US2271635A - Dry cleaning composition and method - Google Patents

Dry cleaning composition and method Download PDF

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US2271635A
US2271635A US4216435A US2271635A US 2271635 A US2271635 A US 2271635A US 4216435 A US4216435 A US 4216435A US 2271635 A US2271635 A US 2271635A
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dry cleaning
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Lawrence H Flett
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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06LDRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L1/00Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
    • D06L1/02Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents
    • D06L1/04Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents combined with specific additives

Description

Patented Feb. 3, 1942 DRY CLEANING COMPOSITION METHOD AND Lawrence H. Flett, Hamburg, N. Y., assignor to AlliedCliemical & Dye Corporation, a corporation oi. New York I No Drawing.

14 Claims.

This invention relates to improvements in dry cleaning of textile and related materials. It relates particularly to improved compositionsior use in dry cleaning and to processes of dry cleaning in which said improved compositions are employed.

I have found, according to the present invention, that salts of aromatic sulfonic acid compounds which contain at least one alkyl group with 3 or more carbon atoms constitute valuable ingredients for dry cleaning compositions.

The said alkyl group or groups may be directly linked to the nucleus of the aromatic sulfonic acid compounds or may be joined thereto by means of an atom or radical, as fomexample, an

oxygen atom, or one of the radicals NH-,

NHCO, CO, etc. They may be alkyl hydrocarbon radicals or may contain substituents such as halogen, aryl, alkoxy, etc. Compounds in which the radical COOX (in which X represent hydrogen or a salt forming cation) is present as a substituent in the alkyl group are not included in the present invention in view of their inferior properties.

The aromatic nuclei of said sulfonlc acid compounds may be mononuclear, as for example phenyl, tolyl, etc., or pol'ynuclear, as for example naphthyl, diphenyl, etc. They may be free from further substituents or they may contain one or more substituents, as for example, OH, alkyl, alkoxy, and/or carboxyl (in the free acid or salt form).

The said sulfonic acids correspond with the formula:

where A is a mono or polynuclear aromatic res-' idue; R is a saturated or unsaturated substituted or unsubstituted alkyl group which contains at least three carbon atoms and in which the substituents, if any, may be alkoxy, ar'yl, halogen, etc.; X is either a bond joining a carbon atom of the alkyl group represented by R to a carbon atom of the aromatic nucleus. or is a linking atom or group of atoms, e. 'g., --O---, NH---, NHCO, CO, etc.; and y and z are integers, a being preferably 1.

This invention includes the use of various salts of the said sulfonic acids in which the hydrogen of the sulfo or other acidic groups is replaced by,an inorganic or organic salt-forming radical. Among the more easily procured salts are the ammonium, alkali-metal, alkaline earth Application September 25, 1935, Serial No. 42,164

metal salts and the salts in which the acidic groups are neutralized by the more common or- 'ganic bases, such as mono-, di-, or triethanolamine, pyridine, ethylene diamine, amylamines, triethylene tetramine, etc. If the salt-forming basic component is poly basic,

be of a detergent nature.

A preferred class of compounds comprises the mono-nuclear aromatic sulfonic acid compounds containing at least'one alkyl group with a minimum of 8 carbon atoms, or at least two alkyl groups containing at least 3 but less than 8 carbon atoms. Preferably the alkyl groups are directly linked to the aromatic nucleus and are free from substituents, and more particularly are saturated hydrocarbon radicals; and preferably the aromatic nucleus contains one or more hydroxyl groups as substituents. Among the'preferred alkylated aryl sulionates with an alkyl group of 8 or more carbon atoms, those with one such alkyl group are more efiective than com- The compounds which contain an alkyl group of 12 or more carbon atoms are moreefiective than compounds with several alkyl groups. The .compounds which contain an alkyl groupflof lii or more carbon atoms are more effective vthan those with the alkyl groups of lowercarbon content.

The following arespeciflc'ariomatic' sul'ionic acid compounds illustrative of those which may .be employed in accordance withthe presentinvention: sodium tetradecylphenonesulfonate, diisopropyl naphthalene sodium sulionate, sodium secon'dary-hexyl phenol sulfonate, sodium capryl hydroxy diphenyl sulfonate, sodium tetradecyl phenetole sulfonate, sodium tetradecyl cresol sulfonate, sodium tetradecyl naphthalene sulfonate, sodium lauryl phthalate sulfonate, sodium stearic toluidide sulfonate, and sodium para-cymene sulfonate. It will be understood, however, from the disclosure herein that the invention is not limited thereto.

