JPH0819619B2 - Softener composition for textile products and method for softening textile materials using the same - Google Patents

Description

The present invention relates to a fabric softener composition containing a specific quaternary ammonium compound and a method for softening a fiber material using the same. More specifically, the present invention comprises two relatively long hydrophobic hydrocarbon groups and at least one ester group, which is derived from this compound by hydrolysis of the ester group. The present invention relates to a fabric softener composition containing a compound as a fiber softener, which is capable of imparting an ion property different from the above, and a method for softening a fiber material using the same.

Quaternary ammonium compounds containing two relatively long hydrophobic hydrocarbon groups, alkyl and / or alkenyl groups, are known per se and, inter alia, are often used as fungicides and fabric softeners. Are known. The most commonly used compound as a softening agent for textiles is di (hydrogen tallow alkyl) dimethylammonium chloride, which has a very good softening effect on textiles. However, quaternary ammonium compounds of this type, as well as the corresponding tertiary amines, are not always desirable from a biological point of view because they have a slow decomposition rate and have certain toxicity in various organisms in water.

The present invention relates to a textile softener composition containing a quaternary ammonium compound as a textile softener, which comprises two relatively long hydrophobic hydrocarbon groups and at least one ester group, and the same. The present invention relates to a method for softening a fiber material using a compound. By hydrolyzing the ester group to obtain a hydrolysis product, the nitrogen-containing compound can be given an ion property different from that of the original compound. It is a thing. The nitrogen-containing hydrolysis product is substantially less toxic to organisms in water than the original nitrogen-containing compound.

Thus, the present invention relates to a textile softener composition containing a quaternary ammonium compound defined in the claims and a method for softening a textile material using the same. The above compounds have the general formula: It is characterized by having.

In any of the quaternary ammonium compounds of formula (II), R in the formula is 13 to 22 (44 to 22 if the compound does not contain a group of A or other substituents) carbon atoms. Is a linear or branched alkyl or alkenyl group having R ₁ and R ₁ is an alkyl group having ₁ to 4 carbon atoms. Ester group: -C a (O) -O-R ₁ hydrolyzed to -C (O) -O ^- by a, it is possible to obtain a compound properties different as ions. The quaternary ammonium compound of formula (II) is cationic, and ester hydrolysis of this compound yields the corresponding betaine type structure, ie, the formula: Is obtained.

Therefore, the above compound can be used in a form that has the desired affinity for the substrate (this affinity for the substrate is believed to be due to the cation nature of the compound), Changes in pH after use can be converted to compounds that do not have cationic properties and are therefore considerably less toxic to aquatic organisms such as fish, Daphnia, algae and the like.

The compound of the formula (II) has a bactericidal effect and a conditioning effect by having two R groups which are relatively long linear or branched alkyl and / or alkenyl groups. This R
The group may be substituted to include a hydroxyl group as a substituent and optionally an ether bond. It is of course also possible for the R group to be a technical mixture of alkyl and / or alkenyl groups of various carbon atoms derived from natural products such as tallow, hydrogenated tallow, palm oil, palm kernel oil and the like. Another example of a very suitable natural product is rapeseed oil, which provides mainly fatty acid groups with C ₁₈ groups. R ₁ is an alkyl group having 1 to 4 carbon atoms, such as a methyl, ethyl, propyl or isopyropyr group. The hydrocarbon chain between the nitrogen and the ester group in the compounds of the present invention is the group: -CR'R ") _n- , where n is 1-4.
, R ′ and R ″ are each independently hydrogen, 1 to 3
Is a hydrocarbon-containing alkyl or hydroxyalkyl group, or a hydroxyl group. Group: − (CR ′
R ″) _n − may be a group substituted with an oxo group,
In that case, groups _{:-( CH 2 -C (O) -CH} 2) - and is suitable for groups :-( CR'R _{") n} - it is a straight-chain having 1 to 4 carbon atoms It is suitable to have an unsubstituted alkylene group or a group of this type substituted with an alkyl, hydroxyalkyl or hydroxyl group. Four
It is preferred to interpose a linear alkylene group having 4 carbon atoms, especially a methylene group. R ₂ is an alkyl or hydroxyalkyl group having 1 to 4 carbon atoms. R ₂ is suitably a methyl group or a hydroxyethyl group, preferably a methyl group. X is an anion. X can be any anion that does not adversely affect the effect of the compound when it is used for a particular purpose. Suitable anions include halides, especially chlorides and bromides, alkyl sulfates such as methyl sulfate and ethyl sulfate, alkyl phosphates such as dimethyl phosphate. Chloride ions are preferred as anions.

