JPH06212568A - Liquid softening agent - Google Patents
Liquid softening agentInfo
- Publication number
- JPH06212568A JPH06212568A JP473493A JP473493A JPH06212568A JP H06212568 A JPH06212568 A JP H06212568A JP 473493 A JP473493 A JP 473493A JP 473493 A JP473493 A JP 473493A JP H06212568 A JPH06212568 A JP H06212568A
- Authority
- JP
- Japan
- Prior art keywords
- softening agent
- acid
- liquid softening
- carbon atoms
- elasticity
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
(57)【要約】
【構成】 下記の一般式 (A)又は(B) で表されるアミン
の中和物又は4級化物の1種以上を必須成分とする液体
柔軟仕上剤。
【化1】
〔式中、R1, R2は炭素数1〜4のアルキル基もしくはヒ
ドロキシアルキル基、R3, R4は水酸基で置換されていて
もよい直鎖又は分岐鎖の炭素数7〜35のアルキル基又は
アルケニル基、p は1〜3の整数、m, nは0〜3の整数
を示す。〕
【効果】 各種繊維に対して、十分な柔軟性、帯電防止
性を与えるとともに、優れた弾力性を付与できる。(57) [Summary] [Structure] A liquid softening agent containing at least one neutralized or quaternized amine represented by the following general formula (A) or (B) as an essential component. [Chemical 1] [Wherein R 1 and R 2 are alkyl groups or hydroxyalkyl groups having 1 to 4 carbon atoms, and R 3 and R 4 are linear or branched alkyl groups having 7 to 35 carbon atoms which may be substituted with a hydroxyl group. A group or an alkenyl group, p is an integer of 1 to 3, m and n are integers of 0 to 3. [Effect] It is possible to impart sufficient flexibility and antistatic properties to various fibers and to impart excellent elasticity.
Description
【0001】[0001]
【産業上の利用分野】本発明は、柔軟仕上剤に関し、詳
しくは各種の繊維に対して、優れた柔軟性及び弾力性
(ふっくら感)を付与できる液体柔軟仕上剤に関するも
のである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a softening finish, and more particularly to a liquid softening finish which can impart excellent flexibility and elasticity (puffiness) to various fibers.
【0002】[0002]
【従来の技術及び発明が解決しようとする課題】現在、
家庭用柔軟仕上剤として市販されている商品は殆どがジ
(硬化牛脂アルキル)ジメチルアンモニウムクロライド
に代表されるような1分子中に1〜2個の長鎖アルキル
基を有する第4級アンモニウム塩を主成分とした組成で
ある。この理由としては第4級アンモニウム塩は少量で
各種繊維に対して良好な柔軟効果を有するからである。2. Description of the Related Art Currently,
Most of the commercially available products as household softening agents are quaternary ammonium salts having 1 to 2 long chain alkyl groups in one molecule as typified by di (hardened tallow alkyl) dimethylammonium chloride. The composition is the main component. The reason for this is that a small amount of quaternary ammonium salt has a good softening effect on various fibers.
【0003】しかしながら、上記の第4級アンモウム塩
は、木綿類に対しては著しい柔軟効果を有しているが、
アクリル系、ポリエステル系、ポリアミド系などの合成
繊維に対しては効果が十分とは言い難く、更に高濃度で
処理すると衣料の弾力性が低下し風合いが損なわれてし
まうことがある。However, the above-mentioned quaternary ammonium salt has a remarkable softening effect on cotton,
It is difficult to say that the effect is sufficient for synthetic fibers such as acrylic, polyester, and polyamide fibers, and if the treatment is performed at a higher concentration, the elasticity of the clothing may be reduced and the texture may be impaired.
【0004】また、長期保存をする場合は、特に低温で
増粘したり、ゲル状になったり、分離したりすることが
ある。Further, when it is stored for a long period of time, it may thicken, gel, or separate, especially at low temperatures.
【0005】このため柔軟成分以外の各種のポリオキシ
エチレン系の非イオン活性剤や電解質、溶剤を必要と
し、これらを配合して安定化を行っているものが多い
が、未だ効果は十分でない。Therefore, various polyoxyethylene-based nonionic activators, electrolytes, and solvents other than the soft component are required, and many of them are compounded for stabilization, but the effect is not sufficient yet.
