US2209634A - Detergent and emulsifying agent - Google Patents

Detergent and emulsifying agent Download PDF

Info

Publication number
US2209634A
US2209634A US142497A US14249737A US2209634A US 2209634 A US2209634 A US 2209634A US 142497 A US142497 A US 142497A US 14249737 A US14249737 A US 14249737A US 2209634 A US2209634 A US 2209634A
Authority
US
United States
Prior art keywords
boric acid
acid
esters
compound
alcohol
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 - Lifetime
Application number
US142497A
Inventor
Muncie Fred Weaver
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.)
Colgate Palmolive Co
Original Assignee
Colgate Palmolive 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 Colgate Palmolive Co filed Critical Colgate Palmolive Co
Priority to US142497A priority Critical patent/US2209634A/en
Application granted granted Critical
Publication of US2209634A publication Critical patent/US2209634A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • C11D3/166—Organic compounds containing borium
    • 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
    • Y10S516/06—Protein or carboxylic compound containing

Definitions

  • This invention relates to derivatives of polyhydroxy alcohols. It relates more specifically to derivatives of these alcohols in which one or more of the hydroxyls is replaced by an alkyl or acyl group and in which there is present in addition a residue of boric acid. Such compounds, according to this invention are then treated with a solubilizing agent such as a sulfating, sulfonating or phosphating agent, if desired, to produce compounds that have cleansing, preserving, wetting and emulsifying action and are excellent detergents.
  • a solubilizing agent such as a sulfating, sulfonating or phosphating agent
  • poly-hydroxy alcohols examples include ethylene glycol, propylene glycol, glycerine, B-methyl glycerine, erythritol, diglycerol, poly-glycerols, sugar alcohols such as mannitol and sorbitol, sugar acids, reaction prodnets of the poly-hydroxy alcohols with ethylene oxide and other poly-hydroxy compounds.
  • the chlorhydrin or glyclde derivatives of the poly-hydroxy alcohols may be employed.
  • the alkyl group must contain at least eight carbon atoms and be attached to the poly-hydroxy alcohol residue by an ether linkage.
  • ethers are derived by known methods by reaction of the poly-hydroxy alcohol with alcohols straight chain or branched, and primary, secondary or tertiary.
  • alcohols are those derived from fatty or other naturally occurring acids by reduction of the carboxyl group, from oleflns derived from petroleum or other sources, by reduction of ke- *tones and by the oxidation of paraflin.
  • Exam--- pies are lauryl alcohol, alcohols obtained by the reduction of mixed fatty acids of coconut oil or tallow or their esters, oleyl alcohol, di-caproyl alcohol, abietanol, montanol.
  • the acylgroup likewise, must contain at least eight carbon atoms and may be straight chain or branched. Examples are lauric, myristic, oleic or stearic acids, mixed fatty acids from coconut oil, palm oil, palm kernel oil, babasu nut oil, olive oil, tallow, rosin or abietic acid, montanic acid and acids from the oxidation of paraflin:
  • R, R or R.” may represent either the same or different kinds of radicals or residues. It is seen that the compounds formed according to the invention may be quite complex and of high molecular weight, a possibility that may explain the excellent emulsifying action of the compounds.
  • solubilizlng agent it is possible to attach one or more than one solubilizing group to the organic boron compound, and mixed derivatives may be formed in which the boric acid residue links two or more alkyl or acyl poly-hydroxy derivatives, with the sulfate, phosphate or other solubilizlng group occurring in ratio of one or less than one with respect to the poly-hydroxy alcohol residue.
  • the compounds formed may be quite complex, it is not my intention to limit the invention by illustration with formulas, but only to the alkyl or acyl derivatives of a poly-hydroxy compound in which the alkyl or acyl group contains not less than eightcarbon atoms, the derivatives containing a boric acid residue 45 and if desired in addition a solubilizing group such as a sulfuric acid, or phosphoric acid residue.
  • an aromatic compound such as naphthalene or phenol or cresol may be added in which case the ring compound is inserted between the poly-hydroxy borate residue and the sulfuric acid residue, and a substituted aromatic sulfonate is formed.
  • mixed ring compounds obtained by the liquid $02, or other known method of extraction of a fraction of petroleum, particularly from Gulf Coast or California crudes may be employed in place of aromatic compounds of known structure.
  • olefins such as decene, octadecene, isobutylene or its polymers, or other oleflns obtained by separation from or cracking of petroleum or a fraction of petroleum, may be introduced with the ring compounds during sulfonation, these attaching themselves to the ring as alkyl substituents.
  • boric acid derivatives of alkyl or acyl derivatives of poly-hydroxy alcohols are water soluble, as for example the borates of the ethylene oxide derivatives of alkyl ethers or acyl esters of sorbitol. Others form emulsions with water but for solubility in water require the presence in the compound of a solubilizing group such as sulfuric or phosphoric acid residue or an aromatic sulfonic group.
  • All of the sulfated compounds of the general class described above that have been prepared are water soluble and possess marked wetting and detergent properties.
