CN1629123A - Use of 1-methyl-4-isopropyl-bicyclo[2,2,2] octane-2,3-dicarboxylic acid - Google Patents
Use of 1-methyl-4-isopropyl-bicyclo[2,2,2] octane-2,3-dicarboxylic acid Download PDFInfo
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- CN1629123A CN1629123A CN 200410043929 CN200410043929A CN1629123A CN 1629123 A CN1629123 A CN 1629123A CN 200410043929 CN200410043929 CN 200410043929 CN 200410043929 A CN200410043929 A CN 200410043929A CN 1629123 A CN1629123 A CN 1629123A
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Abstract
The invention discloses the novel use of 1-methyl-4-isopropyl-bicyclo[2,2,2] octane-2,3-dicarboxylic acid, and provides a ring form monoterpene derivative than can be used as novel welding agent, the active constituent of the novel welding agent is prepared from alpha-terpinene and maleic anhydride as raw material through intermolecular Diels-Alder ring additive reaction, then hydrogenation and watering decomposition are carried out to obtain the bicyclic monoterpene derivatives with dicarboxilic acid functional group as the characteristic construction.
Description
Technical field:
The present invention relates to a kind of 1-methyl-4-sec.-propyl-two ring [2,2,2] octane-2, the 3-dicarboxylic acid is as novel welding compound, is used for the new purposes in the middle of the electronic product production process needs the weldprocedure of soldering of electronic components.
Background technology:
For electronic component is fixed on the circuit card, welding compound is indispensable in the middle of the electronic product production process.Rosin (Rosin) is well-known welding compound commonly used.The shortcoming that rosiny is very big is to leave a large amount of residues easily after the welding, these residues not only cause conduction bad but also become the inspection obstacle in the automatization checking process, must remove away residue for this reason, the reason people have taked the stronger halogen solvent of scourability thus, but, the halogen solvent to environment damage by conditional use.In addition, in welding process, heating is absolutely necessary, and the high-accuracy electronic component that highly dense is arranged imposes high temperature and can damage electronic component undoubtedly, carries out at a lower temperature so wish welding.At computer and a large amount of popularize present of domestic electronic appliances; since to the raising of environmental protection consciousness, the small-sized microminiaturization of electronic product, the raising that the production automation requires; seek low cost; nuisanceless, low residue, easily washing; high reactivity; low welding temperature, energy-conservation, the welding compound of few additive is still the important topic of current research exploitation.Show and suggestion, rosin can not satisfy these above-mentioned requirements, and in order to improve these shortcomings of rosiny, various welding compound modification methods have been suggested.For example, spy about the washing composition exploitation opens flat 6-340896, open flat 8-118068 about the spy who in welding compound, adds antioxidant, about opening flat 9-70689 for improving welding activity interpolation organic acid spy in rosin, open flat 2001-114747 about adding water miscible synthetic nitrogenous compound as the spy of promoting agent, open flat 2001-232495 etc. about the spy who adds the amido halogen compound as promoting agent.Though all improve to some extent,, make the welding compound composition increase, to form complicatedly, cost improves, and perhaps the additive complex structure synthesizes problems such as difficulty.China has abundant terpene resource, yet and terpenoid is from from harmless natural non-harmful product, the new purposes of therefore developing terpenoid all has very important meaning to effectively utilizing China's terpene resource and protection environment.
Summary of the invention:
The invention provides a kind of with low cost, synthetic, nuisanceless easily, high reactivity, low temperature, the easily novel welding compound that is used for the electronic component welding of washing, it is 1-methyl-4-sec.-propyl-two ring [2,2,2] octane-2, the 3-dicarboxylic acid, synthesized 1-methyl-4-sec.-propyl-two ring [2,2,2] octane-2, the 3-dicarboxylic acid, and find that it has the new purposes of welding function.
