Polyarylate compositions and articles therefrom

• US 20060229428A1
• Filed: 04/06/2005
• Published: 10/12/2006
• Est. Priority Date: 04/06/2005
• Status: Active Grant

• Current Assignee: SHPP Global Technologies BV
• Original Assignee: General Electric Company
• Inventors: Starkey, Kyle Patrick, Kannan, Ganesh, Donovan, Michael Stephen, Shaikh, Abbas Alli Ghudubhai, Wagle, Govind Subbanna, Rajeswaran, Ramesh
• Granted Patent: US 8,497,343 B2
• Time in Patent Office: Days
• US Class Current: 528/272
• CPC Class Codes: C08G 63/547 Hydroxy compounds containing aromatic rings

Abstract

A polyarylate composition comprising: structural units derived at least one substituted or unsubstituted diacid, at least one aromatic dihydroxy compound, and an unsaturated compound. The composition possesses good optical properties, flow, stability and mechanical property. Also disclosed is a process to prepare these compositions and articles therefrom.

Claims

1. A polyarylate composition, wherein said polyarylate comprises structural units derived from

(a) a substituted or unsubstituted diacid;

(b) an aromatic dihydroxy compound of the structure (I);

wherein A¹ is independently at each occurrence a C₃-C₂₀ aromatic radical;

E is independently at each occurrence a bond, a C₁-C₂₀ aliphatic radical, a C₃-C₂₀ cycloaliphatic radical, or a C₅-C₂₀ aromatic radical, a sulfur atom, a sulfinyl group, a sulfonyl group, a selenium atom, or an oxygen atom; and

t, s and u are independently integers from 0-10 wherein at least one of t, s and u is not zero and;

(c) an unsaturated compound of structure (VIII)

R⁵—

CR⁷═

CR⁸—

R⁶ 

 

(VIII)

wherein R⁵, and R⁶ are independently at any occurrence an carboxylate, oxygen, carbonyl groups;

R⁷ and R⁸ are independently at each occurrence hydrogen, aliphatic, aromatic or cycloaliphatic groups.

2. The composition according to claim 1, wherein said dihydroxy compound is of the structure (VII)

HO—

R³—

R⁴—

R³—

OH 

 

(VII)

wherein R³ is a substituted or unsubstituted aryl group and R⁴ is selected from the group consisting of substituted or unsubstituted alkyl, substituted or unsubstituted cycloaliphatic, substituted or unsubstituted heterocyclic group, or R³ and R⁴ can be linked together to form at least five member substituted or unsubstituted ring.

3. The composition according to claim 2, wherein said at least five member ring may optionally comprise at least one heteroatom.

4. The article of claim 1, wherein said diacid is at least one selected from the group consisting of linear acids, cycloaliphatic acids, terephthalic acids, isophthalic acids, bicyclo aliphatic acids, decahydro naphthalene dicarboxylic acids, norbornene dicarboxylic acids, bicyclo octane dicarboxylic acids, 1,4-cyclohexanedicarboxylic acid, adipic acid, azelaic acid, dicarboxyl dodecanoic acid, and succinic acid, dialkyl esters, diaryl esters, anhydrides, salts, acid chlorides and acid bromides.

5. The composition of claim 1, wherein said unsaturated compound is at least one selected from the group consisting of fumaric acid, maleic acid, itaconic acid, citraconic acid, mesaconic acid, aconitic acid, traconic acid, hexenedioic acid, octenedioic acid, 5-norbornene-2,3-dicarboxylic, 4,4′

-stilbenedicarboxylic acid fumaryl chloride, 2-butene-1,4-diol, hexenediol, pentenediol, long chain unsaturated aliphatic diols and aromatic diols like stilbene-diol, and derivatives thereof.

6. The composition of claim 1, wherein said unsaturated compound is present in a range of between about 0 to about 30 percent by weight based on the total weight of said composition.

7. The composition of claim 1, wherein said unsaturated compound is present in a range of between about 5 to about 10 percent by weight based on the total weight of said composition.

8. The composition of claim 1, wherein said polyarylate may optionally comprise a stabilizing additive.

9. The composition of claim 8, wherein said stabilizing additive is selected from the group consisting of anti-oxidants, flame retardants, reinforcing materials, colorants, mold release agents, fillers, nucleating agents, UV light stabilizers, heat stabilizers, lubricants, antioxidants flame retardants, pigments or combinations thereof

10. The composition of claim 8, wherein said stabilizing additive is present at a level from about 0 to about 10 percent by weight based on the total weight of said composition.

11. The composition of claim 1, wherein said diacid is present in a range of between about 1 mole percent and about 99 mole percent.

