US3730903A - Wetting agents for alkaline baths - Google Patents

Wetting agents for alkaline baths Download PDF

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Publication number
US3730903A
US3730903A US00099264A US3730903DA US3730903A US 3730903 A US3730903 A US 3730903A US 00099264 A US00099264 A US 00099264A US 3730903D A US3730903D A US 3730903DA US 3730903 A US3730903 A US 3730903A
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US
United States
Prior art keywords
solution
carbon atoms
alkyl
wetting
baths
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
US00099264A
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English (en)
Inventor
F Landauer
C Beermann
M Reuter
K Lebkuecher
H Kiesling
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Hoechst AG
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Hoechst AG
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Publication of US3730903A publication Critical patent/US3730903A/en
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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M11/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/32Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond
    • D06M11/36Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond with oxides, hydroxides or mixed oxides; with salts derived from anions with an amphoteric element-oxygen bond
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/143Sulfonic acid esters
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/42Amino alcohols or amino ethers
    • C11D1/44Ethers of polyoxyalkylenes with amino alcohols; Condensation products of epoxyalkanes with amines
    • 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
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/36Organic compounds containing phosphorus
    • C11D3/362Phosphates or phosphites
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06LDRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L1/00Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
    • D06L1/12Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using aqueous solvents
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M11/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/32Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond
    • D06M11/36Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond with oxides, hydroxides or mixed oxides; with salts derived from anions with an amphoteric element-oxygen bond
    • D06M11/38Oxides or hydroxides of elements of Groups 1 or 11 of the Periodic Table
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
    • D06M13/248Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing sulfur
    • D06M13/256Sulfonated compounds esters thereof, e.g. sultones
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
    • D06M13/282Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
    • D06M13/292Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/372Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight

Definitions

  • the present invention relates to surface active agents especially to wetting agents for alkaline baths, in particular for mercerizingand leaching baths.
  • the present wetting agents are mixtures containing:
  • German Pat. No. 719,432 it is known from German Pat. No. 719,432 to use a mixture of a sulfonic acid of an alkane having 5 to 7 carbon atoms and an amine having B-hydroxyethyl residues. These mixtures, however, are not satisfactory as to their wetting power and their tendency to foam.
  • saturated aliphatic hydrocarbons are appropriate, such as light petrol boiling at 30'80 C. or aliphatic and cycloaliphatic hydrocarbons of 10-20 carbon atoms, which may be branched.
  • straightchained hydrocarbons of 10-20 carbon atoms as obtained by molecular sieve separation processes.
  • Molecular sieves are, for example, certain synthetic zeolites the crystal lattices of which having interspaces of definite dimensions which are accessible through pores of a certain width. These pores allow for example the inner adsorption of n-paraffins by excluding branched components. In a separate stage the n-paraffins are desorbed and gathered. The n-paraffins can also be separated by using the so-called urea-process.
  • At least one sulfonic acid group is introduced into the lower hydrocarbons such as into light petrol, having an average molecular weight of about 60, and 2 sulfonic acid groups into the higher hydrocarbons such as into an n-parafiin of an average molecular weight of 215.
  • the sulfonic acid alkali metal salts are prepared from these hydrocarbons advantageously by sulfo-chlorination according to the Reed-process and subsequent alkaline saponification but also the thiourea-process of Sprague and Johnson or the method of Johnson and Douglas as Well as the oxidation of alkyl sulfides with chlorine can be applied (cf. F. Asinger Chemie und Technologie der Parafiinkohlenstoiie (1956) Berlin, pages 395, 423-424).
  • Other methods of introduction of sulfonic acid groups such as the sulfoxidation can be used.
  • the alkyl dialkanolamine corresponds to the general formula in which R is alkyl of 2 to 5 carbon atoms, in is a number of 1 to 2 and n is 2 or 3.
  • the alkyl dialkanolamines advantageously should be soluble in water. There may be used, for example, 11 propyl d'iethanolamine, isoamyl diethanolamine, ethyl bis [2 hydroxy isopropyl] amine, n-butyl-bis-[Z-hydroxypropyl]-amine or preferably butyl or isobutylamine which has been reacted with 22.5 moles of ethylene oxide.
  • phosphoric acid esters those derived from ortho phosphoric acid and alkanols of a medium molecular weight, containing about 48 carbon atoms, are preferred, for example trioctylphosphate, in particular tributylphosphate and triisobutylphosphate. These phosphoric acid esters keep their activity even when partially saponified.
  • the proportions by weight of the ingredients of the mixture according to the present invention are as follows:
  • the wetting agent mixtures according to the process of the present invention are soluble in dilute as well as in highly-concentrated alkaline lyes, as they are used, for example, for mercerizing or leaching of cellulose fibres, and even in the cold.
  • EXAMPLE 1 sulfo-chlorination 120 g. of sulfur dioxide and 91 g. of chlorine are introduced at 50 C. within 10 hours into 54 g. of a straightchain alkane of an average molecular weight of 216, obtained by a molecular sieve process and irradiated with UV-rays. After blowing out, the thickly oily sulfo chloride contains 17.9% of chlorine capable of being saponified. The yield amounts to 128 g.
  • Solution A 16.7 g. of isobutyl-diethanolamine and 1.4 g. of triisobutyl phosphate are added to 40 g. of the above-mentioned sulfonate solution while stirring. There are obtained 58 g. of a clear solution having a content of 61% of surface active agent.
  • Solution A instead of the isobutyl-diethanolamine there can also be used the same amount of a reaction product of isobutylamine with 2.3 moles of ethylene oxide which leads to the same results.
  • Solution B -16.7 g. of isobutyl diethanolamine and 1.6 g. of tributylphosphate and 5.5 g. of n-butanol are added to 40 g. of a sulfonate solution obtained by the above-mentioned saponification while stirring. There are obtained 63 g. of a clear solution containing 55% of surface active agent.
  • a similar good wetting agent mixture is obtained when, instead of the isobutyl diethanolamine the same amount of n-butyldiethanolamine is used.
  • Solution C 43 g. of a commercial alkylmonosulfonate (the hydrocarbon chain having about 16 carbon atoms and containing about 77% of surface active agent) are dissolved in 53 g. of water. To this solution 37.5 g. of isobutyldiethanolamine and 8 g. of triisobutylphosphate are added. The solution contains 50% of surface active agent.
  • EXAMPLE 2 230 g. of a light petrol sulfochloride which was prepared according to the Reed process by sulfo-chlorination of a light petrol (boiling at 30-80 C. and having an average molecular weight of and which contains 16.9% of sulfur and 20.9% of chlorine and thus has about 6 carbon atoms per one SO CI group was added dropwise within one hour at 5060 C. into a solution of 104 g. of sodium hydroxide in 1 litre of water. After stirring for 1 hour, the reaction is complete. After filtration of some resinous impurities the solution contains 30% of sulfonate.
  • composition of mercerizing wetting agents is clearly soluble in mercerizing baths of 300 g. of sodium hydroxide/litre.
  • Table II shows that, because of good solubility of the products in strong alkaline baths which product combination is otbained according to the present invention, surprisingly good shrinkage values are also obtained.
  • the Wetting power was determined according to the German Industrial Standard (DIN) No. 53901 (using bakers, filled with the test liquid, in which standardized samples of cotton fabrics are inserted. The time required until sinking of the sample is a measure for the wetting power).
  • the foaming activity was determined as follows: 50 cc. of the test liquor was filled in a 100 cc. calibrated cylinder and shaken for times. The height of the foam was determined immediately (1) and 1 minute (2) after the shaking.
  • test samples indicated below contained: Sample a: 6 g. of surface active agent; Sample b: 10 g. of surface active agent-each in a solution of aqueous sodium hydroxide of 27% strength.

