JP3820007B2

JP3820007B2 - Textile softener

Info

Publication number: JP3820007B2
Application number: JP25752497A
Authority: JP
Inventors: 克也藤本; 英之前田; 章本庄
Original assignee: Matsumoto Yushi Seiyaku Co Ltd
Current assignee: Matsumoto Yushi Seiyaku Co Ltd
Priority date: 1997-09-05
Filing date: 1997-09-05
Publication date: 2006-09-13
Anticipated expiration: 2017-09-05
Also published as: JPH1181137A

Description

【０００１】
【発明の属する技術分野】
本発明は、天然繊維及び合成繊維に有用な柔軟仕上げ剤及びその製造方法に関するものである。
【０００２】
【従来の技術】
代表的な脂肪酸アマイド系繊維用柔軟剤の製造方法は、天然動植物油脂またはその不飽和結合に水素を反応させた硬化油または水添動植物油脂から分離した未精製脂肪酸、またはその未精製脂肪酸を精製し炭素数分布の範囲を限定した精製脂肪酸、及び、メチル、エチル等の低級アルキルエステルとしたものを請求項１記載のアミン類と反応させ、高い温度及び減圧の条件下で生成する水または低級アルコールを反応系外に除去してアマイド反応を進行させて得られる反応生成物に無機酸もしくは有機酸を加えて中和した中和物、又は、該アマイド化反応生成物にハロゲン化低級アルキルもしくは低級ジアルキル硫酸等で４級化反応して得られる４級化物を繊維用柔軟仕上げ剤組成物の主成分としていた。
【０００３】
【発明が解決しようとする課題】
本発明は、各種繊維製品に対して優れた柔軟性と好ましい触感と吸水吸汗性を付与することのできる柔軟剤を提供すると共に、天然動植物油脂から脂肪酸を分離する際に使用される工業化学薬品の影響を可能な限り受けていない、又、天然動植物油脂から脂肪酸を分離する際に使用されるエネルギーの低減とアマイド化反応時のエネルギーの低減を計れる製造方法を提供することを目的としてなされたものである。
更に本発明は、反応時に副生するグリセリン及び未反応物を除去しないことにより、それらが各種繊維製品に対して付与する好ましい触感と吸水吸汗性を特徴とし、その特徴を最大限に発揮させるために、実質的にイミダゾリンの生成を２０重量％以下に抑えた反応条件で反応させることで繊維用柔軟仕上げ剤として優れたものを提供することを目的としてなされたものである。
【０００４】
【課題を解決するための手段】
