IP Library Granted Patent US 8,008,385
Granted Patent B2
US 8,008,385 · App. 12/804,772 · Granted Aug 30, 2011

Solid alkylaryl phosphite compositions and methods for manufacturing same

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Quick Facts
Patent No.
US 8,008,385
App. No.
12/804,772
Granted
Aug 30, 2011
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(dialkylaryl)phosphite in an amount from 20 to 93 weight percent; and at least one of: a bis(dialkylaryl)monoalkylaryl phosphite; a bis(monoalkylaryl)dialkylaryl phosphite; and a tris(monoalkylaryl)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 (32)

1. A composition comprising a phosphite composition, which phosphite composition consists of:

(a) from 25 to 80 weight percent of a tris(dialkylaryl)phosphite;

(b) from 15 to 50 weight percent of a bis(dialkylaryl)monoalkylaryl phosphite;

(c) from 3 to 25 weight percent of a bis(monoalkylaryl)dialkylaryl phosphite;

(d) from 0.1 to 6 weight percent of a tris(monoalkylaryl)phosphite;

(e) from 0 to 5 weight percent other phosphites

wherein dialkylaryl in (a), (b), (c) and (d) is dibutylphenyl or diamylphenyl and monoalkaryl in (a), (b), (c) and (d) is butylphenyl or amylphenyl,

weight percent is based on the total weight of all phosphites in the phosphite composition,

and wherein the phosphite composition is a solid at ambient conditions melting in a temperature range of from greater than 30° C. to less than 170° C.

2. The composition of claim 1 , wherein the phosphite composition contains from 0.1 to 5% weight percent other phosphites selected from the group consisting of phosphites containing trialkylaryl moieties and phosphites containing unsubstituted aryl moieties.

3. The composition of claim 2 , wherein the phosphite composition contains 0.1 to 4 weight percent of trialkyl aryl moieties.

4. The composition of claim 1 , wherein the phosphite composition comprises components (a) and (b) in combination in an amount greater than 74 weight percent, based on the total weight of all phosphites in the phosphite composition.

5. The composition of claim 1 , wherein at least 55 weight percent of all dialkylaryl and monoalkaryl moieties in the phosphite composition are phenyl substituted with alkyl groups in both the ortho-position and the para-position.

6. The composition of claim 1 , wherein dialkylaryl in (a), (b), (c) and (d) is di-t-butylphenyl and monoalkaryl in (a), (b), (c) and (d) is t-butylphenyl.

7. The composition of claim 1 , wherein dialkylaryl in (a), (b), (c) and (d) is di-t-amylphenyl and monoalkaryl in (a), (b), (c) and (d) is t-amylphenyl.

8. A phosphite composition prepared by reacting a phosphorus halide with an alkylated phenol composition comprising a monoalkylphenol in an amount from 2 to 45 weight percent, and

a dialkylphenol in an amount from 55 to 98 weight percent, based on the total weight of all alkylated phenols in the alkylated phenol composition,

wherein alkyl moieties on the monoalkylphenol and the dialkylphenol are selected from the group consisting of isomers of butyl and amyl

and the phosphite composition which is prepared comprises:

(a) a tris(dialkylaryl)phosphite in an amount from 20 to 93 weight percent;

and at least one of:

(b) a bis(dialkylaryl)monoalkylaryl phosphite;

(c) a bis(monoalkylaryl)dialkylaryl phosphite; and

(d) a tris(monoalkylaryl)phosphite,

wherein the composition comprises components (b), (c) and (d) in combination in an amount from 7 to 80 weight percent, based on the total weight of all phosphites in the composition, which composition comprises 0 to 5 weight percent other phosphites,

and wherein a composition consisting of (a), at least one of (b), (c) and (d) and between 0 to 5 weight percent other phosphites is a solid at ambient conditions melting in a temperature range of from greater than 30° C. to less than 170° C.

9. The phosphite composition of claim 8 wherein the alkylated phenol composition is prepared by contacting one or more butene or pentene olefins with a phenol in the presence of a catalyst and under conditions effective to form the alkylate composition, wherein the molar ratio of the one or more olefins to the phenol is from 1.25:1 to 3:1.

10. The phosphite composition of claim 8 wherein the alkylated phenol composition comprises a dialkylphenol in an amount ranging from 60 to 95 weight percent and a monoalkylphenol in an amount ranging from 5 to 40 weight percent based on total weight of all alkylated phenols in the alkylated phenol composition.

11. The phosphite composition of claim 9 , wherein at least 50 weight percent of alkyl moieties in the alkylated phenol composition are t-butyl.

12. The phosphite composition of claim 9 , wherein at least 50 weight percent of alkyl moieties in the alkylated phenol composition are tert-amyl.

13. A composition according to claim 1 further comprising a polymer.

14. The composition of claim 1 , wherein at least 55 weight percent of aryl moieties comprised by the phosphites are substituted with alkyl groups in both the ortho-position and the para-position, at least 10 weight percent are monosubstituted in the para-position, 0.1 to 3 weight percent are tri-substituted and 0.1 to 3 weight percent are mono-substituted in the ortho position.

Assignments (11)
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 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 →
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 →