A in the quaternary ammonium compound represents a group containing an ester functional group or an amide functional group (m is 0 or 1) which may be present in the compound. When the compounds according to the invention contain a radical of A, they can contain one or two radicals of this kind. Group A can be any of the following four groups containing various ester functional groups or groups containing amide functional groups.

_{1) - (O-CH 2} -CHR) p -O-C (O) - (CH 2)
_{q -, 2) -C (O} ) O-CHR-CH 2 - (O-CHR-CH 2) P
-, 3) - (O- CH 2 -CHR) P -O-C (O) -O-CHR
_{-CH 2 - (O-CHR-} CH 2) P -, 4) -C (O) -O-CH 2 -C (OH) H-CH 2 - 5) -C (O) -NH- (CH 2 ) _Z -where R is hydrogen or a methyl group, p is 0-5,
q is 1 or 2 and z is 2 or 3, provided that the total number of alkylene oxide groups of the 3 type groups does not exceed 5.

By hydrolyzing a compound containing an ester group A with this ester group, a first decomposition of this compound can occur, resulting in a smaller structure. This degradation is important in terms of biodegradability. Where the compound contains groups of type 2, 3 or 4,
By hydrolysis with this ester group, the ester group:-
After hydrolysis with O—C (O) —R ₁ , there is no change in the charge properties of the resulting nitrogen-containing hydrolysis product. If the compound contains one type of A group, hydrolysis results in a hydrolysis product having an anionic charge. Therefore, when the compound contains an ester group A, this group is preferably of the type 2, 3 or 4. However, even when used as a type 1 group, anionic compounds are generally less toxic than cationic compounds and are therefore advantageous over the original cationic compounds. The quaternary ammonium compound may also include one A group that is an ester-containing group and one A group that includes an amide functional group. Examples of quaternary ammonium compounds containing a hydroxyl substituent have the formula: Wherein R _X is an alkyl or alkenyl group having 12 to 20 carbon atoms, especially R ′ and R ″ are hydrogen, n is 1, R ₁ and R ₂ and X is as defined above. Examples of quaternary ammonium compounds containing an ether linkage and a hydroxyl group include compounds of the formula: Wherein R is as defined above, especially R ′ and R ″ are hydrogen, n is 1, R ₁ and R ₂ and X
Are compounds as defined above. Examples of quaternary ammonium compounds containing A groups of type 5), ie amide functional groups, have the formula: Wherein R is as defined above, especially R ′ and R ″ are hydrogen, n is 1, R ₁ and R ₂ and X
Are compounds as defined above. Examples of quaternary ammonium compounds containing group A of type 4) include compounds of the formula: Wherein R is as defined above, especially R ′ and R ″ are hydrogen, n is 1, R ₁ and R ₂ and X
Are compounds as defined above.

However, from the viewpoint of production technology, economical efficiency, and efficiency in use, a compound containing no A group is preferable. For these reasons, the most preferred compounds are free of A groups,
It is a compound containing an unsubstituted R group.

It is particularly preferred that the compound contains a methyl group as the group for R ₁ , which in this case results in a faster hydrolysis of the compound, which results in a faster decrease in toxicity. This is because the. During the production of the compound, a certain amount of transesterification reaction occurs, and the product may contain R ₁ group derived from the solvent used, for example, isopropyl group or ethyl group. For example, by shortening the reaction time or lowering the temperature, it is possible to control the transesterification reaction and increase the yield of the product having the desired group. The reaction can also be carried out in an inert solvent, for example methyl ethyl ketone, in order to prevent the transesterification reaction. It is also possible to use a solvent which results in a transesterification reaction with the same R ₁ group in order to obtain the desired R ₁ group in the compound.

A tertiary amine represented by the same formula as the above formula (II) except that it does not contain an R ₂ group has the formula: [R- (A) _m ] ₂ NH and R, A, and a secondary amine in which m is as defined above and a formula: H ₂ C = CR ′ (CR′R ″) _o-2- COOR _{1 in} which R ′, R ″ and R ₁ are as defined above. It can be prepared by reaction with an alkyl ester of an unsaturated carboxylic acid, which is as defined. This reaction is from 50 ℃
It can be performed at a temperature of 150 ° C. for 12 to 48 hours. Suitably the reaction is carried out in a solvent selected from the group consisting of lower alcohols (eg ethanol and isopropanol), glycols, polyglycols and glycol ethers. For the above purposes, the tertiary amine can be used as it is or in the form of a salt.

