JP3021998B2 - Soft finish - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a softening agent capable of imparting excellent water absorption to treated clothing.

[0002]

2. Description of the Related Art At present, most of commercially available softeners for home use are mainly composed of di (hardened tallowalkyl) dimethyl quaternary ammonium salt. Recently, amines having various linking groups or salts or quaternaries thereof have been disclosed (for example, JP-A-4-108173, JP-A-4-108174).

[0003] These quaternary ammonium salts and the like can impart good softening and antistatic effects to various fibers in a small amount. Since the softening effect due to this is manifested by a reduction in the friction coefficient of the fiber surface due to the lubricating effect of the lipophilic portion in the base molecule adsorbed on the fiber surface, in order to achieve an excellent softening effect,
A lipophilic nature is considered essential. However,
This lipophilic property has the disadvantage of making the treated garment water repellent and lowering its water absorption, especially when the softener concentration is high, a marked reduction in water absorption is observed.

In order to improve water absorption from such a viewpoint,
Flexible bases are being studied. Dioleyldimethyl quaternary ammonium salt is known as one of the soft bases having excellent water absorption (see JAOCS, vol. 60, No. 6, pages 1166 to 1169). However, soft finishes using the base are:
Compared to di (hardened tallow alkyl) dimethyl quaternary ammonium salt, it has excellent water absorption, but is inferior in flexibility. Therefore, when used in combination with another soft base such as di (hardened tallow alkyl) dimethyl quaternary ammonium salt in order to increase the softness, the water absorption is deteriorated.

[0005]

In view of such circumstances, the present inventors have diligently sought to find a flexible base having better water absorption and flexibility than conventional dioleyl quaternary ammonium salts. As a result of the research, by using an amine having a specific non-identical long-chain alkyl group or a neutralized product or quaternized product thereof as an essential component of the soft finish composition, sufficient softness performance is obtained, and water absorption performance is also improved. The present invention was found to be significantly improved, and the present invention was completed.

That is, the present invention provides the following general formulas (1) to (3)
A soft finish containing one or more of the amine compound represented by the formula (1) or a neutralized product or a quaternized product thereof as an essential component.

[0007]

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[Wherein, R ¹ and R ² ; one of them is a saturated hydrocarbon group having 11 to 21 carbon atoms, and the other is an unsaturated hydrocarbon group or a carbon number of 11 to 21 carbon atoms.
Represents a branched hydrocarbon group having 11 to 21 or a hydroxy-substituted hydrocarbon group having 11 to 21 carbon atoms.

M, n: represents 2 to 5.

R ³ represents an alkyl group having 1 to 4 carbon atoms. ].

The compound represented by the general formula (1) according to the present invention is obtained by reacting the following amine compound (1-A) with an equimolar amount of an ester such as R ¹ COOH or R ¹ COOCH ₃ at 150 to 160 ° C. To give a compound (1-M), and then (1-M) is mixed with an equimolar amount of an ester such as R ² COOH or R ² COOCH ₃ for 160-150.
It can be subjected to a condensation reaction (esterification) at 180 ° C. This reaction is shown below.

[0012]

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The compound represented by the general formula (2) according to the present invention is obtained by nitriding R ¹ COOH and hydrogenating to obtain R ¹ CH ₂ NH ₂ and then adding ethylene oxide to obtain the following compound (2) -M)

[0014]

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Can be obtained by esterification in the same manner as described above. The compound represented by the general formula (3) according to the present invention is obtained by obtaining the following amine (3-A) via (3-M) in the same manner as in the case of the compound represented by the formula (1). Can be.

[0016]

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The compounds represented by the general formulas (1) to (3) are those wherein R ² in the general formulas (1) to (3) is a saturated hydrocarbon and R ¹ is an unsaturated or branched or hydroxy-substituted hydrocarbon. It is preferred that The reason is, both compounds are the R ² of is bonded to an ester group, when R ² is a saturated hydrocarbon, in the case of hydrolyzed during long-term storage, part of free fatty acid (R ² COOH) becomes a saturated fatty acid, and the odor deterioration by the free fatty acid is less in the case of the saturated fatty acid. The compounds represented by the above general formulas (1) to (3) according to the present invention may include compounds produced as by-products in the production process and unreacted raw materials.
Therefore, although some compounds have different carbon numbers and different kinds of hydrocarbon groups as impurities, the carbon number of the main component only needs to be 11 to 21.

The starting materials R ¹ COOH and R ² CO
As OH, fatty acids obtained by decomposing and refining natural fats and oils such as beef tallow, palm oil, sunflower oil, safflower oil, olive oil, and rapeseed oil are inexpensive and advantageous. Specific acids include palmitic acid, stearic acid, eicoic acid, isostearic acid, oleic acid, erucic acid, elaidic acid, brassic acid, 12-hydroxystearyl acid and the like.

When R ¹ or R ² is an unsaturated hydrocarbon group, the stereoisomeric structure of the unsaturated bond group is preferably at least 3% by weight in the trans form, particularly preferably in the cis form.
Those containing 25 to 97% by weight and a trans form of 3 to 75% by weight are preferred. The ratio between the cis form and the trans form can be easily obtained from the integral ratio of olefin protons using NMR.

In addition, R ¹ is generally derived from natural fats and oils, but usually, other than those having only one unsaturated bonding group,
Those having two or more unsaturated bonding groups coexist. However, the content of those having two or more unsaturated bonding groups is preferably 5% or less.

