JP2951778B2 - Liquid soft finish - Google Patents

Liquid soft finish

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Publication number
JP2951778B2
JP2951778B2 JP29585791A JP29585791A JP2951778B2 JP 2951778 B2 JP2951778 B2 JP 2951778B2 JP 29585791 A JP29585791 A JP 29585791A JP 29585791 A JP29585791 A JP 29585791A JP 2951778 B2 JP2951778 B2 JP 2951778B2
Authority
JP
Japan
Prior art keywords
acid
amine
chain
neutralized
soft finish
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.)
Expired - Fee Related
Application number
JP29585791A
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Japanese (ja)
Other versions
JPH05132861A (en
Inventor
徹 早瀬
和隆 白土
正明 山村
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kao Corp
Original Assignee
Kao Corp
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Filing date
Publication date
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Priority to JP29585791A priority Critical patent/JP2951778B2/en
Publication of JPH05132861A publication Critical patent/JPH05132861A/en
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Publication of JP2951778B2 publication Critical patent/JP2951778B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Description

【発明の詳細な説明】DETAILED DESCRIPTION OF THE INVENTION

【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)を付与できる家庭用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 soft finish, and more particularly to a liquid soft finish for domestic use which can impart excellent flexibility and elasticity (fluffiness) 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物である。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
Most of the products marketed as household softeners are mostly 1
The composition is mainly composed of a quaternary ammonium salt having 1 to 2 long-chain alkyl groups in the molecule. The reason for this is that the quaternary ammonium salt has a good softening effect on various fibers in a small amount.

【0003】上記の第4級アンモニウム塩は、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。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。
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。
[0003] The above quaternary ammonium salts have a remarkable softening effect on cotton, but acrylic,
It is hard to say that the effect is sufficient for synthetic fibers such as polyester-based and polyamide-based fibers. If the treatment is performed at a higher concentration, the elasticity of the garment may be reduced and the texture may be impaired. In the case of long-term storage, the viscosity may increase, the gel may be formed, or the polymer may be separated, particularly at a low temperature.
For this reason, various polyoxyethylene-based nonionic activators, electrolytes, and solvents other than the soft component are required, and many of them require stabilization by blending them, but the effect is still insufficient.

【0004】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。しかしながら、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、撹拌力
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。
[0004] Soft finishes based on the above quaternary ammonium salts are usually marketed as 4-20% dispersions,
in use. However, since the quaternary ammonium salt has a strong hydrophobicity, when it is poured into rinse water, if the stirring power is weak, the quaternary ammonium salt has poor dispersibility in water, and thus may be uneven to clothing. Commercially available softeners incorporate various additives in addition to the above quaternary ammonium salts to improve dispersibility in water, but their effects are still insufficient.

【0005】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52−59
7965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61−167083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
体担体を含む柔軟化組成物が、特開平2−6662号公報に
はヒドロキシ低級アルキルアルキレンジアミンと高級脂
肪酸の縮合物等のアミン及び両性布地コンディショニン
グ剤を含有する布地コンディショニング組成物が、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。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を含有する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。
[0005] In addition, liquid softeners based on various amines as softer bases have been known. For example, JP-A-52-59
JP-A-7965 discloses a composition for imparting flexibility to a fiber containing a long-chain alkylamine such as methyldi (hardened tallowalkyl) amine. JP-A-58-60070 discloses an acylated alkanolamine, Japanese Patent Application Laid-Open No. Sho 61-167083 discloses a fiber material finishing agent which imparts smoothness and a comfortable hand to fibers containing a quaternary ammonium salt and a fatty acid ester. A good dispersing softener containing a polyamine polyglycol ether is disclosed in JP-A-61-275474. A stable aqueous dispersion for treating textiles containing a di (higher alkyl) cyclic amine and Bronsted acid is disclosed in JP-A-61-275474. , JP
JP-A 64-85368 discloses a softening composition comprising a dilong-chain alkylamine-anionic surfactant ion-pair complex, a non-silicone wax and a liquid carrier, and JP-A-2-6662 discloses a hydroxy lower alkyl group. A fabric conditioning composition containing an amine such as a condensate of an alkylenediamine and a higher fatty acid and an amphoteric fabric conditioning agent is disclosed in Japanese Unexamined Patent Publication (Kokai) No. 2-14076, a softener containing a dilong chain alkylamine-polyfunctional carboxylic acid complex. And fabric conditioning compositions that impart antistatic properties. Further, Japanese Patent Application Laid-Open No. 52-5394 describes a fabric conditioning composition containing an antistatic agent containing a mono- or dilong-chain alkylalkylenediamine and a quaternary ammonium softener.