  • the alkali, alkaline earth and heavy metal salts are water soluble.
  • boric acid possesses a preservative action toward bacterial decomposition and compounds of the' type described are quite soluble derivatives of boric acid in a form that in aqueous solution have exceptional penetrating power.
  • the un-sulfated boric acid esters are excellent emulsifying agents.
  • acyl derivatives are easily prepared by heating them with ortho or meta-boric acid in the molal ratio desired under a vacuum to promote removal of water.
  • the acyl derivatives may be formed by reacting the preformed poly-hydroxy borate with a fatty acid, or fatty oil.
  • Boro-sulfates of the alwl or acyl derivatives of poly-hydroxy alcohols may be prepared in several ways:
  • the poly-hydroxy alcohol may be reacted with orthoor metaboric acid under conditions that cause removal of water of reaction and the alcohol borate treated with fatty alcohols or fatty acids or their glycerides or other esters in such a manner as to result in the formation of the cor responding ether or ester of the poly-hydroxy alcohol borate.
  • the compound is then sulfated by suitable reagents, such as sulfuric acid, oleum, chlorsulfonic acid, SO: in liquid 80:.
  • suitable reagents such as sulfuric acid, oleum, chlorsulfonic acid, SO: in liquid 80:.
  • the order of introduction of the fatty acid or alcohol and sulfuric acid may be reversed.
  • the ether or ester derivatives of poly-hydroxy alcohols may be prepared by known methods and converted into boric acid derivatives under conditions that result in the removal of water of reaction, after which the compound may be sulfated by the reagents indicated in 1.
  • a mixture of fatty acid or its glyceride, the poly-hydroxy alcohol, boric acid or its anhydrlde and sulfuric acid or fuming sulfuric acid may be heated to about 50 C. until the reaction product is entirely miscible with water, attention being paid to proportioning the ingredients in the molal relationship desired in the product, and with sulfuric acid of suflicient strength and quantity to form the sulfate and absorb the water of reaction.
  • Sulfuric acid in'this case acts to hydrolyze the tri-glyceride if used, to esterify the poly-hydroxy alcohol with fatty acid present or formed by hydrolysis, to bring about ester formation with the boric acid, to sulfate the compound and to absorb the water of reaction.
  • the boro-sulfate of fatty acid monc-glyceride is soluble in water and has marked wetting, emulsifying and detergent properties in aqueous solution.
  • the salts exhibit the same properties.
  • the boro-sulfate of the fatty ether of glycerine is water soluble and as such or in form of its alkali, alkaline earth, ammonium and organic amine salts exhibits marked emulsifyin wetting and detergent characteristics.
  • CHIOH C1110 O C R Neutralization may be carried out to form the mixed salt of the organic compound and the excess sulfuric'acid.
  • a process for preparing boric acid esters of fatty acid monoglycerides which comprises heating at least one fatty acid monoglyceride and boric acid under conditions to remove the water of reaction.
  • the process which comprises preparing a boric acid ester of a polyhydroxy alcohol, condensing said ester with at least one compound of the class consisting of fatty alcohols, fatty acids, and esters thereof, to form a boric acid ester of a compound of the class consisting of partial ethers and esters of polyhydroxy alcohols, sulphating the condensation product and neutralizing the resulting material.
  • the process which comprises warming a mixture containing in molecular proportions about one part of coconut oil, about two parts of substantially anhydrous glycerine, from about one to three parts of boric acid, and more than three parts of sulphuric acid at from 30 to C. until the product is miscible with water, and neutralizing the reaction product.
  • a wetting agent and detergent which comprises reacting at least one compound of the class consisting of partial ethers and esters of polyhydroxy alcohols, with boric acid, an aromatic compound, and fuming sulphuric acid.
  • a wetting agent and detergent which comprises reacting an olefin and at least one compound of the class consisting of partial ethers and esters of polyhydroxy alcohols, with boric acid, an aromatic compound, and fuming sulphuric acid.
  • a wetting agent and detergent which comprises reacting boric acid and at least one compound of the class consisting of partial ethers and esters of polyhydroxy alcohols, with a liquid sulphur dioxide extract of a fraction of petroleum, and fuming sulphuric acid.
  • a compound of the class consisting of boric acid esters, boric acid-sulphuric acid esters, boric acid-phosphoric acid esters, and salts of said esters, of coconut oil fatty acid monoglycerides.
  • reaction product obtained by warming a mixture of tallow, glycerine, boric acid and sulphuric acid which contains a sufllcient amount of sulphur trioxide to absorb the water of reaction.
  • a cleansing agent comprising as its essential ingredient a compound of the class consisting of boric acid esters, boric acid-sulphuric acid esters, boric acid-phosphoric acid esters, and salts of said esters of at least one aliphatic acid monoglyceride.
  • the product prepared by reacting boric acid, an olefin, and at least one compound of the class consisting of partial ethers and esters of polyhydroxy alcohols, with an aromatic compound, and fuming sulphuric acid.
  • An emulsifying agent comprising as the essential ingredient a boric acid ester of a fatty acid monoglyceride.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)

