JPH0765267B2 - Softening agent - Google Patents
Softening agentInfo
- Publication number
- JPH0765267B2 JPH0765267B2 JP2221741A JP22174190A JPH0765267B2 JP H0765267 B2 JPH0765267 B2 JP H0765267B2 JP 2221741 A JP2221741 A JP 2221741A JP 22174190 A JP22174190 A JP 22174190A JP H0765267 B2 JPH0765267 B2 JP H0765267B2
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- softening
- acid
- alkyl group
- present
- 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
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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。TECHNICAL FIELD The present invention relates to a softening finish, and more specifically, a liquid softening finish that can impart excellent flexibility and elasticity (puffiness) to various fibers. It is about.
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。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。Currently, most of the commercially available products as household softening agents are quaternary ammonium salts having two long-chain alkyl groups in one molecule, as typified by di (hardened tallow alkyl) dimethylammonium chloride. It is a composition containing the main component. 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 quaternary ammonium salt has a remarkable softening effect on cotton, it is hard to say that it is sufficiently effective on synthetic fibers such as acrylic, polyester and polyamide fibers. However, if the treatment is performed at a higher concentration, the elasticity of the clothing may be deteriorated 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、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。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。
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
剤等の添加剤を配合し、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。Furthermore, since the quaternary ammonium salt has a strong hydrophobicity, when it is poured into the rinse water when the stirring force is weak, the dispersibility in water is poor, and therefore the clothing may be uneven. Further, particularly when it is stored for a long period of time at a low temperature, it may thicken, form a gel, or separate.
In addition to the above quaternary ammonium salt, commercially available softeners are compounded with additives such as polyoxyethylene-based nonionic surfactants, electrolytes and solvents to improve dispersibility in water and long-term storage stability. However, the effect is 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。Further, conventionally, liquid softening finishes having various amines as softening bases have been known. For example, JP-A-52-59796 discloses a composition for imparting flexibility to a fiber containing a long-chain alkylamine such as methyldi (cured tallow alkyl) amine, and JP-A-58-6070 discloses a composition. A fiber material finishing agent which imparts smoothness and a comfortable touch to a fiber containing an acylated alkanolamine, a water-soluble quaternary ammonium salt and a fatty acid ester is disclosed in JP-A-61-167083. A softening agent having a good dispersibility containing a condensation reaction product of a higher fatty acid and a hydroxy lower alkyl polyamine and an alkylamine polyglycol ether is disclosed in JP-A-61-275474. A stable aqueous dispersion for treating textiles containing an acid is disclosed in JP-A-64-85368 in which a dilong-chain alkylamine-anionic surfactant ion-pair complex, a non-silyl group. A softening composition containing corn wax and a liquid carrier is disclosed in JP-A-2-6662 in which a fabric conditioning composition containing an amine such as a condensate of a hydroxy lower alkylalkylene diamine and a higher fatty acid and an amphoteric fabric conditioning agent is disclosed. Kahei 2-14076 discloses a flexible resin containing a dilong-chain alkylamine-polyfunctional carboxylic acid complex,
Fabric conditioning compositions that impart antistatic properties are described.
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 condition-controlling composition containing a mono- or di-long-chain alkylalkylenediamine static inhibitor 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, the softening agents containing these amines are relatively better in dispersibility and storage stability than the softening agents containing the quaternary ammonium salt, but the softening performance is still insufficient.
〔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
又は第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 earnest studies on a softener containing an amine, the present inventors have found that a neutralized product or a quaternized product of a special (di-long-chain type) amine compound provides flexibility. They have found that they are excellent and can impart elasticity (puffiness) to clothes, and have completed the present invention.
すなわち本発明は、下記の式（Ａ）で表される第３級ア
ミン（Ａ）化合物の無機酸又は炭素数１〜６の有機酸の
中和物、或いは下記の式（Ｂ）で表される第３アミン化
合物（Ｂ）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
を提供するものである。That is, the present invention is represented by a neutralized product of an inorganic acid or an organic acid having 1 to 6 carbon atoms of a tertiary amine (A) compound represented by the following formula (A), or represented by the following formula (B). An aqueous softening finish containing a neutralized product or a quaternized product of an inorganic acid or an organic acid having 1 to 6 carbon atoms as the tertiary amine compound (B).
