JPS63203872A - Novel fiber post-processing treatment agent - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

[Detailed Description of the Invention] Conventionally, surfactants have a wide range of properties such as emulsification, dispersion, cleaning, wetting, foaming, etc., and these properties are used to improve the production of fibers, paper, etc. rubber, plastic, gold clay,
It is used in various fields such as paints, pigments, and civil engineering and construction. Particularly recently, there has been an active movement toward improving the performance of end products using surfactants, and along with this, secondary drawbacks of surfactants have also been pointed out.

For example, paints, printing inks, adhesives, pressure-sensitive adhesives, and the like are indispensable in the production of products, product stability, and workability. When these products are used for coating, printing, adhesion, adhesion, etc., surfactants are not necessary; rather, the surfactants present can affect the coating film 1, printed surface, adhesive film, etc. It often deteriorates the water resistance, oil resistance, etc. of

As a countermeasure to these problems, efforts have been made to reduce the amount of surfactants blended and to use polymeric surfactants, but these problems have not yet been fully resolved in terms of product stability, workability, etc. not present.

On the other hand, in order to provide new types of surfactants, there are many patents for polymerizable, reactive, or degradable surfactants.

For example, as an anionic surfactant,
No. 12472, JP-A-54-14431, JP-A-1973
-34894, Japanese Patent Publication No. 56-29657, Japanese Patent Publication No. 56-2965
1-30285, Japanese Patent Publication No. 49-46291, and Japanese Patent Application Laid-open No. 127697-1982, etc. As nonionic surfactants, Japanese Patent Publication No. 56-28208 and Japanese Patent Publication No. 50-98
There are issues such as No. 484.

The present invention is based on the general formula: RO(AO)ICIIzCIICHzOCHzCtl=
Cllzmon0 (AO) m503M [However, in the above formula, R is a furkyl group having 8 to 30 carbon atoms,
an alkenyl group, an alkylaryl group, an aralkylaryl group, A is an alkylene group having 2 to 4 carbon atoms, or a substituted alkylene group, n is an integer from 0 to 100,
m is an integer from 1 to 200, M is an alkali metal atom,
NH4 is an alkanolamine residue. ] Provided is a fiber post-processing agent characterized by comprising a compound represented by the following.

In the general formula, R is an alkyl group, alkenyl group, alkylaryl group, or aralkylaryl group having 8 to 30 carbon atoms, and examples of the alkyl group include octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, and tetradecyl. , pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, and the like.

Examples of the alkenyl group include octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl,
Examples include heptadecenyl and octadecenyl.

As the alkylaryl group, monobutylphenol,
dibutylphenol, 5ec-butylphenol, di5
Examples include ec-butylphenol, tert-butylphenol, octylphenol, nonylphenol, dinonylphenol, dodecylphenol, and didecylphenol.

Examples of aralkylphenols include styrenated phenol, benzylphenol, cumylphenol, etc. mono-, di-, and tri-single or a mixture thereof.
A mixture of these alkyl groups and the like may be used.

Further, A is an alkylene group or a substituted alkylene group having 2 to 4 carbon atoms, such as ethylene, propylene, butylene, isobutylene, etc., and may be a single group or a block or random mixture thereof.

n is an integer of 0 to 100, m is an integer of 1 to 200,
More preferably n is O or 1-50, m is 2-100
is within the range of

Furthermore, the fiber post-processing agent of the present invention can be easily manufactured industrially, and can be manufactured, for example, as follows. That is, nonylphenol or lauryl alcohol is used as a raw material, alkylene oxide is added if necessary, allyl glycidyl ether is heated and reacted in the presence of a catalyst, and alkylene oxide is further added to the obtained reaction composition in a conventional manner. and add it. Next, sulfuric acid,
It can be obtained by sulfating with a sulfamic acid or other sulfamic acid and neutralizing with a basic substance if necessary.

EXAMPLES Hereinafter, the present invention will be specifically explained with reference to Examples, but the present invention is not limited thereto.

(% 1 part indicates weight basis.) Production Example 1 220 g (1.0 mol) of nonylphenol and 1.5 g of triethylamine as a catalyst were charged into a reaction vessel equipped with a stirrer, a thermometer, and a reflux tube. 114 g (1.0 mol) of glycidyl ether was added dropwise and stirred at 100° C. for 5 hours.

