JPH0229068B2 - DAI4KYUANMONIUMUSUISANKABUTSUNOCHAKUSHOKUBOSHIHOHO - Google Patents
DAI4KYUANMONIUMUSUISANKABUTSUNOCHAKUSHOKUBOSHIHOHOInfo
- Publication number
- JPH0229068B2 JPH0229068B2 JP2194083A JP2194083A JPH0229068B2 JP H0229068 B2 JPH0229068 B2 JP H0229068B2 JP 2194083 A JP2194083 A JP 2194083A JP 2194083 A JP2194083 A JP 2194083A JP H0229068 B2 JPH0229068 B2 JP H0229068B2
- Authority
- JP
- Japan
- Prior art keywords
- hydroxide
- quaternary ammonium
- added
- ammonium hydroxide
- mtea
- 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.)
- Expired - Lifetime
Links
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 19
- 239000000908 ammonium hydroxide Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 14
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 10
- -1 aminoalcohol amine Chemical class 0.000 claims description 4
- 229920000768 polyamine Polymers 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 18
- 238000004040 coloring Methods 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 8
- 238000005259 measurement Methods 0.000 description 6
- 241001550224 Apha Species 0.000 description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- HADKRTWCOYPCPH-UHFFFAOYSA-M trimethylphenylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C1=CC=CC=C1 HADKRTWCOYPCPH-UHFFFAOYSA-M 0.000 description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052910 alkali metal silicate Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 2
- FIVJMCNNMIGYRO-UHFFFAOYSA-N bis(2-hydroxyethyl)-dimethylazanium Chemical compound OCC[N+](C)(C)CCO FIVJMCNNMIGYRO-UHFFFAOYSA-N 0.000 description 2
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical group O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZLRANBHTTCVNCE-UHFFFAOYSA-N 2-phenyl-3-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CN=C1C1=CC=CC=C1 ZLRANBHTTCVNCE-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- SLXQCTLNJSRAIV-UHFFFAOYSA-N [OH-].C(C1=CC=CC=C1)C(CC1=CC=CC=C1)[NH3+] Chemical compound [OH-].C(C1=CC=CC=C1)C(CC1=CC=CC=C1)[NH3+] SLXQCTLNJSRAIV-UHFFFAOYSA-N 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229940107816 ammonium iodide Drugs 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は第４級アンモニウム水酸化物の着色を
防止する方法に関するものである。
第４級アンモニウム水酸化物は、シリカゾル、
珪酸アルカリ等の結合剤への添加剤や、塗料への
添加剤等に広く用いられているが、このものは極
めて着色し易く、製造後数十時間で着色が進行す
るので、実用上問題があつた。
この着色を防止するため、種々の方法が提案さ
れてきた。例えば第４級アンモニウム水酸化物を
製造した後、更に製造する方法は有効ではある
が、精製工程のため製品コストが高くなる点で好
ましくない。製品の保存を窒素封入下で行うと
か、酸化防止剤を添加する方法も提案されている
が、着色防止には必ずしも有効でなく、長期の着
色防止は困難であつた。
特開昭51−54505号には、第４級アンモニウム
水酸化物の製造中またはその製造直後にコロイド
状シリカまたは珪酸アルカリを添加する方法が提
案されている。この方法もかなり有効であるが、
着色防止効果を長期にわたつて維持するために
は、添加剤を多量に用いる必要があり、また添加
剤がコロイド状であるため製品に濁りを生じて、
外観上商品価値を下げるという難点がある。
本発明は第４級アンモニウム水酸化物に特定の
アミン類を添加することによつて、その着色を長
期間防止する方法を提供するものであつて、１分
子中にアミノ基を２〜８個有する脂肪族アミン
を、第４級アンモニウム水酸化物に対し0.01〜10
重量％添加することを特徴とする、第４級アンモ
ニウム水酸化物の着色防止方法である。
本発明における第４級アンモニウム水酸化物
は、例えば第３級アミン類と沃化アルキルとを反
応させて得られる第４級アンモニウム沃化物を、