Description

Patented July 30, 1940 DETERGENT AND EMULSIFYING AGENT Fred Weaver Muncie, New Brunswick, N. 1., as-
signor to Colgate-Palmolive-Peet Company, Jersey City, N. J., a corporation of Delaware No Drawing.
Application May 13, 1937,
Serial No. 142,497
27 Claims.
This invention relates to derivatives of polyhydroxy alcohols. It relates more specifically to derivatives of these alcohols in which one or more of the hydroxyls is replaced by an alkyl or acyl group and in which there is present in addition a residue of boric acid. Such compounds, according to this invention are then treated with a solubilizing agent such as a sulfating, sulfonating or phosphating agent, if desired, to produce compounds that have cleansing, preserving, wetting and emulsifying action and are excellent detergents.
Examples of the poly-hydroxy alcohols that may be employed are ethylene glycol, propylene glycol, glycerine, B-methyl glycerine, erythritol, diglycerol, poly-glycerols, sugar alcohols such as mannitol and sorbitol, sugar acids, reaction prodnets of the poly-hydroxy alcohols with ethylene oxide and other poly-hydroxy compounds. In certain methods of preparation, the chlorhydrin or glyclde derivatives of the poly-hydroxy alcohols may be employed.
The alkyl group must contain at least eight carbon atoms and be attached to the poly-hydroxy alcohol residue by an ether linkage. Such ethers are derived by known methods by reaction of the poly-hydroxy alcohol with alcohols straight chain or branched, and primary, secondary or tertiary. Such alcohols are those derived from fatty or other naturally occurring acids by reduction of the carboxyl group, from oleflns derived from petroleum or other sources, by reduction of ke- *tones and by the oxidation of paraflin. Exam-- pies are lauryl alcohol, alcohols obtained by the reduction of mixed fatty acids of coconut oil or tallow or their esters, oleyl alcohol, di-caproyl alcohol, abietanol, montanol.
The acylgroup, likewise, must contain at least eight carbon atoms and may be straight chain or branched. Examples are lauric, myristic, oleic or stearic acids, mixed fatty acids from coconut oil, palm oil, palm kernel oil, babasu nut oil, olive oil, tallow, rosin or abietic acid, montanic acid and acids from the oxidation of paraflin:
It is not known definitely in how many ways the boric acid may be combined with ethers or esters of these polyhydroxy compounds. It appears, for instance. that ortho-boric acid may not only be combined with a compound containing one hydroxyl to yield a derivative of the type:
with two hydroxyls to give a compound of the type:
o R/ mon but also that two or three linkages of the boric acid residue may be attached to hydroxyls of separate and distinct organic residues giving a compound of the type:
where R, R or R." may represent either the same or different kinds of radicals or residues. It is seen that the compounds formed according to the invention may be quite complex and of high molecular weight, a possibility that may explain the excellent emulsifying action of the compounds.
Similarly, by variation in operating conditions and choice of solubilizlng agent, it is possible to attach one or more than one solubilizing group to the organic boron compound, and mixed derivatives may be formed in which the boric acid residue links two or more alkyl or acyl poly-hydroxy derivatives, with the sulfate, phosphate or other solubilizlng group occurring in ratio of one or less than one with respect to the poly-hydroxy alcohol residue. Since the compounds formed may be quite complex, it is not my intention to limit the invention by illustration with formulas, but only to the alkyl or acyl derivatives of a poly-hydroxy compound in which the alkyl or acyl group contains not less than eightcarbon atoms, the derivatives containing a boric acid residue 45 and if desired in addition a solubilizing group such as a sulfuric acid, or phosphoric acid residue.
