IP Library Granted Patent US 8,309,635
Granted Patent B2
US 8,309,635 · App. 12/804,681 · Granted Nov 13, 2012

Solid alkylaryl phosphite compositions and methods for manufacturing same

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Quick Facts
Patent No.
US 8,309,635
App. No.
12/804,681
Granted
Nov 13, 2012
Kind
B2
Abstract

The invention is directed to various alkylaryl phosphite compositions that ideally are suitable for use as secondary antioxidants in polymers. In one aspect, the phosphite composition comprises a tris(monoalkylaryl)phosphite in an amount from 51 to 95 weight percent; and at least one of: a bis(monoalkylaryl)dialkylaryl phosphite; a bis(dialkylaryl)monoalkylaryl phosphite; and a tris(dialkylaryl)phosphite. The inventive phosphite composition is a solid at ambient conditions. The invention also relates to alkylate compositions and processes for forming such alkylate compositions and such phosphite compositions.

Claims (39)

1. A phosphite composition, comprising:

(a) tris(4-t-butylphenyl)phosphite or tris(4-t-amylphenyl) phosphite in an amount from 51 to 95 weight percent; and

at least one of:

(b) bis(4-t-butylphenyl)(2,4-di-t-butylphenyl) phosphite or bis(4-t-amylphenyl)(2,4-di-t-butylamylphenyl)phosphite;

(c) bis(2,4-di-t-butylphenyl)(4-t-butylphenyl) phosphite or bis(2,4-di-t-amylphenyl)(4-t-butylamylphenyl)phosphite; or

(d) tris(2,4-di-t-butylphenyl)phosphite or tris(2,4-di-t-amylphenyl)phosphite,

wherein the composition comprises components (b), (c) and (d) in combination in an amount from 5 to 49 weight percent, based on the total weight of all phosphites in the composition, and wherein the composition is a solid at ambient conditions with a melting range greater than 25° C.

2. The phosphite composition according to claim 1 , comprising (a) and at least one of (c) or (d).

3. The phosphite composition according to claim 1 , comprising (a) and (d).

4. The phosphite composition according to claim 1 , further comprising an amine of formula V:

wherein x is 1, 2 or 3; R 8 is selected from the group consisting of hydrogen, and straight or branched C 1-6 alkyl, and R 9 is selected from the group consisting of straight or branched C 1 -C 30 alkyl.

5. The phosphite composition according to claim 1 , wherein the phosphite composition has a phosphorous content of from 5.5 to 6.5 mol %.

6. A phosphite composition according to claim 5 comprising:

(a) tris(4-t-butylphenyl)phosphite in an amount from 51 to 95 weight percent; and

at least one of:

(b) bis(4-t-butylphenyl)(2,4-di-t-butylphenyl)phosphite;

(c) bis(2,4-di-t-butylphenyl)(4-t-butylphenyl)phosphite; or

(d) tris(2,4-di-t-butylphenyl)phosphite.

7. A phosphite composition according to claim 5 comprising:

(a) tris(4-di-t-amylphenyl)phosphite in an amount from 51 to 95 weight percent; and

at least one of:

(b) bis(4-t-amylphenyl)(2,4-di-t-butylamylphenyl)phosphite;

(c) bis(2,4-di-t-amylphenyl)(4-t-butylamylphenyl)phosphite; or

(d) tris(2,4-di-t-amylphenyl)phosphite.

8. A stabilized polymeric composition, comprising:

(a) a polymer; and

(b) the phosphite composition of claim 1 .

9. The stabilized polymeric composition according to claim 8 wherein the polymer comprises a polyolefin homopolymer, polyolefin copolymer, rubber, polyester, polyurethane, polyalkylene terephthalate, polysulfone, polyimide, polyphenylene ether, styrenic polymer, styrenic copolymer, polycarbonate, acrylic polymer, polyamide, polyacetal, halide-containing polymer or biodegradable polymer, or a blend thereof, and wherein the phosphite composition is present in an amount of from 0.001 to 5 wt % based on the total weight of the polymer composition.

