JPH11199534A - Alkylene oxide adduct composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject composition having a narrow alkylene oxide adduct distribution, not solidified or not becoming cloudy, even when left at the ordinary temperature, and capable of being easily handled by reacting an active hydrogen-containing organic compound with an alkylene oxide so as to give the specific composition. SOLUTION: This alkylene oxide composition is obtained by reacting an active hydrogen-containing organic compound of the formula: R1 H with an alkylene oxide of formula I [R2 and R3 are each hydrogen or a 1-3C hydrocarbon; (n) is 1-30]. The alkylene oxide composition contains alkylene oxide adducts of formula II [(m)=(n)-1, (m)=(n) and (m)=(n)+1] in a total amount of 35-50 wt.%. The reaction for obtaining the composition is preferably carried out in the presence of a phosphazenium salt such as a compound of formula III [(a)-(d) are each 0-3, wherein (a)-(d) are simultaneously not 0; R is a 1-3C hydrocarbon; (r) is 1-3 which is the number of the phosphazenium cations; T<r> is an inorganic anion having a valency (r)] as a catalyst.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to an alkylene oxide adduct composition. Alkylene oxide adduct compositions of organic compounds containing active hydrogen such as higher alcohols are important as industrial nonionic components or nonionic components in cosmetic detergents and detergents, and furthermore, emulsifiers, dispersants, etc. It is a compound that is used in a wide range of fields as intermediates for solvents, solvents, polyurethane resin raw materials, and chemical products. Above all, in the field of surfactants, alkylene oxide adduct compositions having a narrow alkylene oxide addition molar distribution include: 1) no unpleasant odor due to a small amount of residual unreacted alcohol; 2) high cloud point; and 3) foaming power. It has advantages such as excellent permeability, detergency, etc., and is often desired.

[0002]

2. Description of the Related Art These alkylene oxide adduct compositions are usually produced by reacting an active hydrogen-containing compound such as a higher alcohol with an alkylene oxide in the presence of an acid or base catalyst. As the acid catalyst, a mineral acid such as sulfuric acid, hydrochloric acid, phosphoric acid or the like or a metal salt thereof, or a metal salt of a carboxylic acid such as acetic acid or oxalic acid is used. Examples of the base catalyst include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and amines such as diethylamine and triethylamine. On the other hand, as a method for obtaining an alkylene oxide adduct composition having a narrow alkylene oxide addition molar distribution, for example, 1) a method using barium oxide as a catalyst (US Pat. No. 4,239,91)
7) 2) A method using a catalyst which is a basic salt of calcium and / or strontium and a co-catalyst such as phosphoric acid (JP-A-58-189128); 3) MgO to which Si ⁴⁺ and Ba ²⁺ are added Method for use as a catalyst (JP-A-5-170)
688), 4) a method using hydrotalcite (JP-A-5-981), 5) a method using metal oxide (JP-A-7-227540), and 6) a method using calcined hydrotalcite (JP-A-8-9849) 268919 and JP-A-2-
71841) has been proposed.

[0003]

However, when producing the alkylene oxide adduct composition using the above-mentioned acid or base catalyst, there are some problems. That is, with a general homogeneous base catalyst, only one having a wide addition molar distribution can be obtained, and unreacted raw materials remain in the reaction product, which impairs the quality of the resulting alkylene oxide adduct composition. Furthermore, when an alkylene oxide adduct composition having an alkylene oxide addition mole number of about 6 to 9 mol is produced, the reaction solution is left at room temperature to form a cloudy substance, and the entire reaction solution becomes cloudy or precipitates. In addition, when an acid catalyst is used, the amount of unreacted raw materials in the reaction product is reduced, but dioxane and its derivative, a cyclic ether, or polyethylene glycol are by-produced, which also affects the quality of the formed alkylene oxide adduct composition. give.

