GB929182A - Production of azoalkanes - Google Patents

Production of azoalkanes

Info

Publication number
GB929182A
GB929182A GB4350659A GB4350659A GB929182A GB 929182 A GB929182 A GB 929182A GB 4350659 A GB4350659 A GB 4350659A GB 4350659 A GB4350659 A GB 4350659A GB 929182 A GB929182 A GB 929182A
Authority
GB
United Kingdom
Prior art keywords
group
acetoxy
cor11
cycloaliphatic
acid
Prior art date
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
GB4350659A
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.)
Monsanto Chemicals Ltd
Monsanto Chemical Co
Original Assignee
Monsanto Chemicals Ltd
Monsanto Chemical Co
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.)
Filing date
Publication date
Priority claimed from CH6762758A external-priority patent/CH374700A/en
Application filed by Monsanto Chemicals Ltd, Monsanto Chemical Co filed Critical Monsanto Chemicals Ltd
Publication of GB929182A publication Critical patent/GB929182A/en
Expired legal-status Critical Current

Links

Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/008—Azides

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Polymerization catalysts comprise a ,a 1-di-substituted azoalkanes of general formula, <FORM:0929182/IV(a)/1> in which each A is a group N3, -O(O)CH, -O(O)CR111, -S(O)CR11, -S(S)CR11, -O(O)COR111, -S(O)COR11, -S(S)COR11, -CN, -OCN, -SCN or -SR11 and R, R1 and R11 are aliphatic, araliphatic, aromatic, cycloaliphatic or heterocyclic groups with not more than 22 carbon atoms, or R and R1 taken together with the carbon atom to which they are attached form a cycloaliphatic or heterocyclic group, and R111 is an aliphatic group derived from the acid R111COOH or R111O.CO.OH which is liquid at 40 DEG C., and when A is a cyano group or an alkane carboxylic group R is an aromatic group (see Group IV(b)) and their use in the copolymerization of styrene and methyl methacrylate is mentioned. They may be used as rubber blowing agents and as an aid to vulcanization.ALSO:The invention comprises a ,a 1-disubstituted azoalkanes of general formula <FORM:0929182/IV(a)/1> in which each A is a group -N3, -O(O)CH, -O(O)CR111, -S(O)CR11, -S(S)CR11, -O(O)COR111, -S(O)COR11, -S(S)COR11, -CN, -OCN, -SCN, or -SR11, and R, R1, and R11 are aliphatic, araliphatic, aromatic, cycloaliphatic or heterocyclic groups with not more than 22 carbon atoms, or R and R1 taken together with the carbon atom to which they are attached form a cycloaliphatic or heterocyclic group, and R111 is an aliphatic group derived from an acid R111.COOM, or R111O.CO.OM which is liquid at 40 DEG C. and when A is a cyano group or an alkane carboxylic group R is an aromatic group, which are prepared by reacting an a ,a 1-dihalo azoalkane, <FORM:0929182/IV(a)/2> in which Hal is a halogen atom at a temperature below 40 DEG C. with a substance YA, in which Y is a cation such as an alkali metal, alkaline earth metal, or ammonium cation, and which undergoes double decomposition with the a ,a 1-dihaloazoalkane in the presence of a halogen acceptor, in the presence of a polar solvent. In a modified preparation of the compound in which A is an acyloxy or mono-esterified carbonate group a solution of a ketazine, RR1C=N-N=CRR1, in solution in an acid of general formula A1.OH in which A1 is an acyloxy or mono-esterified carbonate group, the acid being liquid at 40 DEG C. or below, in the presence of an ammonium or metal salt of the acid. R, R1 and R11 may be substituted, e.g. with halogen, nitro and cyano groups. Examples describe the preparation of 2,21-di-(formyloxy)-, 2,21-di(acetoxy)-, 2,21-di-(capronoxy), 2,21-di-(acetylthio)-, 2,21-di-(thiocyanato)-, 2,21-di(ethylthio)-, 2,21-di-(ethoxythiocarbonylthio)-2,21-di-(phenylthio) -, 2,21-di-(2-benzothiazolylthio), 2,21-di-(azido)-, 2,21-di(cyano)-2,21-azo propane; 2,21-di-(acetoxy)-2,21-azobutane; 3,31-di-(acetoxy)-3,31-azopentane; 2,21-di- (acetoxy)- 4,41-di-(methyl)-2, 21-azopentane; 1,11-diacetoxy-1,11-di-(phenyl)-, 1,11-di-(ethoxythiocarbonylthio)-1,11-di-phenyl- and 1,11-di-(thiocyanato)-1,11-di-phenyl- 1, 11-azoethane; 1,11-di- (acetoxy)-1,11-azocyclopentane; and 1,11-di-(acetoxy)-, 1,11-di-(thiocyanato)- and 1,11-di-(phenylthio)-1,11-azocyclohexane; and 1,11-di-(propionyloxy)-1,11-azocyclooctane, and other compounds mentoned are 1,1,11,11-tetraphenyl-1,11-di(acetoxy)-, and 1,1,1111-tetracyclohexyl-1,11-di(phenylmercapto) -1,1 azomethanes, 1,11-di(cyclohexyl)- 1,11-di(acetoxy)-1, 11-azoethane, 2,21-di(benzoxy)- and 2,21-di(cyanato)-2,21-azopropane and 1,11-di(acetoxy)-1,11-azocycloheptane. The compounds may be used as medicaments, photosensitisers, polymerisation catalyst and blowing agents, fungicides plant growth regulants and bactericides.ALSO:Blowing agents for rubber comprise a , a 1-disubstited azoalkanes of general formula <FORM:0929182/V/1> in which each A is a group N3, -O(O)CH, -O(O)CR111, -S(O)CR11, -S(S)CR11, -O(O)COR111, -S(O)COR11, -S(S)COR11, -CN, -OCN, -SCN or -SR11 and R, R1 and R11 are aliphatic, araliphatic, aromatic, cycloaliphatic, or heterocyclic groups with not more than 22 carbon atoms, or R and R1 taken together with the carbon atom to which they are attached form a cycloaliphatic or heterocyclic group and R111 is an aliphatic group derived from an acid R111 COOH or R111 O COOH which is liquid at 40 DEG C. and when A is a cyano group or a carboxylic group R is an aromatic group. (Group IVb). 2, 21-di- (2- benzothiazolylthio)- ,2 21-azopropane is an example of a blowing agent which also acts as a catalyst for the vulcanisation of rubber.
GB4350659A 1958-12-22 1959-12-22 Production of azoalkanes Expired GB929182A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH6762758A CH374700A (en) 1958-12-22 1958-12-22 Process for the preparation of α, α-dichloroazoalkanes
CH7113659 1959-03-16