12. The composition of claim 1, wherein said diol is present in a range of between about 99 mole percent and about 1 mole percent.

13. The composition of claim 1, wherein said polyarylate has an intrinsic viscosity of at least greater than about 0.25 dL/g.

14. The composition of claim 1, wherein said polyarylate has a glass transition temperature of between about 150°

C. and about 450°

C.

15. The composition of claim 1, wherein said polyarylate has a yellowness index of less than about 2.

16. The composition of claim 1, wherein said polyarylate composition transmits about greater than 90 percent light in the region of about 400 nm to about 800 nm.

17. An article comprising a polyarylate composition, wherein said polyarylate comprises structural units derived from

(a) a substituted or unsubstituted diacid and;

(b) an aromatic dihydroxy compound of the structure (I);

wherein A¹ is independently at each occurrence a C₃-C₂₀ aromatic radical;

E is independently at each occurrence a bond, a C₁-C₂₀ aliphatic radical, a C₃-C₂₀ cycloaliphatic radical, or a C₅-C₂₀ aromatic radical, a sulfur atom, a sulfinyl group, a sulfonyl group, a selenium atom or an oxygen atom; and

t, s and u are independently integers from 0-10 wherein at least one of t, s and u is not zero.

18. The article according to claim 17, wherein said dihydroxy compound is of the structure (VII)

HO—

R³—

R⁴—

R³—

OH 

 

(VII)

wherein R3 is a substituted or unsubstituted aryl group and R4 is selected from the group consisting of substituted or unsubstituted (secondary) alkyl, substituted or unsubstituted cycloaliphatic, substituted or unsubstituted heterocyclic group, or R3 and R4 can be linked together to form at least five member substituted or unsubstituted ring.

19. The article according to claim 18, wherein said at least five member ring may optionally comprise at least one heteroatom.

20. The article of claim 17, wherein said polyarylate may further comprise an unsaturated compound of structure (VIII)

R⁵—

CR⁷═

CR⁸—

R⁶ 

 

(VIII)

wherein R⁵ and R⁶ are independently at any occurrence a carboxylate, oxygen, carbonyl groups;

R⁷ and R⁸ are independently at each occurrence hydrogen, aliphatic, aromatic or cycloaliphatic groups.

21. The article of claim 20, wherein said unsaturated compound is at least one selected from the group consisting of fumaric acid, maleic acid, itaconic acid, citraconic acid, mesaconic acid aconitic acid, traconic acid, hexenedioic acid, octenedioic acid, 5-norbornene-2,3-dicarboxylic, 4,4′

-stilbenedicarboxylic acid fumaryl chloride, 2-butene-1,4-diol, hexenediol, pentenediol, long chain unsaturated aliphatic diols and aromatic diols like stilbene-diol, and derivatives thereof.

22. The article of claim 20, wherein said unsaturated compound is present in a range of between about 0 to about 30 percent by weight based on the total weight of said composition.

23. The article of claim 20, wherein said unsaturated compound is present in a range of between about 0 to about 10 percent by weight based on the total weight of said composition.

24. The article of claim 17, wherein said polyarylate may optionally comprise a stabilizing additive, wherein said stabilizing additive is selected from the group consisting of anti-oxidants, flame retardants, reinforcing materials, colorants, mold release agents, fillers, nucleating agents, UV light stabilizers, heat stabilizers, lubricants, antioxidants, flame retardants, pigments or combinations thereof.

25. The article of claim 17, wherein said polyarylate has an intrinsic viscosity of at least greater than about 0.25 dL/g.

26. The article of claim 17, wherein said polyarylate has a glass transition temperature of between about 150°

C. and about 450°

C.

27. The article of claim 17, wherein said polyarylate has a yellowness index of less than about 2.

28. The article of claim 17, wherein said polyarylate composition transmits about greater than 90 percent light in the region of about 400 nm to about 800 nm.

29. The article of claim 17, wherein said article is used as a substrate for optical applications.

30. A method to make an article according to claim 17, wherein said article comprises comprising a polyarylate composition, wherein said polyarylate comprises structural units derived from

(a) a substituted or unsubstituted diacid or a derivative and;

(b) an aromatic dihydroxy compound of the structure (I);

wherein A¹ is independently at each occurrence a C₃-C₂₀ aromatic radical;

E is independently at each occurrence a bond, a C₁-C₂₀ aliphatic radical, a C₃-C₂₀ cycloaliphatic radical, or a C₅-C₂₀ aromatic radical, a sulfur atom, a sulfinyl group, a sulfonyl group, a selenium atom, or an oxygen atom; and

t, s and u are independently integers from 0-10 wherein at least one of t, s and u is not zero.

31. The method of claim 31, wherein said method may optionally be carried out in presence of a solvent.