The said salts ofaromatic sulfonic acid compounds, and particularly their alkali metal and organic ammonium salts, are soluble in volatile organic liquids of the type generally employed in dry cleaning (e. g. cleaning naphtha, carbon tetrachloride, trichlorethylene, etc.) in which they exert a desirable detergent action. The said salts of aromatic sulfonic acid compounds further have the valuable property of forming emulsions of water in the said organic liquids, and hence may be employed for the production of dryit may be neutral- 'ized in part with the above defined sulfonic acids and in part by other acidic materials which may cleaning compositions in the form of emulsions containing the organic dry cleaning liquid in the external phase and water in the internal phase.

One of the outstanding characteristics of the new dry-cleaning compositions of this invention is their ability to achieve excellent cleaning action in low concentrations. The said dry cleaning compositions are characterized in that the weight ratio of sulfonic acid salt to organic, substantially water-immiscible solvent or solvent mixture, is not greater than 1.0 to 100, and preferably less than 0.3 to 100. Improved finish and/or feel of the cleaned fabric, e. g., silks, can often be obtained by incorporating ,a small amount of paraflln wax or similar agent in the cleaning compositions.

Further, alkyl phenol sulfonic acid compoundsv which correspond with the general formula in which A represents hydrogen or a methyl group, R represents a nuclear alkyl hydrocarbon radical (saturated or unsaturated) containing 12 or more (especially 14 to 19) carbon atoms, and M represents hydrogen or a metal, such as an alkali metal, or an ammonium or an organic ammonium radical, constitute a preferred class of ingredients for dry cleaning compositions. Dry cleaning fluids in which the said .alkyl phenol sulfonic acid compounds and water are present serve not only to remove oil soluble soil from the material to be cleansed but have the additional advantage, in view of the superior detergent action of the said alkyl phenol sulfonic acid compounds in water, of also removing water soluble soil and spots. Inasmuch as the water solutions of the said compounds in the form of their alkali metal salts are neutral in reaction, dry cleaning compositions containing water and said compounds may be safely used for the cleaning of delicate silks and other fine fabrics.

The said alkyl phenol sulfonic acid compounds are derivatives of phenol (hydroxy benzene) and.

of the cresols (1.2-, 1.3-, and 1.4- methyl-hydroxy-benzene) in which the alkyl hydrocarbon radical represented by R. in the foregoing formula is directly linked to a nuclear carbon atom and in which the sulfonate group (represented by SO3M in the foregoing formula) is also directly linked to a nuclear carbon atom. For convenience they will be'hereinafter referred to as "alkyl phenol sulfonates which term generically includes th phenol and cresol derivatives, whether in the form of the free sulfonic acids or their salts. The alkyl phenol sulfonates preferably employed in accordance with the pres ent invention are those in which the alkyl group contains a branched carbon chain, whether linked to the benzene nucleus by an end carbon atom (an alpha carbon atom) or an intermediate carbon atom (that is, whether a primary, secondary or tertiary alkyl group).

The following examples illustrate several methods of preparing alkyl phenol sulfonates useful in connection with the present invention. It will be evident from a consideration of the disclosure herein that the invention is not limited to the use of products prepared in this manner but includes products of the type referred to herein prepared in other ways. The parts are by weight and temperatures are in degrees centigrade.

Example 1.-T- parts of commercial cetyl alcohol (containing 30 to 40 per cent of normal cetyl alcohol, 30 to 40 per cent of higher alcohols than cetyl, e. g. stearyl alcohol, etc., about 10 per cent of normal lauryl alcohol and about 20 per cent of normal myristyl alcohol), 100 parts of phenol, and 100 parts of anhydrous zinc chloride are heated at to 180, under a reflux condenser, with agitation for 16 hours. The condensation product is washed with water until practically free from water soluble products. The resulting oil is fractionally distilled in vacuo. The fraction of the. distillate which is collected between 195 and 240 at 15 mm. pressure of mercury is a faint yellow to water-white oil consisting chiefly of a mixture of alkyl phenols having the probable general formula:

in which Rm is a straight chain hydrocarbon radical having the formula:

C10H21, C12H2s, C14H29 or CisHas the compound in which Rm is C14H29 being a predominating compound, with a small amount of normal alkyl phenols and probably some ortho isomers present.