Next, the obtained reaction composition was transferred to an autoclave, and the pressure was 1.5 kg/cnl using caustic potassium as a catalyst.
10 mol, 30 mol, and 100 mol of ethylene oxide were added to the reaction composition at a temperature of 130° C. to obtain compositions. Next, in a reaction vessel equipped with a stirrer and a thermometer, 387 g (0.5 mol) of the 10 mol ethylene oxide adduct of the above reaction composition and 58.2 mol of sulfamic acid were added.
g (0.6 mol) was charged, the temperature was raised to 120°C, and the reaction was stirred for 3 hours to perform sulfation. The composition obtained by daily removal of unreacted sulfamic acid was treated with the surfactant of the present invention (A
). The ammonium sulfate ester of an adduct of 30 moles of ethylene oxide obtained in the same manner was used as the surfactant of the present invention [B], and the ammonium sulfate of a 100 mole of ethylene oxide adduct was used as the surfactant of the present invention ( C).

! ! l! ! Production Example 2 186 g (1.0 mol) of lauryl alcohol and 0.6 g of boron trifluoride ether complex as a catalyst were placed in a reaction vessel equipped with two stirrers, a thermometer, and a reflux tube, and then 228 g (2,0 mol) of allyl glycidyl ether was charged. 0 mol) was added dropwise at 80°C.
After stirring for 5 hours, the mixture was heated to 120°C, and excess allyl glycidyl ether was removed under reduced pressure. Next, the obtained reaction composition was transferred to an autoclave and heated with caustic potassium as a catalyst at a pressure of 1.5 kg/csl and a temperature of 13.
The compositions obtained by adding 5 mol, 20 mol, and 50 mol of ethylene oxide to the reaction composition at 0°C were sulfated according to Production Example 1, and the obtained ethylene oxide 5 The molar adduct ammonium sulfate ester was added to the surfactant of the present invention [D] and ethylene oxide 20
The sulfate ammonium salt of the molar adduct was used as the surfactant of the present invention [E];
).

Production Example 3 Into a reaction vessel equipped with a stirrer, a thermometer, and a reflux tube, 856 g (1.0 moles) of a block adduct of 10 moles of distyrenated phenol ethylene oxide and 2 moles of propylene oxide, and 2 g of boron trifluoride ether complex as a catalyst were charged. Next, 228 g (2.0 mol) of allyl glycidyl ether was added dropwise, and after stirring at 80°C for 5 hours, the mixture was heated to 120°C, and excess allyl glycidyl ether was removed under reduced pressure. Next, the obtained reaction composition was transferred to an autoclave and heated at a pressure of 1.5 kg/kg using caustic potassium as a catalyst.
The composition obtained by adding 15 mol and 40 mol of ethylene oxide to the reaction composition at 130°C was sulfated according to Production Example 1, and the resulting ethylene A sulfate ammonium salt of a 15 mole oxide adduct was used as the surfactant of the present invention [G], and a sulfate ammonium salt of a 40 mole ethylene oxide adduct was used as a surfactant of the present invention (H).

Preparation Example 4 1588 g of 30 mole adduct of oleyl alcohol ethylene oxide was placed in a reaction vessel equipped with a stirrer, a thermometer, and a reflux tube.
(1.0 mol), 3 g of boron trifluoride ether complex as a catalyst, and then 228 g of allyl glycidyl ether.
(2.0 mol) was added dropwise, stirred at 80°C for 5 hours, heated to 120°C, and excess allyl glycidyl ether was removed under reduced pressure. Next, the obtained reaction composition was transferred to an autoclave, and a pressure of 1
．． A composition obtained by randomly adding 40 moles of ethylene oxide and 10 moles of propylene oxide to the reaction composition under conditions of 5 kg/cnl and a temperature of 130°C was prepared using sulfamic acid according to Production Example 1. To the obtained sulfated product, an amount of caustic soda equivalent to sulfamic acid was added to remove ammonia, and the obtained sulfuric ester sodium salt was used as the surfactant (1) of the present invention.

