Opththalmic devices comprising polyester compositions formed from 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 1,4-cyclohexanedimethanol

Inactive Publication Date: 2006-12-21
EASTMAN CHEM CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0009] It is believed that certain ophthalmic products comprising polyester compositions formed from terephthalic acid, an ester thereof, or mixtures thereof, 1,4-cyclohexanedimethanol and 2,2,4,4-tetramethyl-1,3-cyclobutanediol with certain monomer compositions, inherent viscosities and/or glass transition temperatures are superior to polyesters known in the art and to polycarbonate with res

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 tha

Method used

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  • Opththalmic devices comprising polyester compositions formed from 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 1,4-cyclohexanedimethanol
  • Opththalmic devices comprising polyester compositions formed from 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 1,4-cyclohexanedimethanol
  • Opththalmic devices comprising polyester compositions formed from 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 1,4-cyclohexanedimethanol

Examples

Experimental program
Comparison scheme
Effect test

Example

Example 1

[0216] 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.

[0217] 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.

[0218] For purposes of this example, the samples had sufficiently similar inherent viscosities thereby effectively eliminating this as a variable in the crystallization rate measurements.

[0219] Crystallization half-time measurements from the ...

Example

3A film was pressed from the ground polyester of Example 1G at 240° C. The resulting film had an inherent viscosity value of 0.575 dL / g.

Example

4A film was pressed from the ground polyester of Example 1H at 240° C. The resulting film had an inherent viscosity value of 0.0.652 dL / g.

where:

A is Isophthalic Acid

B is Ethylene Glycol

C is 2,2,4,4-Tetramethyl-1,3-cyclobutanediol (approx. 50 / 50 cis / trans)

D is 2,2,4,4-Tetramethyl-1,3-cyclobutanediol (98 / 2 cis / trans)

E is 2,2,4,4-Tetramethyl-1,3-cyclobutanediol (5 / 95 cis / trans)

[0221] As shown in Table 1 and FIG. 1, 2,2,4,4-tetramethyl-1,3-cyclobutanediol is more effective than other comonomers, such ethylene glycol and isophthalic acid, at increasing the crystallization half-time, i.e., the time required for a polymer to reach half of its maximum crystallinity. By decreasing the crystallization rate of PCT (increasing the crystallization half-time), amorphous articles based on 2,2,4,4-tetramethyl-1,3-cyclobutanediol-modified PCT as described herein may be fabricated by methods known in the art. As shown in Table 1, these materials can exhibit higher glass transition temperatures...

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Abstract

Described are ophthalmic products comprising polyester compositions comprising polyesters which comprise (a) a dicarboxylicacid component having terephthalic acid residues; optionally, aromatic dicarboxylic acid residues or aliphatic dicarboxylic acid residues or ester residues thereof; 2,2,4,4-tetramethyl-1,3-cyclobutanediol residues; and 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 ophthalmic products comprising a polyester compositions made from tere...

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 EASTMAN CHEM CO
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