10. The stabilized polymeric composition according to claim 9 wherein the polymer comprises a polyolefin homopolymer, polyolefin copolymer, polyester, polyurethane, polyalkylene terephthalate, styrenic polymer, styrenic copolymer, polycarbonate, acrylic polymer, polyamide, polyacetal, halide-containing polymer.

11. The stabilized polymeric composition according to claim 9 wherein the phosphite composition comprises tris(4-t-butylphenyl)phosphite and at least one of bis(4-t-butylphenyl)(2,4-di-t-butylphenyl)phosphite; bis(2,4-di-t-butylphenyl)(4-t-butylphenyl)phosphite; or tris(2,4-di-t-butylphenyl)phosphite.

12. The stabilized polymeric composition according to claim 9 wherein the phosphite composition comprises tris(4-t-butylphenyl)phosphite and at least one of bis(2,4-di-t-butylphenyl)(4-t-butylphenyl)phosphite; or tris(2,4-di-t-butylphenyl)phosphite.

13. The stabilized polymeric composition according to claim 9 wherein the phosphite composition comprises tris(4-t-butylphenyl)phosphite and tris(2,4-di-t-butylphenyl)phosphite.

14. The stabilized polymeric composition according to claim 9 wherein the phosphite composition comprises tris(4-t-amylphenyl)phosphite and at least one of bis(4-t-amylphenyl)(2,4-di-t-amylphenyl)phosphite; bis(2,4-di-t-amylphenyl)(4-t-amylphenyl)phosphite; or tris(2,4-di-t-amylphenyl)phosphite.

15. The stabilized polymeric composition according to claim 9 wherein the phosphite composition comprises tris(4-t-amylphenyl)phosphite and at least one of bis(2,4-di-t-amylphenyl)(4-t-amylphenyl)phosphite; or tris(2,4-di-t-amylphenyl)phosphite.

16. The stabilized polymeric composition according to claim 9 wherein the phosphite composition comprises tris(4-t-amylphenyl)phosphite and tris(2,4-di-t-amylphenyl)phosphite.

17. The stabilized polymeric composition according to claim 9 wherein the polymer comprises a blend comprising a polyphenylene ether, polystyrene, polyvinyl chloride.

18. The stabilized polymeric composition according to claim 17 wherein the polymer comprises ABS, methacrylonitrile/ABS, α-methylstyrene/ABS, polyester/ABS or polycarbonate/ABS.

19. The stabilized polymeric composition according to claim 17 wherein the polymer comprises a thermoplastic polymer comprising a polyolefin homopolymer, polyolefin copolymer, polycarbonate, polyester, polyphenylene ether, polystyrene homo polymer, or polystyrene copolymer.

20. The stabilized polymeric composition according to claim 19 wherein the polymer comprises a polyolefin homopolymer, polyolefin copolymer, polystyrene homo polymer, or polystyrene copolymer.

Assignments (20)
RELEASE OF SECURITY INTEREST Recorded Dec 30, 2025
From: ALTER DOMUS (US) LLC, AS COLLATERAL AGENT
To: SI GROUP, INC.
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RELEASE OF SECURITY INTEREST Recorded Nov 1, 2024
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To: SI GROUP, INC.; ADDIVANT USA, LLC; SI GROUP USA (USAA), LLC (F/K/A ADDIVANT USA, LLC)
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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 →
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
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To: ADDIVANT USA, LLC
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RELEASE OF SECURITY INTEREST RECORDED AT REEL 037207 FRAME 0959 Recorded Oct 16, 2018
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Reel/Frame 047775/0963 →
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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
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RELEASE OF SECOND LIEN INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded May 11, 2017
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PATENT SECURITY AGREEMENT Recorded Dec 3, 2015
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SECURITY INTEREST Recorded Jul 19, 2013
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PARTIAL RELEASE OF IP SECURITY AGREEMENT TL Recorded May 8, 2013
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