CN102153514A - Method for preparing fluorine-containing benzyl benzimidazole compound - Google Patents
Method for preparing fluorine-containing benzyl benzimidazole compound Download PDFInfo
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- CN102153514A CN102153514A CN 201110043353 CN201110043353A CN102153514A CN 102153514 A CN102153514 A CN 102153514A CN 201110043353 CN201110043353 CN 201110043353 CN 201110043353 A CN201110043353 A CN 201110043353A CN 102153514 A CN102153514 A CN 102153514A
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- phenylenediamine
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Abstract
The invention relates to a method for preparing a fluorine-containing benzyl benzimidazole compound. The method is used for surface treatment liquid of printing circuit boards. The method comprises the following steps of: dissolving o-phenylenediamine or substituted o-phenylenediamine in aromatic organic solvent, wherein a mass ratio of the o-phenylenediamine or the substituted o-phenylenediamine to the aromatic organic solvent is 1:(7-13); adding fluorine-containing organic acid into the obtained solution, wherein a molar ratio of the fluorine-containing organic acid added into the obtained solution to the o-phenylenediamine or the substituted o-phenylenediamine is (1.0-1.3):1; adding organic acid serving as a dehydrating agent, wherein a molar ratio of the organic acid serving as the dehydrating agent to the o-phenylenediamine or the substituted o-phenylenediamine is (0.5-1):1; heating to the temperature of between 110 and 150 DEG C, and reacting for 7 to 15 hours; cooling reaction solution to the room temperature, distilling the aromatic organic solvent out under reduced pressure, neutralizing residua by using an alkaline substance until the pH value is between 7.5 and 9.5, and filtering to precipitate a coarse product; and performing recrystallization purification on the coarse product, so that the rate of certified products is between 90 and 94. The method has the advantages of convenience in operation and high yield, and industrial production is easy to realize.
Description
Technical field
The present invention relates to the activeconstituents manufacture method of printed circuit board surface treatment liquid.
Background technology
Along with pb-free solder The Application of Technology and popularization, the raising of welding temperature has had higher requirement to the activity and the weldability on PCB copper surface, and the protectiveness and the wettability that improve PCB surface copper are PCB processing the heaviest rings of later stage.The OSP organic weldable protective agent is mainly used in the PCB(printed circuit board) in the welding process of the anti-oxidation and follow-up assembly technology of manufacturing, it is exactly on the naked copper surface of cleaning, generates one deck organic membrane with the method for chemistry.That this tunic has is anti-oxidation, heat shock resistance, wet fastness, is used for protecting the copper surface no longer to get rusty (oxidation or sulfuration etc.) its activeconstituents decisive role in normal environment.
Diphenyl-imidazole compound has been widely used in the activeconstituents in the printed circuit board surface treatment liquid.In U.S. Pat 5; 560; 785(1996.10.01), US 5; 498; 301(1996.03.12), European patent EP 0,627,499A(1994.12.07) etc. in the patent; in the surface treatment liquid of copper and copper alloy (being organic weldable protective membrane treatment solution), its active ingredient all is selected from the diaryl imidazole compound.Japanese Patent JP 2,005 349 439(2005.12.22) and open day 2006.04.19 of Chinese patent CN 1761773A() all use 2, the 2-position of 4-diphenyl-imidazole compound or 4-position phenyl are activeconstituents by the imidazolium compounds that chlorine atom or bromine atoms replace.Because the chemical conversion film that generates requires not change through the multiple high temp welding, but above chemical compound lot is still not ideal enough.Therefore require as very stable under the necessary high temperature of active ingredient.Particularly aspect preparation, synthetic four of Chinese patent CN1761773A contains two chlorine atom diphenyl-imidazole compounds.Owing to introduced halogen atoms such as chlorine, bromine, stability and thermotolerance are greatly improved, but are subjected to the restriction of RoHS instruction, and too much chlorine, bromine cause bad influence to environment, thereby suffer the resistance of a lot of producers and limit the use of.In order to seek New O SP, must seek activeconstituents and the synthetic method thereof of New O SP.Benzimidazole compound of the novel fluorine benzyl that the present invention relates to and preparation method thereof is not seen bibliographical information.
