JPS6042315B2 - Composition for preparing textile products - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides a method for preparing textile products (COIl) containing imidazolinium salts that are essentially free of amines and amine salts.
ditiOning) composition.

In conventional home washing operations, soiled textile products are washed using a detergent composition in the main wash cycle, and then rinsed with water in the final cycle. A textile conditioning composition is optionally added during the rinse cycle. Such compositions contain textile softeners or textile antistatic substances to impart softening and antistatic properties to the washed textiles. Thereafter, the rinsed textile product is often dried in an automatic clothes dryer. Many different types of textile conditioning agents have been used in rinse cycles to which textile conditioning compositions are added.

The most preferred class of drugs were quaternary ammonium compounds. These compounds may take the form of acyclic quaternary ammonium salts having preferably two long-chain alkyl groups attached to the nitrogen atom. Additionally, imidazolinium salts have been used alone or in combination with other agents to treat textile products. U.S. Patent No. 2874 dated February 17, 195
No. 074 discloses the use of imidazolinium salts for preparing textile products.

U.S. Pat. No. 3,681,241, dated Aug. 1, 1972, and U.S. Pat. No. 3,033,704, May 8, 1962, disclose textile conditioning compositions containing mixtures of imidazolinium salts and other textile conditioning agents. It has been disclosed.

Although the prior art indicates the use of quaternary imidazolinium salts as textile conditioning agents, the problems encountered in producing stable textile conditioning compositions containing such agents and aldehydes are not mentioned. It has not been.

The production of imidazolinium salts generally involves reaction of a polyamine to form an imidazoline with an acyl-containing material such as an acid or ester, followed by quaternization of the imidazoline. US Patent No. 235 dated August 15, 194
No. 5837 and No. 2267 dated December 30, 1941
No. 965 and US Pat. No. 2,520,102 dated Aug. 22, 195, disclose a method for producing imidazolines for use in the production of imidazolinium salts.

In the present invention, it has been found that in addition to the imidazoline compound produced in the above reaction, primary and secondary amines also exist. During the subsequent quaternization step, these amines result in the formation of imidazoline amine salts rather than quaternary imidazolinium salts from some imidazoline compounds. The imidazoline amine salt, when present in an aqueous medium of near neutral or higher pH, can be ring-opened to produce a free amine. This amine will react with the aldehyde compound in the composition to the same extent as the free amine that has not been converted to salt form. the result,
The fragrance of the composition deteriorates (perfumes generally contain aldehydes), the color and PH change, and the aldehyde retention deteriorates. The above-mentioned U.S. Pat. No. 2,874,074 describes the preparation of quaternary imidazolinium salts, but how can the above-mentioned problems be overcome and the imidazolinium salt content high enough to be commercially attractive? There is no description of obtaining the desired product. From the perspective of the process of the present invention, the undesired amines are single-terminally capped using an alkoxylating agent, which caps primary and secondary amines but does not contain imidazolinium salts. A sufficient amount of the cyclic tertiary amine that is formed is used so that it is not too sequestered. Therefore, the object of the present invention is to
It is an object of the present invention to provide a composition for preparing textile products that includes a quaternary imidazolinium salt and is essentially free of amines and amine salts. This and other objectives will become apparent from the description below.

All percentages and ratios herein are by weight unless otherwise indicated.

SUMMARY OF THE INVENTION The present invention relates to a composition for preparing textile products containing an imidazolinium salt having the following formula.

wherein R and R1 are aliphatic or cycloaliphatic hydrocarbon groups containing about 10 to about 22 carbon atoms. D is H, -+. CnI(2n'+-, ah,,-,X,TT
selected from the group consisting of 几 and (℃H2■toichi℃-11 (where n is 1 to about 6).

