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US1928652A - Process of making mixed esters of cellulose - Google Patents

Process of making mixed esters of cellulose Download PDF

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US1928652A
US1928652A US553683A US55368331A US1928652A US 1928652 A US1928652 A US 1928652A US 553683 A US553683 A US 553683A US 55368331 A US55368331 A US 55368331A US 1928652 A US1928652 A US 1928652A
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cellulose
ester
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US553683A
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Carl J Malm
Charles R Fordyce
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Eastman Kodak Co
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Eastman Kodak Co
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B3/00—Preparation of cellulose esters of organic acids
    • C08B3/16—Preparation of mixed organic cellulose esters, e.g. cellulose aceto-formate or cellulose aceto-propionate

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  • This invention relates to the, makmg ofvarious multi-acyl'ated cellulose derivatives "by introducing organic acid'radicals into higher fatty acid esters or" cellulosalboth simple'and mixed) I higher esters of cellulose are susceptible of fur- -Which havebeen partially hydrolyzed.
  • An object of our invention is to provide a process for making themixed esters of cellulose in which the proportions of acyl radicalsmay be controlled.
  • Another object of our invention uses, some of which uses are not usually considered as adapted to the employment oi esters of cellulose.
  • esters which, when partially hydrolyzed are r suitable forfurther esterification are cellulose propionate.
  • cellulosebutyrate, cellulose acetate propionate and cellulose acetate-butyrataas Well as esters containing higher acyl radicals such as cellulose laurate, cellulose stearate, cellulose 'acetate-laurate and cellulose acetate ste'arate.
  • the hydrolysis of the mixed esters of cellulose may be carried out by the inetliodof Malrn and Fletcher application, serial No. 551,546, which dis closes that the hydrolysis may be carried out in an aqueous organicaciclsolution for example, at.
  • Theesterification by means of a fattyacid anhydride may be carried out eitheir in a solvent'reaction mixture or by fibrous acylation' in a liquid such as toluene which is a non-solvent both for the hydrolyzed ester and for the final product.
  • suitable liquids such as, for example, monochloracetic acid, alkoxyacetic acid, ethylene chloride, etc. or, in some cases, the acid correspondingto the anhydride employed or even a" dverent organic acid may be used as the'solvent whenesterifying ina sol: vent reaction mixture.
  • Example I 160 lbs. of cellulose propionate which hasbeen hydrolyzed to a propionyl content of about/5%, is placed in a reaction bath containing 480 lbs. o1": stearic acid, 400 lbs. of chloracetic anhydride, 8e0'1bs. of chloracetic acid and a small amount of a catalyst, such as magnesium perchlorate.
  • a catalyst such as magnesium perchlorate.
  • the mass is heated to about C. foryabout 6 hours.
  • the ester obtained may thenbe isolated from the reaction mixturezby. precipitat j ing in methyl alcohol. 1
  • The. product formed is cellulose propionatef stearatewhich is acetone-soluble andis also soluble in hot mineraloil of medium viscosity, which solution uponv cooling forms a jell of the con- 2 si'stency of heavy grease.
  • Example II lbs. of cellulose propionate containing about 45% propionyl is placed in a'reaction bath containing 300 lbs. of glacial 'aceticacid, 250 lbs.”
  • the resulting product is cellulose-acetate-propionate which is soluble: in acetone, ethylene chloride and methyl acetate. 1
  • the temperature maybe maintained at,l866qC. in which case, the time and the amounts of acid and anhydridemay be reduced.
  • a buffer such as sodium acetate, or some other alkali metal salt may be added, if desired, to eliminate any danger of degradation.
  • Example III l00lbs. of cellulose butyrate having about 50% butyryl content is placed in a reaction mixture containing 200 lbs. of stearic anhydride, 800 lbs. of ethoxy-acetic acid and a small amount of magnesium perchlorate. about 65 C. for about 10 hours at the end of which time the resulting ester may be separated from its reaction mixture by pouring the latter with agitation into methyl alcohol.
