US2173638A - Process for manufacturing textile agents - Google Patents

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US2173638A
US2173638A US136513A US13651337A US2173638A US 2173638 A US2173638 A US 2173638A US 136513 A US136513 A US 136513A US 13651337 A US13651337 A US 13651337A US 2173638 A US2173638 A US 2173638A
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acid
alcohol
phosphorus
high molecular
molecular weight
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US136513A
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Rozenbroek Meindert Danius
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/10—Phosphatides, e.g. lecithin
    • C07F9/103—Extraction or purification by physical or chemical treatment of natural phosphatides; Preparation of compositions containing phosphatides of unknown structure
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
    • C07F5/02—Boron compounds
    • C07F5/04—Esters of boric acids
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/34—Derivatives of acids of phosphorus
    • C11D1/347—Other P-containing anionic compounds
    • 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
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/02—Water
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
    • 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
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • 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
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/061—Esters derived from boron
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/46—Textile oils
    • 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

Definitions

  • the invention has for its object a process for manufacturing textile agents, such as cleansing,
  • the invention also relates to textile agents con sisting of or containing the compounds specified above.
  • ethers or esters sulfonated according to the invention are represented by the following for- 26 mulae (1:) R000 omen, o P on (b) R o omen, o P (on),
  • the-acid used is phosphorous acid; however, similar compounds can be derived from other acids containing phosphorus, especially phosphoric acid.
  • the monohydric alcohol used may be saturated or unsaturated, elaidinised or not, and primary,
  • the alcohol may contain other substituents, e. g. halogen atoms, acyl or other groups. They may be manufactured 5o artificially or they may be obtained from natural products, e. g. waxes. Cholesterol, isocholesterol and similar alcohols of a more complicated nature which can be obtained from waxes are also suitable for the purpose.
  • the higher fatty acids may also be saturated (or. ace-rec) orunsaturated and elaidinised or not. They may cgntain one or more hydroxy groups or other substituents, e. g. halogen atoms, acyl or other groups. 4
  • polyhydric alcohols besides the glycol and 5 lycerol mentioned in the above formulae, erythritol,.propene diol, 2.3 butanediol, the alcohols obtained by reduction of sugars etc., may be used.
  • polyhydric alcohols one can also use partial ethers of the polyhydric alcohols 10 which contain at least two free hydroxy groups, e. g. the polyglycol or polyglycerol ether, Aminoethers with at least two free hydroxy groups, e. g. triethanol amine, are also suitable.
  • ethers or esters are then sulphonated according to methods known per se.
  • the sulphonation can be carried out with sulphuric acid or other sulphonating agents, e. g. oleum, sulphuric acid anhydride or chlorsulphonic acid, alone or together with water binding agents, e. g. phosphorus pentoxide.
  • the sulphonating agent can be added to the material to be sulphonated or vice versa.
  • the compounds obtained according to the in- Vention are distinguished from the substances obtained according to prior processes by the presence of a monoesterified phosphoric acid or phosphorous acid group, i. e. a group resulting if a polybasic acid of this character is esterified with one hydroxy group of an alcohol.
  • a monoesterified phosphoric acid or phosphorous acid group i. e. a group resulting if a polybasic acid of this character is esterified with one hydroxy group of an alcohol.
  • This monoesterified acid group has a favourable infiuence on the properties of the com-' pounds obtained. Sc e. g. the clearness of a dilute solution in hard water after standing is better. The solutions in soft water are even absolutely 85 clear.
  • Suitable starting materials are mixtures of fatty acids and fat alcohols as e. g. obtained by the saponification oi waxes and by the incomplete reduction of fatty acids to alcohols.
  • fatty acid may e. g. be esterified and the alcohol etherified both with glycol, and in the mixture obtained the ester and the ether may be converted into the corresponding monoesterifled phosphorus compounds and finally the mixture may be sulphonated.
  • the sulphonated compounds obtained according to the invention can be converted into substances containing active oxygen by treating the non-neutralised sulphonation product with a peroxide and neutralising the reaction product, or
  • Example I 20 parts by weight of the monostearyl ether of glycol in molten condition are poured into 11 parts by weight of PC13 and slowly heated for some time until the development of gas is substantially finished. After-cooling, 20 parts by weight of sulphuric acid are slowly added to the reaction mixture, the mass being well stirred and temperature.
  • the sulphonate is then freed from the excess of acid by washing with a mixture of water and Glaubers salt and neutralised.
  • Example II 225 parts by weight of the monolaurylether of glycol are esterified with 150.parts by weight of P205 and then sulphonated with $250 parts by weight of sulphuric acid at a moderately elevated
  • the neutralised product is a very aivaeas organic acid derived from phosphorus and sulfonating the resultant inorganic acid ester.
  • Sulfonated esters made from a compound selected from the group consisting of (a) ethers made from a polyhydric alcohol and a high molecular weight aliphatic alcohol and (b) esters made from a polyhydric alcohol and a high molecular weight fatty acid, and an inorganic acid derived from phosphorus.
  • Sulfonated esters made from an ether of a polyhydric alcohol and a high molecular weight aliphatic alcohol, and an inorganic acid derived from phosphorus.

