JPH05132866A - Liquid softening and finishing agent - Google Patents

Abstract

PURPOSE:To obtain the subject finishing agent, containing a neutralized or a quaternized specific imidazoline compound as an essential component and capable of imparting excellent softness and resilience to various fibers. CONSTITUTION:A liquid softening and finishing agent is obtained by neutralizing an imidazoline compound expressed by formula I [R1 and R2 are 11-23C saturated or unsaturated hydrocarbon; (m) and (n) are 1-10; X is formula II or III; Q is formula IV or V] with an inorganic or organic acid or quaternizing the imidazoline compound with CH3.Cl, dispersing the resultant substance and preparing the agent. The prepared agent is capable of imparting excellent resilience (full touch) to fiber, excellent in preservation stability and improved in biodegradability.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a softening finish, and more particularly to a household liquid softening finish which can impart excellent flexibility and elasticity (puffiness) to various fibers.

[0002]

2. Prior Art and Problems to be Solved by the Invention
Most of the products sold as household softening agents are 1
It is a composition containing a quaternary ammonium salt having 1-2 long-chain alkyl groups in the molecule as a main component. The reason for this is that a small amount of quaternary ammonium salt has a good softening effect on various fibers.

The above-mentioned quaternary ammonium salt has a remarkable softening effect on cotton, but acrylic type,
The effect cannot be said to be sufficient for synthetic fibers such as polyester type and polyamide type, and if treated at a higher concentration, the elasticity of the garment may be reduced and the texture may be impaired. Further, when it is stored for a long period of time, it may thicken, gel, or separate, especially at low temperatures.
For this reason, various polyoxyethylene-based nonionic activators, electrolytes, and solvents other than the soft component are required, and many of them are mixed for stabilization, but the effect is still insufficient.

The above-mentioned softening agents having a quaternary ammonium salt as a main base are usually commercially available as 4 to 20% dispersions,
It is used. However, since the quaternary ammonium salt has a strong hydrophobicity, when it is added to the rinse water, when the stirring force is weak, the dispersibility in water is poor, and therefore the clothing may be uneven. Commercially available softeners contain various additives in addition to the above quaternary ammonium salt to improve the dispersibility in water, but the effect is still insufficient.

Further, liquid softening finishes having various amines as softening bases have been conventionally known. For example, JP-A-52-59
7965 discloses a composition for imparting flexibility to a fiber containing a long-chain alkylamine such as methyldi (hardened tallow alkyl) amine, and JP-A-58-6070 discloses an acylated alkanolamine, a water-soluble composition. A fiber material finishing agent that imparts smoothness and a comfortable feel to a fiber containing a quaternary ammonium salt and a fatty acid ester is disclosed in JP-A-61-167083. Quaternary ammonium compounds, higher fatty acids and hydroxy lower alkyls. A softener having good dispersibility containing a polyamine polyglycol ether is disclosed in JP-A-61-275474. , JP Sho
64-85368 discloses a softening composition containing a dilong chain alkylamine-anionic surfactant ion pair complex, a non-silicone wax and a liquid carrier, and JP-A-2-6662 discloses hydroxy lower alkyl. A fabric conditioning composition containing an amine such as a condensate of an alkylenediamine and a higher fatty acid and an amphoteric fabric conditioning agent is disclosed in JP-A-2-14076, which is a softening agent containing a dilong-chain alkylamine-polyfunctional carboxylic acid complex. , A fabric conditioning composition that imparts antistatic properties. Further, JP-A-52-5394 describes a fabric condition-controlling composition containing an antistatic agent containing a mono- or di-long-chain alkylalkylenediamine and a quaternary ammonium softener.

Although the softener containing these amines is relatively better in dispersibility and storage stability than the softener containing a quaternary ammonium salt, the softening performance is still insufficient. Recently, there is a growing concern over the impact on the environment all over the world, and a base material having excellent biodegradability and the like is beginning to be demanded as a softening finishing agent. However, the softeners containing these amines shown above are not sufficiently effective in this respect as well.

[0007]

Means for Solving the Problems As a result of intensive studies to solve the above-mentioned problems with a softener containing an amine, the present inventors have found that a neutralized product or a quaternized product of a specific imidazoline compound is excellent in flexibility. In addition, the clothing is elastic (puffy)
The present invention has been completed by finding that the above can be added.

That is, the present invention is a liquid softening agent characterized by containing a neutralized product or a quaternized product of an inorganic acid or an organic acid of a compound represented by the following general formula (I) as an essential component. Is provided.

