JP6049193B2 - Textile softener - Google Patents

Description

  The present invention relates to a textile softener comprising a specific polymer and a softener composition containing the same.

  Currently, commercial products that are marketed as household softeners are based on tertiary amines or quaternary ammonium salts having two long-chain alkyl groups. In addition to the above-mentioned molecules, substances having a flexibility-imparting effect are known for various substances, and among them, a high-molecular polymer composed of a monomer having a specific structure having a cationic group imparts high flexibility. It has been proposed to have an effect. Patent Document 1 discloses a softener composition that provides an excellent softening effect by using a polymer compound having a structural unit derived from a polymerizable compound having an amino group and a cationic compound in combination. Patent Document 2 describes a softener composition that uses a polymer compound derived from an acrylic acid compound containing acrylamide in the general formula as a soft base material.

JP 2008-144316 A JP 2012-154010 A

  The prior art is a polymer compound containing a monomer unit having an amide group or the like as a constituent unit, but as other monomer units copolymerized, a cationic group such as an amine, a quaternary ammonium group, or a phosphonium group is used. The structure derived from the monomer which has. However, a softening agent using a high molecular polymer having a cationic group as a softening agent for a textile product has a problem in that it adheres to the fiber, thereby imparting flexibility while causing stickiness.

  In response to this problem, the present inventors have a substantially cationic monomer structure unit having a specific structure having a hydrophilic group and a structural unit derived from a monomer having an ester group in the structure of the polymer compound. It has been found that a polymer having no group and a softener composition containing the same can unexpectedly suppress not only the effect of imparting flexibility to a fiber product but also stickiness after treatment.

That is, the gist of the present invention is as follows.
[1] A structural unit (a-1) derived from a nonionic monomer (monomer 1) having a polymerizable unsaturated bond, an ester group, and a hydrocarbon group having 8 to 30 carbon atoms bonded to the ester group;
A structural unit derived from a nonionic monomer (monomer 2) having a polymerizable unsaturated bond and having one or more organic groups selected from the group consisting of a polyoxyethylene group, an amide group and a dimethylamide group (a-2 )
A textile softener comprising a polymer composed of a structural unit containing at least
Among all the structural units of the polymer, the structural unit (a-1) occupies 30 mol% or more and 90 mol% or less, the structural unit (a-2) occupies 10 mol% or more and 50 mol% or less, and the structural unit Textile softening agent comprising a polymer having a total of (a-1) and the structural unit (a-2) of 70 mol% or more and 100 mol% or less and further having no cationic group in the molecule And [2] a softener composition comprising as a component (A) a fiber product softener comprising the polymer according to [1].

  The textile softener and the softener composition containing the same of the present invention are compared with the textile softener and the softener composition containing the textile softener comprising a polymer having a cationic group. The sticky feeling on the textile product can be reduced.

  The polymer (which may be referred to as “component (A)” hereinafter), which is the textile softener of the present invention, will be described.

<(A) component> Textile softening agent As the textile softening agent (component (A)), a polymerizable unsaturated bond, an ester group, and a hydrocarbon group having 8 to 30 carbon atoms bonded to the ester group are used. One or more selected from the group consisting of a structural unit (a-1) derived from a nonionic monomer (monomer 1) having a polymerizable unsaturated bond and a polyoxyethylene group, an amide group, and a dimethylamide group A high molecular weight polymer composed of a structural unit containing at least a structural unit (a-2) derived from a nonionic monomer (monomer 2) having an organic group, and further having a cationic group substantially in the molecule It is a high molecular polymer that does not have. Examples of the cationic group include a primary to tertiary amino group, a quaternary ammonium group, and a phosphonium group, and a tertiary amino group and a quaternary ammonium group are preferable. Examples of the tertiary amino group or quaternary ammonium group include dialkylamino groups such as dimethylamino group, diethylamino group, dipropylamino group, diisopropylamino group, dibutylamino group, dit-butylamino group, pyridine group, and imidazole. And quaternary ammonium groups in which a methyl group or an ethyl group is bonded to the amino group.

  In the present invention, the high molecular polymer of the component (A) does not substantially contain a cationic group. This allows the inclusion of trace amounts of cationic groups to the extent that they do not affect the effect of the present invention. For example, the case where it mixes in a trace amount in the preparation process of an impurity or another essential monomer is mentioned. Specifically, the structural unit having a cationic group is preferably 0.5 mol% or less, more preferably 0.1 mol% or less, in the polymer.