〔式中、R1は炭素数１〜４のアルキル基、Ｒは炭素数15
〜21のアルキル基又はアルケニル基を表す。〕 〔式中、R2は炭素数１〜４のアルキル基又は炭素数２〜
３のヒドロキシアルキル基、Ｒは炭素数15〜21のアルキ
ル基又はアルケニル基を表す。〕 本発明の柔軟基剤の前駆体である第３級アミン化合物
（Ａ）はメチルアミンやエチルアミン等の低級アルキル
アミンをシアノエチル化、水添反応することにより得ら
れる下式の化合物等を炭素数16〜22の脂肪酸によりアミ
ド化して得ることができる。 [In the formula, R 1 is an alkyl group having 1 to 4 carbon atoms, and R is 15 carbon atoms.
~ 21 represents an alkyl group or an alkenyl group. ] [In the formula, R 2 is an alkyl group having 1 to 4 carbon atoms or 2 to 2 carbon atoms.
3 is a hydroxyalkyl group, and R is an alkyl group or alkenyl group having 15 to 21 carbon atoms. The tertiary amine compound (A), which is a precursor of the flexible base of the present invention, has a carbon number of a compound of the following formula obtained by cyanoethylation of a lower alkylamine such as methylamine or ethylamine and hydrogenation reaction. It can be obtained by amidation with 16 to 22 fatty acids.
〔式中、R1は炭素数１〜４のアルキル基を表す。〕 また、本発明の柔軟基剤の前駆体である第３級アミン化
合物（Ｂ）はメチルアミンやエチルアミン等の低級アル
キルアミンやモノアルカノールアミンと（メタ）アクリ
ル酸とのマイケル付加反応により得られる下式の化合物
等と炭素数16〜22の脂肪族アミンをアミド化反応して得
ることができる。 [In the formula, R 1 represents an alkyl group having 1 to 4 carbon atoms. The tertiary amine compound (B), which is the precursor of the soft base of the present invention, is obtained by the Michael addition reaction of a lower alkylamine such as methylamine or ethylamine or a monoalkanolamine with (meth) acrylic acid. It can be obtained by subjecting a compound of the following formula and the like and an aliphatic amine having 16 to 22 carbon atoms to an amidation reaction.
〔式中、R2は炭素数１〜４のアルキル基又は炭素数２〜
３のヒドロキシアルキル基〕 本発明の柔軟基剤は上記の化合物（Ａ）、（Ｂ）を中和
又は（Ｂ）を４級化して得られる。化合物（Ａ）、
（Ｂ）の中和に用いられる酸としては塩酸、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。また、化合
物（Ｂ）の４級化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行なうことができる。 [In the formula, R 2 is an alkyl group having 1 to 4 carbon atoms or 2 to 2 carbon atoms.
Hydroxyalkyl Group 3] The soft base of the present invention is obtained by neutralizing the above compounds (A) and (B) or quaternizing the above (B). Compound (A),
Examples of the acid used for neutralizing (B) include inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, lactic acid, glycolic acid,
Organic acids having 6 or less carbon atoms such as citric acid and maleic acid can be mentioned, but hydrochloric acid is the cheapest and has the highest performance. Further, the quaternization of the compound (B) can be carried out 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。Considering the viscosity and handling property of the product when commercializing a softening finish containing the compound of the present invention as an essential component, the total amount of the compound of the present invention is 4 to 40% by weight, preferably 6 to 30% by weight, particularly It is preferably 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 comprises dimethylpolysiloxane,
A silicone compound such as dimethylpolysiloxane partially modified with an amino group or a polyoxyalkylene group, and particularly preferably a dimethylpolysiloxane partially modified with a polyoxyalkylene group is blended without impairing water absorption performance. The texture of softly treated clothing can be improved. These silicone compounds are preferably added in an amount of 0.3 to 5% by weight based on the total amount of the compounds according 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。The softening agent of the present invention has almost the same softening effect as compared with the conventionally widely used di-hardened beef tallow alkyldimethylammonium chloride, but it was surprisingly found that elastic softness is obtained. .
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
の調整のための塩化ナトリウム、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, 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 for adjusting the viscosity.
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（Ｃ
12〜24）エーテル等のノニオン界面活性剤、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。なお、このような柔軟基
剤を併用する場合、本発明に係わる化合物は柔軟基剤総
量中に50重量％より多く配合するのが好ましい。The 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
12-24 ) A nonionic surfactant such as ether, a solvent such as propylene glycol or ethylene glycol, or urea can be added. Also, known esters, nonionic or cationic compounds, long-chain alcohols and the like may be used in combination as a soft base. When such a soft base is used in combination, the compound of the present invention is preferably added in an amount of more than 50% by weight based on the total amount of the soft base.
また、製品の外観のための顔料又は染料を、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。It is also possible to incorporate pigments or dyes for the appearance of the product, fluorescent brighteners for the whiteness of the finish, and fragrances for a good taste when used and after the finish.
