JPS63260991A - Softening finish agent - Google Patents
Softening finish agentInfo
- Publication number
- JPS63260991A JPS63260991A JP9713587A JP9713587A JPS63260991A JP S63260991 A JPS63260991 A JP S63260991A JP 9713587 A JP9713587 A JP 9713587A JP 9713587 A JP9713587 A JP 9713587A JP S63260991 A JPS63260991 A JP S63260991A
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- group
- quaternary ammonium
- alkyl group
- asymmetric
- 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.)
- Pending
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 18
- 239000002979 fabric softener Substances 0.000 claims description 13
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
- 239000004973 liquid crystal related substance Substances 0.000 claims description 7
- 239000002245 particle Substances 0.000 claims description 7
- 230000007704 transition Effects 0.000 claims description 7
- 239000004902 Softening Agent Substances 0.000 claims description 6
- 238000009826 distribution Methods 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000002585 base Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- -1 alkyl quaternary ammonium salts Chemical class 0.000 description 8
- 239000000835 fiber Substances 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 7
- 125000002091 cationic group Chemical group 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000003760 tallow Substances 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 150000003335 secondary amines Chemical class 0.000 description 5
- 150000003512 tertiary amines Chemical class 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 2
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical class C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000005956 quaternization reaction Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical class CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000004664 distearyldimethylammonium chloride (DHTDMAC) Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
Landscapes
- Detergent Compositions (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
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、更に詳細には、各種繊維に対して
優れた柔軟性、帯電防止性及び吸水性を付与することの
できる柔軟仕上剤に関する。[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to a fabric softener, and more particularly, a fabric softener that can impart excellent flexibility, antistatic properties, and water absorption properties to various fibers. Regarding drugs.
衣料は、着用及び洗濯を繰り返し行う間に繊維処理剤が
洗い落とされたり、あるいは繊維自体の劣化により硬く
なったりして好ましからざる風合を生ずる。そのため、
近年、多くの家庭において、繊維に柔軟性、帯電防止性
を付与することができる柔軟仕上剤が多用されている。When clothing is repeatedly worn and washed, the fiber treatment agent may be washed off, or the fibers themselves may become hard due to deterioration, resulting in an undesirable feel. Therefore,
In recent years, fabric softeners that can impart flexibility and antistatic properties to fibers have been widely used in many households.
現在、家庭用柔軟仕上剤として市販されているものは、
その殆どが、−分子中に１〜２個の長鎖アルキル基を有
するカチオン性活性剤、就中ゾ（硬化牛脂アルキル）ジ
メチルアンモニウム塩を主成分とするものである。Currently, the commercially available household fabric softeners are:
Most of them are based on cationic surfactants having one or two long-chain alkyl groups in the molecule, especially zo(hardened tallow alkyl) dimethylammonium salts.
この第四級アンモニウム塩は、各種繊維に対して少量で
良好な柔軟効果及び帯電防止効果を付与することができ
る。そして、これによる柔軟効果は、繊維表面に吸着し
た基剤分子中の親油性部位による潤滑効果によって繊維
表面の摩擦係数が下がって発現するものであるから、優
れた柔軟効果を奏するためには、親油的な性質が不可欠
であると考えられる。This quaternary ammonium salt can impart good softening and antistatic effects to various fibers in small amounts. The resulting flexibility effect is produced by lowering the friction coefficient of the fiber surface due to the lubricating effect of the lipophilic moieties in the base molecules adsorbed on the fiber surface, so in order to achieve an excellent flexibility effect, Lipophilic properties are considered essential.
ところが、この親油的性質は、処理した衣料を撥水化し
、吸水性を低下させるという欠点があり、特に柔軟仕上
剤濃度が高い場合には顕著な吸水性の低下がみられる。However, this lipophilic property has the disadvantage that it makes treated clothing water repellent and reduces its water absorbency, particularly when the concentration of fabric softener is high.