Summary of the invention
Technical problem to be solved by this invention provide a kind of easy to operate, yield is higher, be easy to realize the novel fluorine benzyl benzimidazole compound preparation method of suitability for industrialized production.The fluorine-containing benzyl benzimidazole compound that the present invention relates to has the structural formula shown in the formula I:
R wherein
1Be H, Me(methyl), the Et(ethyl) etc.; R
2, R
3, R
4, R
5Have at least two to be F, all the other are H.
The present invention be with O-Phenylene Diamine or substituted o-phenylenediamine, fluorine-containing organic acid under the dewatering agent effect and generate fluorine-containing benzyl benzimidazole compound.
Making method of the present invention:
Dissolve with aromatic organic solvent with O-Phenylene Diamine or substituted o-phenylenediamine, the quality grammes per square metre number of described O-Phenylene Diamine or substituted o-phenylenediamine is 1:7～13 with the ratio of the quality grammes per square metre number of used aromatic organic solvent, in gained solution, add fluorine-containing organic acid, the mol ratio of described fluorine-containing organic acid and O-Phenylene Diamine or substituted o-phenylenediamine is 1.0～1.3:1, add organic acid subsequently or mineral acid is made dewatering agent, the mol ratio of described organic acid or mineral acid and O-Phenylene Diamine or substituted o-phenylenediamine is 0.5～1:1, reheat to 110～150 ℃, reaction 7～15h, reaction solution is cooled to room temperature, decompression steams aromatic organic solvent, it is 7.5～9.5 that residuum is neutralized to PH with alkaline matter, crude product is separated out in filtration, and with existing recrystallization method of purification, get the percentage of A-class goods is 90～94% to crude product again.
The above substituted o-phenylenediamine is 4 replacements, and substituting group is Me, Et.
Aromatic organic solvent of the present invention is toluene, dimethylbenzene or chlorobenzene.
Fluorine-containing organic acid of the present invention is 3,4-difluorophenyl acetic acid, 2,6-difluorophenyl acetic acid or 2,4 difluorobenzene acetate.
Mineral acid of the present invention or organic acid are the vitriol oil, phosphoric acid, polyphosphoric acid or tosic acid.
Advantage of the present invention is easy to operate, and the yield height is easy to realize suitability for industrialized production.
Embodiment
Laboratory apparatus:
Nicolet 5DXFT-IR infrared spectrometer
The INOVA 500MB of U.S. Varian company NMR spectrometer with superconducting magnet
Switzerland METTLER-TOLEDO FP-62 type melting point detector (useful range: 25～300 ℃; Precision: 0.1 ℃)
The Quattro premier XE of U.S. Waters company type LC-MS instrument
The Germany Elementar Vario EL of company elemental analyser
Embodiment 1
2-(2,6-two fluoro-benzyls)-1H-benzoglyoxaline synthetic:
In the 200ml reaction flask of mechanical stirring, thermometer, reflux condensing tube is housed, add O-Phenylene Diamine 10.8g(0.1mol), with toluene 140g dissolving; Again to wherein adding 2,6-difluorophenyl acetic acid 21.7g(0.13mol), add polyphosphoric acid 31.5g(0.09mol again); Begin heating, to 110 ℃, reaction 15h.(developping agent is ethyl acetate: sherwood oil=1:1, R with TLC monitoring reaction process and reaction end
f=0.60).Reaction solution is cooled to room temperature; Decompression steams toluene; Residuum adds frozen water 50ml, and being neutralized to PH with ammoniacal liquor is 7.5; Filter, be washed with water to neutrality, drain at last, get crude product.Crude product adds 400ml water with 96 gram dissolve with ethanol, stirs and separates out crystal, filters, and oven dry promptly gets product 22.5g.Productive rate 92.2%.
