BE531090A - Procédé pour la production de dérivés substitués du 1-3-4-thiadiazol - Google Patents

Procédé pour la production de dérivés substitués du 1-3-4-thiadiazol

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Publication number
BE531090A
BE531090A BE531090A BE531090A BE531090A BE 531090 A BE531090 A BE 531090A BE 531090 A BE531090 A BE 531090A BE 531090 A BE531090 A BE 531090A BE 531090 A BE531090 A BE 531090A
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BE
Belgium
Prior art keywords
emi
parts
substituted
production
compound
Prior art date
Application number
BE531090A
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English (en)
Inventor
Dr Hans Krzikalla
Dr Heinz Pohlemann
Original Assignee
Basf Ag
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.)
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Publication date
Application filed by Basf Ag filed Critical Basf Ag
Publication of BE531090A publication Critical patent/BE531090A/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
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    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
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    • C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
    • C04B35/01—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on oxide ceramics
    • C04B35/46—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on oxide ceramics based on titanium oxides or titanates
    • C04B35/462—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on oxide ceramics based on titanium oxides or titanates based on titanates
    • C04B35/465—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on oxide ceramics based on titanium oxides or titanates based on titanates based on alkaline earth metal titanates
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
    • C08G12/06—Amines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
    • C08G12/10—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with acyclic compounds having the moiety X=C(—N<)2 in which X is O, S or —N
    • C—CHEMISTRY; METALLURGY
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
    • C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
    • C08G79/06—Phosphorus linked to carbon only
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    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/45—Heterocyclic compounds having sulfur in the ring
    • C08K5/46—Heterocyclic compounds having sulfur in the ring with oxygen or nitrogen in the ring
    • C—CHEMISTRY; METALLURGY
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    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/45—Heterocyclic compounds having sulfur in the ring
    • C08K5/46—Heterocyclic compounds having sulfur in the ring with oxygen or nitrogen in the ring
    • C08K5/47—Thiazoles
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/3481—Organic compounds containing sulfur containing sulfur in a heterocyclic ring, e.g. sultones or sulfolanes
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/349—Organic compounds containing sulfur additionally containing nitrogen atoms, e.g. nitro, nitroso, amino, imino, nitrilo, nitrile groups containing compounds or their derivatives or thio urea
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
    • C23F11/16—Sulfur-containing compounds
    • C23F11/165—Heterocyclic compounds containing sulfur as hetero atom
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G1/00—Cleaning or pickling metallic material with solutions or molten salts
    • C23G1/14—Cleaning or pickling metallic material with solutions or molten salts with alkaline solutions
    • C23G1/16—Cleaning or pickling metallic material with solutions or molten salts with alkaline solutions using inhibitors
    • C23G1/18—Organic inhibitors
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423—Amino-aldehyde resins
    • D06M15/43—Amino-aldehyde resins modified by phosphorus compounds
    • D06M15/431—Amino-aldehyde resins modified by phosphorus compounds by phosphines or phosphine oxides; by oxides or salts of the phosphonium radical
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106—Thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
    • C10M2223/121—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy of alcohols or phenols
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    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
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Description


  La présente invention a pour objet de nouveaux dérivés précieux

  
 <EMI ID=1.1> 

  
substitué, par exemple un groupe carboxylé saturé, aliphatique au cycloaliphatique, avec 5 à 18 atomes de carbone La valence encore libre peut être . saturée par un atome d'hydrogène, un équivalent d'un métal ou d'une base, un radical d'hydrocarbure éventuellement substitué, aliphatique, cycloali-

  
 <EMI ID=2.1>  <EMI ID=3.1> 

  
hydrazine, on peut dans ce cas, également utiliser les solutions d'hydrazines brutes techniques, très étendues et déjà fortement alcalineso

  
La production des composés qui renferment le groupement -S-

  
 <EMI ID=4.1> 

  
des composés de formule générale halg-X-Y, halg représentant un halogénure et X et Y les groupes mentionnés plus hauto Des composés de ce genre sont, par exemple, les chlorures, bromures et iodures d'hydrocarbures saturés aliphatiques, des acides carboxyliques ou des acides sulf oni que s comportant entre 6 et 18 atomes de carbone, lesquels peuvent être disposés en chaîne

  
 <EMI ID=5.1> 

  
ments, tels que des groupes carboxylèo Des composés appropriés de formule. halg-X-Y sont, par exemple, les chlorures, bromures ou iodures d'hexyle  d'heptyle, de n-octyle, de 2-éthyl-n-hexyle, de dodécyle, d'huile de spermacéti, d'octadécyle.. les chlorures ou bromures d'acide éthylhexanique, d'acide gras d'huile de spermacéti, d'acide palmique, d'acide décylsulfonique ou d' acide undécylsulfoniqueo '