【0006】これらの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。また最近、全世界的に環境への
影響を危惧する声が高まって来ており、柔軟仕上剤にお
いても生分解性等に優れている基剤が望まれ始めてい
る。しかしながら、上に示したこれらのアミンを含有す
る柔軟剤はこの点においても効果は未だ十分でない。
Although these amine-containing softeners are relatively better in dispersibility and storage stability than quaternary ammonium salt-containing softeners, their softening performance is still insufficient. In recent years, there has been an increasing worldwide concern about the impact on the environment, and a base material having excellent biodegradability and the like has also been desired for a soft finish. However, the above-mentioned softeners containing amines are still not sufficiently effective in this regard.

【0007】[0007]

【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上記課題を解決すべく鋭意研究
の結果、特定の(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、本発明に至った。
Means for Solving the Problems The inventors of the present invention have conducted intensive studies on amine-containing softeners to solve the above-mentioned problems, and as a result, a neutralized product of a specific (dilong chain type) amine compound or a quaternary amine compound It has been found that the compound has excellent flexibility and can impart elasticity (fluffiness) to clothing, and has reached the present invention.

【0008】即ち、本発明は、下記の一般式(A) で表さ
れる化合物の無機酸若しくは有機酸の中和物又は4級化
物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。
[0008] That is, the present invention provides a liquid softener comprising, as an essential component, a neutralized or quaternized inorganic or organic acid of a compound represented by the following general formula (A). Is provided.

【0009】[0009]

【化2】 Embedded image

【0010】〔式中、R1,R2は炭素数11〜23、好ましく
は13〜21、特に好ましくは15〜19の直鎖又は分岐の飽和
又は不飽和炭化水素基、R はヒドロキシル基等の置換基
を有していてもよい炭素数1〜24、好ましくは1〜3の
直鎖又は分岐の飽和又は不飽和炭化水素基、m は4〜
8、n は1〜6、好ましくは1〜3の数を表す。〕。
Wherein R 1 and R 2 are straight-chain or branched saturated or unsaturated hydrocarbon groups having 11 to 23 carbon atoms, preferably 13 to 21 carbon atoms, particularly preferably 15 to 19 carbon atoms, and R is a hydroxyl group or the like. A linear or branched saturated or unsaturated hydrocarbon group having 1 to 24, preferably 1 to 3 carbon atoms, which may have a substituent;
8, n represents a number of 1 to 6, preferably 1 to 3. ].

【0011】本発明に用いられる一般式(A) で表される
アミンの代表例としては、N−メチル−N−ヒドロキシ
ルプロピルアミノエチルアミン等のアミン化合物と、炭
素数12〜24の脂肪酸又は脂肪酸メチルエステルとの反応
により得られるエステルアミン等が挙げられる。この反
応に用いられる脂肪酸又は長鎖アルコール、長鎖アミン
としては、ヤシ油、パーム油、牛脂、ナタネ油、魚油等
の天然由来のものが一般的であるが、化学的に合成した
脂肪酸又は長鎖アルコール、長鎖アミンでもよい。ま
た、かかる一般式(A) で表されるアミンの中和物を得る
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が挙げ
られる。また、4級化物を得るための4級化剤として
は、CH3Cl 等が挙げられる。本発明において、一般式
(A) で表されるアミンの中和物又は4級化物は液体柔軟
仕上剤中に4〜40重量%、好ましくは6〜30重量%、特
に好ましくは10〜25重量%配合されるのが望ましい。
Representative examples of the amine represented by the general formula (A) used in the present invention include amine compounds such as N-methyl-N-hydroxylpropylaminoethylamine and fatty acids having 12 to 24 carbon atoms or fatty acid methyl. And esteramines obtained by reaction with esters. The fatty acids or long-chain alcohols and long-chain amines used in this reaction are generally of natural origin such as coconut oil, palm oil, tallow, rapeseed oil, fish oil, etc. It may be a chain alcohol or a long chain amine. Examples of the acid for obtaining the neutralized product of the amine represented by the general formula (A) include inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, and phosphoric acid, acetic acid, lactic acid, glycolic acid, citric acid, and maleic acid. Organic acids such as acid, fumaric acid, and toluenesulfonic acid are exemplified. Further, as a quaternizing agent for obtaining a quaternized product, CH 3 Cl or the like can be mentioned. In the present invention, the general formula
The neutralized or quaternized amine represented by (A) is incorporated in the liquid softener in an amount of 4 to 40% by weight, preferably 6 to 30% by weight, particularly preferably 10 to 25% by weight. desirable.

