JPH1181137A - Softener for textile fiber - Google Patents
Softener for textile fiberInfo
- Publication number
- JPH1181137A JPH1181137A JP9257524A JP25752497A JPH1181137A JP H1181137 A JPH1181137 A JP H1181137A JP 9257524 A JP9257524 A JP 9257524A JP 25752497 A JP25752497 A JP 25752497A JP H1181137 A JPH1181137 A JP H1181137A
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- Prior art keywords
- reaction
- component
- product
- oil
- softener
- Prior art date
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Abstract
Description
【０００１】[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。TECHNICAL FIELD The present invention relates to a softening agent useful for natural fibers and synthetic fibers and a method for producing the same.
【０００２】[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。2. Description of the Related Art A typical method for producing a softening agent for fatty acid amide fiber is a crude fatty acid separated from a hardened oil or a hydrogenated vegetable oil or fat obtained by reacting a natural animal or vegetable fat or its unsaturated bond with hydrogen, Purified fatty acid which refines unpurified fatty acid and limits the range of carbon number distribution, and methyl,
Claim 1 wherein a lower alkyl ester such as ethyl is used.
Reacting with the amines described, removing water or lower alcohol generated under high temperature and reduced pressure conditions to the outside of the reaction system and allowing the amide reaction to proceed, adding an inorganic acid or an organic acid to the reaction product obtained. A neutralized neutralized product or a quaternized product obtained by quaternizing the amide reaction product with a halogenated lower alkyl or lower dialkyl sulfuric acid or the like was used as a main component of the fabric softener composition. .
【０００３】[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。DISCLOSURE OF THE INVENTION The present invention provides a softener capable of imparting excellent flexibility, a favorable tactile sensation and water-absorbing and sweat-absorbing properties to various textile products, and separates fatty acids from natural animal and vegetable fats and oils. Production method which is not affected as much as possible by the industrial chemicals used in the production, and which can reduce the energy used in separating fatty acids from natural animal and vegetable fats and oils and the energy in the amide-forming reaction The purpose of this is to provide. Furthermore, the present invention is characterized by not removing glycerin and unreacted substances by-produced at the time of the reaction, so that they are characterized by a preferable tactile sensation and water-absorbing and sweat-absorbing properties imparted to various fiber products, and to maximize the characteristics. Further, the present invention is intended to provide an excellent fabric softening agent by reacting under reaction conditions in which the production of imidazoline is substantially suppressed to 20% by weight or less.
【０００４】[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。Means for Solving the Problems The present inventors have made intensive studies to solve the above-mentioned object, and as a result, an amine of the following chemical formula (1) was added to natural animal and vegetable fats or their hardened oils under certain conditions. In the conventional technology, it is not necessary to remove generated water or lower alcohol out of the reaction system, and it is possible to reduce energy, and to use industrial chemicals used to separate fatty acids from natural animal and vegetable fats and oils. In addition, it imparts excellent flexibility, favorable tactile sensation and water-absorbing property to various textile products by containing natural animal and vegetable fats and oils and glycerin generated by amide reaction and unreacted substances as much as possible. A softener that can be used and a method for producing the same have been completed. Further, in the present invention, the amine of the formula (2) was confirmed to have an effect of imparting an antistatic property in addition to excellent flexibility and a preferable touch to various fiber products. It has been confirmed that the objective can be achieved by using the amines represented by the chemical formula (1) in combination or alone, and the softener and the method for producing the same have been completed.