  
On effectue la réaction en milieu faiblement acide à alcalin, donc dans un intervalle de pH compris entre 4 et 11, dans des diluants tels

  
 <EMI ID=6.1> 

  
diluants sont également appropriéso On opère avantageusement en milieu neutre, de préférence en milieu alcalin, en utilisant pour la mise en-point du

  
 <EMI ID=7.1> 

  
former, selon des méthodes connues en soi, en sels métalliques, par exemple de métaux, tels que le zinc, le baryum, le magnésium, le fer, le plomb ou

  
 <EMI ID=8.1> 

  
en solution alcoolique, du peroxyde d'hydrogène, de l'eau de Javel ou du chlore 

  
En faisant réagir des composés bifontionnels aliphatiques ou

  
 <EMI ID=9.1> 

  
solubles dans les huiles particulièrement précieux et pouvant être utilisés de façon avantageuse comme plastifiants pour le chlorure de polyvinyle et d&#65533;autres matières plastiques. On peut également les ajouter aux agents de nettoyage alcalins contenant du phosphate pour éviter la corrosion ou le ternissement des métaux, ou bien les utiliser comme agents de mouillage et comme détersifs, au encore comme agents hydrophobeso Etant donné qu'ils sont très efficaces comme détergents et comme inhibiteurs d'oxydation, on peut aussi les utiliser comme produits d'addition pour lubrifiants, notamment

  
 <EMI ID=10.1> 

  
encore comme accélérateurs de vulcanisation et pour empêcher la corrosion provoquée par des tensions.

  
Les exemples suivants donnés à titre indicatif, mais nullement limitatif, expliqueront la présente invention plus en détailso

  
Les parties indiquées sont des parties en poids.

  
 <EMI ID=11.1> 

  
 <EMI ID=12.1> 

  
600 parties de méthanol, on ajoute une solution de 24 parties en soude caustique dans 40 parties d'eau, ainsi que 88,8 parties de chlorure de n=octyle puis on chauffe pendant 2 à 3 heures au réf régérant à reflux. On entraîne le méthanols, dans une large mesure, par distillation, on verse dans de l'eau glacée

  
 <EMI ID=13.1> 

  
dans l'huile et qui, grâce à son point de fusion avantageux, ne donne pas lieu, lors de Inapplication, à la précipitation cristalline, souvent fort gênante

  
 <EMI ID=14.1>  ...Comparé aux produits antisolaires connus jusqu'ici, qui possèdent des facteurs de protection antisolaire d'environ 2,5, celui de ce composé est d'environ 4, lors de l'emploi d'une émulsion aqueuse à 5% et d'environ 6 si <EMI ID=15.1> 

  
thylate de sodium méthanolique à 30% et en opérant pour le reste comme indiqué plus haute

  
Lorsqu'on remplace les 88,8 parties de chlorure de n-octyle par

  
 <EMI ID=16.1> 

  
stance.. peut, par exemple, être particulièrement bien utilisée comme plastifiant pour le chlorure de polyvinyle (PVC)  Des feuilles de chlorure de polyvinyle ainsi préparées, qui

  
 <EMI ID=17.1> 

  

 <EMI ID=18.1> 


  
EXEMPLE 2 

  
 <EMI ID=19.1> 

  
400 parties d'alcool, on ajoute une solution de 16 parties de soude caustique dans 40 parties d'eau et de 100 parties de bromure de dodécyle;, puis on chauffe pendant deux heures au réfrigérant à refluxo On verse dans 1500

  
 <EMI ID=20.1> 

  
produit antisolaire efficace. 

  
 <EMI ID=21.1> 

  
 <EMI ID=22.1> 

  
le, puis on chauffe pendant deux heures au refluxo On verse dans 2000 parties d'eau glacée on essore les cristaux précipités et on recristallise

  
 <EMI ID=23.1> 

  
ment, on obtient également de bons rendements de ce composée Sous forme de son sel de baryum ou de zinc, le produit est très efficace comme détergent et inhibiteur d'oxydation pour les lubrifiants.