斯かる観点から、吸水性を向上させるための検討がなさ
れており、分岐アルキル型第四級アンモニウム塩（米国
特許第３，３７７．３８２号、同λ３９５，１００号）
、オレイン酸から誘導されるイミダゾリニウム化合物〔
シャーナル・オプーアメリカン・オイル・ケミカル・ソ
サイエティー（ＪＡＯＣ８） 、 ６１ 、３６７ （
１９８４） ３等が報告されている。From this point of view, studies have been made to improve water absorption, and branched alkyl quaternary ammonium salts (U.S. Pat. No. 3,377.382 and U.S. Pat. No. 395,100) have been studied.
, imidazolinium compounds derived from oleic acid [
Sharnall Opu American Oil and Chemical Society (JAOC8), 61, 367 (
1984) 3rd grade has been reported.
これらの化合物は、吸水性能においては充分な効果を有
するが、その反面柔軟効果が低く、前述のゾ（硬化牛脂
アルキル）ジメチル第四級アンモニウム塩のそれに比較
し明らかに劣っている。従って、当該イミダゾリニウム
化合物は、柔軟効果を補うためて、通常ジステアリルジ
メチルアンモニウムクロライド、硬化牛脂脂肪酸から誘
導されるイミダゾリニウム化合物などを併用しているが
、この場合には一足な吸水性は得られない。また、α位
分岐アルキル型第四級アンモニウム塩やβ位分岐アルキ
ル型第四級アンモニウム塩においては、直鎖アルキル型
第四級アンモニウム塩との併用によりその解決を図って
いる〔特開昭４９−６９９９８号、同５０−５３６９４
号、同５４−１２２２０７号、同５８−１４４１７４号
、米国特許第３，８９４６６９号、***特許第４６２５
，９４５号〕が、いずれも柔軟効果が劣り、満足し得る
ものは提供されていない。These compounds have a sufficient effect on water absorption performance, but on the other hand, have a low softening effect, which is clearly inferior to that of the above-mentioned zo(hardened tallow alkyl) dimethyl quaternary ammonium salt. Therefore, in order to supplement the softening effect, the imidazolinium compound is usually used in combination with distearyldimethylammonium chloride, an imidazolinium compound derived from hardened tallow fatty acid, etc. cannot be obtained. Furthermore, in the case of α-position branched alkyl type quaternary ammonium salts and β-position branched alkyl type quaternary ammonium salts, we are trying to solve the problem by using them in combination with straight-chain alkyl type quaternary ammonium salts [JP-A-49-1994] -69998, 50-53694
No. 54-122207, No. 58-144174, U.S. Patent No. 3,894669, West German Patent No. 4625
, No. 945], but all of them have inferior softening effects, and none have been provided that are satisfactory.
本発明者らは、かかる実状において、充分な柔軟性能を
有し、かつ処理した衣料の吸水性を損なうことのない柔
軟仕上剤を開発すべく鋭意検討を重ねた結果、炭素数の
異なる２つの長鎖アルキル基または長鎖β−ヒドロキシ
アルキル基を有し、しかもその少なくとも一方が分岐鎖
のものである非対称二鎖型第四級アンモニウム塩が上記
目的にあった柔軟基剤であることを見出し、本発明を完
成した。Under these circumstances, the inventors of the present invention have conducted intensive studies to develop a fabric softener that has sufficient flexibility and does not impair the water absorbency of treated clothing. It has been discovered that an asymmetric two-chain quaternary ammonium salt having a long-chain alkyl group or a long-chain β-hydroxyalkyl group, at least one of which is branched, is a flexible base material suitable for the above purpose. , completed the invention.