On the other hand, when a catalyst for giving the above-mentioned narrow alkylene oxide adduct distribution is used, an alkylene oxide adduct composition having a small by-product and a narrow alkylene oxide addition molar distribution can be obtained.
However, because of the heterogeneous catalyst, it is necessary to separate the catalyst from the reaction products. There is also a problem that the reaction activity (feed rate of alkylene oxide per gram of catalyst per hour) is lower than that of a homogeneous basic catalyst such as an alkali metal or alkaline earth hydroxide. Further, among the alkylene oxide adduct compositions having a narrow alkylene oxide addition molar distribution obtained by these catalysts, the alkylene oxide addition mole number is 6 to 9
Alkylene oxide adduct compositions that are moles often produce cloudy matter at room temperature or become jelly-like,
There was a problem that handling was extremely difficult.

[0005]

Means for Solving the Problems The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, the alkylene oxide adduct composition having a specific composition has a narrow alkylene oxide adduct distribution. At the same time, they have found that they have excellent liquid properties without solidification or turbidity even when left at room temperature, and thus completed the present invention. That is,
The present invention relates to an alkylene oxide adduct composition obtained by reacting an active hydrogen-containing organic compound represented by the reaction formula [1] with an alkylene oxide, and the alkylene oxide adduct I, II, III ( Adduct I is m = n-1
An alkylene oxide adduct, adduct II is an alkylene oxide adduct m = n, adduct III is m = n +
The alkylene oxide adduct which is 1) is 35.
It is an alkylene oxide adduct composition of not less than 50% by weight and not more than 50% by weight.

[0006]

Embedded image (In the reaction formula, R ₁ H represents an organic compound containing at least one active hydrogen atom, R ₂ and R ₃ are a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms, and n and m are 1 to 30. Is a positive integer of

The alkylene oxide adduct composition of the present invention is preferably produced by using a phosphazenium salt represented by the following formulas (1) (formula 5) and (2) (formula 6) as a catalyst. be able to.

[0008]

Embedded image

[0009]

Embedded image

(In the formulas [1] and [2], a,
b, c and d each represent a positive integer of 3 or less or 0. However, a, b, c and d are not simultaneously 0. R represents the same or different hydrocarbon groups having 1 to 3 carbon atoms, and two Rs on the same nitrogen atom may combine with each other to form a cyclic structure. r is an integer of 1 to 3 and represents the number of phosphazenium cations, and ^Tr- represents an inorganic anion having a valence of r. Q ^- represents a hydroxy anion, an alkoxy anion, an aryloxy anion or a carbanion)

The alkylene oxide adduct composition obtained in the present invention has a small amount of unreacted raw materials and reaction by-products, and has a narrow alkylene oxide addition molar distribution as compared with conventional basic homogeneous catalysts. It has low viscosity and does not cause cloudiness, and is extremely easy to handle.

Further, since the phosphazenium salt catalyst used in the present reaction is a homogeneous catalyst, complicated filtration is not required, and the catalytic activity (the feed amount of alkylene oxide /
g catalyst ・ hr) is high.

[0013]

BEST MODE FOR CARRYING OUT THE INVENTION The active hydrogen-containing organic compound used in the present invention may be any organic compound which forms an alkylene oxide adduct by reacting with an alkylene oxide. Examples thereof include alcohols, phenols and polyols. , Thiols, carboxylic acids, amines, amides and mixtures thereof. As the alcohol, a saturated or unsaturated primary or secondary alcohol having 6 to 20 carbon atoms is preferable. For example, primary alcohols include n-octanol, n-nonal, n-decanol, n-dodecanol, n-tridecanol, n-tetradecanol,
n-pentadecanol, n-hexadecanol, n-heptadecanol, n-octadecanol, n-nonadecanol, n-eicosanol, 2-methyl-1-nonal, 2-methyl-1-undecanol, 2- Methyl-1
-Dodecanol, 2-methyl-1-tetradecanol, and secondary alcohols include 3-heptanol,
-Octanol, 2-decanol, 2-dodecanol,
Representatives include 4-tetradecanol, 6-heptadecanol, cyclohexanol, cyclopentanol, and cyclooctanol. Also, commercially available products include C
₁₂ KALCOL 20 alkanols composition is more than 95%
(Trade name, manufactured by Kao Corporation), C _13, C ₁₅ alkanol composition each of 60,39% of DAIADOL135 (trade name:
Manufactured by Mitsubishi Chemical Corporation), C _12, alkanol compositions are each 45% C _13, 55% of the DOBADOL (trade name: manufactured by Mitsubishi Chemical Corporation), Konokoru 2 mainly composed of alkanol to C ₁₂
0 (trade name: Shin Nippon Rika Co., Ltd.), C _12, alkanol composition of each 40% of C _13, 60% of NEODOL23 (trade name: manufactured by Shell Chemical Company), alkanol composition of each of the C _12, C ₁₄ 54%, 44% ALFOL1214
(Product name: manufactured by CONDEA CHEMIE), C ₁₂ ,
Alkanol compositions are each 43% C _13, 57% of the LIA
An alkanol mixture represented by L123 (trade name: manufactured by Enikem Co., Ltd.) is exemplified.