X is negative. R2 is alkyl (containing about 1 to about 8 carbon atoms), substituted alkyl, or aralkyldi. R3 and R are hydrogen, a hydroxyl group, a short chain alkyl having 1 to 4 carbon atoms, or a hydroxyl group bonded to the short chain alkyl. In some desired forms, D is absent and R1 can be bonded directly to the nitrogen in position 1 of the ring. In other desired forms,
R1 and D may be absent and in their place an amine group forming an imidazoline. The imidazolinium salts are essentially free of amines, amine salts and alkoxylated forms of imidazolinium salts. Although the formula shows an R2 group on the nitrogen in the 3-position, it should be understood that the R2 group may also be on the nitrogen in the 1-position. DETAILED DESCRIPTION OF THE INVENTION The quaternary imidazolinium salts essentially free of amines, amine salts and alkoxylated forms of the imidazolinium used in the compositions of the invention are prepared as follows.

The reaction to produce the desired imidazolinium salt includes the following steps. Production of Imidazoline The imidazoline precursor of the desired imidazolinium salt is
The acylating or esterifying agent has two or three amino groups, and one of the amino groups is a primary or secondary amino group in the 2-position relative to the primary amino group. Produced by reacting with alkylene or polyalkylene polyamines.

This reaction is carried out at temperatures of about 100 to about 250°C and
From about 0.33:1 to about 1.5:1 over about 2 bridges, preferably! 0 is carried out at molar ratios of acyl groups to primary amine and hydroxyl groups ranging from about 1:1 to about 1.5:1 and under reflux or at atmospheric or slightly elevated pressure.
To promote the formation of imidazoline ring A, the reaction mixture can then be subjected to a vacuum of about 0.4 to about 10 mm of mercury for about 1 to about 8 hours. The resulting mixture contains, in addition to the desired imidazoline, some amount of raw acylating agent, raw polyamine, uncyclized intermediate amide product, and other mixed reaction products. The acylating or esterifying agent 40 can be an acid or other acyl-containing compound having an aliphatic or cycloaliphatic hydrocarbon group of about 10 to 22 carbon atoms. Examples of such materials include lauric acid, decanoic acid, undecanoic acid, dodecanoic acid,
These include fatty acids such as tridecanoic acid, myristic acid, pentadecanoic acid, hexadecanoic acid, and palmitic acid. Preferred fatty acids are mixtures thereof derived from tallow, soybean oil or coconut oil. Particularly preferred are
It is a soft or hardened tallow fatty acid. Other acylating or esterifying agents include alkyl esters of the fatty acids and naturally occurring glyceride esters. The latter are preferably used according to the invention. Polyamine materials such as those described above have two or three amino groups, one of which is a primary or secondary amino group at the 2-position relative to the primary amine group. Preferably, these polyamines have the formula: Here, X is, for example, hydrogen, one (
CH2-0H2)n-NH2,-(CH2-CH2)n
-0H or one (CH2-CH2). ．． -CH3, where n is 1 to about 6.

). Examples of such polyamines include diethylenetriamine, ethylenediamine, hydroxyethylethylenediamine, and the like. Addition of a Second Long Chain Alkyl or Substituted Alkyl Group As described above, the production of imidazolines is accomplished by reacting polyamines with acylating or esterifying agents.

If the amount of acylating or esterifying agent used is not sufficient to form an amide or ester with at least two of the amine or hydroxyl groups present in the polyamine (an acyl group versus a primary amine or hydroxyl group) molar ratio is approximately 0
．． 33 to about 0.66), the imidazoline produced will only have long chain groups located at the 2-position rather than at both the 1- and 2-positions of the imidazoline ring. The monosubstituted material then has to be further reacted with an acylating or esterifying agent. The reaction temperature in this case is generally equivalent to the overall reaction described above when the molar ratio of acylating or esterifying agent to monosubstituted imidazoline ranges from about 1:1 to about 1.5:1;
And the reaction time spans about 1-2 bars. As desired,
The pressure is reduced to a degree of vacuum of about 0.4 to about 10 Tfrm of mercury. This reaction can be exemplified below using diethylenetriamine as the polyalkylene polyamine. wherein R is an aliphatic or alicyclic hydrocarbon group containing about 10 to about 22 carbon atoms. Then,
In the imidazoline formed above; the primary amine present must be converted to an amide to attach the second long chain R group as follows.

wherein R1 is an aliphatic or cycloaliphatic hydrocarbon group containing from about 10 to about 22 carbon atoms.

