US2094489A - Wetting-out - Google Patents
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- US2094489A US2094489A US2094489DA US2094489A US 2094489 A US2094489 A US 2094489A US 2094489D A US2094489D A US 2094489DA US 2094489 A US2094489 A US 2094489A
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- wetting
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 22
- 150000002191 fatty alcohols Chemical class 0.000 description 22
- 239000002253 acid Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 18
- -1 e. g. Chemical class 0.000 description 16
- 125000004432 carbon atoms Chemical group C* 0.000 description 14
- 150000007513 acids Chemical class 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 150000001298 alcohols Chemical class 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 235000013162 Cocos nucifera Nutrition 0.000 description 8
- 240000007170 Cocos nucifera Species 0.000 description 8
- 210000002268 Wool Anatomy 0.000 description 8
- 235000011187 glycerol Nutrition 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 238000006722 reduction reaction Methods 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 239000004753 textile Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000009736 wetting Methods 0.000 description 8
- 150000005215 alkyl ethers Chemical class 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 230000000875 corresponding Effects 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- CTKINSOISVBQLD-UHFFFAOYSA-N glycidol Chemical class OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 6
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019865 palm kernel oil Nutrition 0.000 description 6
- 239000003346 palm kernel oil Substances 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 6
- 239000001117 sulphuric acid Substances 0.000 description 6
- 235000011149 sulphuric acid Nutrition 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L Sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 4
- 235000015450 Tilia cordata Nutrition 0.000 description 4
- 235000011941 Tilia x europaea Nutrition 0.000 description 4
- 229910052783 alkali metal Chemical group 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 238000004508 fractional distillation Methods 0.000 description 4
- 239000004571 lime Substances 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 230000003472 neutralizing Effects 0.000 description 4
- 125000004430 oxygen atoms Chemical group O* 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- OIQLZRMTKKPPPE-UHFFFAOYSA-N 1,1-dihydroxypropane-1-sulfonic acid Chemical compound CCC(O)(O)S(O)(=O)=O OIQLZRMTKKPPPE-UHFFFAOYSA-N 0.000 description 2
- WLXGQMVCYPUOLM-UHFFFAOYSA-N 1-hydroxyethanesulfonic acid Chemical compound CC(O)S(O)(=O)=O WLXGQMVCYPUOLM-UHFFFAOYSA-N 0.000 description 2
- QPVYSIXKPUDBJG-UHFFFAOYSA-N 3,3-dihydroxypropane-1-sulfonic acid Chemical compound OC(O)CCS(O)(=O)=O QPVYSIXKPUDBJG-UHFFFAOYSA-N 0.000 description 2
- 229920002955 Art silk Polymers 0.000 description 2
- 210000001736 Capillaries Anatomy 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N Cetyl alcohol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N Cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N Oleyl alcohol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
- 235000009470 Theobroma cacao Nutrition 0.000 description 2
- 240000000280 Theobroma cacao Species 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001340 alkali metals Chemical group 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 230000005591 charge neutralization Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 159000000011 group IA salts Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000008233 hard water Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Chemical class [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000001264 neutralization Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- RVSCBJNWEMQNJZ-UHFFFAOYSA-N octadec-1-ene-1,1-diol Chemical compound CCCCCCCCCCCCCCCCC=C(O)O RVSCBJNWEMQNJZ-UHFFFAOYSA-N 0.000 description 2
- 229940055577 oleyl alcohol Drugs 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 230000003389 potentiating Effects 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- LUIGSJYSMIUMPK-UHFFFAOYSA-N propane-1-sulfonoperoxoic acid Chemical class CCCS(=O)(=O)OO LUIGSJYSMIUMPK-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 238000000844 transformation Methods 0.000 description 2
- 230000001131 transforming Effects 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/14—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by sulfoxidation, i.e. by reaction with sulfur dioxide and oxygen with formation of sulfo or halosulfonyl groups
-
- 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
- C11D1/16—Sulfonic acids or sulfuric acid esters; Salts thereof derived from divalent or polyvalent alcohols
Definitions
- the present invention has for an object the provision of improved wetting-out, washingcleansing-, foamingand dispersing agents.