As phenols, phenol, p-
Methylphenol, p-ethylphenol, p-butylphenol, p-hexylphenol, p-heptylphenol, p-nonylphenol, p-decylphenol, dinonylphenol, didecylphenol, vinylphenol, allylphenol, m-dihydroxybenzene, p -Dihydroxybenzene, 2,4-toluenediol, 1,3,5-toluene thiol, 2,2-bis (4'-hydroxyphenyl) propane and the like.

Examples of the polyols include ethylene glycol, propylene glycol, hexylene glycol, decylene glycol, diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, glycerin, sorbitol, and trimethylolpropane.

The thiols include butanethiol, 1
Primary thiols represented by hexanethiol, dodecanethiol, 1-tetradecanethiol, 2-methyl-1-tridecanethiol, 2-propanethiol, 2
-Butanethiol, 3-pentanethiol, 2-decanethiol, 3-decanethiol, 4-decanethiol,
5-decanethiol, 2-hexadecanethiol, 5-
Secondary thiol and tertiary thiol represented by hexadecanethiol and 8-octadecanethiol.

The carboxylic acids include acetic acid, propionic acid, octanoic acid, lacnic acid, valeric acid, caproic acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, rosin acid, tall oil acid, acrylic acid, Methacrylic acid, vinyl acetic acid, crotonic acid, maleic acid, fumaric acid, adipic acid, aliphatic carboxylic acids represented by 1,2,3-propanetricarboxylic acid, terephthalic acid, benzoic acid, vinylbenzoic acid, phenylacetic acid, toluyl Acid, 1,
It is an aromatic carboxylic acid represented by 2,4-benzenetricarboxylic acid.

The amines include aliphatic amines represented by tert-butylamine, laurylamine, ethylenediamine, diethylenetriamine, and aromatic amines represented by N-methylaniline. As amides, formamide, N, N-dimethylformamide,
N, N-dimethylacetamide, octylamide, decylamide, laurylamide, stearylamide, acrylamide, oxamide, benzamide, p-methoxybenzamide, p-hydroxybenzamide and the like. On the other hand, the alkylene oxide has an oxirane ring and may be any one as long as it reacts with an active hydrogen organic compound to form an adduct.Ethylene oxide and propylene oxide are most commonly used. Mixing may be used.

The phosphazenium salt catalyst used in the present invention is a compound represented by the formula [1] (formula 5) and the formula [2] (formula 6). Regardless, tetrakis [tris (dimethylamino) phosphoranylideneamino] phosphonium hydroxide, which is (1,1,1,1), tetrakis [tris (diethylamino) phosphoranylideneamino] phosphonium hydroxide or , A, b, c, d are (0,
(1,1,1), (dimethylamino) tris [tris (dimethylamino) phosphoranylideneamino] phosphonium hydroxide, (dimethylamino) tris [tris (dimethylamino) phosphoranylideneamino] phospho But R is a methyl group, and a, b, c, and d are irrespective of order (1,
In the case where tetrakis [tris (dimethylamino) phosphoranylideneamino] phosphonium hydroxide, which is 1,1,1), the effect of the present invention is remarkable, it is preferable.