Above formula 0 10 6ゝ7ゝ 1℃H,. -CH. ,1-N
The T-1J- group corresponds to D in the formula described in the Summary of the Invention section above. It is to be understood that D may be another divalent group or may be absent depending on the selection and concentration of the polyamine and acylating or esterifying agent. For example, in the above-mentioned US Pat. No. 2,267,965, a hydroxyl group is bonded to the 1-position of the imidazoline ring. Other polyamines are also described in the aforementioned US Pat. No. 2,355,837. Of course, if the amount of acylating or esterifying agent used contains enough acyl groups to form an amide or ester with at least two of the amines or hydroxyl groups (acyl vs. primary amine or hydroxyl group). The ratio is about 0.67~
1.5:1, preferably from 1:1 to about 1.1:1), the long chain group at the 1 position will be present as a result of the initial imidazoline forming reaction.

Such a reaction is represented by the following formula. Some of the intermediate amides shown above, as well as some of the starting materials, other intermediates, water and other compounds are present as diluents along with the desired substituted imidazoline.

Some of the diluent is removed during the depressurization process of the reaction. Alkoxylation of Imidazolines In the formation of this 1,2-substituted imidazoline product, in addition to the desired imidazoline product, other components will be present, such as those found as diluents in the glyceride reactions described above.

The production of the imidazoline reaction is the reaction of the fatty acids described above, where the disubstituted imidazoline is first produced and then a second long chain aliphatic or cycloaliphatic hydrocarbon group is reacted with the fatty acid or other agent. When added to the 1st position by , the desired imidazoline will be present in a mixture containing some imidazoline substituted only at the 2nd position and the fatty acid or other agent. Similarly, regardless of which reaction route is taken, the primary and (
or) a secondary amine will be present in the final product mixture. Materials having primary or secondary amine groups present in this way are converted into amine salts, rather than quaternary salts, of the disubstituted imidazoline in the quaternization step described below. This is undesirable because it causes It should be noted that the quaternary salt is capable of reverting to the free amine when present in an aqueous composition at a pH of about 5 or greater. U.S. Patent No. 287, dated February 17, 1959, supra.
In the specification of No. 4074, 1,2
The production of substituted imidazolines is disclosed. 1
U.S. Patent No. 2,355,837 or 1 dated August 15, Group 94
A 2-mono-substituted imidazoline as prepared in US Pat. No. 2,267,965, dated Dec. 30, 1994, is utilized in the invention of US Pat. No. 2,874,074.

Imidazoline products such as those produced by this '074 invention would contain a mixture of 1,2 monosubstituted, 21 substituted, other amine-containing materials, and fatty acids. Since the 2-substituted substance and other amines have the ability to form imidazoline salts as described above,
Undesirable. The inventors have discovered that the undesired amine products present in this 1,2 monosubstituted imidazoline reaction mixture can be effectively sequestered by treating the mixture with an alkylene oxide, preferably propylene oxide. I found it. Capping the free amine by attaching an alkylene oxide moiety to the free amine,
The alkylene oxides are useful. It is important that all of the primary and secondary amines are capped and that the tertiary amine in the imidazoline is capped to a minimum. To accomplish this, a mixture containing the desired 1,2-monosubstituted imidazoline is treated with an alkylene oxide in an amount of about 1 to 5% by weight of the mixture to be treated, for a period of about 80
A to maintain a temperature of about 140°C and about 2 to about 157,077 columns of mercury! Reduce the pressure to a degree of vacuum as desired. Vacuum pressure facilitates removal of excess alkylene oxide, polyamines, and other low boiling diluents from the system. The alkylene oxide treatment can also be accelerated by diluting the imidazoline-containing mixture with an organic solvent such as isopropyl alcohol or glyme. Such solvents are used in amounts of about 1 to about 25% by weight of the imidazoline mixture. Reaction times range from about 0.5 hours to about 8 hours. U.S. Patent No. 27 dated July 19, 1955
1358? The specification discloses the production of fully alkoxylated imidazolines as precursors for carboxylate detergent products.

