KR100861699B1 - Improved preparation method of a fabric softener using alkali catalysts - Google Patents

Abstract

The present invention comprises a step of transesterifying an oil containing fatty acid and a tertiary hydroxyalkylamine under a specific ratio of an alkaline main catalyst and a sodium hypophosphate subcatalyst to obtain a fatty acid hydroxyalkylamine ester (step 1); And reacting the fatty acid hydroxyalkylamine ester obtained in step 1 with a quaternizing agent in a low molecular weight alcohol solvent to obtain a fiber softener including ester quart (step 2). A fabric softener prepared using a combination of a specific proportion of alkali catalyst and sodium hypophosphate according to the present invention, when compared to the fabric softener produced by the conventional method, the color of the fabric softener is improved, and Low content of converted triglyceride oils and good long term stability. In addition, since the catalyst used in the present invention is cheaper than the sodium borohydride catalyst conventionally used to exhibit the same color of the softener, it is economical in production cost. Therefore, the present invention can be usefully used to prepare a fabric softener.

Triglyceride, Cationic Fiber Softener, Ester Exchange Reaction, Alkali Catalyst

Description

Improved preparation method of a fabric softener using alkali catalysts

The present invention provides an improved fabric softener using a combination of a specific proportion of alkali catalyst and sodium hypophosphite in the transesterification of vegetable or animal oils containing fatty acids with tertiary hydroxyalkylamines. The present invention relates to a fiber softener comprising 20 to 90 wt% of esterquat and glycerine, glyceryl ester or a mixture thereof 80 to 10 wt% .

Fabric softener is a laundry aid used to soften the cloth after washing. It not only softens the fabric by making use of the fiber, but also helps to prevent static electricity and detergent residue by adsorbing cationic surfactant on the fiber. Do it.

Recently, as the price of fatty acids continues to rise, there is an economic problem in which the manufacturing cost increases when fabricating fabric softeners. To solve this problem, many studies have been conducted to prepare ester quart compounds through ester exchange by directly reacting oils with amines. In particular, methods for obtaining direct ester quarts by reacting oils with amines substituted with hydroxyl groups have been mainly developed.

However, the method of preparing the cationic fiber softener directly from the oil has a high content of unconverted triglyceride oil, and the color of the fabric softener produced is not good. Strong alkali and boron hydride-based catalysts were used to prepare the compounds having improved.

Conventional techniques using the strong alkali catalyst are as follows.

In one embodiment of U.S. Patent No. 5,637,743, after partial transesterification reaction using sodium methylate as a catalyst on partially hydrogenated palm oil and triethanolamine, Quaternization with dimethylsulfate has been disclosed, and in another embodiment, hypophosphorous acid is used as a catalyst for a mixture of palm oil, dimethylaminopropylamine and triethanolamine. After the transesterification reaction, quaternization with dimethylsulfate was started.

U.S. Patent 5,869,716 discloses (1) oil and hydroxy in the presence of a catalyst selected from the group consisting of alkali metal boron hydride, alkali earth metal boron hydride and combinations thereof. Reacting a tertiary amine with functional groups; And (2) reacting the product produced in step (1) with a quaternizing agent.

In this patent, alkaline earth metal boron hydride, phosphoric acid as a catalyst to shorten the color and reaction time of the product in a method for producing ester quarts directly from natural fat or oil Or their alkaline earth metal salts, specifically, unsaturated whole or partially hydrogenated tallow or palm oil having an iodine value of 0 to 50, and diethanol methylamine, 1,2 Sodium borohydride and hypophosphorous acid as catalysts in the transesterification reaction of 1,2-dihydroxypropyl dimethylamine, triethanolamine and / or mixtures of these amines Alternatively, sodium hypophosphite was used in an amount of 0.05 wt% to 0.1 wt%, indicating a color improvement of the fabric softener.

US Patent Nos. 6,906,025 and 7,001,879 relate to softeners for use in automatic dryers and their use, in particular the softeners 20 to 80% of quaternary ammonium salts, mixtures containing glycerin and glyceryl esters 80 to 20 It is composed of%, and has a melting property at 30 ~ 65 ℃, it was disclosed that it can be used by coating on a substrate. More specifically, the softening agent was used by mixing sodium borohydride, or sodium borohydride and calcium hydroxide as a catalyst in the transesterification reaction of oil and amine in the form of triglycerides.