[0009]

[Chemical 3]

[Wherein R ₁ and R ₂ are linear or branched saturated or unsaturated hydrocarbon groups having 11 to 23 carbon atoms, preferably 13 to 21 carbon atoms, particularly preferably 15 to 19 carbon atoms, and m and n are 1 ~ 10, preferably 2
Represents an integer of 5;

[0011]

[Chemical 4]

A typical example of the imidazoline compound represented by the general formula (I) used in the present invention is one having two long chain groups in the imidazoline skeleton, and one of the long chain groups is linked to an amide group. Examples thereof include those having one part as the linking part and the other having the ester group as the connecting part, or those having both two long chain groups as the connecting part. These imidazoline compounds can be synthesized as shown below. For example, 6-hexanolide is reacted with aminoethylethanolamine and further imidazolinated to obtain an imidazoline compound having two hydroxyl groups. This is subjected to a dehydration condensation reaction with a long chain carboxylic acid to obtain a di long chain ester imidazoline compound. Further, 6-hexanolide is reacted with diethylenetriamine and further imidazoline-ized to obtain an imidazoline compound having one amino group and one hydroxyl group. This is dehydrated and condensed with a long-chain carboxylic acid to obtain a long-chain amide long-chain ester imidazoline compound having an amide group at the 1-position and an ester group at the 2-position. Further, by reacting caprolactam with aminoethylethanolamine and further imidazolinating it, an imidazoline compound having one amino group and one hydroxyl group is obtained. This is dehydrated and condensed with a long-chain carboxylic acid to obtain a long-chain ester long-chain amide imidazoline compound having an ester group at the 1-position and an amide group at the 2-position. As the fatty acid from which the long-chain group is derived, coconut oil,
Naturally-occurring ones such as palm oil, beef tallow, rapeseed oil, and fish oil are generally used, but chemically synthesized fatty acids may be used. The acid for obtaining the neutralized product of the imidazoline compound represented by the general formula (I) used in the present invention, hydrochloric acid, sulfuric acid, nitric acid, inorganic acids such as phosphoric acid, acetic acid, lactic acid, glycolic acid,
Examples thereof include organic acids such as citric acid, maleic acid, fumaric acid, and toluenesulfonic acid. As the quaternizing agent to obtain a quaternary compound, CH ₃ Cl, and the like.

In the present invention, the neutralized product or quaternized product of the imidazoline compound represented by the general formula (I) is contained in the liquid softening agent in an amount of 4 to 40% by weight, preferably 6 to 30% by weight, and particularly preferably. It is desirable that 10 to 25% by weight is blended.

The liquid softening agent of the present invention has a general formula
(I) is obtained by slowly adding a melt or concentrated solution of an imidazoline compound represented by (I) under stirring or shear mixing to an aqueous solution containing a neutralizing agent, but is not limited to this method. It can also be obtained by a method in which the neutralized product is produced in advance or the neutralized product is added later.

Since the imidazoline compound represented by the general formula (I) has an ester group in the molecule, it is excellent in biodegradability and is a soft base material which does not cause a problem in the natural environment. Is also one of the features.

The softening agent of the present invention may be further modified with a silicone compound such as dimethylpolysiloxane or dimethylpolysiloxane partially modified with an amino group or a polyoxyalkylene group, particularly preferably partially modified with a polyoxyalkylene group. By blending the dimethylpolysiloxane described above, it is possible to improve the feel of the softly treated clothing without impairing the water absorption. These silicone compounds are neutralized products of imidazoline compounds represented by the general formula (I) or 4
It is preferable to add 0.3 to 5% by weight to the graded product.

The softening agent of the present invention has almost the same softening effect as that of the hardened tallow alkyldimethylammonium chloride which has been widely used in the past, but surprisingly, it has elastic elasticity. Do you get it.

When the composition of the present invention is used as an aqueous liquid softening agent, an inorganic electrolyte such as sodium chloride, calcium chloride or magnesium chloride is added in an amount of 0.05 to 0.4 to adjust the viscosity.
Addition by weight% is desirable.

Although the liquid softening agent of the present invention has a high stability for long-term storage, it has a polyoxyethylene (5 to 50 mol) alkyl or alkenyl (C ₁₂ ) for stabilization under severe storage conditions. To C ₂₄ ) ether or polyoxypropylene (5 to 50 mol) alkyl or alkenyl (C _{12 to} C ₂₄ ) ether, polyoxyethylene (5 to 50 mol) alkyl (C ₁₂ to
A nonionic surfactant such as C ₂₄ ) amine, a solvent such as ethanol, propylene glycol, glycerin, urea, or the like can be added. Also, known esters as soft bases, nonionic or cationic compounds, long-chain alcohols, long-chain fatty acids and the like may be used in combination. It is also possible to incorporate pigments or dyes for the appearance of the product, fluorescent brighteners for the whiteness of the finish, and fragrances for a good taste when used and after the finish.