【0006】上記の第4級アンモニウム塩を主基剤とす
る柔軟仕上剤は通常4〜20%の分散液として市販され、
使用されている。The above-mentioned softening agent having a quaternary ammonium salt as a main base is usually commercially available as a 4 to 20% dispersion liquid,
It is used.
【0007】第4級アンモニウム塩は疎水性が強いた
め、すすぎ水中に投入する際、攪拌力が弱い場合は水へ
の分散性が悪く、そのため衣料に対してムラ付きするお
それがある。市販の柔軟剤は上記の第4級アンモニウム
塩の他に様々な添加剤を配合し、水への分散性を改良し
ているが、その効果は未だ不十分である。Since the quaternary ammonium salt has a strong hydrophobicity, when it is poured into the rinse water, if the stirring power is weak, the dispersibility in water is poor, which may cause unevenness on the clothing. Commercially available softeners are mixed with various additives in addition to the above quaternary ammonium salt to improve dispersibility in water, but the effect is still insufficient.
【0008】また、従来より各種アミンを柔軟基剤とす
る液体柔軟仕上剤が知られている。例えば特開昭52−
597965号公報にはメチルジ(硬化牛脂アルキル)
アミンのような長鎖アルキルアミンを含有する繊維に柔
軟性を付与する組成物が、特開昭58−60070号公
報にはアシル化アルカノールアミン、水溶性−第4級ア
ンモニウム塩及び脂肪酸エステルを含有する繊維に平滑
性、快適な手触りを与える繊維材料仕上剤が、特開昭6
1−167083号公報には第4級アンモニウム化合
物、高級脂肪酸とヒドロキシ低級アルキルポリアミンポ
リグリコールエーテルを含有する分散性の良い柔軟剤
が、特開昭61−275474号公報にはジ(高級アル
キル)環式アミン及びブレンステッド酸を含有する織物
処理用の安定な水性分散液が、特開昭64−85368
号公報にはジ長鎖アルキルアミン−陰イオン性界面活性
剤イオン対複合体、非シリコーンロウ及び液体担含む柔
軟化組成物が、特開平2−14076号公報にはジ長鎖
アルキルアミン−多官能カルボン酸錯体を含有する柔軟
剤、帯電防止性を付与する布類コンディショニング組成
物が記載されている。Liquid softening finishes having various amines as softening bases have been conventionally known. For example, JP-A-52-1
No. 579965 discloses methyldi (hardened tallow alkyl).
A composition for imparting flexibility to a fiber containing a long-chain alkylamine such as an amine contains an acylated alkanolamine, a water-soluble-quaternary ammonium salt and a fatty acid ester in JP-A-58-60070. A finishing agent for a fiber material which imparts smoothness and a comfortable feel to the formed fiber is disclosed in Japanese Patent Application Laid-Open No. 6-58242.
No. 1-167083 discloses a softening agent containing a quaternary ammonium compound, a higher fatty acid and a hydroxy lower alkyl polyamine polyglycol ether with good dispersibility, and JP-A No. 61-275474 discloses a di (higher alkyl) ring. A stable aqueous dispersion for treating textiles containing the formula amine and Bronsted acid is disclosed in JP-A-64-85368.
JP-A-2-14076 discloses a softening composition containing a dilong-chain alkylamine-anionic surfactant ion pair complex, a non-silicone wax and a liquid. A softening agent containing a functional carboxylic acid complex and a fabric conditioning composition imparting antistatic properties are described.
【0009】更に、特開昭52−5394号公報にはモ
ノ又はジ長鎖アルキルアルキレンジアミン静電気抑制剤
及び第4級アンモニウム系柔軟剤を含有する布類状態調
節組成物が記載されている。Further, Japanese Unexamined Patent Publication No. 52-5394 describes a fabric condition-controlling composition containing a mono- or di-long-chain alkylalkylenediamine antistatic agent and a quaternary ammonium softening agent.
