JPH0393789A - Production of stable organometallic compound - Google Patents
Production of stable organometallic compoundInfo
- Publication number
- JPH0393789A JPH0393789A JP23227989A JP23227989A JPH0393789A JP H0393789 A JPH0393789 A JP H0393789A JP 23227989 A JP23227989 A JP 23227989A JP 23227989 A JP23227989 A JP 23227989A JP H0393789 A JPH0393789 A JP H0393789A
- Authority
- JP
- Japan
- Prior art keywords
- organic solvent
- carboxylic acid
- added
- organic
- terpineol
- 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.)
- Pending
Links
- 150000002902 organometallic compounds Chemical class 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 20
- 239000012456 homogeneous solution Substances 0.000 claims abstract description 10
- KZVBBTZJMSWGTK-UHFFFAOYSA-N 1-[2-(2-butoxyethoxy)ethoxy]butane Chemical compound CCCCOCCOCCOCCCC KZVBBTZJMSWGTK-UHFFFAOYSA-N 0.000 claims abstract description 9
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 claims abstract description 9
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229940116411 terpineol Drugs 0.000 claims abstract description 9
- 239000000706 filtrate Substances 0.000 claims abstract description 8
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 8
- UODXCYZDMHPIJE-UHFFFAOYSA-N menthanol Chemical compound CC1CCC(C(C)(C)O)CC1 UODXCYZDMHPIJE-UHFFFAOYSA-N 0.000 claims description 8
- 150000002736 metal compounds Chemical class 0.000 claims description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 abstract description 13
- 239000002184 metal Substances 0.000 abstract description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 12
- 150000001735 carboxylic acids Chemical class 0.000 abstract description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract description 10
- 229910052697 platinum Inorganic materials 0.000 abstract description 5
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 abstract description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052737 gold Inorganic materials 0.000 abstract description 4
- 239000010931 gold Substances 0.000 abstract description 4
- 238000010992 reflux Methods 0.000 abstract description 4
- 229910052707 ruthenium Inorganic materials 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract description 2
- 238000001914 filtration Methods 0.000 abstract description 2
- 150000004820 halides Chemical class 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910000765 intermetallic Inorganic materials 0.000 abstract 2
- FRQQKWGDKVGLFI-UHFFFAOYSA-N 2-methylundecane-2-thiol Chemical compound CCCCCCCCCC(C)(C)S FRQQKWGDKVGLFI-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000007788 liquid Substances 0.000 description 12
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 5
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- 229910052703 rhodium Inorganic materials 0.000 description 4
- 239000010948 rhodium Substances 0.000 description 4
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 4
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 3
- 229910052787 antimony Inorganic materials 0.000 description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 3
- 229910052797 bismuth Inorganic materials 0.000 description 3
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- -1 oxides Chemical class 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 2
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 2
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 2
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000011133 lead Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910021555 Chromium Chloride Inorganic materials 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- QEZIKGQWAWNWIR-UHFFFAOYSA-N antimony(3+) antimony(5+) oxygen(2-) Chemical compound [O--].[O--].[O--].[O--].[Sb+3].[Sb+5] QEZIKGQWAWNWIR-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- JHXKRIRFYBPWGE-UHFFFAOYSA-K bismuth chloride Chemical compound Cl[Bi](Cl)Cl JHXKRIRFYBPWGE-UHFFFAOYSA-K 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- KZYDBKYFEURFNC-UHFFFAOYSA-N dioxorhodium Chemical compound O=[Rh]=O KZYDBKYFEURFNC-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- FDWREHZXQUYJFJ-UHFFFAOYSA-M gold monochloride Chemical compound [Cl-].[Au+] FDWREHZXQUYJFJ-UHFFFAOYSA-M 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- HTUMBQDCCIXGCV-UHFFFAOYSA-N lead oxide Chemical compound [O-2].[Pb+2] HTUMBQDCCIXGCV-UHFFFAOYSA-N 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、電子工業用材料や装飾用として用いられる金
属レジネートの改良方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a method for improving metal resinates used as materials for the electronic industry and for decoration.
