US2267101A - Method to improve the water-solubility of insoluble or insufficiently soluble organic materials - Google Patents

Method to improve the water-solubility of insoluble or insufficiently soluble organic materials Download PDF

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US2267101A
US2267101A US149094A US14909437A US2267101A US 2267101 A US2267101 A US 2267101A US 149094 A US149094 A US 149094A US 14909437 A US14909437 A US 14909437A US 2267101 A US2267101 A US 2267101A
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fatty acid
soap
water
soaps
parts
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US149094A
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Hueter Richard
Engelbrecht Heinz-Joachim
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UNICHEM CHEMIKALIEN HANDELS A
Unichem Chemikalien Handels A-G
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UNICHEM CHEMIKALIEN HANDELS A
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/24—Halogenated derivatives
    • C07C39/26—Halogenated derivatives monocyclic monohydroxylic containing halogen bound to ring carbon atoms
    • C07C39/27—Halogenated derivatives monocyclic monohydroxylic containing halogen bound to ring carbon atoms all halogen atoms being bound to ring carbon atoms
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/03—Organic sulfoxy compound containing
    • Y10S516/04—Protein or carboxylic compound containing

Definitions

  • the present invention is based on the fact, hitherto unknown, that such variations in the efiiciency of the processes are to a large extent dependent. upon the molecular weight of the fatty acid on which the soap or, respectively, the soap-like acting substances are based.
  • the disinfecting efficiency of a phenol-mixture which by a determined soap-addition in the form of oleinpotash soap is practically annulled, suffers nearly no diminution, if instead of the olein-potash soap one employs the same amount of a soap obtained from low molecular fatty acids (compare Example 1).
  • the soaps obtained from fatty acids with no more than 12 C atoms have proved particularly well adapted for the purposes in question and preferably from fatty acids containing from 6-10 C atoms.
  • this method we are not exclusively confined to the fatty acid salts, but we may also employ suitable condensationproducts of the fatty acids with organic residues containing water-solubilizing groups.
  • the fatty acid esters and fatty acid amides containing in the esteror amidegroup respectively a water-soluble residue and particularly a sulfuric acidor sulfonic acid-residue.
  • fatty acid esters of polyr valent alcohols wherein a hydroxyl-group of the polyvalent alcohol-residue is esterifled with sulfuric acid or substituted by the SO3H-group.
  • the disinfecting power of the preparations diminishes in the same proportion as the chain-length of the alkyl-residue or, respectively, the molecular weight of the fatty acid is increased.
  • the aforesaid condensation-products of the fatty acids show in the same manner the property of converting water-insoluble substances into aqueous solutions.
  • soap-products based on oleic acid which contain no sufficient amount of such means to secure the permanent clearness and furthermore any soap or, respectively, condensation-products of low fatty acids, may be admixed to such an extent, that the combination will not be disintegrated even in any desired dilution. therefore advisable to jointly employ such fatty acid soaps or soap-like fatty acid derivatives which contain higher fatty acid radicals.
  • these components should be present only in such an amount that they would not alone be sufficient to render the total product dilutable with any quantity of water.
  • Example 1 Six and two-tenths parts by weight'of .a phenol-mixture consisting of 1.8 parts of pchlorine-m-cresol, 1.8 parts of chloroxylenol, 1.0 parts of chlorothymol and 1.6 parts of chlorocarvacrol are supplied'in 93.8 parts of an aqueous solution containing such an amount of capryllc acid potash-soap as to give to the total product a proportion of 13.5% of caprylic acid.
  • Example 2 Two and five-tenths parts by wieght of 'p-chlorine-m-cresol, 1.0 parts of chloroxylenol and 2.7 parts of chlorocarvacrol are dissolved together with 30.7 parts of the sodium salt of the sulfuric acid ester of glyceryl ester of caproic acid in parts of spirit and 53.1 parts of distilled water.
  • Example 3 A phenol-mixture consisting of 1.8 parts by weight of p-chlorine-m-cresol, 1.8 parts of chloroxylenol, 1.0 parts of chlorothymol and 1.6 parts of chlorocarvacrol is supplied in 93.8 parts of an aqueous soap-solution, the soap-proportion of which, calculated on fat, is 12% and for the manufacture of which one applied as the fatty acid base the commercial caprylic acid and olein in the ratio of 2:1.
