Method for producing composition containing hardly water-soluble aromatic compound

Patent metadata

Field	Value
Publication number	US-11419797-B2
Application number	US-201816958331-A
Country	US
Kind code	B2
Filing date	Dec 27, 2018
Priority date	Dec 27, 2017
Publication date	Aug 23, 2022
Grant date	Aug 23, 2022

Abstract

Methods for producing a composition containing a hardly water-soluble aromatic compound are described which involve Step (1), including Step (1-1) for preparing a material comprising: (A) a hardly water-soluble aromatic compound, (B) a polyol, and (C) an aqueous medium, where a content of the (A) hardly water-soluble aromatic compound in the material for heating is below a saturation solubility of the (A) hardly water-soluble aromatic compound in a solvent having the same composition at 25° C. The obtained solution is then heated in Step (1-2) at normal pressure at a temperature of less than 100° C., to obtain a hardly water-soluble aromatic compound solution 1. Step (2) includes adding water to the hardly water-soluble aromatic compound solution 1 such that the resulting hardly water-soluble aromatic compound solution 2 has a concentration of the (A) hardly water-soluble aromatic compound above a saturation solubility at 25° C.

First claim

The invention claimed is:

1. A method for producing a composition containing a hardly water-soluble aromatic compound, comprising:
Step (1) of obtaining a hardly water-soluble aromatic compound solution 1, Step (1) comprising Step (1-1) of preparing a material for heating comprising (A) a hardly water-soluble aromatic compound, (B) a polyol, (C) an aqueous medium and optionally (D) a surfactant, and Step (1-2) of obtaining a heated solution containing the hardly water-soluble aromatic compound by heating the material for heating without applying a pressure at a temperature of 50° C. or more and less than 100° C.; and
Step (2) of obtaining a hardly water-soluble aromatic compound solution 2 by adding water to the hardly water-soluble aromatic compound solution 1 after the material for heating is cooled to 0 to 35° C. such that the hardly water-soluble aromatic compound solution 2 has a concentration of the (A) hardly water-soluble aromatic compound above a saturation solubility at 25° C.,
wherein, in Step (1), a content of the (D) surfactant in the material for heating is 0.1 mass % or less and a content of the (A) hardly water-soluble aromatic compound in the material for heating is below a saturation solubility of the (A) hardly water-soluble aromatic compound in a solvent composed of (B) the polyol and (C) the aqueous medium, having the same composition at 25° C.,
wherein, in Step (1-1), a mass ratio of the (B) polyol to a total mass of the (B) polyol and the (C) aqueous medium, (B)/[(B)+(C)], in the material for heating is from 0.45 to 0.98, and
wherein the (A) hardly water-soluble aromatic compound is at least one of triclosan, chlorothymol, carvacrol, chlorophen, dichlorophen, hexachlorophene, chloroxylenol, chlorocresol, methyl parahydroxybenzoate (=methyl paraben), ethyl parahydroxybenzoate (=ethyl paraben), propyl parahydroxybenzoate (=propyl paraben), isopropyl parahydroxybenzoate (=isopropyl paraben), butyl parahydroxybenzoate (=butyl paraben), isobutyl parahydroxybenzoate (=isobutyl paraben), and benzyl parahydroxybenzoate (=benzyl paraben); and o-phenylphenol, and isopropyl methylphenol.

2. The method according to claim 1 , wherein, in Step (1-1), a mass ratio of the (B) polyol to the (A) hardly water-soluble aromatic compound, (B)/(A), in the material for heating is 1 or more and 80 or less.

3. The method according to claim 1 , wherein the (A) hardly water-soluble aromatic compound is an aromatic compound having solubility of 3.0 g/L or less in water at 25° C.

4. The method according to claim 1 , wherein the (A) hardly water-soluble aromatic compound is an aromatic compound having solubility of 5 g/L or more in polyol at 25° C.

5. The method according to claim 1 , wherein the (A) hardly water-soluble aromatic compound is one or more selected from the group consisting of isopropyl methylphenols and para-hydroxybenzoates.

6. The method according to claim 1 , wherein the (B) polyol is one or more selected from the group consisting of a dihydric alcohol, a trihydric alcohol, and a condensate thereof.

7. The method according to claim 1 , wherein the (C) aqueous medium is water or an aqueous solution of a monohydric alcohol.

8. The method according to claim 1 , wherein heating time in Step (1-2) is 6 minutes or more and 120 hours or less.

9. The method according to claim 1 , wherein the Component (B) is 1,3-butanediol and the Component (C) is water in Step (1-1), and the material for heating is heated in Step (1-2) under a condition that a relation between Dissolution State Index Y represented by the following (Equation 8) and heating time t satisfies the following (Equation 9):

Dissolution
⁢

⁢
Index
⁢

⁢
Y

=

C
0
2

C
s

×
E

=

C
0
2

C
s

×

[

17.4
⁢

e

0.085
⁢

C
BG

⁢

e

{

-
0.046

⁢
T

}

]

⁢

e

{

-
0.00047

⁢

TC
BG

-

0.032
⁢

C
BG

}

(

Equation
⁢

⁢
8

)

⁢

Assignees

• Kao Corp

Inventors

• Suzuki Takashi
• Abe Tetsuya
• Takahashi Rui
• Endo Koji
• Hagura Toyoki
• Iwai Hidetaka
• Horizumi Teruo
• Aosaki Taisuke
• Uda Akihiro
• Nakamichi Masato

Classifications

• A61K8/347

  Phenols · CPC title

• A61K8/345 Primary

  containing more than one hydroxy group · CPC title

• A61K8/37

  Esters of carboxylic acids · CPC title

• A61K8/86

  Polyethers · CPC title

• A61K2800/49

  Solubiliser, Solubilising system · CPC title