（従来技術とその問題点）
従来法による白金、銀、パラジウム、イリジウム、ルテ
ニウム、ロジウム、金、銀、鉛、クロム、ビスマスおよ
びアンチモンの金属レジネートは遮光し室温下で保存し
ておいても徐々に分解し、１ヶ月程度の後に有機溶媒に
溶解させる際、完全に溶解しなくなるという欠点があっ
た。(Prior art and its problems) Metal resinates of platinum, silver, palladium, iridium, ruthenium, rhodium, gold, silver, lead, chromium, bismuth, and antimony produced by conventional methods gradually deteriorate even if they are protected from light and stored at room temperature. The problem is that when dissolved in an organic solvent after about one month, it does not dissolve completely.
各種の金属レジネートを有機バインダと有機溶媒で均一
な溶液としてセラミック等の基材に塗布、乾燥焼成して
金属の薄膜を形成させるための原料として、特に利用度
が高まっているが、上記のように有機溶媒に完全に溶解
しなくなると、均一な溶液とならないため、均一な薄膜
を形成させることができなくなり、濾過して使用するよ
うなことをした場合には金属分の分析をしなくては任意
の含有率に調製することができないという問題となり、
労力を要するため、長期保存のきく安定した有機金属化
合物が求められていた。Various metal resinates are increasingly being used as raw materials for forming thin metal films by applying a homogeneous solution of an organic binder and an organic solvent to a base material such as ceramics, drying and firing, and as mentioned above. If it is no longer completely dissolved in an organic solvent, it will not form a homogeneous solution, making it impossible to form a uniform thin film, and if it is used after filtration, it will not be necessary to analyze the metal content. The problem is that it is not possible to adjust the content to a desired content.
Since this method requires labor, there has been a need for stable organometallic compounds that can be stored for long periods of time.
（発明の目的）
本発明は、上記従来の金属レジネートの欠点を解決する
ために成されたもので、３ケ月以上安定した性状で保存
できる有機金属化合物の製造方法を提供するものである
。(Objective of the Invention) The present invention was accomplished in order to solve the above-mentioned drawbacks of the conventional metal resinates, and provides a method for producing an organometallic compound that can be stored with stable properties for three months or more.
（問題点を解決するための手段）
本発明は、金属化合物と有機カルボン酸またはメルカプ
タンを反応させたのち、有機溶媒を加えて濾過し、該濾
過液にターピネオール、メンタノールおよびジブチルカ
ルビトールのうち少なくとも１種を加えて均一な溶液と
したのち、前記有機溶媒を留去することを特徴とする安
定な有機金属化合物の製造方法である。(Means for Solving the Problems) The present invention involves reacting a metal compound with an organic carboxylic acid or a mercaptan, then adding an organic solvent to the filtrate, and adding at least one of terpineol, menthanol, and dibutylcarbitol to the filtrate. This is a method for producing a stable organometallic compound, which is characterized by adding one kind of organic solvent to form a uniform solution, and then distilling off the organic solvent.
金属化合物としては特に限定されないが、白金、銀、パ
ラジウム、イリジウム、ルテニウム、ロジウム、金、銀
、鉛、クロム、ビスマスおよびアンチモンの塩化物等の
ハロゲン化物、酸化物、水酸化物、硫化物、金属の無機
酸塩等を用いる。Metal compounds include, but are not particularly limited to, halides, oxides, hydroxides, sulfides such as chlorides of platinum, silver, palladium, iridium, ruthenium, rhodium, gold, silver, lead, chromium, bismuth, and antimony; Use inorganic acid salts of metals, etc.
また、有機カルボン酸としては、脂肪族カルボン酸、芳
香族カルボン酸、アビエチン酸の多核脂肪酸、アビエチ
ン酸を主成分とするガムロジン、ロジン誘導体等から選
択して用い、メルカプタンとしては、ｔｅｒｔ−ドデシ
ルメルカプタン、α−ピネンメル力ブタン等から選択し
て用いる。In addition, the organic carboxylic acid used is selected from aliphatic carboxylic acids, aromatic carboxylic acids, polynuclear fatty acids such as abietic acid, gum rosin whose main component is abietic acid, rosin derivatives, etc., and the mercaptan used is tert-dodecyl mercaptan. , α-pinene butane and the like.
金属化合物と有機カルボン酸またはメルカプタンを混合
して、反応温度は金属化合物と有機カルボン酸またはメ
ルカプタンの選択した種類により異なるが、２０〜２０
０℃で還流器付きの反応容器で攪拌しながら反応させる
。The metal compound and the organic carboxylic acid or mercaptan are mixed, and the reaction temperature varies depending on the selected types of the metal compound and the organic carboxylic acid or mercaptan.
The reaction is carried out at 0° C. with stirring in a reaction vessel equipped with a reflux device.
