Patent GB-414336-A (GB)
Title: Improvements in or relating to the manufacture of substituted amides and compositions containing same
IPC: C08L27/00
Filed: 1932-10-24
Abstract: Alkylamides of organic carboxylic acids are prepared by reacting a mono- or dialkylamine with a substantially anhydrous liquid comprising an organic carboxylic acid at an elevated temperature, removing the water formed substantially as formed and recovering the acid amide.  The alkylamines used may contain one or two alkyl groups which may be the same or different and may be unsaturated, the term alkyl including any monovalent hydrocarbon radical in which no carbon atom directly attached to the amino nitrogen is a member of an aromatic nucleus.  Amines in which two of the valences of the amino nitrogen are satisfied by an organic hydrocarbon radical with the free valences each attached to the amino nitrogen atom may be used. Suitable amines are dicrotylamine, cyclohexylamine, dibutylamine, benzylamine, pyrrolidine, piperidine, cetylamine, stearylamine, methylamine, dimethylamine, methylethylamine, ethylazine, diethylamine, dipropylamine, dibutylamine, heptylamine, octylamine, decylamine, ethylcetylamine, furylamine, dilaurylamine, ethylbutylamine or in general any amine containing at least one hydrogen atom attached to the amino nitrogen atom and which can be vaporized directly or by blowing with a current of inert gas such as nitrogen, toluene, xylene or carbondioxide.  In examples (1) succinic acid is treated with dimethylamine to give tetramethylsuccinamide; (2) adipic acid with diethylamine to give tetraethyladipamide; (3) benzoylbenzoic acid with dimethylamine to give dimethylbenzoylbenzamide; (4) phthalic anhydride with dibutylamine to give tetrabutylphthalamide; (5) cotton seed oil acids with dimethylamine or dibutylamine to give the dimethylamide or dibutylamide; (7) stearic acid with diethylamine to give diethylstearamide; (8) abietic acid with dibutylamine to give dibutylabietamide; and (9) adipic acid with monoethylamine to give symmetrical dimethyladipamide.  Suitable monocarboxylic acids for conversion include the aliphatic acids from formic to stearic acids including acetic, propionic, butyric, iso-butyric, capric, caproic, caprylic, lauric, myristic, palmitic and stearic; unsaturated acids such as crotonic, acrylic, and oleic acids; hydroxy acids such as lactic, glycollic and hydroxystearic acids; keto-acids such as pyruvic and levulinic acids; aromatic acids such as benzoic, anisic, toluic, salicylic, benzoylbenzoic and naphthoic acids; and mixtures of acids such as those obtained by the hydrolysis of linseed, chinawood, castor, cottonseed or coco-nut oils.  Suitable polycarboxylic acids include adipic, pimelic, suteric, azelaic, succinic, glutaric, maleic, fumaric, sebacic, naphthalic, malonic, trimesic, trimellitic, uritic, naphthalenetetracarboxylic, tricarllylic, diphenic, quinolinic, cinchomeronic acids and substituted acids such as citric, malic, itaconic, tartaric and hydroxy phthalic acids.  The amides are soluble in alcohol, acetone, esters and aromatic hydrocarbons. The polyethyl and polymethylamides of the polycarboxylic acids and of the lower aliphatic monocarboxylic acids are soluble in water.  The alkylamides are suitable as plasticizers for cellulose derivatives such as cellulose nitrate, acetate, butyrate, acetobutyrate, ethyl cellulose, and benzylcellulose alone or in combination with natural resins such as rosin, congo, dammar; synthetic resins such as phenol - aldehyde, vinyl, urea - formaldehyde, polyhydric alcohol-polybasic acid resins; semidrying or non-drying oils such as linseed, chinawood, castor, or cottonseed oils; mineral oils; pigments such as "titanox," lithopone, iron blue, lakes, iron oxide, carbon black; solvents; plasticizers; waxes such as carnauba, candelilla, paraffin wax or beeswax; bitumens; tars; rubbers; proteins or fillers.  The compositions may be used in moulded products, in coating compositions for wood, stone, leather, paper, rubber, textiles or metal, in impregnating compositions for paper or cloth; in coated fabrics, in adhesives, in safety glass, in laminated paper or wood and in glass substitutes. Typical coating compositions comprise (10) cellulose nitrate, damar, tetrabutyladipamide, castor oil and solvent; (11) cellulose nitrate, damar, dibutylstearamide and solvent; (12) cellulose nitrate, resin, castor oil, diethylstearamide and solvent; (13) cellulose nitrate, dimethylamides of coco-nut oil acids and solvent; (14) cellulose nitrate, pigment, resin, castor oil, tetrabutylphthalamide and solvent; (15) cellulose acetate, tetraethyl adipamide and solvent; and (16) ethyl cellulose, tetramethylphthalamide and solvent. Typical plastic compositions are (17) cellulose nitrate and tetrabutyladipamide; (18) cellulose acetate and tetramethylsuccinamide; (19) cellulose nitrate, cellulose acetate and tetramethylphthalamide; (20) ethyl cellulose and tetramethyladipamide; (21) cellulose butyrate and tetramethylphthalamide; (22) cellulose propionate and tetraethyladipamide; (23) cellulose aceto-butyrate and tetraethylsuccinamide; (24) cellulose nitrate and diethylstearamide; (25) cellulose nitrate, dibutylamides of coco-nut oil acids, filler and pigment; (26) cellulose acetate, tetraethylsebacamide, filler and pigment.  The compositions may be prepared with or without the use of solvents such as alcohol with cellulose nitrate, acetone with cellulose acetate or toluol-alcohol mixtures with cellulose ethers. The alkylamide plasticizer may be replaced in part by other known plasticizers such as dibutylphthalate, triacetin, camphor, dimethylphthalate, acetanilide or triphenylphosphate.ALSO:Alkylamides of organic carboxylic acids are suitable as plasticizers for cellulose derivatives such as cellulose nitrate, acetate, butyrate, acetobutyrate, ethyl cellulose or benzyl cellulose alone or in combination with natural resins such as rosin, congo or dammar; synthetic resins such as phenol-aldehyde, vinyl, urea-aldehyde, polyhydric alcohol-polybasic acid resins; semi-drying or non-drying oils such as linseed, china-wood, castor or cotton seed oils, mineral oils; pigments such as "Titanox," lithopone, iron blue, lakes, iron oxide, carbon black; plasticizers such as dibutyl or dimethyl phthalate, triacetin, camphor, acetanilide or triphenyl phosphate; waxes such as carnauba, candelilla, paraffin or bees wax; bitumens; rubber; proteins or fillers.  The compositions may be used in moulded products, glass substitutes and adhesives.  Examples give typical compositions which may be prepared with or without the use of fillers.