- the wetting-out and emulsifying agents suitable for washing and cleansing purposes hitherto employed include sulphuric acid esters of the higher molecular fatty alcohols as well as higher molecular alkyl sulphonic acids in their original state or in the form of their neutralization products.
- estcrlike sulphuric acid derivatives Compared with the aforesaid estcrlike sulphuric acid derivatives, it is true that the salts of the alkyl sulphonic acids distinguish themselves by extremely increased stability, but in the cold they are much less soluble so that their employment is limited to operations which can be carried out at higher temperatures, e. g., at temperatures of more thanabout 60 C. Moreover from experience to date, it appears that the feel, i. e.,
- alkyl ethers of the hydroxyalkylsulphonic acids formed with higher molecular alcohols are of a better solubility in the cold, and besides possess good stability against acids, lime and magnesia salts. These com-.- pounds are therefore preferable for use for textile-chemical operations to be carried out at lower temperatures, e.'g., for the cleansing of wool and silk, for the dyeing of artificial silk and the like.
- These new compounds are formed by the alkoxylation of mono-hydroxyor poly-hydroxyalkylsulphonic acids with higher molecular fatty alcohols, e. g., by the alkoxylation of hydroxyethane-sulfonic acid or di-hydroxypropanesulphonic acid.
- glycide compounds such as, e. g., ethylene oxideor propylene oxide; one breaks down the ethylene oxide ring by alkoxylation and forms at the same time a hydroxyl group.
- the hydroxyl group after esteriflcation with halogen hydracid is in turn replaced by the sulphonic acid group.
- Unsaturated alcohols such as oleyl alcohol and its homologues are, however, likewise to be taken into consideration.
- Polyhydroxy saturated or unsaturated alcohols may also be used, such as hydroxystearyl alcohol or ricinoleyl alcohol (dihydroxyoctadecene) obtained by reducing castor oil according to the reduction method of Bouvealt and Blane.
- the new products in the form of the alkaline salts, comprise crystalline masses of excellent capillary active properties.
- a description is given for a particular method for the manufacture of such a product and a manner in which it may be used, it being understood, however, that the scope of the invention is not limited to the therein described manner of performance or the'proportional quantities.
- Ezrampla-ZSO parts by weight of a fatty alcohol mixture (first runnings of the fatty alcohol mixtures obtained by catalytic reduction of cocoafat and distilling up to 130 C. at 3 mm. pressure of mercury) are heated for 16 hours to 115-120 C. in an open vessel together with 150 parts by weight of epichlorhydrine and 6 parts by weight of concentrated sulphuric acid.
- the reaction mixture is freed from sulphuric acid by boiling with water and is purified from by-products by fractional distillation.
- the main fraction boiling between 150 and 195 C. at 12 mm. pressure of mercury contains 13.2% of chlorine and is re-
- the thus obtained reaction product is clearly soluble even in hard water at to C. and it develops a stable lather.
- the method of producing a di-alkyl ether sulfonic acid salt which comprises preparing an ether from a glycide and a fatty alcohol having 8 or more carbon atoms in the molecule, and reacting a chloride of said ether in which the chlorine is attached to the glycide radical of said ether with sodium sulflte to produce a sodium salt of the sulfonated ether.
- dialkyl ether sulfonic acid salt which comprises reacting'epichlorhydrine with a fatty alcohol having 8 or more carbon atoms in the molecule in the presence of sulfuric acid and converting the product with sodium sulflte to produce sulfonic compounds.
- a wetting and cleansing textile treatment agent consisting of an ether having in its formula on one side of the etherial oxygen atom a fatty alkyl radical containing 8 or more carbon atoms and on the other side a radical of an hydroxy propane sulfonate salt, the cation of which is an alkaline metal imparting water solubility properties to the ether.
