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01/11/07 | 56 views | #20070010393 | Prev - Next | USPTO Class 502 | About this Page  502 rss/xml feed  monitor keywords

Alkoxylated phosphite ester and process therefor

USPTO Application #: 20070010393
Title: Alkoxylated phosphite ester and process therefor
Abstract: A composition and a process for producing the composition are disclosed. The composition comprises an alkoxylated phosphite ester which has the formula of (HO[{CH(R)}mO]n)3P in which each R can be the same or different and can be independently hydrogen or an alkyl group, or combinations of two or more thereof and m is a number from 2 to about 20 and n is a number from 2 to about 20. The process comprises contacting a trialkyl phosphite with an alkylene glycol or polyalkylene glycol to produce a mixture followed by heating the mixture. Also disclosed in a process for using the composition, which comprises contacting a carbonyl compound, in the presence of the composition, with an alcohol. (end of abstract)
Agent: E I Du Pont De Nemours And Company Legal Patent Records Center - Wilmington, DE, US
Inventor: Donald E. Putzig
USPTO Applicaton #: 20070010393 - Class: 502162000 (USPTO)
Related Patent Categories: Catalyst, Solid Sorbent, Or Support Therefor: Product Or Process Of Making, Catalyst Or Precursor Therefor, Organic Compound Containing, Organic Phosphorus Or Nitrogen, Except The Ammonium Ion
The Patent Description & Claims data below is from USPTO Patent Application 20070010393.
Brief Patent Description - Full Patent Description - Patent Application Claims  monitor keywords

FIELD OF INVENTION

[0001] This invention relates to a composition comprising an alkoxylated phosphite ester, to a process for producing the ester, and to a process for using the composition.

BACKGROUND OF THE INVENTION

[0002] Polyesters such as, for example, polyethylene terephthalate, polytrimethylene terephthalate and polybutylene terephthalate, are a class of important industrial polymers. They are widely used in thermoplastic fibers, films, and molding applications.

[0003] Polyesters can be produced by transesterification of a dialkyl terephthalate ester with a glycol followed by polycondensation or by direct esterification of terephthalic acid with the selected glycol followed by polycondensation.

[0004] Organic titanates, such as tetraisopropyl and tetra n-butyl titanates, are known to be effective catalysts for producing polyester and frequently are the catalyst of choice. However, these catalysts tend to generate a significant amount of yellow discoloration when used as polyesterification catalysts.

[0005] Therefore, there is an increasing need for developing a new composition that can be used as stabilizer for polyester and to reduce color formation of polyester.

SUMMARY OF THE INVENTION

[0006] A composition comprises an alkoxylated phosphite ester (or polyalkylene glycol phosphite ester) which has the formula of (HO[{CH(R)}.sub.mO].sub.n).sub.3P in which each R can be the same or different and can be independently hydrogen, an alkyl group, or combinations thereof, m is a number from 2 to about 20, n is a number from 1 to about 20.

[0007] A process comprises contacting a phosphite ester with a glycol or polyalkylene glycol under a condition effective to produce an alkoxylated phosphite ester.

[0008] A process, which can be used for producing polyester, comprises contacting a carbonyl compound, in the presence of the composition, with an alcohol to produce polyester.

[0009] Also provided is a process, which can be used for producing polyester. It comprises contacting a carbonyl compound, optionally in the presence of a catalyst, with an alcohol to produce a product comprising an oligomer and contacting the product with an alkoxylated phosphite ester in which the catalyst can be any esterification or transesterification or polycondensation catalyst.

DETAILED DESCRIPTION OF THE INVENTION

[0010] The composition of this invention can be substantially or completely soluble or a stable solution in a solvent such as, for example, water, an alcohol, or combinations thereof. The term "substantially" means more than trivial. However, a substantial portion of the composition can also be suspended or dispersed in the solvent. The term "stable solution" means a solution remains solution without substantial precipitation or suspension or dispersion of a solute at room temperature (about 25.degree. C.) for at least about 1 day, or 5 days, or even 10 days.

[0011] The composition is, or can comprise or consist essentially of or consist of an alkoxylated phosphite ester which has the formula of (HO[{CH(R)}.sub.mO].sub.n).sub.3P in which each R can be the same or different and can be independently hydrogen, an alkyl group having 1 to 10 carbon atoms per group, or combinations thereof, m is a number from 2 to about 20 or 2 to 10, n is a number from 1 to about 20 or 1 to about 10.

