US3893937A - Wetting agents for alkaline baths - Google Patents
Wetting agents for alkaline baths Download PDFInfo
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- US3893937A US3893937A US331467A US33146773A US3893937A US 3893937 A US3893937 A US 3893937A US 331467 A US331467 A US 331467A US 33146773 A US33146773 A US 33146773A US 3893937 A US3893937 A US 3893937A
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- 239000000080 wetting agent Substances 0.000 title abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 20
- 239000003599 detergent Substances 0.000 claims abstract description 4
- -1 ALKALI METAL SALT Chemical class 0.000 claims description 12
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- GVNHOISKXMSMPX-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]ethanol Chemical group CCCCN(CCO)CCO GVNHOISKXMSMPX-UHFFFAOYSA-N 0.000 claims description 3
- HRKAMJBPFPHCSD-UHFFFAOYSA-N Tri-isobutylphosphate Chemical group CC(C)COP(=O)(OCC(C)C)OCC(C)C HRKAMJBPFPHCSD-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 16
- 125000000542 sulfonic acid group Chemical group 0.000 abstract description 7
- 239000002253 acid Substances 0.000 abstract description 3
- 150000003973 alkyl amines Chemical class 0.000 abstract description 3
- 229910019142 PO4 Inorganic materials 0.000 abstract description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract description 2
- 239000010452 phosphate Substances 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 2
- UKGJZDSUJSPAJL-YPUOHESYSA-N (e)-n-[(1r)-1-[3,5-difluoro-4-(methanesulfonamido)phenyl]ethyl]-3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CCCC1=NC(C(F)(F)F)=CC=C1\C=C\C(=O)N[C@H](C)C1=CC(F)=C(NS(C)(=O)=O)C(F)=C1 UKGJZDSUJSPAJL-YPUOHESYSA-N 0.000 description 1
- JIRBSEKRPPNRON-UHFFFAOYSA-N 2-[2-hydroxyethyl(3-methylbutyl)amino]ethanol Chemical compound CC(C)CCN(CCO)CCO JIRBSEKRPPNRON-UHFFFAOYSA-N 0.000 description 1
- OZICRFXCUVKDRG-UHFFFAOYSA-N 2-[2-hydroxyethyl(propyl)amino]ethanol Chemical compound CCCN(CCO)CCO OZICRFXCUVKDRG-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- 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 Table
-
- 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
- ABSTRACT Detergent mixtures comprising a) an alkylsulfonic acid deriving from a light petrol and 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 wetting agents for alkaline baths.
- R represents an alkyl radical of 2 to 5 carbon atoms
- n represents the integer 2 or 3
- m represents a number of l to 2 and c. an ester of phosphoric acid and of alkanols of 4'to 8 carbon atoms, and if desired, further usual auxili-i ary agents.
- mixtures of a) aliphatic sulfonic acids deriving from light petrol containing on an average one sulfonic acid group per 7 carbon atoms or their alkali metal salts, b) lower alkyl dialkanolamines and c) phosphoric acid esters of alkanols of 4 to 8 carbon atoms for foam reduction, which may be partially saponified, are used as extremely active and clearly soluble wetting agents even in cold alkaline baths.
- mercerizing baths which are practically free of foam. This is especially advantageous when working on yarn mercerizing machines.
- 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.
- the sulfonic acid alkaligmetal salts are prepared from these hydrocarbons advantageously by sulfo-chlorination according to the Reedprocess and subsequent alkaline saponification; but also the thioureaprocess ofv Sprague andJohnson or the m ethod of Johnson and Douglas as well as-the oxidation of alkyl sulfides with chlorine can be applied (cf. F. Asinger Chemie und Technologie der Paraffinkohlenstoffe, (1956) Berlin, pages 395, 423 4 424). Other methods of introduction of sulfonic acid groups, such as the-'sulfoxidation can be used.
