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GB363690A - Manufacture of new condensation products containing sulphur

GB363690A - Manufacture of new condensation products containing sulphur - Google PatentsManufacture of new condensation products containing sulphur Info
Publication number
GB363690A
GB363690A GB18927/30A GB1892730A GB363690A GB 363690 A GB363690 A GB 363690A GB 18927/30 A GB18927/30 A GB 18927/30A GB 1892730 A GB1892730 A GB 1892730A GB 363690 A GB363690 A GB 363690A
Authority
GB
United Kingdom
Prior art keywords
mol
triazine
solution
sodium
cyanuric chloride
Prior art date
1929-06-20
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB18927/30A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Schweiz AG
Original Assignee
Gesellschaft fuer Chemische Industrie in Basel CIBA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
1929-06-20
Filing date
1930-06-20
Publication date
1931-12-14
1930-06-20 Application filed by Gesellschaft fuer Chemische Industrie in Basel CIBA filed Critical Gesellschaft fuer Chemische Industrie in Basel CIBA
1931-12-14 Publication of GB363690A publication Critical patent/GB363690A/en
Status Expired legal-status Critical Current
Links Landscapes Abstract

Mercapto derivatives of 1 : 3 : 5-triazine applicable as anti-agers and vulcanization accelerators for rubber are obtained by reaction of compounds of the type <FORM:0363690/IV/1> in which at least one x is a replaceable halogen atom, with sulphur compounds in which the sulphur is contained in a residue capable of conversion by saponification or reduction into the mercapto group, and subjecting the product to such saponification or reduction. Suitable sulphur compounds are thiosulphates, sulphocyanides, xanthates, disulphides, and polysulphides. If the product from the primary reaction still contains replaceable halogen atoms it may be caused to react prior to the saponification or reduction with compounds containing replaceable hydrogen, such as water, ammonia, aliphatic and aromatic amines, alcohols, mercaptans, phenols, and thiophenols. Alternatively mercapto-1 : 3 : 5-triazines containing as nuclear substituent an aromatic residue free from sulphonic or carboxylic groups are obtainable by reaction of monoaryl derivatives of 1 : 3 : 5-triazine containing not more than two replaceable chlorine atoms with soluble hydrosulphides. The products may be purified by separation in the form of their ammonium, alkali metal, or alkaline-earth metal salts which are sparingly soluble or capable of being salted out. The following examples are specified: (1) The condensation product from 1 mol. of cyanuric chloride and 1 mol. of aniline is warmed with a concentrated solution of sodium hydrosulphide (4 mols.); the sparingly soluble sodium salt separates on cooling, and is converted into the free dimercaptoanilino-1 : 3 : 5-triazine by means of acetic acid; mercaptoaminoanilino-1 : 3 : 5-triazine is similarly obtained from the condensation product from 1 mol. of cyanuric chloride, 1 mol. of ammonia, and 1 mol. of aniline. (2) The condensation product from 1 mol. of cyanuric chloride and 1 mol. of a -naphthylamine, is heated with a concentrated solution of sodium hydrosulphide (4 mols.) and the dimercapto-a -naphthylamino - 1 : 3 : 5-triazine is precipitated with acetic acid; mercaptoamino-a -naphthylamino-1 : 3 : 5-triazine is similarly obtainable from the condensation product from 1 mol. of cyanuric chloride, 1 mol. of ammonia, and 1 mol. of a -naphthylamine. (3) Dichloroamino-1 : 3 : 5-triazine is heated with a concentrated solution of sodium hydrosulphide; the sodium salt which separates on cooling is converted into the free dimercaptoamino-1 : 3 : 5-triazine by means of acetic acid; the mercaptodiamino-1 : 3 : 5-triazine may be obtained similarly from the chlorodiamino-1 : 3 : 5-triazine. (4) The condensation product from 1 mol. of cyanuric chloride and 2 mols. of aniline is heated with a solution of sodium disulphide (2 mols.) and further heated with addition of sodium sulphide (2 mols.); the precipitate which separates on cooling is recrystallized from hot caustic soda solution and converted into the free mercaptodianilino-1 : 3 : 5-triazine by means of acetic acid. (5) The condensation product from 1 mol. of cyanuric chloride, 