JPH05501406A - Novel thiodiglycol derivative, its production method and its use as a textile softener - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

[Detailed description of the invention] A novel thiodiglycol derivative, its production method and its use as a textile softener Purpose In the field of textile fabric softeners for household and commercial use, quaternary ammonium compounds substances, particularly dimethyldistearylammonium chloride, have hitherto been actually very were important [Vogel, P. and Kluysman, P. (H, K rllssmann), Seiffen, Age, Fetch, Vaxe ( Se: fen, ○Ie, Fette, Wachse), Volume 111, 567 ~574 pages, 1985, and L, G oderro y) and Bar Bain (H, He1n), Seiffen, Age, Fetch, V Access, Vol. 115, pp. 3-8, 1989].

Attention should be paid to the shelf life and viscosity of concentrated textile softeners as well as their biodegradability. In place of such ingredients, nitrogen-free alternative compounds or corresponding There are many proposals in the literature using such systems. Such proposals are based on inorganic and Particularly inorganic insoluble components, e.g. layered/licade compounds (e.g. West German Patent No. 23) 34899) and selected organic components, such as long-chain α-sulfo fatty acids. and combinations of such systems (West German Patent No. 3604039) (see No.) is also included.

The present invention describes an unknown nitrogen-free organic compound that can be used in textile softening. It is particularly suitable for use, e.g. in known rinse cycle softening, in contrast to conventional It may be sufficient as a substitute for textile fabric softeners containing quaternary ammonium compounds. However, if properly selected and used, it can be processed to provide a feel that exceeds conventional industrial possibilities. It also relates to compounds that can be added to textile products.

Therefore, in a first aspect, the present invention provides general formula (1) [wherein Xl and/or or X is a β-hydroxyl-substituted alkyl group having 8 to 30 carbon atoms; / or represents an alkyl monocarboxylic acid group having 8 to 30 carbon atoms, l and X may be the same or different, and monoethers and monoesters In the case of , X or X is hydrogen and Z is a number of 1 or 2. ] Novel thiosyglycol sulfoxide and/or sulfone shown in mo/- and/or bis-ether and mo/- and/or bis-ester Regarding ru.

The thiodiglycol compound represented by the general formula (+) of the present invention is an unknown type of compound. It is a thing. Such compounds contain thiodiglycol and 8 to 30 carbon atoms in the molecule. by reaction with α-olefin epoxide compounds having elementary atoms or For the corresponding reaction of diglycol with an alkyl monocarboxylic acid of similar carbon chain length: Therefore, synthesize.

The molar ratio of thione glycol and α-olefin epoxide compound used (1, 1 to 1:2), β-hydroxy to Xl and/or X by ring opening. By forming a sialkyl group, the corresponding moiety represented by general formula (1) and/or produce bis-ethers. In contrast, British Patent No. 109739 Another method for obtaining bis-ether derivatives of thiodiglycol described in No. 6 Then, the starting compounds used are divinyl sulfone and alcohol, and the corresponding In bis-[2-alfky/ethylyosulfone, the β-hydroxy No sialkyl groups are formed.

In a preferred embodiment of the invention, at least 0.05 A conventional basicity in an amount of from 5% to about 5% by weight, preferably from about 0.1% to 1% by weight. In the presence of catalysts such as alkali hydroxides and/or alkali methoxylates and thiodiglycol and CS-S. α-olefin compound and the required specific mole React at a ratio of (1 to 1.2).

The actual reaction is carried out at a temperature of less than 120° C. to about 200° C., preferably about 1 At a temperature of 60-170'C for about 3-6 hours, the epoxide oxygen content was reduced to 0.5 %, preferably less than 0.2%. The epoxide oxygen content is determined by the continuous It is used for quantitative monitoring and ultimately for measuring the quantitative progress of a reaction. .

Reaction of thiodiglycol with alkyl monocarboxylic acids or their reactive derivatives According to the molar ratio of thiodiglycol and alkyl monocarboxylic acid used (1, 1 to 1 and 2), the general formula ( The corresponding compounds indicated by +) are obtained. Similar reactions are described in Russian literature [V, A, T rofimoν), I.F.Gur/Yuko (I,N.Gurshko) and V.I.I.S.A. Gulyants (V, I, I sagulyants), Zanar Priklatno Lee Kimi (ZhP rikl, K him), Volume 48, 626-62 8, 19753゜According to this document, thiodiglycol in the presence of pyridine was reacted with acid chloride in benzene, followed by cumylhydrochloride in n-hebutane. - oxidation with a sulfoxide to form a sulfoxide. Conversion to bis-ester of diglycol.

