JPH0718569A - Softening agent composition - Google Patents
Softening agent compositionInfo
- Publication number
- JPH0718569A JPH0718569A JP18704893A JP18704893A JPH0718569A JP H0718569 A JPH0718569 A JP H0718569A JP 18704893 A JP18704893 A JP 18704893A JP 18704893 A JP18704893 A JP 18704893A JP H0718569 A JPH0718569 A JP H0718569A
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- Prior art keywords
- acid
- softening agent
- amine
- agent composition
- chain
- Prior art date
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Abstract
Description
【0001】[0001]
【産業上の利用分野】本発明は、繊維や衣料に柔軟性を
付与するための柔軟剤組成物に関し、特に、洗濯による
アニオン界面活性剤の影響を受けにくく柔軟性に優れた
柔軟剤組成物に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a softener composition for imparting flexibility to fibers and clothes, and particularly to a softener composition which is hardly affected by an anionic surfactant due to washing and has excellent flexibility. Regarding
【0002】[0002]
【従来の技術】従来、家庭用柔軟仕上剤として市販され
ている殆どの商品は、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第4級アンモニウ
ム塩を主成分として用いているが、近年普及してきた全
自動洗濯機での使用には問題がある。全自動洗濯機は浴
比が小さくすすぎ回数が少ない為に、柔軟処理時の浴中
に存在するアニオン界面活性剤量が増加し、カチオン性
が強い第4級アンモニウム塩とアニオン−カチオン複合
体を形成し、柔軟効果が低下することが判つて来た。一
方、カチオン性が多少弱いアミンを柔軟剤基剤として用
いる手法も知られている。たとえば、特開昭52−05
9796号公報には、メチルジ(硬化牛脂アルキル)ア
ミンを用いる組成が開示されているが、この組成物でも
本質的に柔軟効果が低く未だ充分ではなかつた。そこ
で、全自動洗濯機を使用した柔軟処理において特に、柔
軟性に優れた柔軟剤の開発が望まれている。2. Description of the Related Art Conventionally, most commercial products for household softening agents use a quaternary ammonium salt represented by di (hardened beef tallow alkyl) dimethylammonium chloride as a main component. There is a problem in using it in the popular automatic washing machines. Since the fully automatic washing machine has a small bath ratio and a small number of rinses, the amount of anionic surfactant present in the bath during the softening treatment increases, and a quaternary ammonium salt having strong cationic property and an anion-cation complex are added. It has been found that the formation and softening effect is reduced. On the other hand, a method of using an amine having a slightly weak cationic property as a softener base is also known. For example, JP-A-52-05
Japanese Patent Publication No. 9796 discloses a composition using methyldi (hardened tallow alkyl) amine, but even this composition has a low softening effect and is not yet sufficient. Therefore, in softening treatment using a fully automatic washing machine, development of a softening agent having excellent flexibility is desired.
【0003】[0003]
【発明が解決しようとする課題】本発明は、衣料に対し
て柔軟性を付与すると同時に、全自動洗濯機に最適な柔
軟剤組成物を提供するものである。DISCLOSURE OF THE INVENTION The present invention provides a softener composition suitable for a fully automatic washing machine, while imparting flexibility to clothes.
【0004】[0004]
【課題を解決するための手段】本発明の柔軟剤組成物
は、下記(a)及び(b)成分をその配合重量比が
(a)/(b)=98/2〜60/40の範囲となるよ
うに含有することを特徴とする。In the softener composition of the present invention, the blending weight ratio of the following components (a) and (b) is (a) / (b) = 98/2 to 60/40. It is characterized by containing so that.
【0005】(a) 下記化2の一般式(I)及び/又
は(II)で示されるアミンの無機酸又は有機酸の中和物
からなるアミン系柔軟基剤。(A) An amine-based soft base comprising a neutralized product of an inorganic acid or an organic acid of an amine represented by the following general formula (I) and / or (II).
【化2】 [Chemical 2]
【0006】(b) 炭素数8〜22の飽和又は不飽和
の脂肪酸及び/又はその塩ならびにそれらの短鎖アルコ
ール又は短鎖ポリオールのエステルよりなる群から選ば
れる1種又は2種以上。(B) One or more selected from the group consisting of saturated or unsaturated fatty acids having 8 to 22 carbon atoms and / or salts thereof, and esters of short chain alcohols or short chain polyols thereof.