Description

Patented Sept, 39, 1939 i raccass non mmrrncrnnnee r aenn'r Meindert Danica Rozenbroeh, Delden, T wenthe, Over-Heel, Netherlands No Drawing. Application April 12, 1937, Seriai No. 136,513. In the Netherlands February 2'3,
7 @iaims.
It has been proposed in British specification No. 409,598 and Dutch specification No. 36,289 to convert higher alcohols into the corresponding esters of acids derived from phosphorus and to sulphonate the said esters whereby products are obtained which contain sulphur as well as phosphorus in organically bound form.
The invention has for its object a process for manufacturing textile agents, such as cleansing,
10 wetting out,.foaming, dispersing, equalizing and bleaching agents which comprises sulphonating' a compound derived from a polyhydric alcohol by esterifying at least one hydroxy group of the Same with an acid derived from phosphorus so as to produce a primary ester of the said acid,
and esteriiying or etherifying at least one remaining hydroxy group of the alcohol with a fatty acid or a mcnohydric alcohol having at least 6 carbon atoms.
The invention also relates to textile agents con sisting of or containing the compounds specified above.
The ethers or esters sulfonated according to the invention are represented by the following for- 26 mulae (1:) R000 omen, o P on (b) R o omen, o P (on),
e a coo cnlonon on, o r (on):
' (d) a 0 on; error: on, o I" on It being the alkyl group with at least 6 carbon atoms present in the fatty acid or the monohydric alcohol from which the esters or etherswith the polyhydric alcohol are derived.
In the formulae given above the-acid used is phosphorous acid; however, similar compounds can be derived from other acids containing phosphorus, especially phosphoric acid.
The monohydric alcohol used may be saturated or unsaturated, elaidinised or not, and primary,
secondary or tertiary. If desired the alcohol may contain other substituents, e. g. halogen atoms, acyl or other groups. They may be manufactured 5o artificially or they may be obtained from natural products, e. g. waxes. Cholesterol, isocholesterol and similar alcohols of a more complicated nature which can be obtained from waxes are also suitable for the purpose.
55 The higher fatty acids may also be saturated (or. ace-rec) orunsaturated and elaidinised or not. They may cgntain one or more hydroxy groups or other substituents, e. g. halogen atoms, acyl or other groups. 4
As polyhydric alcohols besides the glycol and 5 lycerol mentioned in the above formulae, erythritol,.propene diol, 2.3 butanediol, the alcohols obtained by reduction of sugars etc., may be used.' Instead of the polyhydric alcohols one can also use partial ethers of the polyhydric alcohols 10 which contain at least two free hydroxy groups, e. g. the polyglycol or polyglycerol ether, Aminoethers with at least two free hydroxy groups, e. g. triethanol amine, are also suitable.
The above described phosphorus containing it! ethers or esters are then sulphonated according to methods known per se. The sulphonation can be carried out with sulphuric acid or other sulphonating agents, e. g. oleum, sulphuric acid anhydride or chlorsulphonic acid, alone or together with water binding agents, e. g. phosphorus pentoxide. The sulphonating agent can be added to the material to be sulphonated or vice versa.
The compounds obtained according to the in- Vention are distinguished from the substances obtained according to prior processes by the presence of a monoesterified phosphoric acid or phosphorous acid group, i. e. a group resulting if a polybasic acid of this character is esterified with one hydroxy group of an alcohol. The presence of this monoesterified acid group has a favourable infiuence on the properties of the com-' pounds obtained. Sc e. g. the clearness of a dilute solution in hard water after standing is better. The solutions in soft water are even absolutely 85 clear.
Not only the solubility but also the resistance against moderately concentrated alkaline solutions, e. g. a sodium hydroxide solution of 15%, even at the boiling point,.is improved.
' Suitable starting materials are mixtures of fatty acids and fat alcohols as e. g. obtained by the saponification oi waxes and by the incomplete reduction of fatty acids to alcohols. The
fatty acid may e. g. be esterified and the alcohol etherified both with glycol, and in the mixture obtained the ester and the ether may be converted into the corresponding monoesterifled phosphorus compounds and finally the mixture may be sulphonated.
The sulphonated compounds obtained according to the invention can be converted into substances containing active oxygen by treating the non-neutralised sulphonation product with a peroxide and neutralising the reaction product, or
by reacting the neutrallsed product with a peroxide. The product thereby acquires bleaching properties.
. 'The invention will. be illustrated by the following examples:
Example I 20 parts by weight of the monostearyl ether of glycol in molten condition are poured into 11 parts by weight of PC13 and slowly heated for some time until the development of gas is substantially finished. After-cooling, 20 parts by weight of sulphuric acid are slowly added to the reaction mixture, the mass being well stirred and temperature.
good wetting out agent.
care being taken that the temperature generally does not exceed 35 C. The sulphonate is then freed from the excess of acid by washing with a mixture of water and Glaubers salt and neutralised.
Example II 225 parts by weight of the monolaurylether of glycol are esterified with 150.parts by weight of P205 and then sulphonated with $250 parts by weight of sulphuric acid at a moderately elevated The neutralised product is a very aivaeas organic acid derived from phosphorus and sulfonating the resultant inorganic acid ester.
3. The process which comprises reacting an ester made from a polyhyd'ric alcohol and a high molecular weight fatty acid, with an inorganic acid derived from phosphorus, and suii'onating the resultant inorganic acid ester.
4. The process which comprises reacting a mixture of (a) an ether made from a polyhydric alcohol and a high molecular weight aliphatic alcohol and (b) an ester made from a polyhydric alcohol and a high molecular weight fatty acid with an inorganic acid derived from phosphorus and sulfonating the resultant inorganic acid ester mixture, the-said mixture of an ether made from a polyhydric alcohol and a high molecular weight aliphatic alcohol and an ester made from a polyhydric alcohol and a high molecular weight fatty acid being obtained from a pre-existing mixture of a high molecular weight aliphatic alcohol and a high molecular weight fatty acid by etherifying the said aliphatic alcohol and esterifying the said fatty acid in the mixture with a polyhydric alcohol.
5. Sulfonated esters made from a compound selected from the group consisting of (a) ethers made from a polyhydric alcohol and a high molecular weight aliphatic alcohol and (b) esters made from a polyhydric alcohol and a high molecular weight fatty acid, and an inorganic acid derived from phosphorus.
6. Sulfonated esters made from an ether of a polyhydric alcohol and a high molecular weight aliphatic alcohol, and an inorganic acid derived from phosphorus.
7. Sulfonated esters made from an ester of a 'polyhydric alcohol and a high molecular weight I CERTIFICATE QF-CORRECTION. Patentillo. 2,175,658. September 19,1959.
'MEINDERT DANIUS ROZENBROEK.
It is hereby certified that the above numbered patent was erroneously issued to the inventor, said "Rozenbroek" as owner of the entire interest therein, whereas said patent should have been issued to Meindert Danius Rozenbroek, of Delden, Twenthe, Overijsel, Netherlands, assignor, by direct and mesne assignments, .to himself and N. V.- Chemische Fabriekfie'rvo, a
Limited Liability Company, of Delden, Twente, Overijsel, Neth r I a corporation of the Netherlands, as shown by the record of assignments in this office; and that the said Letters Patent shouldbe read with this correctionv therein that the same may conform to the record of the case in the Patent Office v Signed and sealed this 2nd day of January, A. D. 19to.
- Henry Van Arsdale,
Acting Commissioner of Patents.
US136513A 1935-02-27 1937-04-12 Process for manufacturing textile agents Expired - Lifetime US2173638A (en)

