JPS5869874A - Ampho-ionic compound - Google Patents

Abstract

NEW MATERIAL:A compound of formulaI[R<1> is 1-26C hydrocarbon group; R<2> is H or lower alkyl; R<3> is alkylene, phenylene or aralkylene; X<1> is H, OH, a group of formula II (M is a metallic ion; (n) is an integer corresponding to the valence of M) or glycidyloxy; X<2> and X<3> are H, group of formula II or glycidyl; at least one of X<1>, X<2> and X<3> contains glycidyl group; (a), (b) and (c) are 0 or positive integers and (a+b+c) is 1-200]. USE:A modifying agent for molded polymeric articles, e.g. fibers or films. PROCESS:A 1,2-epoxyalkane is reacted with a mono- or diethanolamine, and if necessary an alkylene oxide is then added thereto. The resultant reaction product is then reacted with a compound of formula III (X is halogen) in the presence of a strong base and then reacted with epichlorohydrin in the presence of a strong base to afford the compound of formulaI.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a zwitterionic compound useful as a modifier for polymer moldings such as crafts and films. It is related to a sexual ionic compound.

Ha- ε
"-8Os" M (M is a metal ion, n is an integer corresponding to the valence of V) or Gly-V diloki V group 18.18
is hydrogen 2-R"-8Ox" M or ktlf9Vt) #
In addition, at least one of car') XI, lf port, xa
contains a GlyVvp group.

a, b, o are O or positive integers a+b+am1~200
*) The compounds of the present invention also include compounds in which 80m- forms a salt with a metal ion and a hydroxyl group is coordinated to the ridge.

The compound of the present invention is a compound that has a zwitterion structure, an aquiline V-do structure, and a glycan-V di- group in its molecule, and is a substance that belongs to the so-called 2-responsive amphoteric surfactants, and when added to a polymer. It has the effect of improving the hygroscopicity, antistatic property, dyeing stability, etc. of the polymer. The compounds of the present invention are also expected to be applied to pharmaceuticals, inks, paper processing agents, detergents, cosmetics, and the like.

Various additives have been proposed to give antistatic properties to polymers 1, but many of them have insufficient performance or impair the original properties of polymers.
Bulletin No. 0 discloses a compound similar to the present invention in which the anion site of the zwitterion is a carboxylate,
Although the polymer had comparatively excellent performance, it did not have sufficient heat resistance.6 The present inventors improved the antistatic performance and heat resistance by using sulfonate as the anion site, and melt-molded the polymer. By introducing a highly reactive GlyVv~ group into the same molecule, a surprising effect is achieved in which coloring does not occur at times, and 9
They discovered that it is possible to impart long-lasting antistatic properties through a chemical reaction with a polymer.

In the compound of the present invention, R1 may have a substituent such as a halogen or a nitro group, and R1 is preferably hydrogen or a methyl group, and desirably a+b+a≧10. Hs
Specific examples of -CH-, -CHaCHa--CH
aCHmCXIm-, leprosy (CHx)-, -C6Ha-,
-CHm-C5Ha- and the like.

The compound of the present invention is synthesized by the following method.

The first method is to react 1,2-EvokiV alkane with mono- or jetanolamine, add alkylene oxide if necessary, and then react +X-R''-3Os-M(X
is a halogen), such as sodium monochloromethanesulfonate, is reacted in the presence of a chemical group such as NaOH, and then epichlorohydrin is reacted in the presence of a strong base such as -1. .

1g Ni no kata tjt it R” CFlmQHmNH
s, R''CH(OH)Q(mNHm)J: After adding ethylene oxide V-do to the amine, a sulfonate compound was reacted in the same manner as in the first method.

This method involves reacting epichlorohydrin.

In these methods, when reacting the sulfonate compound, C [by adjusting the sulfonate ratio.

Compounds in which part of XI,
This can be made to correspond to the corresponding non-IIS of other metals.

Next, examples and application examples of the present invention will be shown.

Example 6.74 f of stearylamine, 50 da of potassium hydroxide as a catalyst and 589 of ethylene oxide were sealed in a high-pressure reaction vessel at 0°C, and heated and stirred at 180°C for 12 hours. After the reaction, a waxy product was taken out. The product was used as it was in the next amphoteric reaction. The composition of the ethylene oxide adduct was determined from nuclear magnetic resonance spectroscopy, and was found to contain a 50-mer of oxy-V ethylene units. Similarly, 150 amounts of ethylene oxide were synthesized by appropriately increasing or decreasing the amount of ethylene oxide charged.