【0007】[0007]
【発明の実施態様】本発明の(a)成分としては、下記
化3の一般式(I)又は(II)で示されるアミンの無機
酸又は有機酸の中和物からなる柔軟基剤の1種または2
種以上が用いられる。BEST MODE FOR CARRYING OUT THE INVENTION As the component (a) of the present invention, 1 of a soft base comprising a neutralized product of an inorganic acid or organic acid of an amine represented by the following general formula (I) or (II) Seed or 2
More than one seed is used.
【0008】[0008]
【化3】 R8 ,R11,R12は、炭素数8〜22の直鎖もしくは分
岐鎖アルキル基又はアルケニル基であり、好ましくは炭
素数13〜19の直鎖もしくは分岐鎖アルキル基又はア
ルケニル基である。n,mは、2〜10の整数であり、
好ましくは2〜4の整数である。pは、0又は1〜7の
整数であり、好ましくは0である。qは、1〜10の整
数であり、好ましくは1〜2の整数である。R10は、
H,OHあるいは炭素数1〜6のアルキル基又はヒドロ
キシアルキル基であり、好ましくはHである。[Chemical 3] R 8, R 11, R 12 is a linear or branched alkyl or alkenyl group having 8 to 22 carbon atoms, preferably a straight-chain or branched alkyl or alkenyl group having 13 to 19 carbon atoms. n and m are integers of 2 to 10,
It is preferably an integer of 2 to 4. p is 0 or an integer of 1 to 7, preferably 0. q is an integer of 1 to 10, preferably an integer of 1 to 2. R 10 is
H, OH or an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group, and preferably H.
【0009】(a)成分のアミン系柔軟基剤の一般式
(I)及び(II)の具体例としては、以下の一般式で示
すものが挙げられる。 (1) 一般式(I)の具体例:化4、化5、化6の
(I−1)〜(I−9)Specific examples of the general formulas (I) and (II) of the amine type soft base as the component (a) include those represented by the following general formula. (1) Specific examples of general formula (I): (I-1) to (I-9) in Chemical formula 4, Chemical formula 5, and Chemical formula 6
【化4】 (上記一連の式中、nは2〜10の整数、qは1〜10
の整数を示す。)[Chemical 4] (In the above series of formulas, n is an integer of 2 to 10 and q is 1 to 10
Indicates an integer. )
【0010】[0010]
【化5】 (上記一連の式中、nは2〜10の整数、qは1〜10
の整数を示す。)[Chemical 5] (In the above series of formulas, n is an integer of 2 to 10 and q is 1 to 10
Indicates an integer. )
【0011】[0011]
【化6】 (上記一連の式中、nは2〜10の整数を示す。)[Chemical 6] (In the above series of formulas, n represents an integer of 2 to 10.)
【0012】(2) 一般式(II)の具体例:化7、化
8の(II−1)〜(II−8)(2) Specific examples of the general formula (II): (II-1) to (II-8) of Chemical formula 7 and Chemical formula 8
【化7】 (上記一連の式中、mは2〜10の整数、qは1〜10
の整数を示す。)[Chemical 7] (In the above series of formulas, m is an integer of 2 to 10, and q is 1 to 10
Indicates an integer. )
【0013】[0013]
【化8】 (上記一連の式中、mは2〜10の整数を示す。)[Chemical 8] (In the above series of formulas, m represents an integer of 2 to 10.)
【0014】前記の一般式(I),(II)中の脂肪酸残
基−COR8 ,−COR11,−COR12は通常、ステア
リン酸、パルミチン酸等の飽和高級脂肪酸、オレイン
酸、エライジン酸、リノール酸、リノレン酸等の不飽和
高級脂肪酸、牛脂、豚脂、パーム油、パーム核油、大豆
油、サフラワー油、ヒマワリ油、オリーブ油等の天然油
脂を分解、精製して得られる脂肪酸から由来するもので
あるが、この中でも特にオレイン酸、ステアリン酸、牛
脂脂肪酸、硬化牛脂脂肪酸、パーム油脂脂肪酸、硬化パ
ーム油脂脂肪酸、パーム核油脂脂肪酸、硬化パーム核油
脂脂肪酸が好適である。なお、不飽和脂肪酸としては、
立体異性体がシス体またはトランス体であつても、ある
いは両者の混合物であつてもよいが、特にシス体/トラ
ンス体の比率が25/75〜100/0(重量比)であ
ることが好ましい。The fatty acid residues --COR 8 , --COR 11 and --COR 12 in the above general formulas (I) and (II) are usually saturated higher fatty acids such as stearic acid and palmitic acid, oleic acid and elaidic acid, Derived from fatty acids obtained by decomposing and purifying natural fats and oils such as unsaturated higher fatty acids such as linoleic acid and linolenic acid, beef tallow, lard, palm oil, palm kernel oil, soybean oil, safflower oil, sunflower oil, olive oil and the like. Among them, oleic acid, stearic acid, tallow fatty acid, hardened beef tallow fatty acid, palm fat and oil fatty acid, hardened palm fat and oil fatty acid, palm kernel fat and oil fatty acid, and hardened palm kernel fat and oil fatty acid are particularly preferable. In addition, as the unsaturated fatty acid,
The stereoisomer may be a cis isomer or a trans isomer, or a mixture of the two, and the ratio of the cis isomer / trans isomer is preferably 25/75 to 100/0 (weight ratio). .