  • the cellulose butyrate-stearate formed is: soluble in various hydrocarbons such as mineral oil, ligroin, etc.
  • Example IV 100 lbs of cellulose butyrate having about a 50% butyryl content W rich has been subjected to 100 hours hydrolysis is placed in a reaction mixture containing approximately 1500 lbs; of
  • Example VI 100 lbs.'of cellulose acetate-proprionate, having about a 30% acetyl and 12% popionyl content is placed in about 1500 lbs. of toluene.
  • the moisture present is distilled off and a mixture of about 500 lbs; of stearic anhydride, 30 lbs. of p-toluenesulfo-chloride and 1500 lbs. of ligroin (B. P. 90-120 C.) is added.
  • the mixture is refluxed for 15-30 hours, depending upon the speed of the reaction after which the cellulose ester mayj be filteredoff .and washed with hot water if desired.
  • a cellulose acetate-propionate-stearate is obtained.
  • Example VII 100 lbs. of cellulose butyrate, having about a butyryl content is placed in 300 lbs. of pyridine, and 400 lbs. of lauryl chloride in 400 lbs. oftoluene is added. The mass is heated for 3-5 hours at about 50 C. or until complete acylation occurs. The cellulose butyrate-laurate obtained is separated from the reaction mass by pouring the latter with agitation into methyl alcohol. The ester is soluble in acetone, ethyl acetate, benzene and chloroform.
  • Example VIII 100 lbs. of cellulose butyrate having about a 50% butyryl content is placed in a reaction mix-
  • Meltss is kept at ture containing about 200 lbs. of stearic anhydride, 800 lbs. of ethylene chloride and a small amount of magnesium perchlorate.
  • the mass is kept at about C. for about 10 hours at the end of which time the resulting ester may be separated from its reaction mixture by pouring the latter with agitation into methyl alcohol.
  • the cellulose butyrate-stearate formed is soluble in various hydrocarbons such as mineral oil, ligroin etc. as well as in vegetable oils such as castor oil.
  • esters of cellulose containing high radicals such as lauryl, stearyl,
  • palmityl, etc. when partially hydrolyzed, may be employed as the starting material for adding additional acyl groups according to the method disclosed by the above examples. However, it is preferred to start with the propionate or butyrate containing esters and substitute other groups therein.
  • esters having several different acyl radicals attached to the cellulose may be employed.
  • a hydrolyzed cellulose propionate may be esterified according to our process by which a butyrate group added.
  • This cellulose propionate-butyrate may then be hydrolyzed and the resulting hydrolized cellulose propionate-butyrate may then be esterified with the addition of a lauryl group.
  • a cellulose propionate-butyrate-laurate may be formed. Still further hydrolysis and esterifiedtion is, of course, possible if the addition of still further groups is desired.
  • hydrolyzed cellulose propionate may be esterified in a bath containing acetic anhydride and lauric acid or it may, for example, be esterified in a bath containing an impeller such as ethoxyacetic anhydride and a plurality of organic acids.
  • the catalysts which will promote acylation reactions are well known and need not be enumerated here. It is, of course, within the judgmentol the skilled artisan'to determine which of these acylation catalysts is most suitable for the particular esterification which he desires to carry out.
  • the employment of any of the known catalysts for acylation in our process comes within the contemplation of our invention.
  • the various solvents or non-solvents which may be employed in the esterification according to our process are also a matter of choice and the selection of a particularly well known solvent for carrying out the esterification of the hydrolyzed esters according to our process is within the scope of our invention.
  • esters which are produced by our process may be employed for many and various uses, such as the forming of sheets or films, filaments for artificial silk, lacquers, lubricants, artificial leather, materials for moulding, waterproof coating or any other capacity in which cellulose esters have previously been employed. Many of the esters made according to our process have qualities which give them exceptional adaptability in this art, for example, some of these esters give films and filaments without employing plasticizers. triphenyl or tricresyl-phosphate, may be incorporated with the esters produced by our process when forming colloidized products therefrom.
