BE620530A - - Google Patents

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Publication number
BE620530A
BE620530A BE620530DA BE620530A BE 620530 A BE620530 A BE 620530A BE 620530D A BE620530D A BE 620530DA BE 620530 A BE620530 A BE 620530A
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BE
Belgium
Prior art keywords
emi
salts
molecular weight
acid
ethylene oxide
Prior art date
Application number
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French (fr)
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.)
Publication of BE620530A publication Critical patent/BE620530A/fr

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/463Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55Phosphorus compounds
    • A61K8/556Derivatives containing from 2 to 10 oxyalkylene groups
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/10Washing or bathing preparations
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00Sulfonic acids; Halides, esters, or anhydrides thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/06Phosphorus compounds without P—C bonds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/06Phosphorus compounds without P—C bonds
    • C07F9/08Esters of oxyacids of phosphorus
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/06Phosphorus compounds without P—C bonds
    • C07F9/08Esters of oxyacids of phosphorus
    • C07F9/09Esters of phosphoric acids
    • C07F9/10Phosphatides, e.g. lecithin
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/143Sulfonic acid esters
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/146Sulfuric acid esters
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/22Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Dermatology (AREA)
  • Detergent Compositions (AREA)

Description

       

   <EMI ID=1.1> 

  
l'action d'acides minéraux sur des composés organiques à poids moléculaira élevé. 

  
Les sels utilisés dans la pratique, en particulier

  
 <EMI ID=2.1> 

  
les sels alcalins des produit" acides de l'action d'acides mi- .  néraux sur des composés organiques' à poids moléculaire élevé,

  
 <EMI ID=3.1> 

  
concentrés ou anhydres de ce genre présente un intérêt pratique", on a choisi l'expédient de convertir ces matière" en une forme  <EMI ID=4.1> 

  
etc. 

  
 <EMI ID=5.1>  , {des :.- sels liquides limpides des produits acides de l'action d'acides minéraux sur des composés organiques à poids moléculaire élevé lorsqu'on neutralise ces composés acides avec des aminés  alcoxylées. Ces sels possèdent une importance pratique pour la préparation d'agents pour soins corporels, en particulier pour  le lavage des cheveux et pour les préparations moussantes pour

  
 <EMI ID=6.1> 

  
 <EMI ID=7.1> 

  
parce qu'ils se dissolvent aisément dans l'eau et fournissent  ^ sans difficulté des solutions aqueuses même à très haute concen-

  
 <EMI ID=8.1> 

  
particulièrement faible envers les sels, si bien qu'on peut les, employer avec un avantage particulier en association avec des solutions aqueuses d'électrolytes. En outre, dans le test des ^ferments, par exemple avec la saccharase, ils s'avèrent consi-  durablement moins nocifs que les sels correspondnants obtenus à .partir d'aminés non alcoxylées. D'après l'expérience, on peut  en conclure que les sels conformes à l'invention sont mieux  tolères par l'épiderme que les sels d'aminés usuels,

  
Parmi les produits acides de l'action d'acides

  
 <EMI ID=9.1> 

  
 <EMI ID=10.1> 

  
 <EMI ID=11.1> 

  
ment les alcoyl phosphates ou -borates acides correspondants.

  
Les produits de réaction cités peuvent dériver de composés ali-

  
 <EMI ID=12.1> 

  
rompus dans la chaîne carbonée par des hétéroatomes ou groupes

  
 <EMI ID=13.1> 

  
 <EMI ID=14.1>  

  
 <EMI ID=15.1> 

  
les acides alcoylbenzène- ou -naphtalène-sulfoniques avec des

  
 <EMI ID=16.1> 

  
et dialcoylés, les esters boriques acides alcoylés, ainsi

  
 <EMI ID=17.1> 

  
peuvent contenir aussi des substituants,.- en particulier des substituants hydroxyle, ou des amines tertiaires surtout à poids moléculaire inférieur qui présentent des substituants hydroxyle, On peut toutefois employer aussi comme agents de neutralisation des alcoylamines à poids moléculaire élevé qui se prêtent à

