JPH04108177A - Softening finish - Google Patents

Softening finish

Info

Publication number
JPH04108177A
JPH04108177A JP22174690A JP22174690A JPH04108177A JP H04108177 A JPH04108177 A JP H04108177A JP 22174690 A JP22174690 A JP 22174690A JP 22174690 A JP22174690 A JP 22174690A JP H04108177 A JPH04108177 A JP H04108177A
Authority
JP
Japan
Prior art keywords
acid
neutralized
compound
elasticity
tertiary amine
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
Application number
JP22174690A
Other languages
Japanese (ja)
Other versions
JPH0726325B2 (en
Inventor
Masaaki Yamamura
正明 山村
Junichi Inokoshi
猪腰 淳一
Kazutaka Shirato
和隆 白土
Toru Hayase
徹 早瀬
Toru Kato
徹 加藤
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
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Kao Corp filed Critical Kao Corp
Priority to JP22174690A priority Critical patent/JPH0726325B2/en
Publication of JPH04108177A publication Critical patent/JPH04108177A/en
Publication of JPH0726325B2 publication Critical patent/JPH0726325B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Abstract

PURPOSE:To provide the title finish capable of imparting various kinds of textiles with excellent flexibility, antistatic nature and elasticity, containing an inorganic or 1-6C organic acid-neutralized or quaternarized product of a specific (di-long chain) tertiary amine. CONSTITUTION:The objective water-based finish with good storage stability for a long period of time, containing, as softening base material, 4-40wt.% of an inorganic or 1-6C organic acid(pref. hydrochloric acid)-neutralized or quaternarized product of a tertiary amine compound of the formula (R<1> and R<2> are each 12-22C alkyl or alkenyl; R<3> is H, methyl or hydroxyethyl; m is 1 or 2). Said tertiary amine compound is pref. such that R<3> in the formula is H or hydroxyethyl group.

Description

【発明の詳細な説明】 〔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。
[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to a fabric softener, and more specifically, a liquid fabric softener that can impart excellent flexibility and elasticity (fluffiness) to various fibers. It is related to.

〔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。
[Problems to be solved by conventional techniques and inventions] Currently,
Most commercially available household fabric softeners contain quaternary ammonium salts with two long-chain alkyl groups in each molecule, such as di(hardened tallow alkyl)dimethylammonium chloride. It is a composition with

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。
The reason for this is that a small amount of quaternary ammonium salt has a good softening effect on various fibers.

しかしながら、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。
However, although the above-mentioned quaternary ammonium salts have a remarkable softening effect on cotton, it is difficult to say that the effect is sufficient on synthetic fibers such as acrylic, polyester, and polyamide. If treated at an even higher concentration, the elasticity of clothing may decrease and the texture may be impaired.

更に、上記第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。また、特に低温で長期保存をする場合は、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。
Furthermore, since the quaternary ammonium salt has strong hydrophobicity, if the agitation force is weak when adding it to the rinsing water, the dispersibility in water is poor, and therefore there is a risk that it will be uneven on clothing. In addition, especially when stored for a long time at low temperatures, it may thicken, become gel-like, or separate.

市販の柔軟剤は上記の第4級アンモニウム塩の他にポリ
オキシエチレン系の非イオン界面活性剤、電解質及び溶
剤等の添加側を配合し、水への分散性及び長期保存安定
性を改良しているが、その効果は未だ不充分である。
Commercially available softeners contain additives such as polyoxyethylene nonionic surfactants, electrolytes, and solvents in addition to the above-mentioned quaternary ammonium salts to improve dispersibility in water and long-term storage stability. However, the effects are still insufficient.

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52−59796
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61167083
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との縮合反応物及びア
ルキル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イシ
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性、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。
Furthermore, liquid softeners using various amines as softening bases have been known. For example, JP-A-52-59796
JP-A-58-60070 discloses a composition that imparts flexibility to fibers containing a long-chain alkylamine such as methyldi(hardened tallow alkyl)amine, and JP-A-58-60070 discloses a composition that imparts flexibility to fibers containing a long-chain alkylamine such as methyldi(hardened tallow alkyl)amine. A textile material finishing agent containing a quaternary ammonium salt and a fatty acid ester that gives smoothness and a comfortable touch is disclosed in JP-A No. 61167083.
JP-A No. 61-275474 discloses a softening agent with good dispersibility containing a quaternary ammonium compound, a condensation reaction product of a higher fatty acid and a hydroxy-lower alkyl polyamine, and an alkylamine polyglycol ether; A stable aqueous dispersion containing a (higher alkyl)cyclic amine and a Brønsted acid for treating textiles was disclosed in JP-A-64
JP-A-85368 discloses a softening composition containing a di-long-chain alkylamine-anionic surfactant ion pair complex, a non-silicone wax, and a liquid carrier; A fabric conditioning composition containing an amine such as a condensate of a diamine and a higher fatty acid and an amphoteric fabric conditioning agent is disclosed in JP-A-2-14076, a fabric conditioning composition containing a di-long chain alkylamine-polyfunctional carboxylic acid complex. Fabric conditioning compositions have been described that provide antistatic and antistatic properties.

