GB884669A - Process for preparing ª--(hydroxyalkyl) hydrazinium salts - Google Patents
Process for preparing ª--(hydroxyalkyl) hydrazinium saltsInfo
- Publication number
- GB884669A GB884669A GB905059A GB905059A GB884669A GB 884669 A GB884669 A GB 884669A GB 905059 A GB905059 A GB 905059A GB 905059 A GB905059 A GB 905059A GB 884669 A GB884669 A GB 884669A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- prepared
- hydrazinium
- aryl
- phenyl
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
- C07D303/42—Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
- C08G59/4035—Hydrazines; Hydrazides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Epoxy Resins (AREA)
Abstract
A polymeric hydrazinium chloride of the possible structure <FORM:0884669/IV (a)/1> is prepared by reacting dimethylhydrazine hydrochloride with vinylcyclohexene dioxide and isolating the ethyl acetate soluble portion of the product. Other polymeric hydrazinium chlorides are prepared by the acylation of dialcoholic hydrazinium chlorides with dibasic acids or their reactive functional derivatives. Thus <FORM:0884669/IV (a)/2>ALSO:Beta-hydroxyalkyl-hydrazinium salts are prepared by reacting an oxirane with an acid-addition salt of a basic hydrazine in which at least one nitrogen atom has both its hydrogen atoms replaced by either two carbon atoms of one or two organic radicals singly bonded to the nitrogen atom or one carbon atom of an organic radical doubly bonded to the nitrogen atom. The reaction is preferably effected in an anhydrous alcoholic solvent (although other solvents, including water, may also be used) at temperatures between 10 DEG C. and 80 DEG C., and the product in each case is probably a mixture of isomers, as illustrated by the equation <FORM:0884669/IV (b)/1> wherein, for example, R1, R2, R3 and R4 can be hydrogen, alkyl, hydroxyalkyl, cycloalkyl, aryl, or aralkyl, or R1 and R2 or R4 together can form a mono- or bi-cyclo carbocyclic ring structure having no more than 7 annular members in a ring; R5 and R6 can be allyl, alkyl, phenylalkylene or hydroxyalky, or R5 and R6 together with the nitrogen atom on which they are both substituents can represent a 5, 6 or 7 membered heterocyclic ring, or when R6 is alkyl R5 can also be a benzene, nitrobenzene or chlorobenzene radical. Suitable oxiranes for use in the process include alkylene and cycloalkene oxides and dioxides which may contain additional double bonds, aryl and aralkyl radicals and hydroxy, halogen, carboxylic and esterified carboxylic, nitro, aroyl and trifluoromethyl atoms or groups. Suitable hydrazines include hydrazine di-, tri- and tetra-substituted by a variety of alkyl, alkenyl, cycloalkyl, aryl, aralkyl and alkanoyl groups, substituted semicarbazones, N-amino-pyrrolidine, -morpholine, -piperidine, -piperazines substituted by aryl, alkyl, amino and arayl groups, and -perhydroindoles, 2-methyl-1-phenyl-5-pyrazolidone, cyclohexylidene acetylidene azine, b -methoxy-propionaldehyde azine, and other hydrazones and azines of the formula R5.R6.C=N.NR7R8 and R5R6C=N.N=CR7R8 wherein R7 and R8 can be hydrogen, phenyl, benzyl, acyl, carbamoyl, thiocarbamoyl, mono-or di-nitro-phenyl, halophenyl, sulphophenyl or naphthyl, R5 can be hydrogen or alkyl, and R6 can be alkyl, phenyl, p-tolyl or benzyl, or R5 and R6 together can form a 5 or 6 membered ring. Specified anions, e.g. X-, include halides, sulphate, phosphate, nitrate, benzene-sulphonate, monomethyl sulphate and monophenyl phosphate. Examples illustrate many of the above features, the preparation of a mixture of <FORM:0884669/IV (b)/2> ; the formation of <FORM:0884669/IV (b)/3> by benzoylation of the corresponding dihydroxyhydrazinium chloride and of the dibenzoate of 1 : 1-bis(2-hydroxyethyl)-1-methyl hydrazinium chloride by a similar method; the formation of a mixture of <FORM:0884669/IV (b)/4> and <FORM:0884669/IV (b)/5> by the reaction of vinylcyclohexene dioxide with dimethyl hydrazine hydrochloride; and the formation of an unresolvable mixture of bisand tris-hydrazinium chlorides one of which has the probable structure <FORM:0884669/IV (b)/6> by the reaction of the glycerol tri-ester of acetoxy-epoxystearic acid with dimethyl hydrazine hydrochloride. 1-Methyl-1-benzyl-hydrazine hydrochloride is prepared from methylhydrazine and benzyl chloride. Dimethylhydrazine hydrochloride is prepared from the free base and concentrated hydrochloric acid, and is identified by conversion to the oxalate. Diethylhydrazine hydrobromide is prepared similarly.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB905059A GB884669A (en) | 1959-03-16 | 1959-03-16 | Process for preparing ª--(hydroxyalkyl) hydrazinium salts |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB905059A GB884669A (en) | 1959-03-16 | 1959-03-16 | Process for preparing ª--(hydroxyalkyl) hydrazinium salts |
Publications (1)
Publication Number | Publication Date |
---|---|
GB884669A true GB884669A (en) | 1961-12-13 |
Family
ID=9864435
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB905059A Expired GB884669A (en) | 1959-03-16 | 1959-03-16 | Process for preparing ª--(hydroxyalkyl) hydrazinium salts |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB884669A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0994142A1 (en) * | 1998-04-30 | 2000-04-19 | Otsuka Kagaku Kabushiki Kaisha | Hardener for epoxy resin |
-
1959
- 1959-03-16 GB GB905059A patent/GB884669A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0994142A1 (en) * | 1998-04-30 | 2000-04-19 | Otsuka Kagaku Kabushiki Kaisha | Hardener for epoxy resin |
EP0994142A4 (en) * | 1998-04-30 | 2001-01-17 | Otsuka Kagaku Kk | Hardener for epoxy resin |
US6359036B1 (en) | 1998-04-30 | 2002-03-19 | Otsuka Kagaku Kabushiki Kaisha | 1-Aminopyrrolidine or its salt as epoxy resin hardener |
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