1. Structural unit (a-1)
As the structure of the structural unit (a-1), those represented by the following general formula (1) are preferable.

In the formula, R ¹ is —H or —CH ₃ , and R ² is a C _{10 to} C ₂₄ hydrocarbon group, preferably a C _{10 to} C ₂₄ alkyl group, more preferably a C _{10 to} C ₂₄ linear chain. It is an alkyl group. From the viewpoint of imparting flexibility, R ² is a hydrocarbon group, preferably an alkyl group, more preferably a linear alkyl group. 8-24 is preferable as the carbon number of R ^2, more preferably from 12 to 24, more preferably 14 to 24.

  In order to introduce the structural unit (a-1) into the polymer according to the present invention, for example, an ester of acrylic acid and an aliphatic alcohol or an ester of methacrylic acid and an aliphatic alcohol is used as a monomer component. It is preferable. Specific examples of the monomer include lauryl methacrylate, lauryl acrylate, myristyl acrylate, myristyl methacrylate, cetyl acrylate, cetyl methacrylate, stearyl acrylate, stearyl methacrylate, and the like.

  The amount occupied by the structural unit (a-1) in all the structural units of the polymer is 30 mol% or more, preferably 35 mol% or more, more preferably 40 mol% or more, from the viewpoint of imparting flexibility. And from a soluble viewpoint to water, it is 90 mol% or less, Preferably it is 70 mol% or less, More preferably, it is 60 mol% or less.

2. Structural unit (a-2)
As the structure of the structural unit (a-2), those represented by the following general formula (2) are preferable from the viewpoint of solubility in water.

In the formula, R ³ is —H, —OH or —CH ₃ , and R ⁴ is —CONH ₂ , —CON (CH ₃ ) ₂ or — (X) _m (CH ₂ CH ₂ O) _n R ⁵ . . n is an average of 5 or more and 20 or less, preferably 15 or less, and R ⁵ is —H or —CH ₃ . m is a number of 0 or 1, and when m is 1, X is —O—, —C (═O) O— or —CONH—. In particular, by having a polyoxyethylene group in the structural unit (a-2), water can be mainly used as the solvent of the component (B). Specifically, the solvent of the component (B) is 90 Water can be used at a rate of at least%.

  In order to introduce the structural unit (a-2) into the polymer according to the present invention, as a monomer component, for example, polyoxyethylene methacrylate (average added mole number of oxyethylene group is 5 to 20 moles, preferably 5 to 15 mol), polyoxyethylene acrylate (average added mole number of oxyethylene group is 5 to 20 mol, preferably 5 to 15 mol), acrylamide, methacrylamide, N, N-dimethylacrylamide, N, N-dimethyl It is preferable to use methacrylamide, vinyl alcohol or the like.

  The amount occupied by the structural unit (a-2) in all the structural units of the polymer is 10 mol% or more, preferably 20 mol% or more, more preferably 30 mol% or more from the viewpoint of solubility in water. And from the viewpoint of imparting flexibility, it is 50 mol% or less, preferably 45 mol% or less, more preferably 40 mol% or less.

  Among all the structural units of the polymer, the total of the structural unit (a-1) and the structural unit (a-2) is 70 mol% or more, preferably 75 mol% or more, more preferably from the viewpoint of imparting flexibility. Is 80 mol% or more, and from the viewpoint of storage stability, it is 100 mol% or less, preferably 95 mol% or less, more preferably 90 mol% or less.

4). Structural unit (a-3)
As the structural unit of the polymer, in addition to the structural unit (a-1) and the structural unit (a-2), the monomer from which these structural units are derived, that is, both the monomer 1 and the monomer 2 are the same. It may further contain a structural unit (a-3) derived from a polymerizable monomer. However, the structural unit (a-3) has substantially no cationic group as described above. The cationic group in the structural unit (a-3) is that mentioned in the description of the component (A).

  As a preferred structure of the structural unit (a-3), structural units derived from anionic monomers and structural units derived from nonionic monomers other than the general formula (1) and general formula (2) can be raised. In the present invention, a structural unit derived from a monomer having a carboxylic acid group is preferred from the viewpoint of storage stability. Specifically, what is represented by the general formula (3) is a preferred example of the structural unit (a-3).