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, JP-A-52-5394 describes a fabric conditioning composition containing a mono- or di-long chain alkyl alkylene diamine static electricity suppressant and a quaternary ammonium softener.

しかしながら、これらアミンを含有する柔軟剤は分散性
、保存安定性は第4級アンモニウム塩を含有する柔軟剤
に比べ比較的良いが、柔軟性能は未だ充分でない。
However, although these amine-containing softeners have relatively better dispersibility and storage stability than those containing quaternary ammonium salts, their softening ability is still insufficient.

〔課題を解決するための手段〕[Means to solve the problem]

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
っくら惑)を付与できることを見出し、本発明を完成す
るに至った。
As a result of extensive research into fabric softeners containing amines, the present inventors found that neutralized or quaternized products of special (di-long chain type) amine compounds have excellent flexibility and give elasticity (fluffiness) to clothing. ), and have completed the present invention.

すなわち本発明は、次の一般式(A)で表される化合物
の無機酸又は炭素数1〜6の有機酸の中和物又は4級化
物を柔軟基剤として含有するする水性柔軟仕上剤を提供
するものである。
That is, the present invention provides an aqueous fabric softener containing a neutralized or quaternized product of an inorganic acid or an organic acid having 1 to 6 carbon atoms of a compound represented by the following general formula (A) as a softening base. This is what we provide.

〔式中、 R’、R2:炭素数12〜22のアルキル基又はアルケ
ニル基 R3:H、メチル基又はヒドロキシエチル基#I :1
〜2 を表す。] 本発明の柔軟基剤の前駆体である第3級アミン化合物(
八)は以下のような方法により得ることができる。
[In the formula, R', R2: alkyl group or alkenyl group having 12 to 22 carbon atoms R3: H, methyl group or hydroxyethyl group #I: 1
~2 represents. ] A tertiary amine compound which is a precursor of the flexible base of the present invention (
8) can be obtained by the following method.

1)m=2の場合 N−長鎖アルキル又はアルケニルモノアミン又はN、N
−長鎖アルキル又はアルケニルメチルモノアミンとアク
リル酸の反応により得ることができる。また、R3がヒ
ドロキシエチルである化合物はN−長鎖アルキル又はア
ルケニルモノアミンとアクリル酸の反応生成物にエチレ
ンオキシドを付加することにより得ることができる。
1) When m=2, N-long chain alkyl or alkenyl monoamine or N, N
- can be obtained by reaction of long-chain alkyl or alkenylmethyl monoamines with acrylic acid. Further, a compound in which R3 is hydroxyethyl can be obtained by adding ethylene oxide to a reaction product of an N-long chain alkyl or alkenyl monoamine and acrylic acid.

2)m=1の場合 該当する長鎖アルキル又はアルケニルアミンとクロロ酢
酸又はクロロ酢酸エステルとの反応や、N−長鎖アルキ
ル又はアルケニルジェタノールアミンの脱水環化生成物
(B)と長鎖アルキル又はアルケニルアミンとの反応に
より得ることができる。
2) When m = 1, the reaction of the corresponding long-chain alkyl or alkenylamine with chloroacetic acid or chloroacetic ester, or the dehydration cyclization product (B) of N-long-chain alkyl or alkenyljetanolamine and long-chain alkyl Alternatively, it can be obtained by reaction with alkenylamine.

本発明に用いられる第3級アミン化合物(A)としては
、一般式(A)中のR3がH又はヒドロキシエチル基で
ある化合物が好ましい。
The tertiary amine compound (A) used in the present invention is preferably a compound in which R3 in the general formula (A) is H or a hydroxyethyl group.

化合物(A)から本発明の中和物を得るための酸として
は塩酸、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、マレイン酸等の炭素数6以下の有
機酸が挙げられるが、塩酸が最も安価で高性能である。
Acids for obtaining the neutralized product of the present invention from compound (A) include inorganic acids such as hydrochloric acid, nitric acid, and phosphoric acid, and organic acids having 6 or less carbon atoms such as acetic acid, lactic acid, glycolic acid, citric acid, and maleic acid. Examples include acids, but hydrochloric acid is the cheapest and has the highest performance.

