Esterified cellulose ethers of low acetone-insoluble content

Patent metadata

Field	Value
Publication number	US-10526421-B2
Application number	US-201515503600-A
Country	US
Kind code	B2
Filing date	Aug 18, 2015
Priority date	Aug 27, 2014
Publication date	Jan 7, 2020
Grant date	Jan 7, 2020

Abstract

Esterified cellulose ethers which have i) as ester groups aliphatic monovalent acyl groups or groups of the formula —C(O)—R—COOA or a combination of aliphatic monovalent acyl groups and groups of the formula —C(O)—R—COOA, wherein R is a divalent aliphatic or aromatic hydrocarbon group and A is hydrogen or a cation, and ii) a content of not more than 0.85 weight percent acetone-insoluble esterified cellulose ether particles, when the esterified cellulose ether is present in a mixture of 12.5 weight parts of esterified cellulose ether and 87.5 weight parts of acetone at 21° C., the weight percent acetone-insoluble esterified cellulose ether particles being based on the total weight of the esterified cellulose ether, wherein iii) not more than 14 percent of the acetone-insoluble esterified cellulose ether particles have a particle size of more than 90 micrometers.

First claim

The invention claimed is:

1. An esterified cellulose ether having
i) as ester groups aliphatic monovalent acyl groups or groups of the formula —C(O)—R—COOA or a combination of aliphatic monovalent acyl groups and groups of the formula —C(O)—R—COOA, wherein R is a divalent aliphatic or aromatic hydrocarbon group and A is hydrogen or a cation, and
ii) a content of not more than 0.85 weight percent acetone-insoluble esterified cellulose ether particles, when the esterified cellulose ether is present in a mixture of 12.5 weight parts of esterified cellulose ether and 87.5 weight parts of acetone at 21° C., the weight percent acetone-insoluble esterified cellulose ether particles being based on the total weight of the esterified cellulose ether, wherein iii) not more than 14 percent of the acetone-insoluble esterified cellulose ether particles have a particle size of more than 90 micrometers, the percentage being based on the total number of acetone-insoluble esterified cellulose ether particles.

2. The esterified cellulose ether of claim 1 having a content of not more than 0.50 weight percent acetone-insoluble esterified cellulose ether particles, based on the total weight of the esterified cellulose ether.

3. The esterified cellulose ether of claim 1 wherein not more than 10 percent of the acetone-insoluble esterified cellulose ether particles have a particle size of more than 90 micrometers, the percentage being based on the total number of acetone-insoluble esterified cellulose ether particles.

4. The esterified cellulose ether of claim 1 wherein the aliphatic monovalent acyl groups are acetyl, propionyl or butyryl groups and the groups of the formula —C(O)—R—COOA are —C(O)—CH 2 —CH 2 —COOA, —C(O)—CH═CH—COOA, or —C(O)—C 6 H 4 —COOA.

5. The esterified cellulose ether of claim 1 being hydroxypropyl methyl cellulose acetate succinate.

6. A process for producing the esterified cellulose ether of claim 1 comprising the steps of
I. esterifying a cellulose ether with an aliphatic monocarboxylic acid anhydride or a dicarboxylic acid anhydride or combination thereof in the presence of an aliphatic carboxylic acid to produce a reaction product mixture comprising an esterified cellulose ether and the aliphatic carboxylic acid,
II. optionally diluting the reaction product mixture obtained in step I,
III. filtering the optionally diluted reaction product mixture, and
IV. precipitating the esterified cellulose ether from the filtered reaction product mixture by contacting the filtered reaction product mixture with water.

7. The process of claim 6 wherein in the reaction product mixture obtained in step I or II is filtered through a screen having openings of up to 1000 micrometers.

8. The process of claim 6 wherein the reaction product mixture obtained in step I is mixed with a first amount of water without precipitating the esterified cellulose ether from the reaction product mixture or with an aliphatic carboxylic acid prior to filtration in step III.

9. The process of claim 6 wherein the esterification step I comprises the steps of
(IA) dissolving or dispersing a cellulose ether and a first amount of alkali metal carboxylate in an aliphatic carboxylic acid,
(IB) heating the obtained mixture to a temperature of 60° C. to 110° C. before, during or after adding an aliphatic monocarboxylic acid anhydride or a dicarboxylic acid anhydride or a combination thereof to the mixture obtained in step (IA), and allowing the esterification reaction to proceed, and
(IC) before the esterification reaction in step (IB) is completed, adding a second amount of alkali metal carboxylate and allowing the esterification reaction to further proceed.

10. The process of claim 9 wherein the first amount of alkali metal carboxylate added in step (IA) is 15 to 35 percent and the second amount of alkali metal carboxylate added in step (IB) is 65 to 85 percent, based on the total amount of added alkali metal carboxylate in the process.

11. A composition comprising a liquid diluent and at least one esterified cellulose ether of claim 1 .

12. A solid dispersion comprising at least one active ingredient in at least one esterified cellulose ether of claim 1 .

13. A dosage form being coated with the esterified cellulose ether of claim 1 .

14. A capsule shell comprising the esterified cellulose ether of claim 1 .

Assignees

• Dow Global Technologies Llc

Inventors

• Petermann Oliver
• Knarr Matthias
• Sprehe Matthias

Classifications

• A61K9/146

  with organic macromolecular compounds · CPC title

• C08B13/00 Primary

  Preparation of cellulose ether-esters · CPC title

• A61K9/2054

  Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose · CPC title

• A61K9/4816

  Wall or shell material · CPC title

• C08L1/32

  Cellulose ether-esters · CPC title