100 parts of the resulting purified alkyl phenol mixture, 40 parts of acetic anhydride and 106 parts of sulfuric acid mono-hydrate are mixed together and warmed gently to 70 to 75 until the product is completely soluble in water and a neutral 0.2 per cent solution does not recipitate calcium salts from a calicum chloride or other soluble calcium salt solution containing the equivalent of 0.224 gram calcium oxide per liter. The mass is diluted with water to a final volume of 450 to 600 parts and neutralized with alkali, as for example, caustic soda or caustic potash or their equivalents. The neutral solution is clarified, if desired, by filtration, and evaporated to dryness. The product is a brown to white solid, soluble in water to give brown to water-white solutions. It comprises a mixture of inorganic salts (e. g. sodium sulfate), with sulfonates of the said alkyl phenols (e. g., in the form of the sodium salts), of which mixture the inorganic salts constitute in the neighborhood of 60 per cent. The alkyl phenol sulfonates present are soluble in alcohol, benzene and other organic solvents.

Example 2.-A mixture of 185 parts of lauryl chloride (prepared from commercial lauryl alcohol), 100 parts of phenol and 30 parts of zinc chloride (as a condensing agent) are heated with agitation at a temperature of to under a reflux condenser for 20 hours. The reaction mixture is allowed to.cool and the resulting oil which separates is decanted oil and fractionally distilled in a vacuum. The fraction of the distillate boiling between 150 and 230 at 4 mm. pressure of mercury is separately collected. It consists chiefly of lauryl phenol.

To 20 parts of the lauryl phenol thus obtained, there is slowly added, with agitation, 20 parts of sulfuric acid mono-hydrate, and the mixture is maintained at a temperature of 30 to 35 for 3 hours, or until the desired sulfonati on is effected. The mass is then diluted with 400 parts of water, and the solution thus obtained is neutralized at approximately 250 SOsNa Example 3.700 parts of an olefine with a boiling point ranging from 237 to 262 and having an average carbon content of 14 to 15 carbon atoms (and obtained by dechlorination of the monochlor hydrocarbons separated by fractionation from the products resulting from chlorination of petroleum distillates which boil at atmospheric pressure), 700 parts of phenol, and 350 parts of anhydrous zinc chloride are mixed and heated together while agitated under a reflux condenser at a temperature around 180 to 190 for from to 16 hours. The condensed mass is diluted and washed with water until reasonably free of water-soluble impurities,. and the crude brownish oil is distilled in vacuo. The fraction of the distillate boiling between 195 and 240 at mm. pressure is collected separately. It is a faintly .colored to water-white oil, insoluble in water and dilute caustic soda.

100 parts by weight of the resulting 011 are mixed with 148 parts by weight of sulfuric acid monohydrate at then heated to '70-75 and held there until a sample is completely soluble in water and in neutral, acid or alkaline aqueous solutions, and a neutral 0.2 per cent solution does not precipitate calcium salts from a soluble calcium salt solution containing the equivalent of 0.224 gram calcium oxide per liter. The sulfonation mix is poured into water, diluted to a final volume of 450 to 600 parts, and made neutral (for example, to delta paper, Congo red paper, brilliant yellow, or brom-phenol-blue) with alkali, for example caustic soda, or potash or their equivalents. The neutral solution is evaporated to dryness. If desired, the neutral solution can be clarified by filtration before being evaporated to dryness. V

The product thus obtained is a mixture of which the chief components are alkyl phenol sulfonates having the probable formula (SOr-NDp R. where R0 represents an aliphatic hydrocarbon group, M represents an alkali metal or equivalent derived from the base used for neutralization, and p is 1 or 2 but mainly'l. For the most part, the alkyl phenol sulfonates contain branched carbon chains in the groups represented by Re and these groups are connected to the phenol nucleus by primary, secondary or tertiary carbon atoms. The chief components of the mixture contain 14 or 15. carbon atoms in the alkyl group represented by R42.