そこで本発明者らは上記目的を解決せんと鋭意研究した結果、天然動植物油脂またはそれらの硬化油に対して、下記化学式（１）のアミン類をある条件下で直接反応させることにより、従来の技術では生成する水または低級アルコールを反応系外に除去する必要のないことによるエネルギーの低減と、天然動植物油脂から脂肪酸を分離する際に使用される工業化学薬品の影響を可能な限り受けていない、更に、天然動植物油脂とアマイド化反応により生成したグリセリン及び未反応物を含むことにより各種繊維製品に対して優れた柔軟性と好ましい触感と吸水吸汗性を付与することのできる柔軟剤とその製造方法を完成するに至った。
更に本発明では、化学式（２）のアミンには各種繊維製品に対して優れた柔軟性と好ましい触感に加えて帯電防止性を付与する効果を確認し、繊維用柔軟剤が使用される目的により、化学式（１）のアミン類と混合使用または単独使用で目的が達成できることを確認して、柔軟剤とその製造方法を完成するに至った。
【０００５】
すなわち本発明は、天然動植物油脂またはそれらの硬化油（成分ａ）に対して、化学式（１）及び／又は（２）で示されるアミン類（成分ｂ）を、実質的にイミダゾリンの生成を２０重量％以下に抑えた反応条件で反応させた後、アマイド反応生成物を無機酸もしくは有機酸で中和した中和物、又は、該アマイド化反応生成物をハロゲン化低級アルキルもしくは低級ジアルキル硫酸等で４級化反応させて得られる４級化物を５０重量％以上含み、かつ未反応物及び副生するグリセリンを含有することを特徴とする柔軟仕上げ剤組成物である。
ＮＨ₂ＣＨ₂ＣＨ₂ＮＨＣＨ₂ＣＨ₂ＸＨ（１）
〔Ｘは、ＮＨ，ＯまたはＮ（ＣＨ₂ＣＨ₂）_nＮＨのいずれか、但しｎ＝１以上の整数）
ＮＨ₂ＣＨ₂ＣＨ₂ＣＨ₂ＮＲ₁Ｒ₂ （２）
（Ｒ₁、Ｒ₂は炭素数１〜３の低級アルキル基で同一であっても異なってもよい）
【０００６】
本発明に使用する成分ａの天然動植物油脂またはそれらの硬化油には、牛脂、豚脂、魚油、大豆油、菜種油、ひまし油、オリーブ油、ゴマ油、サフラワー油、トウモロコシ油、パーム油、パーム核油、ヤシ油等の天然動植物油脂またはその硬化油及び水添動植物油脂が挙げられ、単一油脂でもまた２種類以上の油脂を混合使用してもよい。
【０００７】
更に、成分ｂのアミン類には上記化学式（１）、（２）で示されるアミン類を単一でもまた２種類以上混合使用してもよい。
【０００８】
本発明の製造において、成分ａと成分ｂとの反応はアマイド化反応であり、これらのモル比率は任意に選べるが、良好な触感を得るにはモル比が（成分ａ）／（成分ｂ）＝１／３〜２／３であるのが好ましい。反応は、空気雰囲気下で行っても良いが、窒素等不活性ガス雰囲気下で行うのが好ましく、１００〜２００℃、特に１３０〜１７０℃の温度にて行うのが好ましい。温度が低いと反応が実質上進行せず、高いと着色が激しく副反応が生じる。反応時間は反応温度等によって異なるが通常２〜３時間が好ましく、これらの反応温度、反応時間を選択することにより、イミダゾリンの生成を２０重量％以下に抑えることができる。
また本反応にはアルカリ性物質又は酸性物質を共存させても良い。
【０００９】
この反応での反応生成物を無機酸もしくは有機酸で中和するか、あるいは４級化剤で４級化することにより、柔軟仕上げ剤の主成分として用いることができる。