However, since the alkali / alkaline earth metal borohydride catalyst has a high cost of 50,000 won / kg, there is a problem of an increase in the cost of producing a cationic fiber softener using the same.

Therefore, the inventors of the present invention are economical and manufactured in order to solve the above problems, excellent color of the fabric softener, low oil content of the unconverted triglyceride form, high hydrolysis stability, excellent flexibility and water absorption, While researching on the fabrication of low-yellowing fabric softeners, the combination of alkali catalyst and sodium hypophosphate in specific proportions resulted in excellent color, low oil content in the form of unconverted triglycerides, and high hydrolytic stability. The present invention was completed by confirming that it is excellent in softness and water absorption, has low yellowing, and can produce an economical fabric softener.

SUMMARY OF THE INVENTION An object of the present invention is to provide an improved method of preparing a fabric softener using a combination of a specific proportion of an alkali catalyst and sodium hypophosphate in the transesterification of vegetable or animal oils containing fatty acids with tertiary hydroxyalkylamines. have.

Another object of the present invention is to provide a fabric softener comprising 20 to 90% by weight of the ester quart prepared using the production method and 80 to 10% by weight of glycerin, glyceryl ester or a mixture thereof.

In order to achieve the above object, the present invention

Transesterifying a vegetable or animal oil including fatty acid with a tertiary hydroxyalkylamine under a specific ratio of an alkali main catalyst and a sodium hypophosphate subcatalyst to obtain a fatty acid hydroxyalkylamine ester (step 1); And

By using the alkali catalyst comprising the step (step 2) of reacting the fatty acid hydroxyalkylamine ester obtained in step 1 with a quaternizing agent in a low-molecular alcohol solvent to obtain a fiber softener comprising an ester quart of the formula (1) Provided is an improved method for preparing a fabric softener.

(In Formula 1,

R ₁ is a straight or branched chain alkyl group or alkenyl group having 6 to 22 carbon atoms, preferably 16 to 18 carbon atoms;

R ₂ And R ₃ is 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 represents halide, alkyl sulfate, alkyl phosphate.)

(In Formula 2,

R ₁ , R ₂ , m, and n are as defined in Formula 1,

R ₄ and R ₅ are each independently an alkyl group having 1 to 4 carbon atoms.)

(In Chemical Formula 3,

R ₁ , R ₂ , R ₄ , m, and n are as defined in Formula 1,

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 1 is a step of transesterifying a vegetable or animal oil containing fatty acid with a tertiary hydroxyalkylamine under a specific ratio of an alkaline main catalyst and a sodium hypophosphite subcatalyst to obtain a fatty acid hydroxyalkylamine ester.

In the step 1 of the present invention, the vegetable or animal oil containing a fatty acid used as a raw material is a monoglyceride represented by the formula (4) or 5, a diglyceride represented by the formula (6) or 7 or a triglyceride represented by the formula (8) It consists of a mixture of forms of the ride, of which triglyceride forms are the main.

The vegetable or animal oil including the fatty acid includes a fatty acid having a saturated or unsaturated hydrocarbon moiety represented by R ₈ , R ₉ , R ₁₀ , R ₁₁ , R _12, or R ₁₃ in the following Chemical Formulas _4-8 . In this case, the number of carbon atoms of the saturated or unsaturated hydrocarbon group is preferably a C ₆ ~ C _22, more preferably the C ₁₆ ~ C _18.

(In Formula 4, R ₈ is a linear or branched alkyl or alkenyl group having 6 to 22 carbon atoms.)

(In Chemical Formula 5, R ₈ is as defined in Chemical Formula 4.)

(In Formula 6, R ₉ and R ₁₀ are independently a linear or branched alkyl or alkenyl group having 6 to 22 carbon atoms.)

(In Chemical Formula 7, R ₉ and R ₁₀ are the same as defined in Chemical Formula 6.)

(In Chemical Formula 8, R ₁₁ , R ₁₂ , And R ₁₃ are each independently a linear or branched alkyl or alkenyl group having 6 to 22 carbon atoms.)

At this time, the vegetable or animal oil including fatty acids used may be saturated or unsaturated bee tallow oil, palm oil, palm kernel oil, palm stearine oil, Palm olein oil, coconut oil, coconut oil, olive oil, rapeseed oil, sunflower oil, sunflower oil, cottonseed oil, soyabean oil ) And the degree of unsaturation of the vegetable or animal oil containing the fatty acid is preferably from 0 to 70. Herein, 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 1 according to the invention causes an ester exchange reaction with the fatty acids of the vegetable or animal oil. At this time, the tertiary amine used may be diethanol methylamine, 1,2-dihydroxypropyl dimethylamine, triethanolamine and the like.

