Patent GB-531316-A (GB)
Title: Improvements in cellulose derivate compositions, films, yarns, or the like containing organic ester amides
IPC: C09K23/00
Filed: 1939-04-26
Abstract: 531,316. Cellulose derivative compositions; treating textiles with liquids ; acidyl amino compounds. KODAK, Ltd. April 26, 1939, No. 12482. Convention date, April 26, 1938. [Classes 2 (ii), 2 (iii) and 15 (ii)] Cellulose derivative compositions, or compositions for conditioining cellulose derivative yarns, comprise an organic ester amide of the general formula R<SP>1</SP>CO NR<SP>4</SP> D<SP>1</SP> OCOR<SP>2</SP> or R<SP>1</SP>CON(D<SP>1</SP>OCOR<SP>2</SP>)(D<SP>2</SP>OCOR<SP>3</SP>) where R<SP>1</SP> R<SP>4</SP> are hydrogen, alkyl or cycloalkyl groups containing not more than 6 carbon atoms, R<SP>2</SP> R<SP>3</SP> are alkyl or cycloalkyl groups, and D<SP>1</SP> D<SP>2</SP> are divalent groups comprising alkylene or substituted alkylene groups or the groups -R<SP>5</SP>-N (COR)-D- where D is an alkylene group. R is an alkyl group and R<SP>5</SP> is a substituted alkyl group. The compositions may contain volatile solvents, plasticizers, e.g., triphenyl phosphate, or butyl phthalate, and they may contain oils. The cellulose derivative compositions may be extruded or cast to form filaments or films or they may be used in the production of lacquers. Specified ester amides are the diacetate, acetate propionate, dipropionate, acetate butyrate, propionate butyrate, dibutyrate, butyrate caproate, and dimethoxy acetate of mono-athanolamine, the triacetate, diacetate propionate, acetate dipropionate, diacetate butyrate, tripropionate, acetate dibutyrate, tributyrate, acetate propionate butyrate, acetate butyrate caproate, dibutyrate propionate, dipropionate butyrate, and tricaproate of diethanolamine. Diethanolamine diacetate propionate is obtained by mixing acetic anhyride, propionic anhydride, and ethanolamine and maintaining the temperature at 100-110 C. The mixture is refluxed for some time and then the acids are removed by fractional distillation at atmospheric pressure or under vacuum, and the product is distilled under reduced pressure. N-acetyl #-acetoxy ethylamine is obtained by adding seven equivalents of acetyl chloride to two equivalents of ethanolamine, and refluxing on a water bath to remove hydrogen chloride. Diethanolamine tricaproate is obtained by mixing diethanolamine, caproic acid, sulphuric acid and toluene, and distilling so that toluene is continuously separated from the water of reaction and returned to the still. The catalyst is neutralized and the product is recovered by distillation. Ethanolamine propionate butyrate is obtained by heating under reflux a mixture of ethanolamine, propionic anhydride and butyric anhydride, distilling off the acids formed, and then distilling the product under reduced pressure. In examples, cellulose acetate, acetate propionate, nitrate, and butyrate, and ethyl cellulose solutions are plasticized with N-ethoxy acetyl ethanolamine acetate, diacetyl butylamine, diacetyl etbanolamino diacetyl ethanolamine, #-hydroxy ethyl # or y hydroxypropyl amine dipropionate, or N-acetyl glyceryl cyclopentylamine diacetate, and the solutions are formed into films of high transparency, flexibility, and low-inflammability. Yarns of cellulose derivatives may be treated with the ester amides during or after spinning. When applied to the yarns the ester amides may be used in conjunction with mineral oils, or blown, unblown, drying, or semi-drying vegetable or animal oils. In an example, cellulose acetate yarn is conditioned and rendered seft and pliable by applying thereto a solution of N-acetyl dipropionyl diethanolamine in olive oil. Other examples describe the use of liquids consisting of or comprising ethanolamine acetate propionate, diethanolamine tripropionate, ethanolamine propionate butyrate, ethyl ethanolamine dipropionate, N-methoxyacetyl dipropanolamine dimethoxyacetate, N-cyclopentoyl diethanolamine diacetate, N-acetyl glyceryl butylamine diacetate, or N-formyl diethanolamine acetate butyrate. The treating liquid may also contain light mineral oil, blown sperm oil, blown olive oil, sperm oil, neat's foot oil, blown neat's foot oil, blown tea-seed oil, laurol, tetrahydro furfuryl glycerol acetate, glycerol acetcne, water-soluble cellulose acetate, and water. The treatment renders the yarns more suitable for knitting operations, particularly circular knitting operations. The conditioning liquids may also contain dyestuffs.