Biosourced alkyd resin and method for manufacturing such an alkyd resin

• US 10,131,741 B2
• Filed: 08/05/2014
• Issued: 11/20/2018
• Est. Priority Date: 08/05/2013
• Status: Active Grant

• Current Assignee: A Et A Mader, Roquette Freres
• Original Assignee: A Et A Mader, Roquette Freres
• Inventors: Barquant, Cyril, Roussel, Joel, Buffe, Clothilde, Crowther-Alwyn, Laura
• Primary Examiner(s): Kosar, Andrew D
• Assistant Examiner(s): Kenyon, John S
• Application Number:
  US14/910,007
• Publication Number:
  US 20160168318A1
• Time in Patent Office: 1,568 Days
• CPC Class Codes: C08G 63/48 by unsaturated higher fatty oils or their acids; by resin acids
• CPC Class Codes: C08G 63/672 Dicarboxylic acids and dihydroxy compounds
• CPC Class Codes: C09D 167/08 Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids

Abstract

The present invention relates to an alkyd resin as well as to a method for preparing such a resin, said alkyd resin resulting from the polycondensation:

• • of at least one polyacid, preferably biosourced, or its acid anhydride preferably biosourced,
  • of at least one component based on oil, preferably biosourced, or its corresponding fatty acid, preferably biosourced,
  • of at least one polyol, preferably biosourced, having at least two hydroxyl groups, selected from polyols comprising at least one 1,4:3,6-dianhydrohexitol unit,
  • of rosin or of at least one of its derivatives,
  • wherein at least one polyacid is succinic acid, preferably biosourced, or its anhydride, preferably biosourced;
  • and wherein the percentage by dry weight of rosin or its derivatives based on the total dry weight of succinic acid and of its anhydride and of rosin or its derivatives is comprised between about 10% and about 80%.

Claims

1. An alkyd resin resulting from the polycondensation:

of at least one polyacid or acid anhydride thereof, wherein the at least one polyacid is chosen from succinic acid, adipic acid, itaconic acid, azelaic acid, sebacic acid, tartaric acid, citric acid, malic acid, or a combination thereof;

of at least one oil or corresponding fatty acid, wherein the at least one oil is chosen from soya oil, sunflower oil, flax oil, tung oil, castor oil, tall oil, or a mixture thereof;

of at least one polyol comprising at least one 1,4;

3,6-dianhydrohexitol unit; and

of a rosin or rosin derivative, wherein the rosin or rosin derivative is chosen from Portuguese gem rosin, abietic acid, or dehydroabietic acid;

wherein the at least one polyacid comprises succinic acid or succinic acid anhydride;

and wherein the percentage by dry weight of the rosin or rosin derivative based on the total dry weight of the succinic acid or succinic acid anhydride and the rosin or rosin derivative is between about 10% and about 80%.

2. The resin according to claim 1, wherein the resin comprises from 10% to 30% by weight of the at least one polyacid.

3. The resin according to claim 1, wherein the resin comprises between 10% and 50% by weight of the at least one oil or corresponding fatty acid.

4. The resin according to claim 1, wherein the resin further comprises pentaerythritol (C₅H₁₂O₄), glycerol (C₃H₈O₃), sorbitol (C₆H₁₄O₆), or erythritol (C₄H₁₀O₄).

5. The resin according to claim 1, wherein the at least one polyol comprises 1,4:

3,6-dianhydro-D-sorbitol (isosorbide), 1,4;

3,6-dianhydro-D-mannitol (isomannide), or 1,4;

3,6-dianhydro-L-iditol (isoidide).

6. The resin according to claim 5, wherein the resin comprises from 20% to 30% by weight of the at least one polyol.

7. The resin according to claim 6, wherein the resin has an acid number of less than 20 mg KOH/g.

8. The resin according to claim 1, wherein the resin has an oil length between 10% and 50% by weight.

9. The resin according to claim 1, wherein the percentage by dry weight of the rosin or rosin derivative based on the total dry weight of the at least one polyacid or acid anhydride thereof and the rosin or rosin derivative is between about 30% and about 70%.

10. The resin according to claim 1, wherein the percentage by dry weight of the rosin or rosin derivative based on the total dry weight of the at least one polyacid or acid anhydride thereof and the rosin or rosin derivative is between about 50% and about 65%.

11. The resin according to claim 2, wherein the resin comprises from 15% to 25% by weight of the at least one polyacid.

12. The resin according to claim 3, wherein the resin comprises between 25% and 35% by weight of the at least one oil or corresponding fatty acid.

13. The resin according to claim 4, wherein the resin further comprises pentaerythritol or glycerol.

14. A method for preparing an alkyd resin according to claim 1, comprising a polycondensation step of the following components:

the at least one polyacid or acid anhydride thereof;

the at least one oil or corresponding fatty acid;

the at least one polyol; and

the rosin or rosin derivative;

wherein the percentage by dry weight of the rosin or rosin derivative based on the total dry weight of succinic acid or succinic acid anhydride and the rosin or rosin derivative is between about 10% and about 80%;

wherein the polycondensation step comprises continuous dynamic mixing of the components at a temperature between 180°

C. and 280°

C., until formation of the alkyd resin.

15. The preparation method according to claim 14, wherein the polycondensation step is carried out without a catalyst for esterification.

16. The preparation method according to claim 14, wherein the temperature of a reaction medium of the components during the polycondensation step is at least 180°

C., under a flow of chemically inert gas.

17. The preparation method according to claim 14, wherein the temperature of a reaction medium of the components during the polycondensation step is maintained for at least two hours between 220°

C. and 250°

C. until an acid number of less than 20 mg KOH/g of the alkyd resin is attained.

18. A paint comprising the resin according to claim 1.

19. A composition comprising a coating selected from coatings for adhesives, paints, wood stains, primary coats or varnishes, wherein the composition comprises the resin according to claim 1.

20. The resin according to claim 1, wherein the at least one polyacid or acid anhydride thereof comprises succinic acid or succinic acid anhydride and one or more of adipic acid, adipic acid anhydride, itaconic acid, itaconic acid anhydride, azelaic acid, azelaic acid anhydride, sebacic acid, sebacic acid anhydride, tartaric acid, tartaric acid anhydride, citric acid, citric acid anhydride, malic acid, or malic acid anhydride.

21. The resin according to claim 1, wherein the at least one polyacid further comprises a dimer of a fatty acid of plant origin, a trimer of a fatty acid of plant origin, a dimer of a fatty acid of animal origin, or a trimer of a fatty acid of animal origin.

22. The resin according to claim 1, wherein the resin results from the polycondensation:

of succinic acid or succinic acid anhydride;

of soya oil or soya fatty acid;

of isosorbide; and

of Portuguese gem rosin.

23. An alkyd resin resulting from the polycondensation of:

succinic acid or succinic acid anhydride;

at least one oil or corresponding fatty acid, wherein the at least one oil comprises soya oil, sunflower oil, flax oil, tung oil, castor oil, tall oil, or a mixture thereof;

1,4;

3,6-dianhydro-D-sorbitol (isosorbide), 1,4;

3,6-dianhydro-D-mannitol (isomannide), or 1,4;

3,6-dianhydro-L-iditol (isoidide); and

Portuguese gem rosin or a rosin derivative chosen from abietic acid or dehydroabietic acid;

wherein the Portuguese gem rosin or rosin derivative comprises from about 10% to about 80% by dry weight of the total of succinic acid or succinic acid anhydride and Portuguese gem rosin or rosin derivative.