陰イオン交換体で処理するかまたは水と酸化銀で
処理する方法、あるいはアンモアまたはアミン類
にアルキレンオキシドを反応させる方法等、種々
の方法によつて製造される。
これらの第４級アンモニウム水酸化物として
は、例えばモノメチルトリエタノールアンモニウ
ム・ヒドロキシド、ジメチルジエタノールアンモ
ニウム・ヒドロキシド、ジメチルジイソプロパノ
ールアンモニウム・ヒドロキシド、トリメチルエ
タノールアンモニウム・ヒドロキシド、テトラメ
チルアンモニウム・ヒドロキシド、テトラエチル
アンモニウム・ヒドロキシド、テトラエタノール
アンモニウム・ヒドロキシド、フエニルトリメチ
ルアンモニウム・ヒドロキシド、ベンジルトリメ
チルアンモニウム・ヒドロキシド、ジベンジルメ
チルアンモニウム・ヒドロキシド等がある。これ
らの第４級アンモニウム水酸化物は、通常、水ま
たは親水性有機溶媒の溶液として得られ、そのま
まか、または溶媒を除去した形で用いられる。本
発明で用いられる脂肪族アミンは、１分子中にア
ミノ基を２〜８個有するもので、特に一般式
H2N〔（CH2）nNH〕oＨ
（ここでｍは１〜５、好ましくは２〜３であ
り、ｎは１〜６、好ましくは１〜５である）で表
わされる直鎖状の脂肪族ポリアミンが有効であ
る。このような脂肪族ポリアミンとしては、例え
ばエチレンジアミン、ジエチレントリアミン、ト
リエチレンテトラアミン、ペンタエチレンヘキサ
ミン、１，３―プロパンジアミンが特に有効であ
る。
本発明で用いられる脂肪族アミンとしてはアミ
ノアルコールアミン類も用いられ、例えばアミノ
エチルエタノールアミンが有効に用いられる。
これらの脂肪族アミンの添加量は、第４級アン
モニウム水酸化物に対して0.01〜10重量％、好ま
しくは0.1〜５重量％である。添加量が上記範囲
より少ない場合には、本発明における着色防止効
果を十分にあげることができず、また多すぎる添
加量は第４級アンモニウム水酸化物の用途によつ
ては好ましくない結果を生ずる。
本発明において用いられる脂肪族アミンは、単
独で用いられる他、数種併用して用いることもで
きる。
第４級アンモニウム水酸化物は、一般にその製
造後に経時着色し、時間の経過と共にその着色度
を増大するが、本発明の方法によれば、脂肪族ア
ミンの添加によつて経時的着色進行を防止するこ
とができる。従つて、通常は第４級アンモニウム
水酸化物の製品化に際して、脂肪族アミンが添加
されるが、第４級アンモニウム水酸化物の製造方
法により、特に支障のない場合には、第４級アン
モニウム水酸化物の合成反応終了直後に脂肪族ア
ミンを添加してもよい。
以下、実施例によつて本発明の効果を示す。
実施例 １〜４
モノメチルアミンにエチレンオキイドを付加さ
せて、モノメチルトリエタノールアンモニウム・
ヒドロキシド（以下MTEAと略称する）の25％
水溶液を製造し、製造１時間後にエチレンジアミ
ンをそれぞれMTEAに対し0.1、0.5、1.0および
3.0重量％を添加した。この４種のMTEA水溶液
を、室温で放置し、経時着色をJISK―6901に従
つてAPHA色調基準によつて測定した。測定結
果は第１表に示す。
比較例 １
実施例１に用いたと同じMTEA25％水溶液を、
そのまま室温に放置した場合のAPHA着色変化
を測定した。測定結果は第１表に示すとおりで、
第２日目以降着色が急激に進行した。
比較例 ２、３
実施例１に用いたと同じMTEA25％水溶液に
シリカゾル（日産化学工業(株)製、SiO3として30
％含有）をSiとしてMTEAに対しそれぞれ0.3重
量％および1.0重量％を添加し、この２種の
MTEA水溶液を室温で放置し、APHA着色変化
を測定した。測定結果は第１表に示す。
The present invention relates to a method for preventing coloration of quaternary ammonium hydroxide. Quaternary ammonium hydroxide is silica sol,
It is widely used as an additive to binders such as alkali silicate, and as an additive to paints, but it is extremely easy to color, and the coloring progresses within several tens of hours after production, so it poses a practical problem. It was hot. Various methods have been proposed to prevent this coloring. For example, a method in which quaternary ammonium hydroxide is produced and then further produced is effective, but is not preferable because the product cost increases due to the purification process. Methods such as storing the product under nitrogen or adding an antioxidant have been proposed, but these methods are not necessarily effective in preventing coloration, and long-term prevention of coloration has been difficult. JP-A-51-54505 proposes a method in which colloidal silica or alkali silicate is added during or immediately after the production of quaternary ammonium hydroxide. This method is also quite effective, but
In order to maintain the anti-coloring effect over a long period of time, it is necessary to use large amounts of additives, and since the additives are in colloidal form, they can cause cloudiness in the product.
