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    • 2. 发明专利
    • Manufacture of substituted amides
    • GB508477A
    • 1939-06-28
    • GB3593337
    • 1937-12-28
    • ALFRED WILLIAM BALDWINHENRY ALFRED PIGGOTTFRANCIS SYDNEY STATHAMICI LTD
    • 508,477. Making emulsions ; zinc salts of organic acids. BALDWIN, A. W. B., PIGGOTT, H. A., STATHAM, F. S., and IMPERIAL CHEMICAL INDUSTRIES, Ltd. Dec. 28, 1937, No. 35933. [Classes 1 (i) and 1 (iii)] [Also in Group IV] Sulphonated derivatives of amidomethyl compounds having the formula RCONHCH2 ArOR wherein R is an aliphatic radicle having at least 8 carbon atoms, R is hydrogen or a radicle of the aliphatic, aliphatic-aromatic or aromatic series and Ar is a radicle of the benzene or naphthalene series, are prepared as follows : (1) by direct sulphonation of the parent amidomethyl compound: (2) reacting a sulphonated phenol or phenolether with formaldehyde and an amide having the formula RCONH2 or with the methylol derivative of such an amide or (3) reacting together simultaneously, a phenol or phenol ether, a sulphonating agent and a methylol compound of an amide having the formula RCONH2 or a mixture of such an amide with formaldehyde. The products may be used as emulsifying agents. In examples : (1) stearohydroxybenzylamide is sulphonated with monohydrate: (2) dihydroxybenzylstea,ramide, chlorhydroxybenzylstearamide, #- hydroxynaphthylmethylstearamide, dimethoxybenzylstearamide, phenoxybenzylstearamide, benzyloxybenzylstearamide and methoxymethylbenzylamide of coconutfatty acids are similarly sulphonated; (3) #-methoxyethoxybenxylstearamide is sulphonated: (4) the amide obtained by condensing laurohydroxymethylamide with methylphenoxyacetate is sulphonated; (5) methylamides obtained by condensing phenol with the hydroxymethylamide of coconutfatty acids and by condensing a cresol mixture with stearohydroxymethylamide are sulphonated; (6) methylamides obtained by condensing anisol with laurohydroxymethylmide and by condensing anisol with hydroxymethylamide of coconutfatty acids are sulphonated ; (7) stearohydroxymethylamide is condensed and sulphonated with anisol; (8) stearamide is reacted with anisol, paraformaldehyde and sulphuric acid ; (9) laurohydroxymethylamide is condensed with sodium 2-naphthol-3 : 6-disulphonate by means of zinc chloride in glacial acetic acid ; (10) stearohydroxymethylamide is condensed with 2-methoxynaphthalene-6-sulphonate ; (11) oleohydroxymethylamide is condensed with potassium 2-methoxynaphthalene-6-sulphonate by means of zinc chloride in glacial acetic acid ; the product is a zinc salt. Phenol ethers which may also be used are :-methylsalicylate, phenetol, diphenylether, benzylphenylether, methylphenoxyacetate, #-phenoxyethanol, #- phenoxyethylmethylether, tolylmethylether and #-toloxyethylchloride.