In the formula, R ⁶ is —H, —COOH or —CH ₃ , and R ⁷ is —COOH. When R ⁶ or R ⁷ is —COOH, —COOH may be in the form of a salt, for example, sodium salt, potassium salt or ammonium salt.

  In order to introduce the structural unit (a-3) into the polymer according to the present invention, as the monomer component, for example, an anionic monomer of unsaturated carboxylic acid, such as acrylic acid, methacrylic acid and maleic acid, etc. It can be achieved by using. The proportion of the structural unit represented by the general formula (3) in the structural unit (a-3) is preferably 90 mol% or more, more preferably 100 mol%.

  The amount occupied by the structural unit (a-3) in all the structural units of the polymer is not particularly limited, but from the viewpoint of storage stability, it is preferably 1 mol% or more, more preferably 5 mol% or more, and still more preferably. Is 10 mol% or more, and from the viewpoint of imparting flexibility, it is preferably 30 mol% or less, more preferably 25 mol% or less, and still more preferably 20 mol% or less.

  Each ratio of the structural unit in the polymer may be determined by analyzing the polymer, or may be a molar ratio of monomers used during polymerization.

  In the present invention, the polymer obtained by restricting the cationic group and the softener composition containing the polymer can suppress stickiness or tackiness of the fiber product after the soft treatment.

5. (A) Manufacturing method of component (A) A component can be manufactured, for example with the following method.
A monomer component that provides the structural unit (a-1), a monomer component that provides the structural unit (a-2), and a monomer component that provides the structural unit (a-3) as necessary, in a suitable solvent, for example, Dissolve in acetone, methanol, ethanol, propanol, isopropyl alcohol, etc. Next, an initiator dissolved in the same solvent, for example, 2,2′-azobis (2,4-dimethylvaleronitrile) (V-65; manufactured by Wako Pure Chemical Industries, Ltd.) is mixed with the monomer mixture. . The concentration of the monomer component and the initiator can be appropriately set by those skilled in the art.

  Subsequently, after stirring and holding the mixture of a monomer component and an initiator at an appropriate temperature and time, for example, 3 to 5 hours at 50 to 100 ° C., the solvent is distilled off under reduced pressure and concentrated. Thereafter, an initiator dissolved again in a solvent, for example, 2,2′-azobis (2,4-dimethylvaleronitrile) (V-65; manufactured by Wako Pure Chemical Industries, Ltd.) is added, and 50 to 100 ° C. Stir these mixtures under reduced pressure for 3-5 hours. Then, the (A) component which is a target high molecular polymer can be obtained by drying under reduced pressure at 80 degreeC for 1 day, for example.

The molecular weight of the component (A) is preferably 1,000 or more and 1,000,000 or less, more preferably 5000 or more and 100,000 or less as a weight average molecular weight. The molecular weight can be measured, for example, by gel filtration chromatography (GPC) under the following conditions.
Apparatus: HLC-8120 manufactured by Tosoh Corporation
GPC column: TSKgel α-M (1) manufactured by Tosoh Corporation
Eluent: 60 mmol / LH3PO4, 50 mmol / LiBr / DMF
Flow rate: 1.0 ml / min
Column temperature: 40 ° C
Detector: RI

In the softener composition of the present invention, it is preferable to use the component (A) excellent in water dispersibility for use in household use, for example, textile products. ) is, in the above formula (1), R ² is a linear alkyl group having 14 to 18 carbon atoms, the carbon atoms of the alkyl group which alkyl group and the carbonyl carbon is bonded is a primary carbon atom configuration And the structural unit (a-2) is the above general formula (2), wherein R ⁴ is — (X) _m (CH ₂ CH ₂ O) _n R ⁵ , and X is —O— or -C (= O) O-, wherein n is a structural unit having an average number of 6 to 12, and the proportion of the structural unit (a-1) is 30 mol% or more in all the structural units of the polymer. Preferably 40 mol% or more and 90 mol% or less, preferably 70 mol% or less, more preferably 60 mol% or less. The proportion of the unit (a-2) is 10 mol% or more, preferably 30 mol% or more, and 50 mol% or less, preferably 40 mol% or less, in all the structural units of the polymer, and the structural unit (a -1) and the structural unit (a-2) are 70 mol% or more, preferably 80 mol% or more of the total structural units of the polymer, and the proportion of the structural unit (a-3) is the polymer weight. It is a high molecular weight polymer that preferably accounts for 5 mol% or more and preferably 30 mol% or less of all structural units of the coalescence. The average molecular weight of the polymer used in the softener composition of the present invention is preferably 5000 to 100,000.