Landscapes

  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Textile Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
  • Paper (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
US00099264A 1967-02-02 1970-12-17 Wetting agents for alkaline baths Expired - Lifetime US3730903A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DEF0051418 1967-02-02
DE1619040A DE1619040B2 (de) 1967-02-02 1967-02-02 Netzmittel für alkalische Bäder
US9926470A 1970-12-17 1970-12-17
US331467A US3893937A (en) 1967-02-02 1973-02-12 Wetting agents for alkaline baths

Publications (1)

Publication Number Publication Date
US3730903A true US3730903A (en) 1973-05-01

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Family Applications (2)

Application Number Title Priority Date Filing Date
US00099264A Expired - Lifetime US3730903A (en) 1967-02-02 1970-12-17 Wetting agents for alkaline baths
US331467A Expired - Lifetime US3893937A (en) 1967-02-02 1973-02-12 Wetting agents for alkaline baths

Family Applications After (1)

Application Number Title Priority Date Filing Date
US331467A Expired - Lifetime US3893937A (en) 1967-02-02 1973-02-12 Wetting agents for alkaline baths

Country Status (7)

Country Link
US (2) US3730903A (fr)
BE (1) BE710271A (fr)
CH (2) CH146168A4 (fr)
DE (1) DE1619040B2 (fr)
FR (1) FR1554186A (fr)
GB (1) GB1211116A (fr)
NL (1) NL6801208A (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3893937A (en) * 1967-02-02 1975-07-08 Hoechst Ag Wetting agents for alkaline baths
EP0729500B1 (fr) * 1992-05-18 2002-09-18 Oy Faintend Ltd Procede de preparation des melanges comprenant des agents tensio-actifs

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4108597A (en) * 1976-02-12 1978-08-22 Cotton Incorporated Process for imparting pucker and color effects to fabrics
CH671668B5 (fr) * 1981-08-22 1990-03-30 Sandoz Ag
US4494952A (en) * 1982-09-08 1985-01-22 Ciba-Geigy Corporation Wetting agents and their use as mercerizing assistants
FR2551474B1 (fr) * 1983-09-01 1986-12-05 Sandoz Sa Procede de traitement de matieres textiles cellulosiques
US5259963A (en) * 1989-01-12 1993-11-09 Sandoz Ltd. Surface active compositions their production and use

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR706182A (fr) * 1929-12-18 1931-06-19 I G Farbenindustrie Ag Soc Agents auxiliaires pour l'industrie textile
DE1619040B2 (de) * 1967-02-02 1974-01-24 Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt Netzmittel für alkalische Bäder

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3893937A (en) * 1967-02-02 1975-07-08 Hoechst Ag Wetting agents for alkaline baths
EP0729500B1 (fr) * 1992-05-18 2002-09-18 Oy Faintend Ltd Procede de preparation des melanges comprenant des agents tensio-actifs

Also Published As

Publication number Publication date
US3893937A (en) 1975-07-08
DE1619040B2 (de) 1974-01-24
CH146168A4 (fr) 1970-03-13
GB1211116A (en) 1970-11-04
FR1554186A (fr) 1969-01-17
BE710271A (fr) 1968-08-02
NL6801208A (fr) 1968-08-05
DE1619040A1 (de) 1971-04-01
CH492819A (de) 1970-06-30

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