  • the solution, after dilution with water in the ratio of 1:200 is surficiently potent tocause, after one minute, the complete extermination of Staphylococcus and coll-bacteria.
  • An aqueous solution consisting of materials of the group consisting of phenols and fatty acid derivates containing fatty acid radicals of 6 to 10 carbon atoms of the group consisting of soaps, soaplike fatty acid esters containing in the ester group a water solubilizing radical, and soap-like fatty acid amides containing in the amide group a water solubilizing radical.
  • An aqueous solution consisting of materials of the group consisting of phenols and fatty acid derivatives of the group consisting of fatty acid soaps and fatty acid soap-like derivatives containing fatty acid radicals of 6-10 carbon atoms together with fatty acid derivatives of the group consisting of fatty acid soaps and fatty acid soap-like derivatives containing fatty acid radicals with more than 12 carbon atoms wherein the quantity of the higher molecular fatty acid derivative is less than one part out of three parts by weight of the total fatty acid content of said solution.
  • An aqueous solution consisting of materials of the group consisting of phenols, phenol-homologues, substitution products of the phenolhomologues and fatty acid soaps containing fatty acid radicals with 6 to 10 carbon atoms.
  • An aqueous solution comprising materials of the group consisting of phenols, phenol-homologues, substitution products of the phenolhomologues and as a water solubilizing agent fatty acid derivatives of the group consisting of soaps, salts of the sulfuric acid esters of the mono-fatty-acid-esters of polyvalent alcohols, salts of the fatty acid esters containing a sulionic acid group and salts of the fatty acid amides containing a sulfonic acid group, said fatty acid derivatives being composed of compounds having 6 to 10 carbon atoms in the fatty acid radical and compounds having more than 12 carbon atoms in the fatty acid radical, wherein the proportion by Weight of the fatty acid derivatives containing 6 to 10 carbon atoms in the fatty acid radical to the fatty acid derivative containing more than 12 carbon atoms in the fatty acid radical is at last 2 to 1.
  • An aqueous solution consisting of a phenol mixture consisting of p-chloro-m-cresol, chloroxylenol, chlorothymol, chlorocarvacrol and the sodium salt of the caprylic acid.
  • An aqueous solution consisting of a phenol mixture consisting of p-chloro-m-cresol, chloroxylenol, chlorocarvacrol and the sodium salt of the mono-caproyl-glycerine-sulfuric acidester.
  • An aqueous solution consisting of a phenol mixture and a mixture of sodium salts of caprylic acid and of oleic acid wherein the ratio by weight of the sodium salt of caprylic acid and the sodium salt of oleic acid is at least 2 to 1.
  • aqueous solution containing phenols and a dissolving agent wherein the dissolving agent consists of material of the group consisting of soaps of fatty acids having 6 to 12 carbon atoms in the molecule, sulfates and sulfonates of monofatty acid esters of glycerin wherein the fatty acid radical contains 6 to 10 carbon atoms in the molecule.
  • aqueous solution containing phenols and a dissolving agent wherein the dissolving agent consists of material of the group consisting of soaps of fatty acids and sulfates and sulfonates of mono fatty acid esters of glycerin wherein at least two-thirds by weight of the dissolving agent contains fatty acid radicals having 6 to 10 carbon atoms in the molecule.
  • the process of producing stable solutions of phenols in water without impairing the germicontaining at least two parts out of every three cidai or antiseptic properties of the phenols which comprises forming the solution of phenols in water in the presence of a Water solubilizing' agent selected from the group of fatty acid derivatives consisting of soaps, soap-like fatty acid esters containing in the ester group a water solubilizing radical and soap-like fatty acid amides containing in the amide group a water solubiiizing radical said fatty acid derivatives parts by weight of fatty acid derivatives having 6 to 10 carbon atoms in the fatty acid radical.