The problem is that it lowers the product value due to its appearance. The present invention provides a method for preventing coloring of quaternary ammonium hydroxide for a long period of time by adding specific amines to the quaternary ammonium hydroxide. aliphatic amine with 0.01 to 10
This is a method for preventing discoloration of quaternary ammonium hydroxide, which is characterized by adding the quaternary ammonium hydroxide in a weight percent. The quaternary ammonium hydroxide in the present invention is, for example, a quaternary ammonium iodide obtained by reacting a tertiary amine with an alkyl iodide.
It can be produced by various methods, such as treatment with an anion exchanger or water and silver oxide, or reaction of ammour or amines with alkylene oxide. Examples of these quaternary ammonium hydroxides include monomethyltriethanolammonium hydroxide, dimethyldiethanolammonium hydroxide, dimethyldiisopropanolammonium hydroxide, trimethylethanolammonium hydroxide, tetramethylammonium hydroxide, Examples include tetraethylammonium hydroxide, tetraethanolammonium hydroxide, phenyltrimethylammonium hydroxide, benzyltrimethylammonium hydroxide, and dibenzylmethylammonium hydroxide. These quaternary ammonium hydroxides are usually obtained as a solution in water or a hydrophilic organic solvent, and are used as they are or in a form with the solvent removed. The aliphatic amine used in the present invention has 2 to 8 amino groups in one molecule, and particularly has the general formula H 2 N [(CH 2 ) n NH] o H (where m is 1 to 5, A linear aliphatic polyamine represented by the formula (preferably 2 to 3, and n is 1 to 6, preferably 1 to 5) is effective. Particularly effective examples of such aliphatic polyamines include ethylenediamine, diethylenetriamine, triethylenetetraamine, pentaethylenehexamine, and 1,3-propanediamine. As the aliphatic amine used in the present invention, aminoalcohol amines are also used, and for example, aminoethylethanolamine is effectively used. The amount of these aliphatic amines added is 0.01 to 10% by weight, preferably 0.1 to 5% by weight, based on the quaternary ammonium hydroxide. If the amount added is less than the above range, the coloring prevention effect in the present invention cannot be sufficiently achieved, and if the amount added is too large, undesirable results may occur depending on the use of the quaternary ammonium hydroxide. . The aliphatic amines used in the present invention can be used alone or in combination. Quaternary ammonium hydroxide generally becomes colored over time after its production, and the degree of coloring increases over time. However, according to the method of the present invention, the progress of coloring over time can be prevented by adding an aliphatic amine. It can be prevented. Therefore, usually an aliphatic amine is added when producing quaternary ammonium hydroxide, but if there is no particular problem in the production method of quaternary ammonium hydroxide, quaternary ammonium hydroxide may be added. The aliphatic amine may be added immediately after the completion of the hydroxide synthesis reaction. Hereinafter, the effects of the present invention will be illustrated by examples. Examples 1 to 4 Ethylene oxide is added to monomethylamine to produce monomethyltriethanolammonium.
25% of hydroxide (hereinafter abbreviated as MTEA)
An aqueous solution was prepared, and 1 hour after the preparation, ethylenediamine was added to MTEA at 0.1, 0.5, 1.0 and 1 hour respectively.
