KR20120026325A - A manufacturing method of softening agent for fabrics using antioxidants - Google Patents

Abstract

PURPOSE: A method for manufacturing fiber softener using antioxidant is provided to shorten processing time and to ensure excellent effect in spite of a small amount of a catalyst and adjuvant. CONSTITUTION: A method for manufacturing fiber softener using antioxidant comprises: a step of reacting oil containing fatty acid and tertiary hydroxyalkyl amine using alkali catalyst and phosphorus antioxidant to prepare fatty acid hydroxyl alkyl amine ester; and a step of reacting the fatty acid hydroxyl alkyl amine ester with quarternizing agent in low molecular alcohol solvent.

Description

A manufacturing method of softening agent for fabrics using antioxidants

The present invention relates to a method for preparing a fabric softener using an alkali catalyst and a phosphorus antioxidant.

The most commonly used fabric softener is esterquat, an ester salt of quaternary fatty acid triethanolamine, synthesized from ecotoxically safe raw materials. Since the fiber is negatively charged in water, it adsorbs cationic ester quarts to form a charged film on the surface of the fiber, thereby adsorbing moisture to prevent charging. Cationic fiber softeners are adsorbed in the water so that hydrophilic groups are toward the negatively charged fibers and lipophilic groups are directed toward the outside of the fibers, and the surface of the fibers is coated with a thin film of oil, making the fibers free to move and swell, creating a softening effect. do.

As the price of fatty acid, a raw material of ester quart, continues to rise, many researches have been conducted to prepare ester quart compounds through transesterification by directly reacting oils with amines. Lags in conversion The prior art for improving this is as follows.

In U.S. Patent No. 5,637,743, a transesterification reaction is carried out using sodium methoxide as an alkali catalyst to partially hydrogenated palm oil and triethanolamine, followed by dimethyl sulfate. It is quaternized with (dimethylsulfate), and also shows an example of transesterification reaction using hypophosphorous acid as a catalyst in a mixture of dimethylaminopropylamine and triethanolamine.

U.S. Patent No. 5,869,716 discloses methods for producing ester quarts directly from natural fats or oils to reduce the color and reaction time of the product as sodium borohydride and hypophosphorous acid as catalysts. Sodium hypophosphite was used in an amount of 0.05 wt% to 0.1 wt%, triethanolamine, diethanol methylamine, 1,2-dihydroxypropyl dimethylamine, Or a mixture of these amines was transesterified with oil.

U.S. Patent Nos. 6,906,025 and 7,001,879 relate to softeners used in automatic dryers, wherein the quaternary ammonium salts are used as sodium borohydride, or hydrogenation, as a catalyst in the transesterification of oils and amines in the form of triglycerides. Sodium boron and calcium hydroxide (calcium hydroxide) was used in combination.

However, since the alkali / alkaline earth metal borohydride-based catalyst is expensive, there is a problem of unit price increase in the preparation of the cationic fiber softener using the same.

Korean Patent No. 861,699 transesterifies a fatty acid-containing oil with a tertiary hydroxyalkylamine under a specific ratio of an alkali main catalyst and a sodium hypophosphite subcatalyst, and the fatty acid hydroxyalkylamine ester is quaternized in a low molecular alcohol solvent. As a method of reacting with a topical agent, there is a problem in that it is still very economical but lacks in color, conversion rate and long-term stability of triglyceride.

Therefore, the present inventors have studied to overcome the above problems, and when the phosphorus (P) -based antioxidant is used as an alkali catalyst and an auxiliary agent in the preparation of the fabric softener, the color is excellent, the triglyceride conversion and the stability of hydrolysis is high, In addition, it has been found that an economical fabric softener excellent in flexibility and water absorption can be prepared, and the present invention has been completed.

Therefore, the present invention is to provide a method for producing a fabric softener that can obtain an ester quart of a quaternary ammonium salt at high conversion even without changing the color even at high temperature.

In another aspect, the present invention is to provide a fabric softener prepared through the manufacturing method as its second object.

The present invention comprises the steps of: (a) using an alkali catalyst and a phosphorus antioxidant as an adjuvant, reacting an oil containing fatty acids with a tertiary hydroxyalkylamine to obtain a fatty acid hydroxyalkylamine ester; And (b) reacting the fatty acid hydroxyalkylamine ester obtained above with a quaternizing agent in a low molecular alcohol solvent to obtain a fiber softener comprising at least one ester quart selected from compounds represented by the following Chemical Formulas 1 to 3. It relates to a method for producing a fabric softener, characterized in that.