  Such a polymer is easy to disperse in water and easy to handle. A polymer that is difficult to disperse in water can be used as a component (B) by dissolving it in a lipophilic organic solvent, but there is also a method of dispersing it in an aqueous solvent in combination with a nonionic surfactant.

  The present invention also provides an invention of a softener composition using the above polymer as a soft base material as the component (A). The component (A) may be contained in the composition at an arbitrary concentration, but when the softening treatment is performed, the treatment containing the component (A) is sufficient to bring the component (A) into sufficient contact with the fiber product. It is necessary to prepare the liquid. Therefore, since the component (A) needs to enhance the dispersion or solubility in the solution, it contains a solvent such as water, an organic solvent, a powdering aid or a dispersion medium (hereinafter also referred to as component (B)). It is preferable to use it as a softener composition.

<(B) component>
(B) component in the softening agent composition of this invention is a medium for disperse | distributing or melt | dissolving the high molecular polymer of (A) component which is a soft base material in a liquid state. Component (B) may be an aqueous solvent such as water or a water-soluble organic solvent, or may be an oleophilic organic solvent, but an aqueous solvent is preferred from the viewpoint of safety during use. Further, it can be used as a powder softener composition, and in that case, a powdering aid for powdering can be used. (B) A component may be 1 type and a 2 or more types of mixture may be sufficient as it.

  Water-soluble organic solvents used for the liquid softener composition include ethanol, isopropanol, acetone, ethylene glycol, diethylene glycol, dipropylene glycol, di- or triethylene glycol mono short chain alkyl (2 to 6 carbon atoms) ether, Examples thereof include phenoxyethanol and polyethylene glycol phenyl ether having 1 to 3 moles of ethylene oxide added. Examples of the lipophilic organic solvent include hexane, acetone, toluene, xylene and the like.

  As described above, in the present invention, it is preferable to mainly use water as the component (B), and it is more preferable that water accounts for 90% by mass or more of the component (B). In this case, it is preferable to use those having a polyoxyethylene group in the constitution as part or all of the structural unit (a-2) constituting the high molecular polymer of the component (A).

  It is also possible to use the softener composition of the present invention as a powder or a granular material. In that case, powdered cellulose, clay, sulfate powder and other powdering aids, and if necessary, mixed or granulated with a binder such as polyethylene glycol or glycerin, the powder of the polymer (A) diluted and dispersed Can be obtained. The powdery or granular softener composition can be used by dissolving or dispersing in water at the time of use.

<(C) component>
The softener composition of the present invention may contain a surfactant as the component (C). As the surfactant, it is preferable to use a nonionic surfactant. For example, a polyoxyethylene alkyl ether in which the alkyl group has 10 to 18 carbon atoms, the alkyl group is derived from a primary alcohol or a secondary alcohol, and the average added mole number of ethylene oxide is 3 to 50 mol. Can be used. Polyoxyethylene / polyoxypropylene alkyl ether in which propyleneoxy groups are introduced by adding propylene oxide in a ratio of 1 to 3 mol in a block or random manner in addition to ethylene oxide may be used.

<Other ingredients>
The softening agent composition of the present invention can be used in combination with the techniques and components described in the patent documents and non-patent documents of the field of the present invention so far as the effects are not impaired. For example, in addition to the above components, silicone, antibacterial / antifungal agents, dyes / pigments, fragrances and the like can be contained. About a fragrance | flavor, the composition intended to remain in a fiber for a deodorizing effect may be sufficient, and generation | occurrence | production of odor from clothing may be suppressed using an antibacterial fragrance | flavor.

  One feature of the softener composition of the present invention is that the softening effect can be achieved without blending the conventional cationic surfactant used in the technical field of the present invention. Examples of the cationic surfactant include those conventionally known as a soft component in the field of the present invention.