すなわち、本発明は、一般式（Ｉ）
〔式中、Ｒ１は炭素数１０〜２４の直鎖もしくは分岐鎖
のアルキル基またはβ−ヒドロキシアルキル基、Ｒ１は
炭素数１０〜２４の分岐鎖のアルギル基またはβ−ヒド
ロキシアルキル基で、Ｒ１とＲ，は３個以上の炭素数の
差を有するものとする。Ｒ３及びＲ４は炭素数１〜３の
アルキル基もしくハヒドロキシアルキル基、ペンシル基
または−（Ｃ２■（４０）ｎＨ（但・し、ｎは２〜３を
示す）を示し、Ｘはノ１０ダン原子または炭素数１〜３
のアルキル基を有するモノアルキル硫酸塩基を示す〕
で表わされる非対称二鎖ｍ第四級アンモニウム塩を含有
する柔軟仕上剤を提供するものである。That is, the present invention provides general formula (I) [wherein R1 is a linear or branched alkyl group having 10 to 24 carbon atoms or a β-hydroxyalkyl group, and R1 is a branched argyl group having 10 to 24 carbon atoms] group or β-hydroxyalkyl group, and R1 and R have a difference in the number of carbon atoms of 3 or more. R3 and R4 represent an alkyl group having 1 to 3 carbon atoms, a hydroxyalkyl group, a pencil group, or -(C2(40)nH (wherein, n represents 2 to 3), and X is Dan atom or carbon number 1-3
The present invention provides a fabric softener containing an asymmetric two-chain m quaternary ammonium salt represented by:
本発明に用いる非対称二鎖型第四級アンモニウム塩（Ｉ
）は、対応する第二級アミンまたは第三級アミンの四級
化反応によって得ることができる。Asymmetric two-chain quaternary ammonium salt (I
) can be obtained by quaternization reaction of the corresponding secondary or tertiary amine.
原料となる第二級アミンは、例えば牛脂脂肪酸より誘導
した第一級アミンと長鎖分岐アルコールとを、水素化触
媒の存在下、水素雰囲気（１〜１０気圧）中で反応させ
る方法等で得られる。また第三級アミンは、第二級アミ
ンを等量のアルカリの存在下、等量の低級アルキルハラ
イドと反応させる方法等で得られる。The secondary amine used as a raw material can be obtained, for example, by a method in which a primary amine derived from tallow fatty acid and a long chain branched alcohol are reacted in a hydrogen atmosphere (1 to 10 atm) in the presence of a hydrogenation catalyst. It will be done. The tertiary amine can be obtained by reacting a secondary amine with an equal amount of lower alkyl halide in the presence of an equal amount of alkali.
第二級アミンまたは第三級アミンは、含有する低沸点物
を減圧下、初留分として留去して精製したものを用いて
も良く、また反応物そのものを用いてもよい。The secondary amine or tertiary amine may be purified by distilling off the low boiling point substances contained therein under reduced pressure as an initial fraction, or the reactant itself may be used.
このような方法によって得られた第二級または第三級ア
ミンの四級化反応は、例えば四級化剤としてメチルクロ
ライドを用いる場合には、オートクレーブ中で溶媒とし
て水、イソゾロビルアルコールを、アルカリとしてソー
ダ灰または苛性ソーダを用い、メチルクロライドを導入
して１００〜１１０℃で数時間反応させることにより行
なわれる。反応後、副生したＮａＣｌをろ別すれば、本
発明に用いる非対称二鎖型第四級アンモニウムクロライ
ド（１）が水、イソゾロビルアルコールの溶液として得
られる。The quaternization reaction of a secondary or tertiary amine obtained by such a method can be carried out by using water, isozorobyl alcohol as a solvent in an autoclave, for example, when using methyl chloride as a quaternizing agent. The reaction is carried out by using soda ash or caustic soda as an alkali, introducing methyl chloride, and reacting at 100 to 110°C for several hours. After the reaction, by-produced NaCl is filtered off to obtain the asymmetric two-chain quaternary ammonium chloride (1) used in the present invention as a solution of water and isozorobyl alcohol.
本発明に用いる非対称二鎖型第四級アンモニウム塩（Ｉ
）は、ダル液晶転移温度が３０℃以下、特に０〜１５℃
であるのが好ましい。非対称二鎖型第四級アンモニウム
塩（１）は、その原料の炭素鎖長分布あるいは製造方法
などにより混合物として得られる場合があるが、このよ
うな場合でも生成物のダル液晶転移温度が上記の範囲で
あれば好ましく使用できる。Asymmetric two-chain quaternary ammonium salt (I
) has a dull liquid crystal transition temperature of 30℃ or less, especially 0 to 15℃
It is preferable that The asymmetric two-chain quaternary ammonium salt (1) may be obtained as a mixture depending on the carbon chain length distribution of its raw materials or the manufacturing method, but even in such cases, the dull liquid crystal transition temperature of the product is within the above range. It can be preferably used within this range.