【0010】これらアミンを含有する柔軟剤は分散性、
保存安定性について、第4級アンモニウム塩を含有する
柔軟剤に比べ比較的良好であるものの、柔軟性能につい
ては未だ充分でない。Softeners containing these amines are dispersible,
The storage stability is relatively good as compared with the softener containing a quaternary ammonium salt, but the softening performance is still insufficient.
【0011】[0011]
【課題を解決するための手段】本発明者らは、アミンを
含有する柔軟剤について鋭意研究した結果、特殊な(ジ
長鎖型)アミン化合物の中和物又は4級化物が柔軟性に
優れ、しかも衣類に弾力性(ふっくら感)を付与できる
ことを見出し、本発明を完成するに至った。Means for Solving the Problems As a result of intensive studies on the softener containing an amine, the present inventors have found that a neutralized product or a quaternized product of a special (dilong chain type) amine compound has excellent flexibility. Moreover, they have found that it is possible to impart elasticity (puffiness) to clothes, and have completed the present invention.
【0012】すなわち本発明は、下記の一般式 (A)又は
(B) で表される化合物の中和物又は4級化物の1種以上
を必須成分として含有することを特徴とする液体柔軟仕
上剤を提供するものである。That is, the present invention provides the following general formula (A) or
The present invention provides a liquid softening finish characterized by containing one or more neutralized or quaternized compounds of the compound represented by (B) as an essential component.
【0013】[0013]
【化2】 [Chemical 2]
【0014】〔式中、 R1, R2:炭素数1〜4のアルキル基もしくはヒドロキシ
アルキル基 R3, R4:水酸基で置換されていてもよい直鎖又は分岐鎖
の炭素数7〜35のアルキル基又はアルケニル基 p :1〜3の整数 m, n:0〜3の整数 を示す。〕。[Wherein R 1 and R 2 are C 1 to C 4 alkyl groups or hydroxyalkyl groups R 3 and R 4 are linear or branched C 7 to 35 carbon atoms that may be substituted with a hydroxyl group. Is an alkyl group or an alkenyl group of p: an integer m of 1-3, and an integer of n: 0-3. ].
【0015】本発明に係る上記一般式 (A)又は(B) で表
されるアミンの代表例としては、N,N −ジメチル−2,3
−ジアミノ−プロピルアミンのアシル化物等が挙げられ
る。かかるアシル化物の合成方法についてはここでは詳
細に述べないが、N,N −ジメチルアミンにエピクロルヒ
ドリンを反応させ、さらに三臭化リンによってヒドロキ
シル基をブロム化する。さらにそれを水酸化アンモニウ
ムでアミノ化する。最後にそれを脂肪酸又はそのエステ
ル化合物でアシル化することにより目的物を容易に得ら
れる。この反応に用いられる脂肪酸又はそのエステル化
合物はヤシ油、パーム油、牛脂、豚脂、ナタネ油、魚油
等の天然油脂由来のものが一般的であるが、オクタデカ
ン酸又はヒドロキシオクタデカン酸等の化学的に合成し
た化合物でも良い。また、一般式(A) 又は(B) におい
て、R1とR2、或いはR3とR4はそれぞれ同一でも異なって
いてもよい。Typical examples of the amine represented by the above general formula (A) or (B) according to the present invention include N, N-dimethyl-2,3
Examples include acylated products of diamino-propylamine. Although a method for synthesizing such an acyl compound will not be described in detail here, N, N-dimethylamine is reacted with epichlorohydrin, and the hydroxyl group is brominated with phosphorus tribromide. Further it is aminated with ammonium hydroxide. Finally, the desired product can be easily obtained by acylating it with a fatty acid or its ester compound. Fatty acids or ester compounds thereof used in this reaction are generally derived from natural oils and fats such as coconut oil, palm oil, beef tallow, lard, rapeseed oil and fish oil. The compound synthesized in 1. may be used. Further, in the general formula (A) or (B), R 1 and R 2 , or R 3 and R 4 may be the same or different.
