IP Library › Granted Patent US 12,441,888
Granted Patent B2
US 12,441,888 · App. 17/768,240 · Granted Oct 14, 2025

Rice bran wax oxidates with low acid value

Inventors: Philipp Kratzer (Wertingen, DE); Manuel Broehmer (Gröbenzell, DE)
Assignee: CLARIANT INTERNATIONAL LTD
C08L91/06C09D11/12C09D191/06
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Quick Facts
Patent No.
US 12,441,888
App. No.
17/768,240
Granted
Oct 14, 2025
Kind
B2
Abstract

The invention relates to rice bran wax oxidates with a low acid value, to a process for their production and to their use for agricultural or forestry purposes, as an additive in plastics processing, in care products, in printing inks and/or in paints, and to saponified rice bran wax oxidates produced by saponifying the claimed rice bran wax oxidates.

Claims (37)

1. A process for producing rice bran wax oxidates (O) having an acid number of less than 40 mg KOH/g, comprising the steps of:

i) providing a rice bran wax (R) containing less than 5% by weight, based on the total weight of the rice bran wax (R), of polyesters formed from polyhydric alcohols and aliphatic carboxylic acids having 8 to 20 carbon atoms;

ii) providing a mixture (M) of chromium trioxide and sulfuric acid;

iii) performing an oxidation of the rice bran wax (R) by reacting the rice bran wax (R) with the mixture (M) while stirring and at a temperature of 80 to 150° C., in order to obtain a rice bran wax oxidate (O) in a reaction mixture;

iv) stopping the reaction and leaving the reaction mixture obtained in step iii) to stand until an organic phase has separated from an aqueous phase;

v) separating off the organic phase;

vi) optionally removing residues containing chromium compounds from the organic phase in order to obtain the rice bran wax oxidate (O) in purified form; and

vii) optionally repeating the sequence of steps ii) to vi) using the rice bran wax oxidate (O), optionally in purified form, rather than the rice bran wax (R),

wherein the oxidation in step iii) is effected over a period of 1 to 8 hours.

2. The process according to claim 1 , wherein the weight ratio of the total amount of chromium trioxide used to rice bran wax (R) used is from 1:5 to 6:5.

3. The process according to claim 1 , wherein the removing of residues containing chromium compounds in step vi) is performed and comprises the washing of the organic phase with an aqueous solution of oxalic acid and/or sulfuric acid.

4. The process according to claim 1 , wherein the removing of residues containing chromium compounds in step vi) is performed and comprises the washing of the organic phase with water.

5. The process according to claim 1 , wherein the removing of residues containing chromium compounds in step vi) is performed and comprises centrifuging of the organic phase.

6. The process according to claim 1 , wherein the concentration of chromium trioxide in the mixture (M) is from 50 to 200 g/L.

7. The process according to claim 1 , wherein the oxidation in step iii) is performed over a period of 2 to 5 hours.

8. The process according to claim 1 , wherein the stirrer speed in step iii) is between 100 and 500 rpm.

9. The process according to claim 1 , wherein no additional oxidation promoters are added to the reaction mixture.

10. A rice bran wax oxidate (O) having an acid number of less than 40 mg H/g, prepared by the process according to claim 1 .

11. The rice bran wax oxidate (O) according to claim 10 , having a proportion of polyesters formed from polyhydric alcohols and aliphatic carboxylic acids having 22 to 36 carbon atoms of less than 5% by weight, based on the total weight of the rice bran wax oxidate (O).

12. The rice bran wax oxidate (O) according to claim 10 , comprising:

a) 3% to 25% by weight, based on the total weight of the rice bran wax oxidate (O), of free aliphatic carboxylic acids having 8 to 36 carbon atoms;

b) 0% to 10% by weight, based on the total weight of the rice bran wax oxidate (O), of free aliphatic alcohols having 24 to 36 carbon atoms;

c) 0% to 5% by weight, based on the total weight of the rice bran wax oxidate (O), of free aliphatic dicarboxylic acids having 10 to 30 carbon atoms;

d) 50% to 97% by weight, based on the total weight of the rice bran wax oxidate (O), of genuine esters having 42 to 64 carbon atoms; and

e) 0% to 15% by weight, based on the total weight of the rice bran wax oxidate (O), of further natural constituents present in the rice bran wax.

13. A rice bran wax oxidate (O) having an acid number of less than 40 mg KOH/g and a proportion of polyesters formed from polyhydric alcohols and aliphatic carboxylic acids having 22 to 36 carbon atoms of less than 5% by weight, based on the total weight of the rice bran wax oxidate (O), comprising:

a) 3% to 25% by weight, based on the total weight of the rice bran wax oxidate (O), of free aliphatic carboxylic acids having 8 to 36 carbon atoms;

b) 0% to 10% by weight, based on the total weight of the rice bran wax oxidate (O), of free aliphatic alcohols having 24 to 36 carbon atoms;

c) 0% to 5% by weight, based on the total weight of the rice bran wax oxidate (O), of free aliphatic dicarboxylic acids having 10 to 30 carbon atoms;

d) 50% to 97% by weight, based on the total weight of the rice bran wax oxidate (O), of genuine esters having 42 to 64 carbon atoms; and

e) 0% to 15% by weight, based on the total weight of the rice bran wax oxidate (O), of further natural constituents present in the rice bran wax.

14. The rice bran wax oxidate (O) according to claim 10 , containing not more than 5% by weight, based on the total weight of the rice bran wax oxidate (O), of lignoceric acid.

15. A saponified rice bran wax oxidate (V), produced by saponifying the rice bran wax oxidate (O) according to claim 10 with a basic metal salt.

16. An additive comprising the saponified rice bran wax oxidate (V) according to claim 15 .

17. An additive comprising the rice bran wax oxidate (O) according to claim 10 .

18. The rice bran wax oxidate (O) according to claim 13 , containing not more than 5% by weight, based on the total weight of the rice bran wax oxidate (O), of lignoceric acid.

19. A saponified rice bran wax oxidate (V), produced by saponifying the rice bran wax oxidate (O) according to claim 13 with a basic metal salt.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 18, 2022
From: KRATZER, PHILIPP; BROEHMER, MANUEL
To: CLARIANT INTERNATIONAL LTD
Reel/Frame 059948/0072 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 12, 2022
From: KRATZER, PHILIPP; BROEHMER, MANUEL
To: CLARIANT INTERNATIONAL LTD
Reel/Frame 060019/0849 →
Priority Claims (3)
EP 19203444 · Oct 15, 2019 · regional
EP 19203445 · Oct 15, 2019 · regional
EP 19203634 · Oct 16, 2019 · regional
Continuity (1)
Related Publication 20240117188A1 · Apr 11, 2024
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