  • esters may also be mixed with other cellulose esters, such as cellulose acetate or cellulose
  • compatible plasticizers such as cellulose which comprises treating a hydrolyzed nitrate and/or with other plastic materials such as gums, resins, waxes, heavymetal soaps, etc.
  • the process of producingfa mixed ester of cellulose which comprises esterifying a hydrolyzed acyl ester of cellulose containing an aliphatic acid radicalof 3-4 carbon atoms and l-j4 hydroxyl groups to every 24 carbon atom unit of cellulose. 4.
  • the process of producing a mixed estei of cellulose which comprises treating a hydrolyzed acyl ester of cellulose containing a higheraliphatic radical and 1-4 hydroxyl groups to every 24 carbon atom unit of cellulose with an esterify-- ing bath containing an aliphatic acid anhydride. 5.
  • the process of producing a mixed-ester of cellulose which comprises treatinga' hydrolyzed acyl ester of cellulose containing a higher aliphatic radical and 1-4 hydroxylgroups to every 24 carbon atom unit of cellulose with an esterliying bath containing analiphatic acid anhy- 'drideand a catalyst.
  • the process of producing a mixed ester of cellulose which comprises treating ahydrolyzed acyl ester oicellulose selected from the group consisting of cellulose propionate, cellulose bu tyrate, cellulose acetate-propionate, and cellulose acetatebutyrate and 1-4 hydroxyl groups to every 24 carbon atom unit of cellulose with an esterifying bathcontaining an aliphatic acid anhydride.
  • ahydrolyzed acyl ester oicellulose selected from the group consisting of cellulose propionate, cellulose bu tyrate, cellulose acetate-propionate, and cellulose acetatebutyrate and 1-4 hydroxyl groups to every 24 carbon atom unit of cellulose with an esterifying bathcontaining an aliphatic acid anhydride.
  • the process of producingja mixed ester ofcellulose whichcomprises treating a hydro: lyzed acyl ester of cellulose containing a higher aliphatic radical and 1-4 hydroxyl groups to every 24 carbon atom unit of cellulose with an esterifying bath containing a fatty acidanhydride and an organioliquid which is at least a solvent for the anhydride.
  • the process of producing a mixed ester of cellulose which comprises treating a hydrolyzed acyl ester of cellulose containing a higher aliphatic radical and 1-4 hydroxyl groups to every 24 carbon atom unit of cellulose with an esterifying bath containing a fatty acid chloride and an organic liquid which is at least a solvent for the chloride.
  • Theproc ess of producing a mixed esterof cellulose which comprises treating a hydrolyzed acyl ester of cellulose containinga higher aliphatic radical and 1-4 hydroxyl groups to every 24 carbon atom unit of cellulose with an esterifying bath containing a fatty acid anhydride, a catalyst and an organic liquid which is at least a solventfor the anhydride.
  • the process of producing a mixed esterof cellulose which comprises treating a hydrolyzed acyl ester of cellulose containing a higher aliphatic acid radical and 1-4 hydroxyl groupsto every 24 carbon atom unit of cellulose-With an esterifying bath comprising a fatty acid, an imv peller forthe esterification anda catalyst. butyratecelluloseacetate-propionate and cellu- 18.
  • Theprocess of producing a mixed ester of cellulose whichcomprises treating a hydrolyzed acyl ester of cellulose containing a higher fatty acid radical and 1-4 hydroxyl groups to every 24 carbon atom unit of cellulose with an esterifying bath comprising a fatty acid and an im-

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  • Materials Engineering (AREA)
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Description

atente' Get. 3:, 133 v Ne. Drawing. Applicants. .nuy" as, 1931 a .Serial n 553,683
18 meal. "(or sea-1th This invention relates to the, makmg ofvarious multi-acyl'ated cellulose derivatives "by introducing organic acid'radicals into higher fatty acid esters or" cellulosalboth simple'and mixed) I higher esters of cellulose are susceptible of fur- -Which havebeen partially hydrolyzed.