【0016】一般式(A) 又は(B) で表されるアミンか
ら、本発明の中和物を得るための酸としては塩酸、硫
酸、硝酸、リン酸等の無機酸や、酢酸、乳酸、グリコー
ル酸、クエン酸、マレイン酸、フマール酸、トルエンス
ルホン酸等の有機酸等が挙げられる。また、一般式(A)
又は(B) で表されるアミンの4級化物を得るための4級
化剤としてはメチルクロライド等のハロゲン化アルキル
の他にジメチル硫酸等のアルキル硫酸化合物などが挙げ
られる。As the acid for obtaining the neutralized product of the present invention from the amine represented by the general formula (A) or (B), inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid and phosphoric acid, acetic acid, lactic acid, Examples thereof include organic acids such as glycolic acid, citric acid, maleic acid, fumaric acid, and toluenesulfonic acid. Also, the general formula (A)
Alternatively, examples of the quaternizing agent for obtaining the quaternary compound of the amine represented by (B) include alkyl halide compounds such as methyl chloride, and alkyl sulfate compounds such as dimethyl sulfate.
【0017】本発明の液体柔軟仕上剤は、例えばアミン
化合物の溶融物又は濃厚液を攪拌又は剪断混合下に、中
和剤を含む水溶液中にゆっくり添加することにより得ら
れるが、この方法に限定されるものではなく、中和物を
予め製造する或いは中和物を後添加する等の方法によっ
て得ることもできる。The liquid softening agent of the present invention can be obtained, for example, by slowly adding a melt or concentrate of an amine compound to an aqueous solution containing a neutralizing agent with stirring or shear mixing, but the method is not limited to this method. However, it can also be obtained by a method in which the neutralized product is produced in advance or the neutralized product is added later.
【0018】本発明において、一般式(A) 又は(B) で表
されるアミンの酸中和物又は4級化物は単独でも2種以
上を混合して用いてもよく、その配合量は、組成物中に
総量で4〜40重量%、好ましくは6〜30重量%、特に好
ましくは10〜30重量%配合される。In the present invention, the acid neutralized product or quaternized product of the amine represented by the general formula (A) or (B) may be used alone or in combination of two or more, and the blending amount thereof is The composition is incorporated in a total amount of 4 to 40% by weight, preferably 6 to 30% by weight, particularly preferably 10 to 30% by weight.
【0019】本発明の液体柔軟仕上剤に、ジメチルポリ
シロキサン、部分的にアミノ基又はポリオキシアルキレ
ン基で変性されたジメチルポリシロキサン等のシリコー
ン化合物、特に好ましくは部分的にポリオキシアルキレ
ン基で変性されたジメチルポリシロキサンを配合するこ
とにより吸水性を損なうことなく、柔軟処理された衣料
の肌触りを改良できる。これらのシリコーン化合物は、
柔軟仕上剤全体に対して 0.3〜5重量%配合されるのが
好ましい。The liquid softening agent of the present invention contains a silicone compound such as dimethylpolysiloxane and dimethylpolysiloxane partially modified with an amino group or a polyoxyalkylene group, particularly preferably partially modified with a polyoxyalkylene group. By blending the dimethylpolysiloxane described above, it is possible to improve the feel of the softly treated clothing without impairing the water absorption. These silicone compounds are
It is preferable to add 0.3 to 5% by weight based on the entire softening agent.
【0020】本発明の液体柔軟仕上剤には更に粘度の調
整のために塩化ナトリウム、塩化カルシウム、塩化マグ
ネシウム等の無機電解質を0.05〜0.4 重量%添加するの
が望ましい。It is desirable to add 0.05 to 0.4% by weight of an inorganic electrolyte such as sodium chloride, calcium chloride or magnesium chloride to the liquid softening finish of the present invention for adjusting the viscosity.