In step 1 according to the present invention, the reaction molar ratio of fatty acids of vegetable or animal oils including tertiary hydroxyalkylamine and fatty acids is preferably 1: 1 to 2.7. If the reaction molar ratio of the fatty acid of the vegetable or animal oil including the tertiary hydroxyalkylamine and the fatty acid is less than 1: 1, the amount of fatty acid converted from the oil is relatively small, and as a result, the softening effect is lowered. In addition, when the reaction molar ratio exceeds 1: 2.7, the amount of triester in 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 the main catalyst, for example, sodium hydroxide (sodium hydroxide), potassium hydroxide (potassium hydroxide), calcium hydroxide (calcium hydroxide), sodium carbonate anhydrous (sodium carbonate anhydrous) and the like can be used. .

The addition amount of the alkali catalyst is preferably 0.01 to 0.1%, more preferably 0.01 to 0.05% of the sum of the weight of the vegetable or animal oil containing the fatty acid and the amine. If the addition amount of the alkali catalyst is less than 0.01% there is a problem that the content of the unconverted triglyceride oil is high, if it exceeds 0.1% there is a problem that the color of the fabric softener is not good.

In addition, the subcatalyst is added to improve the color and reactivity of the transesterification reaction, and may be used as the subcatalyst sodium sodium phosphate. The amount of the subcatalyst added is preferably 0.01 to 0.1%, more preferably 0.05 to 0.1% of the sum of the weight of the vegetable or animal oil containing the fatty acid and the amine. If the amount of the sodium hypophosphate added is less than 0.01%, there is a problem in the color of the fabric softener, and if it exceeds 0.1%, there is a problem of precipitation as a residue in the product and the occurrence of odor.

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

Performing step 1 according to the present invention results in the transesterification of the tertiary hydroxyalkylamine with the fatty acid moiety of the vegetable or animal oil to give a fatty acid hydroxyalkylamine ester, and the degree of performance of the transesterification reaction. Depending on this, the following residues may remain.

First, when all of the fatty acids in the oil are converted into fatty acid hydroxyalkylamine esters by tertiary hydroxyalkylamine and ester exchange reaction, glycerin of Formula 9 remains as a residue.

Next, when the fatty acid of the oil is partially converted to the fatty acid hydroxyalkylamine ester by the transesterification reaction with the tertiary hydroxyalkylamine, according to the number of fatty acids which remain unchanged in the oil, The glyceryl ester form of the compound remains as a residue.

(In Formula 10, R ₁₄ and R ₁₅ are each independently a linear or branched alkyl group or alkenyl group having 6 to 22 carbon atoms.)

(In Chemical Formula 11, R ₁₄ and R ₁₅ are as defined in Chemical Formula 10.)

(In Chemical Formula 12, R ₁₆ is a linear or branched alkyl group or alkenyl group having 6 to 22 carbon atoms independently of each other.)

(In Chemical Formula 13, R ₁₆ is as defined in Chemical Formula 12.)

Next, step 2 is a step of obtaining a fibrous softener comprising an ester quart by reacting the fatty acid hydroxyalkylamine ester obtained in step 1 with a quaternizing agent in a low molecular alcohol solvent.

The reaction molar ratio of the fatty acid hydroxyalkylamine ester and the quaternization agent of step 2 according to the present invention is preferably 1: 0.9 to 1.0, and if the reaction molar ratio is less than 1: 0.9, the unreacted fatty acid hydroxyalkylamine ester Is relatively increased and scum occurs, and there is a problem in emulsification. If it exceeds 1: 1.0, there is a problem in that stability and color of the product are not good because the pH in the product is too low and the unreacted quaternizing agent remains.

The quaternizing agent used in step 2 according to the present invention includes alkyl halides such as methyl chloride; Dialkyl phosphates such as dimethyl sulfate and the like; It is preferable to use dialkyl carbonates such as dimethyl carbonate, diethyl carbonate and the like.

The low molecular alcohol solvent used in step 2 according to the present invention may be used alone or mixed with isopropyl alcohol (isopropyl alcohol), ethanol (ethanol), propylene glycol (dipropylene glycol), dipropylene glycol and the like. .