- the lowertalkyl dialkanolamine corresponds. to the general formula in which R represents an alkyl radical of 2 5 carbon atoms and'm represents a number of 1 to 2'andf n is 2 or 3.
- phosphoric acid esters keeptheir activity' evenawhen partially saponified.
- i a 1 The proportion by weight of the alkyl sulfonates to the alkyl dialkanolamines is to be 1 0.3 to l 5, preferably l 0.8 to 1 2.
- the amount of the phosphoric acid ester added is l 15 percent, referred to the total of the sulfonates and alkyl dialkanolamines, preferably 2 6 percent.
- 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.
- composition of mercerizing wetting agents is clearly soluble in mercerizing baths of 300 g of sodium hydroxide/litre.
- R is alkyl of-2 to carbon atoms, nis 2 or 3 and m is a number of l to 2, and
- composition as claimed in claim 1 consisting of a. about to about 55 percent by weight of said sulfonic acid or sulfonate,
- a composition as claimed in claiml wherein the l. Detergent mixture consisting essentially of a. about 10 to about 80 percent by weight of an alkyl sulfonic acid derived from light petrol boiling at 30- 80C or an alkali metal salt thereof, having on an average one sulfonic acid group per 7 carbon atoms at most or a mixturethereof, b. about 20. to about 85 percent by weight of an amine of the formula R N 1 n 2n )m 2 4.
- the amine is butyldiethanolamine.
- composition as claimed in claim 1 Wh'erein'the ester is triisobu'tylphosphate.
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- 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)
Abstract
Detergent mixtures comprising a) an alkylsulfonic acid deriving from a light petrol and 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 wetting agents for alkaline baths.
Description
United States Patent Landauer et al.
[451 *July 8, 1975 WETTING AGENTS FOR ALKALINE BATHS Inventors: Franz Landauer, Frankfurt am Main;
Claus Beermann, Neu-Isenburg; MartinReuter, Kronberg, Taunus; Karl Heinz Lebkucher, Hoiheim, Taunus; Hubert Kiesling, Schwalbach, Taunus, all of Germany Hoechst Aktiengesellschaft, Frankfurt am Main, Germany Assignee:
Notice: The portion of the term of this patent subsequent to May 1, 1990, has been disclaimed.
Filed: Feb. 12, 1973 Appl. No.: 331,467
Related US. Application Data Continuation-in-part of Ser. No. 99,264, Dec. 17,
1970, Pat. No. 3,730,903, which is a continuation-in-part of Ser. No. 701,119, Jan. 29, 1968, abandoned.
Foreign Application Priority Data Feb. 2, 1967 Germany 1619040 US. Cl. 252/156; 252/117; 252/121; 252/161; 252/554; 8/125; 8/127 [51] Int. Cl Clld 7/12 [58] Field of Search 252/156, 117, 121, 161, 252/554; 23/125, 127
Netherlands 252/5 3 3 Primary ExaminerLeland A. Sebastian Assistant Examiner-B. Hunt Attorney, Agent, or Firm-Curtis, Morris & Safford [5 7] ABSTRACT Detergent mixtures comprising a) an alkylsulfonic acid deriving from a light petrol and 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 wetting agents for alkaline baths.
5 Claims, No Drawings 1,. wETTlNGrAGENTs FOR .ALKALINEBATH'S,
in which R represents an alkyl radical of 2 to 5 carbon atoms, n represents the integer 2 or 3 and m represents a number of l to 2 and c. an ester of phosphoric acid and of alkanols of 4'to 8 carbon atoms, and if desired, further usual auxili-i ary agents. I it is already known form German Auslegeschrift No. 1 ,014,067 that high moljectilaf weight aliphatic sulfonic acids contaiiting tn or tharij'one .sulfonicgacid groupper molecule are used as wttihg agent for 'm'e'rcj'erizingnd h ng. aths.-. Q' f Y Furthermore, islcnown from Grrnafl Pat. No. 955,857 that mixtures of alkyl'sulforiats bf'S to l carbon atoms .in; the alkyhradical and alkyl sulfates, the alkyl radical of whiclizcontaining l0 16- cafbon 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.