【0021】本発明の液体柔軟仕上剤は長期保存に対し
て安定性は高いが、更に苛酷な保存条件下での安定化の
ためにポリオキシエチレン(5〜50モル)アルキル又は
アルケニル(C12〜C24)エーテルやポリオキシプロピレン
(5〜50モル)アルキル又はアルケニル(C12〜C24)エー
テル等のノニオン界面活性剤、エタノール、プロピレン
グリコール、エチレングリコールやグリセリンのような
溶剤又は尿素などを配合することができる。また、柔軟
基剤として既知のエステル、非イオン或いはカチオン化
合物、長鎖アルコール、長鎖アミン、長鎖脂肪酸等を併
用しても良い。The liquid softening agent of the present invention has high stability for long-term storage, but for further stabilization under severe storage conditions, polyoxyethylene (5 to 50 mol) alkyl or alkenyl (C 12 ~ C 24 ) ether or polyoxypropylene (5 to 50 mol) alkyl or alkenyl (C 12 to C 24 ) nonionic surfactant such as ether, solvent such as ethanol, propylene glycol, ethylene glycol or glycerin, or urea It can be blended. Further, a known ester, a nonionic or cationic compound, a long chain alcohol, a long chain amine, a long chain fatty acid or the like may be used in combination as a soft base.
【0022】また、製品の外観のために顔料又は染料
を、仕上がりの白さのために蛍光増白剤を、そして使用
時及び仕上がり後の趣向を良くするために香料を配合す
ることもできる。なお、本発明の液体柔軟仕上剤の残部
は水と任意成分である。It is also possible to add pigments or dyes for the appearance of the product, fluorescent whitening agents for the whiteness of the finished product, and fragrances to improve the taste when used and after the finished product. The balance of the liquid softening agent of the present invention is water and optional components.
【0023】[0023]
【発明の効果】本発明の液体柔軟仕上剤は、従来広く用
いられている硬化牛脂アルキルジメチルアンモニウムク
ロライドに比較すると、各種繊維に対する柔軟効果及び
帯電防止効果は同等以上であり、しかも驚くべきことに
弾力性のある柔らかさが得られることが分かった。EFFECTS OF THE INVENTION The liquid softening agent of the present invention has the same or better softening effect and antistatic effect on various fibers as compared with the conventionally widely used hardened tallow alkyldimethylammonium chloride, and surprisingly. It was found that elastic softness was obtained.
【0024】[0024]
【実施例】次に本発明を実施例をもって詳述するが、本
発明はこれらの実施例に限定されるものではない。実施
例及び比較例で用いた化合物を表1に示す。EXAMPLES The present invention will now be described in detail with reference to examples, but the present invention is not limited to these examples. The compounds used in Examples and Comparative Examples are shown in Table 1.
【0025】[0025]
【表1】 [Table 1]
【0026】実施例1〜9及び比較例1 1)弾力性の評価 (1) 処理方法 市販の木綿タオル2kg、アクリルジャージ1kgを 3.5°
DH硬水にて市販洗剤アタック(花王株式会社製、登録商
標)にて5回繰り返し洗濯(30リットル洗濯機)をし、
各繊維についていた繊維処理剤を除去した後、表2に示
す配合量で、表1に示す化合物の中和物又は4級化物を
水に分散させた柔軟仕上剤配合物 1.5gを投入し、25
℃、1分間攪拌下で処理した。 (2) 評価方法 上記方法で処理した布を室内で風乾後、25℃、65%RHの
恒温湿室にて24時間放置した。これらの布について弾力
性の評価を行った。Examples 1 to 9 and Comparative Example 1 1) Evaluation of elasticity (1) Treatment method 2 kg of a commercially available cotton towel and 1 kg of an acrylic jersey were set at 3.5 °.
Repeatedly wash 5 times (30 liter washing machine) with a commercial detergent attack (Kao Corporation, registered trademark) with DH hard water,
After removing the fiber treating agent attached to each fiber, 1.5 g of a softening agent composition prepared by dispersing a neutralized product or a quaternary compound of the compound shown in Table 1 in water was added in an amount shown in Table 2. twenty five
The mixture was treated under stirring at 1 ° C for 1 minute. (2) Evaluation method The cloth treated by the above method was air-dried indoors and then left in a constant temperature and humidity room at 25 ° C and 65% RH for 24 hours. The elasticity of these cloths was evaluated.