中和に用いる酸としては、塩酸、リン酸、硫酸、硝酸等の無機酸や、酢酸、乳酸、グリコール酸、クエン酸、マレイン酸等の炭素数６以下の有機酸が挙げられるが、好ましくは塩酸、リン酸、グリコール酸である。また４級化剤としては、塩化メチル、臭化メチル、塩化ベンジル、ジメチル硫酸、ジエチル硫酸、エピクロロヒドリン等が挙げられ、好ましくは塩化メチル、塩化ベンジル、ジメチル硫酸である。
【００１０】
【発明の効果】
本発明は、各種繊維製品に対して優れた柔軟性と好ましい触感を付与することのできる柔軟剤を提供するとともに、従来の脂肪酸やその低級アルキルエステルの代わりとして、未精製の天然動植物油脂（又はその水添動植物油脂）を用いることができるため、天然動植物油脂から脂肪酸を分離する際に使用される工業化学薬品の影響を可能な限りなくすことができ、又、天然動植物油脂から脂肪酸を分離する際に使用されるエネルギーの低減とアマイド反応時のエネルギーの低減を計ることができる。
更に、天然動植物油脂とアマイド化反応により生成したグリセリン及び未反応物を含むこと及びイミダゾリンの生成を２０重量％以下に抑えることにより各種繊維製品に対して優れた柔軟性と好ましい触感と吸水吸汗性を付与することができる。
また、アマイド化反応に使用するアミン類に柔軟性や好ましい触感とともに帯電防止性が付与できる。
【００１１】
【実施例】
以下、本発明の実施例を示し、本発明をさらに詳細に説明するが、本発明はこれらの実施例に限定されるものではない。また成分ａと成分ｂのアマイド反応、中和または４級化反応の反応例も以下に示す。
【００１２】
実施例１
温度計、還流冷却機及び攪拌機を備えた容量１リットルの反応容器に牛脂５７４ｇ、ジエチレントリアミン１０３ｇを仕込んだ。攪拌しながら昇温し、１３０〜１７０℃で２時間反応を行った後、８０〜９０℃で３７％塩酸１００ｇを加え、さらに２時間反応を行い、黄色の反応生成物を得た。
実施例２，３
表１に示す成分ａと酸に変更する以外、実施例１と同様にして反応生成物を得た。
【００１３】
実施例４
温度計、還流冷却機及び攪拌機を備えた容量１リットルの反応容器に牛脂５７４ｇ、ジエチレントリアミン１０３ｇを仕込んだ。攪拌しながら昇温し、１３０〜１７０℃で２時間反応を行った後１００〜１２０℃で塩化ベンジル１２６．４ｇを加え、さらに２時間反応を行い、黄褐色の反応生成物を得た。
実施例５，６
表１に示す成分ａと４級化剤に変更する以外、実施例４と同様にして反応生成物を得た。
【００１４】
実施例７
温度計、還流冷却機及び攪拌機を備えた容量１リットルの反応容器に牛脂硬化油４５９．２ｇ及びアミノエチルエタノールアミン１６６．４ｇを仕込んだ。攪拌しながら昇温し、１３０〜１７０℃で２時間反応を行った後、１００〜１２０℃でジメチル硫酸２０１．６ｇを加え、さらに２時間反応を行い、黄褐色の反応生成物を得た。
実施例８
表１に示す成分ａ，ｂと酸に変更する以外、実施例１と同様にして反応生成物を得た。
実施例９，１０
表１に示す成分ａ，ｂと４級化剤に変更する以外、実施例７と同様にして反応生成物を得た。
【００１５】
【表１】