The quaternization reaction of step 2 according to the present invention is preferably carried out at 50 ~ 80 ℃, more preferably 50 ~ 60 ℃, the reaction time is preferably 1 ~ 24 hours, more preferably 2 It may be performed for ˜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, it is preferable that the addition amount of sodium chlorite and fruit water is 0.05 to 1.0% of the total weight. If the addition amount of the sodium chlorite and fruit tree is less than 0.05%, there is no color improving effect, and if it exceeds 1.0%, there is no further color improvement.

Finally, the preparation method according to the present invention using a mixture of an alkali catalyst and sodium hypophosphate in a specific ratio is 20 to 90% by weight of ester quarts (acyloxyalkyl quaternary ammonium compounds) of Formulas 1 to 3 and glycerin of Formula 9 To provide a fiber softener comprising 80 to 10% by weight of glyceryl ester of the formula (10) to 13 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), compared to the fiber softeners produced by conventional methods. Good long term stability (see Table 3). In addition, since the catalyst used in the present invention is cheaper than the sodium borohydride catalyst conventionally used to exhibit the same color of the softener, it is very economical in terms of manufacturing cost. Therefore, the present invention can be usefully used to prepare a fabric softener.

Hereinafter, the present invention will be described in detail by Examples and Experimental Examples. However, the following examples are merely to illustrate the present invention, but the content of the present invention is not limited by the following examples.

< Example  1> using sodium hydroxide catalyst Fabric softener  Produce

(1) Ester exchange reaction

2,065 g of palm stearin oil in a 2-liter four-necked glass reactor equipped with a paddle type stirring device capable of controlling the rotational speed, a nitrogen supply device, a water removal cooler, and an electrothermal heating device capable of automatically controlling the temperature of the reaction system. 464.52 g of triethanolamine, 1.26 g of sodium hydroxide (0.05% of the total amount), and 2.53 g (0.1% of the total amount) of sodium hypophosphate were mixed and added with nitrogen microbubbles at the bottom of the reactor. Infused at a rate. Thereafter, the speed of the reaction stirrer was fixed at 250 to 300 rpm, and the temperature of the reactant was raised to 160 ° C. for 1 hour to remove water included in the raw material, maintained at the temperature for 2 hours, and then heated up to 190 ° C. After stirring for 8 hours, the mixture was cooled to 65 ° C. or lower to obtain a fatty acid hydroxyalkylamine ester.

(2) Quaternization reaction

To the fatty acid hydroxyalkylamine ester obtained in the above (1), 130 g of isopropyl alcohol was added to 10% of the total amount, and the dry solid content was about 90%. Subsequently, 138.7 g of dimethyl sulfate, a quaternizing agent, was slowly dropped one drop at a time and quaternized at 50 to 60 ° C. for 2 hours to prepare a fiber softener.

< Example  2>

(1) Ester exchange reaction

A fatty acid hydroxyalkylamine ester was obtained in the same manner as in (1) of Example 1, except that 1.26 g (0.05% of the total amount) of potassium hydroxide was added to the reactor instead of sodium hydroxide.

(2) Quaternization reaction

Fibrous softener was prepared in the same manner as in Example (2).

< Example  3>

(1) Ester exchange reaction

A fatty acid hydroxyalkylamine ester was obtained in the same manner as in the method of (1) of Example 1, except that 1.26 g of calcium hydroxide (0.05% of the total amount) was added to the reactor instead of sodium hydroxide.

(2) Quaternization reaction

Fibrous softener was prepared in the same manner as in Example (2).

< Example  4>

(1) Ester exchange reaction

A fatty acid hydroxyalkylamine ester was obtained in the same manner as in (1) of Example 1, except that 1.26 g of anhydrous sodium carbonate (0.05% of the total amount) was added to the reactor instead of sodium hydroxide.

(2) Quaternization reaction

Fibrous softener was prepared in the same manner as in Example (2).

< Comparative example  1>

A fibrous softener was prepared in the same manner as in Example 1 except that 0.05% of the total amount of sodium hydroxide alone was added as a catalyst.

< Comparative example  2>

A fibrous softener was prepared in the same manner as in Example 1 except that 0.05% of potassium hydroxide alone was added as a catalyst.

< Comparative example  3>

A fabric softener was prepared in the same manner as in Example 1, except that 0.05% of the total amount of calcium hydroxide alone was added as a catalyst.

