Optical articles comprising isosorbide polyesters and method for making same

• US 6,126,992 A
• Filed: 04/23/1998
• Issued: 10/03/2000
• Est. Priority Date: 04/23/1998
• Status: Expired due to Term

• Current Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: Khanarian, Garo, Charbonneau, Larry F., Witteler, Helmut B.
• Primary Examiner(s): YOON, TAE H
• Application Number:
  US09/064,846
• Time in Patent Office: 894 Days
• Field of Search: 528/298, 528/300, 428/64.4, 428/480, 428/64.6, 427/162, 427/384
• US Class Current: 427/162
• CPC Class Codes: C08G 63/668 derived from polycarboxylic acids and polyhydroxy compounds
• CPC Class Codes: G11B 7/2535 polyesters, e.g. PET, PETG or PEN
• CPC Class Codes: G11B 7/263 Preparing and using a stamper, e.g. pressing or injection molding substrates production of optical record carriers, e.g. optical discs B29D17/005
• CPC Class Codes: Y10T 428/12694 and next to Cu- or Fe-base component
• CPC Class Codes: Y10T 428/31786 Of polyester [e.g., alkyd, etc.]

Abstract

An optical article made of a transparent polymer which includes terephthaloyl moieties, optionally, other aromatic diacid moieties; ethylene glycol moieties; isosorbide moieties; and, optionally, one or more other diol moieties, wherein the polymer has an inherent viscosity of at least about 0.35 dL/g as measured on a 1% solution (weight/volume) in o-chlorophenol at 25° C.

Claims

1. An optical article comprising a transparent polymer which comprises terephthaloyl moieties, optionally, other aromatic diacid moieties;

ethylene glycol moieties;

isosorbide moieties; and

, optionally, one or more other diol moieties, wherein said polymer has an inherent viscosity of at least about 0.35 dL/g as measured on a 1% solution (weight/volume) in o-chlorophenol at 25°

C.

2. The optical article as recited in claim 1, wherein said polymer has an inherent viscosity in the range of about 0.4 to about 0.5 dL/g.

3. The optical article as recited in claim 1, wherein said optical article is a compact disc, digital versatile disc, substrate for a compact disc or digital versatile disc, lens, instrument panel window or cover, prismatic reflector, film, sheet, or optical fiber.

4. The optical article as recited in claim 1, wherein said terephthaloyl moieties are present in an amount of from about 25 mole % to about 50 mole % of said polymer, wherein said isosorbide moieties are present in an amount from about 0.25 mole % to about 40 mole % of said polymer, wherein said ethylene glycol moieties are present in an amount up to about 49.75 mole % of said polymer wherein said polymer further optionally comprises aromatic diacid moieties other than terephthaloyl moieties in the range of 0 to about 10 mole % of said polymer, and other diol moieties in an amount up to about 15 mole % of said polymer.

5. The optical article as recited in claim 4, wherein said other aromatic diacid moieties are derived from isophthalic acid, 2,5-furandicarboxylic acid, 2,5-thiophenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, 2,7-naphthalenedicarboxylic acid, 4,4'"'"'-bibenzoic acid, or mixtures thereof.

6. The optical article as recited in claim 4, wherein said other diol moieties are derived from aliphatic alkylene glycols or branched diols having from 3-12 carbon atoms and having the empirical formula HO--C_n H_2n --OH, where n is an integer from 3-12;

cis or trans-1,4-cyclohexanedimethanol or mixtures of the cis and trans isomers;

diethylene glycol;

triethylene glycol;

2,2-bis[4-(2-hydroxyethoxy)phenyl]propane;

1,1-bis [4-(2-hydroxyethoxy)phenyl]cyclohexane;

9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene;

1,4;

3,6-dianhydromannitol;

1,4;

3,6-dianhydroiditol;

1,4-anhydroerythritol;

or mixtures thereof.

7. The optical article as recited in claim 4, wherein said terephthaloyl moieties are present in an amount from about 45 mole % to about 50 mole % of said polymer, said isosorbide moieties are present in an amount from about 0.25 mole % to about 20 mole % of said polymer, said ethylene glycol moieties are present in an amount from about 5 mole % to about 48 mole % of said polymer, said other diacid moieties are present in an amount from 0 to about 5 mole % of said polymer, and said other diol moieties are present in an amount from 0 to about 2 mole % of said polymer.