【００１６】
比較例１
温度計、還流冷却機及び攪拌機を備えた容量１リットルの反応容器にステアリン酸５６９ｇ、及びジエチレントリアミン１０３ｇを仕込んだ。攪拌しながら昇温し、１７０〜１９０℃で３時間反応を行った後、８０〜９０℃で３７％塩酸１００ｇを加え、さらに２時間反応を行い、黄色の反応生成物を得た。
比較例２
ステアリン酸を牛脂脂肪酸に変更する以外、比較例１と同様にして反応生成物を得た。
【００１７】
比較例３
温度計、還流冷却機及び攪拌機を備えた容量１リットルの反応容器にステアリン酸５６９ｇ及びジエチレントリアミン１０３ｇを仕込んだ。攪拌しながら昇温し、１７０〜１９０℃で３時間反応を行った後１００〜１２０℃で塩化メチル５０．４ｇを加え、さらに２時間反応を行い、黄褐色の反応生成物を得た。
比較例４〜１０
表２に示す脂肪酸、アミン類、４級化剤その他の成分に変更する以外、比較例３と同様にして反応生成物を得た。
【００１８】
【表２】

【００１９】
柔軟仕上げ剤組成物の作成
上にあげた合成例で挙げた製造方法を用いて表１、表２に示す処方で液体柔軟仕上げ剤組成物を調整した。得られた液体柔軟仕上げ剤組成物について、それぞれの柔軟性、吸水性及び帯電防止性を下記の方法で測定し、結果を表３に示した。
なお、表中の（数字）は重量基準％であり、いずれの場合も任意成分以外の残部を水とし、組成物中のｐＨはＨＣｌ水溶液にて３．０に調整した。（ＡＥＥＡ＝アミノエチルエタノールアミン、ＤＥＴＡ＝ジエチレントリアミン、ＤＭＡＰＡ＝ジメチルアミノプロピルアミン）
【００２０】
各例の評価は下記の方法で行った。
（１）柔軟処理方法
綿メリヤス、アクリルジャージを上記で調整した液体柔軟仕上げ剤組成物を布の重量の２％投入し、４０℃、浴比１：１５で１５分間処理した後、９０℃で６０分間乾燥後、２０℃、６５％ＲＨの高温恒湿室にて２４時間放置した。これらの布について柔軟性、吸水性の評価を行った。また帯電防止性評価用のアクリルジャージは２０℃、５５％ＲＨの高温恒湿室にて７２時間放置し、評価を行った。
（２）柔軟性の評価
柔軟性の評価は比較例１の柔軟仕上げ剤で処理した布を対照にして一対比較を行った。評価は次のように表す。
＋２：対照より柔らかく感じる
＋１：対照よりやや柔らかく感じる
０：対照と柔らかさが同等
−１：対照の方がやや柔らかく感じる
−２：対照の方が柔らかく感じる
（３）吸水性の評価
柔軟処理した綿メリヤスを金属製リングに取り付け、水道水１ｍｌを１５〜２５滴分割できるビュレットを用い、ビュレットの先端が試料片の表面から１ｃｍの高さになるようにして水滴を１滴ずつ滴下させ、水滴が吸収されるまでの時間（秒）を測定した。吸収時間が小さいほど、吸水性が良好なことを意味する（ＪＩＳ，滴下法に相当）。
（４）帯電防止性の評価
ロータリースタチックネオストメーターを用い、ドライブ電圧１０ｋＶ、ドライブ高さ１５ｍｍで柔軟処理したアクリルジャージを帯電させ、電圧除去後の半減期（秒）を測定した。半減期が短いほど、帯電防止性が良好なことを意味する。
【００２１】
評価の結果を表３に示す。表３より、本発明の柔軟仕上げ剤組成物は、優れた柔軟性を付与することができ、吸水性および帯電防止性を示すことが判る。
【００２２】
【表３】