The resulting thiodiglycol mono- and/or bis-ether or mono- and/or the bis-ester type reaction products are then oxidized by known methods. for example, 30-70%, preferably 70% of an amount in glacial acetic acid. carried out using hydrogen peroxide to form a sulfoxide (2=1 in general formula (1)), and/or using 2 times the volume of 70% hydrogen peroxide in glacial acetic acid. to form sulfone (x-2 in general formula (I)).

Comparatively wide range of new thiodiglycol derivatives of the present invention represented by general formula (1) However, the narrower subclass selected is for textile softeners as contemplated by the present invention. It is characterized by being particularly suitable for applications. Therefore, the original According to Akira, the substituents X1 and X have 12 to 24 carbon atoms, especially carbon atoms. derived from a β-hydroxy-substituted alkyl group or anlu group having about 12 to 18 molecules; It is preferable that Preferred groups of this type for X and X are the corresponding linear It is the basis.

Different groups of the aforementioned types are present in XI and X, i.e. according to the invention A group characterized by the presence in a particular molecule of a mixed group of the type defined. Compounds of general formula (1) are included within the scope of the present invention. structurally identical, and Optionally, structurally different groups can be present in xl and X. But get Structurally identical groups are preferred, or mixed groups X1 and X! In the case of compounds having It may have a group of increasing or decreasing properties.

homogeneous radicals, especially similar or identical radicals of the above-mentioned type, to xl and The thiodiglycol derivative of general formula (1) having Particularly preferred for use. However, also in this embodiment, mixed substituents X, and Also in the above embodiment of the compound having X, the present invention provides a compound represented by the general formula (1) Encompasses mixtures of different compounds. Use of such ingredients for softening textile products As will be described in detail later in connection with the process, X and X are relatively long chains, Compounds represented by (1) and corresponding structures in which Xl and X are shorter chains, especially structures In particular, it is preferred to use certain selected mixtures with components of general formula (I) that are identical in terms of It can be advantageous. The reason is that the industrially important properties for textile softening are This is because it can be influenced by the properties of the particular groups XI and X. Therefore, there is One component optimized for desired performance, selected and synthesized separately for performance. Can compound a be used in accordance with the invention in combination with other ingredients? It is Noh.

The above knowledge regarding substituents X1 and X2 in the compound represented by general formula (1) is Possible combinations of parameters Z, i.e. sulfoxide type or sulfone type The same applies to the selection of compounds. Particularly important in practice is the sulfone (z = 2 ), which is the case with this type of compound, as a general rule in the case of sulfoxide compounds. This is because they are not damaged by disproportionation reactions that may occur. The disproportionality As a result of the reaction, in addition to sulfone, which has no particular odor, sulfide, which has a bad odor, can be produced. Ru. However, in principle, both the sulfones and sulfoxides of the present invention have their softening properties. It can be flavored with standard fragrances without substantially impairing its properties. On the other hand, before The following sulfoxide compounds may be used alone or with sulfones for the purpose of the present invention. It may be accompanied by the advantageous ability to be used in combination.

In its most important aspect, the present invention provides a thiodiglycol represented by general formula (1). compound, alone or with solvents, emulsifiers and/or dispersants or stabilizers. Textile softening mixtures containing in combination. Represented by general formula (1) Such auxiliaries used in addition to the compounds may, if desired, themselves have detergent properties. and/or may have a detergency-enhancing effect.

The various possibilities of the invention are explained in the examples below, or examples of the invention are explained below. The teachings relate to some aspects of the core of the embodiments described herein. ratio Relatively short chain, e.g. 12 carbon atoms, β-hydroxyl substituted linear alkyl group Compounds of general formula (I) of bis-ether type having a final rinse softening When applied from the aqueous auxiliary phase, the sulfone compound form and the sulfoxide Both in the form of the compound, in sensory terms, exceed the standards currently achieved at home. It shows superior softening effect.