【0027】弾力性の評価は、ジ水素添加牛脂アルキル
ジメチルアンモニウムクロライド15重量%からなる柔軟
仕上剤10cc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;対照より弾力性が高い +1;対照より弾力性がやや高い 0;対照と同じ −1;対照より弾力性がやや低い −2;対照より弾力性が低い 表2に示すように、本発明の化合物を使用することによ
り、弾力性を満足する効果が得られる。For the evaluation of elasticity, a pair of comparisons were carried out by using a cloth treated with 10 cc of a softening agent containing 15% by weight of dihydrogenated tallow alkyldimethylammonium chloride as a control. The evaluation is expressed as follows. +2; higher elasticity than the control +1; slightly higher elasticity than the control 0; same as the control -1; slightly lower elasticity than the control -2: lower elasticity than the control As shown in Table 2, the present invention. By using the compound (1), the effect of satisfying elasticity can be obtained.
【0028】[0028]
【表2】 [Table 2]
【0029】実施例10〜12及び比較例2 表3に示す配合の組成物について弾力性を評価するた
め、木綿タオルの積み上げ高さを測定した。 <弾力性の評価>実施例1〜9及び比較例1の処理方法
と同様に処理した木綿タオルを8つ折りにして3枚重ね
て積み上げ、5g/cm2 の圧力で5 間加圧した後、圧
力を取り除き、タオルの高さを測定した。タオルの高さ
が高い程、弾力性は良好である。Examples 10 to 12 and Comparative Example 2 In order to evaluate the elasticity of the compositions having the formulations shown in Table 3, the pile height of cotton towels was measured. <Evaluation of elasticity> After folding the cotton towels treated in the same manner as in Examples 1 to 9 and Comparative Example 1 into eight, stacking three sheets and stacking them, a pressure of 5 g / cm 2 was applied for 5 minutes, The pressure was removed and the height of the towel was measured. The higher the towel height, the better the elasticity.
【0030】[0030]
【表3】 [Table 3]
Claims (1)
合物の中和物又は4級化物の1種以上を必須成分として
含有することを特徴とする液体柔軟仕上剤。 【化1】 〔式中、 R1, R2:炭素数1〜4のアルキル基もしくはヒドロキシ
アルキル基 R3, R4:水酸基で置換されていてもよい直鎖又は分岐鎖
の炭素数7〜35のアルキル基又はアルケニル基 p :1〜3の整数 m, n:0〜3の整数 を示す。〕1. A liquid softening agent containing one or more neutralized or quaternized compounds of compounds represented by the following general formula (A) or (B) as an essential component. [Chemical 1] [In the formula, R 1 and R 2 are alkyl groups having 1 to 4 carbon atoms or hydroxyalkyl groups R 3 and R 4 are linear or branched alkyl groups having 7 to 35 carbon atoms which may be substituted with a hydroxyl group. Or an alkenyl group p: an integer m of 1 to 3 and n: an integer of 0 to 3. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP00473493A JP3164679B2 (en) | 1993-01-14 | 1993-01-14 | Liquid soft finish |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP00473493A JP3164679B2 (en) | 1993-01-14 | 1993-01-14 | Liquid soft finish |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06212568A true JPH06212568A (en) | 1994-08-02 |
| JP3164679B2 JP3164679B2 (en) | 2001-05-08 |
Family
ID=11592139
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP00473493A Expired - Fee Related JP3164679B2 (en) | 1993-01-14 | 1993-01-14 | Liquid soft finish |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3164679B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021010161A1 (en) * | 2019-07-12 | 2021-01-21 | 松本油脂製薬株式会社 | Antistatic treatment agent for fibers and use thereof |
-
1993
- 1993-01-14 JP JP00473493A patent/JP3164679B2/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021010161A1 (en) * | 2019-07-12 | 2021-01-21 | 松本油脂製薬株式会社 | Antistatic treatment agent for fibers and use thereof |
| JPWO2021010161A1 (en) * | 2019-07-12 | 2021-09-13 | 松本油脂製薬株式会社 | Antistatic processed chemicals for fibers and their use |
| CN114144554A (en) * | 2019-07-12 | 2022-03-04 | 松本油脂制药株式会社 | Antistatic agent for fiber and use thereof |
| CN114144554B (en) * | 2019-07-12 | 2023-08-25 | 松本油脂制药株式会社 | Antistatic Processing Agent for Fiber and Its Utilization |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3164679B2 (en) | 2001-05-08 |
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