[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a softening agent useful for natural fibers and synthetic fibers, and a method for producing the same.
[0002]
[Prior art]
A typical method for producing a softening agent for fatty acid amide fibers is to purify unpurified fatty acids separated from natural animal or vegetable oils or fats or hydrogenated animal or vegetable oils or hydrogenated animal or vegetable oils that have been reacted with their unsaturated bonds. A refined fatty acid with a limited carbon number distribution and a lower alkyl ester such as methyl and ethyl are reacted with the amines according to claim 1 to produce water or lower water produced under high temperature and reduced pressure conditions. A neutralized product obtained by adding an inorganic acid or an organic acid to the reaction product obtained by removing the alcohol from the reaction system and allowing the amide reaction to proceed, or a lower alkyl halide or amideized reaction product. A quaternized product obtained by a quaternization reaction with a lower dialkyl sulfuric acid or the like was the main component of the fabric softener composition.
[0003]
[Problems to be solved by the invention]
The present invention provides a softener capable of imparting excellent flexibility, favorable tactile sensation and water absorption and sweat absorption to various textile products, and industrial chemicals used for separating fatty acids from natural animal and vegetable oils and fats It was made for the purpose of providing a production method that can reduce the energy used when separating fatty acids from natural animal and plant oils and fats and the energy during the amidation reaction. Is.
Furthermore, the present invention is characterized by preferable tactile sensation and water absorption that are imparted to various fiber products by removing glycerin and unreacted substances by-produced during the reaction, and to maximize the characteristics. Furthermore, the present invention was made for the purpose of providing an excellent fiber softener by reacting under reaction conditions in which the production of imidazoline is substantially suppressed to 20% by weight or less.
[0004]
[Means for Solving the Problems]
Therefore, as a result of diligent research to solve the above-mentioned object, the present inventors have made a conventional reaction by directly reacting an amine of the following chemical formula (1) with natural animal or vegetable oils or their hardened oil under certain conditions. The technology is not affected as much as possible by the reduction of energy by eliminating the need to remove generated water or lower alcohol out of the reaction system and the industrial chemicals used to separate fatty acids from natural animal and plant oils and fats. Furthermore, a softener capable of imparting excellent flexibility, preferable tactile sensation and water absorption and sweat absorbency to various fiber products by including glycerin generated by amide reaction and natural animal and vegetable oils and fats, and its production It came to complete the method.
Furthermore, in the present invention, the effect of imparting antistatic properties to the amine of the chemical formula (2) in addition to excellent flexibility and favorable tactile sensation to various fiber products has been confirmed. As a result, it was confirmed that the object could be achieved by mixing or using the amine of the chemical formula (1) alone, or the softener and its production method were completed.
[0005]
That is, the present invention provides the production of imidazoline by substantially adding amines (component b) represented by the chemical formula (1) and / or (2) to natural animal and vegetable oils and fats or their hardened oil (component a). After reacting under reaction conditions suppressed to not more than wt%, the amide reaction product is neutralized with an inorganic or organic acid, or the amide reaction product is halogenated lower alkyl or lower dialkyl sulfuric acid, etc. A softener composition comprising 50% by weight or more of a quaternized product obtained by the quaternization reaction in step 1, and containing unreacted material and by-product glycerin.
NH ₂ CH ₂ CH ₂ NHCH ₂ CH ₂ XH (1)
[X is either NH, O or N (CH ₂ CH ₂ ) _n NH, where n is an integer of 1 or more)
NH ₂ CH ₂ CH ₂ CH ₂ NR ₁ R ₂ (2)
(R ₁ and R ₂ may be the same or different in the lower alkyl group having 1 to 3 carbon atoms)
[0006]
The natural animal and vegetable oils and fats of component a used in the present invention include beef tallow, lard, fish oil, soybean oil, rapeseed oil, castor oil, olive oil, sesame oil, safflower oil, corn oil, palm oil, and palm kernel oil. And natural animal and vegetable oils and fats such as coconut oil, or hydrogenated animal and vegetable oils thereof, and a single oil or two or more kinds of oils and fats may be used in combination.
[0007]
Furthermore, the amines represented by the chemical formulas (1) and (2) may be used singly or as a mixture of two or more of the amines of component b.
[0008]