In the treatment with a sulfonating agent, an aromatic compound such as naphthalene or phenol or cresol may be added in which case the ring compound is inserted between the poly-hydroxy borate residue and the sulfuric acid residue, and a substituted aromatic sulfonate is formed. Or mixed ring compounds obtained by the liquid $02, or other known method of extraction of a fraction of petroleum, particularly from Gulf Coast or California crudes may be employed in place of aromatic compounds of known structure. Also, olefins, such as decene, octadecene, isobutylene or its polymers, or other oleflns obtained by separation from or cracking of petroleum or a fraction of petroleum, may be introduced with the ring compounds during sulfonation, these attaching themselves to the ring as alkyl substituents.
Certain of the boric acid derivatives of alkyl or acyl derivatives of poly-hydroxy alcohols are water soluble, as for example the borates of the ethylene oxide derivatives of alkyl ethers or acyl esters of sorbitol. Others form emulsions with water but for solubility in water require the presence in the compound of a solubilizing group such as sulfuric or phosphoric acid residue or an aromatic sulfonic group.
All of the sulfated compounds of the general class described above that have been prepared are water soluble and possess marked wetting and detergent properties. The alkali, alkaline earth and heavy metal salts are water soluble. By variation in the choice of poly-hydroxy alcohol and the proportion of boric acid and conditions of its reaction, it is possible to vary the emulsifying characteristics of the product formed. Furthermore, boric acid possesses a preservative action toward bacterial decomposition and compounds of the' type described are quite soluble derivatives of boric acid in a form that in aqueous solution have exceptional penetrating power.
The un-sulfated boric acid esters are excellent emulsifying agents.
Borates of the poly-hydroxy alkyl or acyl derivatives are easily prepared by heating them with ortho or meta-boric acid in the molal ratio desired under a vacuum to promote removal of water. In addition, the acyl derivatives may be formed by reacting the preformed poly-hydroxy borate with a fatty acid, or fatty oil.
Boro-sulfates of the alwl or acyl derivatives of poly-hydroxy alcohols may be prepared in several ways:
1. The poly-hydroxy alcohol may be reacted with orthoor metaboric acid under conditions that cause removal of water of reaction and the alcohol borate treated with fatty alcohols or fatty acids or their glycerides or other esters in such a manner as to result in the formation of the cor responding ether or ester of the poly-hydroxy alcohol borate. The compound is then sulfated by suitable reagents, such as sulfuric acid, oleum, chlorsulfonic acid, SO: in liquid 80:. The order of introduction of the fatty acid or alcohol and sulfuric acid may be reversed.
2. The ether or ester derivatives of poly-hydroxy alcohols may be prepared by known methods and converted into boric acid derivatives under conditions that result in the removal of water of reaction, after which the compound may be sulfated by the reagents indicated in 1.
3. A mixture of fatty acid or its glyceride, the poly-hydroxy alcohol, boric acid or its anhydrlde and sulfuric acid or fuming sulfuric acid may be heated to about 50 C. until the reaction product is entirely miscible with water, attention being paid to proportioning the ingredients in the molal relationship desired in the product, and with sulfuric acid of suflicient strength and quantity to form the sulfate and absorb the water of reaction. Sulfuric acid in'this case acts to hydrolyze the tri-glyceride if used, to esterify the poly-hydroxy alcohol with fatty acid present or formed by hydrolysis, to bring about ester formation with the boric acid, to sulfate the compound and to absorb the water of reaction.