8. The optical article as recited in claim 7, wherein said optical article is a compact disc, digital versatile disc, or substrate for compact disc or digital versatile disc.

9. The optical article as recited in claim 8, wherein said polymer has an inherent viscosity in the range of about 0.4 to about 0.5 dL/g.

10. A method of making an optical article, comprising the steps of:

(a) providing a polymer which comprises terephthaloyl moieties, optionally, other aromatic diacid moieties;

ethylene glycol moieties;

isosorbide moieties; and

, optionally, one or more other diol moieties, wherein said polymer has an inherent viscosity of at least about 0.35 dL/g as measured on a 1% solution (weight/volume) in o-chlorophenol at 25°

C.; and

(b) shaping said polymer into an optical article or a substrate that is used in an optical article.

11. The method as recited in claim 10, wherein said shaping comprises injection molding, compression molding, calendering, embossing, stamping, injection/compression molding or extrusion.

12. The method as recited in claim 11, wherein said extrusion is through a die that yields fibers, films, sheets or rods.

13. The method as recited in claim 10, wherein said polymer has an inherent viscosity in the range of about 0.4 to about 0.5 dL/g.

14. The method as recited in claim 10, wherein said polymer is shaped into a compact disc, digital versatile disc, substrate for compact disc or digital versatile disc, lens, instrument panel window or cover, prismatic reflector or optical fiber.

15. The method as recited in claim 10, wherein said terephthaloyl moieties are present in an amount from about 25 mole % to about 50 mole % of said polymer, wherein said isosorbide moieties are present in an amount from about 0.25 mole % to about 40 mole % of said polymer, said other aromatic diacid moieties are present in an amount from about 0 to about 10 mole % of said polymer, ethylene glycol moieties are present in an amount up to about 49.75 mole % of said polymer, and said other diol moieties are present in an amount up to about 15 mole % of said polymer.

16. The method as recited in claim 15, wherein said other aromatic diacid moieties are derived from isophthalic acid, 2,5-furandicarboxylic acid, 2,5-thiophenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, 2,7-naphthalenedicarboxylic acid, 4,4'"'"'-bibenzoic acid, or mixtures thereof.

17. The method as recited in claim 15, wherein said other diol moieties are derived from aliphatic alkylene glycols or branched diols having from 3-12 carbon atoms and having the empirical formula HO--C_n H_2n --OH, where n is an integer from 3-12;

cis or trans-1,4-cyclohexanedimethanol or mixtures of the cis and trans isomers;

diethylene glycol;

triethylene glycol;

2,2-bis[4-(2-hydroxyethoxy)phenyl]propane;

1,1-bis[4-(2-hydroxyethoxy)phenyl]cyclohexane;

9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene;

1,4;

3,6-dianhydromannitol;

1,4;

3,6-dianhydroiditol;

1,4-anhydroerythritol;

or mixtures thereof.

18. The method as recited in claim 15, wherein said terephthaloyl moieties are present in an amount from about 45 mole % to about 50 mole % of said polymer, said isosorbide moieties are present in an amount from about 0.25 mole % to about 20 mole % of said polymer, said ethylene glycol moieties are present in an amount from about 5 mole % to about 48 mole % of said polymer, said other diacid moieties are present in an amount from 0 to about 5 mole % of said polymer, and said other diol moieties are present in an amount from 0 to about 2 mole % of said polymer.

19. The method as recited in claim 18, wherein said polymer is shaped into a compact disc, digital versatile disc, or substrate for compact disc or digital versatile disc.

20. The method as recited in claim 19, wherein said polymer has an inherent viscosity in the range of about 0.4 to about 0.5 dL/g.

21. The method as recited in claim 18, further comprising molding said polymer by injection molding, compression molding or combined injection/compression molding to yield a disc having pits in a compact disc format suitable for reading with a laser;

coating said disc with a reflective coating; and

coating said disc with a protective coating to yield a compact disc.

22. The method as recited in claim 18, comprising molding said polymer by injection molding, compression molding, or combined injection/compression molding to yield a disc having pits in a digital versatile disc format suitable for reading with a laser;

coating said disc with a reflective coating;

adding additional reflective layers, semi-reflective layers or both reflective and semi-reflective layers to yield a digital versatile disc.