It has been found that mixtures of a) aliphatic sulfonic acids deriving from light petrol containing on an average one sulfonic acid group per 7 carbon atoms or their alkali metal salts, b) lower alkyl dialkanolamines and c) phosphoric acid esters of alkanols of 4 to 8 carbon atoms for foam reduction, which may be partially saponified, are used as extremely active and clearly soluble wetting agents even in cold alkaline baths.
It was surprising and unforeseeable that the addition of the alkyl dialkanolamines to the mentioned alkyl sul fonic acids or their alkali metal salts leads to such active, clearly soluble wetting agents. The technical advantages of the wetting agent-mixtures to the process of the present invention are, for example, to be seen from the table shown further below. Especially advantageous in industrial use are the highly improved shrinkage values obtained with said mixtures.
Due to the phosphoric acid esters there are obtained mercerizing baths which are practically free of foam. This is especially advantageous when working on yarn mercerizing machines. To the mercerizing or 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 substances for the preparation of the alkyl sulfonic acids, containing per one sulfonic acid group at most 7 carbon atoms, saturated aliphatic hydrocarbons 'areappropriate such,1;f,o example, as light petrol boiling at 30 80?, t. Q
According to the present invention at least one sulfonic acidgroup visintnod-ucecl into .thelight petrol, having anaverage molecular weight of aboutL60. The sulfonic acid alkaligmetal salts are prepared from these hydrocarbons advantageously by sulfo-chlorination according to the Reedprocess and subsequent alkaline saponification; but also the thioureaprocess ofv Sprague andJohnson or the m ethod of Johnson and Douglas as well as-the oxidation of alkyl sulfides with chlorine can be applied (cf. F. Asinger Chemie und Technologie der Paraffinkohlenstoffe, (1956) Berlin, pages 395, 423 4 424). Other methods of introduction of sulfonic acid groups, such as the-'sulfoxidation can be used.
The lowertalkyl dialkanolamine corresponds. to the general formula in which R represents an alkyl radical of 2 5 carbon atoms and'm represents a number of 1 to 2'andf n is 2 or 3. The alkyl dialkanolaminesadvantageously should be soluble in water. There may be used, forexample, n-propyl-diethanolamine, isoamyl-diethanolamine, ethyl-bis- 2-hydroxy-isopropyl -amine n-butyl-bis 2- hydroxypropyl1-amine or preferably buty l or isobutyla mine which "has"b"een reacted 2 52.5 trnoles of ethylene oxide.
Asiphosphoric acid esters which may beaddedthose derived from alito l'io'ls, esp'e'icial-ly' alkanols of 'a rriedium molecular weight, containing about'4='" 8 carbon atoms,
are preferred, for example-trioctylphosphate, in particular tributylph'osphate anditrii'sobutylphosphatc.- These phosphoric acid esters keeptheir activity' evenawhen partially saponified. i a 1 The proportion by weight of the alkyl sulfonates to the alkyl dialkanolamines is to be 1 0.3 to l 5, preferably l 0.8 to 1 2. The amount of the phosphoric acid ester added is l 15 percent, referred to the total of the sulfonates and alkyl dialkanolamines, preferably 2 6 percent.
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 Example serves to illustrate the invention but it is not intended to limit it thereto.
EXAMPLE 230 g of a light petrol sulfochloride which was prepared according to the Reed process by sulfochlorination of a light petrol (boiling at 30- 80C and having an average molecular weight of and which contains 16.9 percent of sulfur and 20.9 percent of chlorine and thus has about 6 carbon atoms per one SO Cl group was added dropwise within one hour at 50- 60C 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 percent of sulfonate.
Preparation of the mercerizing agent solution:
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 percent 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.
