IP Library Granted Patent US 10,730,957
Granted Patent B2
US 10,730,957 · App. 14/420,911 · Granted Aug 4, 2020

Process of preparing an esterified cellulose ether in the presence of an alkali metal carboxylate and an aliphatic carboxylic acid

Inventors: Oliver Petermann (Hamburg, DE); Matthias Sprehe (Walsrode, DE); Warren K. Miller (Bend, OR)
Assignee: Dow Global Technologies LLC
C08B13/00C08B11/20
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Quick Facts
Patent No.
US 10,730,957
App. No.
14/420,911
Granted
Aug 4, 2020
Kind
B2
Abstract

In a process for preparing an esterified cellulose ether a cellulose ether is esterified with (i) an aliphatic monocarboxylic acid anhydride or (ii) a dicarboxylic acid anhydride or (iii) a combination of an aliphatic monocarboxylic acid anhydride and a dicarboxylic acid anhydride in the presence of an alkali metal carboxylate and an aliphatic carboxylic acid, wherein the molar ratio [alkali metal carboxylate/anhydroglucose units of cellulose ether] is not more than [1.20/1] and the molar ratio [aliphatic carboxylic acid/anhydroglucose units of cellulose ether] is from [3.55/1] to [9.0/1].

Claims (15)

1. A process for preparing an esterified cellulose ether wherein a cellulose ether is esterified with (i) succinic anhydride or phthalic anhydride or with (ii) succinic anhydride or phthalic anhydride in combination with an aliphatic monocarboxylic acid anhydride selected from the group consisting of acetic anhydride, butyric anhydride and propionic anhydride

in the presence of an alkali metal carboxylate and an aliphatic carboxylic acid, wherein the molar ratio [alkali metal carboxylate/anhydroglucose units of cellulose ether] is from [0.30/1] to [1.00/1], the molar ratio [aliphatic carboxylic acid/anhydroglucose units of cellulose ether] is from [3.55/1] to [9.0/1] and the cellulose ether is a hydroxypropyl methylcellulose having a viscosity of from 2.4 to 200 mPa·s, measured as a 2 weight-% solution in water at 20° C. according to ASTM D2363-79 (Reapproved 2006), and the prepared esterified cellulose ether has a weight average molecular weight M w of from 70,000 to 700,000 Dalton.

2. The process of claim 1 wherein the molar ratio [aliphatic carboxylic acid/anhydroglucose units of cellulose ether] is from [3.8/1] to [8.0/1].

3. The process of claim 2 wherein the molar ratio [aliphatic carboxylic acid / anhydroglucose units of cellulose ether] is from [4.5/1] to [6.0/1].

4. The process of claim 1 wherein the molar ratio [alkali metal carboxylate / anhydroglucose units of cellulose ether] is from [0.35/1] to [0.90/1].

5. The process of claim 4 wherein the molar ratio [alkali metal carboxylate / anhydroglucose units of cellulose ether] is from [0.50/1] to [0.80/1].

6. The process of claim 1 wherein the cellulose ether has a viscosity of from 2.5 to 50 mPa·s, measured as a 2 weight-% solution in water at 20° C. according to ASTM D2363-79 (Reapproved 2006).

7. The process of claim 1 wherein the cellulose ether is esterified with succinic anhydride or phthalic anhydride in combination with an aliphatic monocarboxylic acid anhydride selected from the group consisting of acetic anhydride, butyric anhydride and propionic anhydride.

8. The process of claim 7 wherein hydroxypropyl methylcellulose is esterified with succinic anhydride and acetic anhydride to produce hydroxypropyl methyl cellulose acetate succinate.

9. The process of claim 1 wherein the produced esterified cellulose ether has a weight average molecular weight M w of from 100,000 to 700,000 Dalton.

10. A process for preparing an esterified cellulose ether wherein a cellulose ether is esterified with (i) succinic anhydride or phthalic anhydride or with (ii) succinic anhydride or phthalic anhydride in combination with an aliphatic monocarboxylic acid anhydride selected from the group consisting of acetic anhydride, butyric anhydride and propionic anhydride in the presence of an alkali metal carboxylate and an aliphatic carboxylic acid, wherein the molar ratio [alkali metal carboxylate/anhydroglucose units of cellulose ether] is from [0.30/1] to [1.00/1], the molar ratio [aliphatic carboxylic acid/anhydroglucose units of cellulose ether] is from [3.55/1] to [9.0/1], the cellulose ether is a hydroxyalkyl alkylcellulose, the weight average molecular weight M w of the esterified cellulose ether is varied by varying the molar ratio [aliphatic carboxylic acid/anhydroglucose units of cellulose ether] and the prepared esterified cellulose ether has a weight average molecular weight M w of from 70,000 to 700,000 Dalton.

11. A process for preparing an esterified cellulose ether wherein a cellulose ether is esterified with (i) succinic anhydride or phthalic anhydride or with (ii) succinic anhydride or phthalic anhydride in combination with an aliphatic monocarboxylic acid anhydride selected from the group consisting of acetic anhydride, butyric anhydride and propionic anhydride in the presence of an alkali metal carboxylate and an aliphatic carboxylic acid, wherein the molar ratio [alkali metal carboxylate/anhydroglucose units of cellulose ether] is from [0.30/1] to [1.00/1], the molar ratio [aliphatic carboxylic acid/anhydroglucose units of cellulose ether] is from [3.55/1] to [9.0/1], the cellulose ether is a hydroxyalkyl alkylcellulose, the weight average molecular weight M w of the esterified cellulose ether is varied by varying the molar ratio [alkali metal carboxylate/anhydroglucose units of cellulose ether] and the prepared esterified cellulose ether has a weight average molecular weight M w of from 70,000 to 700,000 Dalton.

12. The process of claim 2 wherein the molar ratio [alkali metal carboxylate/anhydroglucose units of cellulose ether] is from [0.50/1] to [0.80/1].

13. The process of claim 12 wherein hydroxypropyl methylcellulose is esterified with succinic anhydride and acetic anhydride to produce hydroxypropyl methyl cellulose acetate succinate.

14. The process of claim 13 wherein the produced hydroxypropyl methyl cellulose acetate succinate has a weight average molecular weight M w of from 100,000 to 700,000 Dalton.

Assignments (5)
CHANGE OF LEGAL ENTITY Recorded Nov 28, 2020
From: DDP SPECIALTY ELECTRONIC MATERIALS US, INC.
To: DDP SPECIALTY ELECTRONIC MATERIALS US, LLC.
Reel/Frame 054530/0384 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 28, 2020
From: DOW GLOBAL TECHNOLOGIES LLC
To: THE DOW CHEMICAL COMPANY
Reel/Frame 054531/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 28, 2020
From: THE DOW CHEMICAL COMPANY
To: DDP SPECIALTY ELECTRONIC MATERIALS US, INC.
Reel/Frame 054533/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 28, 2020
From: DDP SPECIALTY ELECTRONIC MATERIALS US, LLC.
To: NUTRITION & BIOSCIENCES USA 1, LLC
Reel/Frame 054533/0575 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 23, 2020
From: PETERMANN, OLIVER; SPREHE, MATTHIAS; MILLER, WARREN K.
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 053008/0306 →