3.0% by weight was added. These four types of MTEA aqueous solutions were allowed to stand at room temperature, and coloration over time was measured using the APHA color standard in accordance with JISK-6901. The measurement results are shown in Table 1. Comparative Example 1 The same 25% MTEA aqueous solution used in Example 1 was
The color change of APHA was measured when it was left as it was at room temperature. The measurement results are shown in Table 1.
Coloring rapidly progressed from the second day onwards. Comparative Examples 2 and 3 Silica sol (manufactured by Nissan Chemical Industries, Ltd., 30% as SiO 3 was added to the same 25% MTEA aqueous solution used in Example 1)
% content) was added to MTEA at 0.3% by weight and 1.0% by weight, respectively.
The MTEA aqueous solution was left at room temperature, and the change in color of APHA was measured. The measurement results are shown in Table 1.
【表】
実施例 ５〜８
実施例１〜４のMTEA水溶液を60℃の恒温槽
中で放置し、経時着色をAPHA色調基準により
測定した。測定結果は第２表に示す。
比較例 ４
実施例５〜８と同時に、エチレンジアミンを添
加しないMTEA溶液についても、同様にして経
時着色を測定した。結果は第２表に示す。[Table] Examples 5 to 8 The MTEA aqueous solutions of Examples 1 to 4 were left in a constant temperature bath at 60°C, and the coloration over time was measured using the APHA color standard. The measurement results are shown in Table 2. Comparative Example 4 Simultaneously with Examples 5 to 8, coloring over time was measured in the same manner for MTEA solutions to which ethylenediamine was not added. The results are shown in Table 2.
【表】
実施例 ９〜11
実施例１と同様の方法により、それぞれジメチ
ルジエタノールアンモニウム・ヒドロキシド
（DDEA）、トリメチルエタノールアンモニウ
ム・ヒドロキシド（TMEA）およびフエニルト
リメチルアンモニウム・ヒドロキシド（PTMA）
の25％水溶液を調製し、直ちにエチレンジアミン
をアンモニウム水酸化物に対し0.5重量％添加し
た。三種の試料につき、室温における経時着色を
APHA色調基準により測定した。測定結果は第
３表に示す。[Table] Examples 9 to 11 Dimethyldiethanolammonium hydroxide (DDEA), trimethylethanolammonium hydroxide (TMEA) and phenyltrimethylammonium hydroxide (PTMA) were prepared in the same manner as in Example 1, respectively.
A 25% aqueous solution was prepared, and 0.5% by weight of ethylenediamine was immediately added to the ammonium hydroxide. Coloring of three types of samples over time at room temperature
Measured by APHA color standard. The measurement results are shown in Table 3.
【表】
実施例 12〜15
実施例１と同様の方法で調製したMTEA25％
水溶液に、エチレンジアミンの代わりに脂肪族ア
ミンとして、それぞれトリエチレンテトラミン、
１，３―プロパンジアミン、ペンタエチレンヘキ
サミンおよびアミノエチルエタノールアミンを
MTEAに対し0.5重量％添加した試料を、室温で
放置して経時着色を測定した。測定結果は第４表
に示す。[Table] Examples 12-15 MTEA 25% prepared in the same manner as Example 1
In an aqueous solution, triethylenetetramine, aliphatic amine instead of ethylenediamine,
1,3-propanediamine, pentaethylenehexamine and aminoethylethanolamine
A sample containing 0.5% by weight of MTEA was left at room temperature and coloration over time was measured. The measurement results are shown in Table 4.
【表】【table】
Claims (1)
アミンを、第４級アンモニウム水酸化物に対し
0.01〜10重量％添加することを特徴とする、第４
級アンモニウム水酸化物の着色防止方法。 ２ 脂肪族アミンが一般式 H2N〔（CH2）nNH〕oＨ （ここでｍは２または３、ｎは１〜５）で表わ
される直鎖状ポリアミンである、特許請求の範囲
第１項に記載の方法。 ３ 脂肪族アミンがアミノアルコールアミンであ
る、特許請求の範囲第１項に記載の方法。[Claims] 1. An aliphatic amine having 2 to 8 amino groups in one molecule is added to a quaternary ammonium hydroxide.