【0015】上記一般式(I),(II)のアミンは、通
常用いられる酸で中和されてアミン系柔軟基剤とされ
る。酸としては例えば、塩酸、硫酸、リン酸などの無機
塩や安息香酸、クエン酸、高分子アクリル酸等の有機酸
を挙げることができる。(a)成分のアミン系柔軟基剤
は、本発明の柔軟剤組成物中に3〜30重量%配合する
のが好適であり、好ましくは5〜15重量%配合され
る。(b)成分としては、炭素数8〜22の飽和又は
不飽和の脂肪酸、この脂肪酸の塩およびこの脂肪酸
と短鎖アルコール又は短鎖ポリオールとのエステルより
なる群から選ばれる1種又は2種以上が用いられる。The amines of the above general formulas (I) and (II) are neutralized with a commonly used acid to give an amine-based soft base. Examples of the acid include inorganic salts such as hydrochloric acid, sulfuric acid and phosphoric acid, and organic acids such as benzoic acid, citric acid and polymeric acrylic acid. The amine-based softening agent as the component (a) is preferably added in the softening agent composition of the present invention in an amount of 3 to 30% by weight, and preferably 5 to 15% by weight. As the component (b), one or more selected from the group consisting of a saturated or unsaturated fatty acid having 8 to 22 carbon atoms, a salt of this fatty acid, and an ester of this fatty acid and a short-chain alcohol or a short-chain polyol. Is used.
【0016】(b)成分の具体例としては、ラウリン
酸、ミリスチン酸、パルミチン酸、ステアリン酸、オレ
イン酸、エライジン酸、エルカ酸、牛脂脂肪酸、パーム
油脂肪酸、及びこれらそのナトリウム塩、カリウム塩、
置換または未置換のアンモニウム塩等が挙げられる。更
に上記脂肪酸とエステルを形成する適当なアルコールま
たは短鎖ポリオールの例としては、メタノール、エタノ
ール、イソプロパノール、エチレングリコール、グリセ
ロール、プロピレングリコールを挙げることができる。
(b)成分は、本発明の柔軟剤組成物中に、0.2〜
5.0重量%配合するのが好適であり、好ましくは2.
0〜3.0重量%配合される。Specific examples of the component (b) include lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, elaidic acid, erucic acid, tallow fatty acid, palm oil fatty acid, and their sodium salts and potassium salts.
Examples thereof include substituted or unsubstituted ammonium salts. Further examples of suitable alcohols or short chain polyols which form esters with the above fatty acids include methanol, ethanol, isopropanol, ethylene glycol, glycerol, propylene glycol.
The component (b) is added to the softener composition of the present invention in an amount of 0.2 to
It is suitable to add 5.0% by weight, preferably 2.
0 to 3.0% by weight is blended.
【0017】(a)成分と(b)成分とは、重量比で
(a)/(b)=98/2〜60/40、好ましくは9
0/10〜70/30の範囲で柔軟剤組成物中に配合さ
れる。この比率が98/2を越えると柔軟性が低下し、
一方60/40未満では柔軟性付与効果が極端に低下す
るので好ましくない。The weight ratio of component (a) and component (b) is (a) / (b) = 98 / 2-60 / 40, preferably 9
It is compounded in the softener composition in the range of 0/10 to 70/30. If this ratio exceeds 98/2, the flexibility decreases,
On the other hand, if it is less than 60/40, the effect of imparting flexibility is extremely reduced, which is not preferable.