  
 <EMI ID=24.1> 

  
3-4-thiadiazol dans 300 parties d'alcool et on ajoute une solution de 8 parties de soude caustique dans 30 parties d'eau; On introduit lentement dans ce mélange, par petites portions, à la température ambiante, une solution

  
 <EMI ID=25.1> 

  
d'un composé blanc (point de fusion = 74[deg.] )o Le rendement est quantitatif 

  
L'oxydation pour l'obtention de ^sulfure peut être effectuée

  
 <EMI ID=26.1> 

  
chloreo Les rendements sont également très bonso

  
Le composé disulfuré convient, par exemple, très bien comme produit antisolaireo 

  
 <EMI ID=27.1> 

  
 <EMI ID=28.1>  

  
Le composé disulfuré constitue également un bon accélérateur de la vulcanisation et fournit des articules vulcanisés possédant de bonnes

  
 <EMI ID=29.1> 

  
10 parties oxyde :de zinc

  
3 parties soufre

  
 <EMI ID=30.1> 

  
thiadiazol) 

  
Les articles vulcanisés possèdent les propriétés mécaniques suivantes s

  
 <EMI ID=31.1> 

  
gement à la rupture = 792 " Elasticité de rebondissement = 62 

  
 <EMI ID=32.1> 

  
tant 30 parties d'hydroxyde de zinc, en chauffant à 1500' et en portant la température -en ]/espace d'une heure à 200[deg.] et ensuite brièvement à 250[deg.]on obtient un produit qui après filtrage, convient parfaitement bien pour. améliorer les lubrifiants. Une huile pour moteurs acquiert les propriétés

  
 <EMI ID=33.1> 

  
stéerylique avec du pentasulfure de phosphore On peut, de façon analogue, également préparer et utiliser le sel de baryum du composée

  
 <EMI ID=34.1> 

  
comme produit antisolaire qui absorbe toute la lumière ultraviolette, ainsi que comme accélérateur de vulcanisation,,

  
 <EMI ID=35.1> 

  
 <EMI ID=36.1> 

  
 <EMI ID=37.1> 

  
diazol sous forme d'un sirop brun verdatreo Le composé est un très bon accélérateur de vulcanisation, qui agit de manière particulièrement rapide. Le "plateau" et la résistance au vieillissement sont très bonso On a, par exem-

  
 <EMI ID=38.1> 

  
1,5 partie acide stéarique

  
10 parties oxyde de zinc

  
3 parties soufre  <EMI ID=39.1> 

  
Le produit vulcanise- ainsi obtenu présente les propriétés mécaniques suivantes 

  
 <EMI ID=40.1> 

  
Résistance à la rupture = 229 Allongement à la rupture = 632 

  
 <EMI ID=41.1> 

  
Le très bon "plateau" de l'accélérateur ressort du tableau suivant g 

  

 <EMI ID=42.1> 


  
1229-L-E -5-0

  
 <EMI ID=43.1> 

  
Le composé de sodium possède de très bonnes propriétés de lavage et de mouillage. 

  
 <EMI ID=44.1> 

  
chauffe pendant une heure à l'ébullition au réfrigérant à reflux et on verse dans 2000 parties d'eau glacée. Après essorage et recristallisation

  
 <EMI ID=45.1> 

  
d'huile de spermacéti du chlorure d'huile de spermacéti d'acide gras  du chlorure d'acide 2-éthylhexanique, du chlorure d'acide décyl- ou un-

  
 <EMI ID=46.1> 

  
coté peuvent 'également être transformés en disulfures ou en leurs sels. 

EXEMPLE 

  
 <EMI ID=47.1> 

  
750 parties d'alcool, 40 parties de soude caustique et 60 parties d'eau, on refroidit avec de l'eau glacée et on ajoute lentement,'en brassant convena-

  
 <EMI ID=48.1> 

  
 <EMI ID=49.1> 

  
2 heures au réfrigérant à refluxo On verse le mélange réactionnel dans deux litres d'eau glacée, 

  
Il se précipite une huile brun rougeâtre qu'on dissout dans

  
de la lessive de soude diluée On ajoute, en refroidissant à la glace, de

  
1^ acide chlorhydrique dilué et on essore le composé qui précipite alors et

  
 <EMI ID=50.1> 

  
ture ambiante et on fait bouillir pendant deux heures au réfrigérant à re=

  
flux. On verse dans 4 litres d'eau glacée et on obtient 120 parties de 5-

  
 <EMI ID=51.1> 

  
poisseuxo On dissout ces derniers dans un peu de méthanol et on obtient,

  
par congélation dans un mélange frigorifique, des cristaux jaunes de point

  
 <EMI ID=52.1> 

  
heures au réfrigérant à reflux, on évapore l'alcool dans une large mesure,

  
puis? après le refroidissement, on ajoute de l'acide chlorhydriqueo On

  
 <EMI ID=53.1> 

  
au moins 6 atomes de carbone en liaison aliphatiqueo

Claims (1)