M．P．?242-243℃
IR
，ν，cm
-1：3448.1(w)，3051.1（w），2950.3(w)，2887.1(w)，1628.8(s)，1485.8（s），1471.2（s），1457.9（s），1288.9（s），1031.9（s），785.5（m），756.5（s）。
1HNMR, (CDCl
3) δ (ppm): 4.3(s, 2H ,-CH
2-); 6.8～7.1(m, 3H, 3 H on the phenyl ring of fluorine place); 7.1～7.2(m, 4H, 3 H on the benzoglyoxaline phenyl ring).
MS(APCI)m/z(100%)：244（M
+，58.6），243[（M-1）
+，16.8]，225[(M-F)
+，100]，127?(
，10.0]，112[(
-1)
+，5.9]，77?(C
6H
5，5.0)；
Ultimate analysis: theoretical value C
14H
10F
2N
2: C 68.85, and H 4.13, and N 11.47, and F 15.56; Measured value: C 68.77, H 4.11, and N 11.46, and F 15.57.
Embodiment 2
2-(2,6-two fluoro-benzyls)-5-methyl isophthalic acid H-benzoglyoxaline synthetic:
In the 200ml reaction flask of mechanical stirring, thermometer, reflux condensing tube is housed, add 4-methyl-o-phenylenediamine 12.2g(0.1mol), with toluene 86g dissolving; Again to wherein adding 2,6-difluorophenyl acetic acid 16.7g(0.10mol), add polyphosphoric acid 35g(0.1mol again); Begin heating, to 150 ℃, reaction 7h.(developping agent is ethyl acetate: sherwood oil=1:1, R with TLC monitoring reaction process and reaction end
f=0.60).Reaction solution is cooled to room temperature; Decompression steams toluene; Residuum adds frozen water 50ml, and being neutralized to PH with ammoniacal liquor is 9.5; Filter, be washed with water to neutrality, drain at last, get crude product.Crude product 96g dissolve with ethanol adds 360ml water, stirs and separates out crystal, filters, and oven dry promptly gets product 23.4g.Productive rate 90.7%.
M．P．?207-208℃
IR
，ν，cm
-1：3447.8(w)，3025.0（w），2945.3(w)，2867.1(w)，1627.0(w)，1485.3（s），1470.8（s），1456.2（s），1276.4（s），1015.8（s），802.0（m），785.7（m）。
1HNMR, (CDCl
3) δ (ppm): 4.3(s, 2H ,-CH
2-); 6.8～7.1(m, 3H, 3 H on the phenyl ring of fluorine place); 7.2～7.4(m, 3H, 3 H on the benzoglyoxaline phenyl ring); 2.5(s, 3H, CH
3)
MS(APCI)m/z(100%)：258（M
+，61.9），257[(M-1)
+，21.2]，239[(M-F)
+，100]，222[(M+2)
+-2F，5.8]，145?(M
+-
，3.1)，?127（
，9.3），118[(
+1)
+，6.4]，77?(C
6H
5，5.9)；
Ultimate analysis: theoretical value C
15H
12F
2N
2: C 69.76, and H 4.68, and N 10.85, and F 14.71; Measured value: C 69.73, H 4.76, and N 10.78, and F 14.70.
Embodiment 3
Synthetic (1) of 2-(3,4-two fluoro-benzyls)-1H-benzoglyoxaline:
In the 200ml reaction flask of mechanical stirring, thermometer, reflux condensing tube is housed, add O-Phenylene Diamine 10.8g(0.1mol), with dimethylbenzene 108g dissolving; Again to wherein adding 3,4-difluorophenyl acetic acid 19.3g(0.115mol), add polyphosphoric acid 26.3g(0.075mol again); Begin heating, to 125 ℃, reaction 11h.(developping agent is ethyl acetate: sherwood oil=1:1, R with TLC monitoring reaction process and reaction end
f=0.60).Reaction solution is cooled to room temperature; Decompression steams dimethylbenzene; Residuum adds frozen water 50ml, and being neutralized to PH with ammoniacal liquor is 8.5; Filter, be washed with water to neutrality, drain at last, get crude product.Crude product 80g dissolve with ethanol adds 300ml water, stirs and separates out crystal, filters, and oven dry promptly gets product 22.9g.Productive rate 94.0%.