[0012] Examples of alkoxylated phosphite esters include, but are not limited to, tri-(ethylene glycol) phosphite, tri-(propylene glycol) phosphite, tri(isopropylene glycol) phosphite, tri-(butylene glycol) phosphite, tri-(isobutylene glycol) phosphite, tri-(pentylene glycol) phosphite, tri-(hexylene glycol) phosphite, tri-(nonylene glycol) phosphite, tri-(diethylene glycol) phosphite, tri-(triethylene glycol) phosphite, tri-(polyethylene glycol) phosphite, tri-(polypropylene glycol) phosphite, tri-(polybutylene glycol) phosphite or combinations of two or more thereof.

[0013] The composition can be produced by contacting a trialkylphosphite with an alkylene glycol or polyalkylene glycol under a condition effective to produce a product comprising an alkoxylated phosphite.

[0014] A trialkylphosphite having the formula of (R'O).sub.3P where R' is an alkyl group which can be substituted with a second alkyl group or aryl group. Examples of trialkylphosphites include, but are not limited to, trimethyl phosphite, triethyl phosphite, tripropyl phosphite, tributyl phosphite, triisobutyl phosphite, triamyl phosphite, trihexyl phosphite, trinonyl phosphite, or combinations of two or more thereof.

[0015] A glycol or polyalkylene glycol can have the formula (HO[{CH(R)}.sub.mO].sub.nH in which R, m, and n are the same as those disclosed above (if a polyalkylene glycol, m and n are each at least 2). Examples of alkylene glycols include, but are not limited to, ethylene glycol, propylene glycol, isopropylene glycol, 1,4-butylene glycol, 1,5-pentylene glycol, 1,6-hexylene glycol, 1,8-ocytlene glycol, 1,9-nonylene glycol, or combinations of two or more thereof. Examples of polyalkylene glycols include, but are not limited to diethylene glycol, triethylene glycol, polyethylene glycol, polypropylene glycol, polybutylene glycol, or combinations of two or more thereof.

[0016] The condition can include a temperature in the range of from about 30.degree. C. to about 250.degree. C., or about 50.degree. C. to about 200.degree. C., or about 75.degree. C. to about 150.degree. C. under a pressure that can accommodate the temperature for a period of time from about 0.01 to about 10, or 0.1 to about 5, or 0.1 to about 3 hours. Contacting under such condition produces a product comprising an alkoxylated phosphite.

[0017] The process can be carried out in the presence of a catalyst in an amount from about 0.0001 to about 5 weight % of trialkylphosphite. The catalyst can be any known catalyst for catalyzing the reaction of a phosphite and glycol. An example of catalyst is a tetraalkyl titanate, also referred to as titanium tetrahydrocarbyloxide. Examples of suitable tetraalkyl titanates include those having the general formula Ti(OR).sub.4 where each R is individually selected from an alkyl, cycloalkyl, alkaryl, hydrocarbyl radical containing from 1 to about 30, preferably 2 to about 18, and most preferably 2 to 12 carbon atoms per radical and each R can be the same or different. Tetraalkyl titanates in which the hydrocarboxyl group contains from 2 to about 12 carbon atoms per radical which is a linear or branched alkyl radical are relatively inexpensive, readily available, and effective in forming a solution. Suitable tetraalkyl titanates include, but are not limited to, titanium tetraethoxide, titanium tetrapropoxide, titanium tetraisopropoxide, titanium tetra-n-butoxide, titanium tetrahexoxide, titanium tetra 2-ethylhexoxide, titanium tetraoctoxide, and combinations of two or more thereof.

[0018] Suitable tetraalkyl titanates can be produced by any means known to one skilled in the art such as, for example, disclosed in U.S. Pat. No. 6,066,714, the entire disclosure of which is herein incorporated by references. Examples of commercially available tetraalkyl titanates include, but are not limited to, TYZOR.RTM. TPT and TYZOR.RTM. TBT (tetra isopropyl titanate and tetra n-butyl titanate, respectively) available from E. I. du Pont de Nemours and Company, Wilmington, Del., USA (DuPont).

[0019] Thereafter, the product comprising the alkoxylated phosphite can be further process by any means known to one skilled in the art to purify, or to recover, or to isolate the alkoxylated phosphite. The means include any known distillation techniques known to one skilled in the art such as, for example, a distillation under reduced pressure (vacuum distillation). The distillation can be carried out under a condition including a temperature in the range of from about 0.degree. C. to about 250.degree. C., or about 30.degree. C. to about 200.degree. C., or about 50.degree. C. to about 150.degree. C. under a pressure that can accommodate the temperature for a period of time from about 0.01 to about 10, or 0.1 to about 5, or 0.1 to about 3 hours.

[0020] The composition comprising the alkoxylated phosphite can also comprise or be produced from titanium or a titanium compound such as, for example, an organic titanium compound. An example of organic titanium compound can be tetraalkyl titanate as disclosed above.

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