphites in the phosphite composition.

9. The composition of claim 8 , wherein R 8 and R 9 are selected from n-butyl, sec-butyl, t-butyl, n-amyl, sec-amyl, neo-amyl and t-amyl.

10. The composition of claim 9 , wherein R 8 is t-butyl and R 9 is t-amyl.

11. The composition of claim 10 , comprising from 0.01 to 5 weight percent of said free phenol.

12. The composition of claim 10 , comprising less than 1 weight percent of said free phenol.

13. The composition of claim 8 , comprising from 0.01 to 5 weight percent of said free phenol.

14. The composition of claim 8 , comprising less than 1 weight percent of said free phenol.

15. A stabilized polymer composition comprising a polymer and the phosphite composition of claim 1 .

16. The stabilized polymer composition according to claim 15 wherein the polymer comprises a polyolefin, polyalkylene terephthalate, polyphenylene ether, styrenic polymer, polycarbonate or ABS.

17. The stabilized polymer composition according to claim 16 wherein the polymer comprises a polyethylene, polypropylene, polyethylene terephthalate, polyphenylene ether or high impact polystyrene.

18. The stabilized polymer composition according to claim 17 wherein the polymer comprises a high density polyethylene, low density polyethylene or linear low density polyethylene.

Assignments (16)
RELEASE OF SECURITY INTEREST Recorded Dec 30, 2025
From: ALTER DOMUS (US) LLC, AS COLLATERAL AGENT
To: SI GROUP, INC.
Reel/Frame 074136/0039 →
ASSIGNMENT OF SECURITY INTEREST IN PATENTS [REEL 068968/FRAME 0001] Recorded Dec 24, 2024
From: JPMORGAN CHASE BANK, N.A.
To: ALTER DOMUS (US) LLC
Reel/Frame 069770/0736 →
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 →
SECURITY INTEREST Recorded Sep 19, 2024
From: SI GROUP, INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 068968/0001 →
SECURITY INTEREST Recorded Sep 19, 2024
From: SI GROUP, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 068968/0024 →
MERGER Recorded Feb 16, 2023
From: SI GROUP USA (USAA), LLC
To: SI GROUP, INC.
Reel/Frame 062719/0326 →
CORRECTIVE ASSIGNMENT TO CORRECT THE MERGER AND CHANGE OF NAME SHOULD BE CORRECTED TO CHANGE OF NAME PREVIOUSLY RECORDED ON REEL 050635 FRAME 0880. ASSIGNOR(S) HEREBY CONFIRMS THE AMENDED AND RESTATED CERTIFICATE OF FORMATION OF ADDIVANT USA LLC. Recorded Oct 22, 2019
From: ADDIVANT USA LLC
To: SI GROUP USA (USAA), LLC
Reel/Frame 050784/0361 →
MERGER AND CHANGE OF NAME Recorded Oct 3, 2019
From: ADDIVANT USA, LLC; SI GROUP USA (USAA), LLC
To: SI GROUP USA (USAA), LLC
Reel/Frame 050635/0880 →
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 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 →