Using the tertiary amine as an intermediate product, the above formula (I
The quaternary ammonium compound of I) can be produced. The tertiary amine may be quaternized with conventional quaternizing agents such as methyl chloride, methyl bromide, dimethyl sulfate, dimethyl sulfate to give the quaternary ammonium compound of formula II.

The quaternary ammonium compounds are also formula: [R- (A) _m] can also be prepared from ₂ NR ₂ tertiary amines, in that case, the tertiary amine of the formula: X- (CR ′ R ″) _n COOR ₁ , wherein R ₁ , R ′, R ″ and n are as defined above, and X is halogen, preferably chlorine, and an alkyl ester of haloalkanoic acid or substituted haloalkanoic acid. Quaternized by the reaction of. Suitable reaction conditions and solvents are those mentioned above for the reaction of secondary amines with alkyl esters of unsaturated carboxylic acids. However, the reaction time can usually be in the range of 2 hours to 24 hours. The method for producing an amine containing an ester group A is
It is well known to those skilled in the art. Typical examples of the production of the tertiary amine containing the above-mentioned A group include the reaction of methyliminodiacetic acid with a fatty alcohol for the A group of type 1) and the methyl group for the A group of type 2). Reaction of diethanolamine with fatty acids or fatty acid esters (eg methyl esters or triglycerides), and for group 3) A groups, there is reaction of methyldiethanolamine with fatty alkyl chloroformates.
The quaternary ammonium compound of formula (III) is obtained, for example, by reacting a lower alkylamine such as methylamine with an α-epoxide having a relatively long aliphatic group, and then
It can be produced by quaternizing the obtained tertiary amine with an alkyl ester of a haloalkanoic acid or a substituted haloalkanoic acid. The quaternary ammonium compound of formula (IV) is obtained by reacting a fatty alcohol with epichlorohydrin, then reacting the obtained reaction product with a lower alkylamine, and further adding an alkyl ester of haloalkanoic acid or substituted haloalkanoic acid. It can be produced by quaternization. To produce a quaternary ammonium compound of formula (V), for example, aminoethylethanolamine or diethylenetriamine is reacted with a fatty acid or fatty acid ester (eg methyl ester or triglyceride), and then the resulting reaction product is obtained. It is reacted with ethylene oxide and then quaternized with an alkyl ester of a haloalkanoic acid or a substituted haloalkanoic acid. In synthesizing the quaternary ammonium compound of the formula (VI), for example, epichlorohydrin is reacted with a fatty acid or a fatty acid ester (eg methyl ester or triglyceride), and then the obtained reaction product is converted into a lower amine. , For example, with methylamine and then quaternized with an alkyl ester of a haloalkanoic acid or a substituted haloalkanoic acid. A group substituted with an oxo group:
- (CR'R _{") n} -, preferably groups :-( CH ₂ -C
(O) -CH ₂₎ - quaternary ammonium compounds containing the dialkyl methyl amine, methyl-4-halo-3-oxo - can be prepared by reacting the butanoate. During the production of the amines and quaternary ammonium compounds of the present invention, some hydrolysis of the ester product formed may occur. However, it has been found that this does not impair the efficiency of using the product. As shown in the examples, 50 to 50 based on the dry matter in the reaction product.
Even when a considerably large amount of the hydrolysis product of 70% or less is present, the effect during use is not impaired. Thus, the compounds according to the invention can be used as prepared, that is to say in the reaction mixture obtained which contains the hydrolysis product. The invention also relates to the product reaction mixture prepared as described above. The obtained reaction mixture may contain an amine or a quaternary ammonium compound which does not contain the ester group as in the compound of the present invention. The presence of this type of compound does not adversely affect its effectiveness during use,
It goes without saying that it is desirable to suppress the amount of this type of compound so that the properties relating to the environment, that is, degradability and toxicity are as good as possible.