An object of our invention is to provide a process for making themixed esters of cellulose in which the proportions of acyl radicalsmay be controlled. 1
Another object of our invention uses, some of which uses are not usually considered as adapted to the employment oi esters of cellulose.
Hitherto the production of the mixedesters or cellulose has been either byesteriiying cellulose with an acylati'ng mixture which contributes a plurality of 'organic acid--radicalsto the ceilu lose or by esterifying an acetone-soluble cellua lose acetate as? disclosed, for example, in U; S. Patent No. 1,698,043 to Clarke and Malm. The former method does-not admit of asaccurate and precise control as may sometimes be desirable in commercial manufacture. The latterprocessis not 'as Well suited as the herein described process for the production of certain mixed esters of cellulose which do not contain the acetyl group cation to form multi-acylated estersot cellulose.
We have found that by reason'o'i the control of the content of acyl groupspossible in the hydrolysis of the higher esters of celluloseg precise regulation of the type of mixed-esters of cellulose resulting from our process is facilitated. Some of the esters which, when partially hydrolyzed are r suitable forfurther esterification are cellulose propionate. cellulosebutyrate, cellulose acetate propionate and cellulose acetate-butyrataas Well as esters containing higher acyl radicals such as cellulose laurate, cellulose stearate, cellulose 'acetate-laurate and cellulose acetate ste'arate. The hydrolysis of the mixed esters of cellulose may be carried out by the inetliodof Malrn and Fletcher application, serial No. 551,546, which dis closes that the hydrolysis may be carried out in an aqueous organicaciclsolution for example, at.
V to providea' process of making cellulose esters having dis'tinc tive properties which adapt them for particular We have found that the partiallyhydro about 100 F. The simple esters may be hydro lyzed by a like method or by any method.dis-' closed in-the prior art. 1 1
-We have'found; that the partially hydrolyzed ther esterification by (-1 fattyacid anhydrides, (2) fatty acids together with an impeller or (3) fatty acid chlorides. Theesterification by means of a fattyacid anhydride may be carried out eitheir in a solvent'reaction mixture or by fibrous acylation' in a liquid such as toluene which is a non-solvent both for the hydrolyzed ester and for the final product. Various suitable liquids suchas, for example, monochloracetic acid, alkoxyacetic acid, ethylene chloride, etc. or, in some cases, the acid correspondingto the anhydride employed or even a" diilerent organic acid may be used as the'solvent whenesterifying ina sol: vent reaction mixture.
v The following examples areillustrative ofthe application of our invention to the production, or mixed esters of cellulose; i Y
Example I 160 lbs. of cellulose propionate which hasbeen hydrolyzed to a propionyl content of about/5%, is placed in a reaction bath containing 480 lbs. o1": stearic acid, 400 lbs. of chloracetic anhydride, 8e0'1bs. of chloracetic acid and a small amount of a catalyst, such as magnesium perchlorate.
The mass is heated to about C. foryabout 6 hours. The ester obtained may thenbe isolated from the reaction mixturezby. precipitat j ing in methyl alcohol. 1 Y The. product formed is cellulose propionatef stearatewhich is acetone-soluble andis also soluble in hot mineraloil of medium viscosity, which solution uponv cooling forms a jell of the con- 2 si'stency of heavy grease. W
Example II lbs. of cellulose propionate containing about 45% propionyl is placed in a'reaction bath containing 300 lbs. of glacial 'aceticacid, 250 lbs."
of acetic anhydride and aismall amountof "sulfuric acid. Themass is maintained at about 32 C. for several hours. lhe resultingester may; then be precipitated in dilute acetic acid accordingto the methoddisclosed in Malm application No. 553.6%7. Y
The resulting product is cellulose-acetate-propionate which is soluble: in acetone, ethylene chloride and methyl acetate. 1
Ii desired, the temperature maybe maintained at,l866qC. in which case, the time and the amounts of acid and anhydridemay be reduced. In such case, a buffer such as sodium acetate, or some other alkali metal salt may be added, if desired, to eliminate any danger of degradation.
