CN1593839A - Novel purpose of 4-(4-methyl-n-amyl)-cyclohexane-1,2-dicarboxylic acid - Google Patents
Novel purpose of 4-(4-methyl-n-amyl)-cyclohexane-1,2-dicarboxylic acid Download PDFInfo
- Publication number
- CN1593839A CN1593839A CN 200410043661 CN200410043661A CN1593839A CN 1593839 A CN1593839 A CN 1593839A CN 200410043661 CN200410043661 CN 200410043661 CN 200410043661 A CN200410043661 A CN 200410043661A CN 1593839 A CN1593839 A CN 1593839A
- Authority
- CN
- China
- Prior art keywords
- welding
- methyl
- pentyl
- cyclohexane
- dicarboxylic acids
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to an annular monoterpene derivative used as new bonding glue. The annular monoterpene derivative 4-4- cyclohexane -1,2- dicarboxylic acid can bond the electric unit on the copperplate, and has high active welding property, leaves little draff, needs only low temperature, and is easy to wash. The active component is annular monoterpene derivative that has dicarboxylic acid anhydride, and is made from Beta-myrcene and maleic anhydride first through Diels-Alder molecule cycloaddition reaction, and then being decomposed by water. It can be used for welding the electric units on circuit board with soldering tin and production of other electric unit needing bonding electric unit.
Description
Technical field: the present invention relates to a kind of 4-(4-methyl n-pentyl)-cyclohexane-1, the 2-dicarboxylic acids is as novel welding compound, is used for the new purposes in the middle of the electronic product production process needs the welding procedure of soldering of electronic components.
Background technology: for electronic component is fixed on the circuit board, welding compound is indispensable in the middle of the electronic product production process.Rosin (Rosin) is well-known welding compound commonly used.The very big shortcoming of rosin 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 automation checking process, must remove away residue, 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 activity; 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 rosin, various welding compound modification methods have been suggested.For example, spy about the washing agent 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 nitrogen-containing compound as the spy of activating agent, open flat 2001-232495 etc. about the spy who adds the amido halogen compound as activating 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.On the other hand, up to now, relevant monoterpene derivative 4-(4-methyl n-pentyl)-cyclohexane-1, the purposes of 2-dicarboxylic acids yet there are no report.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 easily, nuisanceless, high activity, low temperature, the novel welding compound that is used for the electronic component welding that easily washs, be 4-(4-methyl n-pentyl)-cyclohexane-1, the 2-dicarboxylic acids has synthesized 4-(4-methyl n-pentyl)-cyclohexane-1, the 2-dicarboxylic acids, and find that it has the new purposes of welding function.
The present inventor finds 4-(4-methyl n-pentyl)-cyclohexane-1 in the middle of the process of research monoterpene purposes, the 2-dicarboxylic acids has the welding function, it is active to have a higher welding as the welding compound of electronic component, can be applied to in the welding procedure of scolding tin soldering of electronic components on circuit board etc. and in the middle of the various electronic product production process that needs soldering of electronic components.
Be raw material at first with beta-myrcene and maleic anhydride, under heating condition, carry out intermolecular Di Ersi-Alder (Diels-Alder) cycloaddition reaction, at first obtained 4-(4-methyl-3-pentenyl)-4-cyclohexene-1,2-anhydride rings addition compound product, then, carry out hydrogenation again, add water decomposition at last and obtained to have the 4-that dicarboxylic acids functional group is the ring-type monoterpenes derivative of feature structure (4-methyl n-pentyl)-cyclohexane-1, the 2-dicarboxylic acids has been determined structure with nulcear magnetic resonance (NMR).
Follow the method for Japanese JIS-Z-3197 regulation, in the test whether the welding activity is arranged of inquiring into it, found that it has the welding function, and also has very high welding activity, not only can be used as welding compound and use separately, also can be used as the welding compound active component and add mixing use in other welding compounds to.