The present invention relates to a textile softener composition containing the quaternary ammonium compound of the formula (II) as a textile softener, and a method for softening a textile material using the same to treat a textile material. This is because the above compound has an excellent softening effect. The above compounds are used in the usual way when used as conditioning agents (textile softeners) for textile materials. That is, the softener for the above fiber material according to the present invention (the quaternary ammonium compound of the above formula (II))
Is usually added in the form of an aqueous solution or a water / solvent-containing composition (formulation) to the rinse water after washing in an amount corresponding to about 5 g or less of the active substance per 1 kg of dry fiber material, and for a relatively short time. Normally, it exerts its effect on the fiber material during the treatment for 5 to 10 minutes. The above compounds according to the present invention are suitably added as an aqueous composition having a pH value not exceeding 4.5 when used. The pH is suitably in the range of 2.0 to 4.5, preferably in the range of 2.5 to 4. The above compound according to the present invention, as described above,
At pH values in this range, it is essentially present in a form that has an affinity for the treated fiber material. When the used compound is discharged together with the wastewater, the desired ester hydrolysis proceeds, which leads to compounds with different ionic properties, which are advantageous in terms of toxicity.

The compound of formula (II) is incorporated into the softener composition of the present invention which is particularly suitable for use as a softener for textiles. Such compositions are formulations containing water and / or solvent, suitably containing the active compounds in an amount of 1% by weight or more. This composition comprises a relatively high amount of active substance, suitably about 50, in a solvent or a mixture of water and solvent.
It can also be a concentrated product containing from about 90% by weight.
The solvent as used herein mainly includes the above-mentioned inert or active solvents used in the production of the above-mentioned compounds, that is, lower alcohols (for example, ethanol and isopropanol), glycols, polglycols, and glycol ethers. Is a suitable solvent. The composition can also be a diluted product suitable for direct use. In this case, it is appropriate for the composition to contain an amount of 1 to about 40% by weight of the compounds described above to form an aqueous formulation, with a relatively small amount of solvent, preferably the solvents listed above, For example, it may be contained in an amount of 20% by weight or less based on the total amount of the active substance and water. It is suitable that the composition containing water or water and a solvent has the above-mentioned pH value so that the compound does not undergo substantial hydrolysis in the composition. When diluted with water, the pH is usually
Is less than 4.5. Mineral acids such as hydrochloric acid and sulfuric acid, and organic acids such as lactic acid, citric acid and benzoic acid can also be added to adjust the pH to the desired value. It is also possible to add other softeners known per se to water or a composition containing water and a solvent, and also to use additives commonly used for products of this type, such as emulsifiers and viscosity modifiers ( Of course, it is also possible to incorporate an inorganic electrolyte such as sodium chloride or calcium chloride), a dye, a fragrance, a foam suppressor, an optical brightening agent and the like.

The invention will be further described in the following examples. Parts and percentages refer to parts by weight and% by weight, respectively, unless otherwise stated.

Example 1 328 g of di (hydrogenated tallow alkyl) methylamine with a total amine number of 71.7 mg HCl / g was mixed with 135 g of isopropyl alcohol. The mixture was then heated to 90 ° C. and to this mixture was added 76 g of the methyl ester of monochloroacetic acid.
Added over time. Next, raise the temperature to about 100 ° C,
This temperature was maintained for 7 hours. The resulting product had a total amine number of less than 1 (original amine / isopropanol mixture had a total amine number of 50.9) and a dry solids content of
75.6%, 25.4% dialkyl betaine isopropyl ester, 20.0% dialkyl betaine methyl ester,
It contained 5.6% dialkylbetaine and 3.6% unreacted dialkylmethylamine.

Example 2 The softening effect of the reaction product obtained in Example 1 was measured by using a clean cotton terry towel, a dispersion of the reaction product in water, and di- (hydrogenated tallow alkyl) dimethylammonium chloride ( DHTDMAC) and evaluated. This dispersion is 0.5 per 1 kg of textile products.
It contained an amount of product corresponding to g of dry substance. The towel was treated for 5 minutes with stirring and then the towel was dried. A reference sample which was treated in the same manner as above except that it was treated only with pure water was also prepared.

Flexibility was evaluated on a scale of 0 to 5, with 5 representing the softest feel, and was performed on a panel of 12 people. The evaluation results given by the panel regarding the above treatment are as follows. Evaluation Value for Product Flexibility Example 1 5 DHTDMAC 5 Untreated Reference Example 0 From this example, the product of the invention is as flexible as the most popular commercial product, DHTDMAC. You can see that it has an effect.