本発明の柔軟仕上剤は、その目的に応じて、液体状、粉
末状、スゾレー（エアゾール）、更に布、不織布、ペー
、９−タオル等に含浸させたシート等の種々の形態とす
ることができる。斯かる柔軟仕上剤中の非対称二鎖型第
四級アンモニウム塩（Ｉ）の配合量はその形態によって
も異なるが、非対称二鎖型第四級アンモニウム塩を水中
に分散させた液体状組成物の場合には３〜２０重量％（
以下、％で示す）が゛好ましい。この場合、分散粒子の
粒度分布は、コールタ−カウンター（’ｆ’Ａ ＩＩ型
、アノ９−チャーチューブ５０μｍ、Ｃ０ＵＬＴＥＲＥ
亘Ｔ朗ＮＩＣ８社製）で測定して５μｍ以下のものが９
０％以上存在しているのが好ましく、この粒度分布を外
れると柔軟性能が低下する。The fabric softener of the present invention can be in various forms depending on the purpose, such as liquid, powder, sosolet (aerosol), and a sheet impregnated with cloth, nonwoven fabric, paper, towel, etc. can. The blending amount of the asymmetric two-chain quaternary ammonium salt (I) in such a softening agent varies depending on its form, but the amount of the asymmetric two-chain quaternary ammonium salt (I) dispersed in water is In some cases, 3 to 20% by weight (
(hereinafter expressed in %) is preferred. In this case, the particle size distribution of the dispersed particles was determined using a Coulter counter ('f'A type II, Ano9-char tube 50 μm, COULTERE
(Manufactured by Wataru T-ro NIC8), 9 were 5 μm or less.
It is preferable that the content is 0% or more, and if the particle size distribution is outside this range, the flexibility will decrease.
本発明の柔軟仕上剤には、一般式（Ｉ）で表わされる非
対称二鎖型第四級アンモニウム塩と共に、公知のカチオ
ン柔軟基剤を必要に応じて本願発明の効果を阻害しない
範囲で併用することができる。このようなカチオン柔軟
基剤としては、例えば、次のものが挙げられる。In the softening agent of the present invention, a known cationic softening base is used in combination with the asymmetric two-chain quaternary ammonium salt represented by general formula (I), as necessary, within a range that does not impede the effects of the present invention. be able to. Examples of such cationic flexible bases include the following.
（イ）ゾ硬化牛脂アルキル第四級アンモニウム塩などの
対称二鎖型第四級アンモニウム塩（ロ）下記（１）〜（
４）式で表わされる炭素数１０〜２４のアルキル基、ア
ルケニル基またはβ−ヒドロキシアルキル基を分子内に
１または２個有するアミドアンモニウム塩
〔式中、Ｒ７及びＲＩＩはそれぞれ炭素数１０〜２４の
アルキル基、アルケニル基またはβ−ヒドロキシアルキ
ル基、Ｒ５、Ｒ６、Ｒ９及びＲＩＯはそれぞれ水素原子
、炭素原子数１〜３のアルキル基４しくはヒドロキシア
ルキル基、ベンシル基または−（ｃ２Ｈ４ｏ）、Ｊ（（
Ｐは１〜３の数を示す）を示し、ｑは２または３であり
、Ｘはハロゲンまたは炭素数１〜３のアルキル基を有す
るモノアルキル硫酸塩基を示す。〕（ハ） 下記（５）
式で表わされるイミダゾリニウム塩
〔式中、Ｒ１１及びＲ１２は炭素数１０〜２４のアルキ
ル基、アルケニル基またはβ−ヒドロキシアルキル基、
Ｒ１３は炭素数１〜３のアルキル基もしくはヒドロキシ
アルキル基、ペンシル基または−（Ｃ，ｋＬ４０）ｋＨ
，（Ｃ３Ｈ６０）ＩＨ（ｋ％ ｌは各々１〜３の数を
示す）を示し、Ｘはハロダンまたは炭素数１〜３のアル
キル基を有するモノアルキル硫酸塩基を示す。〕
しかしながら、これらのカチオン柔軟基剤の配合量が多
すぎると本発明の目的である優れた柔軟性と吸水性を損
なうことがある。従ってこれらの公知のカチオン柔軟基
剤を併用する場合には、非対称二鎖型第四級アンモニウ
ム塩（Ｉ）との混合系のゲル液晶転移温度が３０Ｃｅ越
えないように、公知のカチオン柔軟基剤の配合量を調節
することが必要である。(a) Symmetrical two-chain quaternary ammonium salts such as zocured beef tallow alkyl quaternary ammonium salts (b) The following (1) to (
