Polyesters including isosorbide as a comonomer and methods for making same

A technology of isosorbide and monomer polymerization, which is applied in the fields of polyester and polyester preparation, and can solve the problems of no preparation, low maximum molecular weight, etc.

Inactive Publication Date: 2001-06-06
EI DU PONT DE NEMOURS & CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the highest molecular weight reported is still relatively low, i.e. 400-10,000, and no polyester actually containing 1,4:3,6-dianhydrosorbitan moieties has been produced

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] The following polymerization reactants were added to a 4 liter polymerization flask equipped with an air-cooled jacketed Vigreux column, a mechanical stirrer and a water-cooled condenser: dimethyl terephthalate (780.133 g), isosorbide (70.531 g ) and ethylene glycol (531.211g). The molar ratio of the reactants is correspondingly 1:0.12:2.13. A catalyst was also added consisting of manganese (II) acetate tetrahydrate (0.296 g), cobalt (II) acetate tetrahydrate (0.214 g) and antimony (III) oxide (0.350 g). This corresponds to 85 ppm manganese (weight of metal as a weight percent of dimethyl terephthalate), 65 ppm cobalt and 375 ppm antimony. The flask was purged with a stream of nitrogen while the temperature was raised to 150°C over 1 hour using a fluidized sand bath as the heating medium. At this point, the nitrogen purge was stopped and methanol evolution began. Methanol was continuously collected as the reaction was further heated to 250°C over about 2 hours. Note...

Embodiment 2

[0065] The following monomers were charged to a 5 gallon reactor: 8,638.9 g terephthalic acid; 911.9 g isosorbide and 3,808.5 g ethylene glycol. The molar ratio of the reactants is correspondingly 1:0.12:1.18. The following catalyst components were also added at this time: 1.825 g of cobalt(II) acetate tetrahydrate and 3.103 g of antimony(III) oxide. The amount of catalyst corresponds to 50 ppm cobalt and 275 ppm antimony (expressed as weight of metal compared to weight of terephthalic acid). The polymerization reactor is equipped with fractionation column and stirrer. The reactor was purged with nitrogen and then sealed under 50 psig nitrogen pressure. The temperature was raised to 265°C over about 5 hours while the reaction was stirred. During this time, the pressure was raised to 70 psig as the esterification reaction proceeded. At the end of this period, the release pressure returns to 50 psig. Water and ethylene glycol were distilled off from the reactor. The temper...

Embodiment 3

[0069] Purified terephthalic acid (7.48 kg), isosorbide (3.55 kg) and ethylene glycol (1.70 kg) were placed in a stainless steel stirred reactor preheated to 70°C under an atmospheric pressure nitrogen purge. The reactor was equipped with a packed distillation column. The monomer composition corresponds to a molar ratio of terephthalic acid:ethylene glycol:isosorbide of 1:0.61:0.54. The reactor was heated to 285°C over 3 hours and the reaction mixture was maintained at a positive pressure of 50-60 psi. During this time, a distillate, mainly water, was collected from the packed column. After the melting temperature reached at least 275° C. and the terephthalic acid was substantially consumed (as determined by the clarity of the reaction mixture), the pressure was released and germanium(IV) oxide catalyst (3.77 g) was added as a solution in ethylene glycol (Ethylene Glycol). 0.100N GeO in Diol 2 ). The reaction mixture was stirred for an additional 20 minutes. The pressure ...

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Abstract

This invention relates to an isotropic polyester polymer and method for making the polyester is prepared by (1) combining in a reactor a monomer containing a terephthaloyl moiety; optionally, one or more other monomers containing an aromatic diacid moiety; a monomer comprising an ethylene glycol moiety; a monomer containing an isosorbide moiety; optionally, one or more other monomers containing a diol moiety; and optionally, a monomer containing a diethylene glycol moiety; with a condensation catalyst suitable for condensing aromatic diacids and glycols; and (2) heating the monomers and catalyst to polymerize the monomers to yield a polyester having an inherent viscosity of at least about 0.35 dL/g.

Description

field of invention [0001] This application relates to polyesters and methods of making polyesters, and more particularly to polyesters containing isosorbide moieties and methods of making them. Background of the invention [0002] The diol 1,4:3,6-dianhydro-D-sorbitol (hereinafter referred to as isosorbide, whose structure is illustrated below) is readily prepared from renewable resources such as sugars and starches. For example, isosorbide can be prepared from D-glucose by hydrogenation followed by acid-catalyzed dehydration. [0003] Isosorbide has been incorporated as a monomer into polyesters that also include terephthaloyl moieties. See eg R. Storbeck et al. Makromol. Chem., Vol. 194, pp. 53-64 (1993); R. Storbeck et al. Polymer, Vol. 34, pp. 5003 (1993). However, secondary alcohols such as isosorbide are generally believed to have poor reactivity and are susceptible to acid catalyzed reactions. See eg D. Braun et al. J. Prakt. Chem., Vol. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G63/199C08G63/672C08G63/78C08G63/80
CPCC08G63/672C08G63/80C08G63/00C08G63/02
Inventor L·F·查邦尼奥R·E·约翰森H·B·维特勒G·克哈纳里安
Owner EI DU PONT DE NEMOURS & CO
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