Example 3 A part of the reaction product of Example 1 was dispersed in water so that the concentration of the dry substance was 5%, and the dispersion liquid was dispersed over 2 hours.
The hydrolysis was carried out by raising the pH to 10 and the temperature to 60 ° C. At this stage, the organic material containing dialkylbetaine and only traces of dialkylbetaine ester was extracted into the organic phase, separated, evaporated to dryness and diluted with isopropyl alcohol to 75% dry matter.

The product thus hydrolyzed is mixed with the reaction product as obtained in Example 1 in various ratios and these mixtures are made into dispersions in water and the procedure described in Example 2 gives a softening effect. Used to test. The case of DHTD MAC was also evaluated as a reference example. The results were as follows.

Given the inherent accuracy of this assessment method, no significant difference in flexibility was observed between the first four treatments of this study.

Example 4 60.8 g of di- (hydrogenated rapeseed oil alkyl) methylamine was mixed with 13.6 g of isopropyl alcohol in a closed container. Then, 12.9 g of methyl ester of monochloroacetic acid was added. The temperature was raised to 80 ° C. and kept constant for 24 hours. Whereas the original amine / isopropanol mixture had a total amine number of 51.0,
The total amine value of the reaction product was 2.1. The dry solid content of the obtained product was 84.9%, 14.6% dialkyl betaine isopropyl ester, 28.0% dialkyl betaine methyl ester, 9.8% dialkyl betaine,
And 5.4% unreacted dialkylmethylamine.

Example 5 Daphnia magna (Daphnia magna = Da) of the product of Example 4
Acute toxicity to phnia magna) was tested according to OECD Guideline No. 202, and the EC ₅₀ value at 48 hours was 10 pp.
m.

For comparison purposes, a 78% active sample of Gee (hydrogenated tallow alkyl dimethyl ammonium chloride), the most common source of softeners for textiles, was evaluated in the same test and found to have an EC ₅₀ value of 0.45 ppm for 48 hours. Met.

As is clear from the above, the toxicity of the product of the present invention is
It was about 20 times lower than DHTDMAC.

Example 6 680 g of di- (hydrogenated rapeseed oil alkyl) methylamine was mixed with 149 g of isopropyl alcohol in a closed vessel. Then 136 g of methyl ester of monochloroacetic acid was added. The temperature was raised to 80 ° C. and kept constant for 20 hours. The initial amine / isopropanol mixture had a total amine number of 54.5, whereas the reaction product had a total amine number of 3.4. When the reaction product was cooled and 123 g of isopropanol was added,
75.3% dry solids content, 16.0% dialkyl betaine isopropyl ester, 32.3% dialkyl betaine methyl ester, 4.5% dialkyl betaine, and
A product containing 2.7% unreacted dialkylmethylamine was obtained.

Example 7 The acute toxicity of the product of Example 6 to rainbow trout (Oncorhynchus mykiss) was determined by OECD.
When tested in a semi-static test (semi-static test) according to Guideline 202, the LC ₅₀ value at 96 hours is 19
It was as high as ppm.

In addition, the acute toxicity of the above product to green algae (Scenedesmus sudspicatus) was tested according to OECD Guideline No. 201.
The values of E _b C ₅₀ at 6 hours were 24 ppm (biomass) and _Er C ₅₀ (at 24 to 48 hours) were 33 ppm (growth amount), which were extremely good values.

Example 8 This example illustrates a simulation of primary decomposition.
An aqueous dispersion prepared from the reaction product of Example 6 and containing 0.5% dry solids was adjusted to pH 7 with a solution of potassium hydroxide, which was necessary to keep the pH constant. It was maintained using a pH stat apparatus with intermittent addition of as much potassium hydroxide solution. Take out samples at any time,
The relative amounts of dialkyl betaine and dialkyl betaine ester were measured. The results were as follows.

Example 9 This example demonstrates the preparation of a quaternary ammonium compound having an A group that contains an ester group. 105.8 g of a diester amine with a total amine number of 66.0, obtained by reacting 1 mol of methyldiethanolamine with 1.85 mol of tallow fatty acid, were mixed in a closed vessel with 48 g of isopropyl alcohol. Then 30 g of the methyl ester of monobromoacetic acid was added. Raise the temperature to 60 ° C and increase this temperature to 20
Held constant over time. At this point, another 0.6g
Was added to the methyl ester of monobromoacetic acid and the reaction was allowed to continue for 5 hours. The initial amine / isopropanol mixture had a total amine number of 45.4, while the reaction product had a total amine number of 3.6.

