Solid presentation form of at least one phenol derivative and process for obtaining same

Patent metadata

Field	Value
Publication number	US-12145902-B2
Application number	US-201917266238-A
Country	US
Kind code	B2
Filing date	Aug 2, 2019
Priority date	Aug 9, 2018
Publication date	Nov 19, 2024
Grant date	Nov 19, 2024

Abstract

The present invention relates to a novel solid presentation form of a phenol derivative, characterized by a rounded portion and a flat portion. The compositions thus obtained have advantageous properties suitable for the storage, handling and flow of the compounds. The present invention also relates to a process for preparing these solids, and to the use thereof, in particular in the polymer and agri-food industries.

First claim

The invention claimed is:

1. A novel solid presentation form comprising at least one rounded part; a pellet; or a spherical cap; wherein the novel solid presentation form, pellet, or spherical cap comprises at least one compound of formula (I)

wherein:
n is between 0 and 5,
R 1 is selected from the group consisting of hydrogen, alkyl, and alkenyl,
R 2 is selected from the group consisting of hydroxyl, alkyl, alkenyl, alkynyl, alkoxy, formyl, and acetyl, and
the novel presentation form, the pellet, and the spherical cap each comprise at least one flat part that is a continuous surface and represents at least 5% of the total surface of each of the novel presentation form, the pellet and the spherical cap.

2. The novel presentation form, pellet, or spherical cap as claimed in claim 1 , wherein the compound of formula (I) is selected from the group consisting of hydroquinone, catechol, resorcinol, pyrogallol, 4-tert-butylcatechol, tert-butylhydroquinone, para-methoxyphenol, butylhydroxyanisole, vanillin, ethylvanillin and a compound of vanillin and ethylvanillin in a molar ratio of 2.

3. A process for preparing a novel solid presentation form, a pellet or a spherical cap comprising at least one compound of formula (I) as defined in claim 1 , the process comprising at least the following consecutive steps:
(a) arranging liquid droplets comprising at least one compound of formula (I) on a flat surface,
(b) a step of solidifying said droplets on said surface.

4. The process as claimed in claim 3 , wherein the flat surface is a band, a plate, or a disk.

5. The process as claimed in claim 3 , further comprising step (a1) heating the at least one compound of formula (I) to a temperature between 1° C. and 50° C. above its melting point before step (a).

6. The process as claimed in claim 3 , further comprising a step (a2) forming droplets before step (a).

7. The process as claimed in claim 3 , wherein the flat surface is cooled to a temperature strictly below the melting point of the compound of formula (I) to allow the solidification of said droplets.

8. The process as claimed in claim 3 , wherein the process is carried out in air, under oxygen, oxygen-depleted air, controlled atmosphere, or inert atmosphere.

9. A novel solid presentation form comprising at least one rounded part and one flat part, pellet, or spherical cap comprising at least one compound of formula (I)

in which:
n is between 0 and 5,
R 1 is selected from the group consisting of hydrogen, alkyl, and alkenyl,
R 2 is selected from the group consisting of hydroxyl, alkyl, alkenyl, alkynyl, alkoxy, formyl, and acetyl,

which can be obtained according to the process defined in claim 3 .

10. The novel solid presentation form comprising at least one rounded part and one flat part; the pellet; or the spherical cap of claim 1 , wherein n is between 0 and 4.

11. The novel solid presentation form comprising at least one rounded part and one flat part; the pellet; or the spherical cap of claim 10 , wherein n is equal to 0, 1 or 2.

12. The novel solid presentation form comprising at least one rounded part and one flat part; the pellet; or the spherical cap of claim 1 , wherein R 1 is selected from hydrogen, methyl and ethyl.

13. The novel solid presentation form comprising at least one rounded part and one flat part; the pellet; or the spherical cap of claim 1 , wherein R 2 is selected from hydroxyl, methyl, ethyl, propyl, methoxy, ethoxy and formyl.

14. The process as claimed in claim 5 , wherein the at least one compound of formula (I) is heated to a temperature between 1° C. and 20° C. above its melting point.

15. The process as claimed in claim 14 , wherein the at least one compound of formula (I) is heated to a temperature between 1° C. and 10° C. above its melting point.

16. The process as claimed in claim 8 , wherein the inert atmosphere Is under nitrogen.

17. A composition comprising the novel solid presentation form, pellet, or spherical cap as defined in claim 1 .

18. The composition of claim 17 , wherein the composition is a polymer, agri food, perfume, or pharmaceutical composition.

19. The novel solid presentation form comprising at least one rounded part; a pellet; or a spherical cap of claim 1 , wherein the novel solid presentation form, pellet, or spherical cap comprises:
between 50% and 100% by weight of at least one compound of formula (I); and
between 0% and 50% by weight of at least one compound selected from the group consisting of tocopherol derivatives.

20. The novel solid presentation form comprising at least one rounded part; a pellet; or a spherical cap of claim 19 , wherein the tocopherol derivatives comprise one or more selected from α-tocopherol, β-tocopherol, γ-tocopherol, δ-tocopherol, copper complexes having an oxidation state of 2, preferably copper acetate (Cu(OAc) 2 ) or copper dibutyldithiocarbamate (CB), 2-sec-butyl-4,6-dinitrophenol, phenylenediamine, TEMPO, TEMPO-OH, 2,4-dimethyl-6-tertbutylphenol (Topanol A), phenothiazine, butylhydroxyanisole (BHA) and 2,6-di-tert-butyl-4-methoxyphenol (DTBHA).

Assignees

• Specialty Operations France

Inventors

• Sapey-Triomphe Rodolphe
• Humblot Cédric

Classifications

• C07C41/40

  by change of physical state, e.g. by crystallisation · CPC title

• A61K9/2072

  characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms (A61K9/0004, A61K9/0056, A61K9/0065 take precedence) · CPC title

• A61K8/0216

  Solid or semisolid forms · CPC title

• A23V2002/00

  Food compositions, function of food ingredients or processes for food or foodstuffs · CPC title

• C07C2601/16

  the ring being unsaturated · CPC title