また、中和工程は化合物(A)を予め中和したものを水
に分散してもよいし、酸水溶液中に化合物(A)を液状
又は固体状で投入してもよい。もちろん化合物(A)と
酸成分を同時に投入してもよい。
Further, in the neutralization step, compound (A) which has been neutralized in advance may be dispersed in water, or compound (A) may be added in liquid or solid form to an acid aqueous solution. Of course, compound (A) and the acid component may be added at the same time.

また、一般式(A)で表される化合物の4級化物はメチ
ルクロリドやジアルキル硫酸等を用いて公知の方法によ
り得ることができる。
Further, a quaternized product of the compound represented by the general formula (A) can be obtained by a known method using methyl chloride, dialkyl sulfuric acid, or the like.

本発明に係わる化合物を必須とする柔軟仕上剤を製品化
する際、製品の粘性及びハンドリング性を考慮すると本
発明に係わる化合物の総量は4〜40重量%、好ましく
は6〜30重量%、特に好ましくは10〜30重量%で
ある。
When commercializing a fabric softener that essentially includes the compound according to the present invention, the total amount of the compound according to the present invention is 4 to 40% by weight, preferably 6 to 30% by weight, especially considering the viscosity and handling properties of the product. Preferably it is 10 to 30% by weight.

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
性能う損なうことなく柔軟処理された衣料の肌ざわりを
改良できる。これらのシリコーン化合物は本発明に係わ
る化合物の総量に対し0.3〜5重量%配合されるのが
好ましい。
The softening agent of the present invention further includes dimethylpolysiloxane,
By incorporating a silicone compound such as dimethylpolysiloxane partially modified with an amino group or a polyoxyalkylene group, particularly preferably a dimethylpolysiloxane partially modified with a polyoxyalkylene group, water absorption performance can be maintained without deterioration. The feel of softened clothing can be improved. These silicone compounds are preferably blended in an amount of 0.3 to 5% by weight based on the total amount of compounds related to the present invention.

本発明の柔軟仕上剤は、従来広く用いられているジ硬化
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。
It has been found that the softening agent of the present invention has almost the same softening effect as dihardened tallow alkyldimethylammonium chloride, which has been widely used in the past, but surprisingly provides elastic softness. .

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 softener, 0.05 to 0.4% by weight of an inorganic electrolyte such as sodium chloride, calcium chloride, or magnesium chloride is added to adjust the viscosity.
It is desirable to add

本発明の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(0
1□〜24)エーテル等のノニオン界面活性剤、エタノ
ール、イソプロパツール、プロピレングリコールやエチ
レングリコール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、長鎖アルコール等を併用
してもよい。
The fabric softener of the present invention has high stability during long-term storage, but in order to stabilize it under even more severe storage conditions, polyoxyethylene (5 to 50 mol) alkyl or alkenyl (0
1□-24) A nonionic surfactant such as ether, a solvent such as ethanol, isopropanol, propylene glycol or ethylene glycol, or urea can be blended. In addition, known esters, nonionic or cationic compounds, long chain alcohols, etc. may be used in combination as flexible bases.

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
In addition, pigments or dyes can be added to improve the appearance of the product, fluorescent brighteners can be added to improve the whiteness of the finished product, and fragrances can be added to improve the taste during use and after finishing.

〔発明の効果〕〔Effect of the invention〕

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。
The fabric softener of the present invention can impart sufficient flexibility, antistatic properties, and excellent elasticity to various fibers.

〔実 施 例〕〔Example〕

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以下に示す。
Next, the present invention will be explained in detail with reference to Examples, but the present invention is not limited to these Examples. Compounds used in Examples and Comparative Examples are shown below.

表 注) 一般式(C) を以下に示す。table note) General formula (C) is shown below.

実施例1〜12 表2に示す配合の組成物について、以下の方法により柔
軟性、弾力性の評価を行った。
Examples 1 to 12 The compositions having the formulations shown in Table 2 were evaluated for flexibility and elasticity by the following methods.

く柔軟性、弾力性の評価〉 (1)  処理方法 市販の木綿タオル2kg、アクリルシャーシー1kgを
3.5°IIH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(30f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を投入し、
25°C11分間撹拌下で処理した。
Evaluation of flexibility and elasticity> (1) Processing method 2 kg of commercially available cotton towels and 1 kg of acrylic chassis were washed 5 times with commercially available detergent Attack (manufactured by Kao Corporation, registered trademark) in 3.5° IIH hard water. After washing (30f washing machine) and removing the fiber treatment agent attached to each fiber,
1.5g of the blended composition in Table 2 was added as an active ingredient,
The mixture was treated at 25° C. for 11 minutes under stirring.