  The softener composition of the present invention may or may not contain such a cationic surfactant. When such a cationic surfactant is included, from the viewpoint of maintaining the texture unique to the polymer, the amount of the cationic surfactant in the softener composition of the present invention is [cationic surfactant] / [Component (A)] is preferably within the range of the mass ratio of more than 0/100 and not more than 50/50, more preferably not less than 10/90, and more preferably not more than 30/70.

  In addition, although an anionic surfactant may be mix | blended to such an extent that the effect of this invention is not reduced, it is preferable not to contain substantially. Specifically, 50 ppm or less of the softening agent composition of the present invention is preferable.

<Softener composition>
The softener composition of the present invention is a softener composition containing at least component (A) and component (B). The properties of the composition of the present invention may be liquid, powder or granular, but are preferably liquid at normal temperature. The case of liquid will be described below.

  The amount of the component (A) in the composition of the present invention is preferably 0.001% by mass or more, more preferably 0.01% by mass or more, and still more preferably from the viewpoint of imparting flexibility to the fiber product or the like. From the viewpoint of the viscosity of the composition, it is preferably 10% by mass or less, more preferably 5% by mass or less, and further preferably 1% by mass or less.

  The amount of the component (B) in the composition of the present invention is preferably 80% by mass or more, more preferably 85% by mass or more, and further preferably 90% by mass or more, from the viewpoint of the viscosity of the composition. From the viewpoint of the amount, it is preferably 99.9% by mass or less, more preferably 99% by mass or less, and still more preferably 95% by mass or less.

  Examples of a method for softening a fiber product using the softener composition of the present invention include a method of immersing the fiber product in a stock solution or a diluted solution of the softener composition, or a method of using the composition in a container with a sprayer. There are methods such as filling a stock solution or diluted solution, spraying the fiber product, and drying. Alternatively, the stock solution or diluent of the composition can be added to the washing machine rinsing step to impart flexibility to the textile.

  Hereinafter, the present invention will be described in more detail based on examples and the like, but the present invention is not limited only to such examples.

<Manufacturing method>
Synthesis example 1
A separable flask having a nitrogen introduction tube was previously purged with nitrogen, and there was 120.0 g of stearyl methacrylate and polyoxyethylene methacrylate having an average added mole number of ethylene oxide of 9 (manufactured by Shin-Nakamura Chemical Co., Ltd., product) Name: AM-90G) A solution in which 165.0 g, 15.0 g of methacrylic acid and 440.0 g of acetone were mixed was charged, and the temperature was raised until the temperature in the flask reached 60 ° C. or higher. Thereafter, a solution of 3.0 g of initiator V-65 dissolved in 6.0 g of acetone was added and stirred for 10 minutes.

  Subsequently, 280.0 g of stearyl methacrylate, 385.0 g of the same polyoxyethylene methacrylate, 35.0 g of methacrylic acid, 7.0 g of initiator V-65, and a solution at 60 ° C. mixed with 1050.0 g of acetone were mixed with 3 After dropping into the flask over time, polymerization was carried out by stirring and holding for 3 hours.

  After completion of the polymerization, acetone as a solvent was distilled off under reduced pressure and concentrated, and again a solution in which 5.0 g of initiator V-65 and 10.0 g of acetone were mixed was added. After sufficiently stirring, the mixture was concentrated to a polymer bulk and heated and stirred under reduced pressure conditions at 65 ° C. for 6 hours.

  After completion of the polymerization, the solvent was distilled off under reduced pressure, and the polymer was obtained by drying under reduced pressure at 80 ° C. for 1 day. This polymer is a ternary polymer composed of stearyl methacrylate, polyoxyethylene methacrylate and methacrylic acid, and the constituent units in the polymer are 41.5 mol% and 38. They were 7 mol% and 19.8 mol%. These correspond to the structural unit (a-1), the structural unit (a-2), and the structural unit (a-3), respectively. Moreover, the weight average molecular weight of this high molecular weight polymer was 78,000.

The weight average molecular weight of the high molecular weight polymer was measured under the following conditions using gel permeation chromatography.
Apparatus: HLC-8120 manufactured by Tosoh Corporation
GPC column: TSKgel α-M (1) manufactured by Tosoh Corporation
Eluent: 60 mmol / LH3PO4, 50 mmol / LiBr / DMF
Flow rate: 1.0 ml / min
Column temperature: 40 ° C
Detector: RI

Synthesis example 2
A separable flask having a nitrogen inlet tube was previously purged with nitrogen, and a solution in which 48.0 g of lauryl methacrylate, 12.0 g of N, N-dimethylacrylamide, and 84.8 g of ethanol were mixed was prepared. The temperature was raised to 60 ° C or higher. Thereafter, 1.5 g of initiator V-65 was added with an initiator solution in which 5.0 g of ethanol was uniformly dissolved, and the mixture was stirred and held for 6 hours for polymerization.

