JP3062355B2 - Liquid softener composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel amine derivative and a liquid softening agent composition containing the same, and more particularly, to an excellent flexibility and elasticity (fluffiness) to various fibers. Also, the present invention relates to a liquid softener for household use containing a neutralized or quaternized acid of a specific amine having excellent storage stability as an essential component.

[0002]

2. Description of the Related Art
Most of the products marketed as softeners for household use are mainly composed of quaternary ammonium salts having two long-chain alkyl groups in one molecule such as di (hardened tallowalkyl) dimethylammonium chloride. The composition was as follows. The reason for this is that the quaternary ammonium salt has a good softening effect on various fibers in a small amount.

However, the above quaternary ammonium salts have a remarkable softening effect on cotton, but are not sufficiently effective on synthetic fibers such as acrylic, polyester and polyamide fibers. It is difficult to say that if the treatment is carried out at a higher concentration, the elasticity of the garment may be reduced and the texture may be impaired.

Further, since the quaternary ammonium salt has a strong hydrophobicity, when it is put into rinse water, if the stirring power is weak, the quaternary ammonium salt is poorly dispersible in water, and thus may be uneven to clothing. In particular, in the case of long-term storage at a low temperature, the viscosity may increase, the gel may be formed, or the separation may occur. Commercially available softeners include polyoxyethylene-based nonionic surfactants in addition to the above quaternary ammonium salts,
Additives such as an electrolyte and a solvent are added to improve dispersibility in water and long-term storage stability, but the effects are still insufficient.

[0005] In addition, liquid softeners based on various amines as softer bases have been known. For example, Japanese Unexamined Patent Publication No.
Japanese Patent No. 59796 discloses a composition for imparting flexibility to a fiber containing a long-chain alkylamine such as methyldi (hardened tallowalkyl) amine. Japanese Patent Application Laid-Open No. 58-60070 discloses an acylated alkanolamine, Japanese Patent Application Laid-Open No. 61-166703 discloses a fiber material finishing agent for imparting smoothness and comfortable feel to fibers containing a quaternary ammonium salt and a fatty acid ester. A softener having a good dispersibility containing a condensation reaction product with an alkylamine polyglycol ether and a di (higher alkyl) cyclic amine and a Bronsted acid are disclosed in JP-A-61-275474. JP-A-64-85368 discloses a divalent long chain alkylamine-anionic surfactant ion-pair complex, a non-silicone wax and JP-A-2-6662 discloses a softening composition containing a liquid carrier and a fabric conditioning composition containing an amine such as a condensate of a hydroxy lower alkylalkylenediamine and a higher fatty acid and an amphoteric fabric conditioning agent. JP-14076 describes a fabric conditioning composition containing a dilong chain alkylamine-polyfunctional carboxylic acid complex to impart flexibility and antistatic properties. Further, JP-A-52-5394
In the publication, a fabric conditioning composition containing a mono- or di-long-chain alkylalkylenediamine antistatic agent and a quaternary ammonium softener is described.

However, these amine-containing softeners are relatively better in dispersibility and storage stability than quaternary ammonium salt-containing softeners, but their softening performance is still insufficient.

[0007]

Means for Solving the Problems The present inventors have made intensive studies to solve the above problems, and as a result, completed the present invention.

That is, the present invention provides a compound represented by the general formula (I)

[0009]

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[In the formula, R ₁ and R ₂ represent a straight-chain or branched saturated or unsaturated hydrocarbon group having 8 to 24 carbon atoms, and R represents a C 8 to C 24 carbon atom.
A linear or branched saturated or unsaturated hydrocarbon group, hydroxyethyl group or hydroxypropyl group, m,
n represents an integer of 2 to 6, and p and q represent an integer of 1 to 20. And / or a quaternized acid of the amine represented by the general formula (II):

[0011]

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[In the formula, R ₃ and R ₄ represent a straight-chain or branched saturated or unsaturated hydrocarbon group having 8 to 24 carbon atoms, and r represents an integer of 1 to 20. There is provided a liquid softener composition characterized by containing the expressed acid neutralization product of an amine or quaternized product in] as <br/> essential component.