The amount of the catalyst of the present invention varies depending on the amount of alkylene oxide to be added to the active hydrogen-containing organic compound and the reaction temperature, but is usually 0.001 to 5% by weight based on the adduct formed. More preferably 0.0
1 to 1% by weight. If the amount is less than 0.001% by weight, a sufficient reaction rate cannot be obtained. If the amount is more than 5% by weight, the reaction proceeds sufficiently, but the amount of the catalyst used is undesirably large. The reaction temperature of the present invention is from 80 ° C to 230 ° C, more preferably 1 to 230 ° C.
00 ° C to 180 ° C. If it is lower than 80 ° C., a sufficient reaction rate cannot be obtained, and if it is higher than 230 ° C., the formed adduct is decomposed. The reaction pressure is preferably in the range of 0 to 15 kg / cm ² , depending on the type and amount of the active hydrogen compound and the alkylene oxide used, and the reaction temperature.
More preferably, it is in the range of 1 to 6 kg / cm ² .

The addition reaction of the alkylene oxide is
The reaction is preferably performed within a certain pressure from the viewpoint of safety. Therefore, the feed rate of the alkylene oxide is determined by factors such as the reaction temperature and the type of catalyst.

[0022]

The present invention will be described below in more detail with reference to examples. Example 1 0.1 g of tetrakis [tris (dimethylamino) phosphoranylideneaminophosphonium hydroxide (hereinafter abbreviated as TTDPPH) represented by the formula [3] in an autoclave with a stirrer having an internal volume of 200 ml.
Then, 38 g (0.2 mol) of 1-dodecyl alcohol was charged, and a nitrogen gas was flown therein to make the inside of the autoclave a nitrogen atmosphere, and then the temperature was raised to 135 ° C. while stirring. Five minutes later, the supply of ethylene oxide was started, and the temperature was raised to 145 ° C in five minutes. Thereafter, the reaction temperature is 145 ° C., and the reaction pressure is 4 kg.
The reaction was carried out for 1 hour and 45 minutes while maintaining / cm ² G. During this time, 62 g (1.4 mol) of ethylene oxide
Was supplied.

After aging at a reaction temperature of 145 ° C. for about 40 minutes, the mixture was cooled to room temperature and the reaction solution was taken out. The feed rate of ethylene oxide was 338 g / g catalyst · hr.
The resulting ethylene oxide adduct was measured for OH value,
Thereby, the average number of moles added was calculated. In addition, analysis by gas chromatography and liquid chromatography is performed,
The addition molar distribution was determined. The average number of moles added was 6.85, unreacted alcohol was 0.90% by weight, and by-product polyethylene glycol was 0.6% by weight. The ethylene oxide addition molar distribution is shown by curve A in FIG. Adduct I, I
The sum of I and III was 40.9% by weight. Further, the obtained reaction solution was transparent and did not become cloudy even when left at room temperature for several days.

[0024]

Embedded image

Example 2 After charging 0.15 g of the catalyst TTDPPH in the same manner as in Example 1, the temperature was raised to 90 ° C., and after stabilizing for 5 minutes, the supply of EO was started. After about 5 minutes from the start of the reaction, the temperature was raised to 100 ° C., after which the reaction temperature was 100 ° C. and the reaction pressure was 4 kg / c.
The reaction was performed for 5 hours and 45 minutes while maintaining m ² G.
During this time, 62 g (1.4 mol) of ethylene oxide was supplied. The alkylene oxide adduct obtained after aging and cooling was analyzed in the same manner as in Example 1. The results are shown in Table 1 (Table 1). In addition, the liquid properties and physical properties are shown in Table 3 (Table 3).