4) Amide ammonium salt having one or two alkyl groups, alkenyl groups, or β-hydroxyalkyl groups having 10 to 24 carbon atoms in the molecule represented by the formula [wherein R7 and RII each have 10 to 24 carbon atoms] Alkyl group, alkenyl group or β-hydroxyalkyl group, R5, R6, R9 and RIO are each hydrogen atom, alkyl group having 1 to 3 carbon atoms or hydroxyalkyl group, benzyl group or -(c2H4o), J( (
P represents a number from 1 to 3), q is 2 or 3, and X represents a halogen or a monoalkyl sulfate group having an alkyl group having 1 to 3 carbon atoms. ] (c) Below (5)
An imidazolinium salt represented by the formula [wherein R11 and R12 are an alkyl group having 10 to 24 carbon atoms, an alkenyl group or a β-hydroxyalkyl group,
R13 is an alkyl group having 1 to 3 carbon atoms, a hydroxyalkyl group, a pencil group, or -(C,kL40)kH
, (C3H60)IH (k% l each represents a number from 1 to 3), and X represents halodane or a monoalkyl sulfate group having an alkyl group having 1 to 3 carbon atoms. ] However, if the amount of these cationic softening bases is too large, the excellent flexibility and water absorbency, which are the objectives of the present invention, may be impaired. Therefore, when using these known cationic flexible bases in combination, use the known cationic flexible bases so that the gel-liquid crystal transition temperature of the mixed system with the asymmetric two-chain quaternary ammonium salt (I) does not exceed 30Ce. It is necessary to adjust the blending amount.
本発明の柔軟仕上剤には、上記カチオン柔軟基剤の他に
その目的とする形態機能に応じて例えば次の化合物を配
合することができる。In addition to the above-mentioned cationic softening base, the softening agent of the present invention may contain, for example, the following compounds depending on the intended form and function.
（ａ） アミン
Ｒ，４Ｃ−Ｎ−Ｃ，Ｈ４Ｎｆ−１ｃＯＲ，５〔式中、Ｒ
１４は炭素数８〜２４の飽和もしくは不飽和の直鎖もし
くは分岐のアルキル基または炭素数８〜２４の２級アル
カノール基、Ｒ１６は炭素数１〜３のアルキル基もしく
はヒドロキシアルキル基または−（ＣＨ２ＣＨ，０）
ｔＨ（ｔ ｕ１〜１０の数を示す） 、Ｒ１７％ Ｒｌ
ｍは各々炭素数１〜３のフルキレン基−ｉ２ タＢ −
（ＣＨ，ＣＨ，Ｏ） ｕＨ（Ｕは１〜１０の数を示す）
、ｒ及び３は１〜１０の数を示し、Ｒ１５はＲ１４また
はＲＩＩＳと同じ基を示す。〕
（ｂ） 非イオン活性剤
Ｒ，４−（ＯＣＨ，Ｃｋ１２）ｘｌ−０ＨＨＯ−（ＣＨ
２ＣＨ２０） ｘｌ −（ＣＨ２０ＨＯ） ）’ｔ−（
Ｃ）Ｉ２ＣＨ，Ｏ） ｚｌ −ＨるＨ３
０ （Ｃ）Ｉ、ＣＨ２０） ｘ、−Ｈ
ＣＨ，０Ｈ
ＣＨ！０ＣＯＲ１４
ＣＨＯＣＯＲｌ。(a) Amine R,4C-N-C,H4Nf-1cOR,5 [wherein, R
14 is a saturated or unsaturated linear or branched alkyl group having 8 to 24 carbon atoms or a secondary alkanol group having 8 to 24 carbon atoms, R16 is an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group, or -(CH2CH ,0)
tH (indicates the number of tu1 to 10), R17% Rl
m is a fullkylene group having 1 to 3 carbon atoms -i2 taB -
(CH, CH, O) uH (U indicates a number from 1 to 10)
, r and 3 represent numbers from 1 to 10, and R15 represents the same group as R14 or RIIS. ] (b) Nonionic activator R,4-(OCH,Ck12)xl-0HHO-(CH
2CH20) xl -(CH20HO) )'t-(
C)I2CH,O) zl -HruH3 0 (C)I,CH20) x, -H CH,0H CH! 0COR14 CHOCORl.