【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。 ＮＨ2 ＣＨ2 ＣＨ2 ＮＨＣＨ2 ＣＨ2 ＸＨ （１） 〔Ｘは、ＮＨ，ＯまたはＮ（ＣＨ2 ＣＨ2 ）n ＮＨのい
ずれか、但しｎ＝１以上の整数） ＮＨ2 ＣＨ2 ＣＨ2 ＣＨ2 ＮＲ1 Ｒ2 （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）[0005] That is, the present invention relates to a method of preparing an amine (component b) represented by the chemical formulas (1) and / or (2) with a natural animal or vegetable fat or a hardened oil thereof (component a) to substantially convert imidazoline to After reacting under reaction conditions in which the production is suppressed to 20% by weight or less, a neutralized product obtained by neutralizing the amide reaction product with an inorganic acid or an organic acid, or a halogenated lower alkyl or lower A softener composition comprising 50% by weight or more of a quaternized product obtained by a quaternizing reaction with a dialkyl sulfuric acid and the like, and an unreacted product and glycerin by-produced. 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 are lower alkyl groups having 1 to 3 carbon atoms and may be the same or different)
【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。The natural animal and vegetable oils and fats of component a used in the present invention or their hardened oils include beef tallow, lard, fish oil, soybean oil, rapeseed oil, castor oil, olive oil, sesame oil, safflower oil, corn oil, palm oil, Examples thereof include natural animal and vegetable fats and oils such as palm kernel oil and coconut oil and hydrogenated vegetable and vegetable oils and fats, and a single fat or a mixture of two or more kinds of fats and oils may be used.
【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。Further, the amines represented by the chemical formulas (1) and (2) may be used alone or as a mixture of two or more kinds as the amines of the component b.
【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。In the production of the present invention, the reaction between the component a and the component b is an amide-forming reaction, and the molar ratio of these components can be arbitrarily selected. However, in order to obtain a good touch, the molar ratio is (component a) / (component a). It is preferred that component b) = 1/3 to 2/3. The reaction may be performed in an air atmosphere, but is preferably performed in an inert gas atmosphere such as nitrogen.
C., preferably at a temperature of from 130 to 170.degree. When the temperature is low, the reaction does not substantially proceed, and when the temperature is high, the coloring is severe and a side reaction occurs. The reaction time varies depending on the reaction temperature and the like, but is usually preferably 2 to 3 hours. By selecting the reaction temperature and the 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】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。The reaction product of this reaction can be neutralized with an inorganic or organic acid or quaternized with a quaternizing agent to be used as a main component of the softening agent. Acids used for neutralization include hydrochloric acid, phosphoric acid, sulfuric acid,
Examples thereof include inorganic acids such as 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, and glycolic acid are preferred. Examples of the quaternizing agent include methyl chloride, methyl bromide, benzyl chloride, dimethyl sulfate, diethyl sulfate, epichlorohydrin and the like, and preferred are methyl chloride, benzyl chloride and dimethyl sulfate.
【００１０】[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。Industrial Applicability The present invention provides a softener capable of imparting excellent softness and a preferable tactile sensation to various fiber products, and replaces conventional fatty acids and their lower alkyl esters with unpurified ones. Since natural animal and vegetable fats and oils (or hydrogenated animal and vegetable fats and oils) can be used, the influence of industrial chemicals used for separating fatty acids from natural animal and vegetable fats and oils can be minimized. Energy used for separating fatty acids from acetic acid and energy used for amide reaction can be reduced. Furthermore, by containing glycerin and unreacted substances formed by the amido-forming reaction with natural animal and vegetable fats and oils, and by suppressing the production of imidazoline to 20% by weight or less, excellent flexibility, preferable touch and water-absorbing and sweat-absorbing properties for various fiber products. Can be provided. In addition, it is possible to impart an antistatic property to the amines used in the amide-forming reaction together with flexibility and a preferable touch.
【００１１】[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。EXAMPLES Hereinafter, the present invention will be described in more detail with reference to Examples of the present invention, but the present invention is not limited to these Examples. Further, examples of the amide reaction, neutralization or quaternization reaction of component a and component b are also shown below.
【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１０
３ｇ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。Example 1 574 g of tallow and 10 parts of diethylenetriamine were placed in a 1-liter reaction vessel equipped with a thermometer, a reflux condenser and a stirrer.
3 g were charged. Raise the temperature while stirring, 130-170
After reacting for 2 hours at 80 ° C., 100 g of 37% hydrochloric acid was added at 80 to 90 ° C., and the reaction was further conducted 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 that the component a and the acid shown in Table 1 were used.