Example III l00lbs. of cellulose butyrate having about 50% butyryl content is placed in a reaction mixture containing 200 lbs. of stearic anhydride, 800 lbs. of ethoxy-acetic acid and a small amount of magnesium perchlorate. about 65 C. for about 10 hours at the end of which time the resulting ester may be separated from its reaction mixture by pouring the latter with agitation into methyl alcohol. The cellulose butyrate-stearate formed is: soluble in various hydrocarbons such as mineral oil, ligroin, etc.
as well as in vegetable oils such as castor oil.
Example IV Example V 100 lbs of cellulose butyrate having about a 50% butyryl content W rich has been subjected to 100 hours hydrolysis is placed in a reaction mixture containing approximately 1500 lbs; of
toluene, 150 lbs. of propionic anhydride and 40 lbs. of pyridine. The mixture is refluxed for 15-30 hours. The cellulose ester obtained is filtered off and washed. A cellulose propionatebutyrate is obtained.
7 Example VI 100 lbs.'of cellulose acetate-proprionate, having about a 30% acetyl and 12% popionyl content is placed in about 1500 lbs. of toluene.
The moisture present is distilled off and a mixture of about 500 lbs; of stearic anhydride, 30 lbs. of p-toluenesulfo-chloride and 1500 lbs. of ligroin (B. P. 90-120 C.) is added. The mixture is refluxed for 15-30 hours, depending upon the speed of the reaction after which the cellulose ester mayj be filteredoff .and washed with hot water if desired. A cellulose acetate-propionate-stearate is obtained.
Example VII 100 lbs. of cellulose butyrate, having about a butyryl content is placed in 300 lbs. of pyridine, and 400 lbs. of lauryl chloride in 400 lbs. oftoluene is added. The mass is heated for 3-5 hours at about 50 C. or until complete acylation occurs. The cellulose butyrate-laurate obtained is separated from the reaction mass by pouring the latter with agitation into methyl alcohol. The ester is soluble in acetone, ethyl acetate, benzene and chloroform.
Example VIII 100 lbs. of cellulose butyrate having about a 50% butyryl content is placed in a reaction mix- Themass is kept at ture containing about 200 lbs. of stearic anhydride, 800 lbs. of ethylene chloride and a small amount of magnesium perchlorate. The mass is kept at about C. for about 10 hours at the end of which time the resulting ester may be separated from its reaction mixture by pouring the latter with agitation into methyl alcohol. The cellulose butyrate-stearate formed is soluble in various hydrocarbons such as mineral oil, ligroin etc. as well as in vegetable oils such as castor oil.
As pointed out before, the esters of cellulose containing high radicals, such as lauryl, stearyl,
palmityl, etc., when partially hydrolyzed, may be employed as the starting material for adding additional acyl groups according to the method disclosed by the above examples. However, it is preferred to start with the propionate or butyrate containing esters and substitute other groups therein.
If desired, a'series of acylations, according to our process, may be employed to prepare esters having several different acyl radicals attached to the cellulose. For example, a hydrolyzed cellulose propionate may be esterified according to our process by which a butyrate group added. This cellulose propionate-butyrate may then be hydrolyzed and the resulting hydrolized cellulose propionate-butyrate may then be esterified with the addition of a lauryl group. Thus, a cellulose propionate-butyrate-laurate may be formed. Still further hydrolysis and esterifiedtion is, of course, possible if the addition of still further groups is desired.