In the production of the present invention, the reaction between the component a and the component b is an amide reaction, and the molar ratio thereof can be arbitrarily selected, but the molar ratio is (component a) / (component b) in order to obtain a good feel. = 1/3 to 2/3 is preferable. The reaction may be performed in an air atmosphere, but is preferably performed in an inert gas atmosphere such as nitrogen, and is preferably performed at a temperature of 100 to 200 ° C, particularly 130 to 170 ° C. When the temperature is low, the reaction does not substantially proceed, and when it is high, the coloring is intense and side reactions occur. The reaction time varies depending on the reaction temperature and the like, but usually 2 to 3 hours are preferable. By selecting these reaction temperature and reaction time, the production of imidazoline can be suppressed to 20% by weight or less.
In this reaction, an alkaline substance or an acidic substance may coexist.
[0009]
By neutralizing the reaction product in this reaction with an inorganic acid or an organic acid or quaternizing with a quaternizing agent, it can be used as the main component of the softening finish.
Examples of the acid used for neutralization include inorganic acids such as hydrochloric acid, phosphoric acid, sulfuric acid, and nitric acid, and organic acids having 6 or less carbon atoms such as acetic acid, lactic acid, glycolic acid, citric acid, and maleic acid. Hydrochloric acid, phosphoric acid, glycolic acid. Examples of the quaternizing agent include methyl chloride, methyl bromide, benzyl chloride, dimethyl sulfate, diethyl sulfate, epichlorohydrin, and the like, preferably methyl chloride, benzyl chloride, and dimethyl sulfate.
[0010]
【The invention's effect】
The present invention provides a softening agent capable of imparting excellent flexibility and favorable tactile sensation to various textile products, and as an alternative to conventional fatty acids and lower alkyl esters thereof, unrefined natural animal and vegetable oils (or The hydrogenated animal and vegetable fats and oils) can be used, so that the influence of industrial chemicals used when separating fatty acids from natural animal and vegetable fats and oils can be eliminated as much as possible, and fatty acids are separated from natural animal and vegetable fats and oils. It is possible to reduce the energy used during the reaction and to reduce the energy during the amide reaction.
Furthermore, by including natural animal and vegetable oils and fats, glycerin and unreacted products produced by an amide reaction, and suppressing the production of imidazoline to 20% by weight or less, excellent flexibility and favorable tactile sensation and water absorption and sweat absorption for various textile products Can be granted.
Moreover, the antistatic property can be provided to the amines used in the amidation reaction as well as flexibility and preferable tactile sensation.
[0011]
【Example】
EXAMPLES Hereinafter, examples of the present invention will be shown and the present invention will be described in more detail. However, the present invention is not limited to these examples. Examples of amide reaction, neutralization or quaternization reaction of component a and component b are also shown below.
[0012]
Example 1
A reaction vessel having a capacity of 1 liter equipped with a thermometer, a reflux condenser and a stirrer was charged with 574 g of beef tallow and 103 g of diethylenetriamine. The mixture was heated with stirring and reacted at 130 to 170 ° C. for 2 hours, and then added with 100 g of 37% hydrochloric acid at 80 to 90 ° C. and further reacted for 2 hours to obtain a yellow reaction product.
Examples 2 and 3
A reaction product was obtained in the same manner as in Example 1 except for changing to component a and acid shown in Table 1.
[0013]
Example 4
A reaction vessel having a capacity of 1 liter equipped with a thermometer, a reflux condenser and a stirrer was charged with 574 g of beef tallow and 103 g of diethylenetriamine. The temperature was raised with stirring, and the reaction was carried out at 130 to 170 ° C. for 2 hours. Then, 126.4 g of benzyl chloride was added at 100 to 120 ° C., and the reaction was further carried out for 2 hours to obtain a yellowish brown reaction product.
Examples 5 and 6
A reaction product was obtained in the same manner as in Example 4 except that the component a and the quaternizing agent shown in Table 1 were used.
[0014]
Example 7
Into a reaction vessel having a capacity of 1 liter equipped with a thermometer, a reflux condenser and a stirrer was charged 459.2 g of beef tallow oil and 166.4 g of aminoethylethanolamine. The temperature was raised with stirring, and the reaction was performed at 130 to 170 ° C. for 2 hours. Then, 201.6 g of dimethyl sulfuric acid was added at 100 to 120 ° C., and the reaction was further performed for 2 hours to obtain a yellowish brown reaction product.
Example 8
A reaction product was obtained in the same manner as in Example 1 except that the components a and b and acid shown in Table 1 were used.
Examples 9 and 10
A reaction product was obtained in the same manner as in Example 7 except that the components a and b and the quaternizing agent shown in Table 1 were used.
[0015]
[Table 1]