In the form of the alkali metal and alkaline earth metal salts it is a faintly colored light brown to white, friable solid, readily reduced to produced by such processes as in alcohol and other organic solvents.

a comminuted or powdery form (resembling powdered soap) and readily soluble in water. The products of the above examples contai inorganic salts (e. g., alkali metal sulfates) in admixture with the alkyl phenol sulfonates. When it is desired to employ the alkyl phenol sulfonates in a form free from inorganic salts, they may be obtained from the mixed products are given in the above specific examples by taking advantage of the solubility of the alkyl phenol sulfonate salts Thus a mixture of a salt of the sulfonated product and an inorganic sulfate may be extracted with alcohol, and the resulting extract may be evaporated to leave a residue of the purified salt of the sulfonated product, as illustrated by the following specific example.

Example 4.--The neutralized solutions containing alkyl phenol sulfonates prepared in Examples 1, 2 and 3, or equivalent aqueous solutions prepared from the final dry sulfonates, are diluted with an equal volume of commercial denatured alcohol, thoroughly mixed for several hours, filtered and evaporated to dryness; or the dry sulfonates are extracted with successive portions of denatured alcohol, the total amount of alcohol used for this'ext'raction being preferably not more than approximately four times the weight of thedry unextracted sulfonate, the combined extracts are mixed and digested with a small amount of animal charcoal, filtered and evaporated to dryness. The residue obtained in either case is an alkyl phenol sulfonate in the salt (e. g., sodium salt) form, practically free from salts of mineral acids.

The following examples illustrate the use of the products hereinbefore described. It will be understood, however, that these examples are merely illustrative and that any of the other 'sulfonated products herein described may be similarly employed. The parts are by weight.

Example 5.-Botany worsted cloth (carbonized) is soiled by immersion in a carbon tetrachloride solution of tallow, and mineral oil containing lamp black in suspension, and the soiled cloth is dried. The resulting soiled cloth shows a brightness (whiteness) of 14.3 per cent by photometric test (Zeiss-Pulfrich photometer). 0.3 gram of the sodium lauryl phenol sulfonate prod uct of Example 2, containing about 0.15 gram of sodium lauryl phenol sulfonate and about 0.15 gram of inorganic salts (sodium sulfate) is mixed with cc. of cleaners naphtha. A 5 gram sample (6.3 inches square) of the above soiled Botany worsted cloth is placed in a pint jar containing the resulting solution together with 50 grams of glass beads of 3 mm. diameter and agitated at 50 for 30 minutes in a launderometer. The sample of cloth is then passed through a wringer and dried. The dried sample shows a brightness (whiteness) of. 24 per cent by photometric test (Zeiss-Pulfrich photometer). When a like sample of the soiled cloth is similarly cleaned in the absence of the lauryl phenol sulfonate, it shows a brightness (whiteness) .of 12.9 per cent; that is, the resulting sample appears more soiled than before cleaning.

Example 6.-0.25 gram of water is added to the cleansing mixture in above Example 5, and the resulting mixture is employed as in said example. The brightness (whiteness) of the cleaned sample is 30.3 per cent.

Example 7 .Trichlorethylene is substituted for the cleaners naphtha employed in Examples 5 and 6. The procedure is otherwise the same. The brightness (whiteness) of the cleaned sample without the water being present is 28.9 per cent and with the water present is 30.7 per cent.

Example 8.Carbon tetrachloride is substituted'for the cleaners naphtha employed in Examples 5 and 6. The procedure is otherwise the same. The brightness (whiteness) of the cleaned sample without the water being present is 27.7 per cent and with the water present is 29.2 per cent.

Example 9.A soiled Botany worsted cloth having a brightness (whiteness) of 9.4 per cent is prepared in accordance with theprocedure employed in Example 5. 0.15 gram oithe purified sodium cetyl phenol sulfonate obtained in accordancewith the procedure of Example 4 is employed for the cleaning of a 5 gram sample of this soiled cloth by the procedure of Example 5, with the exception that the cleanedsample is allowed to dry without being passed through a wringer. The brightness (whiteness) of the cleaned sample is 16.6 per cent. By carrying out the procedure of this example in the absence of the sodium cetyl phenol sulfonate, a cleaned sample is obtained having a brightness (whiteness) of 7.! per cent.