If desired, more than one group may be added to the hydrolyzed ester upon esterification. For example, hydrolyzed cellulose propionate may be esterified in a bath containing acetic anhydride and lauric acid or it may, for example, be esterified in a bath containing an impeller such as ethoxyacetic anhydride and a plurality of organic acids.
The catalysts which will promote acylation reactions are well known and need not be enumerated here. It is, of course, within the judgmentol the skilled artisan'to determine which of these acylation catalysts is most suitable for the particular esterification which he desires to carry out. The employment of any of the known catalysts for acylation in our process comes within the contemplation of our invention. The various solvents or non-solvents which may be employed in the esterification according to our process are also a matter of choice and the selection of a particularly well known solvent for carrying out the esterification of the hydrolyzed esters according to our process is within the scope of our invention.
The esters which are produced by our process may be employed for many and various uses, such as the forming of sheets or films, filaments for artificial silk, lacquers, lubricants, artificial leather, materials for moulding, waterproof coating or any other capacity in which cellulose esters have previously been employed. Many of the esters made according to our process have qualities which give them exceptional adaptability in this art, for example, some of these esters give films and filaments without employing plasticizers. triphenyl or tricresyl-phosphate, may be incorporated with the esters produced by our process when forming colloidized products therefrom.
Our esters may also be mixed with other cellulose esters, such as cellulose acetate or cellulose However, compatible plasticizers such as cellulose which comprises treating a hydrolyzed nitrate and/or with other plastic materials such as gums, resins, waxes, heavymetal soaps, etc.
7 lulose with an esterifying bath containing They may also be employed for laminating or reinforcing glass, cellulose derivatives or other they are in sheet'or materials, especially when layer form. I
Other modifications of our process and other uses forthe esters so produced which will occur to those skilled in the art also come within the contemplation of our invention.
' It is to be understood that the term higher organic is employed herein to designate either radicals above acetyl in the number of carbon atoms or esters which contain such radicals.
What we claim as our invention is:
1. The process of producing a mixed ester of cellulose which comprises esteriiying a partially hydrolyzed acyl ester of cellulose containing a higher aliphatic acid radical and 1-4 hydroxyl groups-to every 24 carbonatom unit of cellulose.
2. The process of producing a mixedester of cellulose which comprises esterifying a hydrolyzed acyl ester of cellulose containing the radic-al of a fatty acid higher than acetic and l-4 hydroxyl groups to every 24 carbon atom unit or cellulose.
3. The process of producingfa mixed ester of cellulose which comprises esterifying a hydrolyzed acyl ester of cellulose containing an aliphatic acid radicalof 3-4 carbon atoms and l-j4 hydroxyl groups to every 24 carbon atom unit of cellulose. 4. The process of producing a mixed estei of cellulose which comprises treating a hydrolyzed acyl ester of cellulose containing a higheraliphatic radical and 1-4 hydroxyl groups to every 24 carbon atom unit of cellulose with an esterify-- ing bath containing an aliphatic acid anhydride. 5. The process of producing a mixed-ester of cellulose which comprises treatinga' hydrolyzed acyl ester of cellulose containing a higher aliphatic radical and 1-4 hydroxylgroups to every 24 carbon atom unit of cellulose with an esterliying bath containing analiphatic acid anhy- 'drideand a catalyst. I
6. The process of producing a mixed ester of cellulose which comprises treating a. hydrolyzed acyl ester of cellulose containing an aliphatic acid radical of 3-4 carbon atoms and 1-4 'hydroxyl groups to every 24 carbon atom unit of cellulose with an esterifying bath containing an aliphatic acid anhydride. Y
7. The process of producing a mixed ester of cellulose which comprises treating a hydrolyzed V acyl ester of cellulose containing an aliphatic acid radical of 3-4 carbon atoms and 1-4 hydroxyl groups to every 24 carbon atom unit of celan aliphatic acid anhydride and a catalyst. v
8. The process of producing a mixed .ester of cellulose which comprises esterfying a hydrolyzed acyl ester of cellulose selected from the group consisting of'cellulose propionate, cellulose losceacetatebutyrate and 1-4 hydroxyl groups to every 24 oarbon atom unit of cellulose.