- a wetting and cleansing textile treating agent comprising the sulfonate of propane etherifled withan alcohol radical selected from the group consisting of fatty alcohol radicals of at least 8 carbon atoms and naph-.
- acid derivativ'es of ethers comprising forming a chloride of an ether by a process which includes reacting a glycide with a fatty alcohol having at least 8 carbon atoms in the molecule, said chlorine atom being joined to the glycide radical of the ether, then sulfonating said ether through replacement of the chloride radical with a sul-' fonate radical by reacting with a sulflte salt.
- Wetting and cleansing textile treating agents consisting of alkali metal salts of sulfuric acid derivatives of ethers of glycerine with fatty alcohols corresponding to the fatty acids contained in an 011 selected fromv the group consisting of cocoanut and palm kernel oils, the sulfuric acid radical being joined-to the glycerine radical.
- R represents an alkyl group containing one or more hydroxy groups one of which is etherifled with a hydroxy stearyl and where X is a member of the group consisting of an H atom and a cathion of a neutralizing agent.
Description
Patented Sept. 28, 1937 PATENT OFFICE.
WETTING-OUT-,
WASHING-,
CLEAN SING-9 LATHERING-, AND DISPERSING AGENTS Richard Hueter, Hans Waldfrieden, Rosslau/ alt, Germany,
assignor, by mesne assignments, to Unichem Chemikalien Handels A.-G., Zurich, Switzerland,a corporation of Switzerland No Drawing. ApplicationMarch 16, 1933, Serial 13 Claims.
The present invention has for an object the provision of improved wetting-out, washingcleansing-, foamingand dispersing agents. The wetting-out and emulsifying agents suitable for washing and cleansing purposes hitherto employed include sulphuric acid esters of the higher molecular fatty alcohols as well as higher molecular alkyl sulphonic acids in their original state or in the form of their neutralization products.
Compared with the aforesaid estcrlike sulphuric acid derivatives, it is true that the salts of the alkyl sulphonic acids distinguish themselves by extremely increased stability, but in the cold they are much less soluble so that their employment is limited to operations which can be carried out at higher temperatures, e. g., at temperatures of more thanabout 60 C. Moreover from experience to date, it appears that the feel, i. e.,
the softness and pliancy of the textiles treated with sulphonic acid salts is not as satisfactory as in the case when materials are treated with sulphnric acid ester.
Now it has been found that the alkyl ethers of the hydroxyalkylsulphonic acids formed with higher molecular alcohols, compared with the said alkylsulphonic acids, are of a better solubility in the cold, and besides possess good stability against acids, lime and magnesia salts. These com-.- pounds are therefore preferable for use for textile-chemical operations to be carried out at lower temperatures, e.'g., for the cleansing of wool and silk, for the dyeing of artificial silk and the like.
These new compounds are formed by the alkoxylation of mono-hydroxyor poly-hydroxyalkylsulphonic acids with higher molecular fatty alcohols, e. g., by the alkoxylation of hydroxyethane-sulfonic acid or di-hydroxypropanesulphonic acid.
In accordance with the preferred procedure one commences with glycide compounds such as, e. g., ethylene oxideor propylene oxide; one breaks down the ethylene oxide ring by alkoxylation and forms at the same time a hydroxyl group. The hydroxyl group after esteriflcation with halogen hydracid is in turn replaced by the sulphonic acid group. These transformations are based on the following reaction equations:
+HCl +NaiSOa In Germany March 18, 1932 to react with fatty alcohol mixtures in the presence of a small amount of sulphuric acid and with the aid of an autoclave and a slight excess of sodium sulphite, converting the reaction mixture obtained from the higher boiling components by washing with water and by fractional distillation in vacuo into sulfonic acid derivatives. Alkylchlorethylethers more difiicult to prepare may be converted in the same manner with sodium sulalcohols are dodecyl-, myristyland cetyl alcohol and the alcohol mixtures obtained by high pressure reduction from natural greases such as cocoa fat and palm kernel oil. Unsaturated alcohols such as oleyl alcohol and its homologues are, however, likewise to be taken into consideration. Polyhydroxy saturated or unsaturated alcohols may also be used, such as hydroxystearyl alcohol or ricinoleyl alcohol (dihydroxyoctadecene) obtained by reducing castor oil according to the reduction method of Bouvealt and Blane.