[0020]

EFFECT OF THE INVENTION The softening agent of the present invention is capable of imparting sufficient flexibility and antistatic properties to various fibers, imparting excellent elasticity, and excellent biodegradability.

[0021]

EXAMPLES The present invention will now be described in detail with reference to examples, but the present invention is not limited to these examples.

Examples 1 to 5 and Comparative Example 1 Liquid prepared by using a neutralized product or a quaternized compound of the compound represented by the general formula (I) having the structure shown in Table 1 in the compounding amount shown in Table 2. The following evaluation was performed using the softening finish.

[0023]

[Table 1]

<Preparation Method of Liquid Softening Finish> The melt of the amine as the component (a) is added to water at 50 ° C. under stirring,
Next, an acid neutralization product was obtained by adding an acid. In the case of a quaternary compound, the melt of the amine quaternary compound as the component (a) is added to water at 50 ° C under stirring and
A dispersion of graded product was obtained. 1) Evaluation of flexibility and elasticity (1) Treatment method Commercial cotton towel 2kg, acrylic jersey 1kg 3.5 °
After washing with a commercially available detergent attack (Kao Co., Ltd., registered trademark) 5 times repeatedly with DH hard water (30 liter washing machine) to remove the fiber treatment agent attached to each fiber, the compounding composition of Table 2 was obtained. 1.5 g of the active ingredient was added and treated at 25 ° C. for 1 minute under stirring. (2) Evaluation method The cloth treated by the above method was air-dried indoors, and then left in a constant temperature and humidity room at 25 ° C and 65% RH for 24 hours. The softness and elasticity of these cloths were evaluated. For the evaluation of softness and elasticity, pairwise comparison was carried out using a cloth treated with 10 cc of a softening agent consisting of 15% by weight of dihydrogenated tallow alkyldimethylammonium chloride as a control. The evaluation is expressed as follows. +2; softer or more elastic than the control +1; slightly softer or more elastic than the control 0; same as the control -1; slightly softer or less elastic than the control -2; more control Is softer or less elastic than the control

[0025]

[Table 2]

As shown in Table 2, by using the neutralized product or quaternized product of the imidazoline compound according to the present invention, the effect of satisfying both flexibility and elasticity can be obtained.

Examples 6 to 8 and Comparative Example 2 In order to evaluate the elasticity of the compositions having the formulations shown in Table 3, the pile height of cotton towels was measured. <Evaluation of elasticity> A cotton towel treated in the same manner as in Examples 1 to 5 is folded into eight, and three sheets are piled up to be piled up at 5 g / cm ^2.
After pressurizing with the pressure of 5 minutes for 5 minutes, the pressure was removed and the height of the towel was measured. The higher the towel height, the better the elasticity.

[0028]

[Table 3]

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[Procedure amendment]

[Submission date] December 8, 1992

[Procedure Amendment 1]

[Document name to be amended] Statement

[Name of item to be corrected] 0019

[Correction method] Change

[Correction content]

Although the liquid softening agent of the present invention has a high stability for long-term storage, it has a polyoxyethylene (5 to 50 mol) alkyl or alkenyl (C ₁₂ ) for stabilization under severe storage conditions. To C ₂₄ ) ether or polyoxypropylene (5 to 50 mol) alkyl or alkenyl (C _{12 to} C ₂₄ ) ether, polyoxyethylene (5 to 50 mol) alkyl (C ₁₂ to
C ₂₄ ) Nonionic surfactants such as amines, ethanol, ethyl
Solvents such as len glycol, propylene glycol, glycerin or urea may be added. Also, known esters as soft bases, nonionic or cationic compounds, long-chain alcohols, long-chain fatty acids and the like may be used in combination. In addition, for the appearance of the product, pigment or dye,
Fluorescent brighteners may be added for the whiteness of the finish, and fragrances may be added to improve the taste when used and after the finish.

Claims (1)

[Claims] 1. A liquid softening agent comprising a neutralized product or a quaternized product of an inorganic acid or an organic acid of a compound represented by the following general formula (I) as an essential component. [Chemical 1] [In the formula, R ₁ and R _{2 each} represent a linear or branched saturated or unsaturated hydrocarbon group having 11 to 23 carbon atoms, and m and n each represent an integer of 1 to 10. [Chemical 2]