Example 3 After 0.5 g of the catalyst TTDPPH was charged in the same manner as in Example 1, the temperature was raised to 90 ° C., and after 5 minutes of stabilization, the supply of EO was started. After about 5 minutes from the start of the reaction, the temperature was raised to 100 ° C., after which the reaction temperature was 100 ° C. and the reaction pressure was 4 kg / cm.
^The reaction was performed for 2 hours and 55 minutes while maintaining 2G. During this time, 62 g (1.4 mol) of ethylene oxide was supplied. The alkylene oxide adduct obtained after aging and cooling was analyzed in the same manner as in Example 1. The results are shown in Table 1 (Table 1). In addition, the liquid properties and physical properties are shown in Table 3 (Table 3).

Example 4 After charging 0.15 g of the catalyst TTDPPH in the same manner as in Example 1, the temperature was raised to 110 ° C., and after stabilizing for 5 minutes, the supply of EO was started. After about 5 minutes from the start of the reaction, the temperature was raised to 120 ° C., after which the reaction temperature was 120 ° C. and the reaction pressure was 4 kg /
While maintaining cm ² G, the reaction was carried out for 2 hours and 55 minutes. During this time, 62 g (1.4 mol) of ethylene oxide
Was supplied. After cooling and aging, the alkylene oxide adduct obtained after cooling was analyzed in the same manner as in Example 1. The results are shown in Table 1 (Table 1). In addition, the liquid properties and physical properties are shown in Table 3 (Table 3).

Example 5 After charging 0.05 g of the catalyst TTDPPH in the same manner as in Example 1, the temperature was raised to 150 ° C., and after stabilizing for 5 minutes, the supply of EO was started. After about 5 minutes from the start of the reaction, the temperature was raised to 160 ° C., after which the reaction temperature was 160 ° C. and the reaction pressure was 4 kg /
While maintaining cm ² G, the reaction was performed for 2 hours and 20 minutes. During this time, 62 g (1.4 mol) of ethylene oxide
Was supplied. The alkylene oxide adduct obtained after aging and cooling was analyzed in the same manner as in Example 1.
The results are shown in Table 1 (Table 1). In addition, the liquid properties and physical properties are shown in Table 3 (Table 3).

Example 6 After charging 0.02 g of the catalyst TTDPPH in the same manner as in Example 1, the temperature was raised to 150 ° C., and after stabilizing for 5 minutes, the supply of EO was started. After about 5 minutes from the start of the reaction, the temperature was raised to 160 ° C., after which the reaction temperature was 160 ° C. and the reaction pressure was 4 kg /
While maintaining cm ² G, the reaction was carried out for 4 hours and 55 minutes. During this time, 62 g (1.4 mol) of ethylene oxide
Was supplied. The alkylene oxide adduct obtained after aging and cooling was analyzed in the same manner as in Example 1.
The results are shown in Table 1 (Table 1). In addition, the liquid properties and physical properties are shown in Table 3 (Table 3).

Example 7 After charging 0.02 g of the catalyst TTDPPH in the same manner as in Example 1, the temperature was raised to 160 ° C., and after 5 minutes of stabilization, the supply of EO was started. After about 5 minutes from the start of the reaction, the temperature was raised to 170 ° C., after which the reaction temperature was 170 ° C. and the reaction pressure was 4 kg /
While maintaining cm ² G, the reaction was performed for 3 hours and 15 minutes. During this time, 62 g (1.4 mol) of ethylene oxide
Was supplied. The alkylene oxide adduct obtained after aging and cooling was analyzed in the same manner as in Example 1.
The results are shown in Table 1 (Table 1). In addition, the liquid properties and physical properties are shown in Table 3 (Table 3).

[0031]

[Table 1]

Comparative Example 1 Example 1 except that 0.10 g of KOH was used as a catalyst.
The same operation as that described above was carried out at a temperature of 145 ° C and a reaction pressure of 4 kg /
The reaction was performed for 2 hours while maintaining cm ² G. During this time, 62 g (1.4 mol) of ethylene oxide was supplied. The alkylene oxide adduct obtained after aging and cooling was analyzed in the same manner as in Example 1. The average number of moles added was 6.88, unreacted alcohol was 2.26% by weight, and by-product polyethylene glycol was 0.9% by weight.
The ethylene oxide addition molar distribution is shown in curve B of FIG. The sum of adducts I, II and III was 27.9% by weight. The reaction liquid became cloudy when left at room temperature.

