Chirally nematic polyesters

• US 6,291,629 B1
• Filed: 08/06/1999
• Issued: 09/18/2001
• Est. Priority Date: 02/06/1997
• Status: Expired due to Fees

• Current Assignee: BASF AG (BASF SE)
• Original Assignee: BASF AG (BASF SE)
• Inventors: Gerken, Andreas, Kricheldorf, Hans R., Krawinkel, Thorsten, Schuhmacher, Peter
• Primary Examiner(s): Boykin, Terressa M.
• Application Number:
  US09/355,347
• Time in Patent Office: 774 Days
• Field of Search: 528/176
• US Class Current: 528/176
• CPC Class Codes: A61K 2800/54 Polymers characterized by specific structures/properties
• CPC Class Codes: A61K 8/0295 Liquid crystals
• CPC Class Codes: A61K 8/85 Polyesters
• CPC Class Codes: A61Q 3/02 Nail coatings
• CPC Class Codes: C08G 63/672 Dicarboxylic acids and dihydroxy compounds
• CPC Class Codes: C08G 63/676 in which at least one of the two components contains aliphatic unsaturation
• CPC Class Codes: C08G 63/6856 Dicarboxylic acids and dihydroxy compounds
• CPC Class Codes: C09B 67/0098 Organic pigments exhibiting interference colours, e.g. nacrous pigments
• CPC Class Codes: C09K 19/3809 Polyesters; Polyester derivatives, e.g. polyamides

Abstract

Liquid crystalline chiral nematic polyesters have flexible chains comprising isosorbide, isomannide and/or isoidide units. The polyesters are not crystalline and form stable Grandjean textures which can be frozen on cooling below the glass transition temperature. They can therefore be used in particular as surface-coating materials.

Claims

1. A chiral nematic polyester with flexible chains which comprise isosorbide, isomannide and/or isoidide units and, for flexibilization of the chains, contain at least one unit derived from a member selected from the group consisting of

(a) aliphatic dicarboxylic acids,

(b) aromatic dicarboxylic acids with a flexible spacer,

(c) α

,ω

-alkanediols, and

(d) condensates of a polyalkylene terephthalate or polyalkylene naphthalate with an acylated diphenol and an acylated isosorbide.

2. A chiral nematic polyester as claimed in claim 1, wherein

units (a) are represented by the formula

3. A chiral nematic polyester as claimed in claim 1, which contains as nonflexible acid component units of the formula

and as nonflexible alcohol component diol units of the formula

wherein

L is alkyl, alkoxy, halogen, COOR, OCOR, CONHR or NHCOR,

X is S, O, N, CH₂ or a single bond,

A is a single bond,

 

or

 

and

R¹ is hydrogen, halogen, alkyl or phenyl, and

R is alkyl or hydrogen.

4. A chiral nematic polyester as claimed in claim 1, which contains from 1 to 15 mol % of isosorbide, -mannide and/or -idide units.

5. A chiral nematic polyester as claimed in claim 1, which contains from 1 to 50 mol % of units of flexibilizing the polyester chain.

6. A chiral nematic polyester as claimed in claim 1, having an inherent viscosity of about 0.10 to 3 dl/g when measured at 20°

C.

7. A chiral nematic polyester as claimed in claim 1, having glass transition temperature from about 80 to 300°

C.

8. A chiral nematic polyester as claimed in claim 1, wherein (a) is adipic acid.

9. An optical component comprising a chiral nematic polyester as claimed in claim 1.

10. A surface coating material comprising a chiral nematic polyester as claimed in claim 1.

11. A coloring agent comprising a chiral nematic polyester as claimed in claim 1.

12. The coloring agent of claim 11, selected from the group consisting of coloring components of surface-coating systems and components of printing inks.

13. A cosmetic composition comprising a chiral nematic polyester as claimed in claim 1.

14. The cosmetic composition of claim 13, selected from the group consisting of nail varnishes and lipsticks.

15. A pigment comprising a chiral nematic polyester as claimed in claim 1.

16. A coating composition comprising at least one chiral nematic polyester as claimed in claim 1.

17. A coating composition comprising at least one pigment as claimed in claim 15.

18. A process for preparing chiral nematic polyesters as claimed in claim 1, which comprises reacting free diols with dicarbonyl dichlorides in an inert aromatic solvent.

19. The process of claim 18, wherein the inert aromatic solvent is 1-chloronaphthalene.

20. A process for preparing chiral nematic polyesters as claimed in claim 1, which comprises reacting silylated diols with dicarbonyl dichlorides without diluent.

21. A process for preparing chiral nematic polyesters as claimed in claim 1, which comprises reacting acetylated diols with free dicarboxylic acids.

22. A process for preparing chiral nematic polyesters as claimed in claim 1, which comprises reacting a mixture of free dicarboxylic acids and acetylated diols with a polyester.

23. The process of claim 22, wherein the polyester is polyethylene terephthalate, polybutylene terephthalate or polyethylene naphthalate.