なお、いずれの配合の場合もポリオキシエチレン変性ジ
メチルポリシロキサンを本発明の化合物の総量に対して
1重量%配合した。
In each case, 1% by weight of polyoxyethylene-modified dimethylpolysiloxane was blended based on the total amount of the compound of the present invention.

(2)評価方法 上記方法で処理した布を室内で風乾後、25°C165
%RHの恒温恒温室にて24時間放置した。
(2) Evaluation method After drying the cloth treated with the above method indoors at 25°C165
It was left for 24 hours in a thermostatic chamber at %RH.

これらの布について柔軟性、弾力性の評価を行った。These fabrics were evaluated for flexibility and elasticity.

柔軟性及び弾力性の評価は、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
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。
The softness and elasticity were evaluated using a pair of fabrics treated with 10 cc of a fabric softener containing 15% by weight of dihydrogenated beef tallow alkyldimethylammonium chloride as a control. The evaluation is expressed as follows.

+2;対照より柔らかい又は弾力性が高い+l;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;対照がやや柔らかい又は対照より弾力性がやや低
い −2;対照が柔らかい又は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、柔軟性と弾力性の両者を満足する効果が得られる。
+2; Softer or more elastic than the control +l; Slightly softer or more elastic than the control 0; Same as the control -1; Control is slightly softer or slightly less elastic than the control -2; Control is soft or the control As shown in Table 2, which has lower elasticity, by using the compound of the present invention, an effect that satisfies both flexibility and elasticity can be obtained.

表 柔軟性、 弾力性 実施例13〜15、比較例3,4 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。
Surface Softness, Elasticity Examples 13 to 15, Comparative Examples 3 and 4 To evaluate the elasticity of the compositions shown in Table 3, the stacking height of cotton towels was measured.

〈弾力性の評価〉 実施例1〜12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/cd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。
<Evaluation of elasticity> Cotton towels treated in the same manner as in Examples 1 to 12 were folded into 8 and stacked in 3 layers, and after pressurizing at a pressure of 5 g/cd for 5 minutes, the pressure was removed and the height of the towel was adjusted. was measured. The higher the height of the towel, the better the elasticity.

手続補正書 (自発) 平成3年11月27日 事件の表示 特願平1−221746号 発明の名称 柔軟仕上剤 補正をする者 事件との関係  特許出願人 花  王  株  式  会  社Procedural amendment (spontaneous) November 27, 1991 Display of incidents Patent Application No. 1-221746 name of invention Softener person who makes corrections Relationship to the case Patent applicant Hana Wang Stock Company

Claims (1)

【特許請求の範囲】 1 次の一般式(A)で表される化合物の無機酸又は炭
素数1〜6の有機酸の中和物又は4級化物を柔軟基剤と
して含有する水性柔軟仕上剤。 ▲数式、化学式、表等があります▼(A) 〔式中、 R^1、R^2:炭素数12〜22のアルキル基又はア
ルケニル基 R^3:H、メチル基又はヒドロキシエチル基m:1〜
2を表す。〕 2 一般式(A)中のR^3がH又はヒドロキシエチル
基である化合物の無機酸の中和物を柔軟基剤として含有
する請求項1記載の水性柔軟仕上剤。
[Scope of Claims] 1. An aqueous fabric softener containing a neutralized or quaternized product of an inorganic acid or an organic acid having 1 to 6 carbon atoms of a compound represented by the following general formula (A) as a softening base. . ▲There are mathematical formulas, chemical formulas, tables, etc.▼(A) [In the formula, R^1, R^2: Alkyl group or alkenyl group having 12 to 22 carbon atoms R^3: H, methyl group or hydroxyethyl group m: 1~
Represents 2. 2. The aqueous fabric softener according to claim 1, which contains as a softening base a neutralized product of an inorganic acid of a compound in which R^3 in the general formula (A) is H or a hydroxyethyl group.
JP22174690A 1990-08-22 1990-08-22 Softening agent Expired - Fee Related JPH0726325B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP22174690A JPH0726325B2 (en) 1990-08-22 1990-08-22 Softening agent

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP22174690A JPH0726325B2 (en) 1990-08-22 1990-08-22 Softening agent

Publications (2)

Publication Number Publication Date
JPH04108177A true JPH04108177A (en) 1992-04-09
JPH0726325B2 JPH0726325B2 (en) 1995-03-22

Family

ID=16771577

Family Applications (1)

Application Number Title Priority Date Filing Date
JP22174690A Expired - Fee Related JPH0726325B2 (en) 1990-08-22 1990-08-22 Softening agent

Country Status (1)

Country Link
JP (1) JPH0726325B2 (en)

Also Published As

Publication number Publication date
JPH0726325B2 (en) 1995-03-22

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