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NL72686A NL48113C (en) 1935-02-27 1935-02-27
FR821731T 1937-05-11

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2485573A (en) * 1945-10-05 1949-10-25 Rohm & Haas Thiocyanated phosphite esters
US2872351A (en) * 1953-11-14 1959-02-03 Bohme Fettchemie Gmbh Compositions for and methods of finishing textile materials
US3153080A (en) * 1961-01-31 1964-10-13 Eastman Kodak Co Acyloxyneopentyl and acyloxycyclobutane phosphate partial esters
US5273683A (en) * 1991-05-21 1993-12-28 Asphalt Technology & Consulting, Inc. Emulsifier for use in mixing grade emulsions
US5973037A (en) * 1996-11-27 1999-10-26 Fields; John R. Styrene ethylene butylene styrene (SEBS) copolymer rubber modified asphalt mixture

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2485573A (en) * 1945-10-05 1949-10-25 Rohm & Haas Thiocyanated phosphite esters
US2872351A (en) * 1953-11-14 1959-02-03 Bohme Fettchemie Gmbh Compositions for and methods of finishing textile materials
US3153080A (en) * 1961-01-31 1964-10-13 Eastman Kodak Co Acyloxyneopentyl and acyloxycyclobutane phosphate partial esters
US5273683A (en) * 1991-05-21 1993-12-28 Asphalt Technology & Consulting, Inc. Emulsifier for use in mixing grade emulsions
US5973037A (en) * 1996-11-27 1999-10-26 Fields; John R. Styrene ethylene butylene styrene (SEBS) copolymer rubber modified asphalt mixture

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Publication number Publication date
FR821731A (en) 1937-12-11
GB474229A (en) 1937-10-27
NL48113C (en) 1940-04-15

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