Comparative Example 2 Example 1 except that 0.06 g of KOH was used as a catalyst.
Then, the temperature was raised to 150 ° C., and after 5 minutes of stabilization, the supply of EO was started. The temperature was raised to 160 ° C. in about 5 minutes after the start of the reaction, and thereafter, the reaction was carried out for 1 hour and 40 minutes while maintaining the reaction temperature at 160 ° C. and the reaction pressure at 4 kg / cm ² G. During this time, 62 g of ethylene oxide (1.
4 mol). The alkylene oxide adduct obtained after aging and cooling was analyzed in the same manner as in Example 1. The results are shown in Table 2 (Table 2). In addition, the liquid properties and physical properties are shown in Table 3 (Table 3).

Comparative Example 3 As a catalyst, Kyoward-2000 [manufactured by Kyowa Chemical Co., Ltd.] (used after calcining at 500 ° C. for 3 hours in an air atmosphere)
The same operation as in Example 1 was carried out except that 0.5 g was used, and the reaction was carried out for 1 hour and 55 minutes while maintaining the temperature at 145 ° C. and the reaction pressure at 4 kg / cm ² G. During this time, 62 g (1.4 mol) of ethylene oxide was supplied. The alkylene oxide adduct obtained after aging and cooling was analyzed in the same manner as in Example 1. Average number of moles added 6.78,
It was 0.5% by weight of unreacted alcohol and 0.7% by weight of by-produced polyethylene glycol. The ethylene oxide addition molar distribution is shown in curve C of FIG. Adducts I, II, II
The sum of I was 63.3% by weight. The reaction solution had a high viscosity and was cloudy, so that the catalyst could not be separated (filtered).

Comparative Example 4 As a catalyst, Kyoward-2000 (manufactured by Kyowa Chemical) (empty)
(Fired at 500 ° C for 3 hours in air atmosphere before use)
After charging 0.20 g in the same manner as in Example 1, 17
After the temperature was raised to 0 ° C. and stabilized for 5 minutes, the supply of EO was started.
After about 5 minutes from the start of the reaction, the temperature was raised to 180 ° C.
Reaction temperature 180 ° C, reaction pressure 4kg / cm ^TwoHold G
The reaction was performed for 1 hour and 50 minutes. During this time ethylene
62 g (1.4 mol) of oxide were fed. Aging, cold
The alkylene oxide adduct obtained after rejection was the same as in Example 1.
Analysis was performed in a similar manner. The results are shown in Table 2 (Table 2)
Shown in The liquid properties and physical properties are shown in Table 3 (Table 3).
You.

Comparative Example 5 As a catalyst, Kyoward-2000 (manufactured by Kyowa Chemical) (empty)
(Fired at 500 ° C for 3 hours in air atmosphere before use)
After charging 0.50 g in the same manner as in Example 1, 11
After the temperature was raised to 0 ° C. and stabilized for 5 minutes, the supply of EO was started.
After about 5 minutes from the start of the reaction, the temperature was raised to 120 ° C.
Reaction temperature 120 ° C, reaction pressure 4kg / cm ^TwoHold G
The reaction was performed for 3 hours and 45 minutes. During this time ethylene
62 g (1.4 mol) of oxide were fed. Aging, cold
The alkylene oxide adduct obtained after rejection was the same as in Example 1.
Analysis was performed in a similar manner. The results are shown in Table 2 (Table 2)
Shown in The liquid properties and physical properties are shown in Table 3 (Table 3).
You.