Illustrative equations are given below. The equations are not intended, however, to limit the scope of the invention. More particularly, is it not intended to limit the invention to compounds of the simple structure indicated. As discussed above, it is probable that more complex compounds are formed by the attachment of more than one organic residue to a single boric acid residue, and specific claim is made to such com- P unds.
ROCHr-CH-CHCHCHCH| i. i. i. t. t. t J; e H: H: Ha Ha H:
a Ha Ha Ha H:
B6B) n 11 n The borate of the Dentahydroxyl ethyl ether of sorbitol fatty alcohol ether is soluble in water and exhibits marked emulsifying, wetting and detergent properties.
R-OCH,CHg-O-CHg-CHrBOg-i-Hfl) The meta-boric acid ester of the fatty ether of di-ethylene glycol is an excellent emulsifying agent.
The boro-sulfate of fatty acid monc-glyceride is soluble in water and has marked wetting, emulsifying and detergent properties in aqueous solution. The salts exhibit the same properties.
The boro-sulfate of the fatty ether of glycerine is water soluble and as such or in form of its alkali, alkaline earth, ammonium and organic amine salts exhibits marked emulsifyin wetting and detergent characteristics.
CHIOH C1110 O C R Neutralization may be carried out to form the mixed salt of the organic compound and the excess sulfuric'acid.
It is specifically within the scope of this invention to produce and employ as cleansing, preserving, wetting, deterging and emulsifying agents, the bore-sulfuric acid derivatives as such or their compounds with alkalies or alkaline earths, ammonia, an ethanolamine, or other basic substance, whether organic or inorganic.
EXAMPLES or PREPARATION 1.Coconut oil fatty acid monoglyceride borate 94.7 gms. of coconut oil fatty acid monoglyceride and 6.9 gms. of ortho-boric acid were mixed in a distilling flask and warmed. Above 100 C. water was evolved and at 125 0., solution of the The flask was placed under vacuum to assist in withdrawal of water and the product heated to 150 C. under 1" pressure. The loss in weight amounted to 6.5 gms. whereas theory. would require'6.0 gms. The product was a clear straw colored liquid slowly solidifying at about 28 C. No boric acid separated on standing.
2.Sulfation of coconut oil monoglyceride borate 43.0 gms. of coconut oil monoglyceride borate prepared as above was warmed to 47 C. and 69.8 gms. of sulfuric acid (102.8%) was added dropwise. Within a short time after the acid had been added, a sample of the product was completely soluble in water. The mixture of the organic boro-sulfuric acid with the excess sulfuric acid was stirred into ice water and neutralized with caustic soda. The product formed a perfectly clear 1% solution in water, whether soft or hard, and exhibited excellent foaming, wetting and washing properties.
3.Coconut oil fatty acid monoglycefide borosulfate 43.2 gms. of coconut 01], 12.8 gms. of 99.3% glycerine, and 4.0 gms. of ortho-boric acid were taken with 105.2 gms. of sulfuric acid. The sulfuric acid was of 102.84% strength, containing 11.9% of free $03. The boric acid was added to the sulfuric acid and the mixture placed in an ice bath, after which with stirring, the glycerine was added dropwise. The mixture was warmed to 45-50 C. and at this temperature with stirring, the oil was added slowly. After holding the batch at this. temperature for minutes, a test sample was perfectly clear on dilution with water. The batch was now dumped into a mixture of ice and water and neutralized with 30% caustic soda.
4.Fatty acid hydrozyethyl sorbitol bm'ate sorbitol were converted into the ortho-boric acid ester by heating in vacuo with 10.3 grams of ortho-boric acid until the water of reaction was removed.
5.-Boro-sulphate of launll glycerine ether 138 grams of the ether of glycerine and lauryl alcohol were heated in vacuo with 28 grams of meta-boric acid at a temperature up to 150 C. until the reaction was completed by removal of the water liberated. The product was then treated with 275 grams of 20% oleum H2804) at a temperature of 30 to C. for one hour. The reaction mixture was then poured into ice and water and neutralized with monoethanolamine to a pH of 7.0.