  
 <EMI ID=18.1> 

  
tion, on fixe des quantités relativement faibles de 1 Il 12 moles, de préférence de 3 à 6 moles d'oxyde d'alcoylène comme l'oxyde

  
 <EMI ID=19.1> 

  
 <EMI ID=20.1> 

  
 <EMI ID=21.1> 

  
Au tours de dette addition, on obtient en général des produits 

  
 <EMI ID=22.1> 

  
 <EMI ID=23.1>  

  
La neutralisation des produits précités acides de 

  
 <EMI ID=24.1> 

  
: moléculaire élevé avec les bases aminées citées plus haut se  <EMI ID=25.1>  <EMI ID=26.1> 

  
des à l'état très concentré anhydre, qu'ils se laissent diluer  sans difficulté avec de l'eau et qu'ils donnent des solutions 

  
 <EMI ID=27.1> 

  
sels. 

  
On peut aussi combiner les sels obtenus avec d'autres substances tensio-actives et/ou avec les additifs connus  pour de telles matières, comme par exemple des agents auxiliai- 

  
 <EMI ID=28.1> 

  
lement les produits d'addition de l'oxyde d'éthylène sur des  Composés à-poids moléculaire élevé ayant des atomes d'hydrogène  échangeables et les alcanolamides d'acides gras. Des agents  auxiliaires de lavage connus sont par exemple les carbonates,  sulfates, silicates, phosphates, borates,alcalins, la méthylcel-  lulose, les sels d'acides cellulose-éther-carboxyliques, etc.

  
 <EMI ID=29.1> 

  
sables avantageusement dans l'industrie des agents auxiliaires des textiles, du cuir et du papier, en outre dans l'industrie
-.des laques et des matières artificielles, ainsi que comme agents de rinçage et de nettoyage, 

Exemple 1, 

  
Dans le tableau ci-après, on indique les matières 

  
 <EMI ID=30.1> 

  
 <EMI ID=31.1> 

  
 <EMI ID=32.1> 

  
 <EMI ID=33.1>  
 <EMI ID=34.1> 
  <EMI ID=35.1> 

  
est tout d'abord sulfaté avec la quantité indiquée d'acide chlorosulfonique de la manière courante, puis on ajoute l'ester acide obtenu progressivement à la base aminée tout en refroi-

  
 <EMI ID=36.1> 

  
 <EMI ID=37.1> 

  
refroidissement.

  
Exemple [pound].-

  
 <EMI ID=38.1> 

  
 <EMI ID=39.1> 

  
 <EMI ID=40.1> 

  
 <EMI ID=41.1> 

  
 <EMI ID=42.1> 

  
limpide qui se dissout avec limpidité dans l'eau.

  
 <EMI ID=43.1> 

  
queux et dissolvable avec limpidité dans l'eau lorsqu'on neu-

  
 <EMI ID=44.1> 

  
d'oxyde d'éthylène sur 1 mole de triéthanolamine,

  
 <EMI ID=45.1> 

  
On fait agir sur 41 g d'un mélange d'alcools gras

  
 <EMI ID=46.1> 

  
 <EMI ID=47.1> 

  
phosphate d'alcool gras est un produit liquide limpide faiblement coloré en jaune.

  
 <EMI ID=48.1> 

  
 <EMI ID=49.1> 

  
 <EMI ID=50.1> 

  
 <EMI ID=51.1> 

  
pentoxyde de phosphore dans chaque cas et que l'on neutralise ; les esters acides obtenus avec 49 g et respectivement 52 g du  <EMI ID=52.1> 

  
de triéthanolamine. 

  
 <EMI ID=53.1> 

  
1.- Procédé de préparation de sels liquides. de

  
 <EMI ID=54.1> 

  
 <EMI ID=55.1> 

  
neutralise ces produits de réaction avec des produits d'addi- -  tion d'oxyde d'alcoylène sur des aminés,



   <EMI ID = 1.1>

  
the action of mineral acids on organic compounds of high molecular weight.