  The polymer solution was cooled to room temperature, purified by reprecipitation with acetone, and dried at 80 ° C. under reduced pressure to obtain a polymer. This polymer is a binary polymer composed of lauryl methacrylate and N, N-dimethylacrylamide, and the constituent units in the polymer are 60.9 mol% and 39. It was 1 mol%. These correspond to the structural unit (a-1) and the structural unit (a-2), respectively. Further, the weight average molecular weight of the polymer was 107,000.

The weight average molecular weight of the high molecular weight polymer was measured under the following conditions using gel permeation chromatography.
Apparatus: HLC-8120 manufactured by Tosoh Corporation
Column: KF-806L + KF-806L
Eluent: 60 mmol / LH3PO4, 50 mmol / LiBr / DMF
Flow rate: 1.0 ml / min
Column temperature: 40 ° C
Detector: RI

Synthesis example 3
A separable flask having a nitrogen introducing tube was previously purged with nitrogen, and a solution in which 38.1 g of lauryl methacrylate, 23.5 g of N, N-dimethylaminoethyl methacrylate, and 200 g of ethanol were mixed was prepared. A solution prepared by dissolving 2.5 g of V-65 in 40 g of acetone was added. Subsequently, it heated up until the temperature in a flask became 60 degreeC or more, and was hold | maintained as it was for 2 hours. The temperature was further raised to 70 ° C. and held for 6 hours.

  After this, ethanol was added to dilute and cool. The solution was purified by reprecipitation by dropping it into ion-exchanged water and dried under reduced pressure at 70 to 80 ° C. to obtain a polymer. This polymer is a binary polymer composed of lauryl methacrylate and N, N-dimethylaminoethyl methacrylate, and the constituent units in the polymer are calculated to be 50.0 mol. % And 50.0 mol. %Met. These correspond to the structural unit (a-1) and the structural unit (a-2), respectively. Further, the weight average molecular weight of the polymer was 9,500.

The weight average molecular weight of the high molecular weight polymer was measured under the following conditions using gel permeation chromatography.
Equipment: HLC-8120 manufactured by Tosoh Corporation
GPC column: TSKgelα-M (one) manufactured by Tosoh Corporation
Eluent: Dimethyl sulfoxide (50 mM potassium bromide)
Flow rate: 0.5mL / min
Column temperature: 50 ° C
Detector: RI

<Preparation of softener composition>
Examples 1 to 3 and Comparative Example 1
Using each polymer obtained by the above production method, four types of polymer dispersions shown in Table 1 were prepared as a softener composition. However, Example 3 is a reference example. A polymer dispersion was prepared by adding 150 ml of the component (B), that is, each of the components b-1 to b-4, to 0.375 g of the polymer obtained by the above production method.

  For Example 1, the following operation was performed. 150 ml of water was added to 0.375 g of the polymer, and the solvent was raised to 60 ° C. and kept stirring for 10 minutes. Thereafter, the mixture was kept stirred for 10 minutes at room temperature. By repeating this operation, a polymer aqueous dispersion was obtained.

b-1: water
b-2: Acetone
b-3: Isopropanol / hexane = 7/3 vol%
b-4: Hexane

<Flexible processing method>
A commercially available towel, that is, 100% cotton, a size of about 34 cm × 82 cm, and a basis weight of about 75 g / sheet was prepared. Prepare a 10 wt% dispersion of lauryl alcohol ethylene oxide 8 mol adduct as a surfactant for washing, wash the cotton towel twice in a fully automatic washing machine, and then rinse thoroughly and dry with a household electric dryer The test cloth was used as a test cloth.

  Next, 150 ml of the polymer dispersion prepared by the above method was filled in a spray bottle and sprayed on a towel. The sprayed towel was dried under the conditions of 23 ° C. and 40% RH, and then evaluated for flexibility and stickiness in a standard test room (20 ° C., 65% RH).