  • a Water solubilizing' agent selected from the group of fatty acid derivatives consisting of soaps, soap-like fatty acid esters containing in the ester group a water solubilizing radical and soap-like fatty acid amides containing in the amide group a water solubiiizing radical said fatty acid derivatives parts by weight of fatty acid derivatives having 6 to
  • a stable clear aqueous solution of a phenol containing as a dissolving agent a. sodium salt of the isethionic ester of caprylic acid.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

Patented Dec. 23, 1941 METHOD TO IMPROVE THE WATER-SOLU- BILITY OF INSOLUBLE OR INSUFFICIENT- LY SOLUBLE ORGANIC MATERIALS Richard Hueter, Dessau-Rosslau, Anhalt, and Heinz-Joachim Engelbrecht, Dessau, Anhalt, Germany, assignors, by mesne assignments, to Unichem Chemikalien Handels A.-G., Zurich, Switzerland, a corporation of Switzerland No Drawing. Application June 19, 1937, Serial 12 Claims.
It is known that those organic materials which are insoluble or insufficiently soluble in water, such as remedies, disinfecting agents, vermin-combating means etc., e. g. phenols, phenol-homologues and their substitution-products, etheric oils, menthol, camphoi, organic bases such as nicotine, pyridine, quinoline and the like, are rendered soluble in water, if they are combined with soaps. As suitable for the purpose are to be considered inter alia: the soaps obtained from olein, castor oil or from more unsaturated fats, as well as soap-like substances such as Turkey-red oil.
The experiences had with the use of such soapbearing preparations have proved, that the proportion of soap is not at all unrelated to the efficiency of the total preparation. -We must In Germany June 20,1936
. organisms.
know that the soap-addition, in applying com- Y paratively small amounts, causes apparently an enhancement of the efiiciency, whilst higher soap-additions cause, as a rule, a considerable diminution of the degree of efficiency.
The present invention is based on the fact, hitherto unknown, that such variations in the efiiciency of the processes are to a large extent dependent. upon the molecular weight of the fatty acid on which the soap or, respectively, the soap-like acting substances are based. Thus it could indeed be stated, that e. g. the disinfecting efficiency of a phenol-mixture, which by a determined soap-addition in the form of oleinpotash soap is practically annulled, suffers nearly no diminution, if instead of the olein-potash soap one employs the same amount of a soap obtained from low molecular fatty acids (compare Example 1).
The soaps obtained from fatty acids with no more than 12 C atoms have proved particularly well adapted for the purposes in question and preferably from fatty acids containing from 6-10 C atoms. In following this method we are not exclusively confined to the fatty acid salts, but we may also employ suitable condensationproducts of the fatty acids with organic residues containing water-solubilizing groups. Thus we may apply e. g. the fatty acid esters and fatty acid amides containing in the esteror amidegroup respectively a water-soluble residue and particularly a sulfuric acidor sulfonic acid-residue. We may use also fatty acid esters of polyr valent alcohols, wherein a hydroxyl-group of the polyvalent alcohol-residue is esterifled with sulfuric acid or substituted by the SO3H-group. In these cases too the disinfecting power of the preparations diminishes in the same proportion as the chain-length of the alkyl-residue or, respectively, the molecular weight of the fatty acid is increased. The aforesaid condensation-products of the fatty acids show in the same manner the property of converting water-insoluble substances into aqueous solutions.
The described behaviour of the soaps and soap-like derivatives of low molecular fatty acids with no more than 12 C atoms in the molecule makes it possible to apply these products in the manufacture of aqueous solutions serving as pharmaceutical, bacteria-destroying, fungicidal etc. media, and particularly of aqueous disinfecting means or, respectively, of preparations to destroy any noxious or disease-exciting micro- In employing soaps of higher fatty acids it is generally impossible to limit the addition of the soap or of the soap-like product to just the best-proportioned amount with reard to the disinfecting efficiency, as this addition as a rule will not sufiice to secure the transparency with any dilutions or the permanent clearness and stability of those dilutions during a long standing and storage, whereas in employing the low fatty acids the addition may be increased to a large extent without fearing any appreciable reduction of the disinfecting power. Moreover, certain combinations of disinfecting agents with higher molecular soap-products e. g. soap-products based on oleic acid, which contain no sufficient amount of such means to secure the permanent clearness and furthermore any soap or, respectively, condensation-products of low fatty acids, may be admixed to such an extent, that the combination will not be disintegrated even in any desired dilution. therefore advisable to jointly employ such fatty acid soaps or soap-like fatty acid derivatives which contain higher fatty acid radicals. However, these components should be present only in such an amount that they would not alone be sufficient to render the total product dilutable with any quantity of water.