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 softening agent of the present invention can impart sufficient flexibility and antistatic properties to various fibers and impart excellent elasticity.
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.
実施例及び比較例で用いた化合物を以下に示す。The compounds used in Examples and Comparative Examples are 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.
＜柔軟性、弾力性の評価＞ （１） 処理方法 市販の木綿タオル2kg、アクリルジャージー1kgを3.5゜D
H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℃、１分間攪拌下
で処理した。<Evaluation of flexibility and elasticity> (1) Treatment method Commercially available cotton towel 2kg, acrylic jersey 1kg 3.5D
After washing with a commercially available detergent attack (Kao Co., Ltd., registered trademark) 5 times repeatedly with H hard water (30 washing machines) to remove the fiber treatment agent attached to each fiber, the compounding composition of Table 2 is effective. 1.5 g was added as a component and treated at 25 ° C. for 1 minute 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（ａ）成分及び（ｂ）成分の総
量に対して１重量％配合した。In each case, 1% by weight of polyoxyethylene-modified dimethylpolysiloxane was added to the total amount of the components (a) and (b).
（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。(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.
これらの布について柔軟性、弾力性の評価を行った。The softness and elasticity of these cloths were evaluated.
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 of the softener consisted of 15% by weight of dihydrogenated tallow alkyldimethylammonium chloride.
A pair of comparisons was made using the 10 cc treated fabric 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 ＋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 +1; slightly softer or more elastic than the control 0; same as the control -1; slightly softer than the control or slightly less elastic than the control -2; softer or the control Less Elasticity As shown in Table 2, by using the compound of the present invention, the effect of satisfying both flexibility and elasticity can be obtained.
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。 Examples 13 to 15 and Comparative Examples 3 and 4 In order to evaluate the elasticity of the compositions having the formulations shown in Table 3, the piled 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/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。<Evaluation of Elasticity> The cotton towels treated in the same manner as in Examples 1 to 12 were folded in eight, and three sheets were piled up and piled up, and after applying a pressure of 5 g / cm 2 for 5 minutes, the pressure was removed and the towel height was increased. Was measured. The higher the towel height, the better the elasticity.
Claims (2)
合物（Ａ）の無機酸又は炭素数１〜６の有機酸の中和物
を柔軟基剤として含有する水性柔軟仕上剤。 〔式中、R1は炭素数１〜４のアルキル基、Ｒは炭素数15
〜21のアルキル基又はアルケニル基を表す。〕1. An aqueous softening finish containing a neutralized product of an inorganic acid of a tertiary amine compound (A) represented by the following formula (A) or an organic acid having 1 to 6 carbon atoms as a softening base. . [In the formula, R 1 is an alkyl group having 1 to 4 carbon atoms, and R is 15 carbon atoms.
~ 21 represents an alkyl group or an alkenyl group. ]
合物（Ｂ）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。 〔式中、R2は炭素数１〜４のアルキル基又は炭素数２〜
３のヒドロキシアルキル基、Ｒは炭素数15〜21のアルキ
ル基又はアルケニル基を表す。〕2. A neutralized product or quaternized product of an inorganic acid or an organic acid having 1 to 6 carbon atoms of a tertiary amine compound (B) represented by the following formula (B) is contained as a flexible base. Water-based softening agent. [In the formula, R 2 is an alkyl group having 1 to 4 carbon atoms or 2 to 2 carbon atoms.
3 is a hydroxyalkyl group, and R is an alkyl group or alkenyl group having 15 to 21 carbon atoms. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2221741A JPH0765267B2 (en) | 1990-08-22 | 1990-08-22 | Softening agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2221741A JPH0765267B2 (en) | 1990-08-22 | 1990-08-22 | Softening agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04108173A JPH04108173A (en) | 1992-04-09 |
| JPH0765267B2 true JPH0765267B2 (en) | 1995-07-12 |
Family
ID=16771504
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2221741A Expired - Fee Related JPH0765267B2 (en) | 1990-08-22 | 1990-08-22 | Softening agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0765267B2 (en) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| Publication number | Priority date | Publication date | Assignee | Title |
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| ZA907746B (en) * | 1989-10-16 | 1992-05-27 | Colgate Palmolive Co | New softening compositions and methods for making and using same |
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1990
- 1990-08-22 JP JP2221741A patent/JPH0765267B2/en not_active Expired - Fee Related
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| Publication number | Publication date |
|---|---|
| JPH04108173A (en) | 1992-04-09 |
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