When using corresponding compounds with a higher number of carbon atoms in the chain of Xl and X, , the situation will be different. Corresponding β-hydroxyl substituted C+g derivatives or is the corresponding C1. When derivatives are used in the absence of auxiliaries, treated textile products This is because no significant softening effect can be obtained. However, when used as a fabric softener, The components of general formula (1) include dispersion or emulsification aids (e.g. anionic and/or are of the nonionic surfactant type), and/or emulsifiers (e.g. glycerol). (of the glycerol partial ether or glycerol partial ester type) For example, it is important to fully express the softening effect of textile products in the final rinsing process. The effect obtained by the corresponding shorter-chain derivative represented by general formula (1) was clarified. It can even surpass crabs. Therefore, in the above cases, dispersants or emulsifiers and/or The presence of stabilizers or stabilizers has a significant enhancing effect on the softening effect. in contrast, Xl and When used together with similar auxiliaries, the performance level for textile softening is significantly improved. It can decrease. Therefore, in this case, for the purpose of optimizing the desired result, It is desirable not to use such additional additives. From this purely illustrative explanation , a person skilled in the art can conduct simple preliminary tests to find a suitable or optimal mixture for a particular intended application. Therefore, it can be determined and prepared.

Basically the same, but the length of the carbon chain in the substituent Xl and/or X is different. Since the components exhibit different behavior as described above, Xl and/or , with a corresponding selected component having a relatively short carbon chain length of xl and/or The method according to the invention can also be achieved by combining with corresponding components with longer carbon chain lengths. It is possible to achieve certain optimizations. This can be used to soften textile products. Regarding the rewetting properties of The compound represented by the general formula (I) having a C1 alkyl group substituted with When used as a fabric softener, it has significant values for the rewetting properties of softened textiles. Characterized by showing.

Xl and/or X, the number of carbon atoms of the corresponding substituent is 16 and/or As one moves towards relatively long chains, rewetability decreases or sensory In terms of properties, there are significant improvements, especially when combined with surfactants as auxiliaries. Can lead to good. Therefore, both types are used in the textile softener of the present invention. By combining, pre-IC! Two effects: improved rewetting Both can be optimized and improved feel.

During the research leading up to the present invention, in the applied form, it was found that The degree of dispersion or emulsification of the compound in It was also found that this could have great implications for the effectiveness of the system. Regarding the pure effect but also with regard to long-term maintenance of efficacy, especially in aqueous mixtures. emulsify or emulsify the active substances very finely to a high degree that is unaffected by storage. It is important to be diversified. There are two possibilities in this respect, which in combination with each other Good too. i.e. for the preparation of active substance combinations, especially aqueous combinations. Certain methods should be employed in the production of aqueous formulations using dispersing or emulsifying aids. use. In this regard, the following findings apply: The longer the chain length of . Substituents xl and X! Compounds having more than 14 carbon atoms in them, especially , a carbon atom range of about 16 to 20, which is particularly effective for the textile softening purpose of the present invention. ranges typically include the presence of additional ingredients in the mixture of active substances, such as those mentioned above. I need. In such a case, in one important aspect of the present invention, general formula (1) A thiodiglycol compound represented by is used in combination with a surfactant auxiliary agent. this In a broad sense, surfactants are effective auxiliaries. Therefore, the present invention provides anion mixtures with surfactants and corresponding mixtures with nonionic surfactants. It includes both. Suitable anionic surfactants include, for example, fatty alcohols. Rusulfate salts and alkyl sulfonate salts, alkali metal salts and Alkaline earth metal salts are preferred, with Na and Mg salts being particularly preferred. Is it the first group? et al. use tallow alcohol sulfate and related compounds as particularly suitable mixture components. Can you name something? The second group includes, for example, α-sulfo fatty acid methyl ester sulfonate nate, alkylbenzene sulfonate, alkanesulfonate, α-sulfolipid Includes fatty acid di-salts and similar compounds. From the range of nonionic surfactant ingredients , standard oricoethoxylates of lipophilic components that contain active hydrogen atoms, and special Any of the alkyl glycolides belonging to the group of nonionic surfactants. It will be done. In order to optimize according to the invention, it is necessary to obtain the desired improvement in the textile softening effect. Of course, it is of great importance, especially for textile soft The overall compatibility of the softening aid will also have to be considered. Therefore, especially The key is tallow alcohol sulfate, wetting or emulsifying alkyl glucono compound and/or α-sulfo fatty acid di-salt with wetting and emulsifying properties. be.