Example 1 Six and two-tenths parts by weight'of .a phenol-mixture consisting of 1.8 parts of pchlorine-m-cresol, 1.8 parts of chloroxylenol, 1.0 parts of chlorothymol and 1.6 parts of chlorocarvacrol are supplied'in 93.8 parts of an aqueous solution containing such an amount of capryllc acid potash-soap as to give to the total product a proportion of 13.5% of caprylic acid.
-.This mother-solution diluted at the ratio of 1:100 and 1:200 with water, caused after a re- ItiS' acting-time of half a minute with both dilutions the perfect extermination of Staphylococcus and coll-bacillus. In replacing in the aforesaid preparation the caprylic acid potash-soap by equal amounts of olein-potash-soap, the same dilutions could with an even 5 minutes reaction not attain the complete extermination. And even after reducing the olein-soap-additlon to 5% of .oleic acid (calculated on the mother-solution) Example 2 Two and five-tenths parts by wieght of 'p-chlorine-m-cresol, 1.0 parts of chloroxylenol and 2.7 parts of chlorocarvacrol are dissolved together with 30.7 parts of the sodium salt of the sulfuric acid ester of glyceryl ester of caproic acid in parts of spirit and 53.1 parts of distilled water.
This mother-solution, after a dilution with water at the proportion of 1:200 causes within half a minute the complete extermination of Staphylococcus and coll-bacteria.
When the aforesaid sulfuric acid ester was replaced by the same amount of mono-palmitoylglycerin sodium combined with sulfuric acid, the complete extermination could under the same conditions not be obtained.
Instead of the mono-caproyl-glycerin sodium combined with sulfuric acid we may likewise apply the caprylic acid ester of the isethionic acid sodium as well as similarly constituted soapproducts.
Example 3 A phenol-mixture consisting of 1.8 parts by weight of p-chlorine-m-cresol, 1.8 parts of chloroxylenol, 1.0 parts of chlorothymol and 1.6 parts of chlorocarvacrol is supplied in 93.8 parts of an aqueous soap-solution, the soap-proportion of which, calculated on fat, is 12% and for the manufacture of which one applied as the fatty acid base the commercial caprylic acid and olein in the ratio of 2:1. The solution, after dilution with water in the ratio of 1:200 is surficiently potent tocause, after one minute, the complete extermination of Staphylococcus and coll-bacteria.
.Under the same conditions, when soap produced only with olein is used there occurs no clestruction. In the same manner as with olein soap, similar results could be obtained with other fatty acid soaps such as ricinoleic alkali etc. in combination with soaps obtained from low fatty acids. 0
We claim:
1. An aqueous solution consisting of materials of the group consisting of phenols and fatty acid derivates containing fatty acid radicals of 6 to 10 carbon atoms of the group consisting of soaps, soaplike fatty acid esters containing in the ester group a water solubilizing radical, and soap-like fatty acid amides containing in the amide group a water solubilizing radical.
2. An aqueous solution consisting of materials of the group consisting of phenols and fatty acid derivatives of the group consisting of fatty acid soaps and fatty acid soap-like derivatives containing fatty acid radicals of 6-10 carbon atoms together with fatty acid derivatives of the group consisting of fatty acid soaps and fatty acid soap-like derivatives containing fatty acid radicals with more than 12 carbon atoms wherein the quantity of the higher molecular fatty acid derivative is less than one part out of three parts by weight of the total fatty acid content of said solution.
3. An aqueous solution consisting of materials of the group consisting of phenols, phenol-homologues, substitution products of the phenolhomologues and fatty acid soaps containing fatty acid radicals with 6 to 10 carbon atoms.
4. An aqueous solution containing materials of the group consisting of phenols, phenol-homologues, substitution products of the phenol-homologues and fatty acid soaps containing fatty acid radicals with 6 to 10 carbon atoms together with fatty acid soaps containing fatty acid radicals with more than 12 carbon atoms'wherein the proportion by weight of the fatty acid soaps containing 6 to 10 carbon atoms in the molecule to the soaps containing more than 12 carbon atoms in the molecule is at least 2 to 1.