It will be realized by those skilled in the art that changes may be made in the compositions, and in the processes of preparing and using them, hereinbefore described, without departing from the scope of the invention.

The alkyl phenol sulfonates employed in accordance with the present invention may be prepared in various ways. According to one method of preparation, an alkyl phenol or cresol of the type (in which the symbols A and R have the meaning defined above) may be treated with a sul-v fonating agent, in the presence or absence of a solvent or diluent and/or a sulfonation assistant. As sulfonating agents there may be employed sulfuric acids of various strengths (e. g., 66 B. sulfuric acid, sulfuric acid monohydrate, oleum) chlorsulfonic acid, etc. As solvents or diluent there may be employed any inert organic liquid which is not readily sulfonated, such as halogenated hydrocarbons of the aliphatic and aromatic series, as for example, carbon tetrachloride, dichlorethane, tetrachlorethane, dichlorbenzene, etc. As sulfonation assistants there may be employed the lower organic acids and/or their anhydrides, as for example, acetic acid, acetic anhydride, etc.

The sulfonation may be carried out with the aid of heating or cooling, as required, depending upon the ease of sulfonation of the alkyl phenol or cresol and the sulfonating power of the sulfonating agents. The sulfonation of the alkyl phenol or cresol may be carried out to an extent such that mainly one, or more or less than one, sulfonic acid group is present in the final product (based on the alkyl phenol or cresol). In general the extent of sulfonation of the alkyl phenol or cresol treated is such as to form chiefly the mono-sulfonic acid of the alkyl phenol, and to sulfonate impurities as well, if present.

The alkyl phenol sulfonates may be employed in accordance with the present invention in the form of their free sulfonic acids or in the form of salts of metals (as for example, of the alkali metals) or of organic bases, or of ammonia, etc. The salts may be obtained in any suitable manner; for example by reacting the sulfonated product, either in the crude form resulting from the sulfonation or in a purified form, with a metal oxide or hydroxide, ammonia or an organic base, or of a suitable salt oi. one of these. in an amount adapted to form a neutral product. Among the bases. oxides and salts which may be combined with the sulfonated products to produce salts useful in accordance with the present invention are, for example, sodium, potassium and ammonium hydroxides; sodium, potassium and ammonium carbonates and bicarbonates; ammonia, magnesium oxide; ethylamine; pyridine; triethanolamine; propanolamines; butanolarnines; diamino propanol; ethylenediamine; triethylene tetramine; etc.

The sulfonated alkyl phenol products in the form of metallic salts or salts of inorganic bases are usually yellowish to'white, friable solids; and in the form of salts of organic bases vary from viscous oils to semi-solids to solids. In general, the salts are readily soluble in water and in aqueous (neutral, acid or alkaline) solutions to form solutions which are faintly colored brown oryellow, which are of a soapy nature and which foam readily. In general, they are less soluble in the dry cleaning solvents than in water but they are sumciently soluble to give solutions which are adequate for use for the dry cleaning of fabrics, yarns, etc. Certain of the salts, such as the salts of the aromatic monoamines and the aliphatic and aromatic polyamines, are oils which generally are insoluble in water, probably due in part to the presence of small amounts of organic impurities, but soluble in organic solvents (as for example, benzene, gasoline, etc.) and in aqueous solutions of alkalis (presumably by conversion to the salts of the alkalis) It is to be understood that the invention includes the use of products containing a plurality of alkyl phenol sulfonic acid nuclei linked together through the sulfonic acid groups by a polyvalent metal or organic basic radical, as well as products in which analkyl phenol sulfonic acid is linked through the sulfonic acid group to a diflerent acid compound by a polyvalent metal or organic basic radical.

Thus the invention comprehends compounds of the type (X) a-Z-(X'). and (x)-Z(Y)., wherein X and x' each represent the radical R Borwhich may be the same or different, Z represents a polyvalent metal or organic base, Y represents a radical containing an acid group, n represents a whole number, and A and R have the meaning defined above. Examples of such types of compounds are wherein X and R have the meaning defined above, and W represents a radical containing an linked by an oxygen atom to the aromatic nu-' cleus, may be rearranged to the alkyl phenol; or the alkyl group may be substituted in the aromatic nucleus in the form of a ketone by condensing phenol or a cresol with a fatty 'acid or acid chloride corresponding with the desired alkyl group, in place of an alkylating agent in the process just, enumerated, and subsequently reducing the resulting ketone.