[Formula 1]

In Formula 1, R ₁ is a linear or branched alkyl or alkenyl group having 6 to 22 carbon atoms; R ₂ and R ₃ are independently of each other hydrogen or R ₁ CO; R ₄ is an alkyl group having 1 to 4 carbon atoms or a (CH ₂ CH ₂ O) _q H group; m, n and p are integers from 0 to 12, q is an integer from 1 to 12; X is a halide, alkyl sulfate or alkyl phosphate.

[Formula 2]

In Chemical Formula 2, R ₁ , R ₂ , m, n, and X are as defined in Chemical Formula 1, and R ₄ and R ₅ are each independently an alkyl group having 1 to 4 carbon atoms.

(3)

In Chemical Formula 3, R ₁ , R ₂ , R ₄ , m, n, and X are as defined in Chemical Formula 1, and R ₆ and R ₇ are each independently an alkyl group having 1 to 4 carbon atoms.

In another aspect, the present invention comprises 20 to 90% by weight of at least one ester quart selected from the compound represented by the formula (1) to (3) and 10 to 80% by weight of glycerin, glyceryl ester or a mixture thereof The present invention relates to a fabric softener.

The fabric softener prepared according to the present invention has an advantage that the color of the fabric softener is improved, the conversion rate is high, and excellent long-term stability, compared to the fabric softener prepared by the conventional method. In addition, the catalysts and auxiliaries used in the present invention can shorten the process time, have an advantage of exhibiting excellent effects even in small amounts, and are also inexpensive compared to the conventional sodium borohydride catalysts used to have excellent colors. It is economical in manufacturing cost. Therefore, the manufacturing method according to the present invention can be usefully used to prepare a fabric softener.

The present invention comprises the steps of: (a) using an alkali catalyst and a phosphorus antioxidant as an adjuvant, reacting an oil containing fatty acids with a tertiary hydroxyalkylamine to obtain a fatty acid hydroxyalkylamine ester; And (b) reacting the fatty acid hydroxyalkylamine ester obtained above with a quaternizing agent in a low molecular alcohol solvent to obtain a fibrous softener comprising at least one ester quart selected from compounds represented by the following formulas (1) to (3). It provides a method for producing a fabric softener, characterized in that.

[Formula 1]

In Formula 1, R ₁ is a linear or branched alkyl or alkenyl group having 6 to 22 carbon atoms, preferably 16 to 18 carbon atoms; R ₂ and R ₃ are independently of each other hydrogen or R ₁ CO; R ₄ is an alkyl group having 1 to 4 carbon atoms or a (CH ₂ CH ₂ O) _q H group; m, n and p are integers from 0 to 12, q is an integer from 1 to 12; X is a halide, alkyl sulfate or alkyl phosphate.

[Formula 2]

In Chemical Formula 2, R ₁ , R ₂ , m, n, and X are as defined in Chemical Formula 1, and R ₄ and R ₅ are each independently an alkyl group having 1 to 4 carbon atoms.

(3)

In Chemical Formula 3, R ₁ , R ₂ , R ₄ , m, n, and X are as defined in Chemical Formula 1, and R ₆ and R ₇ are each independently an alkyl group having 1 to 4 carbon atoms.

Hereinafter, the present invention will be described in detail step by step.

First, step (a) is a step of transesterifying an oil containing fatty acid with a tertiary hydroxyalkylamine using an alkali catalyst and a phosphorus antioxidant as an auxiliary agent to obtain a fatty acid hydroxyalkylamine ester. At this time, the adjuvant may also use a combination of a phosphorus antioxidant and a phosphorus reducing agent.

In the step (a) of the present invention, the oil containing a fatty acid used as a raw material is a vegetable or animal oil, it is preferable that the carbon number of the saturated or unsaturated hydrocarbon is 6 to 22, more preferably 16 to 18 carbon atoms It is good to use that. It consists of a mixture of monoglyceride, diglyceride and triglyceride forms, of which triglyceride forms predominantly.