Example 10 This example illustrates the preparation of pure methyl ester quaternary ammonium compound. 83 g of di- (hydrogen tallow alkyl) methylamine with a total amine value of 71.6 mg HCl / g, 83 g
Of methanol. The mixture was then heated to 60 ° C. and 42 g of the methyl ester of monochloroacetic acid was added. The temperature was raised to about 90 ° C. and the reaction mixture was refluxed for 11 hours, after which another 2 g of methyl ester of monochloroacetic acid was added and the reaction mixture was refluxed for another 2 hours. The resulting product had a total amine number of 3.7, a dry solids content of 68.9%, 60.9% dialkylbetaine methyl ester, 2.5% dialkylbetaine, and 2.8%.
% Unreacted dialkylmethylamine.

Example 11 149 g of di- (hydrogenated tallow alkyl) methylamine with a total amine number of 71.6 mg HCl / g was mixed with 86 g of isopropanol. The mixture was then heated to 75 ° C. and 51.5 g of isopropyl ester of monochloroacetic acid was added. About temperature
Raised to 90 ° C. and the reaction mixture was refluxed for 6 hours.
The resulting product had a total amine number of 3.9 and contained 67.7% dialkylbetaine isopropyl ester and 3.0% unreacted dialkylmethylamine.

Example 12 The acute toxicity to Daphnia magna of the reaction mixtures obtained in Examples 10 and 11 was tested according to OECD Guideline No. 202 and the following results were obtained. Product 48-hour EC ₅₀ Example 10 7.0 ppm Example 11 0.75 ppm Example 13 The softening effect of the reaction mixtures obtained in Examples 10 and 11 was evaluated according to the procedure of Example 2. DH for reference
TDMAC was also evaluated at the same dose, ie 0.5 g dry solids per kg textile. The untreated reference example was also tested. The results were as follows. Evaluation Points for Product Flexibility Example 10 5 Example 11 5 DHTDMAC 5 Untreated Reference Example 0 Example 14 This example illustrates the preparation of a quaternary ammonium compound of formula (VI). 100.4 g of epoxide (84.1% active) obtained by reacting epichlorohydrin with an aliphatic alcohol having a chain of C _{16 to} C ₂₀ sold under the trade name of Alfol 1620 at 50 ° C. Heated to and flushed with nitrogen. 12.4 g of methylamine (33% solution in ethanol) was added slowly over 3 hours while maintaining the temperature at 45-60 ° C. Then change the temperature
The temperature was maintained at 60 ° C. for 4 hours, during which time an additional 0.22 g of methylamine (made up to 33%) was added and the reaction was continued for another 4.5 hours. The resulting reaction mixture contained the desired di- (3-alkoxy-2-hydroxypropyl) methylamine and had a total amine number of 42.1 mg HCl / g.

The reaction product obtained above 20 g was mixed with 5.8 g isopropanol and heated to 80 ° C., then 3.36
g of monochloroacetic acid methyl ester was added. The mixture was refluxed at 90 ° C. for 10 hours, after which an additional 0.26 g of the methyl ester of monochloroacetic acid was added and the resulting reaction mixture was refluxed for another 3 hours. The total amine value of the obtained reaction product was 3.6 mg HCl / g.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI Technical display location C07C 233/36 9547-4H 233/38 9547-4H

Claims (18)