1n the following Table the shrinkage values of the product of the present invention of the Example are given. The Table shows that because of good solubility of the products in strong alkaline baths which product combination is obtained according to the present invention, surprisingly good shrinkage values are also obtained.
Table in which R is alkyl of-2 to carbon atoms, nis 2 or 3 and m is a number of l to 2, and
c. about 1 to about percent by weight of a phosphoric acid ester of alkanols of 4 to 8 carbon atoms. 2. A composition as claimed in claim 1, consisting of a. about to about 55 percent by weight of said sulfonic acid or sulfonate,
b. about 40 to about 65 percent by weight of said amine and c. about 2 to about 6 percent by weight of said ester.
Shrinkage values measured in baths of 300 g of sodium hydroxide/litre according to the method given in Praktikum der Textilveredlung, Otto Meechels, page 24, (1949). Springer Verlag, Berlin-Goettingen-Heidelberg shrinkage (in at 15C) after. surface active 30 sec. 60 sec. 120 sec. 18 sec. 240 sec.
agent/litre we clam: 3. A composition as claimed in claiml, wherein the l. Detergent mixture consisting essentially of a. about 10 to about 80 percent by weight of an alkyl sulfonic acid derived from light petrol boiling at 30- 80C or an alkali metal salt thereof, having on an average one sulfonic acid group per 7 carbon atoms at most or a mixturethereof, b. about 20. to about 85 percent by weight of an amine of the formula R N 1 n 2n )m 2 4. A composition as claimed in claim 1, wherein the amine is butyldiethanolamine.
5. A composition as claimed in claim 1, Wh'erein'the ester is triisobu'tylphosphate.
Claims (5)
1. A DETERGENT MIXTURE CONSISTING ESSENTIALLY OF A. ABOUT 10 TO ABOUT 80 PERCENT BY WEIGHT OF AN ALKYL SULFONIC ACID DERIVED FROM LIGHT PETROL BOILING AT 30*- 80*C OR AN ALKALI METAL SALT THEREOF, HAVING ON AN AVERAGE ONE SULFONIC ACID GROUP PER 7 CARBON ATOMS AT MOST OR A MIXTURE THEREOF, B. ABOUT 20 TO ABOUT 85 PERCENT BY WEIGHT OF AN AMINE OF THE FORMULA R-N( (CNH2N-0)M'') 2 IN WHICH R IS ALKYL OF 2 TO 5 CARBON ATOMS, N IS 2 OR 3 AND M IS A NUMBER OF 1 TO 2, AND C. ABOUT 1 TO AAABOUT 15 PERCENT BY WEIGHT OF A PHOSPHORIC ACID ESTER OF ALKANOLS OF 4 TO 8 CARBON ATOMS.
2. A composition as claimed in claim 1, consisting of a. about 30 to about 55 percent by weight of said sulfonic acid or sulfonate, b. about 40 to about 65 percent by weight of said amine and c. about 2 to about 6 percent by weight of said ester.
3. A composition as claimed in claim 1, wherein the sulfonic acid is derived from a light petrol having an average molecular weight of about 70.