At this time, the oil containing fatty acid is saturated or unsaturated bee tallow oil, palm oil, palm kernel oil, palm stearine oil, palm olein Oil (palm olein oil), coconut oil (coconut oil), olive oil (olive oil), rapeseed oil, sunflower oil (sunflower oil), cottonseed oil, soybean oil (soyabean oil) It can be used and these can be used 1 type or in mixture of 2 or more types. The degree of unsaturation of the oil containing the fatty acid is preferably between 0 and 70. The degree of unsaturation is expressed in grams of iodine per 100 g of fatty acid, also referred to as iodine number.

The hydroxyl group of the tertiary hydroxyalkylamine used in step (a) according to the present invention causes a transesterification reaction with the fatty acid in the oil containing the fatty acid. The tertiary hydroxyalkylamine used at this time can use diethanol methylamine, 1,2-dihydroxypropyl dimethylamine, triethanolamine, etc., These can be used 1 type or in mixture of 2 or more types.

In the step (a) according to the present invention, the reaction molar ratio of the fatty acid and the tertiary hydroxyalkylamine of the oil containing the fatty acid is preferably 1 to 2.5: 1. If the reaction molar ratio of the fatty acid and the tertiary hydroxyalkylamine of the oil containing the fatty acid is less than 1: 1, the amount of fatty acid converted from the oil is relatively small, resulting in a softening effect. In addition, when the reaction molar ratio exceeds 2.5: 1, the ester form of the fatty acid hydroxyalkylamine ester is relatively increased, resulting in a large amount of scum during emulsification.

In the present invention, the alkali catalyst is used as a catalyst, for example sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate anhydrous and anhydrous potassium carbonate carbonate anhydrous) and the like, and these may be used alone or in combination of two or more thereof.

The alkali catalyst is preferably added in an amount of 0.01 to 0.1 parts by weight, and more preferably 0.01 to 0.05 parts by weight, based on 100 parts by weight of the total weight of the oil containing the fatty acid and the tertiary hydroxyalkylamine. do. If the addition amount of the alkali catalyst is less than 0.01 parts by weight, the content of unconverted triglyceride oil is high, and if it exceeds 0.1 parts by weight, the color of the fabric softener is not good.

In addition, in the present invention, a phosphorus antioxidant alone or a combination of a phosphorus antioxidant and a phosphorus reducing agent may be used as an adjuvant, and the adjuvant improves reactivity in the transesterification reaction and improves the color of the resulting fatty acid hydroxyalkylamine ester. To be added. Phosphorus-based antioxidants that exhibit excellent effects on color stabilization in high temperature organic reactions include tetraphenyl dipropyleneglycol diphosphite (hereinafter referred to as JPP) and poly (dipropyleneglycol) phosphite. : Hereinafter referred to as DHOP), tris (2,4-di-tert-butylphenyl) diphosphite (Tris (2,4-di-tert-butylphenyl) diphosphite), distearyl pentaerythritol diphosphite (Distearyl pentaerythritol diphosphite) and diisodecyl phenyl phosphite may be used, and these may be used alone or in combination of two or more thereof. As the phosphorus reducing agent, sodium hypophosphite or hypophosphorous acid may be used.

The amount of these auxiliaries added is preferably 0.01 to 0.1 parts by weight, more preferably 0.05 to 0.1 parts by weight, based on 100 parts by weight of the total weight of the oil containing the fatty acid and the tertiary hydroxyalkylamine. . If the amount of the added auxiliary agent is less than 0.01 parts by weight, there is a problem in the color of the fabric softener, and if it exceeds 0.1 parts by weight, there is a problem of precipitation as a residue in the product. When the phosphorus antioxidant and the phosphorus reducing agent are mixed, the mixing ratio thereof is preferably 3: 1 to 1: 3 because mixing does not affect the color change.

Transesterification reaction of step (a) according to the present invention is preferably carried out at 160 ~ 240 ℃, more preferably 160 ~ 220 ℃, the reaction time is preferably 1 to 12 hours, more preferably It may be performed for 3 to 8 hours. If it is out of the above range may cause problems in the color and conversion rate of the product.

Performing step (a) according to the present invention, a fatty acid hydroxyalkylamine ester is obtained as a result of the transesterification reaction of the tertiary hydroxyalkylamine with a fatty acid moiety in an oil comprising a fatty acid. Depending on the progress of the esterification reaction, the following residues may remain.