In the condensation of phenol or a cresol with an alkylating agent there may be employed as alkylating agents non-aromatic alcohols (as for example, straight-chain, primary monohydric alcohols; straight-chain, secondary monohydric alcohols; branched-chain primary alcohols; branched-chain secondary alcohols; tertiary alcohols of all types; etc.), olefine hydrocarbons containing straightor branched-chains, and containing a double bond preferably between the ultimate and penultimate carbon atoms; and halogen derivatives of hydrocarbons; all containing at least 12 carbon atoms and preferably 12 to 23 carbon atoms in an alkyl hydrocarbon chain. A preferred alkylating agent is commercial lauryl alcohol containing a mixture of normal alcohols, including a major proportion of lauryl alcohol together with cetyl alcohol, myristyl alcohol, etc. As condensing agents there may be employed anhydrous zinc chloride, anhydrous aluminum chloride, anhydrous antimonic chloride, anhydrous ferric chloride, zinc, copper, etc.

It is to be noted that mixtures of two or more of the sulfonated products hereinbefore referred to may be employed.

For the purpose of illustration, the following additional products, in the form of the free sulfonic acids and in the salt (e. g., sodium salt) form, are mentioned as suitable for use in accordance with the present invention; but the invention is not limited thereto, as will be evident from the disclosure herein:

Cetyl phenol sulfonate (resulting from the condensation of cetyl alcohol with phenol and sulfonation of the resulting cetyl phenol) Alkyl metaor para-cresol sulfonates, or mixtures thereof, in which the alkyl groups correspond with the alcohols contained in commercial cetyl alcohol (and obtainable by condensing commercial cetyl alcohol with ortho-, metaor paracresol and sulfonating the resulting mixture of alkyl ortho-, metaor para-cresols);

Lauryl cresol sulfonates, 'or mixtures thereof with homologous alkyl phenol or cresol sulfonates (obtained by condensing cresol with a commercial mixture of lauryl alcohol and homologous fatty alcohols corresponding with the fatty acids of cocoanut oil, and sulfonating the resulting alkyl phenol or alkyl cresol mixture);

Octadecyl (stearyD- phenol sulfonate (l-methyl-heptadecyl phenol sulfonate) Normal primary hexadecyl phenol sulfonate (obtainable by reducing palmito- (hydroxy) benzophenone and sulfonating the resulting alkyl phenol) Pentadecyl phenol sulfonate (obtainable by condensing phenol with the pentadecyl alcohol resulting from the polymerization of amyl alcohol, and sulfonating the resulting alkyl phenol) Tricosyl phenol sulfonate (obtainable by condensing tricosanol-7 with phenol, followed by sulfonation);

Alpha-alpha-dimethyl-hexadecyl-phenol sulfonate (obtainable by condensing dimethyl pentadecyl carbinol with phenol and sulfonating the resulting alkyl phenol).

This application is a continuation-impart of my application Serial No. 691,082, filed September, 26, 1933.

I claim:

1. A dry cleaning composition comprising a solution in an organic liquid of the dry cleaning type of a salt of an aromatic sulfonic acid compound containing at least one alkyl group with at least 3 carbon atoms, and corresponding in the free acid form with the formula gen, X is a bond joining a carbon atom of the alkyl group R to a carbon atom of the aromatic nucleus A or is a linking atom or radical, and y and z are integers.

2. A dry cleaning composition comprising a solution in an organic liquid of the dry cleaning type of a salt of an aromatic sulfonic acid compound containing at least one alkyl hydrocarbon group with at least 8 carbon atoms.

3. A dry cleaning composition comprising an organic liquid of the dry cleaning type and a small amount of a dry cleaning assistant comprising an alkyl phenol sulfonate in which the alkyl radical consists of an alkyl hydrocarbon radical containing at least 12 carbon atoms.

4. A dry cleaning composition comprising an emulsion of water in a volatile organic liquid of the dry cleaning type, the water being in the internal phase, and a salt of an aromatic sulfonic acid compound containing at least 1 alkyl hydrocarbon group with at least 3 carbon atoms as an emulsifying agent for the water and as a dry cleaning assistant, said salt being selected from the group consisting of alkali metal, alkali earth metal, ammonium and organic ammonium salts.