< Comparative example  4>

A fabric softener was prepared in the same manner as in Example 1 except that 0.05% of the total amount of anhydrous sodium carbonate alone was added as a catalyst.

< Comparative example  5>

A fabric softener was prepared in the same manner as in Example 1, except that 0.05% of the total amount of sodium methoxide alone was added as a catalyst.

< Comparative example  6>

A fabric softener was prepared in the same manner as in Example 1, except that 0.05% of the total amount of sodium borohydride alone was added as a catalyst.

< Comparative example  7>

A fabric softener was prepared in the same manner as in Example 1, except that 0.05% of the total amount of sodium hypophosphate alone was added as a catalyst.

< Comparative example  8>

A fibrous softener was prepared in the same manner as in Example 1 except that 0.05% of the total amount of the phosphorous acid alone was added as a catalyst.

< Comparative example  9>

A fibrous softener was prepared in the same manner as in Example 1, except that 0.05% of sodium methoxide was added as a catalyst and 0.1% of sodium phosphate was added.

< Comparative example  10>

A fibrous softener was prepared in the same manner as in Example 1 except that 0.05% of calcium hydroxide and 0.1% of sodium borohydride were added as a catalyst.

< Comparative example  11>

A commercially available ester quart type softener (Ohsung Chemical Co., Ltd.) was used.

< Experimental Example  1> Fabric softener  Color measurement

In order to find out how the color of the fabric softener is improved by using a combination of a specific ratio of the alkali catalyst and sodium phosphate according to the present invention, the following experiment was performed.

The color of the fatty acid hydroxyalkylamine ester produced after the transesterification reaction according to Examples 1 to 4 and Comparative Examples 1 to 10 was measured at 45 ° C. using a colorimeter (Lovibond Tintometer PFX195), and the color was measured. The results are shown in Table 1.

division Color Chart Example 1 2.0 Example 2 2.1 Example 3 2.2 Example 4 2.2 Comparative Example 1 4.6 Comparative Example 2 5.7 Comparative Example 3 4.5 Comparative Example 4 4.5 Comparative Example 5 5.4 Comparative Example 6 4.0 Comparative Example 7 6.0 Comparative Example 8 5.5 Comparative Example 9 4.6 Comparative Example 10 2.6

As shown in Table 1, the fabric softener prepared by using a combination of a specific ratio of the alkali catalyst and sodium hypophosphate according to the present invention has a color of 2.0 to 2.2 Gardner, compared to Comparative Examples 1 to 9 using a conventional alkali catalyst ( 4.0 ~ 5.5 Gardner) Because it shows about 2 times brighter color, it can be found to be useful as a fabric softener. In addition, the fabric softener of Comparative Example 10, which uses calcium hydroxide and sodium borohydride as the catalyst, exhibits the same color as the present invention, but the alkali catalyst and sodium hypophosphate used as catalyst according to the present invention are much more than sodium borohydride. Since it is inexpensive, it can be seen that the manufacturing method of the fabric softener according to the present invention is economical in terms of cost.

< Experimental Example  2> unconverted Triglycerides  Oil content measurement

In order to determine the content of unconverted triglyceride oil in the preparation of the fiber softener using a combination of a specific ratio of the alkali catalyst and sodium hypophosphate according to the present invention, the following experiment was performed.

The unconverted triglyceride oil content after the transesterification reaction according to Examples 1 to 4 and Comparative Examples 1 to 10 was measured using gas chromatography (GC, Shimadzu 17A), and the measurement results are shown in Table 2. .

division Unconverted Triglyceride Oil Content (%) Example 1 5.4 Example 2 5.8 Example 3 5.6 Example 4 5.6 Comparative Example 1 8.0 Comparative Example 2 10.7 Comparative Example 3 7.6 Comparative Example 4 7.5 Comparative Example 5 15.9 Comparative Example 6 8.1 Comparative Example 7 19.1 Comparative Example 8 19.3 Comparative Example 9 10.8 Comparative Example 10 6.8

As shown in Table 2, the fabric softener prepared by using a combination of a specific proportion of the alkali catalyst and sodium hypophosphate according to the present invention had an unconverted triglyceride oil content of 5.4 to 5.8% compared to the comparative example (6.8 ~ 15.9%), the conversion rate is high. Therefore, it can be seen that the method using a combination of a specific proportion of alkali catalyst and sodium hypophosphate according to the present invention is useful for preparing a fabric softener.