ＣＨ，０Ｈ
Ｒ１４ＣＯＯ（ＣＨ，ＣＨ２０） Ｘｏ−Ｃｏ −Ｒ１
５Ｒ，４ＣＯＯ（ＣＨ２ＣＨ，０） ｘｏ−Ｈ〔式中、
ｘｏ＃′ｉ１〜１０ｏの数、ｘｌ、）’１％ｚｌはＸｌ
＋７ｔ ＋Ｚｓ ＝ １００を満足する数、Ｉ２、ｙ！
、ｚ２は各々θ〜１００の数を示す。Ｒ１４及びＲ１５
は前記と同じ意味を有する。〕
（ｅ） 脂肪酸
Ｒ１，Ｃ００Ｈ
（式中、Ｒ１４は前記と同じ意味を有する）（ｄ）
アニオン界面活性剤
脂肪ｅ［アルキルベンゼンスルホン酸ナトリウム、アル
キル硫酸エステル塩、アルキルナフタレンスルホン酸塩
、アルキルリン酸塩など
（ｅ） 両性界面活性剤
アルキルジメチルアミノ酢酸ベタイン、アルキルカルボ
キシメチルヒドロキシエチルイミダゾリニウムペタイン
など
（ｆ） 水溶性塩
食塩、塩化アンモニウム、塩化カルシウムなど
億）溶剤
イソゾロビルアルコール、プロピレングリコール、エチ
レングリコールナト
また、これらの他にも尿素、殺菌剤、酸化防止剤、更に
製品の外観のために顔料または染料を、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
ために香料上配合することもできる。CH,0H R14COO(CH,CH20) Xo-Co -R1
5R,4COO(CH2CH,0) xo-H [in the formula,
xo#'i1~10o number, xl, )'1%zl is Xl
A number that satisfies +7t +Zs = 100, I2, y!
, z2 each represent a number from θ to 100. R14 and R15
has the same meaning as above. ] (e) Fatty acid R1, C00H (in the formula, R14 has the same meaning as above) (d)
Anionic surfactant fat e [sodium alkylbenzene sulfonate, alkyl sulfate ester salt, alkylnaphthalene sulfonate, alkyl phosphate, etc. (e) Ampholytic surfactant alkyldimethylaminoacetic acid betaine, alkylcarboxymethylhydroxyethylimidazolinium peta In addition to these, urea, bactericides, antioxidants, and product appearance Pigments or dyes may also be included for the purpose, fluorescent brighteners for whiteness of the finish, and perfumes for use and after finish.
本発明の柔軟仕上剤は、各種繊維に対してその吸水性能
を損なうことなく柔軟性、帯電防止性を付与することが
できる。The fabric softener of the present invention can impart flexibility and antistatic properties to various fibers without impairing their water absorption performance.
以下に実施例を挙げて説明するが、本発明はこれらに限
定されるものではない。Examples will be described below, but the present invention is not limited thereto.
（グル液晶転移温度測定方法）
柔軟基剤をイオン交換水中に５重量％分散させたものを
測定試料とし、セイコー電子工業株式会社製の熱分析装
置５ＳＣ１５８０７１Ｊ −ズＤＳＣ１０にて測定し、
ピークの立ち上がりをグル液晶転移温度とした。詳細な
条件は以下の通りである。(Method for Measuring Glue Liquid Crystal Transition Temperature) Using a 5% by weight dispersion of a flexible base in ion-exchanged water as a measurement sample, the measurement was performed using a thermal analyzer 5SC158071J-DSC10 manufactured by Seiko Electronics Co., Ltd.
The rise of the peak was defined as the liquid crystal transition temperature. The detailed conditions are as follows.