According to result of the present invention, welding temperature is carried out under 200-220 ℃ of lower temperature, 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 citrene, the monoterpene class of firpene etc. is easy to clean as solvent, does not need to use environmentally harmful halogen washing agent.This novel welding compound is easily synthetic, and is with low cost, is a kind of nuisanceless, high activity, and welding temperature is low, and residue is few, easily the very promising novel welding compound of washing.
The present invention attempts this monoterpene derivative is applied to electronic applications first, for the electronic component welding procedure 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 active component 4-(4-methyl n-pentyl)-cyclohexane-1, the method for making of 2-dicarboxylic acids
Of the present invention provide with 4-(4-methyl n-pentyl)-cyclohexane-1, the 2-dicarboxylic acids is that the novel welding compound of active component is by the preparation of the method for following formula.
4-(4-methyl n-pentyl)-cyclohexane-1, the 2-dicarboxylic acids
Concrete preparation method is: with beta-myrcene and maleic anhydride is raw material, under heating condition, after maleic anhydride drips beta-myrcene, under same temperature, carry out intermolecular Di Ersi-Alder (Diels-Alder) cycloaddition reaction and at first obtain 4-(4-methyl-3-pentenyl)-4-cyclohexene-1,2-dicarboxylic anhydride cycloaddition product then, is dissolved in it in the ethyl acetate, with 5%Pd/C is catalyst, at room temperature and 1-5kg/cm
2Carry out hydrogenation reaction under the hydrogen pressure and obtain hydrogenation products 4-(4-methyl n-pentyl)-cyclohexane-1, the 2-dicarboxylic anhydride, add water decomposition at last and obtain object 4-(4-methyl n-pentyl)-cyclohexane-1, the 2-dicarboxylic acids, its architectural feature is the ring-type monoterpenes derivative with dicarboxylic acids functional group, welds activity test as welding compound.Also can be to cycloaddition product 4-(4-methyl n-pentyl)-cyclohexene-1, the 2-dicarboxylic anhydride adds after the water decomposition repeated hydrogenation earlier and reacts and prepare.
In addition, the beta-myrcene of raw material is important spices, also is the basic material of synthetic perfume, and it can be easy to a large amount of preparations from the nopinene of one of turpentine oil main component.
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 substance rosin relatively, the big more welding activity of sheetage is big more.For relatively, also measured maleic acid simultaneously, maleic anhydride and beta-myrcene mixture the results are shown in table 1.Maleic anhydride, under the situation of maleic acid and beta-myrcene mixture, although sample all volatilizees, but, the fusion weld phenomenon does not take place in scolding tin, just maleic acid or maleic anhydride and not welding activity of beta-myrcene mixture are described, dicarboxylic acid compound has then shown very high welding activity, and sheetage is higher than comparison material rosin far away.So this novel welding compound not only can be used as welding compound and uses separately, also can be used as the welding compound active component and add mixing use in other welding compound to.
Embodiment 1 (raw material 4-(4-methyl-3-pentenyl)-4-cyclohexene-1, the preparation of 2-dicarboxylic anhydride)
By thermometer being housed, dropping funel, mechanical agitator, in the four-hole boiling flask of condenser pipe, add maleic anhydride (being calculated as 1.0 times of moles) and heating and make the maleic anhydride dissolving, be controlled under 65-70 ℃, drip beta-myrcene (beta-myrcene contains rate 75%) from dropping funel with beta-myrcene.Dripping off the back reacted 4 hours under same temperature.Cut promptly gets cycloaddition product 4-(4-methyl-3-pentenyl)-4-cyclohexene-1 under the 155-160 ℃/3mmHg of decompression distillation collection, and the 2-dicarboxylic anhydride is determined structure with infrared spectrum and nulcear magnetic resonance (NMR).
