JPS6191156A - 2-hydroxyethyl-mono and/or poly(oxyethyl)trialkyl ammonium hydroxide and its solution - Google Patents

Abstract

NEW MATERIAL:The 2-hydroxyethyl-(mono and/or polyoxyethyl)trialkyl ammonium hydroxide of formula (R, R' and R'' are 1-5C alkyl; 1<=n<=10). EXAMPLE:Trimethyl hydroxyethoxyethyl ammonium hydroxide. USE:An etchant, releasing agent, etc., for the film, sheet, etc., of photosetting resin, or a cleaning agent, etc., for a glass article to which especially high cleanness is required. PREPARATION:A compound of formula I wherein n is 1 can be prepared e.g. by reacting a trialkylamine with 2-(2'-chloroethoxy)ethanol, and exchanging the halogen ion of the resultant trialkyl 2-hydroxyethoxyethyl ammonium halide with hydroxyl ion.

Description

Detailed Description of the Invention (Field of Industrial Application) The present invention is applicable to films made of photocurable frame resin, etching agents such as V-T, and release agents such as glass products requiring purity. (2) Concerning new useful compounds and swamps containing them;

(1st technique) General C: Tip rod used for foot training etc.
Tetramethylammonium hydroxide and strong organic alkaline compounds such as choline are used as etching agents or embossing agents for the resin film that is cured by the second process. (For example, see JP-A-56-35424)
In addition, strong alkaline compounds such as those mentioned above are used as cleaning agents for glassware and the like that require high cleanliness.

(Problem to be solved by the invention) However, diluting the above-mentioned compound L: Therefore, the etching liquid! l! When etching a resin film as described above, although there is a dependence on the degree of For example, when removing the resin film after etching in the integrated circuit manufacturing process, the concentration of the compound in the removal agent may be lowered to minimize effects other than the removal of the extremely fat film. However, there was a problem with the process that the peeling time was prolonged.

(Means for Solving the Problems) As a result of intensive studies in view of the above points C and 2, it was discovered that a compound having a specific structure, which is not described in the known literature, would solve the above drawbacks, and the present invention ( : Reached.

That is, 1 the present invention is represented by the following general formula [I]l: 2
-Hydroxylethyl-(mono and/or polyoxylethyl) trialkylammonicum hydroxide and a specific solution containing the same.

The compound of the present invention represented by the general formula [I]
Process C for producing the compounds of the present invention, which only describes ammonium salts such as ammonium nitrate, is not limited in any way. For example, assuming the case of n-1, trialkylamine and 2 - (2'-Chloroethoxy)ethanol or N,N-9 alkylaminoethoxyethanol is reacted with alkylparite to give trialkyl 2-hydrokine ethylammonium halide, and this halogen ion is converted by known method C. It can be produced by exchanging it with hydroxide ion. Furthermore, for a mixture of 20 or more and 10 or less, for example, in a suitable medium, C nitrialkylamine and water in an amount of at least the same amount are present, and a predetermined amount of ethylene oxide is added in an amount of at least the same amount of the trialkylamine. It can be produced by addition reaction C2.

R, nr, and R7 in the general formula [I] are each the same or different alkyl group having 1 to 5 carbon atoms, preferably an alkyl group having 1 to 3 carbon atoms. When the number of carbon atoms exceeds 5, the weight of the alkyl group itself in the present compound increases, and therefore the molecular weight of the compound increases. For example, assuming a solution with a constant content, the alkali equivalent This is not preferable because it reduces For the same reason, R, R'
, R' are all methyl groups.

In the general formula (I), n represents the average number of repeating units, preferably 1 or more and 1O or less. When this is less than 1 or more than 1O, the compound of the present invention is used as a photocurable resin. It is undesirable as a melting agent, an etching agent, a peeling agent, a cleaning agent for glass products, etc.

As mentioned above, the compounds of the present invention can be present alone or as a mixture, and therefore, the compounds of the present invention can be used alone or as a mixture in ml=c% as described above.

Although it is difficult to isolate the compound of the present invention both as a single substance and as a mixture, 1- is stably present in a specific solvent. Examples of this solvent include water and aliphatic alcohols having 1 to 4 carbon atoms such as methanol, ethanol, isopropyl alcohol, and 5ec-butanol.

There are no particular limitations on the method for producing a solution containing the compound of the present invention in the solvent, but the compound may be produced in the solvent, or the solvent may be removed by distillation from the solution for other purposes. You can gradually add the molasses. Thereafter, the same or different solvent is added to this solution to adjust the concentration. The concentration of the solution is 1% by weight or more and 30% by weight or less, and it is diluted as necessary when used.

As mentioned above, the compound of the present invention is a new compound that has not been described in any known literature, and its confirmation was carried out using the method described in the known literature "Organic Wt Quantitative Analysis" (edited by the Organic Microanalysis Council, published by Nankodo). I went though.

The details will be described in the Examples section (== described below).

(Example) The present invention will be further explained in detail with reference to Examples below. In the following, 1: part refers to part by weight (unless otherwise specified).

Example 1 (Production example of trimeb-ruhydroki V-ethoxyethylammonium hydroxide) Contents a 5 oomt pressure container C 200 parts of nimethanol.

72.8 parts of trimethylamine was charged and the reaction was completed by heating at 100°C (two times, followed by 5 drops of 2-(2'-chloroethoxylate)ethanol). Thereafter, methanol was removed from the reaction mixture by distillation under reduced pressure, and 300 parts of acetone was added. Trimethylhydroxyethoxyethylammonium chloride was crystallized using an electric shock, and 176 parts were isolated by a known method. (Yield 96%) (= dissolve.