5. A dry cleaning composition comprising an emulsion of water in a volatile organic liquid of the dry cleaning type, the water being in the internal phase, and a salt of an aromatic sulfonic acid compound containing at least 1 open chain alkyl hydrocarbon group with at least 12 carbon atoms as an emulsifying agent for the water and as a dry cleaning assistant, said salt being selected from the group consisting of alkali metal, alkali earth metal, ammonium and organic ammonium salts.

6. A dry cleaning composition comprising an emulsion of water in a.volatile organic liquid of the dry cleaning type, the water being in the internal phase and an alkyl phenol sulfonate in which the alkyl radical consists of. an alkyl hydrocarbon radical containing at least 12 carbon atoms as an emulsifying agent for the water and as a dry cleaning assistant.

7. A dry cleaning composition comprising an emulsion of water in a volatile organic liquid of the dry cleaning type, the water being in the internal phase, and a salt of an aromatic sulionic acid compound soluble in said mixture and containing at least 1 open chain alkyl hydrocarbon group with at least 12 carbon atoms as an emulsifying agent for the water and as a dry cleaning assistant.

8. A dry cleaning composition comprising an emulsion of water in a volatile organic liquid of the dry cleaning type, the water being in the internal phase, and a salt of a mononuclear aromatic sulfonic acid containing an alkyl hydrocarbon group with at least 12 carbon atoms directly linked to the aromatic nucleus as an emulsifying agent for the water and as a dry cleaning assistant, said salt being selected from the group consisting of alkali metal, alkali earth metal, ammonium and organic ammonium salts.

9. A dry cleaning composition comprising a volatile organic liquid of the dry cleaning type and not more than 1 per cent of the weight of the organic liquid of a soluble salt of an aromatic sulfonic acid compound containing at least one alkyl group with at least 8 carbon atoms, and corresponding with the formula wherein A is an aromatic residue,R is an alkyl group containing at least 8 carbon atoms, and which may be substituted by alkoxy, aryl or halogen, X is a bond joining a carbon atom of the alkyl group R to a carbon atom of the aromatic nucleus A or is a linking atom or radical, M is an alkali metal or an alkali earth metal or an am- -monium or organic ammonium radical, and y 11. A dry cleaning composition comprising a solution in a voltatile organic liquid of the dry cleaning type or a salt of a mononuclear aromatic sulionic acid containing an alkyl hydrocarbon group with at least 12 carbon atoms directly linked to the aromatic nucleus.

12. A dry cleaning composition comprising a volatile organic liquid of the dry cleaningtype and a dry cleaning assistant which is a salt of a mononuclear aromatic suli'onic acid containing an alkyl hydrocarbon group with at least 12 carbon atoms directly linked to the aromatic nucleus in an amount not exceeding 1 per cent by weight or said liquid, said salt being selected from the group consisting of alkali metal, alkali eglrth metal, ammonium and organic ammonium s ts.

13. A dry cleaning composition comprising an emulsion of water in a volatile organic liquid of the dry cleaning type, the water being in the internal phase, and a salt of a mononuclear aromatic suli'onic acid soluble in said mixture and containing an alkyl hydrocarbon group with at least 12 carbon atoms as an emulsifying agent for the water and as a dry cleaning assistant.

14. A dry cleaning composition comprising an emulsion of water in a volatile organic liquid of the dry cleaning type, the water being in the internal phase, and a salt of an aromatic sulfonic acid compound containing at least one alkyl group with at least 3 carbon atoms, and corresponding inthe free acid form with the formula as an emulsifying agent for the water and as a dry cleaning assistant, wherein A is an aromatic residue, R is an alkyl group containing at least3 carbon atoms and which may be substituted by alkoxy, aryl or halogen, X is a bond joining a carbon atom of the alkyl group R to a carbon atom of the aromatic nucleus A or is a linking atom or radical, and 11 and z are integers.

LAWRENCE H. FLETT.