測定試料約１０１１９をアルミニウム製の１５μｇ密封
型試料容器に取り、空の密封型容器を対照とし、約−３
０℃まで冷却した後０．５〜１．０℃（／ｍｉｎの昇温
速度で加熱し、０〜６０℃の間を測定する。このときの
ピークの立ち上がりをゲル液晶転移温度とする。なお、
０〜６０℃の範囲にピークが２つ以上存在する場合は、
最も高温側のピークの立ち上がり温度を採用する。Approximately 10,119 measurement samples were placed in a 15 μg sealed aluminum sample container, and an empty sealed container was used as a control, and approximately -3
After cooling to 0°C, heat at a temperature increase rate of 0.5 to 1.0°C (/min) and measure between 0 and 60°C. The rise of the peak at this time is defined as the gel-liquid crystal transition temperature. ,
If two or more peaks exist in the range of 0 to 60°C,
The rising temperature of the peak on the highest temperature side is used.
（評価）
（１）柔軟処理方法
市販の木綿タオルを市販洗剤ザブ（花王株式会社製、登
録商標）にて５回繰り返し洗濯をし、布についている洗
剤を除去した後、柔軟仕上剤の０．１％水溶液（３，５
°ＤＨ硬水）にて２５℃、浴比１／３０で５分間攪拌下
処理した。(Evaluation) (1) Softening treatment method A commercially available cotton towel was washed 5 times with a commercially available detergent Zab (manufactured by Kao Corporation, registered trademark) to remove the detergent on the cloth, and then the softening agent was removed. 1% aqueous solution (3,5
DH hard water) at 25°C and a bath ratio of 1/30 for 5 minutes with stirring.
２）評価方法
上記方法で処理した布を室内で風乾後、２５℃、６５％
皿の恒温恒湿室にて２４時間放置した。これらの布につ
いて柔軟性及び吸水性の評価を行った。2) Evaluation method After drying the cloth treated with the above method indoors, 25°C, 65%
The dish was left in a constant temperature and humidity room for 24 hours. These fabrics were evaluated for flexibility and water absorption.
■ 柔軟性
ジオクタデシルジメチルアンモニウムクロライド（試料
Ａ１８、比較品）で処理した布を対照にして一対比較を
行い、下記評価基準により評価した。(2) Flexibility A pairwise comparison was made using a cloth treated with dioctadecyldimethylammonium chloride (sample A18, comparative product) as a control, and evaluation was made according to the following evaluation criteria.
＋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
■ 吸水性
柔軟仕上剤で処理した木綿タオルを３ａｎＸ２０ｃｒＲ
の短冊状に切り取り、その一端２備を水に浸す。１５分
後の水の上昇高さを測定した。+2 Softer than the control +1 Slightly softer than the control 0 Same as the control -1 Slightly softer the control -2 Softer the control
Cut it into a strip and soak one end of it in water. The height of water rise after 15 minutes was measured.
実施例１
第１表に示す二鎖型第四級アンモニウム塩５重量％を水
中に分散させて柔軟仕上剤屋１〜１８を調製し、これに
よって処理された木綿タオルの柔軟性と吸水性について
上述の評価方法に従って調べた。結果を第１表に示す。Example 1 Fabric softeners 1 to 18 were prepared by dispersing 5% by weight of two-chain quaternary ammonium salts shown in Table 1 in water, and the flexibility and water absorption of cotton towels treated with the fabric softeners 1 to 18 were examined. It was investigated according to the evaluation method described above. The results are shown in Table 1.
実施例２
硬化牛脂アルキル−（２−メチルウンデフル）−ジメチ
ルアンモニウム・メチル丈ルフエート ５重量％エチレ
ンクリコール ４重量％水
ノ（ランス上記組成成
分を用い、配合温度や攪拌用プロペラの回転速度を変化
させて分散質の平均粒径の異なる柔軟仕上剤ａ −ｅ
′ｆ：調製した。Example 2 Hardened tallow alkyl-(2-methylundefur)-dimethylammonium methyl sulfate 5% by weight ethylene glycol 4% by weight water
(lance) By using the above composition components and changing the compounding temperature and the rotational speed of the stirring propeller, softening agents a-e with different average particle diameters of dispersoids are prepared.
'f: Prepared.