[0016]
Comparative Example 1
569 g of stearic acid and 103 g of diethylenetriamine were charged into a 1 liter reaction vessel equipped with a thermometer, reflux condenser and stirrer. The mixture was heated with stirring and reacted at 170 to 190 ° C. for 3 hours. Then, 100 g of 37% hydrochloric acid was added at 80 to 90 ° C., and the reaction was further performed for 2 hours to obtain a yellow reaction product.
Comparative Example 2
A reaction product was obtained in the same manner as in Comparative Example 1 except that stearic acid was changed to beef tallow fatty acid.
[0017]
Comparative Example 3
569 g of stearic acid and 103 g of diethylenetriamine were charged into a 1 liter reaction vessel equipped with a thermometer, reflux condenser and stirrer. The temperature was raised while stirring, and the reaction was carried out at 170 to 190 ° C. for 3 hours, and then 50.4 g of methyl chloride was added at 100 to 120 ° C., and the reaction was further carried out for 2 hours to obtain a yellowish brown reaction product.
Comparative Examples 4-10
A reaction product was obtained in the same manner as in Comparative Example 3 except that the fatty acid, amines, quaternizing agent and other components shown in Table 2 were used.
[0018]
[Table 2]

[0019]
Liquid softener compositions were prepared according to the formulations shown in Tables 1 and 2 using the production methods described in the synthesis examples given above in the preparation of softener compositions. About the obtained liquid softening agent composition, each softness | flexibility, water absorption, and antistatic property were measured with the following method, and the result was shown in Table 3.
In addition, (number) in a table | surface is weight reference | standard%, In each case, the remainder other than an arbitrary component was made into water, and pH in a composition was adjusted to 3.0 with HCl aqueous solution. (AEEA = aminoethylethanolamine, DETA = diethylenetriamine, DMAPA = dimethylaminopropylamine)
[0020]
Each example was evaluated by the following method.
(1) Softening treatment method Liquid softening finish composition prepared by adjusting cotton knitted fabric and acrylic jersey as described above was added at 2% of the weight of the cloth, treated at 40 ° C. and bath ratio 1:15 for 15 minutes, and then at 90 ° C. After drying for 60 minutes, it was left for 24 hours in a high temperature and humidity chamber at 20 ° C. and 65% RH. These fabrics were evaluated for flexibility and water absorption. The acrylic jersey for evaluation of antistatic property was left for 72 hours in a high temperature and humidity chamber at 20 ° C. and 55% RH for evaluation.
(2) Evaluation of softness The softness was evaluated by comparing the fabric treated with the softener of Comparative Example 1 as a control. Evaluation is expressed as follows.
+2: feels softer than the control +1: feels slightly softer than the control 0: feels softer than the control -1: feels softer than the control-2: feels softer than the control (3) Evaluation of water absorption A cotton knitted fabric is attached to a metal ring and a burette that can split 15 to 25 drops of 1 ml of tap water is used. Droplets are dropped one by one so that the tip of the burette is 1 cm above the surface of the sample piece. Time (seconds) until was absorbed was measured. The smaller the absorption time, the better the water absorption (corresponding to JIS, dropping method).
(4) Evaluation of antistatic property Using a rotary static neostometer, an acrylic jersey that was softly processed at a drive voltage of 10 kV and a drive height of 15 mm was charged, and the half-life (seconds) after voltage removal was measured. A shorter half-life means better antistatic properties.
[0021]
Table 3 shows the evaluation results. From Table 3, it can be seen that the softener composition of the present invention can impart excellent flexibility and exhibits water absorption and antistatic properties.
[0022]
[Table 3]

Claims

With respect to natural animal and vegetable fats and oils or hardened oils thereof (component a), amines (component b) represented by the chemical formula (1) and / or (2) are substantially suppressed to produce imidazoline to 20% by weight or less. The amide reaction product is neutralized with an inorganic acid or an organic acid, or the amide reaction product is quaternized with a halogenated lower alkyl or lower dialkyl sulfuric acid, etc. A softening agent composition comprising 50% by weight or more of a quaternized product obtained by adding the unreacted product and by-product glycerin.
NH ₂ CH ₂ CH ₂ NHCH ₂ CH ₂ XH (1)
[X is either NH, O or N (CH ₂ CH ₂ ) _n NH, where n is an integer of 1 or more)
NH ₂ CH ₂ CH ₂ CH ₂ NR ₁ R ₂ (2)
(R ₁ and R ₂ may be the same or different in the lower alkyl group having 1 to 3 carbon atoms)

The softener according to claim 1, wherein the molar ratio of component a to component b is component a / component b = 1/3 to 2/3.