US3730903A - Wetting agents for alkaline baths - Google Patents

Wetting agents for alkaline baths Download PDF

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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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solution
carbon atoms
alkyl
wetting
baths
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F Landauer
C Beermann
M Reuter
K Lebkuecher
H Kiesling
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Hoechst AG
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M11/00—Treating 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
    • D06M11/32—Treating 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
    • D06M11/36—Treating 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
    • 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
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/143—Sulfonic acid esters
    • 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
    • C11D1/38—Cationic compounds
    • C11D1/42—Amino alcohols or amino ethers
    • C11D1/44—Ethers of polyoxyalkylenes with amino alcohols; Condensation products of epoxyalkanes with amines
    • 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
    • C11D3/36—Organic compounds containing phosphorus
    • C11D3/362—Phosphates or phosphites
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
    • D06L1/12—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using aqueous solvents
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M11/00—Treating 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
    • D06M11/32—Treating 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
    • D06M11/36—Treating 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
    • D06M11/38—Oxides or hydroxides of elements of Groups 1 or 11 of the Periodic System
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244—Treating 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
    • D06M13/248—Treating 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
    • D06M13/256—Sulfonated compounds esters thereof, e.g. sultones
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244—Treating 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
    • D06M13/282—Treating 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
    • D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating 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
    • D06M13/372—Treating 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.

Abstract

DETERGENT MIXTURES CONSISTING OF: (A) AN ALKYLSULFONIC ACID CONTAINING A SULFONIC ACID GROUP PER 7 CARBON ATOMS AT MOST, (B) A LOW-MOLECULAR OXALKYLATION PRODUCT OF A LOWER ALKYL AMINE, AND (C) A PHOSPHATE OF ALKANOLS OF 4 TO 8 CARBON ATOMS ARE USEFUL AS SURFACE ACTIVE AGENTS FOR ALKALINE BATHS.