これを２５℃で４８時間保存した後、前述の方法に従っ
て処理した各木綿タオルの柔軟性と吸水性について調べ
た。結果を第２表に示す。なお、分散質の粒度分布は、
コールタ−カウンター（ＴＡ−ＩＩ型、７〕９−チャー
チュー７” ５０１１ｍ 、 Ｃ０ＵＬＴＥＲＥＬＥＣ
ＴＲＯＮＩＣ８社製）を用いて、２５℃で４８時間放置
した各種柔軟仕上剤について測定した。After storing this at 25° C. for 48 hours, each cotton towel treated according to the above-mentioned method was examined for flexibility and water absorption. The results are shown in Table 2. In addition, the particle size distribution of the dispersoid is
Coulter Counter (TA-II type, 7) 9-char-chou 7” 5011m, C0ULTERELEC
TRONIC 8) was used to measure various fabric softeners that had been left at 25°C for 48 hours.
以下余白Below margin
Claims (1)
鎖のアルキル基またはβ−ヒドロキシアルキル基、Ｒ＿
２は炭素数１０〜２４の分岐鎖のアルキル基またはβ−
ヒドロキシアルキル基で、Ｒ＿１とＲ＿２は３個以上の
炭素数の差を有するものとする。Ｒ＿３及びＲ＿４は炭
素数１〜３のアルキル基もしくはヒドロキシアルキル基
、ベンジル基または−（Ｃ＿２Ｈ＿４Ｏ）＿ｎＨ（但し
、ｎは２〜３を示す）を示し、Ｘはハロゲン原子または
炭素数１〜３のアルキル基を有するモノアルキル硫酸塩
基を示す〕 で表わされる非対称二鎖型第四級アンモニウム塩を含有
することを特徴とする柔軟仕上剤。 ２、非対称二鎖型第四級アンモニウム塩のゲル液晶転移
温度が３０℃以下である特許請求の範囲第１項記載の柔
軟仕上剤。 ３、非対称二鎖型第四級アンモニウム塩を、分散粒子の
粒度分布が５μｍ以下のものが９０％以上になるように
、水に分散したものである特許請求の範囲第１項記載の
柔軟仕上剤。[Claims] 1. General formula (I) ▲ Numerical formula, chemical formula, table, etc. ▼ (I) [In the formula, R_1 is a linear or branched alkyl group having 10 to 24 carbon atoms or β-hydroxy Alkyl group, R_
2 is a branched alkyl group having 10 to 24 carbon atoms or β-
In the hydroxyalkyl group, R_1 and R_2 have a difference in the number of carbon atoms of 3 or more. R_3 and R_4 represent an alkyl group or hydroxyalkyl group having 1 to 3 carbon atoms, a benzyl group, or -(C_2H_4O)_nH (where n represents 2 to 3), and X is a halogen atom or a hydroxyalkyl group having 1 to 3 carbon atoms. a monoalkyl sulfate group having an alkyl group] A softening agent characterized by containing an asymmetric two-chain quaternary ammonium salt represented by 2. The fabric softener according to claim 1, wherein the asymmetric two-chain quaternary ammonium salt has a gel-liquid crystal transition temperature of 30°C or lower. 3. The flexible finish according to claim 1, which is obtained by dispersing an asymmetric two-chain quaternary ammonium salt in water such that the particle size distribution of the dispersed particles is 90% or more of 5 μm or less. agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9713587A JPS63260991A (en) | 1987-04-20 | 1987-04-20 | Softening finish agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9713587A JPS63260991A (en) | 1987-04-20 | 1987-04-20 | Softening finish agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63260991A true JPS63260991A (en) | 1988-10-27 |
Family
ID=14184125
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9713587A Pending JPS63260991A (en) | 1987-04-20 | 1987-04-20 | Softening finish agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63260991A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2254325A (en) * | 1991-04-03 | 1992-10-07 | Kao Corp | Ammonium salts and hair treating agent containing the same |
-
1987
- 1987-04-20 JP JP9713587A patent/JPS63260991A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2254325A (en) * | 1991-04-03 | 1992-10-07 | Kao Corp | Ammonium salts and hair treating agent containing the same |
| GB2254325B (en) * | 1991-04-03 | 1995-03-15 | Kao Corp | Ammonium salts and hair treating agent containing the same |
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