The total amount was 1000 parts, and an exchange column filled with anion exchange resin (Diaion 5A-1OA OH type) 700 g (total exchange capacity 0.91 e), which had been regenerated in advance + = 8 V. When the solution was passed through the solution at a rate of -2, 1170 parts of an aqueous solution containing 6.0% by weight of trimethylhydroxyethoxyethylammonium hydrooxide was obtained.

fsitv (Confirmation of trimethylhydroxyethylammonicum hydroxide) When an aqueous solution of sodium tetraphenylboron was added to the reaction solution pumped out from the ion exchange tower, a precipitate was formed. From the above-mentioned literature, it is estimated that this precipitate was generated according to the following formula (II). Therefore, in the aqueous solution, ammonium hydroxa
) ((Cs錇)4B〕+NaOH・・・・・・
...(IF) Next C: When phosphotungstic acid was added to the effluent from the ion exchange tower mentioned above, and the resulting precipitate was dried and quantified, it was thermally decomposed at about 800°C, resulting in phosphotungstic acid anhydride. was gotten. That is, the following (III) and
H)zOH+H,PO,・12'WO.

((CHs)sNC TOC 00H! CHIOH
)s PO4 ・12WOs+3H,O・・・・・・・
...(III)((C8),NCH,C)1,O
CH,C)(,OH),PO,・12WO.

△ The reaction progresses and trimethyl hydroxide V analyzed by this method
The molecular weight of ethoxyv ether ammonium hydride oxide was calculated to be 167.2.

From the above qualitative and quantitative analysis results, the formation and
existence confirmed.

Example 2 200 parts of 6-dimethanol in a pressure-resistant container with a content of SOOMJ.

Add 94.5 parts of triethylamine 130'c1=
After heating.

Add 135 parts of 2-(2'-(2'-chloroethoxyV)ethoxylate) ethanol over 1 hour, and then add 4 parts at the same temperature.
Continue stirring for an hour to finish the reaction. After that, Example 1
When crystallized in the same manner as above, triethyl 2-(
20 5.0 parts of 2″-(2#-hydrokine ethoxy)+ethylammonicum chloride were obtained.

(Yield 95%) Add 94.5 parts of the above ammonium chloride to pure water at r8
Therefore, the total amount was 1000 parts, which was the same as in Example 1.
When the liquid was passed through a fat column at 5V=2, triethyl 2-
1440 parts of a solution containing 6.1 parts and 5% of C2'-C2''-hydrokineethoxy)ethoxy]ethylammonium hydroxide were obtained.

This solution was used for analysis according to the method described in Example 1.

The production and existence of the above compound was confirmed.

Examples 3 to 6 Water and trimethylamine were charged in a pressure-resistant container with a content of 500 mJ in the proportions shown in Table 1, and ethylene oxide was added over 2 hours at the specified hot water temperature, followed by post-stirring at the same temperature for 1 m 1 hour. I went. The container was opened and water was added to dilute the solution to a concentration of about 15 gk% to prevent coloring. The above results are shown in Table ff11.

Furthermore, each aqueous solution was analyzed by the method described in Example 1, and the production and presence of quaternary ammonium hydroxide was confirmed.

Example 7 A solution prepared by dissolving 80 parts of trimethylhydroxyethoxyethylammonium chloride prepared in Example 1 (1) in 150 parts of ethanol (= 5% ethanol solution) was mixed with the chloride and our company. The precipitate was added and the precipitate was removed. The precipitate was in situ potassium, and its 1FF was 31.9 parts. Therefore, it was estimated that 98% of the chloride was converted to hydroxide C. This solution ( - About 2000 parts of water was added, and as much ethanol as possible was distilled off under pressure of about 301 parts g. After that, analysis was performed using the method described in Example 1, and the formation and presence of the above compound was confirmed.

(Effects of the Invention) The present invention provides a novel compound which is useful as a dissolving agent, an etching agent, a stripping agent for photocured resin, and a cleaning and cleaning agent for glass products.

Procedural amendment July 6, 1985

Claims (1)

[Claims] 1. 2-hydroxyethyl-(mono and/or polyoxyethyl) trialkylammonium hydroxide represented by the following general formula [I]. ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・・・・
... [I] [Here, R' and R'' have the same or different carbon numbers from 1 to
In the alkyl group of 5, n indicates the average number of repeating units and is a positive number of 1 or more and 10 or less. 2. The compound according to claim 1, wherein R, R', and R'' are the same or different alkyl groups having 1 to 3 carbon atoms. 3, R, R', and R'' are methyl groups. A compound according to claim 2. 4 Contains 2-hydroxyethyl-(mono and/or polyoxyethyl) trialkylammonium hydroxide represented by the following general formula [I], ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・I
] [Here, R, R', and R'' each have the same or different carbon number 1
-5 alkyl group, n indicates the average number of repeating units and is a positive number of 1 or more and 10 or less. ] Water and/or carbon number 1~
4. Solution using aliphatic alcohol as a solvent. 5. The solution according to claim 4, which contains a compound in which R, R', and R'' in the general formula [I] are each the same or different alkyl group having 1 to 3 carbon atoms. 6. The solution according to claim 4 6. The solution according to claim 5, which contains a compound in which R, R', and R'' in formula [I] are methyl groups, and uses water as a solvent.