  
The salts used in practice, in particular

  
 <EMI ID = 2.1>

  
alkali metal salts of the acidic products of the action of mineral acids on organic compounds of high molecular weight,

  
 <EMI ID = 3.1>

  
such concentrates or anhydrous are of practical interest "the expedient has been chosen to convert this material" into a form <EMI ID = 4.1>

  
etc.

  
 <EMI ID = 5.1>, {des: .- Clear liquid salts of acid products of the action of mineral acids on organic compounds of high molecular weight when neutralizing these acid compounds with alkoxylated amines. These salts are of practical importance for the preparation of agents for body care, in particular for washing the hair and for foaming preparations.

  
 <EMI ID = 6.1>

  
 <EMI ID = 7.1>

  
because they dissolve easily in water and easily provide aqueous solutions even at very high concentrations.

  
 <EMI ID = 8.1>

  
particularly weak towards salts, so that they can be used with particular advantage in combination with aqueous solutions of electrolytes. In addition, in the test for ferments, for example with sucrase, they are found to be considerably less harmful than the corresponding salts obtained from non-alkoxylated amines. From experience, it can be concluded that the salts in accordance with the invention are better tolerated by the epidermis than the usual amine salts,

  
Among the acid products of the action of acids

  
 <EMI ID = 9.1>

  
 <EMI ID = 10.1>

  
 <EMI ID = 11.1>

  
ment the corresponding alkyl phosphates or acid-borates.

  
The reaction products mentioned can be derived from ali-

  
 <EMI ID = 12.1>

  
broken in the carbon chain by heteroatoms or groups

  
 <EMI ID = 13.1>

  
 <EMI ID = 14.1>

  
 <EMI ID = 15.1>

  
alkylbenzene- or -naphthalenesulfonic acids with

  
 <EMI ID = 16.1>

  
and dialkylated, alkylated acid boric esters, as well

  
 <EMI ID = 17.1>

  
may also contain substituents, in particular hydroxyl substituents, or especially lower molecular weight tertiary amines which have hydroxyl substituents.

  
 <EMI ID = 18.1>

  
tion, relatively small amounts of 1 to 12 moles, preferably 3 to 6 moles of alkylene oxide such as the oxide are fixed.

  
 <EMI ID = 19.1>

  
 <EMI ID = 20.1>

  
 <EMI ID = 21.1>

  
In debt addition turns, we generally obtain products

  
 <EMI ID = 22.1>

  
 <EMI ID = 23.1>

  
The neutralization of the aforementioned acidic products of

  
 <EMI ID = 24.1>

  
: high molecular with the amino bases mentioned above se <EMI ID = 25.1> <EMI ID = 26.1>

  
in the highly concentrated anhydrous state, that they can be diluted without difficulty with water and that they give solutions

  
 <EMI ID = 27.1>

  
salts.

  
It is also possible to combine the salts obtained with other surface-active substances and / or with the additives known for such materials, such as, for example, auxiliary agents.

  
 <EMI ID = 28.1>

  
They are also the adducts of ethylene oxide on high molecular weight compounds having exchangeable hydrogen atoms and the alkanolamides of fatty acids. Known washing aids are, for example, carbonates, sulphates, silicates, phosphates, borates, alkalis, methylcellulose, salts of cellulose-ether-carboxylic acids, etc.

  
 <EMI ID = 29.1>

  
sands advantageously in the textile, leather and paper auxiliary agent industry, in addition in the industry
- lacquers and artificial materials, as well as rinsing and cleaning agents,

Example 1,

  
In the table below, we indicate the materials

  
 <EMI ID = 30.1>

  
 <EMI ID = 31.1>

  
 <EMI ID = 32.1>

  
 <EMI ID = 33.1>
 <EMI ID = 34.1>
  <EMI ID = 35.1>

  
is first sulphated with the indicated quantity of chlorosulphonic acid in the usual way, then the acid ester obtained is gradually added to the amino base while cooling

  
 <EMI ID = 36.1>

  
 <EMI ID = 37.1>

  
cooling.