Examples of alkoxylating agents other than propylene oxide include butylene oxide, glycide, ethylene oxide, cyclohexane oxide, and the like. Quaternization The alkylene oxide treated mixture obtained above is treated with an alkylating agent to form the desired quaternary imidazolinium which is essentially free of amines, amine salts and imidazolinium salts in alkoxylated form. Generates a substance. The imidazolinium products total less than about 4% (preferably about 2%).
%) primary amines, secondary amines and cyclic tertiary amine salts, and less than about 25% (preferably about 4
%) of the imidazolinium salt in alkoxylated form. The restriction on the alkoxylated form is a result of the desire to produce as pure a non-alkoxylated imidazolinium salt as possible and is not related to amine/amine salt stability issues. The alkylating agent can be any of the known agents such as methyl chloride, ethyl bromide, diethyl sulfate, dimethyl sulfate, hexadecyl chloride, and many other agents. This reaction can be exemplified as follows. Here, D, R, Rl, R
3 and R4 are as described above. The amount of alkylating agent used should be equivalent on a molar basis to the amount of imidazoline treated.

However, to ensure maximum tertiaryization, an excess of alkylating agent is generally used. The amount of excess employed is
The amount should be sufficient so that the pH of the reaction medium is in the range of about 5 to about 7. Reaction times generally range from about 1 to about 1 hour, and reaction temperatures range from about 400 to about 80°C. If desired, a base can be added during the alkylation step to facilitate quaternization. The imidazolinium salts produced as described above have remarkable textile conditioning properties such as softening and antistatic properties, and also enable the production of textile conditioning compositions with improved aldehyde stability. I also do it.

Preferred imidazolinium salts are those having 14 to 2 carbon atoms, such as the following formula, where the R group is a tallow hydrocarbon.
1 and R groups. Here, C (tallow-based) is an aliphatic hydrocarbon chain derived from tallow fatty acid. Other quaternary imidazolinium salts with desirable properties include different R
groups are generated by using different alkylene or polyalkylene polyamines in place of diethylenetriamine, different alkyls, substituted alkyls or aralkyl in place of the methyl groups present, and different anions in the acylating agent. be able to.

Compositions for Preparing Textile Products The present invention relates to a composition comprising a 1,2-monosubstituted quaternary imidazolinium salt, the composition comprising a total of about
% (preferably less than about 2%) of primary amines, secondary amines and cyclic tertiary amine salts.

Additionally, the composition preferably contains less than about 25%, and more preferably less than about 4%, of the alkoxylated form of the imidazolinium salt, based on the weight of the non-alkoxylated form of the imidazolinium salt. preferable. Producing the desired imidazolinium salt by employing the above-mentioned process or by using other methods that produce the imidazolinium salt and do not by-produce various undesirable compounds in amounts greater than the above-mentioned amount. I can do it. As mentioned above, the imidazolinium compounds of interest of the present invention have the following general formula: wherein R and R1 are aliphatic or alicyclic hydrocarbon groups having about 10 to about 22 carbon atoms.

R3 and R4 are hydrogen, a hydroxyl group, a short-chain alkyl group having 1 to 4 carbon atoms, or the short-chain alkyl group of the hydroxyl type. D is selected from the group consisting of H, -(C 几 , where n is a number from 1 to about 6.
R2 is an alkyl, substituted alkyl or aralkyl group having about 1 to 8 carbon atoms and which was attached to the alkylating agent used to quaternize the imidazoline compound. Examples of such cations include methyl, ethyl, benzene, and the like. X is an anion bound to the alkylating agent, and particular examples include chlorine, bromine, methyl sulfate, ethyl sulfate, and the like. Although the quaternization is shown to have occurred at the 3-nitrogen, it should be recognized that quaternization at the 1-nitrogen atom is not excluded. A preferred quaternary imidazolinium salt is the methyl sulfate salt described above. The compositions of the invention are preferably aqueous and can contain any desired amount of quaternary imidazolinium salt.

However, it is preferred that the composition contain from about 1 to about 15% of the salt, and most preferably from about 2 to about 8% of the salt. In addition to such preferred quaternary imidazolinium salts, the compositions of the invention may also contain other textile conditioning (softening/antistatic) agents.