【0012】本発明の液体柔軟仕上剤は、例えば一般式
(A) で表されるアミン化合物の溶融物又は濃厚液を撹拌
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 is, for example, a compound represented by the general formula
(A) is obtained by slowly adding a melt or a concentrated solution of the amine compound represented by (A) to an aqueous solution containing a neutralizing agent under stirring or shear mixing, but is not limited to this method. It can also be obtained by a method in which a neutralized product is produced in advance or a neutralized product is added later.

【0013】一般式(A) で表されるアミン化合物はエス
テル基を分子内に持っていることから、生分解性に優れ
ており、自然環境に対しても考慮された新しい柔軟基剤
であることも特徴の一つである。
The amine compound represented by the general formula (A) has an ester group in the molecule, so that it is excellent in biodegradability and is a new flexible base which is also considered in the natural environment. This is one of the features.

【0014】本発明の柔軟仕上剤に、更にジメチルポリ
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一
般式(A) で表されるアミンの中和物又は4級化物に対し
0.3 〜5重量%配合されるのが好ましい。
The soft finish of the present invention may further comprise a silicone compound such as dimethylpolysiloxane, dimethylpolysiloxane partially modified with an amino group or a polyoxyalkylene group, particularly preferably partially modified with a polyoxyalkylene group. By blending the dimethylpolysiloxane thus obtained, it is possible to improve the feel of soft-treated clothing without impairing water absorption. These silicone compounds react with neutralized or quaternized amines represented by the general formula (A).
It is preferable to add 0.3 to 5% by weight.

【0015】本発明の柔軟仕上剤は、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
ドに比較すると柔軟効果はほぼ同等であるが、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。
The softening agent of the present invention has almost the same softening effect as the hardened tallow alkyldimethylammonium chloride which has been widely used in the past, but surprisingly, it can obtain elastic softness. Do you get it.

【0016】本発明の組成物を水系液体柔軟仕上剤とす
る際には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。
When the composition of the present invention is used as an aqueous liquid softening agent, an inorganic electrolyte such as sodium chloride, calcium chloride or magnesium chloride is used in an amount of 0.05 to 0.4 to adjust the viscosity.
It is desirable to add by weight.

【0017】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、ポリオキシエチレン(5〜50モル)アルキル
(C12〜C24)アミン等のノニオン界面活性剤、エタノー
ル、エチレングリコール、プロピレングリコール、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、長鎖脂肪酸等を
併用しても良い。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螢光増白剤を、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。
Although the liquid softener of the present invention has high stability for long-term storage, it is also preferable to use polyoxyethylene (5 to 50 mol) alkyl or alkenyl (C 12 ) for stabilization under severe storage conditions. -C 24) ethers or polyoxypropylene (5-50 moles) alkyl or alkenyl (C 12 -C 24)
Ether, polyoxyethylene (5-50 mol) alkyl
A nonionic surfactant such as (C 12 -C 24 ) amine , a solvent such as ethanol, ethylene glycol, propylene glycol, and glycerin, or urea can be blended. Further, known esters, nonionic or cationic compounds, long-chain alcohols, long-chain fatty acids and the like may be used in combination as a soft base. Also, pigments or dyes can be compounded for the appearance of the product, optical brighteners for the whiteness of the finished product, and fragrances can be added to improve the taste at the time of use and after the finished product.

【0018】[0018]

【発明の効果】本発明の柔軟仕上剤は各種繊維に対し
て、十分な柔軟性、帯電防止性を与え、且つ優れた弾力
性を付与し得ると共に生分解性に優れている。
As described above, the softening agent of the present invention can impart sufficient flexibility and antistatic properties to various fibers, can provide excellent elasticity, and is excellent in biodegradability.

【0019】[0019]

【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。
Next, the present invention will be described in detail with reference to examples, but the present invention is not limited to these examples.

【0020】実施例1〜6及び比較例1 表1に示す構造を有する一般式(A) で表される化合物の
中和物又は4級化物を表2に示す配合量で用いて調製し
た液体柔軟仕上剤を用い、以下の評価を行った。
Examples 1 to 6 and Comparative Example 1 Liquids prepared using neutralized or quaternized compounds of the general formula (A) having the structure shown in Table 1 in the amounts shown in Table 2 The following evaluation was performed using the soft finish.