The compound represented by the general formula (I) is a compound represented by the following general formula (III), and the compound represented by the general formula (II) is a compound represented by the following general formula (IV). It can be easily obtained by subjecting the represented compound to an acylation reaction of a carboxylic acid or a derivative thereof by a usual method.

[0014]

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Representative examples of the amine compound according to the present invention include diacylated N-methyl-N-hydroxyethylpropylenediamine and acylated imidazoline having a hydroxyl group. Carboxylic acids used in the acylation reaction formula R-O- (CH ₂ CH ₂
O) _s -CH ₂ COOH _(s can be expressed by an a) integer from 1 to 20. This carboxylic acid can be easily obtained by adding ethylene oxide to a long-chain alcohol and then performing carboxymethylation with a halogenated acetic acid such as chloroacetic acid or bromoacetic acid. The long-chain alcohol used here is generally derived from natural fats and oils such as coconut oil, palm oil, beef tallow, lard, rapeseed oil and fish oil, but may be chemically synthesized.

The acid for obtaining a neutralized product from the amine compound represented by the general formula (I) or the amine compound represented by the general formula (II) includes inorganic acids such as hydrochloric acid, sulfuric acid, phosphoric acid and nitric acid. And organic acids such as acetic acid, glycolic acid, lactic acid, citric acid, maleic acid, fumaric acid, and toluenesulfonic acid. Examples of the quaternizing agent include, in addition to alkyl halide compounds such as methyl chloride, alkyl sulfate compounds such as dimethyl sulfate.

Since the amine compound represented by the general formula (I) and the amine compound represented by the general formula (II) have an ester group in the molecule, the neutralized salt and the quaternized compound are biodegradable. It is a flexible base that is excellent and has no problem for the natural environment.

The liquid softener composition of the present invention comprises an acid-neutralized or quaternized amine represented by the general formula (I) and / or
Or an acid neutralized or quaternized amine represented by the general formula (II) is contained as an essential component. Acid-neutralized or quaternized amines represented by the general formula (I) and / or the general formula (II)
The acid-neutralized product or quaternized product of the amine represented by the formula (I) is 1 to 30% by weight, preferably 4 to 30% by weight, particularly preferably 10 to 25% by weight in the liquid softener composition of the present invention. % By weight. The balance of the liquid softener composition of the present invention is water and optional components.

The liquid softener composition of the present invention can be prepared, for example, by stirring a melt or a concentrated solution of the amine compound represented by the general formula (I) and / or the amine compound represented by the general formula (II) under stirring. It can be obtained by slowly adding an aqueous solution containing a neutralizing agent under shear mixing, but is not limited to this method, and a method of preparing a neutralized product in advance or a method of adding a neutralized product later And the like.

The liquid soft finish composition of the present invention may further comprise a silicone compound such as dimethylpolysiloxane, dimethylpolysiloxane partially modified with an amino group or a polyoxyalkylene group, particularly preferably a polyoxyalkylene. By blending the dimethylpolysiloxane modified with a group, the texture of the softly treated clothing can be improved without impairing the water absorption performance. These silicone compounds are neutralized products of the amine compound according to the present invention or 4
It is preferred that the content is 0.3 to 5% by weight based on the total amount of the graded products. In addition, for adjusting the viscosity, an inorganic electrolyte such as sodium chloride, calcium chloride, magnesium chloride, etc.
It is desirable to add 0.4% by weight.

Although the liquid soft finish composition of the present invention has high stability for long-term storage, it is more stable for harsh storage conditions, so that polyoxyethylene (5 to 50 mol) alkyl or alkenyl ( A nonionic surfactant such as C ₁₂ -C ₂₄ ) ether, a solvent such as ethanol, propylene glycol, ethylene glycol and glycerin, or urea can be blended. Further, known esters, nonionic or cationic compounds, long-chain alcohols and the like may be used in combination as a soft base.