Such other agents can be described as being cationic or non-ionic organic substances that do not contain primary amines, secondary amines and cyclic tertiary amine salts, and are used in textile conditioning during the rinse cycle of household washing operations. It is commonly used as an agent. Such drugs range from 25 to 115
It is a waxy organic substance with a melting point (or softening point) of °C. This material has both textile softening and antistatic properties. Generally, cationic nitrogen-containing compounds such as quaternary ammonium compounds have one or two straight chain organic groups of at least 8 carbon atoms.

Preferably, the compound has one or two carbon atoms
It has two such groups. Preferred cationically active softener compounds include quaternary ammonium salts corresponding to
Contains antistatic/softener compounds. Here, R1 is hydrogen or an aliphatic group having 1 to 22 carbon atoms, R2 is an aliphatic group having 12 to 22 carbon atoms, and R3 and R
4 is each an alkyl group of 1 to 3 carbon atoms and X is an anion selected from halogen, acetate, phosphate, nitrate and methyl sulfate.

Preferred cationic antistatic/softener compounds for use in the present invention are dialkyldimethylammonium chlorides because of their superior softening performance and because they are readily available. Here, the alkyl group is 12-2
It has two carbon atoms and is derived from a long chain fatty acid such as hydrogenated tallow. In the present invention, alkyl is intended to include unsaturated compounds such as those present in alkyl groups derived from naturally occurring fats and oils. The term tallow refers to an aliphatic alkyl group derived from tallow resin acids.

From such fatty acids, R1 and R2 are mainly from 16 to
A quaternary softener compound having 18 carbon atoms is formed. 1. The term coconut refers to fatty acid groups derived from coconut oil fatty acids.

The coconut alkyl groups R1 and R2 have from about 8 to about 18 carbon atoms and are primarily Cl. ~Cl4 is an alkyl group. Representative examples of the quaternary softening agent in the present invention include tallow trimethylammonium chloride, ditallow dimethylammonium chloride, ditallow dimethylammonium methyl sulfate, dihexadecyldimethylammonium chloride, di(hydrogenated tallow) dimethyl Ammonium chloride, dioctadecyldimethylammonium chloride, dieicosyldimethylammonium chloride, didocosyldimethylammonium chloride, di(
hydrogenated tallow) dimethylammonium methyl sulfate,
These include dihexadecyldiethylammonium chloride, dihexadecyldimethylammonium acetate, ditallow dipropylammonium phosphate, ditallow dimethylammonium nitrate, and di(coconuttoalkyl)dimethylammonium chloride. A particularly preferred class of quaternary ammonium antistatic/softening agents in the present invention corresponds to:

Here, R1 and R2 each represent 12 to 22 carbon atoms.
straight chain aliphatic groups, and X is a halogen such as chlorine or methyl sulfate. Particularly preferred are ditallow dimethylammonium chloride and di(hydrogenated tallow dimethylammonium chloride).
alkyl)dimethylammonium chloride and di(coconuttoalkyl)dimethylammonium chloride, these compounds being preferred in view of their excellent softening properties and easy availability. Nonionic textile antistatic/softener materials include a wide range of materials including sorbitan esters, fatty alcohols and their derivatives, and the like.

One preferred class of nonionic textile antistatic/softener materials contains esterified cyclic dehydration products of sorbitol, ie, sorbitan esters. Sorbitol produced by catalytic hydrogenation of glycose can be dehydrated by known methods to produce a mixture of cyclic 1,4- and 1,5-sorbitol anhydrides and small amounts of isosorbide. (See U.S. Pat. No. 2,322,821, June 29, 1943.) The resulting complex mixture of cyclic anhydrides of sorbitol is collectively referred to in the present invention as 1 sorbitan. It will be seen that this 1-sorbitan mixture also contains some free uncyclized sorbitol. Sorbitan ester textile antistatic/softener materials useful in the present invention include, for example, fats (ClO-C24
) is prepared by esterifying the 1 sorbitan mixture with fatty acyl groups in standard manner such as reaction with acids or fatty acid halides.