The present inventor finds 1-methyl-4-sec.-propyl-two ring [2 in the middle of the process of research monoterpene purposes, 2,2] octane-2, the 3-dicarboxylic acid has the welding function, it is active to have a very high welding as the welding compound of electronic component, can be applied to in the weldprocedure of scolding tin soldering of electronic components on circuit card etc. and in the middle of the various electronic product production process that needs soldering of electronic components.
In order to prepare this novel welding compound, be raw material at first with α-terpinene and maleic anhydride, under heating condition, carry out intermolecular Di Ersi-Alder (Diels-Alder) cycloaddition reaction, at first obtained 1-methyl-4-sec.-propyl-two ring [2,2,2] octene-1,2-dicarboxylic anhydride cycloaddition product, then, be that catalyzer carries out hydrogenation with nickel again, adding water decomposition with alkalescence has at last obtained to have the 1-methyl that dicarboxylic acid functional group is the bicyclic diterpene analog derivative of feature structure-4-sec.-propyl-two ring [2,2,2] octane-2, the 3-dicarboxylic acid, infrared spectra and determined structure with nucleus magnetic resonance.
Follow the method for Japanese JIS-Z-3197 regulation, inquiring into 1-methyl-4-sec.-propyl-two ring [2,2,2] octane-2, whether the 3-dicarboxylic acid has in the active test of welding, has found that it has the welding function, and also has very high welding activity.
According to result of the present invention, welding temperature is carried out under 200-220 ℃ of lesser temps, still has very high welding activity, can effectively prevent because high welding temperature causes the damage of electronic component.The welding residue few and with environmental sound such as limonene, the monoterpene class of firpene etc. is easy to clean as solvent, does not need to use environmentally harmful halogen washing composition.This novel welding compound is easily synthetic, and is with low cost, is a kind of nuisanceless, high reactivity, and welding temperature is low, and residue is few, easily the novel welding compound of washing.The present invention attempts this monoterpene derivative is applied to electronic applications first, for the electronic component weldprocedure in the electronic applications provides a kind of new comparatively ideal very promising novel welding compound is arranged, thereby has finished this invention.
Embodiment:
Novel welding compound activeconstituents 1-methyl-4-sec.-propyl-two ring [2,2,2] octane-2, the method for making of 3-dicarboxylic acid
Of the present invention provide with 1-methyl-4-sec.-propyl-two ring [2,2,2] octane-2, the 3-dicarboxylic acid is that the novel welding compound of activeconstituents is can be by the method preparation of following formula.
Embodiment is: with α-terpinene and maleic anhydride is raw material, under heating condition, after maleic anhydride drips α-terpinene, under same temperature, carry out intermolecular Di Ersi-Alder (Diels-Alder) cycloaddition reaction and at first obtain 1-methyl-4-sec.-propyl-two ring [2,2,2] octene-2,3-dicarboxylic anhydride cycloaddition product, then, in methanol solvate, be that catalyzer carries out hydrogenation reaction with Raney nickel, obtained 1-methyl-4-sec.-propyl-two ring [2,2,2] octane-2, the 3-dicarboxylic anhydride, then, add water decomposition with potassium hydroxide aqueous solution and obtained object 1-methyl-4-sec.-propyl-two ring [2,2,2] octane-2, the 3-dicarboxylic acid, its constitutional features is the bicyclic diterpene analog derivative with dicarboxylic acid functional group, determines structure with infrared spectra with mr, welds activity test as welding compound.
The welding activity test
The method of Japanese JIS-Z-3197 regulation is followed in the welding activity test, measures the sheetage of scolding tin when using novel welding compound on copper coin, with primary standard rosin relatively, the big more welding activity of sheetage is big more.For relatively, also measured toxilic acid simultaneously, maleic anhydride and α-terpinene mixture the results are shown in table 1.Maleic anhydride, under the situation of toxilic acid and α-terpinene mixture, although sample all volatilizees,, the melting solder phenomenon does not take place in scolding tin, just toxilic acid or maleic anhydride and not welding activity of α-terpinene mixture are described, and 1-methyl-4-sec.-propyl-two ring [2,2,2] octane-2, the 3-dicarboxylic acid has then shown very high welding activity, and sheetage is higher than comparison material rosin far away.