  1. <EMI ID=54.1>
    <EMI ID=55.1>
    comportant moins de 6 atomes de carbone <EMI ID=56.1>
BE531090A 1953-08-20 1954-08-12 Procédé pour la production de dérivés substitués du 1-3-4-thiadiazol BE531090A (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB27085A DE953607C (de) 1953-08-20 1953-08-20 Verfahren zur Herstellung von Mono- oder Disubstitutionsprodukten des 2, 5-Dimercapto-1, 3, 4-thiadiazols

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BE531090A true BE531090A (fr) 1954-08-31

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BE (1) BE531090A (fr)
DE (1) DE953607C (fr)
FR (1) FR1109927A (fr)

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Publication number Priority date Publication date Assignee Title
US2836564A (en) * 1954-10-28 1958-05-27 Standard Oil Co Corrosion inhibitors and compositions containing the same
BE548233A (fr) * 1955-06-03
DE1095838B (de) * 1957-04-10 1960-12-29 Dehydag Gmbh Verfahren zur Herstellung sulfoalkylierter heterocyclischer Verbindungen
US2983716A (en) * 1958-03-26 1961-05-09 Standard Oil Co Rubber vulcanization acceleration
FR1205353A (fr) * 1959-06-25 1960-02-02 Du Pont Stabilisation des colorants contre la photodégradation
NL263273A (fr) * 1960-04-07
BE606550A (fr) * 1960-07-27
US4107168A (en) * 1975-07-24 1978-08-15 Mobil Oil Corporation Phosphorus substituted dimercapto thiadiazoles
GB1536593A (en) * 1976-06-28 1978-12-20 Hercules Inc Vulcanizing halogen-containing polymers
US4210544A (en) * 1976-08-18 1980-07-01 Texaco Inc. Dual purpose cutting oil composition
US4097387A (en) * 1976-09-03 1978-06-27 Standard Oil Company (Indiana) Olefin-dimercapto-thiadiazole compositions and process
US4990273A (en) * 1985-09-30 1991-02-05 Union Oil Company Of California Lubrication anti-wear additive
US4711915A (en) * 1986-04-07 1987-12-08 R. T. Vanderbilt Company, Inc. Surface coating compositions containing substituted 1,3,4-thiadiazoles
US4761482A (en) * 1987-04-23 1988-08-02 R. T. Vanderbilt Company, Inc. Terpene derivatives of 2,5-dimercapto-1,3,4-thiadiazoles and lubricating compositions containing same
US4795479A (en) * 1988-05-02 1989-01-03 R. T. Vanderbilt Company, Inc. Fuel compositions containing terpene derivatives of 2,5-dimercapto-1,3,4-thiadiazole
US4904403A (en) * 1989-06-12 1990-02-27 R. T. Vanderbilt Company, Inc. Polyalkylated 1,3,4-thiadiazoles and lubricating compositions containing same
US5171861A (en) * 1990-10-29 1992-12-15 Mobil Oil Corporation Thiadiazole-aryl sulfonate reaction products as multifunctional additives and compositions containing same
US5773523A (en) * 1995-12-14 1998-06-30 R.T. Vanderbilt Company, Inc. 1,3,4-thidiazole ether curing systems for chlorine containing polymers
US6613411B2 (en) 2001-01-25 2003-09-02 3M Innovative Properties Company Conformable multi-layer sheet materials
CN103319435B (zh) * 2012-03-22 2016-01-20 中国石油天然气股份有限公司 一种双噻二唑衍生物及其制备方法
CA3150299A1 (fr) 2019-09-17 2021-03-25 Paul E. Adams Derives de 2,5-dimercapto-1,3,4-thiadiazole ("dmtd")
WO2022046718A1 (fr) 2020-08-26 2022-03-03 The Lubrizol Corporation Dérivés de sels de zinc de 2,5-dimercapto-1,3,4-thiadiazole (dmtd)
US20230312496A1 (en) 2020-08-26 2023-10-05 The Lubrizol Corporation 2,5-Dimercapto-1,3,4-Thiadiazole (DMTD) Metal Salt Derivatives

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE840155C (de) * 1950-05-15 1952-05-29 Hoechst Ag Verfahren zur Stabilisierung von Polyvinylacetalen

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FR1109927A (fr) 1956-02-03
DE953607C (de) 1956-12-06
US2736729A (en) 1956-02-28

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