First, when the fatty acids of the oil are all converted to fatty acid hydroxyalkylamine esters by transesterification with tertiary hydroxyalkylamine, glycerin remains as a residue, and when partially converted, a compound of the glyceryl ester form This remains.

In step (b), the fatty acid hydroxyalkylamine ester obtained in step (a) is reacted with a quaternizing agent in a low molecular alcohol solvent to obtain a fiber softener including ester quarts.

In the quaternization reaction of step (b) according to the present invention, the reaction molar ratio of the fatty acid hydroxyalkylamine ester and the quaternization agent is preferably 1.0: 0.9 to 1.0, and if the quaternization agent is 0.9 molar ratio or less, the unreacted product Scum occurs due to relative increase, there is a problem in emulsification, and if the quaternization agent exceeds 1.0 molar ratio, the pH and pH of the product are too low, and the unreacted quaternizing agent remains, resulting in poor stability and color of the product. there is a problem.

As the quaternizing agent used in step (b) according to the present invention, a dialkyl sulfate such as alkyl halide or dimethyl sulfate, such as methyl chloride, may be used. It is preferable, and these can be used individually or in mixture.

The low molecular alcohol solvent used in the step (b) according to the present invention means an alcohol solvent having 1 to 6 carbon atoms, for example, isopropyl alcohol, ethanol, propylene glycol , Dipropylene glycol may be used alone or in combination.

The quaternization reaction of step (b) according to the present invention may preferably be carried out at 50 to 80 ℃, more preferably 50 to 60 ℃, the reaction time is preferably 1 to 24 hours, more preferably May be performed for 2 to 8 hours.

Thereafter, the method may further include adding sodium chlorite and hydrogen peroxide to improve the color of the fabric softener. At this time, the addition amount of sodium chlorite and hydrogen peroxide is preferably 0.05 ~ 1.0% of the total weight of the fabric softener obtained through the above process, wherein the mixing ratio of sodium chlorite and hydrogen peroxide is 1: 3 to 1: 10 to use. good. If the addition amount of sodium chlorite and hydrogen peroxide is less than 0.05%, there is no color improving effect, and if it exceeds 1.0%, no further color improvement is obtained.

Finally, the preparation method according to the present invention using a phosphorus antioxidant or a combination of phosphorus antioxidant and phosphorus reducing agent as an alkali catalyst and auxiliaries is at least one ester quart (acyloxyalkyl) selected from the compounds represented by Formulas 1 to 3 Quaternary ammonium compound) 20 to 90% by weight, and a fiber softener comprising 10 to 80% by weight of glycerin, glyceryl ester or a mixture thereof.

The fabric softeners produced by the process according to the invention have an improved color (see Table 1), less residual oil content (see Table 2) and superior to the fabric softeners produced by conventional methods. Long-term stability (see Table 3).

Hereinafter, the present invention will be described in detail by way of examples. However, the following Examples are only for exemplifying the present invention, and the contents of the present invention are not limited by the following Examples.

< Example  1> Fabric softener  Produce

(1) transesterification reaction

Palm stearin oil (composition: C16 & others: 63%, C18: 5.1%, C18-1,2: 31.9) %) 566 g, triethanolamine 184.4 g, sodium hydroxide 0.23 g (0.03 parts by weight) and antioxidant JPP 0.19 g (0.025 parts by weight) are added. While injecting nitrogen at a rate of 250 ml / min using a bubble tube at the bottom of the reactor, the mixture was stirred at 250 to 300 rpm. The temperature of the reactant was raised to 160 ° C. for 1 hour to remove water contained in the raw material, and maintained at the temperature for 2 hours. The hydroxyalkylamine ester was obtained.

(2) quaternization

100 g of isopropyl alcohol was added to 10% of the total amount to the fatty acid hydroxyalkylamine ester obtained in the above (1), and the dry solid content was about 90%. Then, 150 g of dimethyl sulfate, a quaternizing agent, was slowly dropped dropwise, and a quaternization reaction was performed at 50 to 60 ° C. for 6 hours to prepare a fiber softener.

< Example  2> Fabric softener  Produce

(1) transesterification reaction

A fatty acid hydroxyalkylamine ester was obtained by the same method as the method of (1) of Example 1, except that 0.38 g (0.05 parts by weight) of antioxidant DHOP was added to the reactor.