【0018】本発明の柔軟剤組成物には、上記成分以外
にその他の任意成分として、通常柔軟剤組成物に配合さ
れる公知の成分を本発明の効果を妨げない範囲で配合す
ることができる。任意成分としては、例えば、ジ長鎖ア
ルキルジ短鎖アルキル第4級アンモニウム塩等の第4級
アンモニウム塩、高級アルコールまたはモノアルキルア
ミンのアルキレンオキシド付加物等の非イオン界面活性
剤、食塩、塩化アンモニウム、塩化カルシウム、塩化マ
グネシウム、塩化カリウム等の水溶性塩、エチルアルコ
ール、イソプロピルアルコール、エチレングリコール、
プロピレングリコール、イソプレングリコール、ヘキシ
レングリコール等の溶剤、尿素、殺菌剤、酸化防止剤、
染料、顔料、シリコーン類、炭化水素、セルロース誘導
体、紫外線吸収剤、蛍光増白剤、香料等が挙げられる。In addition to the above-mentioned components, the softener composition of the present invention may contain, as other optional components, known components which are usually incorporated in the softener composition, within a range that does not impair the effects of the present invention. . Examples of the optional component include quaternary ammonium salts such as dilong-chain alkyldishort-chain alkyl quaternary ammonium salts, nonionic surfactants such as higher alcohols or alkylene oxide adducts of monoalkylamines, sodium chloride, and ammonium chloride. , Water-soluble salts such as calcium chloride, magnesium chloride, potassium chloride, ethyl alcohol, isopropyl alcohol, ethylene glycol,
Solvents such as propylene glycol, isoprene glycol, hexylene glycol, urea, bactericides, antioxidants,
Examples thereof include dyes, pigments, silicones, hydrocarbons, cellulose derivatives, ultraviolet absorbers, optical brighteners and fragrances.
【0019】[0019]
【発明の効果】本発明によれば、(a)成分のアミン系
柔軟基剤と、(b)成分の炭素数8〜22の飽和又は不
飽和の脂肪酸、その塩およびその短鎖アルコール又は短
鎖ポリオールとのエステルよりなる群から選ばれる1種
又は2種以上とを特定比率で併用して柔軟剤組成物とす
ることにより、洗濯サイクルから持ち込まれるアニオン
界面活性剤の存在下でも衣料に対して柔軟性を付与する
ことができ、特に全自動洗濯機での使用に好適である。According to the present invention, the amine type soft base as the component (a) and the saturated or unsaturated fatty acid having 8 to 22 carbon atoms as the component (b), its salt and its short chain alcohol or short chain. By using together with one kind or two or more kinds selected from the group consisting of esters with chain polyols in a specific ratio, a softening agent composition can be obtained, even in the presence of an anionic surfactant brought in from a washing cycle, with respect to clothing. It can impart flexibility and is particularly suitable for use in a fully automatic washing machine.
【0020】[0020]
【実施例】以下、実施例により本発明をさらに詳細に説
明するが、それに先立つて実施例で採用した評価方法を
説明する。EXAMPLES The present invention will be described in more detail with reference to examples below, but prior to that, the evaluation methods adopted in the examples will be described.
【0021】(1) 柔軟化処理方法 木綿として市販の綿タオルを、また、化学繊維としてア
クリルジャージを用い、市販衣料用洗剤「ハイトツプ」
(ライオン(株)製)により電気洗濯機を用いて50℃
で2回繰り返し洗濯後、常温の水道水で1回すすぎ、こ
れを試験布とした。次に、25℃の水道水30リツトル
に対し、(a)成分と(b)成分の合計量として1gに
なるように柔軟剤組成物を加えて均一溶液とした。この
溶液中に浴比30倍で綿タオルとアクリルジャージの比
率を7/3として各試験布を浸し3分間処理した後、2
分間脱水した。このように処理した布を風乾した後、2
5℃、65%RHの条件で24時間放置し、評価試験に
用いた。(1) Softening treatment method A commercially available cotton towel, and an acrylic jersey as a chemical fiber are used, and a commercial clothing detergent "HITOPUP" is used.
(Lion Co., Ltd.) using an electric washing machine at 50 ℃
After being repeatedly washed twice, the test cloth was rinsed once with room temperature tap water. Next, the softener composition was added to 30 liters of tap water at 25 ° C. so that the total amount of the components (a) and (b) would be 1 g to prepare a uniform solution. Each test cloth was dipped in this solution with a bath ratio of 30 times and the ratio of cotton towel and acrylic jersey was 7/3, and treated for 3 minutes, and then 2
Dehydrated for a minute. After air-drying the thus treated cloth, 2
It was left for 24 hours under the conditions of 5 ° C. and 65% RH and used for the evaluation test.
