Dow Global Technolgoies LLC

Nutrition & Biosciences USA 4, Inc.

Other

Global Dow Technologies LLC

Ddp Specialty Electronic Materials Us, LLC

Oliver Petermann

David L Malotky

Meinolf Brackhagen

Matthias Sprehe

Matthias Knarr

Nicholas S Grasman

Robert B Appell

Roland Adden

Robert L Sammler

Steven J Guillaudeu

Robert L Schmitt

Warren Kenyon Miller

Robert Thomas Nilsson

Roland Bayer

True L Rogers

Jin Zhao

David E Wallick

David M Meunier

Yongfu Li

Neal J Fetner

René Kelling

Robert Bruce Appell

Volkhard MÜLLER

An aqueous composition which is useful for producing coatings and capsule shells comprises a) dispersed particles of an esterified cellulose ether comprising (i) groups of the formula &#x2014;C(O)&#x2014;R&#x2014;COOA or (ii) a combination of aliphatic monovalent acyl groups and groups of the formula &#x2014;C(O)&#x2014;R&#x2014;COOA, wherein R is a divalent hydrocarbon group and A is hydrogen or a cation, and the total degree of ester substitution is more than 0.70, and b) an esterified cellulose ether comprising aliphatic monovalent acyl groups and groups of the formula &#x2014;C(O)&#x2014;R&#x2014;COOH, R being a divalent hydrocarbon group, wherein I) the degree of neutralization of the groups &#x2014;C(O)&#x2014;R&#x2014;COOH is not more than 0.4, II) the total degree of ester substitution is from 0.03 to 0.70, and III) the esterified cellulose ether b) has a solubility in water of at least 2.0 weight percent at 2&#xb0; C.

Aqueous composition comprising dispersed esterified cellulose ether

An aqueous composition comprising a cellulose ether acetate being at least partially dissolved in an aqueous liquid is produced in a process, wherein an aqueous liquid is mixed with a cellulose ether acetate having a degree of substitution of acetyl groups, DSAc, of from 0.05 to 0.75 and the temperature of the mixture of the cellulose ether acetate and the aqueous liquid is set to less than 10 C to at least partially dissolve the cellulose ether acetate in the aqueous liquid.

Aqueous solution of cellulose ether acetate

An esterified cellulose ether is provided wherein the ester groups are phthalyl groups, the degree of substitution of phthalyl groups is from 0.02 to 0.18, the degree of neutralization of phthalyl groups is not more than 0.75, and the esterified cellulose ether has a solubility in water of at least 2.0 weight percent at 2&#xb0; C.

Esterified cellulose ethers comprising phthalyl groups

Esterified cellulose ethers which have i) as ester groups aliphatic monovalent acyl groups or a combination of aliphatic monovalent acyl groups and groups of the formula &#x2014;C(O)&#x2014;R&#x2014;COOA wherein R is a divalent aliphatic or aromatic hydrocarbon group and A is hydrogen or a cation, ii) a weight average molecular weight Mof from 80,000 Dalton to 220,000 Dalton, iii) a Polydispersity M/Mof from 1.3 to 4.0, and iv) an M/Mof not more than 18.5, when the weight average molecular weight M, the number average molecular weight Mn and the z-average molecular weight Mare measured by SEC-MALLS using as mobile phase a mixture produced from 40 parts by volume of acetonitrile and 60 parts by volume of aqueous buffer containing 50 mM NaH&#x2014;POand 0.1 M NaNO. are useful as enteric polymers for pharmaceutical dosage forms.

Esterified cellulose ethers of high molecular weight and homogeneity

An esterified cellulose comprising aliphatic monovalent acyl groups and groups of the formula &#x2014;C(O)&#x2014;R&#x2014;COOH, R being a divalent hydrocarbon group, has the following properties: i) the degree of neutralization of the groups &#x2014;C(O)&#x2014;R&#x2014;COOH is not more than 0.4, ii) the total degree of ester substitution is from 0.03 to 0.38, and iii) the esterified cellulose ether has a solubility in water of at least 2.0 weight percent at 20&#xb0; C.

Gelling esterified cellulose ethers

A process for producing a water-soluble cellulose derivative of a reduced content of water-insoluble particles comprises the steps of a) reacting cellulose with an alkaline material to produce alkali cellulose, b) reacting the produced alkali cellulose with one or more derivatizing agents to produce a water-soluble cellulose derivative, c) washing the produced cellulose derivative with an aqueous liquid once or several times to provide a moist cellulose derivative having a water content of 25 to 85 percent, based on the total weight of the moist cellulose derivative, d) subjecting the moist cellulose derivative to homogenization to form the moist cellulose derivative to a paste, and e) pressing the paste through a filter of a pore size of up to 200 &#x3bc;m.

Process for producing a water-soluble cellulose derivative having a reduced content of water-insoluble particles

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].

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

Esterified cellulose ethers which have i) as ester groups aliphatic monovalent acyl groups or groups of the formula &#x2014;C(O)&#x2014;R&#x2014;COOA or a combination of aliphatic monovalent acyl groups and groups of the formula &#x2014;C(O)&#x2014;R&#x2014;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&#xb0; 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.