Embodiment 2 (hydrogenation reaction)
Cycloaddition product 4-(4-methyl-3-pentenyl)-4-cyclohexene-1 that embodiment 1 is obtained, 2-dicarboxylic anhydride 32g is dissolved in the 97ml ethyl acetate, this ethyl acetate solution is joined in the autoclave, and the 5%Pd/C catalyst that takes by weighing 1.6g then adds reactor to.Get with hydrogen and to change in the still behind the air, hydrogen is filled to 5kg/cm
2After start blender to adjust mixing speed be 500rpm, reaction begins immediately, reactant begins to absorb hydrogen, Hydrogen Vapor Pressure descends.When Hydrogen Vapor Pressure drops to 1kg/cm
2The time hydrogen make-up to 5kg/cm
2, this operation repeatedly.After suction hydrogen stops, after removing catalyst with filtration adjuvant, boil off solvent with rotary evaporator and get thick hydrogenation products, decompression distillation collects that cut promptly gets hydrogenation products 4-(4-methyl n-pentyl)-cyclohexane-1 under the 160-165 ℃/1mmHg, the 2-dicarboxylic anhydride is determined structure with nulcear magnetic resonance (NMR).
Embodiment 3 (adding the water decomposition reaction)
Decompression distillation hydrogenation products 4-(4-methyl n-pentyl)-cyclohexane-1 that embodiment 2 is obtained, the 2-dicarboxylic anhydride slowly joins in the excessive 6M sodium hydrate aqueous solution and stirs, with removing insoluble matter after the chloromethane extracting twice, aqueous layer neutralizes with the aqueous sulfuric acid of 3N, and crystal is separated out, and filtration under diminished pressure obtains white crystals and adds water decomposition product 4-(4-methyl n-pentyl)-cyclohexane-1, the 2-dicarboxylic acids, use infrared spectrum, nulcear magnetic resonance (NMR) is determined structure, and A is used for soldering 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 isopropyl alcohol.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 heating plate, controls 4 minutes and is heated to 200 ℃, cut off the electricity supply, with for example citrene, the monoterpene class of firpene etc. is removed as the solvent wash copper coin after the cooling, measures solder thickness and diameter after launching, 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 the scolding tin of expansion.
The experiment results
| Welding compound | Sheetage (%) | Use the solvent wash result |
| Maleic acid | Scolding tin not fusion launches | |
| Maleic acid+beta-myrcene | Scolding tin not fusion launches | |
| Rosin | 82.5 | Washing can not, residue is residual |
| A (adding the water decomposition product) | 92.0 | Easily |
Claims (3)
1. monoterpene derivative 4-(4-methyl the n-pentyl)-cyclohexane-1 that has following structure, the new purposes of 2-dicarboxylic acids, it is characterized in that: 4-(4-methyl n-pentyl)-cyclohexane-1, the 2-dicarboxylic acids has the welding function, and very high welding activity is arranged, can be applied to scolding tin on circuit board in the welding procedure 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 4-described in the claim 1 (4-methyl n-pentyl)-cyclohexane-1, the new purposes of 2-dicarboxylic acids, as novel welding compound, it is characterized in that: be to be raw material by beta-myrcene and maleic anhydride, under heating condition, carry out intermolecular Di Ersi-Alder (Diels-Alder) cycloaddition reaction, at first obtain 4-(4-methyl n-pentyl)-cyclohexene-1,2-dicarboxylic anhydride cycloaddition product, then, carry out hydrogenation, add at last that water decomposition obtains to have the ring-type monoterpenes derivative that dicarboxylic acids functional group is a feature structure.Also can be to 4-(4-methyl n-pentyl)-cyclohexene-1,2-dicarboxylic anhydride cycloaddition product adds earlier and carries out hydrogenation reaction again after the water decomposition and prepare.