9. The process of producing a mixed ester of cellulose which comprises treating ahydrolyzed acyl ester oicellulose selected from the group consisting of cellulose propionate, cellulose bu tyrate, cellulose acetate-propionate, and cellulose acetatebutyrate and 1-4 hydroxyl groups to every 24 carbon atom unit of cellulose with an esterifying bathcontaining an aliphatic acid anhydride.
10. The process of producing a mixed ester of acyl ester of cellulose containing a higher aliphatic radical and l-4 hydroxyl groups to every 24 carbon atom unit of cellulose with a bath containing an .esterifying agentselected from the group consisting of a fatty acid anhydride, a fat-- ty acid and a fatty acid chloride. 4 I
1.1. The process of producingja mixed ester ofcellulose whichcomprises treating a hydro: lyzed acyl ester of cellulose containing a higher aliphatic radical and 1-4 hydroxyl groups to every 24 carbon atom unit of cellulose with an esterifying bath containing a fatty acidanhydride and an organioliquid which is at least a solvent for the anhydride. V
12. The process of producing a mixed ester of cellulose which comprises treating a hydrolyzed acyl ester of cellulose containingfa higher aliphatic radical and 1-4 hydroxyl groups to every 24 carbon atom unit of cellulose with an esterifying bath containing a fatty aoidand an organic liquid which is at least a solvent for the acid. 1
13. The process of producing a mixed ester of cellulose which comprises treating a hydrolyzed acyl ester of cellulose containing a higher aliphatic radical and 1-4 hydroxyl groups to every 24 carbon atom unit of cellulose with an esterifying bath containing a fatty acid chloride and an organic liquid which is at least a solvent for the chloride.
14. Theproc ess of producing a mixed esterof cellulose which comprises treating a hydrolyzed acyl ester of cellulose containinga higher aliphatic radical and 1-4 hydroxyl groups to every 24 carbon atom unit of cellulose with an esterifying bath containing a fatty acid anhydride, a catalyst and an organic liquid which is at least a solventfor the anhydride.
15. The process of producing a mixed ester of I cellulose which comprises treating a hydrolyzed acyl ester of cellulosecontaining a higher aliphatic radical and 1-4 hydroxyl groups to every.
24 carbon atom unit. of cellulose withan esterileast a solvent for the fying bath, containing a fatty acid chloride, a.
catalyst and an organic liquid which is at least a.
solvent for the chloride.
17. The process of producing a mixed esterof cellulose which comprises treating a hydrolyzed acyl ester of cellulose containing a higher aliphatic acid radical and 1-4 hydroxyl groupsto every 24 carbon atom unit of cellulose-With an esterifying bath comprising a fatty acid, an imv peller forthe esterification anda catalyst. butyratecelluloseacetate-propionate and cellu- 18. Theprocess of producing a mixed ester of cellulose Whichcomprises treating a hydrolyzed acyl ester of cellulose containing a higher fatty acid radical and 1-4 hydroxyl groups to every 24 carbon atom unit of cellulose with an esterifying bath comprising a fatty acid and an im-
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2484124A (en) * 1945-05-03 1949-10-11 Celanese Corp Mixed long chain cellulose esters
EP0920808A1 (en) * 1997-12-05 1999-06-09 Gunze Kobunshi Corporation Films for casings of smoked foods

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2484124A (en) * 1945-05-03 1949-10-11 Celanese Corp Mixed long chain cellulose esters
EP0920808A1 (en) * 1997-12-05 1999-06-09 Gunze Kobunshi Corporation Films for casings of smoked foods

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