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

In order to determine the degree of viscosity and long-term stability of the emulsion after the fabrication of the fabric softener using the alkali catalyst according to the present invention, the following experiment was performed.

500 ml, four-necked glass reactor equipped with a paddle type stirring device capable of controlling the rotation speed, a nitrogen supply device, a water removing cooler, and an electrothermal heating device capable of automatically controlling the reaction system temperature according to Examples 1 to 4 Manufactured softener and our product ester quart (Comparative Example 1) 38g softener (7.6% of total amount), 443g (88.6%) of water, 1g (0.2%) of polyethylene glycol lauryl ether 0.1 g (0.02%) of calcium chloride and 15 g of ethylene glycol were mixed. At this time, the speed of the reaction stirrer was fixed at 250 ~ 300 rpm, 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.

(One) pH

The prepared emulsion was measured for pH using a pH meter (Orion model 310).

(2) viscosity

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

(3) long-term stability

The prepared emulsion was placed in an oven at 45 ° C. and the date until separation of the emulsion occurred was measured weekly.

 The measurement results are shown in Table 3.

division content(%) pH Viscosity (cPs) Long-term stability Fabric softener Spices Calcium chloride Polyethylene Glycol Lauryl Ether Dye (0.1% Soln.) water Example 1 7.6 0.5 0.02 0.2 0.12 88.6 2.5 127 24 Example 2 7.6 0.5 0.02 0.2 0.12 88.6 2.4 125 25 Example 3 7.6 0.5 0.02 0.2 0.12 88.6 2.5 130 24 Example 4 7.6 0.5 0.02 0.2 0.12 88.6 2.5 126 23 Comparative Example 11 7.6 0.5 0.02 0.2 0.12 88.6 2.5 95 17

As shown in Table 3, the fabric softener prepared using a combination of a specific ratio of the alkali catalyst and sodium hypophosphate according to the present invention is stable over 23-25 weeks, according to the long-term stability measurement. It can be seen that much higher stability.

Thus, it can be seen that the process using a combination of a specific proportion of alkali catalyst and sodium hypophosphate according to the present invention is useful for preparing fibrous softeners.

As described above, the fabric softener prepared by using a combination of a specific ratio of the alkali catalyst and sodium hypophosphate according to the present invention, compared with the fabric softener produced by the conventional method, the color of the fabric softener is improved, the conversion rate It is high and has excellent long term stability. In addition, since the catalyst used in the present invention is cheaper than the sodium borohydride catalyst conventionally used to exhibit the same color of the softener, it is economical in production cost. Therefore, the present invention can be usefully used to prepare a fabric softener.

Claims (20)

Vegetables containing fatty acids and alkali main catalysts selected from the group consisting of sodium hydroxide, potassium hydroxide, calcium hydroxide and anhydrous sodium carbonate added at 0.01 to 0.1% of the sum of the weights of tertiary hydroxyalkylamines with vegetable or animal oils containing fatty acids Or fatty acid hydroxyalkylamine by transesterification of a vegetable or animal oil containing fatty acid with a tertiary hydroxyalkylamine under a sodium hypophosphate subcatalyst added at 0.05 to 0.1% of the sum of the weight of the animal oil and the tertiary hydroxyalkylamine. Obtaining an ester (step 1); And By using the alkali catalyst comprising the step (step 2) of reacting the fatty acid hydroxyalkylamine ester obtained in step 1 with a quaternizing agent in a low-molecular alcohol solvent to obtain a fiber softener comprising an ester quart of the formula (1) Improved method of making fabric softener. <Formula 1>

(In Formula 1, R ₁ is a straight or branched chain alkyl group or alkenyl group having 6 to 22 carbon atoms; R ₂ and R ₃ is 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 represents halide, alkyl sulfate, alkyl phosphate.) <Formula 2>

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

(In Chemical Formula 3, R ₁ , R ₂ , R ₄ , m, and n are as defined in Formula 1, R ₆ and R ₇ are each independently an alkyl group having 1 to 4 carbon atoms.) The method of claim 1, wherein R ₁ of Formula 1 is a straight or branched chain alkyl group or alkenyl group having 16 to 18 carbon atoms. According to claim 1, wherein the vegetable or animal oil comprising the fatty acid of step 1 comprises any one selected from the group consisting of mono-, di- and triglycerides represented by the formula 4 to 8 or a mixture thereof Method for producing an improved fabric softener using an alkali catalyst, characterized in that. <Formula 4>