反応温度が１００℃以下の場合は湯浴中で加熱して反応
させ、１００℃以上の場合は油浴中で加熱して反応させ
ることが好ましい。When the reaction temperature is 100° C. or lower, it is preferable to heat the reaction in a water bath, and when the reaction temperature is 100° C. or higher, it is preferable to heat the reaction in an oil bath.
この理由は、反応時間に長時間かかりしかも安定した温
度で反応させる必要があるからである。The reason for this is that the reaction time is long and it is necessary to carry out the reaction at a stable temperature.
次いで、有機溶媒としてクロロホルム等を上記有機カル
ボン酸またはメルカプタンの加えた重量に対して３：ｌ
〜１：２の重量比を加えて攪拌したのち、濾過し、濾過
液にターピネオール、メンタノールおよびジブチルカル
ビトールのうち少なくとも１種を適量（金属レジネート
に対しての重量比でＩ：１〜３：１）加えて均一な溶液
としたのち、蒸留して有機溶媒を留去する。Next, chloroform or the like is added as an organic solvent at a ratio of 3:1 to the weight of the organic carboxylic acid or mercaptan added.
After adding and stirring at a weight ratio of ~1:2, it is filtered, and an appropriate amount of at least one of terpineol, menthanol, and dibutylcarbitol is added to the filtrate (in a weight ratio of I:1 to 3:1 to the metal resinate). 1) After adding it to make a homogeneous solution, distill it to remove the organic solvent.
該蒸留の終了は、有機溶媒の蒸留温度で操作し、もはや
蒸留液が留出しなくなった時とする。The distillation is terminated when the operation is performed at the distillation temperature of the organic solvent and no more distillate is distilled out.
以上の操作により溶液状の有機金属化合物が得られ、該
有機金属化合物は３ケ月以上の保存後でも均一で安定し
た溶液であり、金属の薄膜を形成するための原料として
、有機バインダとターピネオール、メンタノールおよび
ジブチルカルビトール等の有機溶剤と混合した場合にも
均一な溶液にになる。Through the above operations, an organometallic compound in the form of a solution is obtained, and the organometallic compound remains a uniform and stable solution even after storage for more than 3 months.As raw materials for forming a thin metal film, an organic binder, terpineol, It also forms a homogeneous solution when mixed with organic solvents such as menthanol and dibutylcarbitol.
以下、本発明に係る実施例を記載するが該実施例は本発
明を限定するものではない。Examples according to the present invention will be described below, but the examples are not intended to limit the present invention.
（実施例ｌ）
二酸化アンチモン（７２ｇ）とガム口ジン（７ ４．
８ ｇ’）を混合し、還流器付き反応容器に移し入れ
、油浴中１７０℃で４時間還流した。(Example 1) Antimony dioxide (72g) and Gumkou Jin (7.4.
8 g') were mixed, transferred to a reaction vessel equipped with a reflux condenser, and refluxed at 170° C. for 4 hours in an oil bath.
次いで、クロロホルムを２ ０ ０ｒｎｌを加えて攪拌
して、ＮＯ５Ｃ濾紙を用いて吸引濾過し、濾過液にター
ピネオール１０ｇを加えて攪拌したのち、蒸留装置付き
反応容器で加熱温度を６０℃としてクロロホルムを完全
に留去すると、黄褐色の液体（２５．６ｇ）が得られた
。Next, 200 rnl of chloroform was added and stirred, suction filtered using NO5C filter paper, 10 g of terpineol was added to the filtrate and stirred, and the chloroform was completely removed by heating at 60°C in a reaction vessel equipped with a distillation device. After evaporation, a tan liquid (25.6 g) was obtained.
この液体のアンチモン含有率を分析したところ８．０重
量％で、ターピネオール、メンタノールおよびジブチル
カルビトールの３種の有機溶剤にそれぞれ重量比ｌ：１
で混合させたところ、均一な溶液になった。When the antimony content of this liquid was analyzed, it was found to be 8.0% by weight.
When mixed, a homogeneous solution was obtained.
また、該黄褐色の液体を３ケ月間褐色瓶に入れ密栓して
暗所に室温で保存したのち、目視で外観観察したが、分
解物は観察されず、ターピネオール、メンタノールおよ
びジブチルカルビトールの３種の有機溶剤にそれぞれ重
量比ｌ：ｌで混合させたところ、均一な溶液になった。In addition, the yellowish brown liquid was placed in a brown bottle for 3 months, sealed tightly and stored at room temperature in a dark place, and then the appearance was visually observed, but no decomposition products were observed. When mixed with the respective organic solvents at a weight ratio of 1:1, a homogeneous solution was obtained.