The esterification reaction can occur with any existing hydroxyl group, and various mono-, di-, etc. esters can be produced. In fact, Mono, Gee, Tory,
Complex mixtures of and tetra-esters are always used from such reactions, and the stoichiometric ratios of the reactants can be easily adjusted to obtain the desired reaction product. The above-mentioned complex mixture of esterified cyclic dehydration products of sorbitol (and a small amount of esterified sorbitol) is collectively referred to as zero sorbitan esters in the present invention.

Sorbitan mono- and di-esters of lauric acid, myristic acid, palmitic acid, stearic acid and behenic acid are particularly useful in the present invention for conditioning the textiles to be treated. Mixed sorbitan esters, such as mixtures of the esters listed above, and mixtures prepared by esterifying sorbitan with fatty acid mixtures, such as mixed fatty acids of tallow and hydrogenated coconut oil, are useful in the present invention and are economically attractive. be. Unsaturated ClO-Cl8 sorbitan esters, such as sorbitan monooleate, are usually present in such mixtures. All sorbitan esters and mixtures thereof that are essentially water-insoluble and have an aliphatic hydrocarbyl end are useful textile antistatic/softener materials in connection with the present invention. Preferred alkyl sorbitan ester textile antistatic/softening agent materials in the present invention include sorbitan monolaurate, sorbitan monomyristate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monobehenate, sorbitan dilaurate, sorbitan Dimyristate, sorbitane dipalmitate, sorbitane distearate, sorbitane dibehenate, and mixtures thereof, mixed coconut alkyl sorbitan mono and di esters, and mixed tallow alkyl sorbitan mono and di esters. Also useful in the present invention are tri- and tetra-esters of zorbitan with lauric, myristic, stearic, and behenic acids, and mixtures thereof. Another useful class of nonionic textile antistatic/softener materials include substantially water-insoluble compounds that are chemically classified as fatty alcohols.

Mono-ols, di-ols, and poly-ols having the requisite melting point and water-insoluble properties described above are useful in the present invention. Such alcohol-type textile conditioning substances also include mono- and di-fatty glycerides containing at least one free OH group.
All non-water soluble high melting alcohols (including mono- and -glycerides) are useful in the present invention since all such materials are textile compatible.

Of course, it is desirable to use such materials that are colorless so as not to change the color of the textiles being treated. Safe for use in contact with skin. It is necessary to select toxicologically acceptable materials5. Preferred types of non-esterified alcohols useful in the present invention include those with high melting points that are classified as so-called fatty alcohols.

Such alcohols are generally alcohols obtained from natural fats and oils, but the term monofatty alcohols refers to these alcohols that correspond to alcohols obtained from fats and oils, as well as all such alcohols produced by synthetic methods. has meant. Fatty alcohols produced by mild oxidation of petroleum products are useful in the present invention. Other forms that can be classified as alcohols and can be used as textile antistatic/softener materials in this invention include various esters of polyhydric alcohols.

An ester-alcohol substance having a melting point within the above range and being substantially water-insoluble may be used in combinations where the substance contains at least one free hydroxyl group, i.e. when the substance is as an alcohol. If it can be classified, it can be used in the present invention. Alcoholic di-esters of glycerol useful in the present invention include 1,3-di-glyceride and 1,3-di-glyceride.
Both 2-di-glycerides are included.

In particular, two C8-C in the molecule, preferably ClO-C
Diglycerides containing 18 alkyl groups are useful textile conditioning agents. Non-limiting examples of ester-alcohols useful in the present invention include glycerol-1,2
- dilaurylate, glycero-ru 1,3-dilaurate, glycero-ru 1,2-dimyristate, glycero-ru 1,3-dimyristate, glycero-ru 1,2-dimyristate
-dipalmitate, glycero-1,3-dipalmitate, glycero-1,2-distearate and glycero-1,3-distearate. Mixed glycerides obtained from mixed tallow alkyl fatty acids, namely 1,2-ditallow alkylglycerol and 1,3-ditallow alkylglycerol, are the ester-alcohols mentioned above that are economically attractive for use in the present invention. are preferred for use in the present invention because they are obtained from natural fats and oils. Mono- and di-ether alcohols having at least one free -0H group, especially di-ether alcohols of ClO-Cl8, are also included in the definition of alcohol class 3 useful as textile antistatic/softening agents in the present invention. Applies to.

