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US4223124A Expired / Lapsed US ⏱️ 0.0 years remaining

Method for producing polyesters containing low amounts of ether by-products

Assignee: Shell USA Inc
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Filing: 1979-06-22
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Granted: 1980-09-16
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Expires: 1999-06-22
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Abstract

Abstract A method for decreasing the amount of ether as a by-product in polyesters (for example terephthalic-based) by initially utilizing a deficient amount of a glycol (for example, ethylene glycol) in the early reaction stages and utilizing an excess of the glycol in the final or end stages. The polyesters produced are of better quality, have a high melting point, possess increased thermal stability, and yield improved fiber properties.

Inventors

  • 👤 Roy M. Broughton
  • 👤 Joseph R. Thomas
  • 👤 Terence E. Winters

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-03 08:40
CPC Classifications
C; C08; C08G; C08G63/00; C08G63/78; C08G63/81

Claims Analysis

Total Claims: 25
Claim 1
Independent Claim 158 words
A process for reducing the glycol ether content formed during the esterification reaction in making a polyester, comprising the steps of: adding to a heel solution in a vessel a dicarboxylic acid selected from the class consisting of alkyl dicarboxylic acids having from 2 to 16 carbon atoms, aryl dicarboxylic acids containing from 8 to about 16 carbon atoms, and alkyl substituted aryl dicarboxylic acids containing from 8 to about 16 carbon atoms; conducting an esterification reaction by adding a glycol containing from 2 to 12 carbon atoms and heating said vessel to a temperature of from about 20° C. below the boiling point to about 100° C. above the boiling point of said glycol; adding during the initial portion of said esterification reaction a deficient equivalent weight amount of said glycol so that an esterified acid solution having a low ether content is produced; and retaining a portion of said esterfied acid solution as a heel solution.
Claim 2
Dependent Claim 158 words
A process for reducing the glycol ether content formed during the esterification reaction in making a polyester, comprising the steps of: adding to a heel solution in a vessel a dicarboxylic acid selected from the class consisting of alkyl dicarboxylic acids having from 2 to 16 carbon atoms, aryl dicarboxylic acids containing from 8 to about 16 carbon atoms, and alkyl substituted aryl dicarboxylic acids containing from 8 to about 16 carbon atoms; conducting an esterification reaction by adding a glycol containing from 2 to 12 carbon atoms and heating said vessel to a temperature of from about 20° C. below the boiling point to about 100° C. above the boiling point of said glycol; adding during the initial portion of said esterification reaction a deficient equivalent weight amount of said glycol so that an esterified acid solution having a low ether content is produced; and retaining a portion of said esterfied acid solution as a heel solution.
Claim 3
Dependent Claim 21 words
A process according to claim 1 including pressurizing said vessel from atmospheric pressure to about 100 psi within an inert gas.
Claim 4
Dependent Claim 36 words
A process according to claim 2, wherein the total amount of said glycol added during said entire esterification reaction ranges from about 0.8 to about 1.5 weight equivalents based upon the amount of said dicarboxylic acid.
Claim 5
Dependent Claim 31 words
A process according to claim 3, wherein said deficient amount of said glycol is an equivalent ratio of said glycol to said dicarboxylic acid ranging from 0 to 1.2 weight equivalents.
Claim 6
Dependent Claim 46 words
A process according to claim 4, including adding said glycol in incremental amounts to said dicarboxylic acid, and wherein the overall ratio of said heel to said glycol and dicarboxylic acid added during said entire esterification reaction ranges from about 0.8 to about 1.6 weight equivalents.
Claim 7
Dependent Claim 17 words
A process according to claim 5, wherein the number of incremental additions ranges from 2 to infinity.
Claim 8
Dependent Claim 23 words
A process according to claim 6, including adding an equivalent weight excess of said glycol in the later stages of said esterification reaction.
Claim 9
Dependent Claim 22 words
A process according to claim 7, wherein said deficient equivalent weight amount of said glycol added initially is from 0.5 to 1.0.
Claim 10
Dependent Claim 65 words
A process according to claim 7 or 8, wherein said inert gas is selected from the class consisting of nitrogen, helium, argon, and carbon dioxide, wherein said temperature range of said esterification reaction ranges from about the boiling point to about 90° C. above the boiling point of said glycol, and wherein the pressure of said vessel ranges from about 25 to about 80 psi.
Claim 11
Dependent Claim 31 words
A process according to claim 5 or 8, wherein said dicarboxylic acid is terephthalic acid, and wherein said glycol is selected from the class consisting of ethylene glycol, and 1,4-butane diol.
Claim 12
Dependent Claim 23 words
A process according to claim 10, wherein said glycol-dicarboxylic acid equivalent weight ratio for said entire esterification reaction ranges from 0.9 to 1.4.
Claim 13
Dependent Claim 23 words