It is also possible to incorporate a pigment or dye for the appearance of the product, a fluorescent whitening agent for the whiteness of the finish, and a fragrance for improving the taste at the time of use and after the finish. .

The softening effect of the liquid softener composition of the present invention is almost the same as that of di-hardened tallow alkyldimethylammonium chloride which has been widely used in the past, but surprisingly, the softness of elasticity is low. It turned out to be obtained.

[0024]

Industrial Applicability The softening agent of the present invention can impart sufficient flexibility and antistatic properties to various fibers, can provide excellent elasticity, is excellent in biodegradability, and has storage stability. Is also excellent.

[0025]

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

Production Example C ₁₈ H ₃₇ —O— (CH ₂ CH ₂ O) ₅ —CH ₂ COOH 548 g (1 mol)

[0027]

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66 g (0.5 mol) were mixed, and the mixture was stirred under a nitrogen stream.
The mixture was heated and stirred at 170 ° C. and 10 Torr for 8 hours to obtain 498 g of the desired product. Various amine compounds were produced in the same manner to produce neutralized or quaternized products, which were used in the following Examples and Comparative Examples. The compounds used are shown in Table 1 below.

[0029]

[Table 1]

Examples 1 to 10 and Comparative Example 1 Liquid soft finish compositions having the formulations shown in Table 2 were prepared, and the elasticity of each composition was evaluated by the following method.

<Evaluation of elasticity> (1) Treatment method 3.5 kg of commercially available cotton towel 2 kg and acrylic jersey 1 kg
After washing 5 times (30 liter washing machine) repeatedly with a commercially available detergent attack (manufactured by Kao Corporation, registered trademark) in DH hard water to remove the fiber treating agent attached to each fiber, Table 2
1.5 g as an active ingredient was added at 25 ° C.
Treated with stirring for 1 minute. In each case, 1% by weight of the polyoxyethylene-modified dimethylpolysiloxane was added to the total amount of the compound according to the present invention.

(2) Evaluation Method The cloth treated by the above method was air-dried in a room, and then left in a constant temperature and humidity room at 25 ° C. and 65% RH for 24 hours. These fabrics were evaluated for elasticity. The elasticity was evaluated by comparing one pair with a fabric treated with 10 cc of a softener comprising 15% by weight of dihydrogenated tallow alkyldimethylammonium chloride. The evaluation is expressed as follows. +2; more elastic than control +1; slightly more elastic than control 0; same as control -1; slightly less elastic than control -2; less elastic than control

[0033]

[Table 2]

Examples 11 to 13 and Comparative Example 2 To evaluate the elasticity of the compositions having the compositions shown in Table 3, the pile height of cotton towels was measured. <Evaluation of Elasticity> Cotton towels treated in the same manner as in Examples 1 to 10 were folded in eight, three sheets were piled up, and 5 g / cm ^2.
After 5 minutes of pressurizing, the pressure was removed and the height of the towel was measured. The higher the height of the towel, the better the elasticity.

[0035]

[Table 3]

──────────────────────────────────────────────────続 き Continued on the front page (58) Field surveyed (Int.Cl. ⁷ , DB name) D06M 13/00-13/535

Claims (1)

(57) [Claims] 1. An acid-neutralized or quaternized product of an amine represented by the general formula (I) and / or an acid-neutralized or quaternized product of an amine represented by the general formula (II) as an essential component Liquid soft finish composition characterized by containing. Embedded image [Wherein, R ₁ and R ₂ represent a straight-chain or branched saturated or unsaturated hydrocarbon group having 8 to 24 carbon atoms, and R represents a straight-chain or branched saturated or unsaturated hydrocarbon having 8 to 24 carbon atoms. A group, a hydroxyethyl group or a hydroxypropyl group, m and n represent an integer of 2 to 6, and p and q represent an integer of 1 to 20. [Chemical formula 2] [In the formula, R ₃ and R ₄ represent a straight-chain or branched saturated or unsaturated hydrocarbon group having 8 to 24 carbon atoms, and r represents an integer of 1 to 20. ]