Biobased alkyd resin and process for manufacturing such an alkyd resin

• US 9,321,883 B2
• Filed: 02/01/2013
• Issued: 04/26/2016
• Est. Priority Date: 02/02/2012
• Status: Active Grant

• Current Assignee: A Et A Mader, Roquette Freres
• Original Assignee: A Et A Mader, Roquette Freres
• Inventors: Buffe, Clothilde, Crowther-Alwyn, Laura, Verraes, Arnaud, Roussel, Jol
• Primary Examiner(s): Chung, Susannah
• Assistant Examiner(s): Butcher, Robert T
• Application Number:
  US14/373,904
• Publication Number:
  US 20150031828A1
• Time in Patent Office: 1,180 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: C08G 2150/00 Compositions for coatings
• 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
• CPC Class Codes: C09D 5/02 Emulsion paints including aerosols

Abstract

The object of a present invention is an alkyd resin as well as the method for preparing such a resin, said alkyd resin comprising:

• • a preferably biosourced, polyacid component or its preferably biosourced acid anhydride;
  • a first polyol component, preferably biosourced, having at least two hydroxyl groups;
  • a second biosourced polyol component having at least one 1,4:3,6-dianhydrohexitol unit; and
  • a component based on biosourced oil or its corresponding biosourced fatty acid.

Claims

1. An alkyd resin, comprising:

a polyacid component or its acid anhydride;

a first polyol component having at least two hydroxyl groups;

a second polyol component which is a biosourced polyol component having at least one 1,4;

3.6-dianhydrohexitol unit; and

a biosourced oil component or its biosourced corresponding fatty acid;

wherein the alkyd resin comprises less than 10% by mole of aromatic polyacids(s) and cycloalkyl polyacid(s) or acid anhydride(s) of said aromatic polyacid(s) and cycloalkyl polyacids(s), relative to a sum of moles of the polyacid component or its acid anhydride, the first polyol component, the second polyol component, and the biosourced oil component or its biosourced corresponding fatty acid.

2. The alkyd resin according to claim 1, wherein said at least one 1,4:

3,6-dianhydrohexitol unit is selected, alone or as a combination, from;

1,4;

3,6-dianhydro-D-sorbitol, 1,4;

3,6-dianhydro-D-mannitol, and 1,14;

3,6-dianhydro-L-iditol.

3. The alkyd resin according to claim 1, wherein the 1,4:

3,6-dianhydrohexitol units of the second polyol component account for at least 5% by mole of said alkyd resin.

4. The alkyd resin according to claim 1, wherein the polyacid component is selected, done or as a combination, from:

succinic acid;

adipic acid;

itaconic acid, azelaic acid, sebacic acid, tartaric acid, citric acid, malic acid, and the acid anhydrides and/or their mixtures;

oligomers of a fatty acid of plant origin and a dimer or trimer of a fatty acid of plant origin.

5. The alkyd resin according to claim 1, wherein the first polyol component is selected from the following polyols, alone or as a combination:

penfaerythrital;

glycerol;

sorbitol;

erythritol.

6. The alkyd resin according to claim 1, wherein the component based on biosourced oil or its biosourced corresponding fatty acid is drying and/or semi-drying plant oils or their corresponding fatty acids selected from:

soybean oils or fatty acids, sunflower oils or fatty acids, flax oils or fatty acids, tung oils or fatty acids, castor oils or fatty acids, tall oil fatty acids and/or mixtures thereof.

7. The alkyd resin according to claim 1, wherein the alkyd resin has an acid index of less than 20 mg KOH/g.

8. The alkyd resin according to claim 1, wherein the alkyd resin has an oil length that is greater than or equal to 25% and less than or equal to 75%.

9. A composition comprising an alkyd resin according to claim 1, and a reactive diluent.

10. An aqueous emulsion of an alkyd resin comprising from 25% to 60% by weight of alkyd resin according to claim 1, and at least one emulsifying agent.

11. A paint formulation comprising an alkyd resin according to claim 1.

12. A method for preparing an alkyd resin according to claim 1, the method comprising a step for polycondensation of starting components forming a reaction medium comprising at least one polyacid component or its acid anhydride, one first polyol component having at least 2 hydroxyl groups, a second polyol component comprising at least one 1,4:

3,6-dianhydrohexitol unit, a biosourced oil component or its biosourced corresponding fatty acid, said starting components being mixed at a temperature between 180°

C. and 240°

C., wherein the reaction medium comprises less than 10% by mole, based on a total number of moles of the starting components, of aromatic polyacid(s), cycloalkyl polyacid(s) or acid anhydride(s) of said polyacids.

13. The preparation method according to claim 12, wherein the temperature of the reaction medium during the polycondensation step is maintained for at least two hours between 180°

C. and 240°

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

14. A method of preparing an aqueous emulsion of the alkyd resin according to claim 1, the method comprising the following steps:

a first step during which said alkyd resin is heated to a temperature greater than or equal to 40°

C. in order to form a mixture A, with stirring;

a second step during which a stabilizing agent is mixed with water, by heating to a temperature greater than or equal to 40°

C. in order to form a mixture B;

a third step during which said mixture A is incorporated in to said mixture B, with strong stirring, necessary by means of a device including a stirring blade rotating between 5,000 revolutions/min and 8,000 revolutions/min, for at least one minute in order to obtain the emulsion of said alkyd resin.

15. The alkyd resin according to claim 1, wherein the alkyd resin has an acid index of less than 15 mg KOH/g.

16. The alkyd resin according to claim 1, wherein the alkyd resin has an oil length that is higher than or equal to 40% and lower than or equal to 65%.

17. A composition comprising an alkyd resin according to claim 1, and a reactive biosourced diluent.

18. An aqueous emulsion of an alkyd resin comprising from 25% to 60% by weight of the composition according to claim 17, and at least one emulsifying agent.

19. A paint formulation comprising an aqueous emulsion according to claim 10.