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Polyester compositions comprising minimal amounts of cyclobutanediol

a technology of cyclobutanediol and composition, which is applied in the field of polymer compositions, can solve the problems of insufficient equipment used in the industry to manufacture or post-polymerization process these materials, and the difficulty of forming amorphous articles by methods known in the art such as extrusion, injection molding, etc., and achieves the effect of low crystallinity

Inactive Publication Date: 2006-12-21
CRAWFORD EMMETT DUDLEY +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0072] In one aspect, the polyesters useful in the invention contain at least one branching agent without regard to the method or sequence in which it is added.
[0073] In one aspect, the polyesters useful in the invention are made from no 1,3-propanediol, or, 1,4-butanediol, either singly or in combination. In other aspects, 1,3-propanediol or 1,4-butanediol, either singly or in combination, may be used in the making of the polyesters useful in this invention.
[0074] In one aspect of the invention, the mole % of cis-2,2,4,4-tetramethyl-1,3-cyclobutanediol useful in certain polyesters useful in the invention is greater than 50 mole % or greater than 55 mole % of cis-2,2,4,4-tetramethyl-1,3-cyclobutanediol or greater than 70 mole % of cis-2,2,4,4-tetramethyl-1,3-cyclobutanediol; wherein the total mole percentage of cis-2,2,4,4-tetramethyl-1,3-cyclobutanediol and trans-2,2,4,4-tetramethyl-1,3-cyclobutanediol is equal to a total of 100 mole %.
[0075] In one aspect of the invention, the mole % of the isomers of 2,2,4,4-tetramethyl-1,3-cyclobutanediol useful in certain polyesters useful in the invention is from 30 to 70 mole % of cis-2,2,4,4-tetramethyl-1,3-cyclobutanediol or from 30 to 70 mole % of trans-2,2,4,4-t

Problems solved by technology

This polyester crystallizes rapidly upon cooling from the melt, making it very difficult to form amorphous articles by methods known in the art such as extrusion, injection molding, and the like.
While these copolyesters are useful in many end-use applications, they exhibit deficiencies in properties such as glass transition temperature and impact strength when sufficient modifying ethylene glycol is included in the formulation to provide for long crystallization half-times. For example, copolyesters made from terephthalic acid, 1,4-cyclohexanedimethanol, and ethylene glycol with sufficiently long crystallization half-times can provide amorphous products that exhibit what is believed to be undesirably higher ductile-to-brittle transition temperatures and lower glass transition temperatures than the compositions revealed herein.
Generally, however, these polymers exhibit high inherent and / or intrinsic viscosities, high melt viscosities and / or high Tgs (glass transition temperatures) such that the equipment used in industry can be insufficient to manufacture or post polymerization process these materials.
Also, compositions containing higher amounts of 2,2,4,4-tetramethyl-1,3-cyclobutanediol are not useful for many end use applications for example, certain types of bottles and / or containers because of the high glass transition temperature and / or because of the low crystallininity or no crystallinity of such polyesters.

Method used

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  • Polyester compositions comprising minimal amounts of cyclobutanediol
  • Polyester compositions comprising minimal amounts of cyclobutanediol
  • Polyester compositions comprising minimal amounts of cyclobutanediol

Examples

Experimental program
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Effect test

example 1

[0192] This example illustrates that 2,2,4,4-tetramethyl-1,3-cyclobutanediol is more effective at reducing the crystallization rate of PCT than ethylene glycol or isophthalic acid. In addition, this example illustrates the benefits of 2,2,4,4-tetramethyl-1,3-cyclobutanediol on the glass transition temperature and density.

[0193] A variety of copolyesters were prepared as described below. These copolyesters were all made with 200 ppm dibutyl tin oxide as the catalyst in order to minimize the effect of catalyst type and concentration on nucleation during crystallization studies. The cis / trans ratio of the 1,4-cyclohexanedimethanol was 31 / 69 while the cis / trans ratio of the 2,2,4,4-tetramethyl-1,3-cyclobutanediol is reported in Table 1.

[0194] For purposes of this example, the samples had sufficiently similar inherent viscosities thereby effectively eliminating this as a variable in the crystallization rate measurements.

[0195] Crystallization half-time measurements from the melt were ...

example 1a

[0199] This example illustrates the preparation of a copolyester with a target composition of 80 mol % dimethyl terephthalate residues, 20 mol % dimethyl isophthalate residues, and 100 mol % 1,4-cyclohexanedimethanol residues (28 / 72 cis / trans).