Other groups for the preparation of highly active formulations, especially aqueous formulations, of compounds of general formula (1) Auxiliary agents are emulsifiers or emulsifiers to maintain the very fine emulsification or dispersion achieved. It is a stabilizer. Many compounds of this type are known to those skilled in the art. For the purpose of this invention Particularly suitable compounds of this type include, for example, in addition to one or two free hydroxyl groups: Glyceros with relatively long hydrocarbon chains in the ether- or ester-forming substituents glycerol partial ether and/or glycerol partial ester.

Such a mixture of the thiodiglycol compound represented by the general formula ([) and the said auxiliary agent In a product, the thiodiglycol compound of the present invention has a concentration of 5 to 95% based on the entire mixture. It may be present in an amount of % by weight, preferably from about 20% to 70% by weight. sulfone and / or sulfoquintes and particularly effective emulsifying auxiliaries, especially surfactant-like auxiliaries The a scuttling with is in the range 1.5 to 5:1, especially about 13.5 to 4.1. Can be range or advantageous.

Said second possibility for increasing the effect of the compounds of the invention is for softening textile products. active concentrates, especially aqueous active concentrates, which are further diluted with water before actual use. It depends on the selection of manufacturing conditions. In this regard, two process parameters should be taken into account in particular: In order to ensure particularly fine emulsification, it is necessary to The emulsification of the active substance or mixture thereof in the aqueous phase is carried out at temperatures ranging from at least room temperature to about 100 ml. It turned out that it was appropriate to use 'C'. That is, preferably about 80 to It may be advantageous to carry out the emulsification at a temperature of 95°C. In this respect, the aqueous phase and mix very vigorously with the active substance phase containing the molten thiodiglycol compound. It is important to. Continue vigorous mixing while cooling the aqueous concentrate to ambient temperature. It can also be advantageous to

For example, a thiodiglycol compound represented by the general formula (1) is When used with phase-type dispersion or emulsification aids, the active substance mixture In particular, first intensive homogenization in the melt and then the mixture in the aqueous phase under the conditions mentioned above. It has also been found that emulsification is particularly preferred. As shown in the figure, fine emulsification is particularly important. It is not only possible to increase the effectiveness and therefore strengthen the effect for the intended application. This results in active substance concentrates that remain stable even during long-term storage.

In the production of such aqueous dispersions and/or emulsions, the production The active substance content in the aqueous formulation is about 1 to 50% by weight, especially about 5 to 20% by weight. It is preferable to set it as the range of %. For textile softening, especially for final rinse softening At the working concentrations of such emulsions, the active substances of the invention or mixtures thereof are The final amount of the compound used is about 0.405 to 2% by weight based on the dry weight of the textile product, especially The concentrate may be used in an amount of about 0.1 to 0.5% by weight.

The aqueous textile softeners of the present invention can be prepared over a relatively wide range of pH values.

That is, the pH value of such aqueous solution ranges from about 4 to 11, preferably about 55. ~1o.

Furthermore, the hardness of the water used in the final rinse softening is determined by the hardness of the water used in the final rinse softening. I found that it had no effect on the effect. However, it is possible that there is a certain degree of low hardness. It is advantageous. i.e. at least 5° Gb (=German hardness), especially about 8 to 3 Hardnesses in the 0'Gh range or above are particularly suitable for obtaining the desired softening effect. That's true.

The active substances or mixtures thereof according to the invention are suitable for wetting or drying the textiles to be treated. However, it can be used to soften textile products. Even when processing wet textile products The desired softening effect can also be obtained in the treatment of dry textile products. of the present invention Active substance mixtures are usually applied to such textiles, even from aqueous solutions, by pressing. It is also adsorbed. The tactile quality imparted by the active substance mixture according to the invention is It is not possible to directly compare the results with those actually obtained in the past. With the active substance mixture according to the invention The treated textiles are found to be very highly flexible and dry comfortably.