【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１０
３ｇ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。EXAMPLE 4 574 g of beef tallow and 10 parts of diethylenetriamine were placed in a 1-liter reaction vessel equipped with a thermometer, a reflux condenser and a stirrer.
3 g were charged. Raise the temperature while stirring, 130-170
After performing the reaction at 2 ° C. for 2 hours, 126.4 g of benzyl chloride was added at 100 to 120 ° C., and the reaction was further performed for 2 hours to obtain a yellow-brown reaction product. Examples 5 and 6 Example 4 except that the component a and the quaternizing agent shown in Table 1 were changed.
A reaction product was obtained in the same manner as described above.
【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。Example 7 A 1-liter reaction vessel equipped with a thermometer, a reflux condenser and a stirrer was charged with 459.2 g of hardened tallow oil and 166.4 g of aminoethylethanolamine. The temperature was raised while stirring, and the reaction was performed at 130 to 170 ° C. for 2 hours.
At 100 to 120 ° C., 201.6 g of dimethyl sulfuric acid is added,
The reaction was further performed for 2 hours to obtain a yellow-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 the acid shown in Table 1 were changed. Examples 9 and 10 A reaction product was obtained in the same manner as in Example 7, except that the components a and b shown in Table 1 were changed to the quaternizing agent.
【００１５】[0015]
【表１】 [Table 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、１
７０〜１９０℃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。Comparative Example 1 569 g of stearic acid and 103 g of diethylenetriamine were charged into a 1-liter reactor equipped with a thermometer, a reflux condenser and a stirrer. Raise the temperature while stirring.
After reacting at 70 to 190 ° C for 3 hours, 80 to 90 ° C
Then, 100 g of 37% hydrochloric acid was added, and the mixture was further reacted 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】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、１７
０〜１９０℃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。Comparative Example 3 A 1-liter reactor equipped with a thermometer, a reflux condenser and a stirrer was charged with 569 g of stearic acid and 103 g of diethylenetriamine. The temperature was increased while stirring, and 17
After reacting at 0 to 190 ° C for 3 hours, 100 to 120 ° C
Then, 50.4 g of methyl chloride was added, and the mixture was further reacted for 2 hours to obtain a yellow-brown reaction product. Comparative Examples 4 to 10 Reaction products were obtained in the same manner as in Comparative Example 3 except that fatty acids, amines, quaternizing agents and other components shown in Table 2 were used.
【００１８】[0018]
【表２】 [Table 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）Preparation of softener composition Tables 1 and 2 were prepared using the production methods described in the above synthesis examples.
A liquid softener composition was prepared according to the formulation shown in Table 1. With respect to the obtained liquid softener composition, the flexibility, water absorption and antistatic property of each were measured by the following methods, and the results are shown in Table 3. In addition, (numerical value) in the table is% by weight, the balance other than the optional components was water in each case, and the pH in the composition was adjusted to 3.0 with an aqueous HCl solution.
(AEEA = aminoethylethanolamine, DETA
= Diethylenetriamine, DMAPA = dimethylaminopropylamine)
【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。The evaluation of each example was performed by the following method. (1) Softening treatment The liquid softening agent composition prepared above with cotton knit and acrylic jersey was charged at 2% of the weight of the cloth, treated at 40 ° C and a bath ratio of 1:15 for 15 minutes and then at 90 ° C. After drying for 60 minutes, it was left in a high temperature and humidity room at 20 ° C. and 65% RH for 24 hours. These fabrics were evaluated for flexibility and water absorption. The acrylic jersey for antistatic evaluation was 20
The sample was left for 72 hours in a high temperature and humidity room at 55 ° 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. The evaluation is expressed as follows. +2: Feels softer than control +1: Feels slightly softer than control 0: Equals softness to control -1: Feels somewhat softer to control -2: Feels softer to control (3) Evaluation of water absorption Attach a cotton knit to a metal ring and use a burette that can divide 15 ml of tap water into 15 to 25 drops. Drop the water drops one by one so that the tip of the buret is at a height of 1 cm from the surface of the sample piece. The time (sec) until was absorbed was measured. The shorter the absorption time, the better the water absorption (equivalent to JIS, dropping method). (4) Evaluation of antistatic property An acrylic jersey subjected to a flexible treatment at a drive voltage of 10 kV and a drive height of 15 mm was charged using a rotary static neostometer, and the half-life (second) after voltage removal was measured. The shorter the half-life, the better the antistatic properties.