Production Example 5 385 g of stearyl alcohol propylene oxide 2 mol adduct was placed in a reaction vessel equipped with a stirrer, thermometer, and reflux tube.
(1.0 mol), 1.5 g of boron trifluoride ether complex as a catalyst, and then allyl glycidyl ether 22
8 g (2.0 mol) was added dropwise, stirred at 80°C for 5 hours, then heated to 120°C, and excess allyl glycidyl ether was removed under reduced pressure. Next, the obtained reaction composition was transferred to an autoclave, and 2 moles and 5 moles of ethylene oxide were added using caustic potassium as a catalyst at a pressure of 1.5 kg/cj and a temperature of 130°C. According to Production Example 1, sulfation is carried out using sulfamic acid, monoethanolamine in an amount equivalent to sulfamic acid is added to the obtained sulfated product, and ammonia is removed. The ester monoethanolamine salt was used as the surfactant of the present invention [J], and the sulfuric acid ester monoethanolamine salt of a 5 mole ethylene oxide adduct was used as the surfactant of the present invention (K).

Production Example 6 Di5eC-
Butylphenol butylene oxide 3 mole adduct 27
8 g (1.0 mol), 1 g of boron trifluoride ether complex as a catalyst, and then allyl glycidyl ether 22
8 g (2.0 mol) was added dropwise, stirred at 80°C for 5 hours, heated to 120"C, and excess allyl glycidyl ether was removed under reduced pressure. Next, the resulting reaction composition was autoclaved. Using caustic potassium as a catalyst, 2 moles of propylene oxide and 15 moles of ethylene oxide were added to the reaction composition under conditions of a pressure of 1.5 kg/ctA and a temperature of 130°C, and the resulting composition was Sulfation was carried out according to Production Example 1, and the obtained sulfate ester ammonium salt was used as the surfactant (L) of the present invention.

Production Example 7 Tribenzylphenol ethylene oxide 20 mol adduct 124 was placed in a reaction vessel equipped with a stirrer, a thermometer, and a reflux tube.
4 g (1.0 mol) and 4 g of boron trifluoride ether complex as a catalyst, then allyl glycidyl ether 22
8 g (2.0 mol) was added dropwise, stirred at 80°C for 5 hours, then heated to 120°C, and excess allyl glycidyl ether was removed under reduced pressure. Next, the obtained reaction composition was transferred to an autoclave, using caustic potassium as a catalyst, under the conditions of a pressure of 1.5 kg/cni and a temperature of 130°C.
5 moles of propylene oxide was added to the reaction composition, and the resulting composition was sulfated according to Production Example 1, and the obtained sulfate ester ammonium salt was used as the surfactant CM) of the present invention. .

Example 1 Surfactant (A) of the present invention obtained in Manufacturing Machinery 7
~(M), the surface tension of its aqueous solution was measured.

In addition, the surface tension of a conventional surfactant is also shown as a comparative product. (Surface tension was measured using the Traube method.) The results are shown in Table 1.

Example 2 Non-woven fabric made from polypropylene (2,5 (JXlo
(J) was immersed for 1 minute in a 1% aqueous solution of the surfactant shown in Table 2, taken out, and then dried with hot air at 120° C. for 30 minutes.

The above surfactant-treated nonwoven fabric was mixed with 50 liquid of water.
It was hung over a 0d beaker and immersed in water by Icm from the bottom of the nonwoven fabric, and the height of water penetration after 5 minutes was measured. (Before washing) In order to further observe washing resistance, the nonwoven fabric after treatment and drying was washed with running water for 1 minute, dried, and subjected to the same water permeability test as above. The results (after washing) are shown in Table 2.

(Margin below)

Claims (1)

[Claims] There are general formulas, ▲mathematical formulas, chemical formulas, tables, etc.▼ [However, in the above formula, R is an alkyl group having 8 to 30 carbon atoms,
an alkenyl group, an alkylaryl group, an aralkylaryl group, A is an alkylene group having 2 to 4 carbon atoms, or a substituted alkylene group, n is an integer from 0 to 100,
m is an integer from 1 to 200, M is an alkali metal atom,
NH_4, alkanolamine residue. ] A fiber post-processing agent characterized by comprising a compound represented by the following.