    • 3. 发明专利
    • Manufacture of isocyanates
    • GB485761A
    • 1938-05-24
    • GB3220436
    • 1936-11-24
    • HENRY ALFRED PIGGOTTFRANCIS SYDNEY STATHAMICI LTD
    • C07C263/10
    • Isocyanates are obtained by the action of phosgene on urethanes of the type RNHCOOR1, where R is an alkyl, aryl, aralkyl or cycloalkyl group and R1 is an alkyl group. Urethanes of the type specified may be obtained by the known process wherein an alkaline alcoholic solution of a carboxylic acid amide is treated with halogen; specified amides from which urethanes may be so prepared are those of acetic, propionic, butyric, valeric, caproic, heptoic, caprylic, nonylic, capric, undecylenic, lauric, tridecylic, myristic, pentadecylic, palmitic, margaric, stearic, nondecylic, arachidic, behenic, lignoceric, cerotic, melissic, benzoic, o- and p-toluic, o- and p-methoxybenzoic, a -naphthoic, phenylacetic, phenylpropionic, o- and p-tolylacetic, hexahydrobenzoic, cyclohexylacetic, methylcyclohexylacetic, cyclohexylpropionic, naphthenic and hydroabietic acids, and also the amides of mixed acids such as are obtainable from coconut or palm-kernel oil, carnauba or montan wax, or hydrogenated fats. Suitable unethanes may also be obtained by the interaction of a primary amine and an alkyl chloroformate. Examples are given in which, by reaction with phosgene at a raised temperature in the presence or absence of a diluent, (1) N-heptadecylcarbamic acid methyl ester yields heptadecyl isocyanate; (2) N-phenylcarbamic acid methyl ester yields phenyl isocyanate; (3) N-benzylcarbamic acid methyl ester yields benzyl isocyanate; (4) N-methylcarbamic acid ethyl ester yields methyl isocyanate; (5) a mixture of N-alkylcarbamic acid esters, obtained by the action of chlorine and sodium methoxide on the amides of coconut-oil acids, yields a mixture of the corresponding alkyl isocyanates; (6) N-o-tolylcarbamic acid ethyl ester yields o-tolyl isocyanate; (7) N-p-tolylcarbamic acid methyl ester yields p-tolyl isocyanate; (8) N-cyclohexyl carbamic acid methyl ester yields cyclohexyl isocyanate.
    • 4. 发明专利
    • Manufacture of new basic products
    • GB475095A
    • 1937-11-08
    • GB1295036
    • 1936-05-07
    • HENRY ALFRED PIGGOTTFRANCIS SYDNEY STATHAMICI LTD
    • C08G73/02
    • Basic products are made by reacting the primary amide of a carboxylic acid derived from a naturally occurring oil, fat, or wax or a mixture of such amides with three or more molecular proportions of ethylene imine at elevated temperature, if desired in presence of a catalyst. The products may combine with acids to form salts. Catalysts specified are sodium hydroxide or a surface-active substance such as silica gel or kieselguhr. Three to forty molecular proportions of ethylene imine are preferred, but larger quantities may be used. Primary amides of the following acids are specified; caproic, caprylic, capric, lauric, myristic, palmitic, stearic, hydroxystearic, oleic, linoleic, linolenic, ricinoleic, elaidic, undecylenic and erucic, and mixtures of these acids derived from natural oils such as coconut oil, palm oil, palm-kernel oil, rapeseed oil, linseed oil, cotton seed oil, the acids obtainable by fat hydrogenation processes, and the acids of waxes of vegetable, animal, or mineral origin such as beeswax, carnauba wax, montan wax. Salts of the products may be formed by treatment with aqueous acids or by dissolving in an organic solvent, such as benzene, chloroform or ethanol, and treatment with acids, e.g. by passing in gaseous hydrogen chloride. The aqueous solutions of the salts are useful in textile treatment processes. In an example, stearic acid amide is heated to 130 DEG C. for 10 hours with ethylene imine in presence of aqueous sodium hydroxide; the product is dissolved in ethanol and treated with hydrogen chloride. Samples have been furnished under Sect. 2 (5) of products prepared by (A) reacting mixed amides derived from the fatty acids of coconut oil with five molecular proportions of ethylene imine in a closed vessel for 12 hours at 130 DEG C. in presence of a little water to give a basic intermediate product, which is then treated with hydrogen chloride in ethanol and acetone; (B) reacting the intermediate product under (A) with a further five molecular proportions of ethylene imine; (C) reacting the product obtained under B with a further five molecular proportions of ethylene imine; (D) dissolving the product of (C) in acetone and treating with hydrogen chloride; (E) reacting lauric acid amide with five proportions of ethylene imine and a little water in a closed vessel at 160 DEG C. for 14 hours, and then reacting the product with a further five proportions of ethylene imine. These products are stated to be foaming agents.