(2) quaternization

Reaction was carried out in the same manner as in (2) of Example 1 to prepare a fabric softener.

< Example  3> Fabric softener  Produce

A fibrous softener was prepared in the same manner as in Example 1, except that 0.19 g (0.025 parts by weight) of phosphorus-based reducing agent and 0.19 g (0.025 parts by weight) of phosphorus antioxidant JPP were added as an adjuvant.

< Example  4> Fabric softener  Produce

A fiber softener was prepared in the same manner as in Example 1 except that 0.19 g (0.025 parts by weight) of phosphorus reducing agent sodium hypophosphite and 0.19 g (0.025 parts by weight) of phosphorus antioxidants were mixed as an adjuvant.

< Example  5> Fabric softener  Produce

A fiber softener was prepared in the same manner as in Example 1, except that 0.19 g (0.025 parts by weight) of phosphorus-based reducing agent and 0.19 g (0.025 parts by weight) of phosphorus-based antioxidant DHOP were mixed as an adjuvant.

< Example  6> Fabric softener  Produce

A fiber softener was prepared in the same manner as in Example 1, except that 0.19 g (0.025 parts by weight) of phosphorus reducing agent sodium hypophosphite and 0.19 g (0.025 parts by weight) of phosphorus antioxidant DHOP were mixed as an adjuvant.

< Comparative example  1> Fabric softener  Produce

A fibrous softener was prepared in the same manner as in Example 1, except that 0.19 g (0.025 parts by weight) of reducing hypophosphoric acid alone was added as an adjuvant.

< Comparative example  2> Fabric softener  Produce

A fibrous softener was prepared in the same manner as in Example 1, except that 0.19 g (0.025 parts by weight) of reducing sodium hypophosphate alone was added as an adjuvant.

< Experimental Example  1> Fabric softener  Color measurement

In order to find out how the color of the fabric softener used in combination of the alkali catalyst and the phosphorus reducing agent and the phosphorus antioxidant as an auxiliary agent according to the present invention was improved.

The color of the fatty acid hydroxyalkylamine ester produced after the transesterification reaction according to Examples 1 to 6 and Comparative Examples 1 to 2 was measured at 45 ° C. using a colorimetric system (Nippon Denshoku, OIL1) to measure the color (Gardner). , The measurement results are shown in Table 1 below.

division catalyst Supplements Color Chart Example 1 NaOH JPP 2.2 Example 2 NaOH DHOP 2.0 Example 3 NaOH H ₃ PO ₂ JPP
(1: 1) 2.4 Example 4 NaOH NaH ₂ PO ₂ JPP
(1: 1) 2.5 Example 5 NaOH H ₃ PO ₂ DHOP
(1: 1) 2.3 Example 6 NaOH NaH ₂ PO ₂ : DHOP
(1: 1) 2.4 Comparative Example 1 NaOH H ₃ PO ₂ 2.6 Comparative Example 2 NaOH NaH ₂ PO ₂ 2.7

As shown in Table 1, the fabric softener prepared by combining an alkali catalyst and a phosphorus antioxidant or a phosphorus reducing agent according to the present invention has a color of 2.0 to 2.5 Gardner, compared to Comparative Examples 1 to 2 using a conventional alkali catalyst ( 2.6 ~ 2.7 Gardner) It has a bright color and can be used as a fabric softener.

< Experimental Example  2> unconverted Triglyceride  Oil content measurement

In order to determine the content of unconverted triglyceride oil remaining in the fiber softener reacted by combining an alkali catalyst and a phosphorus antioxidant or a phosphorus reducing agent according to the present invention, the following experiment was performed.

The unconverted triglyceride oil content after the transesterification reaction according to Examples 1 to 6 and Comparative Examples 1 to 2 was measured using gas chromatography (Agilent, HP-7890A), and the measurement results are shown in Table 2 below. Shown in

Unconverted Triglyceride Oil Content division catalyst Supplements Primary reactant
Triglyceride content
GC Analysis (%) Example 1 NaOH JPP 1.90 Example 2 NaOH DHOP 1.80 Example 3 NaOH H ₃ PO ₂ JPP
(1: 1) 1.30 Example 4 NaOH NaH ₂ PO ₂ JPP
(1: 1) 1.50 Example 5 NaOH H ₃ PO ₂ DHOP
(1: 1) 2.24 Example 6 NaOH NaH ₂ PO ₂ : DHOP
(1: 1) 1.74 Comparative Example 1 NaOH H ₃ PO ₂ 3.28 Comparative Example 2 NaOH NaH ₂ PO ₂ 5.40