  
Example [pound] .-

  
 <EMI ID = 38.1>

  
 <EMI ID = 39.1>

  
 <EMI ID = 40.1>

  
 <EMI ID = 41.1>

  
 <EMI ID = 42.1>

  
limpid which dissolves with clarity in water.

  
 <EMI ID = 43.1>

  
queux and dissolvable with clarity in water when new

  
 <EMI ID = 44.1>

  
ethylene oxide on 1 mole of triethanolamine,

  
 <EMI ID = 45.1>

  
We act on 41 g of a mixture of fatty alcohols

  
 <EMI ID = 46.1>

  
 <EMI ID = 47.1>

  
Fatty Alcohol Phosphate is a clear liquid product with weak yellow color.

  
 <EMI ID = 48.1>

  
 <EMI ID = 49.1>

  
 <EMI ID = 50.1>

  
 <EMI ID = 51.1>

  
phosphorus pentoxide in each case and neutralized; the acid esters obtained with 49 g and 52 g respectively of <EMI ID = 52.1>

  
of triethanolamine.

  
 <EMI ID = 53.1>

  
1.- Process for the preparation of liquid salts. of

  
 <EMI ID = 54.1>

  
 <EMI ID = 55.1>

  
neutralizes these reaction products with adducts of alkylene oxide on amines,


    

Claims (1)

<EMI ID=56.1> <EMI ID = 56.1> <EMI ID=57.1> <EMI ID = 57.1> préférence à bas poids moléculaire sur lesquelles est fixé de l'oxyde d'éthylène, ; preferably low molecular weight to which ethylene oxide is attached; 3.- ProcédS suivant les revendications 1 et 2, caractérisé en ce qu'on neutralise les produits acides de réaction d'acides minéraux avec des produits d'addition de 1 à 12 et de préférence 3 à 6 moles d'oxyde d'éthylèno sur des aminos primaires, secondaires ou sur des aminés tertiaires hydroxy- substituées. 3.- Processes according to claims 1 and 2, characterized in that neutralizes the acidic reaction products of mineral acids with adducts of 1 to 12 and preferably 3 to 6 moles of ethylene oxide on primary or secondary aminos or on hydroxy-substituted tertiary amines.
BE620530D 1961-07-24 BE620530A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DED0036644 1961-07-24

Publications (1)

Publication Number Publication Date
BE620530A true BE620530A (en)

Family

ID=7043212

Family Applications (1)

Application Number Title Priority Date Filing Date
BE620530D BE620530A (en) 1961-07-24

Country Status (4)

Country Link
BE (1) BE620530A (en)
CH (1) CH418326A (en)
DE (1) DE1443250A1 (en)
NL (1) NL281270A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2121325A1 (en) * 1971-04-30 1972-11-09 Methoxypropionitrile prepn - from acrylonitrile and methanol using triethanolamine and ethylene oxide reaction prod as catalyst

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2538279C3 (en) * 1975-08-28 1981-11-12 Zschimmer & Schwarz Gmbh & Co Chemische Fabriken, 5420 Lahnstein Use of sulfated and neutralized mixtures of mono- and dialkylbenzenes for brush or bath lubrication of material containing collagen fibers
DE4443643A1 (en) * 1994-12-08 1996-06-13 Henkel Kgaa Prepn. of anionic glucamide detergents without strong oxidn. of sugar components

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2121325A1 (en) * 1971-04-30 1972-11-09 Methoxypropionitrile prepn - from acrylonitrile and methanol using triethanolamine and ethylene oxide reaction prod as catalyst

Also Published As

Publication number Publication date
NL281270A (en)
DE1443250A1 (en) 1971-11-25
CH418326A (en) 1966-08-15

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