5. An aqueous solution comprising materials of the group consisting of phenols, phenol-homologues, substitution products of the phenolhomologues and as a water solubilizing agent fatty acid derivatives of the group consisting of soaps, salts of the sulfuric acid esters of the mono-fatty-acid-esters of polyvalent alcohols, salts of the fatty acid esters containing a sulionic acid group and salts of the fatty acid amides containing a sulfonic acid group, said fatty acid derivatives being composed of compounds having 6 to 10 carbon atoms in the fatty acid radical and compounds having more than 12 carbon atoms in the fatty acid radical, wherein the proportion by Weight of the fatty acid derivatives containing 6 to 10 carbon atoms in the fatty acid radical to the fatty acid derivative containing more than 12 carbon atoms in the fatty acid radical is at last 2 to 1.
6. An aqueous solution consisting of a phenol mixture consisting of p-chloro-m-cresol, chloroxylenol, chlorothymol, chlorocarvacrol and the sodium salt of the caprylic acid.
7. An aqueous solution consisting of a phenol mixture consisting of p-chloro-m-cresol, chloroxylenol, chlorocarvacrol and the sodium salt of the mono-caproyl-glycerine-sulfuric acidester.
8. An aqueous solution consisting of a phenol mixture and a mixture of sodium salts of caprylic acid and of oleic acid wherein the ratio by weight of the sodium salt of caprylic acid and the sodium salt of oleic acid is at least 2 to 1.
9. An aqueous solution containing phenols and a dissolving agent wherein the dissolving agent consists of material of the group consisting of soaps of fatty acids having 6 to 12 carbon atoms in the molecule, sulfates and sulfonates of monofatty acid esters of glycerin wherein the fatty acid radical contains 6 to 10 carbon atoms in the molecule.
10. An aqueous solution containing phenols and a dissolving agent wherein the dissolving agent consists of material of the group consisting of soaps of fatty acids and sulfates and sulfonates of mono fatty acid esters of glycerin wherein at least two-thirds by weight of the dissolving agent contains fatty acid radicals having 6 to 10 carbon atoms in the molecule.
11. The process of producing stable solutions of phenols in water without impairing the germicontaining at least two parts out of every three cidai or antiseptic properties of the phenols which comprises forming the solution of phenols in water in the presence of a Water solubilizing' agent selected from the group of fatty acid derivatives consisting of soaps, soap-like fatty acid esters containing in the ester group a water solubilizing radical and soap-like fatty acid amides containing in the amide group a water solubiiizing radical said fatty acid derivatives parts by weight of fatty acid derivatives having 6 to 10 carbon atoms in the fatty acid radical.
12. A stable clear aqueous solution of a phenol containing as a dissolving agent a. sodium salt of the isethionic ester of caprylic acid.
RICHARD HUETER. HEINZ-JQACHIM ENGELBREC.
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2439440A (en) * 1942-10-07 1948-04-13 North American Cement Corp Method of making disinfectant hydraulic cement
US2439441A (en) * 1943-02-08 1948-04-13 North American Cement Corp Disinfectant hydraulic cement and method of making the same
US2466663A (en) * 1944-10-20 1949-04-05 Ward Baking Co Fungicide containing caprylic acid and its salt
US3046190A (en) * 1956-09-28 1962-07-24 Monsanto Chemicals Germicides
US4098828A (en) * 1973-05-07 1978-07-04 Chrysa Bactericidic and fungicidic chloromethylisopropylphenols

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2439440A (en) * 1942-10-07 1948-04-13 North American Cement Corp Method of making disinfectant hydraulic cement
US2439441A (en) * 1943-02-08 1948-04-13 North American Cement Corp Disinfectant hydraulic cement and method of making the same
US2466663A (en) * 1944-10-20 1949-04-05 Ward Baking Co Fungicide containing caprylic acid and its salt
US3046190A (en) * 1956-09-28 1962-07-24 Monsanto Chemicals Germicides
US4098828A (en) * 1973-05-07 1978-07-04 Chrysa Bactericidic and fungicidic chloromethylisopropylphenols

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