As shown in Table 2, the fiber softener prepared by combining the alkali catalyst and the phosphorus antioxidant or the phosphorus reducing agent according to the present invention has an unconverted triglyceride oil content of 1.3 to 2.24% as compared to the comparative example (3.8 to 5.4%), the conversion rate is high. Therefore, it can be seen that the method using a combination of an alkali catalyst and a phosphorus antioxidant or a phosphorus reducing agent according to the present invention is useful for preparing a fabric softener.

< Experimental Example  3> pH , Viscosity and long-term stability measurements

After emulsifying the fibrous softener reacted by combining an alkali catalyst and a phosphorus antioxidant or a phosphorus reducing agent according to the present invention by the following method, the following experiments were carried out to determine the viscosity and degree of long-term stability of the emulsion.

500 ml, four-necked glass reactor equipped with a stirring device capable of controlling the rotation speed, a cooler, 40 g each of the fabric softener prepared according to Examples 1 to 6 and the fiber softener prepared in Comparative Examples 1 to 2 (total 8.0% of the amount was prepared, and 440.9 g (88.18%) of water, 1 g (0.2%) of polyethylene lauryl ether, and 15 g of ethyleneglycol were added thereto and mixed. At this time, the speed of the reaction stirrer was fixed at 250 ~ 300 rpm and the temperature was raised to 50 ~ 60 ℃, and stirred for 1 hour. After stirring, the reaction solution was cooled to 30 ° C., 0.12% of dye (0.1% Soln.), 0.5% of fragrance, and a small amount of organic acid were added, followed by stirring for about 30 minutes to prepare an emulsion. The pH, viscosity and long term stability of the prepared emulsion were measured as follows.

[Measuring conditions]

pH: The prepared emulsion was measured for pH using a pH meter (ACCUMET BASIC).

Viscosity: The viscosity of the prepared emulsion was measured at 25 ° C. using a viscometer (Brookfield, LVDV II + PRO).

Long-term stability: The prepared emulsion was placed in an oven at 50 ° C. and the date until separation of the emulsion occurred was measured weekly.

The measurement results are shown in Table 3 below.

Properties of Emulsion division   content(%) pH Viscosity
(cPs) long time
stability
(week) fiber
Softener Spices Polyethylene
Glycol
Lauryl ether dyes
(0.1% Soln.) water 50 ℃ Example 1 8 0.5 0.2 0.12 88.18 3.47 182 24 Example 2 8 0.5 0.2 0.12 88.18 3.47 238 24 Example 3 8 0.5 0.2 0.12 88.18 3.24 207 23 Example 4 8 0.5 0.2 0.12 88.18 3.29 237 24 Example 5 8 0.5 0.2 0.12 88.18 3.36 238 24 Example 6 8 0.5 0.2 0.12 88.18 3.44 268 24 Comparative Example 1 8 0.5 0.2 0.12 88.18 2.98 229 22 Comparative Example 2 8 0.5 0.2 0.12 88.18 3.13 249 22

As shown in Table 3, the fabric softener prepared in accordance with the present invention has a stability of 23 to 24 weeks according to the long-term stability measurement, so that the stability is 1 to 2 than when using an alkali catalyst and phosphoric acid or sodium hypophosphate It can be seen that the state is superior.

Claims (17)

(a) reacting an oil comprising fatty acid with a tertiary hydroxyalkylamine using an alkali catalyst and a phosphorus antioxidant as an adjuvant to obtain a fatty acid hydroxyalkylamine ester; And
(b) reacting the obtained fatty acid hydroxyalkylamine ester with a quaternizing agent in a low molecular alcohol solvent to obtain a fiber softener comprising at least one ester quart selected from compounds represented by the following formulas (1) to (3):
Method for producing a fabric softener, comprising:
[Formula 1]

In Formula 1, R ₁ is a linear or branched alkyl or alkenyl group having 6 to 22 carbon atoms; R ₂ and R ₃ are independently of each other hydrogen or R ₁ CO; R ₄ is an alkyl group having 1 to 4 carbon atoms or a (CH ₂ CH ₂ O) _q H group; m, n and p are integers from 0 to 12, q is an integer from 1 to 12; X is a halide, alkyl sulfate or alkyl phosphate.
(2)

