US2173638A - Process for manufacturing textile agents - Google Patents

Process for manufacturing textile agents Download PDF

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Publication number
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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United States
Prior art keywords
acid
alcohol
phosphorus
high molecular
molecular weight
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Expired - Lifetime
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US136513A
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English (en)
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Rozenbroek Meindert Danius
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Individual
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    • 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
    • C07F9/103Extraction or purification by physical or chemical treatment of natural phosphatides; Preparation of compositions containing phosphatides of unknown structure
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02Boron compounds
    • C07F5/04Esters of boric acids
    • 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
    • C11D1/34Derivatives of acids of phosphorus
    • C11D1/347Other P-containing anionic compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/02Water
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125Carboxylix 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
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40Fatty vegetable or animal oils
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40Fatty vegetable or animal oils
    • C10M2207/404Fatty vegetable or animal oils obtained from genetically modified species
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/042Metal salts thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2227/00Organic 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
    • C10M2227/06Organic compounds derived from inorganic acids or metal salts
    • C10M2227/061Esters derived from boron
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/46Textile oils
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/03Organic 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.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
US136513A 1935-02-27 1937-04-12 Process for manufacturing textile agents Expired - Lifetime US2173638A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NL72686A NL48113C (en)) 1935-02-27 1935-02-27
FR821731T 1937-05-11

Publications (1)

Publication Number Publication Date
US2173638A true US2173638A (en) 1939-09-19

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US136513A Expired - Lifetime US2173638A (en) 1935-02-27 1937-04-12 Process for manufacturing textile agents

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US (1) US2173638A (en))
FR (1) FR821731A (en))
GB (1) GB474229A (en))
NL (1) NL48113C (en))

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

Also Published As

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

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