GB783546A - Bis-mercaptomethyl aromatic compounds, their preparation and use - Google Patents
Bis-mercaptomethyl aromatic compounds, their preparation and useInfo
- Publication number
- GB783546A GB783546A GB36131/54A GB3613154A GB783546A GB 783546 A GB783546 A GB 783546A GB 36131/54 A GB36131/54 A GB 36131/54A GB 3613154 A GB3613154 A GB 3613154A GB 783546 A GB783546 A GB 783546A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bis
- mercaptomethyl
- compounds
- radical
- give
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Bis-mercaptomethyl compounds of formula HSCH2.Ar.CH2SH (see Group IV (b)), wherein Ar is a phenylene radical which may contain 1-4 methyl groups, may be condensed with bifunctional reagents to give resins. Compounds wherein the mercaptomethyl groups are in the para positions are preferred and give linear fibre-forming resins. Specified bifunctional reagents are diacids, diacid chlorides, diolefins, dialdehydes, acrylonitrile and vinyl trichlorsilane. The fibres may be cold-drawn to produce colourless filaments. Mixtures of two or more mercaptans and/or of bifunctional reagents, such as acid chlorides (e.g. adipyl+ sebacyl or terphthalyl chlorides), may be used to modify the properties of the resin. In examples: (1) bis-mercaptomethyl-2 : 3 : 5 : 6-tetramethyl-benzene was condensed with sebacyl chloride in the presence of nitrogen, the polyester product extruded and the resultant thread cold-drawn to give fibres; (2) as in (1) but using adipyl chloride or a mixture of adipyl and sebacyl chlorides; (3) as in (1) but condensing bis-mercaptomethyl-benzene with adipyl chloride.ALSO:Compounds of formula HSCH2.Ar.CH2SH are prepared from a starting material having the formula ZCH2.Ar.CH2Z, wherein Z is chlorine, bromine or iodine and Ar is a phenylene radical which may be substituted by 1-4 methyl groups, by preparing an intermediate by reacting 1 mol. of the starting material with 2 mols. of a compound having the formula <FORM:0783546/IV (a)/1> wherein Q is an amino radical NR2IV or a radical ORV and Y is an amino radical NR2IV or a thiol salt radical SM, RIV being hydrogen or an alkyl or aromatic radical containing 1-8 carbon atoms, RV being an alkyl or aromatic radical containing 1-8 carbon atoms and M being sodium, potassium or an ammonium radical and degrading the intermediate to the bismercaptan by hydrolysis with aqueous alkali when the intermediate is a thiouronium compound or by treatment with ammonia when the intermediate is a xanthate or a thiocarbamate or dithiocarbamate. The preferred compounds are those wherein the mercapto-methyl groups are in the para-positions and such compounds may be condensed with bifunctional reagents to give linear polymers (see Group IV (a)). Specified bis-halomethyl compounds are bis - chloromethyl - 2 : 3 : 5 : 6 - tetramethylbenzene, para - bis - chloromethyl - benzene, 2 : 5 - bis - chloromethyl - 1 : 4 - dimethylbenzene and bis-halomethylated mixed xylenes. Specified compounds of formula <FORM:0783546/IV (a)/2> are thiourea, sodium dithiocarbamate, potassium ethyl xanthate, tetramethyl thiourea, ammonium di-isopropyl dithiocarbamate, phenyl diphenylthiocarbamate and sodium octyl xanthate. In examples: (1) bis-chloromethyldurene (i.e. bis-chloromethyl-2 : 3 : 5 : 6-tetramethylbenzene) was reacted with thiourea to give a thiouronium compound which was hydrolysed to bis-mercaptomethyl-durene with an aqueous alcohol solution of potassium hydroxide; (2) bis-chloromethyl-durene was reacted with potassium ethyl xanthate to give bis-ethylxanthomethyl-durene which was converted to bis-mercaptomethyl-durene by treatment with alcoholic ammonia.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US783546XA | 1954-01-20 | 1954-01-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB783546A true GB783546A (en) | 1957-09-25 |
Family
ID=22143502
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB36131/54A Expired GB783546A (en) | 1954-01-20 | 1954-12-14 | Bis-mercaptomethyl aromatic compounds, their preparation and use |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB783546A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1184147B (en) * | 1960-05-09 | 1964-12-23 | Shell Int Research | Preparations for the control of nematodes |
-
1954
- 1954-12-14 GB GB36131/54A patent/GB783546A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1184147B (en) * | 1960-05-09 | 1964-12-23 | Shell Int Research | Preparations for the control of nematodes |
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