Example Bis-g2-<2-hydroxyalkoxy)-ethyl]-sulfoxy 45% hydroxyl 1,2-epoxyhexadecane (α -C11-18 olefin epoxy 7) 654. sg and bis-(2-hydro 152.7 g of sulfide (thiodiglycol) was introduced, and the presence Traces of water were removed by heating to 80-100°C under reduced pressure.

This slightly exothermic mixture was heated to about 160-170'C in a nitrogen atmosphere. heated to.

In order to monitor the reaction, we measured the content of ebo beef at regular intervals, and the reaction was Typically, it was stopped after 3-6 hours when the epoxide oxygen content was less than 0.2%. Living Bis-[2-(2-hydroxyhexadenyloxy)-ethylcosulfate] oxidize to both the sulfoxide and the corresponding sulfone by the following method: I was able to do that.

a) Oxidation to sulfoxide Half amount of bis-C2-(2-hydroxyhexade/luoki/)-ethylyosulfur 100 ml of glacial acetic acid was added to the solution, which was then heated.

304 g of 70% hydrogen peroxide are added dropwise at approximately 60°C. and a = substance causes an exothermic reaction. I strained it. The reaction temperature should not exceed 90'C. Approximately 5 at 80°C The reaction was stopped after an hour. Next, test the wash water for peroxide until a negative result is obtained. Then, the reaction mixture was washed with hot water. Finally, the yellow solid sulfoxide was heated to 120°C. and dried under reduced pressure.

Bis-E2-(2-hydro+)to-decyloxy)-ethylcosulfoxy/do Analysis data: OH value 209.5, acid value 04゜b) Oxidation to sulfone the other half of bis-E2-(2-hydroxyhexadenoroxy)-ethylco 100II11 of glacial acetic acid was added to the sulfite which was then heated. Next, 7 When 60.8 g of 0% hydrogen peroxide was added dropwise at approximately 60°C, the mixture underwent an exothermic reaction. Ta. Oxidation and processing conditions were the same as for the sulfoxide. Problem with separation In some cases, butyl acetate as a solvent and a 5% aqueous solution of sodium sulfate are separated. It was used as a release aid. Bis-r2-(2-hytroquinehexadecyloxy)- Analysis data of ethyl sulfone, OH value 156.4, acid layer 1.2゜Like this The thiodiglycol sulfoxide and thiodiglycol of the present invention produced by Examples of mono- and bis-ethers of sulfone are shown in Tables 1 and 2.

Table 1 Mono- and bis-7d thiodiglycol sulfoxide Table 2 Thiodig Recall sulfone mo/- and bis-bis-C2-(alkylcarbonyloxy) 7) -Ethyltusulfoquine 2 moles of the corresponding fatty acid and bis-(2-hydroxy ethyl)-sulfide (thione glycol) was placed in a stirred reactor and weighed (on a scale). After adding 5 g of tin particles (per 1000 g of the total amount weighed), approximately 20 g of tin particles were added in a nitrogen atmosphere. Heated to a reaction temperature of 0°C. The acid value, which should be less than 5, is The required amount of thiodiglycol can be monitored from the amount of 5 to 10 could be added over time. Complete the reaction to remove tin particles Afterwards, the reaction mixture was filtered hot with suction through Celite.

The reaction product was added to the intermediate at a temperature of about 60°C with 1 mol of hydrogen peroxide (70%). or oxidized to sulfoxide or sulfone by dropping 2.1 mol did. Since it is a highly exothermic reaction, the reaction mixture must be cooled if necessary. won. At a reaction temperature of about 90'C, reaction time was 4-6 hours. Next, wash The reaction mixture was washed with hot water until the purified water was free of peroxide. minutes In case of separation problems, butyl acetate was used as the solvent. Corresponding bisue The stealth sulfone and bis-ester sulfone were dried under vacuum at 1200C. It was dry.

Thiodiglycol sulfoxide and thio/glycol thus produced Examples of sulfone mono- and bis-esters are shown in Table 3.