In Chemical Formula 2, R ₁ , R ₂ , m, n, and X are as defined in Chemical Formula 1, and R ₄ and R ₅ are each independently an alkyl group having 1 to 4 carbon atoms.
(3)

In Chemical Formula 3, R ₁ , R ₂ , R ₄ , m, n, and X are as defined in Chemical Formula 1, and R ₆ and R ₇ are each independently an alkyl group having 1 to 4 carbon atoms.
The method of manufacturing a fabric softener according to claim 1, wherein a combination of a phosphorus antioxidant and a phosphorus reducing agent is used as the adjuvant.
According to claim 1 or 2, wherein the oil containing the fatty acid of step (a) is saturated or unsaturated bee tallow oil (palm oil), palm oil (palm oil), palm kernel oil (palm kernel oil), Palm stearine oil, palm olein oil, coconut oil, coconut oil, olive oil, rapeseed oil, sunflower oil, sunflower oil, cottonseed oil Cottonseed oil) and soybean oil (soyabean oil) A method for producing a fabric softener, characterized in that one or two or more selected from the group consisting of.
The tertiary hydroxyalkylamine of claim 1 or 2, wherein the tertiary hydroxyalkylamine of step (a) is selected from the group consisting of diethanolmethylamine, 1,2-dihydroxypropyldimethylamine and triethanolamine, or A method for producing a fabric softener, characterized in that it is a mixture of two or more kinds.
The method according to claim 1 or 2, wherein the reaction molar ratio of the fatty acid of the oil containing the fatty acid of step (a) and tertiary hydroxyalkylamine is 1 to 2.5: 1.
The fibrous softener according to claim 1 or 2, wherein the alkali catalyst of step (a) is at least one selected from the group consisting of sodium hydroxide, potassium hydroxide, calcium hydroxide, anhydrous sodium carbonate and anhydrous potassium carbonate. Manufacturing method.
The alkali catalyst according to claim 1 or 2, wherein the alkali catalyst of step (a) is used in an amount of 0.01 to 0.1 parts by weight based on 100 parts by weight of the total weight of the oil containing the fatty acid and the tertiary hydroxyalkylamine. Method for producing a fabric softener.
According to claim 1 or 2, wherein the phosphorus antioxidant of step (a) is tetraphenyl dipropylene glycol diphosphite, poly (dipropylene glycol) phenyl phosphite, tris (2,4-di- tert-butyl-butyl A phenyl) diphosphite, distearyl pentaerythritol diphosphite and diisodecyl phenyl phosphite, any one or a mixture thereof.
3. The method of claim 2, wherein the phosphorus reducing agent is hypophosphorous acid or sodium hypophosphate.
The method of claim 1 or 2, wherein the auxiliary agent is used in an amount of 0.01 to 0.1 parts by weight based on 100 parts by weight of the total weight of the oil containing the fatty acid and the tertiary hydroxyalkylamine. .
The method of claim 1 or 2, wherein the reaction of step (a) is carried out at 160 to 240 ° C for 1 to 12 hours.
The method according to claim 1 or 2, wherein the reaction molar ratio of the fatty acid hydroxyalkylamine ester of the step (b) and the quaternizing agent is 1: 0.9 to 1.0.
The method according to claim 1 or 2, wherein the quaternizing agent of step (b) is one or two or more selected from the group consisting of alkyl halides and dialkyl sulfates.
The method according to claim 1 or 2, wherein the low molecular alcohol of step (b) is a softener, characterized in that one or two or more mixtures selected from the group consisting of isopropyl alcohol, ethanol, propylene glycol and dipropylene glycol. Manufacturing method.
The method according to claim 1 or 2, wherein the reaction of step (b) is carried out at 50 to 80 ° C. for 1 to 24 hours.
The method of claim 1 or 2, further comprising the step of adding and stirring sodium chlorite and hydrogen peroxide after the step (b).
20 to 90% by weight of at least one ester quart selected from the compounds represented by the formulas 1 to 3 of claim 1 and glycerin, glyceryl ester or the like A fabric softener comprising 10 to 80% by weight of the mixture.