（実施例２）
二酸化ロジウム（２０ｇ）とｔｅｒｔ−ドデシルメルカ
プタン（２０ｇ）を混合し、還流器付き反応容器に移し
入れ、室温で２４時間攪拌しながら反応させた。(Example 2) Rhodium dioxide (20 g) and tert-dodecyl mercaptan (20 g) were mixed, transferred to a reaction vessel equipped with a reflux device, and reacted with stirring at room temperature for 24 hours.
次いで、クロロホルムを３ ０ ０ｄを加えて攪拌して
、ＮＯ５Ｃ濾紙を用いて吸引濾過し、濾過液にジブチル
カルビトール５ｇを加えて攪拌したのち、蒸留装置付き
反応容器で加熱温度を６０℃としてクロロホルムを完全
に留去すると、褐色の液体（１５．３ｇ）が得られた。Next, 300 d of chloroform was added and stirred, suction filtered using NO5C filter paper, 5 g of dibutyl carbitol was added to the filtrate, and the mixture was stirred. When the residue was completely distilled off, a brown liquid (15.3 g) was obtained.
この液体のロジウム含有率を分析したところ１２．０重
量％で、タービネオール、メンタノールおよびジブチル
カルビトールの３種の有機溶剤にそれぞれ重量比ｌ：１
で混合させたところ、均一な溶液になった。Analysis of the rhodium content of this liquid revealed that it was 12.0% by weight, and it was found that the rhodium content in three organic solvents, turbineol, menthanol, and dibutyl carbitol, was mixed in a 1:1 weight ratio, respectively.
When mixed, a homogeneous solution was obtained.
また、該黄褐色の液体を３ケ月間褐色瓶に入れ密栓して
暗所に室温で保存したのち、目視で外観観察したが、分
解物は観察されず、ターピネオール、メンタノールおよ
びジブチルカルビトールの３種の有機溶剤にそれぞれ重
量比ｌ：ｌで混合させたところ、均一な溶液になった。In addition, the yellowish brown liquid was placed in a brown bottle for 3 months, sealed tightly and stored at room temperature in a dark place, and then the appearance was visually observed, but no decomposition products were observed. When mixed with the respective organic solvents at a weight ratio of 1:1, a homogeneous solution was obtained.
（実施例３）
金属化合物と有機カルボン酸またはメルカプタンを下記
の組み合わせで、表−１に示すそれぞれの反応温度と反
応時間で反応させ以下、クロロホルムの加えた量とター
ピネオール、メンタノールおよびジブチルカルビトール
の加えた量、蒸留温度、得られた液体の色および液体の
重量は下記の表−２に示す結果であった。(Example 3) The following combinations of metal compounds and organic carboxylic acids or mercaptans were reacted at the respective reaction temperatures and reaction times shown in Table 1. The amount added, distillation temperature, color of the liquid obtained, and weight of the liquid were as shown in Table 2 below.
ｌ．金属化合物と有機カルボン酸またはメルカプタンの
組み合わせ
■塩化白金（５０ｇ）とα−ピネンメルカプタン（５０
ｇ）
■塩化金（７０ｇ）と２−二チルヘキサン酸（１５０ｇ
）■塩化パラジウム（３０ｇ）とデカン酸（３２ｇ）■
塩化イリジウム（５０ｇ）と２−エチルヘキサン酸（７
７ｇ）
■塩化ルテニウム（５０ｇ）と２−エチルヘキサン酸（
３２ｇ）
■酸化鉛（１００ｇ）とガムロジン（１３５ｇ）■塩化
ビスマス（１５０ｇ）とガムロジン（９７ｇ）■塩化ク
ロム（５０ｇ）とガム口ジン（５２ｇ）■塩化銀（７０
ｇ）と２−エチルヘキサン酸（１５０ｇ）（以下余白）
２．反応温度と反応時間とＣＨＣｊ７．の加えた量表−
２
３．ターピネオール、メンタノールおよびジブチルカル
ビトール（以上の３種を「ＴＭＤ」とよぶ。l. Combination of metal compound and organic carboxylic acid or mercaptan■Platinum chloride (50g) and α-pinene mercaptan (50g)
g) ■Gold chloride (70g) and 2-ditylhexanoic acid (150g)
)■ Palladium chloride (30g) and decanoic acid (32g)■
Iridium chloride (50 g) and 2-ethylhexanoic acid (7
7g) ■Ruthenium chloride (50g) and 2-ethylhexanoic acid (
32g) ■Lead oxide (100g) and gum rosin (135g) ■Bismuth chloride (150g) and gum rosin (97g) ■Chromium chloride (50g) and gum rosin (52g) ■Silver chloride (70g)
g) and 2-ethylhexanoic acid (150g) (the following is the margin) 2. Reaction temperature, reaction time, and CHCj7. Table of amounts added to -
2 3. Terpineol, menthanol, and dibutylcarbitol (the above three types are referred to as "TMD").