【0021】[0021]

【表1】 [Table 1]

【0022】<液体柔軟仕上剤の調製方法>50℃の水の
中に、攪拌下にて(a) 成分のアミンの溶融物を添加し、
次いで酸を加えることによりアミン中和物の分散液を得
た。また、4級化物の場合は、50℃の水の中に、攪拌下
にて、(a) 成分のアミン4級化物の溶融物を添加し、4
級化物の分散液を得た。 1) 柔軟性、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の配合
組成物を有効成分として 1.5g投入し、25℃、1分間撹
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
恒温恒湿室にて24時間放置した。これらの布について柔
軟性、弾力性の評価を行った。柔軟性、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;対照より柔らかい又は弾力性が高い +1;対照よりやや柔らかい又は弾力性がやや高い 0;対照と同じ −1;対照の方がやや柔らかい又は対照より弾力性がや
や低い −2;対照の方が柔らかい又は対照より弾力性が低い
<Method for Preparing Liquid Soft Finish> A melt of the amine (a) is added to water at 50 ° C. with stirring.
Then, an acid was added to obtain a dispersion of the neutralized amine. In the case of a quaternized product, a melt of the amine quaternized product (a) is added to 50 ° C. water with stirring.
A graded dispersion was obtained. 1) Evaluation of flexibility and elasticity (1) Treatment method 2 kg of commercially available cotton towel and 1 kg of acrylic jersey are 3.5 °
After washing 5 times repeatedly (30 liter washing machine) with a commercially available detergent attack (manufactured by Kao Corporation, registered trademark) in DH hard water to remove the fiber treating agent attached to each fiber, the composition of Table 2 was used. 1.5 g of the active ingredient was added, and the mixture was treated under stirring at 25 ° C. for 1 minute. (2) Evaluation method The cloth treated by the above method was air-dried in a room, and then left in a constant temperature and humidity room at 25 ° C. and 65% RH for 24 hours. These fabrics were evaluated for flexibility and elasticity. The evaluation of flexibility and elasticity was performed by comparing one pair of fabrics treated with 10 cc of a soft finishing agent comprising 15% by weight of dihydrogenated tallow alkyldimethylammonium chloride as a control. The evaluation is expressed as follows. +2; softer or more elastic than control +1; slightly softer or slightly more elastic than control 0; same as control -1; control slightly softer or slightly less elastic than control -2; control Is soft or less elastic than control

【0023】[0023]

【表2】 [Table 2]

【0024】実施例7〜9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1〜6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分間加圧した後、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 7 to 9 and Comparative Example 2 In order to evaluate the elasticity of the compositions having the compositions shown in Table 3, the pile height of cotton towels was measured. <Evaluation of Elasticity> Cotton towels treated in the same manner as in Examples 1 to 6 were folded in eight, three sheets were stacked and stacked, and 5 g / cm 2.
After 5 minutes of pressurizing, the pressure was removed and the height of the towel was measured. The higher the height of the towel, the better the elasticity.

【0025】[0025]

【表3】 [Table 3]

Claims (1)

(57)【特許請求の範囲】(57) [Claims] 【請求項1】 下記の一般式(A) で表される化合物の無
機酸若しくは有機酸の中和物又は4級化物を必須成分と
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は炭素数11〜23の直鎖又は分岐の飽和又
は不飽和炭化水素基、 R は置換基を有していてもよい炭素数1〜24の直鎖又は
分岐の飽和又は不飽和炭化水素基、m は4〜8、n は1
〜6の数を表す。〕
1. A liquid softener comprising, as an essential component, a neutralized or quaternized inorganic or organic acid of a compound represented by the following general formula (A). Embedded image [Wherein, R 1 and R 2 are linear or branched saturated or unsaturated hydrocarbon groups having 11 to 23 carbon atoms, and R is linear or branched having 1 to 24 carbon atoms which may have a substituent. A is a saturated or unsaturated hydrocarbon group, m is 4 to 8, n is 1
Represents the number of ]
JP29585791A 1991-11-12 1991-11-12 Liquid soft finish Expired - Fee Related JP2951778B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP29585791A JP2951778B2 (en) 1991-11-12 1991-11-12 Liquid soft finish

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP29585791A JP2951778B2 (en) 1991-11-12 1991-11-12 Liquid soft finish

Publications (2)

Publication Number Publication Date
JPH05132861A JPH05132861A (en) 1993-05-28
JP2951778B2 true JP2951778B2 (en) 1999-09-20

Family

ID=17826092

Family Applications (1)

Application Number Title Priority Date Filing Date
JP29585791A Expired - Fee Related JP2951778B2 (en) 1991-11-12 1991-11-12 Liquid soft finish

Country Status (1)

Country Link
JP (1) JP2951778B2 (en)

Also Published As

Publication number Publication date
JPH05132861A (en) 1993-05-28

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