6.-Boro-sulphonate of cocoanut oil monoglyceride and Edeleanu extract of petroleum 284 grams of the monoglyceride of cocoanut oil fatty acids were converted into the orthobnric acid ester as described in Example 1. This was mixed with 100 grams of Edeleanu extract of California lubricating oil and the whole treated with 500 grams of 20% oleum at 8 C. for about 2 hours. The reaction mixture was then poured into ice and water and neutralized with ammonium hydroxide.
7.Boro-sulphonate of cocoanut oil monoglyceride, olefin and naphthalene 284 grams of cocoanut oil fatty acid monoglyceride were converted into the meta-boric acid ester by heating in vacuo with 28 grams of metaboric acid. The product was mixed with 125 grams of naphthalene and 100 grams of decene and heated at 75 C. with 500 grams of 20% oleum for 2 hours. The reaction mixture was then extracted with butyl alcohol and the alcoholic-solution neutralized with an aqueous solution of sodium bicarbonate, after which the alcohol solution was removed by distillation.
Having described my invention, 1 claim:
1. A process for preparing boric acid esters of fatty acid monoglycerides which comprises heating at least one fatty acid monoglyceride and boric acid under conditions to remove the water of reaction.
2. The process which comprises preparing a boric acid ester of a polyhydroxy alcohol, condensing said ester with at least one compound of the class consisting of fatty alcohols, fatty acids, and esters thereof, to form a boric acid ester of a compound of the class consisting of partial ethers and esters of polyhydroxy alcohols, sulphating the condensation product and neutralizing the resulting material.
3. The process which comprises preparing a boric acid ester of a polyhydroxy alcohol, treating said ester with a sulphating agent, condensing the product with at least one compound of the class consisting of fatty alcohols, fatty acids and esters thereof, to form an inorganic acid ester of a compound of the class consisting oi partial ethers and esters of polyhydroxy alcohols, and neutralizing the resulting inorganic acid ester.
4. The process which comprises reacting at least one compound of the class consisting of partial ethers and esters of polyhydroxy alcohols, with boric acid to form the corresponding boric acid ester, sulphating said boric acid ester and neutralizing the resulting product.
5. The process which comprises reacting a mixture of a polyhydroxy alcohol, boric acid, sulphuric acid, and a compound of the class consisting of fatty acids and esters thereof by warming until the reaction product is miscible with water, and neutralizing the resulting product.
6. The process which comprises warming a mixture containing in molecular proportions about one part of coconut oil, about two parts of substantially anhydrous glycerine, from about one to three parts of boric acid, and more than three parts of sulphuric acid at from 30 to C. until the product is miscible with water, and neutralizing the reaction product.
7. The process of producing a wetting agent and detergent which comprises reacting at least one compound of the class consisting of partial ethers and esters of polyhydroxy alcohols, with boric acid, an aromatic compound, and fuming sulphuric acid.
8. The process of producing a wetting agent and detergent which comprises reacting an olefin and at least one compound of the class consisting of partial ethers and esters of polyhydroxy alcohols, with boric acid, an aromatic compound, and fuming sulphuric acid.
9. The process of producing a wetting agent and detergent which comprises reacting boric acid and at least one compound of the class consisting of partial ethers and esters of polyhydroxy alcohols, with a liquid sulphur dioxide extract of a fraction of petroleum, and fuming sulphuric acid.