4. A composition as claimed in claim 1, wherein the amine is butyldiethanolamine.
5. A composition as claimed in claim 1, wherein the ester is triisobutylphosphate.
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE1619040A DE1619040B2 (en) | 1967-02-02 | 1967-02-02 | Wetting agent for alkaline baths |
NL6801208A NL6801208A (en) | 1967-02-02 | 1968-01-26 | |
GB4946/68A GB1211116A (en) | 1967-02-02 | 1968-01-31 | Detergent mixtures and their use in alkaline baths for cellulose fibres |
CH146168D CH146168A4 (en) | 1967-02-02 | 1968-01-31 | |
CH146168A CH492819A (en) | 1967-02-02 | 1968-01-31 | Low-foaming wetting agent for mercerising and caustic baths |
BE710271D BE710271A (en) | 1967-02-02 | 1968-02-02 | |
FR1554186D FR1554186A (en) | 1967-02-02 | 1968-02-02 | |
US00099264A US3730903A (en) | 1967-02-02 | 1970-12-17 | Wetting agents for alkaline baths |
US331467A US3893937A (en) | 1967-02-02 | 1973-02-12 | Wetting agents for alkaline baths |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF0051418 | 1967-02-02 | ||
DE1619040A DE1619040B2 (en) | 1967-02-02 | 1967-02-02 | Wetting agent for alkaline baths |
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 |
---|---|
US3893937A true US3893937A (en) | 1975-07-08 |
Family
ID=27430609
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 Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00099264A Expired - Lifetime US3730903A (en) | 1967-02-02 | 1970-12-17 | Wetting agents for alkaline baths |
Country Status (7)
Country | Link |
---|---|
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 (3)
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 |
US4494952A (en) * | 1982-09-08 | 1985-01-22 | Ciba-Geigy Corporation | Wetting agents and their use as mercerizing assistants |
US5259963A (en) * | 1989-01-12 | 1993-11-09 | Sandoz Ltd. | Surface active compositions their production and use |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1619040B2 (en) * | 1967-02-02 | 1974-01-24 | Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt | Wetting agent for alkaline baths |
CH671668B5 (en) * | 1981-08-22 | 1990-03-30 | Sandoz Ag | |
FR2551474B1 (en) * | 1983-09-01 | 1986-12-05 | Sandoz Sa | PROCESS FOR TREATING CELLULOSIC TEXTILE MATERIALS |
FI91278C (en) * | 1992-05-18 | 1995-04-18 | Ks Chemitra Ltd Oy | Method for preparing surfactant mixtures |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1914331A (en) * | 1929-12-18 | 1933-06-13 | Ig Farbenindustrie Ag | Treatment of textile materials with aqueous liquids |
US3730903A (en) * | 1967-02-02 | 1973-05-01 | Hoechst Ag | Wetting agents for alkaline baths |
-
1967
- 1967-02-02 DE DE1619040A patent/DE1619040B2/en active Pending
-
1968
- 1968-01-26 NL NL6801208A patent/NL6801208A/xx unknown
- 1968-01-31 CH CH146168D patent/CH146168A4/xx unknown
- 1968-01-31 GB GB4946/68A patent/GB1211116A/en not_active Expired
- 1968-01-31 CH CH146168A patent/CH492819A/en not_active IP Right Cessation
- 1968-02-02 BE BE710271D patent/BE710271A/xx unknown
- 1968-02-02 FR FR1554186D patent/FR1554186A/fr not_active Expired
-
1970
- 1970-12-17 US US00099264A patent/US3730903A/en not_active Expired - Lifetime
-
1973
- 1973-02-12 US US331467A patent/US3893937A/en not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1914331A (en) * | 1929-12-18 | 1933-06-13 | Ig Farbenindustrie Ag | Treatment of textile materials with aqueous liquids |
US3730903A (en) * | 1967-02-02 | 1973-05-01 | Hoechst Ag | Wetting agents for alkaline baths |
Cited By (3)
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 |
US4494952A (en) * | 1982-09-08 | 1985-01-22 | Ciba-Geigy Corporation | Wetting agents and their use as mercerizing assistants |
US5259963A (en) * | 1989-01-12 | 1993-11-09 | Sandoz Ltd. | Surface active compositions their production and use |
Also Published As
Publication number | Publication date |
---|---|
US3730903A (en) | 1973-05-01 |
DE1619040B2 (en) | 1974-01-24 |
CH146168A4 (en) | 1970-03-13 |
GB1211116A (en) | 1970-11-04 |
FR1554186A (en) | 1969-01-17 |
BE710271A (en) | 1968-08-02 |
NL6801208A (en) | 1968-08-05 |
DE1619040A1 (en) | 1971-04-01 |
CH492819A (en) | 1970-06-30 |
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