【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。Table 3 shows the results of the evaluation. Table 3 shows that the softener composition of the present invention can impart excellent flexibility and exhibit water absorption and antistatic properties.
【００２２】[0022]
【表３】 [Table 3]
Claims (2)
（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。 ＮＨ2 ＣＨ2 ＣＨ2 ＮＨＣＨ2 ＣＨ2 ＸＨ （１） 〔Ｘは、ＮＨ，ＯまたはＮ（ＣＨ2 ＣＨ2 ）n ＮＨのい
ずれか、但しｎ＝１以上の整数） ＮＨ2 ＣＨ2 ＣＨ2 ＣＨ2 ＮＲ1 Ｒ2 （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）1. An amine (component b) represented by the chemical formula (1) and / or (2) is added to a natural animal or vegetable fat or oil or its hardened oil (component a) to substantially reduce imidazoline production. After the reaction is carried out under the reaction condition of not more than 10% by weight, a neutralized product obtained by neutralizing the amide reaction product with an inorganic acid or an organic acid, or a halogenated lower alkyl or lower dialkyl sulfate, etc. A softening agent composition comprising 50% by weight or more of a quaternized product obtained by a quaternizing reaction in the above, and containing unreacted substances and glycerin by-produced. 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 are lower alkyl groups having 1 to 3 carbon atoms and may be the same or different)
ｂ＝１／３〜２／３である請求項１記載の柔軟仕上げ
剤。2. 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.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25752497A JP3820007B2 (en) | 1997-09-05 | 1997-09-05 | Textile softener |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25752497A JP3820007B2 (en) | 1997-09-05 | 1997-09-05 | Textile softener |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH1181137A true JPH1181137A (en) | 1999-03-26 |
| JP3820007B2 JP3820007B2 (en) | 2006-09-13 |
Family
ID=17307501
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25752497A Expired - Fee Related JP3820007B2 (en) | 1997-09-05 | 1997-09-05 | Textile softener |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3820007B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003105666A (en) * | 2001-09-28 | 2003-04-09 | Shikibo Ltd | Textile softener, method of softening textile, textile product treated with the softener and textile softener spray |
| JP2016106187A (en) * | 2011-11-17 | 2016-06-16 | 日本電信電話株式会社 | Electroconductive polymer fiber |
-
1997
- 1997-09-05 JP JP25752497A patent/JP3820007B2/en not_active Expired - Fee Related
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003105666A (en) * | 2001-09-28 | 2003-04-09 | Shikibo Ltd | Textile softener, method of softening textile, textile product treated with the softener and textile softener spray |
| JP2016106187A (en) * | 2011-11-17 | 2016-06-16 | 日本電信電話株式会社 | Electroconductive polymer fiber |
| JP2017201070A (en) * | 2011-11-17 | 2017-11-09 | 日本電信電話株式会社 | Electroconductive polymer fiber |
| US10153065B2 (en) | 2011-11-17 | 2018-12-11 | Nippon Telegraph And Telephone Corporation | Conductive polymer fibers, method and device for producing conductive polymer fibers, biological electrode, device for measuring biological signals, implantable electrode, and device for measuring biological signals |
| US11862359B2 (en) | 2011-11-17 | 2024-01-02 | Nippon Telegraph And Telephone Corporation | Conductive polymer fibers, method and device for producing conductive polymer fibers, biological electrode, device for measuring biological signals, implantable electrode, and device for measuring biological signals |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3820007B2 (en) | 2006-09-13 |
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