The acids for obtaining the neutralized products of the amine compounds represented by the general formulas (1) to (3) include inorganic acids such as hydrochloric acid, nitric acid, phosphoric acid and sulfuric acid, acetic acid, lactic acid and glycolic acid. And organic acids having 6 or less carbon atoms, such as citric acid and maleic acid. Hydrochloric acid is the cheapest and has high performance. Also, the general formula
The quaternized amine compounds represented by (1) to (3) can be obtained by a known method using dialkyl sulfate such as methyl chloride or dimethyl sulfate.

In the soft finish of the present invention, the above-mentioned amine compound or its neutralized product or quaternized product, which is a feature of the present invention, is preferably incorporated in a total amount of 3 to 30% by weight. The balance of the softening agent of the present invention is an optional component and water.

For the purpose of further improving the flexibility and water absorption of the softening agent of the present invention, dimethylpolysiloxane or a modified product thereof may be added at a ratio of 0.2 to 5% by weight based on the compound of the present invention. it can. Conventionally, silicon has been known as a base which is added to a soft finish to improve its softness and ironing properties (see, for example, JP-A-52-53094). Silicon, as seen in these properties,
It itself has water repellency and is a base material that has a rather bad effect on water absorption performance. In the present invention, however, the fact that when used in combination with a specific unsaturated amine compound or a neutralized product or quaternized product thereof improves the water absorption performance, it is completely surprising contrary to conventional common sense.

Particularly preferred dimethylpolysiloxane or a modified product thereof has a viscosity at 25 ° C. of 20 to 10,000 cps.
Is appropriate. Modified products include polyoxyethylene modified products and amino modified products, and the modification rate is 10%.
The following is preferred. The dimethylpolysiloxane or a modified product thereof is desirably emulsified in advance using a polyoxyethylene-based nonionic activator or a monoalkylcation-based or dialkylcation-based cationic activator.

The soft finish of the present invention has a general formula
In addition to the amine compound represented by (1) to (3) or a neutralized or quaternized product thereof, polyoxyethylene alkyl or alkenyl ether, polyoxyethylene alkyl phenyl ether, Nonionic surfactants such as polyoxyethyleneoxypropylene polyalkylenepolyamine, higher fatty acids such as stearic acid and oleic acid, or partial esterified products of 2-ethylhexanoic acid and glycerin or pentaerythritol; salt, ammonium chloride, calcium chloride Water-soluble salts such as ethyl alcohol, isopropyl alcohol,
Solvents such as propylene glycol and ethylene glycol;
Urea, bactericides, antioxidants, pigments, dyes, fragrances and the like can be added.

The pH of the softening agent of the present invention is from 1 to 7, preferably from 1.5 to 6.0, from the viewpoint of stability during storage.

[0027]

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

Examples 1 to 11 and Comparative Examples 1 to 4 <Evaluation> (1) Softening method Commercially available cotton towel or cotton knitted underwear was repeated 5 times with a commercially available detergent Zab (manufactured by Kao Corporation, registered trademark). After washing and removing the detergent attached to the cloth, a 0.05% aqueous solution (3.5 DH hard water) of a softening agent shown in Table 1 at 25 ° C. and a bath ratio of 1 was used.
/ 30 under stirring for 5 minutes. (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 flexibility and water absorption. Softness A paired comparison was performed using a cloth treated with a control product (a dimethyldi-hardened tallow ammonium salt used as a standard soft material at 10%) as a control, and evaluated according to the following evaluation criteria. +2 Softer than control +1 Slightly softer than control 0 Same as control -1 Slightly softer than control -2 Softer than control Cut into strips, one end of which
Soak cm in water. The height of rise (cm) of water after 15 minutes was measured.

The soft bases of the soft finish used in the examples are shown in Table 1. Table 2 summarizes the mixing ratio of each component in each soft finish and the measurement results of the soft finish effect. From Table 2, it can be seen that in the case of the softening agent according to the present invention, sufficient flexibility is maintained and the water absorption is remarkably improved.

[0030]

[Table 1]

Note: * 1: 1-1, 1-2, and 3-1 are comparative products, and others are products of the present invention. * 2: The types of R ¹ and R ² have the following meanings. Saturated: saturated hydrocarbon group Unsaturated: unsaturated hydrocarbon group Branch: isostearic acid residue OH: 12-hydroxystearic acid residue * 3: Indicates the carbon number of the main component.

[0032]

[Table 2]

Note) 1): Dimethyl polysiloxane 2): Dimethyl di-hardened tallow alkyl ammonium chloride

Claims (3)

(57) [Claims] 1. A softening agent comprising one or more of amine compounds represented by the following general formulas (1) to (3) or neutralized or quaternized compounds thereof as essential components. Embedded image [Wherein, R ¹ , R ² ; one of them is a saturated hydrocarbon group having 11 to 21 carbon atoms, and the other is an unsaturated hydrocarbon group having 11 to 21 carbon atoms or carbon number.
Represents a branched hydrocarbon group having 11 to 21 or a hydroxy-substituted hydrocarbon group having 11 to 21 carbon atoms. m, n; represents 2 to 5. R ³ represents an alkyl group having 1 to 4 carbon atoms. ] 2. R ¹ or R ² is an unsaturated hydrocarbon group having 11 to 21 carbon atoms, and the ratio of its trans isomer is 3 to 75.
2. The softener according to claim 1, wherein the softener is in weight%. 3. The softener according to claim 1, wherein R ² is a saturated hydrocarbon group having 11 to 21 carbon atoms.