A process according to claim 11, wherein said glycol-acid equivalent weight ratio for said entire esterification reaction ranges from 1.15 to about 1.25.
Claim 14
Dependent Claim 180 words
A polyester having low glycol ether content produced according to a reaction comprising the steps of: adding to a heel solution in a vessel a dicarboxylic acid selected from the class consisting of alkyl dicarboxylic acids having from 2 to 16 carbon atoms, aryl dicarboxylic acids containing from 8 to 16 carbon atoms, and alkyl substituted aryl dicarboxylic acids containing from 8 to about 16 carbon atoms; conducting an esterification reaction by adding a glycol containing from 2 to 12 carbon atoms and heating said vessel to a temperature of from about 20° C. below the boiling point to about 100° C. above the boiling point of said glycol; adding during the initial esterification reaction a deficient equivalent weight amount of said glycol so that an esterfied acid having a low ether content is produced; retaining a portion of said esterfied acid solution as a heel solution; removing the remaining portion of said esterfied acid solution; and condensing said remaining esterfied acid solution by drawing a vacuum and adding a catalyst to produce a polyester having a low ether content.
Claim 15
Dependent Claim 180 words
A polyester having low glycol ether content produced according to a reaction comprising the steps of: adding to a heel solution in a vessel a dicarboxylic acid selected from the class consisting of alkyl dicarboxylic acids having from 2 to 16 carbon atoms, aryl dicarboxylic acids containing from 8 to 16 carbon atoms, and alkyl substituted aryl dicarboxylic acids containing from 8 to about 16 carbon atoms; conducting an esterification reaction by adding a glycol containing from 2 to 12 carbon atoms and heating said vessel to a temperature of from about 20° C. below the boiling point to about 100° C. above the boiling point of said glycol; adding during the initial esterification reaction a deficient equivalent weight amount of said glycol so that an esterfied acid having a low ether content is produced; retaining a portion of said esterfied acid solution as a heel solution; removing the remaining portion of said esterfied acid solution; and condensing said remaining esterfied acid solution by drawing a vacuum and adding a catalyst to produce a polyester having a low ether content.
Claim 16
Dependent Claim 42 words
A product according to claim 13, including pressurizing said vessel during said esterification reaction from atmospheric pressure to about 100 psi with an inert gas, and heating said condensation stage to a temperature of from about 180° C. to about 290° C.
Claim 17
Dependent Claim 77 words
A product according to claim 14, wherein the total amount of said glycol added during said entire esterification reaction ranges from about 0.8 to about 1.5 weight equivalents based upon the amount of said dicarboxylic acid, wherein said deficient amount of said glycol is an equivalent ratio of said glycol to said dicarboxylic acid ranging from 0 to 1.2 weight equivalents, and wherein said vacuum applied during said condensation step is less than 5 millimeters of mercury.
Claim 18
Dependent Claim 17 words
A product according to claim 15, including adding said glycol in incremental amounts to said dicarboxylic acid.
Claim 19
Dependent Claim 20 words
A product according to claim 16, wherein the number of incremental additions of said glycol ranges from 2 to infinity.
Claim 20
Dependent Claim 23 words
A product according to claim 17, including adding an equivalent weight excess of said glycol to the latter stages of said esterification reaction.
Claim 21
Dependent Claim 22 words
A product according to claim 18, wherein said deficient equivalent weight amount of said glycol added initially is from 0.5 to 1.0.
Claim 22
Dependent Claim 87 words
A product according to claim 18 or 19, wherein said inert gas is selected from the class consisting of nitrogen, helium, argon, and carbon dioxide, and wherein the temperature range of said esterification reaction ranges from about the boiling point to about 90° C. above the boiling point of said glycol, wherein the pressure of said vessel ranges from about 25 psi to about 80 psi, and wherein said condensation catalyst is selected from the class consisting of antimony, iron, titanium, zinc, cobalt, lead, manganese, and niobium.
Claim 23
Dependent Claim 31 words
A product according to claim 16 or 18, wherein said dicarboxylic acid is terephthalic acid, and wherein said glycol is selected from the class consisting of ethylene glycol and 1,4-butane diol.
Claim 24
Dependent Claim 23 words
A product according to claim 20, wherein said glycol-dicarboxylic acid equivalent weight ratio for said entire esterification reaction ranges from 0.9 to 1.4.
Claim 25
Dependent Claim 24 words
A product according to claim 22, wherein said glycol-acid equivalent weight ratio for said entire esterification reaction ranges from about 1.5 to about 1.25.

References Cited (Backward Citations)

US3427287A Cited
US4020049A Cited
US4165420A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1983-09-16 1984-03-17 1984-09-16 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-09-16 1988-03-17 1988-09-16 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-09-16 1992-03-17 1992-09-16 $7700.00 Window Closed / Lapsed

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