Description

United States Patent Claims priority, application Germany, Feb. 2, 1967, F 51 418 Int. Cl. cild 7/12 as. C]. 252-156 2 Claims ABSTRACT OF THE DISCLOSURE Detergent mixtures consisting of: (a) an alkylsulfonic acid containing a sulfonic acid group per 7 carbon atoms at most, (b) a lowmolecular oxalkylation product of a lower alkyl amine, and (c) a phosphate of alkanols of 4 to 8 carbon atoms are useful as surface active agents for alkaline baths.
This is a continuation-in-part of our copending application Ser. No. 701,119 filed Jan. 29, 1968, now abandoned.
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:
(a) alkyl sulfonic acids or their alkali metal salts having on an average one sulfonic acid group per 7 carbon atoms at most,
(b) an amine of the formula in which R is alkyl of 2 to carbon atoms, n is 2 or 3 and m is a number of 1 to 2, which amines are in the following referred to as alkyl dialkanol amines, and (c) a phosphoric acid ester of alkanols of 4 to 8 carbon atoms, and, if desired, further usual auxiliary agents.
It is already known from German Auslegeschrift No. 1,014,067 that higher molecular weight aliphatic sulfonic acids containing more than one sulfonic acid group per molecule are used as wetting agent for mercerizingand leaching baths.
Furthermore, it is known from German Pat. No. 955,- 857 that mixtures of alkyl sulfonates of 5 to carbon atoms in the alkyl radical and alkyl sulfates, the alkyl radical of which containing 10-16 carbon atoms can be used as wetting agents for mercerizing baths. Additionally, in order to improve the solubility of the sulfonates in the mercerizing liquors, small amounts of aliphatic alcohols, amines, alkylamines, ether alcohols or naphthene acids can be used as auxiliary solvent.
Moreover, 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.
It has been found that mixtures of: (a) aliphatic sulfonic acids containing on an average one sulfonic acid group per 7 carbon atoms or their alkali metal salts, (b) alkyl dialkanolamines, and (c) phosphoric acid esters of aliphatic alcohols of an average molecular weight, which may be partially saponified are used as extremely active and clearly. soluble wetting agents even in cold alkaline baths.
Patented May 1, 1973 It was surprising and unforeseeable that the addition of the alkyl dialkanolamines and of the phosphates to the mentioned alkyl sulfonic acids or their alkali metal salts leads to such active, clearly soluble and not-foaming wetting agents. The technical advantages of the wetting agent-mixtures according to the process of the present invention are, for example, to be seen from the tables shown further below. Especially advantageous in industrial use are the mixtures according to the present invention for obtaining highly improved shrinkage values. The fact, that the mercerizing baths are practically free of foam is especially advantageous when working on yarn mercerizing machines. To the mercerizingor leaching baths prepared by using the mixtures of the present invention other surface active compounds or mercerizing agents can be added, if desired, such as ethylene oxide condensation products or cresols. If it is deemed desirable, other known auxiliaries, such as lower alcohols, can still be added.
As starting substance for the preparation of the alkyl sulfonic acids, containing per one sulfonic acid group at most 7 carbon atoms, 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. Especially advantageous are 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.
The above-mentioned molecular-sieve-process is described for example in the publication of J. J. Griesmer, H. B. Rhodes and K. Kiyonaga, Erdoel und Kohle, Erdgas, Petrochemie, 13, (1960), page 650, in the publication of Ch. K. Hersh, Molecular sieves, New York (1961) and in Ind. Engng. Chem., 54 (1962), No. 5, page 13 and Erdoel and Kohle, 12 (1959), page 406.
The urea-process is explained in a paper of E. Weingaertner in Erdoel und Kohle, Erdgas, Petrochemie, 14 (1961), page 910.
According to the process of the present invention 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.
As 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:
(a) about to about 80%, preferably about 30 to about 55% of alkyl sulfonate,
(b) about 20 to about 85%, preferably about 40 to about 65% of alkyl dialkanol amine and (c) about 1 to about preferably about 2 to about 6% of phosphate.
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.
The following examples serves to illustrate the invention but they are not intended to limit it thereto.
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.
Analysis: S: 15.1%, CI: 28.3%, i.e. the product corresponds to the formula (CH (SO Cl Saponification 116 g. of the above-mentioned sulfo chloride are added dropwise to 158 g. of a sodium hydroxide solution of 33.4% at 50-70 C. Then the solution is stirred for 1 hour at 60-70 C., cooled and then filtered under suction from the sodium chloride which has precipitated. The clear aqueous solution then contains 46.3% of sulfonate.
Adjustment of mercerizing agents:
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.
The values of wetting of the following comparative test are given in Table I with the solutions A and B according to the present invention. Furthermore, the isobutyldiethanolamine is also tested.
4 The determination of the wetting value is carried out in a bath containing 300 g. of sodium hydroxide according to DIN 53 901. When using 5 g. per litre of an active wetting substance the wetting times given in Table I are obtained.
TABLE I Wetting time in sec. Solution A 46 Solution B Alkanepolysulfonate (Example 1) 300 Solution C 300 Isobutyl diethanolamine 74 The results show that the combination according to the present invention has surprisingly good wetting values.
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.
Preparation of the mercerizing agent solution (=solution D): 70.5 g. of the above-mentioned light petrol sulfonate solution (containing 21.2 g. of sulfonate) are mixed, while stirring, with 37.5 g. of butyldiethanolamine, 26 g. of water and 8 g. of triisobutylphosphate. The clear solution then contains 42% of surface active agent.
This composition of mercerizing wetting agents is clearly soluble in mercerizing baths of 300 g. of sodium hydroxide/litre.
The light petrol sulfonate alone (i.e. without additions) soon creams up in these baths, i.e. it is useless.
In the following Table II the shrinkage values of the products of the present invention of Example 1 (=solutions A and B) and Example 2 (=solution D) are compared with (1) alkanepolysulfonate of Example 1, (2) a mixture of commercial alkylmonosulfonate with isobutylethanolamine (solution C).
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.
TABLE II Shrinkage values measured in baths of 300 g. of sodium hydroxide/litre according to the method given in Yraktikum der Textilveredlnng", Otto Meechels, page 24, (1949), Springer Verlag, Berlin-Goottingen- Heidelberg Shrinkage (in percent at 15 C.) after- 30 60 75 Grams of surface active agent/litre see. sec. see. sec. sec.
SolutionA:
0.0 10.8 12.8 13.0 13,2 5 8.0 11.0 12.4 13.0 13.5 Alkanepolysulionate (according to Example1):6 1.6 4.2 8.4 11.2 13.2 Solution 0:5 5.4 8.6 11.4 12.8
EXAMPLE 3 Solution B was compared with an analogous solution but which contained no tributyl phosphate=solution B 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.
The 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.
Foaming activity Wetting power (seconds) Sample a Sample b Solution Sample a Sample 1) (1) (2) (l) (2) B l 77 28 20 3 2O 4 We claim 6 vided on an average per one sulfonic acid group at most 7 carbon atoms are present in said molecule; (b) about 20 to 85% by Weight of an amine of the formula R N[ n 2n )m ]2 in which R is alkyl of 2 to 5 carbon atoms, in is 2 or 3 and m is a number from 1 to 2; and (c) about 1 to 15% by weight of a phosphoric acid triester of monohydric alkanols of 4 to 8 carbon atoms. 2. The composition as claimed in claim 1, consisting of: (a) about 30 to about by weight of said sulfonate, (b) about 40 to about by weight of said amine and (c) about 2 to about 6% by weight of said phosphate.
References Cited UNITED STATES PATENTS 1,914,331 6/1933 Nuesslein et a1. 8-137 FOREIGN PATENTS 955,857 1/1957 Germany 8-127 480,837 3/1938 Great Britain 8127 776,360 5/1957 Great Britain 252554 475,675 11/1957 Great Britain 8-127 6709714 l/l968 Netherlands 252533 MAYER WEINBLATT, Primary Examiner US. Cl. X.R.
US00099264A 1967-02-02 1970-12-17 Wetting agents for alkaline baths Expired - Lifetime US3730903A (en)

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DE1619040A DE1619040B2 (en) 1967-02-02 1967-02-02 Wetting agent for alkaline baths
DEF0051418 1967-02-02
US9926470A 1970-12-17 1970-12-17
US331467A US3893937A (en) 1967-02-02 1973-02-12 Wetting agents for alkaline baths

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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

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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)

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

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 (en) * 1992-05-18 2002-09-18 Oy Faintend Ltd Process for the preparation of mixtures comprising tenside

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 (en) * 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 (en) * 1983-09-01 1986-12-05 Sandoz Sa PROCESS FOR TREATING CELLULOSIC TEXTILE MATERIALS
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 (en) * 1929-12-18 1931-06-19 I G Farbenindustrie Ag Soc Auxiliary agents for the textile industry
DE1619040B2 (en) * 1967-02-02 1974-01-24 Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt Wetting agent for alkaline baths

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 (en) * 1992-05-18 2002-09-18 Oy Faintend Ltd Process for the preparation of mixtures comprising tenside

Also Published As

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

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