The ether-alcohol can be prepared using the classical Williamson ether synthesis method. For this ether alcohol, the reaction conditions are chosen such that at least one free, unetherified -0H group remains in the molecule.
4 Ether alcohols useful in the present invention include glycero-1,2-dilauryl ether, glycero-1,
, 3-distearyl ether, and butane-tetraol-1,2,3-trioctanyl ether. The textile antistatic/softening agents described above can be used alone or as a mixture in combination with the imidazolinium compounds in the practice of this invention.

When present in the compositions of the invention, the agent will usually be about 1 to 12%, preferably about 1 to 12%, based on the weight of the composition.
Present in an amount ranging from about 8%. Preferred mixtures are mixtures of the quaternary imidazolinium salts with sorbitan esters, fatty alcohols, or quaternary ammonium compounds. The most preferred mixture is the quaternary imidazolinium salt and ditallow dimethylammonium chloride (DTD).
MAC). These two compounds are preferably about 80/20 to about 20/J8O, most preferably 30/70 to 70/30 imidazolinium/
The weight ratio of DTDMAC is used. Components of conventional liquid textile preparation compositions can be dissolved or dispersed in the composition. These conventional ingredients include clay materials, aldehyde preservatives, emulsifiers, thickeners, opacifiers, colorants, brighteners, fluorescent agents, PH modifiers, and perfumes. Such optional materials are generally included in amounts of about 0.01% to 10% based on the ingredients of the composition. Processing The aqueous textile conditioning composition of the present invention can be prepared using conventional techniques by adding the textile softening and antistatic agent to water.

For example, the drug can be heated to form a liquid oil phase, which can be added to hot water and mixed. Optional ingredients can be added by methods known in the industry. The composition is then brought to a pH of about 3 to about 9, preferably about 4.5 to 7.
Adjust the pH to . Use of the Composition The composition of the present invention is preferably used during the rinse cycle of a normal automatic washing operation.

Generally, the rinse water is at a temperature of about 15 to about 60<0>C. When the compositions of the present invention are added to the rinse cycle, the textile conditioner is generally present in an amount of about 2 to about 500 ppm, preferably about 10 to about 100 ppm.

Excellent textile softening and static suppression are achieved at such concentrations. Generally, textile products are prepared using the composition of the present invention through the following steps.

(a) a conventional automatic machine for washing textiles with a detergent composition (usually containing a detersive surfactant selected from the group consisting of anionic, nonionic, amphoteric or ampholytic surfactants, or mixtures thereof); (b) rinsing the textile; and (c) adding the above amount of textile conditioner during the rinsing stage of the operation.

Preferably, the final step (d) includes drying the textile in an automatic dryer at a temperature of at least about 38°C. This drying step facilitates the diffusion of the textile conditioning material of the present invention over the surface of the textile and is particularly useful in combinations using particulate sorbitan ester materials. The following examples illustrate the textile conditioning compositions of the invention as well as the advantages obtained using these compositions.

These examples are illustrative of the invention and are not intended to limit it. Example 1 An imidazolinium salt essentially free of amines, amine salts and propoxylated imidazolinium salts is prepared as follows.

A1 diethylene triamine and hardened tallow triglyceride are charged to the reactor at an amine/triglyceride molar ratio of about 1.4/1.

B1 The amine and triglyceride are allowed to react for 3 hours at a temperature of about 185° C. and normal pressure.

C. Reduce the pressure in the reactor to about 10 Tf$L mercury and maintain this condition for 2 hours.

The products at this point are the imidazoline intermediate for the desired imidazolinium salt and the primary and secondary amines from the unreacted and intermediate amide products. The reaction mixture is analyzed using conventional analytical techniques to determine the amount of imidazoline and primary and secondary amines. D1 The reactor is cooled to 80°C and isopropyl alcohol is added to the reactor in an amount corresponding to about 20% of the reactor contents.