）の加えた量、蒸留温度、得られた液体の色および液体
の重量。) added, distillation temperature, color of the liquid obtained and weight of the liquid.
（以下余白）
上記で得られた液体中の各金属成分の含有率を分析した
ところ、白金２０％、金４５％、パラジウム１４％、イ
リジウム１２％、ルテニウム２０％、鉛１５％、ビスマ
スｌＯ％、クロム５％、銀３０％であった。(Left below) Analysis of the content of each metal component in the liquid obtained above revealed 20% platinum, 45% gold, 14% palladium, 12% iridium, 20% ruthenium, 15% lead, and 10% bismuth. , 5% chromium, and 30% silver.
また、上記で得た液体を褐色瓶に密栓して暗所に３ケ月
保管した後、目視で外観確認したが沈澱物等はみられず
、タービネオール、メンタノールおよびジブチルカルビ
トール等を加えて溶解したところ、均一な溶液になった
。In addition, the liquid obtained above was sealed in a brown bottle and stored in a dark place for 3 months, and the appearance was visually checked, but no precipitates were observed, and turbineol, menthanol, dibutylcarbitol, etc. were added and dissolved. However, the solution became homogeneous.
（発明の効果）
本発明は、従来法による金属レジネートは保存中に分解
して、一部分がクロロホルム等の有機溶媒に溶解しなく
なる欠点を、金属レジネートの製造方法の改良によりタ
ーピネオール、メンタノールおよびジブチルカルビトー
ルの少なくともｌ種を加えて、他の有機溶媒を蒸留分離
することと、液状として保存することで、目的とする３
ケ月以上の保存が可能となったことは、有機金属化合物
の利用範囲を広めることと、薄膜形成技術の信頼性向上
等にも大いに貢献するものである。(Effects of the Invention) The present invention solves the disadvantage that metal resinates produced by conventional methods decompose during storage and become partially insoluble in organic solvents such as chloroform, and by improving the production method of metal resinates, terpineol, menthanol and dibutyl carbide are used. The objective 3
The fact that it can be stored for more than several months will greatly contribute to expanding the scope of use of organometallic compounds and improving the reliability of thin film formation technology.
Claims (1)
を反応させたのち、有機溶媒を加えて濾過し、該濾過液
にターピネオール、メンタノールおよびジブチルカルビ
トールのうち少なくとも１種を加えて均一な溶液とした
のち、前記有機溶媒を留去することを特徴とする安定な
有機金属化合物の製造方法。(1) After reacting a metal compound with an organic carboxylic acid or mercaptan, an organic solvent is added and filtered, and at least one of terpineol, menthanol, and dibutylcarbitol is added to the filtrate to make a homogeneous solution. , a method for producing a stable organometallic compound, which comprises distilling off the organic solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23227989A JPH0393789A (en) | 1989-09-07 | 1989-09-07 | Production of stable organometallic compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23227989A JPH0393789A (en) | 1989-09-07 | 1989-09-07 | Production of stable organometallic compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0393789A true JPH0393789A (en) | 1991-04-18 |
Family
ID=16936742
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23227989A Pending JPH0393789A (en) | 1989-09-07 | 1989-09-07 | Production of stable organometallic compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0393789A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100491454B1 (en) * | 1996-03-19 | 2005-09-26 | 크롬프톤 게엠베하 | Preparation of Homogeneous Mixture Containing Metalorganic Compound |
-
1989
- 1989-09-07 JP JP23227989A patent/JPH0393789A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100491454B1 (en) * | 1996-03-19 | 2005-09-26 | 크롬프톤 게엠베하 | Preparation of Homogeneous Mixture Containing Metalorganic Compound |
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