AMORPHOUS POLYESTERS ON THE BASIS OF BETULIN

Abstract

The present invention relates to amorphous polyesters on the basis of betulin, a method for producing them and their use.

Claims

1. An amorphous polyester prepared from a reaction product of a betulin with at least one compound selected from the group consisting of dicarboxylic acid, short-chain polyols, amine, vegetable oil and mixtures thereof, characterized in that the amorphous polyester has a glass transition temperature T.sub.g in the range of 50 C. to 80 C., as determined by means of DSC.

2. The polyester according to claim 1, characterized in that the proportion of betulin structural units in the polyester is 6 to 65 mol %.

3. The polyester according to claim 1, characterized in that the betulin is obtained from renewable raw materials.

4. (canceled)

5. The polyester according to claim 1, characterized in that the dicarboxylic acid is selected from the group consisting of aliphatic dicarboxylic acids with 4 to 24 carbon atoms, aromatic dicarboxylic acids and dimer acids.

6. The polyester according to claim 1, characterized in that the dimer acid is a dimer of a fatty acid and/or derivatives thereof of the general formula C.sub.nH.sub.2n+1COOH, where n is a whole number from 7 to 33.

7. The polyester according to claim 1, characterized in that the short-chain polyol contains 2 to 8 carbon atoms.

8. The polyester according to claim 1, characterized in that the vegetable oil is selected from the group consisting of soybean oil, linseed oil, sunflower oil, rapeseed oil, thistle oil, fish oil, castor oil, tall oil, coconut oil, palm oil, olive oil and mixtures thereof.

9. The polyester according to claim 1, characterized in that the polyester includes a proportion of renewable raw materials of 80 to 100 wt. %, in each case based on the total weight of the polyester.

10. A method for producing the polyester according to claim 1, comprising the following steps: a) providing a mixture comprising betulin and at least one compound selected from the group consisting of dicarboxylic acid, short-chain polyol, amine, vegetable oil and mixtures thereof; b) heating the mixture from step a) to a temperature of 200 to 250 C.

11. (canceled)

12. The method according to claim 10, characterized in that the betulin in the compound, which is selected from the group consisting of dicarboxylic acid, short-chain polyol, amine, vegetable oil and mixtures thereof, is soluble.

13. The method according to claim 10, characterized in that the mixture in step a) further contains a catalyst, in an amount of 0.01 to 0.05 wt. %, based on the total weight of the mixture.

14. A polymeric material prepared by addition of least one epoxide and/or isocyanate group, on terminal hydroxyl groups of the polyester according to claim 1.

15. (canceled)

16. A composition comprising the polyester according to claim 1.

17. A composition comprising the polymeric material of claim 14.

18. The composition of claim 17, which is an adhesive or a sealant.

19. The composition of claim 17, which is a deformation or extrusion aid.

Description

EXAMPLES

[0051] Generally, the polyesters according to the invention can be produced by mixing the individual components and heating the mixture to 220 C. in the nitrogen stream. Exemplary compositions are summarized in Table 1.

[0052] The samples are analyzed by means of GPC (gel permeation chromatography). The chromatography with an IR detector after calibration by means of a polystyrene standard occurred at a column oven temperature of 40 C. and a temperature in the detector of likewise 40 C. The relative and the numerical average and weight average molecular weight values can be calculated from the molecular weight distribution curve, and the polydispersity can be determined from that.

[0053] The polyesters thereby produced were measured by differential scanning calorimetry, wherein a sample was first heated to 150 C. in order to then be brought to 90 C. at a cooling rate of 10 Kelvin per minute. After 10 minutes at 90 C., the sample was brought to 150 C. at a heating rate of 10 Kelvin per minute and the DSC diagram was recorded. The glass transition temperature of the sample was determined with the aid of the DSC diagram.

TABLE-US-00001 TABLE 1 Acid OH value value Viscosity Glass in mg in mg Brookfield transition KOH/g KOH/g Mn in Example Composition at 140 C. temperature sample sample g/mol Polydispersity 1 131.6 g 4500 mPas 29 C. 4.0 56 2453 2.1 betulin (25 mol %), 25.5 g butanediol (31.6 mol %, 87.8 g sebacic acid (43.4 mol %) 2 110.68 g 30,000 mPas 19 C. 3.2 27 5326 2.3 betulin (25 mol %), 24.06 g 1,2-propanediol (31.6 mol %, 90.75 g azelaic acid (43.4 mol %) 3 110.68 g 310,000 mPas 59 C. 2.4 34 3872 2.1 betulin (25 mol %), 24.05 g 1,2-propanediol (31.6 mol %, 64.07 g adipic acid (43.4 mol %) 4 131.63 g 1550 mPas 12 C. 2.6 80 1933 2.1 betulin (25 mol %), 25.55 g butanediol (31.6 mol %, 87.8 g sebacic acid (43.4 mol %) 5 110.68 g 1500 mPas 1 C. 3.0 61 2472 2.3 betulin (25 mol %), 28.48 g butanediol (31.6 mol %, 89.65 g azelaic acid (43.4 mol %) 6 110.65 g 7500 mPas 29 C. 2.8 59 2207 2.1 betulin (25 mol %), 28.51 g butanediol (31.6 mol %, 63.44 g adipic acid (43.4 mol %) 7 110.68 g 185,000 mPas 63 C. 1.1 58 2356 2 betulin (25 mol %), 28.49 g butanediol (31.6 mol %, 51.25 g succinic acid (43.4 mol %) 8 64.78 g 160 mPas 35 C. 1.8 71 2508 2.3 betulin (30.5 mol %), 135.16 g castor oil (30.5 mol %) 22.08 g succinic acid (39 mol %) 9 110.67 g 25,100 mPas 42 C. 1.3 53 2552 2 betulin (25 mol%), 32.93 g 2,2-dimethyl- 1,3-propanediol (31.6 mol %), 63.42 g adipic acid (43.4 mol %) 10 103.18 g 6800 mPas 22 C. 2.0 29 2368 2.5 betulin (46.6 mol %), 4.51 g butanediol (10 mol %), 125.43 g dimer acid Pripol 1013 (43.4 mol %)