Esterified cellulose ethers of low acetone-insoluble content

A cellulose ether acetate phthalate is provided, wherein the degree of substitution of phthalyl groups is from 0.02 to 0.25, the degree of neutralization of phthalyl groups is not more than 0.5, the degree of substitution of acetyl groups is from 0.02 to 0.40, and the total degree of substitution of phthalyl and acetyl groups is not more than 0.50. The cellulose ether acetate phthalate has a solubility in water of at least 2.0 weight percent at 2&#xb0; C.

Cellulose ether acetate phthalates

1. An esterified cellulose ether which i) comprises groups of the formula &#x2014;C(O)&#x2014;R&#x2014;COOH or a combination of aliphatic monovalent acyl groups and groups of the formula &#x2014;C(O)&#x2014;R&#x2014;COOH, wherein R is a divalent hydrocarbon group, ii) has a weight average molecular weight Mof up to 70,000 Dalton, iii) has a degree of neutralization of the groups &#x2014;C(O)&#x2014;R&#x2014;COOH of not more than 0.4, and iv) has a solubility in water of at least 2.0 weight percent at 2&#xb0; C., is useful for preparing enteric capsules.

Water-soluble esterified cellulose ethers

An esterified cellulose ether comprising aliphatic monovalent acyl groups and groups of the formula &#x2014;C(O)&#x2014;R&#x2014;COOH, R being a divalent hydrocarbon group, has the following properties: i) the degree of neutralization of the groups &#x2014;C(O)&#x2014;R&#x2014;COOH is not more than 0.4, ii) the total degree of ester substitution is from 0.10 to 0.70, and iii) the esterified cellulose ether has a solubility in water of at least 2.0 weight percent at 2 C.

Water-soluble esterified cellulose ethers having a low degree of neutralization

A process for producing an esterified cellulose ether can be efficiently be produced by reacting a moist cellulose ether having a water content of at least 10 percent, based on the weight of the moist cellulose ether, with an aliphatic monocarboxylic acid anhydride, a dicarboxylic acid anhydride or a combination thereof. Further improvements in efficiency and reduction in process steps are achieved in a process for producing an esterified cellulose ether which comprises the steps of a) reacting cellulose with an alkaline material to produce alkali cellulose, b) reacting the produced alkali cellulose with one or more etherifying agents and washing the produced cellulose ether to obtain a moist cellulose ether having a water content of at least 10 weight percent, and c) reacting the moist cellulose ether with an aliphatic monocarboxylic acid anhydride and/or a dicarboxylic acid anhydride and with a depolymerizing agent.

Efficient process for preparing an ester of a cellulose ether

Esterified cellulose ethers which comprise (i) groups of the formula &#x2014;C(O)&#x2014;R&#x2014;COOA or (ii) a combination of aliphatic monovalent acyl groups and groups of the formula &#x2014;C(O)&#x2014;R&#x2014;COOA, wherein R is a divalent aliphatic or aromatic hydrocarbon group and A is hydrogen or a cation, which have a viscosity of up 50 mPa&#xb7;s, measured as a 10 wt % solution of the esterified cellulose ether in acetone at 20&#xb0; C., and a weight average molecular weight Mof at least 220,000 Dalton, or which have a viscosity of up 100 mPa&#xb7;s, measured as a 10 wt % solution of the esterified cellulose ether in acetone at 20&#xb0; C., and a weight average molecular weight Mof at least 310,000 Dalton are useful for preparing solid dispersions comprising drugs.

Esterified cellulose ethers of very high molecular weight

A liquid composition comprises an organic diluent and at least one cellulose ether having anhydroglucose units joined by 1-4 linkages and having methyl groups, hydroxyalkyl groups, and optionally alkyl groups being different from methyl as substituents such that hydroxyl groups of anhydroglucose units are substituted with methyl groups such that s23/s26 is 0.29 or less, wherein s23 is the molar fraction of anhydroglucose units wherein only the two hydroxyl groups in the 2- and 3-positions of the anhydroglucose unit are substituted with a methyl group and wherein s26 is the molar fraction of anhydroglucose units wherein only the two hydroxyl groups in the 2- and 6-positions of the anhydroglucose unit are substituted with a methyl group. The liquid composition can be used for preparing a solid dispersion of an active ingredient in a cellulose ether.

Composition comprising an organic diluent and a cellulose ether

A partially cross-linked esterified cellulose ether having A) groups of the formula &#x2014;C(O)&#x2014;R&#x2014;COOA or a combination of aliphatic monovalent acyl groups and groups of the formula &#x2014;C(O)&#x2014;R&#x2014;COOA, wherein R is a divalent aliphatic or aromatic hydrocarbon group and A is hydrogen or a cation, and B) having a molecular weight distribution such that [Wf(&#x3e;100 k)&#x2212;Wf(&#x3e;100 k)XL]/Wf(&#x3e;100 k)XL is at least 0.20, wherein Wf(&#x3e;100 k) is the total weight fraction of the esterified cellulose ether that exceeds 100,000 g/mol, and Wf(&#x3e;100 k)XL is the weight fraction that exceeds 100,000 g/mol of the methylated esterified cellulose ether is useful as enteric polymer for pharmaceutical dosage forms.

Growing community of inventors

Hamburg, Germany

Oliver Petermann