(In Formula 4, R ₈ is a linear or branched alkyl or alkenyl group having 6 to 22 carbon atoms.) <Formula 5>

(In Chemical Formula 5, R ₈ is as defined in Chemical Formula 4.) <Formula 6>

(In Formula 6, R ₉ and R ₁₀ are independently a linear or branched alkyl or alkenyl group having 6 to 22 carbon atoms.) <Formula 7>

(In Chemical Formula 7, R ₉ and R ₁₀ are the same as defined in Chemical Formula 6.) <Formula 8>

(In Chemical Formula 8, R ₁₁ , R ₁₂ , And R ₁₃ are each independently a linear or branched alkyl or alkenyl group having 6 to 22 carbon atoms.) According to claim 3, wherein R ₈ , R ₉ , R ₁₀ , R ₁₁ , R ₁₂ and R ₁₃ of the general formula _4-8 is independently a linear or branched alkyl or alkenyl group having 16 to 18 carbon atoms, characterized in that Method for producing an improved fabric softener using an alkali catalyst. According to claim 1, wherein the vegetable or animal oil comprising the fatty acid of step 1 is saturated or unsaturated Uji oil, palm oil, palm kernel oil, palm stearin oil, palm olein oil, coconut oil, olive oil, rapeseed oil, A process for producing an improved fibrous softener using an alkali catalyst, characterized in that any one selected from the group consisting of sunflower oil, cottonseed oil and soybean oil. The method of claim 1, wherein the tertiary hydroxyalkylamine of step 1 is any one selected from the group consisting of diethanol methylamine, 1,2-dihydroxypropyl dimethylamine and triethanolamine or a mixture thereof. An improved method for producing a fabric softener using an alkali catalyst. The method according to claim 1, wherein the reaction molar ratio of the tertiary hydroxyalkylamine of step 1 and the fatty acid of the vegetable or animal oil including fatty acids is 1: 1 to 2.7, the production of an improved fabric softener using an alkali catalyst Way. delete delete The improved fiber using an alkali catalyst according to claim 1, wherein the amount of the alkali main catalyst added in step 1 is 0.01 to 0.05% of the sum of the weights of the vegetable or animal oil including the fatty acid and the tertiary hydroxyalkylamine. Method of Making Softener delete delete The method of claim 1, wherein the transesterification reaction of step 1 is carried out at 160 ~ 240 ℃ for 1 to 12 hours. The method according to claim 1, wherein the molar ratio of the fatty acid hydroxyalkylamine ester of the step 2 and the quaternizing agent is 1: 0.9 to 1.0. The method of claim 1, wherein the quaternizing agent of step 2 comprises an alkyl halide comprising methyl chloride; Dialkylsulfates, including dimethylsulfate; And a dialkyl carbonate comprising dimethyl carbonate and diethyl carbonate. The method of claim 1, wherein the low molecular alcohol is any one selected from the group consisting of isopropyl alcohol, ethanol, propylene glycol, dipropylene glycol, or a mixture thereof. . The method of claim 1, wherein the quaternization reaction of step 2 is carried out for 1 to 24 hours at 50 ~ 80 ℃. According to claim 1, wherein the improved fiber using an alkali catalyst characterized in that it further comprises the step of stirring by adding 0.05 ~ 1.0% of the total weight of the fabric softener, sodium chlorite and fruit tree to improve the color of the fabric softener Method of Making Softener 20 to 90% by weight of the ester quarts of the formulas (1) to (3) and the glycerin of the formula (9), the glyceryl ester of the formulas (10 to 13) Fabric softener comprising a mixture of 80 to 10% by weight. <Formula 9>

<Formula 10>

(In Formula 10, R ₁₄ and R ₁₅ are each independently a linear or branched alkyl group or alkenyl group having 6 to 22 carbon atoms.) <Formula 11>

(In Chemical Formula 11, R ₁₄ and R ₁₅ are as defined in Chemical Formula 10.) <Formula 12>

(In Chemical Formula 12, R ₁₆ is a linear or branched alkyl group or alkenyl group having 6 to 22 carbon atoms independently of each other.) <Formula 13>

(In Chemical Formula 13, R ₁₆ is as defined in Chemical Formula 12.) The fibrous softener according to claim 19, wherein R ₁₄ , R ₁₅ and R ₁₆ are each independently a linear or branched alkyl or alkenyl group having 16 to 18 carbon atoms.