Embodiment 1 (1-methyl-4-sec.-propyl-two ring [2,2,2] octene-2, the preparation of 3-dicarboxylic anhydride)
By thermometer being housed, dropping funnel, mechanical stirrer, in the four-hole boiling flask of prolong, add maleic anhydride (being calculated as 2.5 times of moles) and heating and make the maleic anhydride dissolving, be controlled under 65-70 ℃ with α-terpinene, from dropping funnel drip the terpinene mixture (α-terpinene oil length 32.4%, γ-Song Youxi 15.6%, different-terpinolene 14.6%, terpinolene 6.9%, kautschin 5.1%, amphene 4.5%, beta-pinene 3.5%, α-Pai Xi 3.4%, to the Meng-3,8-diene 1.9%).135-140 ℃ of reaction down, distillation is removed low boiling component and is obtained crude product after dripping off, and cut promptly gets product 1-methyl-4-sec.-propyl-two ring [2 under the 160-170 ℃/3mmHg of underpressure distillation collection, 2,2] octene-2, the 3-dicarboxylic anhydride is determined structure with infrared spectra and nucleus magnetic resonance.
Embodiment 2 (hydrogenation reaction)
The embodiment 1 synthetic distillage 1-methyl-4-sec.-propyl-two of using of 20g is encircled [2,2,2] octene-2, after the 3-dicarboxylic anhydride is dissolved into 50ml methyl alcohol, this methanol solution is placed autoclave, take by weighing the Raney nickel catalyzator (Raney NiW2) of 1.0g then, to neutrality, add reactor to methanol wash.Behind air in the hydrogen exchange still, hydrogen is filled to 3MPa, under 100 ℃, start agitator, the adjustment stirring velocity is 500rpm, the reaction beginning, reactant begins to absorb hydrogen, and hydrogen pressure descends.Hydrogen make-up is to 3MPa when hydrogen pressure drops to 0.1MPa, and this operation repeatedly is over through 40 hours afterreactions.After removing catalyzer with filtration adjuvant decompression, boil off solvent with rotatory evaporator and get thick hydrogenation products, get high-purity product 1-methyl-4-sec.-propyl-two with the normal hexane recrystallization of 2 times of amounts and encircle [2,2,2] octane-2,3-dicarboxylic anhydride.
Embodiment 3 (adding the water decomposition reaction)
Hydrogenation products 1-methyl-4-sec.-propyl-two that embodiment 2 is obtained encircles [2,2,2] octane-2, the 3-dicarboxylic anhydride slowly joins in the excessive 6M aqueous sodium hydroxide solution and stirs, with removing insolubles after the chloromethane extracting twice, aqueous layer neutralizes with the aqueous sulfuric acid of 3N, crystal is separated out, and filtration under diminished pressure obtains white crystals and adds water decomposition product 1-methyl-4-sec.-propyl-two ring [2,2,2] octane-2, the 3-dicarboxylic acid, is used infrared spectra by mp 133.5-134.8 ℃, nucleus magnetic resonance is determined structure, and A is used for welding test as welding compound.
Embodiment 4 (welding determination of activity)
The method of Japanese JIS-Z-3197 regulation is followed in the welding activity test, uses the H60A type, and diameter is the scolding tin of 1.6mm, and rosin is measured for comparing material.
20mm*20mm*0.3mm copper coin clean the back 150 ℃ of following heated oxides 1 hour with Virahol.Taking by weighing 0.250mg ± 0.01 scolding tin is rolled into the circle shape and is put on the copper coin, put the welding compound sample that to measure at circular scolding tin center, example weight is 25mg ± 5, and above-mentioned copper coin is placed on the hot-plate, controls 4 minutes and is heated to 200 ℃, cut off the electricity supply, with for example limonene, the monoterpene class of firpene etc. is measured solder thickness and diameter after launching as the solvent wash copper coin after the cooling, with the sheetage of following formula calculating scolding tin, the sheetage value is big more to mean that the activity of welding compound is high more.