This solvent serves to keep the reaction medium fluid. E1 propylene oxide is added to the reactor in an amount corresponding to about 2% of the imidazoline and unreacted materials.

This amount is sufficient to convert unreacted primary and secondary amines to propoxylated tertiary amines. F1 The reactor is maintained under vacuum pressure of about 10 T$L of mercury for 1 hour.

G1 Finally, an alkylating agent in the form of dimethyl sulfate is added to the propoxylation reaction mixture.

The amount of alkylating agent initially used is slightly less than the number of moles of imidazoline produced after step C above. As alkylation progresses, P of the reaction medium
Measure H and add additional dimethyl sulfate until the pH is in the range of 5-7. The product obtained in the above reaction is essentially free of amines and amine salts.
-Methyl-1-tallow-amidoethyl-2-tallow imidazolinium methyl sulfate.

Example 2 The following composition is manufactured.

The pH of both samples is adjusted to 5.8 using sodium hydroxide.

Compositions A and B after being maintained for one week at the temperatures listed below.
to determine the residual aldehyde.

The initial amount of aldehyde in the composition is 550 ppm.

The above numbers demonstrate the improved nurdehyde stability of imidazolinium essentially free of amines and amine salts.

Claims (1)

[Scope of Claims] 1. A composition for preparing textile products, which is characterized by containing a quaternary imidazolinium salt having the following structure. ▲There are mathematical formulas, chemical formulas, tables, etc.▼Here, R and R
_1 is an aliphatic or alicyclic hydrocarbon group having about 10 to about 22 carbon atoms, R_2 is an alkyl, substituted alkyl or aralkyl group having 1 to about 8 carbon atoms, and R_3 and R_4 is hydrogen, hydroxyl group, 1
~ short chain length alkyl having about 4 carbon atoms, or 1
~Hydroxy short chain length alkyl group with about 4 carbon atoms, D is H, ▲There are mathematical formulas, chemical formulas, tables, etc.▼
, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ and ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (where n is a number from 1 to about 6), X is an anion, and the composition comprises a total of less than about 4% primary based on the weight of the imidazolinium salt.
amines, secondary amines and cyclic tertiary amine salts. 2 the composition is in the form of an aqueous liquid and the imidazolinium salt is present in an amount from about 1 to about 15% by weight;
The composition of item 1 above. 3. The composition of paragraph 1 above, wherein R and R_1 are aliphatic or alicyclic hydrocarbon groups having from about 14 to about 20 carbon atoms. 4. The composition of paragraph 1 above, wherein R_3 and R_4 are hydrogen. 5. The composition of paragraph 1 above, wherein R and R_1 are derived from tallow fatty acids. 6. The composition of paragraph 1 above, wherein R_2 is methyl and X is methyl sulfate. 7 D is ▲ has a mathematical formula, chemical formula, table, etc. ▼, the concentration of the imidazolinium salt is about 2 to about 8% by weight, and the pH of the composition is about 4.5 to 7; Composition of item 1. 8 The concentration of the imidazolinium salt is from 2 to about 8% by weight, and the composition contains from about 1 to about 8% by weight of other organic textile conditioning agents that are free of primary amines, secondary amines, and cyclic tertiary amine salts. The composition of paragraph 1, further comprising an amount corresponding to about 12% by weight. 9. The composition of clause 8 above, wherein the additional textile conditioning agent is selected from the group consisting of aliphatic nonionic and cationic materials. 10. The composition of clause 9 above, wherein the additional textile conditioner is selected from the group consisting of quaternary ammonium compounds, fatty alcohols and sorbitan esters. 11. For the imidazolinium salt, D is ▲a mathematical formula, a chemical formula, a table, etc.▼, R_1 and R_2 contain 14 to 20 carbon atoms, and R_3 and R_4 are hydrogen, as described in item 10 above. Composition. 12. The composition of paragraph 11 above, wherein R and R_1 are tallow-based, R_2 is methyl, and X is methyl sulfate for the imidazolinium salt. 13 The additional textile conditioner is dimethyl ditallow ammonium chloride and the weight ratio of imidazolinium salt to dimethyl ditallow ammonium chloride is about 20/
80 to about 80/20.