[0200] A mixture of 56.63 g of dimethyl terephthalate, 55.2 g of 1,4-cyclohexanedimethanol, 14.16 g of dimethyl isophthalate, and 0.0419 g of dibutyl tin oxide was placed in a 500-milliliter flask equipped with an inlet for nitrogen, a metal stirrer, and a short distillation column. The flask was placed in a Wood's metal bath already heated to 210° C. The stirring speed was set to 200 RPM throughout the experiment. The contents of the flask were heated at 210° C. for 5 minutes and then the temperature was gradually increased to 290° C. over 30 minutes. The reaction mixture was held at 290° C. for 60 minutes and then vacuum was gradually applied over the next 5 minutes until the pressure inside the flask reached 100 mm of Hg. The pressure insi...

example 1b

[0201] This example illustrates the preparation of a copolyester with a target composition of 100 mol % dimethyl terephthalate residues, 20 mol % ethylene glycol residues, and 80 mol % 1,4-cyclohexanedimethanol residues (32 / 68 cis / trans).

[0202] A mixture of 77.68 g of dimethyl terephthalate, 50.77 g of 1,4-cyclohexanedimethanol, 27.81 g of ethylene glycol, and 0.0433 g of dibutyl tin oxide was placed in a 500-milliliter flask equipped with an inlet for nitrogen, a metal stirrer, and a short distillation column. The flask was placed in a Wood's metal bath already heated to 200° C. The stirring speed was set to 200 RPM throughout the experiment. The contents of the flask were heated at 200° C. for 60 minutes and then the temperature was gradually increased to 210° C. over 5 minutes. The reaction mixture was held at 210° C. for 120 minutes and then heated up to 280° C. in 30 minutes. Once at 280° C., vacuum was gradually applied over the next 5 minutes until the pressure inside the fl...

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Abstract

Described are polyester compositions comprising (a) a dicarboxylic acid component comprising terephthalic acid residues; optionally, aromatic dicarboxylic acid or aliphatic dicarboxylic acid residues; minimal amounts of 2,2,4,4-tetramethyl-1,3-cyclobutanediol residues; ethylene glycol, and optionally, 1,4-cyclohexanedimethanol residues.

Description

CROSS-REFERENCES TO RELATED APPLICATIONS [0001] This application claims priority under 35 U.S.C. § 119(e) to U.S. Provisional Application Ser. No. 60 / 691,567 filed on Jun. 17, 2005, U.S. Provisional Application Ser. No. 60 / 731,454 filed on Oct. 28, 2005, U.S. Provisional Application Ser. No. 60 / 731,389, filed on Oct. 28, 2005, U.S. Provisional Application Ser. No. 60 / 739,058, filed on Nov. 22, 2005, and U.S. Provisional Application Ser. No. 60 / 738,869, filed on Nov. 22, 2005, U.S. Provisional Application Ser. No. 60 / 750,692 filed on Dec. 15, 2005, U.S. Provisional Application Ser. No. 60 / 750,693, filed on Dec. 15, 2005, U.S. Provisional Application Ser. No. 60 / 750,682, filed on Dec. 15, 2005, and U.S. Provisional Application Ser. No. 60 / 750,547, filed on Dec. 15, 2005, all of which are hereby incorporated by this reference in their entireties.FIELD OF THE INVENTION [0002] The present invention generally relates to polyester compositions comprising a polyester composition made from t...

Claims

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Application Information

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IPC IPC(8): C08G63/16
CPCA01G9/1438Y10T428/24942A61J17/00A61M1/16B01D61/30B29B2911/14986B29C49/00B29K2067/00B29L2031/7542B32B17/10018B32B27/36B65D1/0207C08G63/199C08J5/18C08J7/047C08J7/123C08J2367/00C08J2367/02C08J2483/00C08K3/32C08K5/521C08K2201/014C08L67/02C08L69/00C08L101/00E01F8/0005E04D13/03G02B1/105G02B5/3083G02F1/133606A47F5/00Y10T428/24479Y10T428/24107Y10T428/162Y10T428/161Y10T428/1352Y10T428/139Y10T428/1397B65D43/00B65D25/00B65D23/10C08L2666/02C08L2666/18C08L67/00Y10T428/31507Y10T428/31786Y10T428/31663Y10T428/31504G02B1/10G02B1/14Y02A40/25B29C49/0005C08G63/183G02B1/04C08L67/03C08J7/0427C09D167/02
Inventor CRAWFORD, EMMETT DUDLEYPORTER, DAVID SCOTTCONNELL, GARY WAYNE
Owner CRAWFORD EMMETT DUDLEY
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