Table 3: Thiodiglycol sulfoxide (A) and sulfone DIN 109 Softening effect on cotton by 54 (sensory test, pairwise comparison), on dry weight active substance 05%; bath 1:20: water hardness] 6°Gh, blank value -1 (water), Maximum value -4 (compound D)' Measured value at a climbing altitude of 70 m1 according to DIN 53924 Absorption capacity of 2x2cm cotton terry fabric as 35% working solution 4 Weak, medium or strong odor evaluation (Examples 1 to 9 - Sulpokind's, Example 1 0-improper tool) A bis-12-(2-hydroxydodecyloxy C) - Ethylcosulfoxy/t B Bis-[2-(2-hydroxyhexadeneluoki/)-ethyl]-sulfoki /do C sulfopon T55 (tallow alcohol sulfate (Na salt) D Dimethylnestearylammonium chloride According to Table 4, compound AIO% , Compound 830% and Compound C 60% mixture (Example 6) Comparable to the commercial active substance mixture (Example 10) in terms of yield and furthermore has a lower odor and brightness. Compared to conventional technology, it is environmentally friendly because it contains less nitrogen and does not contain nitrogen. I can see that it is also excellent.

Table 5, aqueous active substance mixtures with tallow alcohol sulfate/sulfone a nature of A, bis-E2-(2-ethyl/)-ethyl]-sulfone B: Sulfobone T55 (tallow alcohol sulfate, Nap) C industrial water (approx. 16°Gh) 1 In evaluating the feel imparted by the novel N-free softener of the present invention, “ It was impossible to describe it as having a similar feel. The feel is ``comfortable,'' ``dry,'' and ``light.'' I was able to express this as ``pleasant'' and ``flexible.'' Using the applicant's own @touch criteria , according to the modified DINIo954, we can define the observed feel as follows: Sharp: O = roughest feel (no fabric softener) 4- Softest feel (mixture 5) Mixtures 8.9 and 1o were not tactile tested due to their high viscosities. 4-8 The a-compounds were found to be equivalent to each other with respect to the feel they impart.

11 Wasokar (Waac k e r) tester, bath ratio 1:10, 10% Softener 0.3% (on test material) in aqueous textile softening mixture, processing time 5 minutes, water hardness 16°Gh 12 Washing machine time (M1ele)-W717”, Wash at 60°C, 0.3% softener (on test material) in 10% aqueous textile softening mixture, water Hardness of 16°Gh 2 Viscosity measured with a Haake falling ball viscometer [Hdpple r) 1 Table 5 lists aqueous actives containing tallow alcohol sulfates/sulfones. Regarding the new tactile evaluation of quality mixtures, this This cannot correspond to the tactile evaluation used. In particular, Examples 4 to 7 have a favorable viscosity. , which was preferred for practical applications.

A: Bis-[2-(2-hydrocyhexadecyloxy)-ethyl]-sulfone B: Sulfopone T55 (tallow alcohol sulfate, Na salt) C: A33% B67% D, Texin E S 68 (C+s-+s fatty acid methyl ester Rusulfonate) E: APG501 (C++-+a alkyl polygluco/do) F eumulgin (E umulgin) S M S 20 (polyethylene glycol-20 -sorbitan monostearate) G: APG225 (C,,, alkyl poly glucoside) H industrial water (approximately 16°Gh)’ 1. The test fabric should be processed in a washing machine (see Table 6)'' according to DIN 53924. Absorption capacity (measurement of rising height) '3.1 + Measured 24 hours after emulsion preparation pf (value 3.2. pH value measured after storage for 2 months at room temperature In Table 6, the present invention An aqueous active substance mixture containing a clear thiodiglycolsulfone (formula 11A) is Optimized for feel, absorption and pH stability during storage due to the addition of emulsifiers has been done. The white-blue emulsions of Examples 1 and 2 were used in a washing machine. It was found to be effective as a softening agent.

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Claims (16)