Sheetage (%)=(D-H)/D*100%, D is the diameter (mm) when scolding tin is regarded as sphere, H is the height (mm) of unfolded scolding tin.
The experiment results
| Welding compound | Sheetage (%) | With limonene solvent wash result |
| Toxilic acid | Scolding tin not fusion launches | - |
| Toxilic acid and α-terpinene mixture | Scolding tin not fusion launches | - |
| Rosin | 82.5 | Washing can not, residue is residual |
| A | 90.0 | Easily |
Claims (3)
1. monoterpene derivative 1-methyl-4-sec.-propyl-two ring [2 that has following structure, 2,2] octane-2, the new purposes of 3-dicarboxylic acid is characterized in that: 1-methyl-4-sec.-propyl-two ring [2,2,2] octane-2, the 3-dicarboxylic acid has the welding function, and very high welding activity is arranged, and can be applied to scolding tin on circuit card in the weldprocedure during soldering of electronic components and in the middle of the various electronic product production process that needs soldering of electronic components as novel welding compound.
2. the methyl of the 1-described in the claim 1-4-sec.-propyl-two encircles [2,2,2] octane-2, the new purposes of 3-dicarboxylic acid, as novel welding compound, it is characterized in that: in order to prepare this novel welding machine, be to be the raw material that sets out with α-terpinene or the terpinene mixture and the maleic anhydride that contain 30 left and right sides α-terpinenes, under heating condition, carry out intermolecular Di Ersi-Alder (Diels-Alder) cycloaddition reaction, at first obtain 1-methyl-4-sec.-propyl-two ring [2,2,2] octene-2,3-dicarboxylic anhydride cycloaddition product, use Raney nickel as catalyzer then, in methanol solvate, under 100 ℃ and 0.5-5MPa pressure, carry out hydrogenation, carry out alkalescence with excessive aqueous sodium hydroxide solution at last and add water decomposition, then the white crystals that obtains with the concentrated hydrochloric acid acidifying.
3. the methyl of the 1-described in the claim 1-4-sec.-propyl-two encircles [2,2,2] octane-2, the new purposes of 3-dicarboxylic acid, as novel welding compound, it is characterized in that: 1-methyl-4-sec.-propyl-two of being produced by aforesaid method encircles [2,2,2] octane-2, the 3-dicarboxylic acid is to have the saturated bicyclic monoterpenes derivative that ortho position dicarboxylic acid functional group is a feature structure for the novel welding compound of welding activeconstituents.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100439299A CN100338009C (en) | 2004-10-12 | 2004-10-12 | Use of 1-methyl-4-isopropyl-bicyclo[2,2,2] octane-2,3-dicarboxylic acid |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100439299A CN100338009C (en) | 2004-10-12 | 2004-10-12 | Use of 1-methyl-4-isopropyl-bicyclo[2,2,2] octane-2,3-dicarboxylic acid |
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| Publication Number | Publication Date |
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| CN1629123A true CN1629123A (en) | 2005-06-22 |
| CN100338009C CN100338009C (en) | 2007-09-19 |
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| CNB2004100439299A Expired - Fee Related CN100338009C (en) | 2004-10-12 | 2004-10-12 | Use of 1-methyl-4-isopropyl-bicyclo[2,2,2] octane-2,3-dicarboxylic acid |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04270096A (en) * | 1991-02-20 | 1992-09-25 | Iwatsu Electric Co Ltd | Cream solder |
| JPH04318023A (en) * | 1991-04-15 | 1992-11-09 | Denki Kagaku Kogyo Kk | Epoxy resin composition |
| JP3722501B2 (en) * | 1994-09-19 | 2005-11-30 | 日本テルペン化学株式会社 | Soldering flux |
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Granted publication date: 20070919 Termination date: 20101012 |