The new products, in the form of the alkaline salts, comprise crystalline masses of excellent capillary active properties. In the following a description is given for a particular method for the manufacture of such a product and a manner in which it may be used, it being understood, however, that the scope of the invention is not limited to the therein described manner of performance or the'proportional quantities.
Ezrampla-ZSO parts by weight of a fatty alcohol mixture (first runnings of the fatty alcohol mixtures obtained by catalytic reduction of cocoafat and distilling up to 130 C. at 3 mm. pressure of mercury) are heated for 16 hours to 115-120 C. in an open vessel together with 150 parts by weight of epichlorhydrine and 6 parts by weight of concentrated sulphuric acid. The reaction mixture is freed from sulphuric acid by boiling with water and is purified from by-products by fractional distillation. The main fraction boiling between 150 and 195 C. at 12 mm. pressure of mercury contains 13.2% of chlorine and is re- There is still a simpler way of obtaining the OINB acted at C. in well-known manner with the a calculated amount ofsodlum sulphite in a concentrated aqueous solution. The thus obtained reaction product is clearly soluble even in hard water at to C. and it develops a stable lather.
When the product obtained in accordance with the procedure of the above example is used for wetting-out of makopearlyarn, the goods are brought into a bath containing 0.1% of this product. The wetting-out occurs immediately and the materials are readily penetrated by the subsequent treatment baths (bleachin8-, dyeing baths and the like).
For cleansing of woolen piece goods one employs a bath which contains about 1,5 g. of the aforementioned product per litre of water. If there are considerable quantities of free fatty acids in the wool, an admixture of ammonia or soda is recommended. Material which has been dryed with dye stuffs sensitive to alkali, can be treated in the same bath, if the latter has previously been rendered acid by an addition of formic acid. The indicated cleansing bath develops an excellent deterging effect and imparts a soft and pliant feel to the thus treated material.
For cleansing of raw wool one usefully employs a 0,2% bath with 0,1% cyclo-hexanol and 0,1% of the above mentioned high molecular ether of the lwdroxyalkylsulphonic acid. By this the material is perfectly degreased. The presence of lime soap in the wool does no harm in the present case, since it is likewise dispersed by the bath.
What I claim is:-
1. The method of producing a di-alkyl ether sulfonic acid salt which comprises preparing an ether from a glycide and a fatty alcohol having 8 or more carbon atoms in the molecule, and reacting a chloride of said ether in which the chlorine is attached to the glycide radical of said ether with sodium sulflte to produce a sodium salt of the sulfonated ether. 1
2. The method of producing a dialkyl ether sulfonic acid salt which comprises reacting'epichlorhydrine with a fatty alcohol having 8 or more carbon atoms in the molecule in the presence of sulfuric acid and converting the product with sodium sulflte to produce sulfonic compounds.
3. A wetting and cleansing textile treatment agent consisting of an ether having in its formula on one side of the etherial oxygen atom a fatty alkyl radical containing 8 or more carbon atoms and on the other side a radical of an hydroxy propane sulfonate salt, the cation of which is an alkaline metal imparting water solubility properties to the ether.
4. As wetting, washing, cleansing, latherlng and dispersing agents, the products of the formula rt-o-cnhcnon-cmsoix wherein R is an alkyl radical of at least 8 carbon atoms and X is hydrogen or an alkali metal.