[Claims] 1. General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, X1 and/or X2 are β-hydroxyl-substituted alkyl group having 8 to 30 carbon atoms and/or carbon represents an acyl group of an alkyl monocarboxylic acid having 8 to 30 atoms, X1 and X2 may be the same or different; in the case of monoethers and monoesters, 1 or X2 is hydrogen, and z is a number of 1 or 2. ] A novel thiodiglycol sulfoxide and/or sulfone represented by mono- and/or bis-ethers and mono- and/or bis-esters Le. 2. Substituents X1 and X2 have 12 to 24 carbon atoms, preferably 12 to 18 carbon atoms preferably linear β-hydroxyl-substituted alkyl group and/or alkyl group having The thiodiglycol according to claim 1, which is derived from a syl group. compound. 3. X1 and and thiodiglycolsulfone (z=2 ) is preferred, the thiodiglycol compound according to claim 1 or 2, wherein . 4. A method for producing a thiodiglycol compound represented by general formula (I), comprising: Diglycol and C8-30 α-olefin epoxide or C8-30 alkyl monocarboxylic acid at a molar ratio of 1:1 to 1:2 to obtain a mono-carboxylic acid. and/or bis-ethers or mono- and/or bis-esters. characterized by oxidation to sulfoxide and/or sulfone by known methods. How to do it. 5. The reaction between thiodiglycol and C8-30 α-olefin epoxide is at a temperature of at least 120°C to about 200°C, preferably about 5. Process according to claim 4, characterized in that it is carried out at a temperature of 160-170<0>C. 6. The basic catalyst used is a base with alkaline action, such as alkali hydroxide. compounds and/or alkali methoxylates, with a small amount compared to the total weighed amount. at least 0.05% to about 5% by weight, preferably about 0.1 to 1% by weight. 6. A method according to claim 4, characterized in that it is used in a quantity. 7. The reaction is carried out for about 3-6 hours and the epoxide oxygen content is less than 0.5%. , preferably less than 0.2%. How to put it on. 8. If necessary, they themselves have detergency and/or detergency-enhancing action. In addition to solvents, dispersion aids, emulsifiers and/or stabilizers represented by general formula (I), A textile softening active substance mixture containing a thiodiglycol compound. 9. of general formula (I) mixed with dispersing aids, emulsifiers and/or stabilizers The thiodiglycol compound is preferably added in an amount of 5 to 95% by weight, based on the active substance mixture. or in an amount of 20 to 70% by weight, preferably in the form of an aqueous mixture. 9. Active substance mixture according to claim 8, characterized in that: 10. Thiodiglycol compounds can be used as surfactant components, emulsifiers and/or stabilizers. agents, such as glycerol partial esters and/or ethers. Active substance mixture according to claim 8 or 9, characterized in that: 11. Thiodiglycol compounds, as a mixture with alkyl glycosides, are Ionic surfactants, e.g. fatty alkyl sulfate-containing anionic surfactants as a mixture with tallow alcohol sulfate, especially as a mixture with tallow alcohol sulphate. and/or as a mixture with a nonionic surfactant. Active substance mixture according to claim 10. 12. The thiodiglycol-containing active substance mixture can be added to an aqueous solution and/or dispersion. The active substance content in the liquid or emulsion is from 1 to 50% by weight, preferably from about 5 to 50% by weight. The activity according to any one of claims 8 to 11, characterized in that the content is 20% by weight. substance mixture. 13. On the one hand, in the β-hydroxyl-substituted alkyl groups (X1 and X2), respectively and a compound of general formula (I) having about 10 to 14 carbon atoms, preferably 12 carbon atoms; , on the other hand 16 to 20 carbon atoms in the corresponding groups X1 and X2, preferably characterized by the presence of a combination of compounds of general formula (I) having 16 to 18 Active substance mixture according to any of claims 8 to 12. 14. Especially in the final rinse softening, it is preferable for the dry weight of the textile product. is an amount of 0.05 to 2% by weight of active substance, more preferably about 0.1 to 0.0% by weight of active substance. a thiodiglycol compound of general formula (I) used in an amount of 5% by weight or solubilization; Laundry detergents and/or fibers in their mixtures with emulsifying and/or dispersing aids Use as a textile softening component in product softeners. 15. Normal hardness, preferably in the range of about 5-30°Gh, and about 4-1 Using an aqueous formulation with a pH value in the range of 1, preferably in the range of 5.5 to 10 The use according to claim 14, characterized in that: 16. Claims characterized in that they use aqueous active substance preparations prepared as follows: Use according to item 14 or 15: The compound represented by general formula (I) is used as a dispersing agent, milk, etc. in highly concentrated form, optionally intensely in the melt phase, together with oxidizing agents and/or stabilizers. and then at least room temperature to about 100°C, preferably about 80-95°C. ℃ treatment in the aqueous phase to commercialize and/or use the novel active substance mixtures. form.