GB1043025A - Cyanamido compounds and their preparation - Google Patents

Cyanamido compounds and their preparation

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Publication number
GB1043025A
GB1043025A GB13411/65A GB1341165A GB1043025A GB 1043025 A GB1043025 A GB 1043025A GB 13411/65 A GB13411/65 A GB 13411/65A GB 1341165 A GB1341165 A GB 1341165A GB 1043025 A GB1043025 A GB 1043025A
Authority
GB
United Kingdom
Prior art keywords
cyanogen
azide
cyanogen azide
polypivalolactone
cyclohexane
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
GB13411/65A
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and 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
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB1043025A publication Critical patent/GB1043025A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C261/00—Derivatives of cyanic acid
    • C07C261/02—Cyanates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
    • C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D203/16—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms
    • C07D203/20—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms by carbonic acid, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D203/26—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/22—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/12—1,4-Dioxanes; Hydrogenated 1,4-dioxanes not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/12—Hydrolysis
    • 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
    • C08G63/08—Lactones or lactides
    • 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/91—Polymers modified by chemical after-treatment
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/12—Chemical modification

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Compounds containing cyanamido groups are prepared by reacting organic compounds containing at least one carbon-hydrogen bond and free from carbon-carbon unsaturation with cyanogen azide at 25-150 DEG C. Cyanogen azide is explosive and should be prepared and reacted in a liquid medium, e.g. in situ in aliphatic compound or in a solvent such as acetonitrile, propionitrile, ethyl acetate, amyl acetate, dimethyl formamide, isooctane, tetrachlorethane, carbon tetrachloride, methylene chloride and dibromoethane. Specified organic compounds are cyclopropane, cycloheptane, cyclohexane, cyclooctane, decahydronaphthalene, nitrocyclohexane, chlorocyclohexane, cyclohexane carboxylic acid, cyclohexane carbonitrile, bicyclo [2.2.1]heptane, methane, propane, isooctane, dodecane, nonadecane, octadecane, 2,2,4-trimethylpentane, 1-nitrooctane, 2-chloropropane, t.-butyl chloride, ethyl acetate, octyl acetate, 1,4-dicyanobutane, sebacic acid, butyramide, dioxane, tetrahydrofuran, diethyl ether, ethylene glycol dimethyl ether and methyl ethyl ketone. The preparation of cyanogen azide from sodium azide and cyanogen chloride in acetonitrile is described and in examples cyanogen azide is reacted with (2) 2,3-dimethylbutane, (3) n-hexane, (4) 2,2-dimethylbutane, (5) methylcyclohexane, (6) cyclopentane, (7) cyclooctane, (8) methylcyclopentane, (9) 1,1-dimethylcyclohexane, mixtures of cyclohexane with (10) cycloheptane, (11) 2,2,3,3-tetramethylbutane, (12) bicyclo[2.2.1]heptane and (13) bicyclo[2.2.2]octane, (22) cyclohexane and (23) adamantine. Cyclohexylcyanamide prepared by (22) is hydrolysed to cyclohexylurea by aqueous sulphuric acid, and 1-cyanamidoadamantine prepared by (23) is hydrolysed to 1-aminoadamantine by refluxing with sodium hydroxide in diethylene glycol.ALSO:Organic polymers containing at least one C-H bond and free from C to C unsaturation are reacted with cyanogen azide at 25 DEG to 150 DEG C. Specified polymers are polyvinyl acetate, polyethylene, polypropylene, polyisobutylene, polystyrene, polymethyl vinyl ketone, polymethyl methacrylate, polymethyl acrylate, polyacrylonitrile, polyvinyl fluoride, polyvinylidene chloride, vinylidene fluoride/hexafluoropropylene copolymer, polyoxymethylenes, copolymers of formaldehyde with ethylene, propylene, ethylene oxide and trifluoroacetaldehyde, hydrogenated natural rubber, polypivalolactone and polymerized lactic and glycolic acids. Cyanogen azide is explosive and should be handled and the reaction effected in liquid media, e.g. acetonitrile, propionitrile, ethyl acetate, amyl acetate, dimethyl formamide, isooctane, tetrachlorethane, methylene chloride and dibromo-ethane. In examples, (1) polyvinyl fluoride, (14) polyethylene film, (15) polypropylene film, (16) non-woven polypropylene fabric, (17) polyvinyl fluoride film, (18) woven polypivalolactone fabric, (19) polypivalolactone powder, (20) an alkyl capped formaldehyde polymer, and (21) a vinylidene fluoride/hexafluoropropylene copolymer are treated with cyanogen azide in media comprising acetonitrile, ethyl acetate and/or methylene chloride. The products have improved dyeability.ALSO:The dye affinity of organic polymers containing at least one C-H bond and free from C-C unsaturation is increased by reacting the polymers with cyanogen azide at 25 to 150 DEG C. Cyanogen azide is explosive and should be prepared and reacted in a liquid medium, e.g. aliphatic hydrocarbons or halogenated hydrocarbons, esters, amides or nitriles. Specified polymers are polyvinyl esters and ketones, polyolefins, polystyrene, polyacrylic and polymethacrylic esters, polyacrylonitrile, vinyl and vinylidene halide polymers, polyoxymethylenes, copolymers of formaldehyde with ethylene, propylene, ethylene oxide and trifluoroacetaldehyde, hydrogenated natural rubber, polypivalolactone and polymerized lactic and glycollic acids. In examples (14) polyethylene film, (16) non-woven polypropylene fabric and (18) fabrics woven from polypivalolactone fibres are treated with solutions of cyanogen azide and subsequently dyed.
GB13411/65A 1964-07-16 1965-03-30 Cyanamido compounds and their preparation Expired GB1043025A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US38323364A 1964-07-16 1964-07-16

Publications (1)

Publication Number Publication Date
GB1043025A true GB1043025A (en) 1966-09-21

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ID=23512263

Family Applications (1)

Application Number Title Priority Date Filing Date
GB13411/65A Expired GB1043025A (en) 1964-07-16 1965-03-30 Cyanamido compounds and their preparation

Country Status (3)

Country Link
DE (2) DE1298096B (en)
FR (1) FR1436138A (en)
GB (1) GB1043025A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5637651A (en) * 1994-09-08 1997-06-10 Bp Chemicals Limited Process for modifying a polyolefin

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113307710B (en) * 2021-06-02 2022-05-27 南京理工大学 Porous azide/high-energy explosive micro-explosion sequence film and preparation method thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5637651A (en) * 1994-09-08 1997-06-10 Bp Chemicals Limited Process for modifying a polyolefin

Also Published As

Publication number Publication date
FR1436138A (en) 1966-04-22
DE1795204A1 (en) 1972-02-03
DE1298096B (en) 1969-06-26

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