5. A wetting and cleansing textile treating agent comprising the sulfonate of propane etherifled withan alcohol radical selected from the group consisting of fatty alcohol radicals of at least 8 carbon atoms and naph-.
acid derivativ'es of ethers comprising forming a chloride of an ether by a process which includes reacting a glycide with a fatty alcohol having at least 8 carbon atoms in the molecule, said chlorine atom being joined to the glycide radical of the ether, then sulfonating said ether through replacement of the chloride radical with a sul-' fonate radical by reacting with a sulflte salt.
8. Wetting and cleansing textile treating agents consisting of alkali metal salts of sulfuric acid derivatives of ethers of glycerine with fatty alcohols corresponding to the fatty acids contained in an 011 selected fromv the group consisting of cocoanut and palm kernel oils, the sulfuric acid radical being joined-to the glycerine radical.
9. An ether of an alkyl radical with dihydroxy propyl sulfonic acid in which the alkyl radical joins through an oxygen atom of one of said hydroxy groups and is derived from cocoanut oil by reduction of the fatty acids therein to the corresponding fatty alcohols.
10. Alkyl ethers of poly hydroxy alkyl sulfonic acids in which the alkyl radicals on the one hand have more than 8 carbon atoms and are derived from and correspond to the mixture' of fatty alcohols obtained by reduction of an oil selected from the group consisting of cocoanut and palm kernel oils and the poly hydroxy alkyl radicals on the other hand are derivable from and corresponding to the glycerine radical, the sulfuric acid radical being joined to the glycerine radical.
11. The process of producing alkyl ethers of poly hydroxy alkyl sulfonic acids which comprises reducing cocoanut oil to alcohols, reacting a mixture of such alcohols with epichlorhydrine in the presence of sulfuric acid and reacting the resulting product with sodium sulflte to produce the sulfonic acid.
12. The compound of the formula R-CHz-SOJX sistingof an H atom and a cathion of a neutralizing agent.
13. Thecompound of the formula R-CHz-SOzX I where R represents an alkyl group containing one or more hydroxy groups one of which is etherifled with a hydroxy stearyl and where X is a member of the group consisting of an H atom and a cathion of a neutralizing agent.
RICHARD HUE'IER.
CERTIFICATE OF CORRECTION. Patent No. '2',0 9L .,h89. September 28, 1957.
' RICHARD HUETER.
It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows: Page 2, first column, line 19-, for "dryed" reeddy'ed; andsecomd column, line 62, claim 13, after stearyl" insert alcohol; and that the said LetterePatent should be read with these corrections therein thatv the same may conform to the record of the case in the. Potent Office.
. Signed andeealed this 8th day of February, A. 19.19 8;
' Henry-Van Aredale,
' (-Se'al) I Acting Commissioner ofPatents.
Publications (1)
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US2094489A true US2094489A (en) | 1937-09-28 |
Family
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US2094489D Expired - Lifetime US2094489A (en) | Wetting-out |
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US (1) | US2094489A (en) |
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2427576A (en) * | 1945-02-22 | 1947-09-16 | Colgate Palmolive Peet Co | Ether sulphonates and their production |
US2569423A (en) * | 1951-09-25 | Process fob preparing phenoxtalktl | ||
DE1024958B (en) * | 1953-03-06 | 1958-02-27 | Sandoz Ag | Process for the production of wetting agents for aqueous alkalizing liquids |
US2970963A (en) * | 1958-04-23 | 1961-02-07 | Procter & Gamble | Opaque liquid detergent composition |