1 mol. of aniline, and 1 mol. of ammonia is heated with a solution of sodium disulphide; the precipitate obtained on cooling, with addition of potassium carbonate, is suspended in caustic soda solution at 60 DEG C. and reduced by addition of zine dust; the solution is then filtered hot and the mercaptoaminoanilino-1 : 3 : 5-triazine is precipitated from the filtrate by addition of acetic acid. (6) The condensation product from 1 mol. of cyanuric chloride, 1 mol. of aniline, and 1 mol. of ammonia is introduced into an ice-cooled solution of sodium disulphide, the precipitate is filtered off and dissolved in warm water and the sodium salt salted out from the solution is decomposed with dilute acetic acid. (7) 3 Mols. of sodium thiosulphate are introduced into an ice-cooled aqueous suspension of 1 mol. of cyanuric chloride; on adding acetic acid and boiling the trimercapto-1 : 3 : 5-triazine separates. (8) 1 Mol. of sodium thiosulphate is condensed with 1 mol. of cyanuric chloride in cold aqueous solution, and 2 mols, of aniline in acetic acid solution are added while keeping the solution neutral by addition of sodium carbonate throughout the reaction; on adding acetic acid and boiling the mercaptodianilino-1 : 3 : 5-triazine separates; mercaptoaminoanilino-1 : 3 : 5-triazine is similarly obtained if 1 mol. of aniline is replaced by 1 mol. of ammonia. (9) An aqueous suspension of the condensation product from 1 mol. of cyanuric chloride, 1 mol. of aniline, and 1 mol. of ammonia is warmed with potassium xanthate, the product is boiled with caustic soda solution, and the mercaptoamino-anilino-1 : 3 : 5-triazine is precipitated from the solution obtained. (10) An aqueous solution of potassium sulphocyanide (1 mol.) is added to an ice-cooled solution of cyanuric chloride (1 mol.) in acetone and subsequently aniline (2 mols.) is added at 25-40 DEG C. and the mixture poured into water; the condensation product is filtered off and boiled with sodium sulphide or hydrosulphide to form the mercaptan. (11) A mixture of raw rubber, zinc oxide, sulphur, diphenylguanidine, purified kaolin, and the mercaptan obtained according to (4) above vulcanized in the usual manner has better ageing properties than those of a vulcanized similar mixture from which the mercaptan is omitted. Specification 318,275, [Class 2 (iii), Dyes &c.], is referred to.ALSO:Mercapto derivatives of 1 : 3 : 5-triazine applicable as anti-agers and vulcanization accelerators for rubber are obtained by reaction of compounds of the type <FORM:0363690/V/1> in which at least one #c is a replaceable halogen atom, with sulphur compounds in which the sulphur is contained in a residue capable of conversion by saponification or reduction into the mercapto group, and subjecting the product to such saponification or reduction. Suitable sulphur compounds are thiosulphates, sulphocyanides, xanthates, disulphides and polysulphides. If the product from the primary action still contains replaceable halogen atoms it may be caused to react prior to the saponification or reduction with compounds containing replaceable hydrogen, such as water, ammonia, aliphatic and aromatic amines, alcohols, mercaptans, phenols, and thiophenols. Alternatively mercapto,1 : 3 : 5-triazines containing as nuclear substituent an aromatic residue free from sulphonic or carboxylic groups are obtainable by reaction of monoaryl derivatives of 1 : 3 : 5-triazine containing not more than two replaceable chlorine atoms with soluble hydrosulphides. The products may be purified by separation in the form of their ammonium, alkali metal, or alkaline earth salts which are sparingly soluble or capable of being salted out. The products specified in the examples are the dimercaptoanilino-, mercaptoaminoanilino-, dimercapto-a -naphthylamino-, mercaptoamino-a -naphthylamino-, dimercaptoamino-, mercaptodiamino-, mercaptodianilino-, and trimercapto-1 : 3 : 5-triazines, and as an example of their use a mixture of raw rubber, zinc oxide, sulphur, diphenylguanidine, purified kaolin, and mercaptodianilino-1 : 3 : 5-triazine vulcanized in the usual manner has better ageing properties than those of a vulcanized similar mixture from which the mercaptan is omitted. Specification 318,275, [Class 70, India-rubber &c.], is referred to.