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US3272754A (en) * 1961-08-08 1966-09-13 Sandoz Ltd Dry cleaning agents for textile materials
US3310498A (en) * 1963-07-26 1967-03-21 Stamford Chemical Ind Inc Novel detergent compositions
US3310499A (en) * 1963-07-26 1967-03-21 Stamford Chemical Ind Inc Novel detergent compositions
US3503888A (en) * 1965-02-16 1970-03-31 Dow Chemical Co Synthetic detergent bar
US3978010A (en) * 1973-12-20 1976-08-31 Shell Oil Company Aqueous windshield cleaner formulation comprising amine salts, methanol and boric acid
US3988264A (en) * 1973-12-20 1976-10-26 Shell Oil Company Windshield cleaner formulation
US4088680A (en) * 1975-02-03 1978-05-09 Chevron Research Company Linear alkyl hydrocarbyloxybenzene disulfonates
US4104023A (en) * 1970-12-11 1978-08-01 Chevron Research Company Ring polysulfonated alkylphenoxy alkylols as detergents
US5973195A (en) * 1998-03-19 1999-10-26 Energy Biosystems Corporation Surfactants derived from 2-(2-hydroxyphenyl)benzenesulfinate and alkyl-substituted derivatives
WO2000042005A1 (en) * 1999-01-14 2000-07-20 Energy Biosystems Corporation Compositions comprising 2-(2-hydroxyphenyl) benzenesulfinate and alkyl-substituted derivatives thereof

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2899460A (en) * 1959-08-11 Purification of alkaryl sulfonic acids
US2450505A (en) * 1946-05-31 1948-10-05 Ohio Commw Eng Co Dry-cleaning emulsion
US2564926A (en) * 1948-06-21 1951-08-21 Great Lakes Carbon Corp Agents for rendering cleaners' solvents electrically conductive
US3101239A (en) * 1953-10-07 1963-08-20 R R Street & Co Inc Dry cleaning
US2736632A (en) * 1954-02-09 1956-02-28 Blau Mfg Company Inc M Dry cleaning process
DE976012C (en) * 1955-02-12 1963-01-10 Hoechst Ag Method of chemically cleaning fibrous material
US2980624A (en) * 1957-01-04 1961-04-18 Gen Aniline & Film Corp Dry cleaning compositions
US3018251A (en) * 1957-01-11 1962-01-23 Gen Aniline & Film Corp Dry cleaning compositions
US3057676A (en) * 1957-04-27 1962-10-09 Bohme Fettchemie Gmbh Dry-cleaning composition and process
US2992999A (en) * 1958-06-23 1961-07-18 Dow Chemical Co Dry cleaning solvent containing haloalkyldiphenyl oxide sulfonates
US3110683A (en) * 1959-09-28 1963-11-12 Dow Chemical Co Process of inhibiting corrosion
US3272754A (en) * 1961-08-08 1966-09-13 Sandoz Ltd Dry cleaning agents for textile materials
US3310498A (en) * 1963-07-26 1967-03-21 Stamford Chemical Ind Inc Novel detergent compositions
US3310499A (en) * 1963-07-26 1967-03-21 Stamford Chemical Ind Inc Novel detergent compositions
US3503888A (en) * 1965-02-16 1970-03-31 Dow Chemical Co Synthetic detergent bar
US4104023A (en) * 1970-12-11 1978-08-01 Chevron Research Company Ring polysulfonated alkylphenoxy alkylols as detergents
US3978010A (en) * 1973-12-20 1976-08-31 Shell Oil Company Aqueous windshield cleaner formulation comprising amine salts, methanol and boric acid
US3988264A (en) * 1973-12-20 1976-10-26 Shell Oil Company Windshield cleaner formulation
US4088680A (en) * 1975-02-03 1978-05-09 Chevron Research Company Linear alkyl hydrocarbyloxybenzene disulfonates
US5973195A (en) * 1998-03-19 1999-10-26 Energy Biosystems Corporation Surfactants derived from 2-(2-hydroxyphenyl)benzenesulfinate and alkyl-substituted derivatives
WO2000042005A1 (en) * 1999-01-14 2000-07-20 Energy Biosystems Corporation Compositions comprising 2-(2-hydroxyphenyl) benzenesulfinate and alkyl-substituted derivatives thereof
US6303562B1 (en) 1999-01-14 2001-10-16 Enchira Biotechnology Corporation Compositions comprising 2-(2-hydroxyphenyl)benzenesulfinate and alkyl-substituted derivatives thereof

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