Publications (1)

Publication Number Publication Date
GB929182A true GB929182A (en) 1963-06-19

Family

ID=25737921

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4350659A Expired GB929182A (en) 1958-12-22 1959-12-22 Production of azoalkanes

Country Status (1)

Country Link
GB (1) GB929182A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3306888A (en) * 1963-12-09 1967-02-28 Monsanto Co Azo compounds
US3962210A (en) * 1970-11-09 1976-06-08 Pennwalt Corporation Tertiary aliphatic alpha-(sulfo)-azo compounds
FR2403356A1 (en) * 1977-09-19 1979-04-13 Gustavsberg Ab PROCESS FOR EXTRUSION AND CROSS-LINKING OF OLEFINIC POLYMERS
FR2407235A1 (en) * 1977-10-31 1979-05-25 Pennwalt Corp CROSS-LINKING OF POLYMERS WITH AZOIC ESTERS

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3306888A (en) * 1963-12-09 1967-02-28 Monsanto Co Azo compounds
US3962210A (en) * 1970-11-09 1976-06-08 Pennwalt Corporation Tertiary aliphatic alpha-(sulfo)-azo compounds
FR2403356A1 (en) * 1977-09-19 1979-04-13 Gustavsberg Ab PROCESS FOR EXTRUSION AND CROSS-LINKING OF OLEFINIC POLYMERS
FR2407235A1 (en) * 1977-10-31 1979-05-25 Pennwalt Corp CROSS-LINKING OF POLYMERS WITH AZOIC ESTERS

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