[Claims] 1. The following formula II: [Wherein, R is a linear or branched alkyl or alkenyl group having 13 to 22 carbon atoms, and R ₁ is 1
Is an alkyl group having 4 carbon atoms, and n is 1 to
Is an integer of 4, R ′ and R ″ are each independently hydrogen, an alkyl or hydroxyalkyl group having 1 to 3 carbon atoms, or a hydroxyl group, m is 0 or 1, and A is an ester. a group containing a group or amide functional group containing a group, group: 1) - (O-CH 2 -CHR) p -O-C (O) - (CH 2)
_{q -, 2) -C (O} ) O-CHR-CH 2 - (O-CHR-CH 2) P
-, 3) - (O- CH 2 -CHR) P -O-C (O) -O-CHR
_{-CH 2 - (O-CHR-} CH 2) P -, 4) -C (O) -O-CH 2 -C (OH) H-CH 2 - or 5) -C (O) -NH- ( CH ₂ ) _z- (wherein R is hydrogen or a methyl group, p is 0 to 5, q
Is 1 or 2 and z is 2 or 3,
The total number of alkylene oxide groups in groups of type 3) does not exceed 5), R ₂ is an alkyl or hydroxyalkyl group having 1 to 4 carbon atoms and X is an anion]. A method for softening a fiber material, which comprises treating the fiber material with a softener composition for a fiber product containing a quaternary ammonium compound represented as a fiber softener. 2. The method of claim 1 wherein R'and R "are both hydrogen. 3. m is 0, or m is 1 and A
There group: -C (O) O-CHR -CH 2 - (O-CHR-CH 2) P
-, group _{:-( O-CH 2 -CHR) P} -O-C (O) -O-CHR
_{-CH 2 - (O-CHR-} CH 2) P - or a group: -C (O) -O-CH 2 -C (OH) H-CH 2 - claim 1, wherein which is a Or second
The method described in the section. 4. The method according to any _{one of} claims 1 to 3, wherein R ₁ is a methyl group, an ethyl group or an isopropyl group. 5. The method according to any one of claims 1 to 4, wherein R ₁ is a methyl group. 6. A process according to any of claims 1 to 5, characterized in that m is 0 and the radical R is an alkyl or alkenyl radical having 14 to 22 carbon atoms. 7. The softener composition for textiles contains the quaternary ammonium compound and water and / or a solvent,
The method according to any one of claims 1 to 6, wherein the content of the quaternary ammonium compound is 1% by weight or more. 8. The softener composition for the textile product has a p of 4.5 or less.
Method according to any of claims 1 to 7, characterized in that it has an H value. 9. The method of claim 8 wherein the fabric softener composition has a pH value in the range of 2.0 to 4.5. 10. The following formula II: [Wherein, R is a linear or branched alkyl or alkenyl group having 13 to 22 carbon atoms, and R ₁ is 1
Is an alkyl group having 4 carbon atoms, and n is 1 to
Is an integer of 4, R ′ and R ″ are each independently hydrogen, an alkyl or hydroxyalkyl group having 1 to 3 carbon atoms, or a hydroxyl group, m is 0 or 1, and A is an ester. a group containing a group or amide functional group containing a group, group: 1) - (O-CH 2 -CHR) p -O-C (O) - (CH 2)
_{q -, 2) -C (O} ) O-CHR-CH 2 - (O-CHR-CH 2) P
-, 3) - (O- CH 2 -CHR) P -O-C (O) -O-CHR
_{-CH 2 - (O-CHR-} CH 2) P -, 4) -C (O) -O-CH 2 -C (OH) H-CH 2 - or 5) -C (O) -NH- ( CH ₂ ) _z- (wherein R is hydrogen or a methyl group, p is 0 to 5, q
Is 1 or 2 and z is 2 or 3,
The total number of alkylene oxide groups in groups of type 3) does not exceed 5), R ₂ is an alkyl or hydroxyalkyl group having 1 to 4 carbon atoms and X is an anion]. A softener composition for a textile product, which comprises the quaternary ammonium compound represented as a fiber softener. 11. A method according to claim 10 wherein R'and R "are both hydrogen. 12. M is 0, or m is 1 and A is a group: --C (O) O--CHR--CH _2- (O--CHR--CH ₂ ) _P.
-, group _{:-( O-CH 2 -CHR) P} -O-C (O) -O-CHR
_{-CH 2 - (O-CHR-} CH 2) P - or a group: -C (O) -O-CH 2 -C (OH) H-CH 2 - item 10 claims, which is a Or the eleventh
The composition according to the item. 13. A method according to claim 10, wherein R ₁ is a methyl group, an ethyl group or an isopropyl group.
The composition according to any of the items. 14. The composition according to any one of claims 10 to 13, wherein R ₁ is a methyl group. 15. The composition according to claim 10, wherein m is 0 and the R group is an alkyl or alkenyl group having 14 to 22 carbon atoms. . 16. The softener composition for a textile product contains the quaternary ammonium compound and water and / or a solvent, and the content of the quaternary ammonium compound is 1% by weight or more. The composition according to any one of claims 10 to 15. 17. The composition according to claim 10, wherein the fabric softener composition has a pH value of 4.5 or less. 18. The fabric softener composition comprising 2.0 to 4.5
Claim 17 characterized in that it has a pH value in the range of
The composition according to the item.