3. the 4-described in the claim 1 (4-methyl n-pentyl)-cyclohexane-1, the new purposes of 2-dicarboxylic acids, as novel welding compound, it is characterized in that: not only can be used as welding compound and use separately, also can be used as the welding compound active component and add mixing use in other welding compounds to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410043661 CN1593839A (en) | 2004-06-30 | 2004-06-30 | Novel purpose of 4-(4-methyl-n-amyl)-cyclohexane-1,2-dicarboxylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410043661 CN1593839A (en) | 2004-06-30 | 2004-06-30 | Novel purpose of 4-(4-methyl-n-amyl)-cyclohexane-1,2-dicarboxylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1593839A true CN1593839A (en) | 2005-03-16 |
Family
ID=34665368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200410043661 Pending CN1593839A (en) | 2004-06-30 | 2004-06-30 | Novel purpose of 4-(4-methyl-n-amyl)-cyclohexane-1,2-dicarboxylic acid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1593839A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101454116B (en) * | 2006-05-31 | 2013-06-12 | 英特尔公司 | Solder flux composition |
-
2004
- 2004-06-30 CN CN 200410043661 patent/CN1593839A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101454116B (en) * | 2006-05-31 | 2013-06-12 | 英特尔公司 | Solder flux composition |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Hsiao et al. | Ultrasonic mixing and closed microwave irradiation-assisted transesterification of soybean oil | |
| Xiong et al. | Solid alcohol based on waste cooking oil: Synthesis, properties, micromorphology and simultaneous synthesis of biodiesel | |
| CN1593839A (en) | Novel purpose of 4-(4-methyl-n-amyl)-cyclohexane-1,2-dicarboxylic acid | |
| CN101942007A (en) | Method for extracting phytosterol from waste residues generated in biodiesel production and product thereof | |
| CN111909781A (en) | Method for extracting free fatty acid from crude vegetable oil | |
| Eliel et al. | Conformational Analysis. VIII. The Conformational Equilibrium Constant of the Carbethoxyl Group1 | |
| CN1593838A (en) | Novel purpose of 4-(4-methyl-3-pentenyl)-4-cyclohexene-1, 2-dicarboxylic acid | |
| CN1597235A (en) | New use of 4-(4-mothyl-n-amyl) cyclohexane-1,2-diacid anhydride | |
| CN110963889B (en) | Method for synthesizing left-optical-activity citronellol by asymmetric hydrosilylation of citral | |
| CN1308114C (en) | Use of 1-methyl-4-isopropyl-bicyclic [2,2,2] octene-2,3-dicarboxylic acid | |
| JPWO2008023728A1 (en) | Method for producing fatty acid ester from vegetable oil and diesel fuel containing the fatty acid ester | |
| CN1593837A (en) | Novel purpose of 4-(4-methyl-3-pentenyl)-4-cyclohexene-1, 2-diacid anhydride | |
| CN100338009C (en) | Use of 1-methyl-4-isopropyl-bicyclo[2,2,2] octane-2,3-dicarboxylic acid | |
| CN104646058B (en) | Copper-containing complex catalyst and preparation method and application thereof | |
| TW201202414A (en) | Detergent composition for removing polyimide | |
| CN1629152A (en) | Use of 1-methyl-4-isopropyl-bicyclo[2,2,2] octane-2,3-diacid anhydride | |
| JP6933971B2 (en) | Downstream treatment of aliphatic alcohol compositions produced by recombinant host cells | |
| CN108893747A (en) | A kind of plane lapping cleaning agent and its preparation method | |
| CN104610053A (en) | Rosin derivate for soldering flux and preparation method | |
| Shobana et al. | Kinetics and characterization of transesterification of cottonseed oil to biodiesel using calcined clam shells as catalyst | |
| KR101563954B1 (en) | Solder flux and solder paste | |
| CN107628927B (en) | Method for synthesizing alpha-terpineol from limonene | |
| Cotton et al. | Novel products in the carbonylation of the triply bonded ditungsten hexaisopropoxide dipyridine adduct. 2. Preparation and structure of tetracarbonylhexakis (isopropanolato) ditungsten (W2 (O-iso-Pr) 6 (CO) 4), molecule containing two atoms of the same metallic element with oxidation numbers differing by six units | |
| CN112795434A (en) | Processing technology of triglyceride type prickly ash seed oil | |
| CN1569786A (en) | Method for preparing phenol addition product of dicyclopentadiene |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C12 | Rejection of a patent application after its publication | ||
| RJ01 | Rejection of invention patent application after publication |