US2970964A (en) * | 1957-04-16 | 1961-02-07 | Procter & Gamble | Opaque liquid detergent composition |
US2979465A (en) * | 1958-12-23 | 1961-04-11 | Procter & Gamble | Cream shampoo |
US2988511A (en) * | 1955-03-31 | 1961-06-13 | Mills Victor | Nonsmearing detergent bar |
US2989547A (en) * | 1956-12-10 | 1961-06-20 | Procter & Gamble | Method for preparing detergent compositions |
US3024273A (en) * | 1957-05-14 | 1962-03-06 | Procter & Gamble | Alkyl glyceryl ether sulfonate mixtures and processes for preparing the same |
US3082249A (en) * | 1958-05-13 | 1963-03-19 | Monsanto Chemicals | Sodium 3-tridecyloxy-2-propanol-1-sulfonate |
US3102893A (en) * | 1959-09-30 | 1963-09-03 | Monsanto Chemicals | Polyether-substituted glycidyl ethers |
US3190906A (en) * | 1960-09-07 | 1965-06-22 | Basf Ag | Alkane sulfonic acid esters substituted in beta-position by ether groups and their production |
US3228979A (en) * | 1959-09-30 | 1966-01-11 | Monsanto Co | Hydroxypropane sulfonates |
US3275682A (en) * | 1962-05-29 | 1966-09-27 | Shell Oil Co | Production of surface-active ether sulfonates |
US4520155A (en) * | 1984-04-23 | 1985-05-28 | The Lubrizol Corporation | Dye-receptive polyolefins and polyolefin fibers |
US5417892A (en) * | 1994-06-28 | 1995-05-23 | Colgate-Palmolive Company | Isethionate ether surfactant |
US20100041814A1 (en) * | 2008-08-15 | 2010-02-18 | Cvc Specialty Chemicals, Inc | Methods for preparing toughened epoxy polymer composite systems |
-
0
- US US2094489D patent/US2094489A/en not_active Expired - Lifetime
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2569423A (en) * | 1951-09-25 | Process fob preparing phenoxtalktl | ||
US2427576A (en) * | 1945-02-22 | 1947-09-16 | Colgate Palmolive Peet Co | Ether sulphonates and their production |
DE1024958B (en) * | 1953-03-06 | 1958-02-27 | Sandoz Ag | Process for the production of wetting agents for aqueous alkalizing liquids |
US2925316A (en) * | 1953-03-06 | 1960-02-16 | Saul & Co | Wetting agents for aqueous alkalizing liquids |
US2988511A (en) * | 1955-03-31 | 1961-06-13 | Mills Victor | Nonsmearing detergent bar |
US2989547A (en) * | 1956-12-10 | 1961-06-20 | Procter & Gamble | Method for preparing detergent compositions |
US2970964A (en) * | 1957-04-16 | 1961-02-07 | Procter & Gamble | Opaque liquid detergent composition |
US3024273A (en) * | 1957-05-14 | 1962-03-06 | Procter & Gamble | Alkyl glyceryl ether sulfonate mixtures and processes for preparing the same |
US2970963A (en) * | 1958-04-23 | 1961-02-07 | Procter & Gamble | Opaque liquid detergent composition |
US3082249A (en) * | 1958-05-13 | 1963-03-19 | Monsanto Chemicals | Sodium 3-tridecyloxy-2-propanol-1-sulfonate |
US2979465A (en) * | 1958-12-23 | 1961-04-11 | Procter & Gamble | Cream shampoo |
US3102893A (en) * | 1959-09-30 | 1963-09-03 | Monsanto Chemicals | Polyether-substituted glycidyl ethers |
US3228979A (en) * | 1959-09-30 | 1966-01-11 | Monsanto Co | Hydroxypropane sulfonates |
US3190906A (en) * | 1960-09-07 | 1965-06-22 | Basf Ag | Alkane sulfonic acid esters substituted in beta-position by ether groups and their production |
US3275682A (en) * | 1962-05-29 | 1966-09-27 | Shell Oil Co | Production of surface-active ether sulfonates |
US4520155A (en) * | 1984-04-23 | 1985-05-28 | The Lubrizol Corporation | Dye-receptive polyolefins and polyolefin fibers |
US5417892A (en) * | 1994-06-28 | 1995-05-23 | Colgate-Palmolive Company | Isethionate ether surfactant |
US20100041814A1 (en) * | 2008-08-15 | 2010-02-18 | Cvc Specialty Chemicals, Inc | Methods for preparing toughened epoxy polymer composite systems |
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