【0022】(2) 柔軟性評価方法 ジメチルジステアリル第4級アンモニウムクロライドを
柔軟剤基剤として配合した柔軟剤組成物で処理した布を
対照にして一対比較を行い、下記基準にて5名が評価
し、平均値を評価結果とした。 +2:対照より柔らかい +1:対照よりやや柔らかい 0:対照と同じ −1:対照の方がやや柔らかい −2:対照の方が柔らかい(2) Softness Evaluation Method A pair of comparisons were carried out with a cloth treated with a softening agent composition containing dimethyl distearyl quaternary ammonium chloride as a softening agent base, and 5 people were evaluated according to the following criteria. It evaluated and made the average value the evaluation result. +2: Softer than control +1: Slightly softer than control 0: Same as control -1: Slightly softer control -2: Softer control
【0023】実施例1〜7、比較例1〜4 以下に表1に示した(a)成分と(b)成分とを用い、
表2に示した柔軟基剤を含有する柔軟剤組成物を調製し
て柔軟性を評価し、その結果を表2に示した。Examples 1 to 7 and Comparative Examples 1 to 4 Using the components (a) and (b) shown in Table 1 below,
The softening agent composition containing the softening agent shown in Table 2 was prepared and the softness was evaluated, and the results are shown in Table 2.
【0024】[0024]
【表1】表1:(a)成分及び(b)成分 記号 化合物名 a成分: a−1 (I−1)式でn=3、q=1の塩酸中和物(ジエステルジアミン) a−2 (I−2)式でn=3、q=1の塩酸中和物(ジエステルジアミン) a−3 (I−6)式でn=3、q=1の塩酸中和物(ジエステルジアミン) a−4 (I−7)式でn=3の塩酸中和物(ジアミドジアミン) a−5 (II−1)式でm=3、q=1の塩酸中和物(アミドエステルアミン) a−6 (II−6)式でm=3の塩酸中和物(ジアミドアミン) a−7 (I−1)式でn=15、q=15の塩酸中和物(比較品) a−8 ジメチルジステアリル第4級アンモニウムクロライド(対照) b成分: b−1 ステアリン酸 b−2 ジパルミチン酸エチレングリコールエステル b−3 トリステアリン酸グルセロールエステル b−4 オレイン酸エタノールエステル b−5 パルミチン酸メタノールエステル [Table 1]Table 1: (a) component and (b) component symbol Compound name Component a: a-1 (I-1) n = 3, q = 1 hydrochloric acid neutralized product (diesterdiamine) a-2 (I-2) n = 3, q = 1 hydrochloric acid neutralized (Diester diamine) a-3 (I-6) formula, n = 3, q = 1 neutralized hydrochloric acid (diester diamine) a-4 (I-7) formula, n = 3 hydrochloric acid neutralized product ( Diamidediamine) a-5 (II-1) formula, m = 3, q = 1 hydrochloric acid neutralized product (amidoesteramine) a-6 (II-6) formula, m = 3 hydrochloric acid neutralized product (diamine Amidoamine) a-7 (I-1) formula, n = 15, q = 15 hydrochloric acid neutralized product (comparative product) a-8 dimethyl distearyl quaternary ammonium chloride (control) Component b: b-1 stearic acid b-2 dipalmitic acid ethylene glycol ester b-3 tristearic acid glycerol ester b-4 oleic acid ethanol ester b-5 Palmitic acid methanol ester
【0025】[0025]
【表2】表2:基剤組成及び評価結果 (a)成分 (b)成分 (a)/(b) 評価結果:柔軟性 化合物 化合物 重量比 木綿 アクリル 実施例1 a−1 b−1 90/10 +1.2 +2.0 比較例1 a−1 − 100/0 0 +0.8 比較例2 − b−1 0/100 −2.0 −2.0 比較例3 a−1 b−1 50/50 −0.8 +2.0 比較例4 a−7 b−1 70/30 −1.2 +1.0 実施例2 a−1 b−2 80/20 +1.2 +1.4 実施例3 a−2 b−3 65/35 +1.4 +1.8 実施例4 a−3 b−1 80/20 +1.0 +1.6 実施例5 a−4 b−4 90/10 +1.8 +1.2 実施例6 a−5 b−5 85/15 +2.0 +1.0 実施例7 a−6 b−2 80/20 +1.0 +1.2 対照 a−8 − − 基準 基準 [Table 2] Table 2: Composition of base material and evaluation results (a) component (b) component (a) / (b) evaluation result: flexible compound compound weight ratio cotton acrylic Example 1 a-1 b-1 90 / 10 +1.2 +2.0 Comparative example 1 a-1 −100/0 0 +0.8 Comparative example 2 −b−10 / 100 −2.0 −2.0 Comparative example 3 a−1 b−1 50/50 −0.8 +2 .0 Comparative Example 4 a-7 b-1 70/30 -1.2 +1.0 Example 2 a-1 b-2 80/20 +1.2 +1.4 Example 3 a-2 b-3 65/35 +1 .4 +1.8 Example 4 a-3 b-1 80/20 +1.0 +1.6 Example 5 a-4 b-4 90/10 +1.8 +1.2 Example 6 a-5 b-5 85/15 +2.0 +1.0 Example 7 a-6 b-2 80/20 +1.0 +1.2 Control a-8 − − Standard Standard
フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 FI 技術表示箇所 D06M 13/332 13/372 13/419 D06M 13/40 Continuation of front page (51) Int.Cl. 6 Identification number Office reference number FI technical display location D06M 13/332 13/372 13/419 D06M 13/40
Claims (1)
又は(II)で示されるアミンの無機酸又は有機酸の中和
物からなるアミン系柔軟基剤 【化1】 及び(b) 炭素数8〜22の飽和又は不飽和の脂肪酸
及び/又はその塩ならびにそれらの短鎖アルコール又は
短鎖ポリオールのエステルよりなる群から選ばれる1種
又は2種以上を含有し、(a)及び(b)成分の配合重
量比が(a)/(b)=98/2〜60/40の範囲に
あることを特徴とする柔軟剤組成物。1. (a) General formula (I) and //
Alternatively, an amine-based soft base consisting of a neutralized product of an inorganic or organic acid of amine represented by (II) And (b) containing one or more selected from the group consisting of saturated or unsaturated fatty acids having 8 to 22 carbon atoms and / or salts thereof and esters of short chain alcohols or short chain polyols thereof, ( A softener composition, wherein the blending weight ratio of the components (a) and (b) is in the range of (a) / (b) = 98/2 to 60/40.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP18704893A JPH0718569A (en) | 1993-06-29 | 1993-06-29 | Softening agent composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP18704893A JPH0718569A (en) | 1993-06-29 | 1993-06-29 | Softening agent composition |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH0718569A true JPH0718569A (en) | 1995-01-20 |
Family
ID=16199267
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP18704893A Pending JPH0718569A (en) | 1993-06-29 | 1993-06-29 | Softening agent composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0718569A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6596685B2 (en) | 2000-01-19 | 2003-07-22 | Kao Corporation | Softener composition |
WO2006040332A1 (en) * | 2004-10-13 | 2006-04-20 | Clariant Finance (Bvi) Limited | Fatty acid esters of alkanolamines and their use as softening agents |
WO2010108108A3 (en) * | 2009-03-20 | 2011-04-07 | Egen, Inc. | Polyamine derivatives |
US10167253B2 (en) | 2015-06-24 | 2019-01-01 | Nitto Denko Corporation | Ionizable compounds and compositions and uses thereof |
-
1993
- 1993-06-29 JP JP18704893A patent/JPH0718569A/en active Pending
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6596685B2 (en) | 2000-01-19 | 2003-07-22 | Kao Corporation | Softener composition |
US7202203B2 (en) | 2000-01-19 | 2007-04-10 | Kao Corporation | Softener composition |
WO2006040332A1 (en) * | 2004-10-13 | 2006-04-20 | Clariant Finance (Bvi) Limited | Fatty acid esters of alkanolamines and their use as softening agents |
WO2010108108A3 (en) * | 2009-03-20 | 2011-04-07 | Egen, Inc. | Polyamine derivatives |
US8900621B2 (en) | 2009-03-20 | 2014-12-02 | Clsn Laboratories, Inc. | Polyamine derivatives |
US8932638B2 (en) | 2009-03-20 | 2015-01-13 | Clsn Laboratories, Inc. | Polyamine derivatives |
JP2015147927A (en) * | 2009-03-20 | 2015-08-20 | エーゲン、インコーポレイテッド | Polyamine derivatives |
US9254334B2 (en) | 2009-03-20 | 2016-02-09 | Clsn Laboratories, Inc. | Polyamine derivatives |
US10167253B2 (en) | 2015-06-24 | 2019-01-01 | Nitto Denko Corporation | Ionizable compounds and compositions and uses thereof |
US11384051B2 (en) | 2015-06-24 | 2022-07-12 | Nitto Denko Corporation | Ionizable compounds and compositions and uses thereof |
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