10. The process which comprises reacting a partial ether of a polyhydroxy alcohol and a high molecular weight aliphatic alcohol, with boric acid under conditions to remove the water of reaction.
11. The process which comprises reacting a partial ester of a polyhydroxy alcohol and a high molecular weight fatty acid, with boric acid under conditions to remove the water of reaction.
12. The process which comprises reacting a mixed ether of a polyhydroxy alcohol and a high molecular weight aliphatic alcohol, with boric acid, and with a sulphonating agent.
13. The process which comprises reacting a partial ester of a polyhydroxy alcohol and a high molecular weight fatty acid, with boric acid, and with a sulphonating agent.
14. The process which comprises reacting a polyhydroxy alcohol with a high molecular weight fatty acid, and with boric acid under conditions to remove the water of reaction.
15. The process which comprises reacting at least one high molecular weight aliphatic compound selected from the group consisting of partial ethers and esters of polyhydroxy alcohols,
" with boric acid, and with a sulphonating agent.
16. A compound of the class consisting of boric acid esters, boric acid-sulphuric acid esters, boric acid-phosphoric acid esters, and salts of said esters, of at least one compound of the class consisting of aliphatic partial ethers and esters of polyhydroxy alcohols, wherein the aliphatic substituent on the polyhydroxy alcohol contains at least eight carbon atoms.
17. A compound of the class consisting of boric acid esters, boric acid-sulphuric acid esters, boric acid-phosphoric acid esters, and salts of said esters, of coconut oil fatty acid monoglycerides.
18. The reaction product obtained by warming a mixture of tallow, glycerine, boric acid and sulphuric acid which contains a sufllcient amount of sulphur trioxide to absorb the water of reaction.
19. A cleansing agent comprising as its essential ingredient a compound of the class consisting of boric acid esters, boric acid-sulphuric acid esters, boric acid-phosphoric acid esters, and salts of said esters of at least one aliphatic acid monoglyceride.
20. The product obtained by reacting at least one compound of the class consisting of partial ethers and esters of polyhydroxy alcohols with boric acid, an aromatic-compound and fuming sulphuric acid.
21. The product prepared by reacting boric acid, an olefin, and at least one compound of the class consisting of partial ethers and esters of polyhydroxy alcohols, with an aromatic compound, and fuming sulphuric acid.
22. The product prepared by reacting boric acid and at least one compound ,of the class consisting of partial ethers and esters of polyhydroxy alcohols with a liquid sulphur dioxide extract of a fraction of petroleum and fuming sulphuric acid.
23. A boric acid ester of a compound of the class consisting of partial ethers and sters of polyhydroxy alcohols, the organic substituent on the polyhydroxy alcohol having at least eight carbon atoms.
24. A boric acid ester of a compound of the.
class consisting of partial ethers and esters of polyhydroxy alcohols, the organic substituent on the polyhydroxy alcohol having at least eight carbon atoms, and the polyhydroxy alcohol being glycerine.
25. Boric acid esters of monoglycerides of coconut oil fatty acids.
26. A compound of the class consisting of boric acid esters, boric acid-sulphuric acid esters, boric acid-phosphoric acid esters and salts of said esters, of a partial aliphatic ether of polyhydroxy alcohols wherein the aliphatic substituent on the polyhydroxy alcohol contains at least eight carbon atoms.
27. An emulsifying agent comprising as the essential ingredient a boric acid ester of a fatty acid monoglyceride.
FRED WEAVER MUNCIE.
US142497A 1937-05-13 1937-05-13 Detergent and emulsifying agent Expired - Lifetime US2209634A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US142497A US2209634A (en) 1937-05-13 1937-05-13 Detergent and emulsifying agent