<Flexible performance evaluation>
For the evaluation of the flexible performance, six skilled testers made a pair comparison using the reference cloth as a reference, and evaluated based on the following criteria, and the average value of the evaluations of the six was used as the evaluation value. As a control cloth, a towel was used which was rinsed with deionized water and dried under the same conditions without spraying the polymer dispersion.

+2: Softer than the control.
+1: Slightly softer than the control.
0: Equivalent to control.
-1: Slightly higher than the control.
-2: Harder than control.

<Stickness evaluation>
For the stickiness evaluation, six skilled testers made a pair comparison using the above-mentioned control cloth as a reference, and evaluated based on the following criteria. The average value of the six evaluations was used as the evaluation value.

+2: Not sticky than the control.
+1: A little sticky than the control.
0: Equivalent to control.
-1: Slightly sticker than the control.
-2: Sticky than the control.

  It turned out that Examples 1-3 which used the thing in which the high molecular polymer is in the range of the present invention are superior to Comparative Example 1 in terms of flexibility and stickiness. From the comparison between Example 3 and Comparative Example 1, it was found that Comparative Example 1 was clearly lower in terms of flexibility and stickiness.

  The structural unit is structural unit (a-1), structural unit (a structural unit (a-1) and structural unit (a-2) rather than Example 3 using a polymer having two types of structural units (a-1) and (a-2) It was found that Example 1 and Example 2 using the high molecular polymers that are three types of a-2) and structural unit (a-3) are more excellent in terms of flexibility.

  The textile product softening agent and the softening agent composition containing the same of the present invention can be used as a softening agent capable of imparting flexibility to the textile product.

Claims (6)

A structural unit (a-1) derived from a nonionic monomer (monomer 1) having a polymerizable unsaturated bond, an ester group and a hydrocarbon group having 8 to 30 carbon atoms bonded to the ester group;
A structural unit derived from a nonionic monomer (monomer 2) having a polymerizable unsaturated bond and having one or more organic groups selected from the group consisting of a polyoxyethylene group, an amide group and a dimethylamide group (a-2 ) And
As a structural unit of the polymer, a structural unit (a-3) derived from a monomer copolymerizable with both the monomer 1 and the monomer 2 (provided that the structural unit (a-3) has a cationic group. No.)
Is a textile softening agent comprising a polymer composed of a structural unit containing at least a structural unit, wherein the structural unit (a-2) has a structure represented by the general formula (2):

(Wherein, R ³ is -H, -OH or -CH _3, R ⁴ is _{-CONH 2, -CON (CH 3)} 2 or - (X) with _{m (CH 2 CH 2 O)} n R 5 N is an average number of 5 or more and 20 or less, R ⁵ is —H or —CH ₃ , m is a number of 0 or 1, and when m is 1, X is —O—, — C (= O) O- or -CONH-.)
The structure of the structural unit (a-3) is represented by the general formula (3):

(Wherein, R ⁶ is —H, —COOH or —CH ₃ , and R ⁷ is —COOH). Among all the structural units of the polymer, the structural unit (a -1) occupies 30 mol% or more and 70 mol% or less, the structural unit (a-2) occupies 10 mol% or more and 50 mol% or less, and the structural unit (a-1) and the structural unit (a-2) The fiber product softening agent which consists of a high molecular polymer which is 70 mol% or more and 95 mol% or less, and does not have a cationic group in a molecule | numerator. The structural unit (a-3) is a structural unit derived from anionic monomers, the polymeric polymer 5 mol% or more of all the structural units of account for less 30 mol%, the polymer weight according to claim 1 Textile softener made of coalescence. The structure of the structural unit (a-1) is represented by the general formula (1):

(In the formula, R ¹ is —H or —CH ₃ , and R ² is a C _{10 to} C ₂₄ hydrocarbon group.)
The textile softener which consists of a high molecular polymer of Claim 1 or 2 which is shown by these. The softening agent composition which contains the textile softening agent which consists of a high molecular polymer of any one of Claims 1-3 as (A) component. The softening agent composition according to claim 4 , further comprising a dispersion medium or a solvent as the component (B). A cationic surfactant in an amount that does not contain a cationic surfactant or satisfies the range of [cationic surfactant] / [component (A)] exceeding 0/100 and a mass ratio of 50/50 or less. The softening agent composition according to claim 4 or 5 , further comprising an agent.