The fourth, characterized in that 0.01 to 10% by weight is added.
Method for preventing coloration of class ammonium hydroxide. 2. Claim No. 2, wherein the aliphatic amine is a linear polyamine represented by the general formula H 2 N [(CH 2 ) n NH] o H (where m is 2 or 3, and n is 1 to 5). The method described in Section 1. 3. The method according to claim 1, wherein the aliphatic amine is an aminoalcohol amine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2194083A JPH0229068B2 (en) | 1983-02-12 | 1983-02-12 | DAI4KYUANMONIUMUSUISANKABUTSUNOCHAKUSHOKUBOSHIHOHO |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2194083A JPH0229068B2 (en) | 1983-02-12 | 1983-02-12 | DAI4KYUANMONIUMUSUISANKABUTSUNOCHAKUSHOKUBOSHIHOHO |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59148739A JPS59148739A (en) | 1984-08-25 |
| JPH0229068B2 true JPH0229068B2 (en) | 1990-06-27 |
Family
ID=12069040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2194083A Expired - Lifetime JPH0229068B2 (en) | 1983-02-12 | 1983-02-12 | DAI4KYUANMONIUMUSUISANKABUTSUNOCHAKUSHOKUBOSHIHOHO |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0229068B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI596080B (en) * | 2013-01-11 | 2017-08-21 | 沙琛公司 | Color forming inhibitor for quaternary ammonium hydroxide in non-aqueous solvent |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57171110U (en) * | 1981-04-22 | 1982-10-28 |
-
1983
- 1983-02-12 JP JP2194083A patent/JPH0229068B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59148739A (en) | 1984-08-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3264538D1 (en) | Polymeric ammonium compounds with a silica-like structure, process for producing them and their use | |
| KR870008791A (en) | Cerium oxide with new morphological properties and its preparation | |
| KR100286403B1 (en) | Production of triethylenediamine using surface ackdity deactivated zedlite catalysts | |
| JP3049602B2 (en) | Synthesis of triethylenediamine using base-treated zeolite as catalyst | |
| GB1486396A (en) | Polyamines for inhibiting the growth of algae | |
| JPH0229068B2 (en) | DAI4KYUANMONIUMUSUISANKABUTSUNOCHAKUSHOKUBOSHIHOHO | |
| KR860006463A (en) | Process for preparing 2-alkoxy-N- (1-azabicyclo [2,2,2] octan-3-yl) aminobenzamide | |
| US4709045A (en) | Process for producing 1,2-substituted imidazoline compounds | |
| JPH07502259A (en) | Diamine compounds, manufacturing methods, uses and intermediates | |
| JPS5843939A (en) | Mandelate and manufacture | |
| JPS59134752A (en) | Composition of quaternary ammonium hydroxide | |
| DE2615595B2 (en) | Process for the production of alkylene glycols | |
| US2248729A (en) | Quaternary allsylol poly-ammonium compounds and process for producing them | |
| CN112538024B (en) | Preparation method of hydroxyl tertiary amine hydrochloride crystal | |
| ES407914A1 (en) | Method of preparing stable aqueous solutions of organosilicic compounds and the resulting products and applications thereof | |
| US3992428A (en) | Process for preparing bis-(trimethylsilyl-)urea | |
| GB1256318A (en) | Alpha-hydroxy-carboxylic acid penta-coordinate silicon complexes | |
| EP4108297B1 (en) | Aqueous solution composition containing organosilicon compound | |
| NO150277B (en) | PROCEDURE FOR PREPARING LOW DIAMINE CONTENT OF IMIDAZOLINE COMPOUNDS | |
| US2851466A (en) | Substituted polyamines | |
| DE881659C (en) | Process for the preparation of polyalkylene polyamines | |
| KR900017907A (en) | Silica for Toothpaste Compositions Miscible with Organic Amino Compounds | |
| JPH02167274A (en) | Method for producing cyclic ether | |
| JPH03103318A (en) | Production of hydrophobic organocolloidal silica | |
| ES425131A1 (en) | Preparation of 2,5-disubstituted benzamides |