Comparative Example 6 As a catalyst, Kyoward-500 (manufactured by Kyowa Chemical Co., Ltd.) (used after firing at 300 ° C. for 3 hours in an air atmosphere)
The same operation as in Example 1 was performed except that 5 g was used, and the reaction was performed for 9 hours while maintaining the temperature at 145 ° C. and the reaction pressure at 4 kg / cm ² G. During this time ethylene oxide 4
4 g (1.0 mol) were fed. The alkylene oxide adduct obtained after aging and cooling was analyzed in the same manner as in Example 1. The average number of moles added was 4.91, unreacted alcohol was 0.7% by weight, and by-product polyethylene glycol was 2.0% by weight. The ethylene oxide addition molar distribution is shown in curve D of FIG. The sum of adducts I, II and III is
It was 58.5% by weight. The reaction solution had a low viscosity but a slight cloudiness was observed.

Comparative Example 7 As a catalyst, Kyoward-500 (manufactured by Kyowa Chemical Co., Ltd.) (used after firing at 300 ° C. for 3 hours in an air atmosphere)
After charging 5 g in the same manner as in Example 1, the temperature was raised to 170 ° C., and after stabilizing for 5 minutes, the supply of EO was started. The temperature was raised to 180 ° C. in about 5 minutes after the start of the reaction, and thereafter, the reaction was carried out for 4 hours and 45 minutes while maintaining the reaction temperature at 180 ° C. and the reaction pressure of 4 kg / cm ² G. During this time, 62 g (1.4 mol) of ethylene oxide was supplied. The alkylene oxide adduct obtained after aging and cooling was analyzed in the same manner as in Example 1. The results are shown in Table 2 (Table 2). In addition, the liquid properties and physical properties are shown in Table 3 (Table 3).

[0039]

[Table 2]

[0040]

[Table 3]

[0041]

The alkylene oxide adduct composition obtained according to the present invention has a small amount of unreacted raw materials and reaction by-products, and has a narrow alkylene oxide addition molar distribution as compared with a conventional basic homogeneous catalyst, but at room temperature. Also has a low viscosity and is extremely easy to handle without causing cloudiness or the like. In particular, the alkylene oxide addition mole number is 6 to 9
The effect is remarkable in the alkylene oxide adduct composition of

[Brief description of the drawings]

FIG. 1 shows the ethylene oxide addition molar distribution of the ethylene oxide adduct composition obtained in the examples. In FIG. 1, the horizontal axis represents the number of moles of ethylene oxide added, and the vertical axis represents the ethylene oxide adduct produced. Shown is the weight percentage of each molar adduct relative to the total weight of the composition. Curves A, B, C, and D represent the molar distribution of ethylene oxide addition of the ethylene oxide adduct compositions obtained in Example 1 and Comparative Examples 1, 3, and 6, respectively.

 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Uji Sanji 1190 Kasama-cho, Sakae-ku, Yokohama-shi, Kanagawa

Claims (2)

[Claims] 1. An alkylene oxide adduct composition obtained by reacting an active hydrogen-containing organic compound represented by the following reaction formula [1] with an alkylene oxide:
Alkylene oxide adducts I, II, III (adduct I is m
= N-1; adduct II is an alkylene oxide adduct where m = n; adduct III is an alkylene oxide adduct where m = n + 1), and the sum of the contents is 35% by weight or more. , 50% by weight or less of an alkylene oxide adduct composition. Embedded image (In the reaction formula, R ₁ H represents an organic compound containing at least one active hydrogen atom, R ₂ and R ₃ represent a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms, and n and m are 1 to 30. Represents a positive integer of 2. The alkylene oxide adduct according to claim 1, wherein the reaction is carried out in the presence of a phosphazenium salt represented by the following formula [1] (formula 2) or formula [2] (formula 3). Composition. Embedded image Embedded image (In the formulas [1] and [2], a, b, c, and d each represent a positive integer of 3 or less or 0.
b, c and d are not simultaneously 0. R represents the same or different hydrocarbon groups having 1 to 3 carbon atoms, and two Rs on the same nitrogen atom may combine with each other to form a cyclic structure.
r is an integer of 1 to 3 and represents the number of phosphazenium cations, and ^Tr- represents an inorganic anion having a valence of r. Q ^- represents a hydroxy anion, an alkoxy anion, an aryloxy anion or a carbanion)