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US142497A US2209634A (en) 1937-05-13 1937-05-13 Detergent and emulsifying agent

Publications (1)

Publication Number Publication Date
US2209634A true US2209634A (en) 1940-07-30

Family

ID=22500068

Family Applications (1)

Application Number Title Priority Date Filing Date
US142497A Expired - Lifetime US2209634A (en) 1937-05-13 1937-05-13 Detergent and emulsifying agent

Country Status (1)

Country Link
US (1) US2209634A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2839564A (en) * 1952-02-21 1958-06-17 Shell Dev Cyclic esters of boric acid
US2857370A (en) * 1954-11-22 1958-10-21 Gen Aniline & Film Corp Process of preparing ester and amide type anionic surface active agents
US4168275A (en) * 1977-09-29 1979-09-18 James G. McDonald Process for modifying linseed oil

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2839564A (en) * 1952-02-21 1958-06-17 Shell Dev Cyclic esters of boric acid
US2857370A (en) * 1954-11-22 1958-10-21 Gen Aniline & Film Corp Process of preparing ester and amide type anionic surface active agents
US4168275A (en) * 1977-09-29 1979-09-18 James G. McDonald Process for modifying linseed oil

Similar Documents

Publication Publication Date Title
US2081876A (en) Diaryl oxide sulphonic acids and processes for preparing the same
US2271635A (en) Dry cleaning composition and method
JPS59206495A (en) Mixed surfactant composition
US2209634A (en) Detergent and emulsifying agent
US2978416A (en) Concentrated aqueous detergent composition
GB523549A (en) A process for increasing the wetting-out power of mercerising lyes
US1913794A (en) Process of preparing ethionic acid or carbyl sulphate
US2192721A (en) Preparation of sulphuric acid derivatives of fatty acid diesters of glycols
US2771484A (en) Sulfonation of organic hydroxy compounds
US2529538A (en) Sulfonation of olefins
US1916776A (en) Sulphonated fatty acid esters and their production
US2335193A (en) Sulphonic acid and process for producing it
US2223363A (en) Alkyl-hydroxy-diphenyl sulphonates and method of producing them
US2341060A (en) Sulphonated organic compound
US2160343A (en) Sulphuric acid derivatives of polyisobutylene
US2127495A (en) Manufacture of nitrogen base salts of acid alkyl esters
US2941951A (en) Foaming detergent compositions
US2136379A (en) Sulphuric acid derivatives of fatty acid diesters of glycols
US2099214A (en) Process fob forming the sulphuric
US2186132A (en) Sulphonated terpenyl alkyl phenols
US2135358A (en) Process for sulphonating and sulphating olefines
US2111820A (en) Alkyl aromatic acetic acid and homologues thereof
US2213588A (en) Detergent aid
US2127103A (en) Reaction products of a primary al
US2293265A (en) Surface active agent