GB18927/30A 1929-06-20 1930-06-20 Manufacture of new condensation products containing sulphur Expired GB363690A (en) Applications Claiming Priority (1) Application Number Priority Date Filing Date Title CH363690X 1929-06-20 Publications (1) Publication Number Publication Date GB363690A true GB363690A (en) 1931-12-14 Family ID=4513279 Family Applications (1) Application Number Title Priority Date Filing Date GB18927/30A Expired GB363690A (en) 1929-06-20 1930-06-20 Manufacture of new condensation products containing sulphur Country Status (1) Cited By (2) * Cited by examiner, † Cited by third party Publication number Priority date Publication date Assignee Title US2505462A (en) * 1947-08-08 1950-04-25 Sterling Drug Inc Alkamine sulfides of quinoline and method of producing the same DE1191382B (en) * 1961-11-20 1965-04-22 Geigy Ag J R Process for the preparation of 2-mercapto-4,6-bis-amino-s-triazines which are preferably substituted in at least one amino group by at least one organic radical Cited By (2) * Cited by examiner, † Cited by third party Publication number Priority date Publication date Assignee Title US2505462A (en) * 1947-08-08 1950-04-25 Sterling Drug Inc Alkamine sulfides of quinoline and method of producing the same DE1191382B (en) * 1961-11-20 1965-04-22 Geigy Ag J R Process for the preparation of 2-mercapto-4,6-bis-amino-s-triazines which are preferably substituted in at least one amino group by at least one organic radical Similar Documents Publication Publication Date Title CA1191852A (en) 1985-08-13 Organic thiosulphates and thiosulphonates useful as stabilising agents for rubber vulcanisates US2321305A (en) 1943-06-08 Accelerator of vulcanization GB363690A (en) 1931-12-14 Manufacture of new condensation products containing sulphur US2464194A (en) 1949-03-08 Reduction of nitrophenols US2339002A (en) 1944-01-11 Oxidative condensation product of organic mercaptans and primary amines US2024567A (en) 1935-12-17 Preparation of organic disulphides Beech 1967 Some nucleophilic reactions of cyanuric chloride and of certain 2, 4-dichloro-1, 3, 5-triazines with compounds containing reactive hydrogen US2468952A (en) 1949-05-03 Process for the preparation of di-thiazyl disulfide Bedford et al. 1922 Reactions of Accelerators during Vulcanization. IV--Mechanism of the Action of Zinc Compounds US2340650A (en) 1944-02-01 Vulcanization of rubber US2583975A (en) 1952-01-29 Anthracene-9, 10-bis methanethiol GB413296A (en) 1934-07-10 Improvements in or relating to the manufacture of vulcanised rubber US2137820A (en) 1938-11-22 Purification of mercapto aryl thiazoles US1876929A (en) 1932-09-13 Process for producing 2-mercapto-arylene-thiazole compounds and the products GB303535A (en) 1928-12-31 New compounds and their application as vulcanisation accelerators for rubber Cambron et al. 1930 The oxidation of xanthates and some new dialkyl sulphur-and disulphur-dicarbothionates US1994641A (en) 1935-03-19 Nitrophenylthiogylcollic acids US2223042A (en) 1940-11-26 Method of making 1,1-dithio bis arylenethiazoles GB613983A (en) 1948-12-07 Manufacture of dyestuffs US1894790A (en) 1933-01-17 2,6-diamino-anthraquinone sulphides and process of preparing the same US2875242A (en) 1959-02-24 Process for the production of 1-nitronaphthalene-3, 6-and 3, 7-disulfonic acid Wight et al. 1935 74. A rearrangement of o-benzamido-sulphides US2265299A (en) 1941-12-09 Manufacture of 1, 1&#39; dithio bis aryl-thiazoles US1922923A (en) 1933-08-15 Manufacture of caoutchouc-like bodies GB853323A (en) 1960-11-02 Process for the separation of nickel from solutions containing cobalt and nickel salts

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