50 amounts of ethylene oxide per stearylamine Dissolve sodium chloride 7, Of in 150 d of water.

After the reaction was heated at 100°C for 18 hours, the water was evaporated to dryness. J! The I residue was dissolved in methylene chloride. After removing the insoluble precipitate, methylene chloride was removed under reduced pressure to obtain a pale yellow waxy target product 97f.

Amphoterization of other different ethylene oxide adducts was carried out in a similar manner.

To the above amphoteric product 30f made with stearinamine and 50 ethylene oxide and thorium, 5 times the molar amount of epichlorohydrin and 5 times the molar amount of Fium hydroxide were added, and the mixture was heated at 70-80°C for SO hours. After 0 reaction, V ethyl ether A//n-'hexane (1
:111 quantitative ratio) and the precipitate was extracted with anhydrous ethanol μ.

The target product was reprecipitated by pouring it into diethyl-ether fi//n-hexane again to obtain a pale yellow waxy substance SSf.

The spectral data for identification is shown below.

Infrared absorption spectrum pv s 5460tT" (-OH
group), 3050r1 ('T7 group), 2950
．． 2890m1′″” (-Gin- group) * 125
Qcyl (-Sos- group), 1110 (C-0- group) nuclear magnetic resonance 7 He? ) A/ (CDCIs) S
2O-81 (m, cHsLα1-!5.2-3.5 (■, Ta, Sho (H-Sushiichi V)
, 3.6 (go 1 hit 0).

3.6-4.2 (m, OCHm"completed) (5,6-
Approximately 60g from the integral ratio of the peaks of 4.2 and 3.6
It can be seen that the -OH group of No. 6 is converted into glycerinated V.

) Reactions with other amphoteric compounds with different amounts of ethylene oxide addition with echuroμhydrin were carried out in the same manner.

Application Example 1 A methanol solution of tuts of the substance obtained in Example (ethyene oxide 30-mer adduct) cd? After soaking the polyester fibers in Tough P*, they were squeezed with a mangle and then heated at 120C for 10 minutes. The obtained taffeta was boiled in hot water for 50 minutes, washed with running water, and then dried in a vacuum dryer.

As a control example, taffeta made from additive-free methanol to solution-cured ethylene terephthalate fibers was dipped, and tack was prepared through the same treatment.

Relative humidity of tag treated with the present invention and taffeta of control example 60
96. Static honest meter at 20°C (m degrees)
Shishido Mukai! The half-life according to 1) is 1.4 seconds and 10, respectively.
It was 0 seconds or more.

Application Example 2 5 parts by weight of the substance obtained in Example (ethylene oxide V-dos 50-mer adduct) and 1 part normal polyethylene terephthalate 9
7 parts by weight were mixed and spun using an extruder-type melt spinning machine at a melt #1 temperature of 280°C and a residence time of 5 minutes, and then stretched according to a conventional method to obtain a fiber of 75d/16f and a diameter of 3.5g. /a, a drawn yarn with an elongation of 30% was obtained.

The operability during spinning and drawing was good.

After the obtained drawn yarn was knitted, it was scoured and dyed in a bath containing a blue disperse dye at 120° C. for 1 hour.

The half-life of the obtained dyed cloth at a relative humidity of 40% and a temperature of 20° C. was 22 seconds, confirming good antistatic property ζ. Even after repeating the home laundry process 50 times, in which the dyed fabric is treated in a washing solution containing 19/l of neutral detergent for 10 minutes at room temperature, the half-life value of the fabric remains unchanged. There was one power.

Patent applicant: Takeo Sanae

Claims (1)

[Claims] (1) A zwitterionic compound represented by the following general formula. R" -5Os- (R1 is a C1-26 swelling hydrogen group, R- is hydrogen or a lower alkyl group, Hm is an alkylene group, phenylene group, or hot poxy group, Xi is hydrogen, hydroxyl group, -0-R"
-8On”M (MG! metal ion, n is an integer corresponding to the value of the animal) or GrivNpwOkiV group, ]C”*X”
is hydrogen. -R"-8Dm M or uvspst*,
1. x Maro. At least one of xl' also contains a Gly Vνy group. a, b, 6 are 0 or positive integers a+b+om1-200
,).