M．P．?160-161℃
IR
，ν，cm
-1：3447.5(w)，3083.8（w），2998.4(w)，2737.3(w)，1612.9(w)，1537.7（s），1516.7（s），1456.2（s），1420.5（s），1282.8（s），766.0（s），747.6（m）。
1HNMR,(CDCl
3)δ(ppm):4.2（s，2H，-CH
2-）；
6.9～7.1(m, 3H, 3 H on the phenyl ring of fluorine place); 7.2～7.6 (m, 4H, 4 H on the benzoglyoxaline phenyl ring);
MS(APCI)m/z(100%)：244（M
+，95.5），243[(M-1)
+，100]，225[(M-F)
+，6.4]，?131(
，10.5)，?112[(
-1)
+，5.1]，77?(C
6H
5，4.3)；
Ultimate analysis: theoretical value C
14H
10F
2N
2: C 68.85, and H 4.13, and N 11.47, and F 15.56;
Measured value: C 68.73, H 4.21, and N 11.50, and F 15.56.
Embodiment 4
Synthetic (2) of 2-(3,4-two fluoro-benzyls)-1H-benzoglyoxaline:
Charge ratio and operation are fully identical with embodiment 3.
But polyphosphoric acid 26.3g (0.075mol) changes tosic acid 9.4g(0.05mol into).Products obtained therefrom 22.2g, productive rate 90.1%.
M.P and IR,
1Spectroscopic data such as H-NMR, MS, ultimate analysis (EA) measurement result are consistent with embodiment 3.
Embodiment 5
According to the present invention; a kind of copper face OSP treatment agent that is applicable to the welding of printed circuit board multiple high temp leadless can be provided; copper pad to printed circuit board has very outstanding defencive function; anti-oxidant strong with anti-tarnishing ability; last tin after the multiple high temp leadless Reflow Soldering significantly improves, and reaches circuit card international norm (IPC standard).
Scheme one (A solution): earlier with 0.5% 2-(4-acetyl phenyl)-4-(4-fluorophenyl) imidazoles and 0.05% 2-(2, the 6-difluorobenzyl)-the 1-H-benzoglyoxaline is dissolved in 10% the Succinic Acid, all pour in the deionized water after the dissolving fully, add 1.0% ferric sulfate, 0.1% iodopropionic acid and 0.01% monoethanolamine again, after the stirring and dissolving, regulate pH value to 3.6 with ammoniacal liquor, make the OSP treatment agent thus;
Scheme two (B solution): will contain 2-of the present invention (2, the 6-difluorobenzyl)-1-H-benzoglyoxaline amount of 0.05% of getting and be dissolved among the A.
2 printed circuit board test films were soaked 30 seconds in degreaser (45 ℃), after washing 3 times, in micro-etching agent (30 ℃), soaked 40 seconds, after washing 3 times, in 2% aqueous acetic acid, cleaned 20 seconds, wash 2 times after again with DI water cleaning 1 time, blotting the back soaked respectively 60 seconds in 40 ℃ A, B treatment agent solution, blot the back and wash 3 times with DI, drying promptly gets the test board A ', the B ' that scribble the OSP film.The last tin rate evaluation result in the discolouration of A ', B ' test board OSP film after three unleaded Reflow Solderings and socket hole (DIMM hole) is as follows:
Claims (5)
1. fluorine-containing benzyl benzimidazole compound manufacture method, it is characterized in that dissolving with aromatic organic solvent with O-Phenylene Diamine or substituted o-phenylenediamine, the quality grammes per square metre number of described O-Phenylene Diamine or substituted o-phenylenediamine is 1:7 ~ 13 with the ratio of the quality grammes per square metre number of used aromatic organic solvent, in gained solution, add fluorine-containing organic acid, the mol ratio of described fluorine-containing organic acid and O-Phenylene Diamine or substituted o-phenylenediamine is 1.0 ~ 1.3:1, add organic acid subsequently or mineral acid is made dewatering agent, the mol ratio of described organic acid or mineral acid and O-Phenylene Diamine or substituted o-phenylenediamine is 0.5 ~ 1:1, reheat to 110 ~ 150 ℃, reaction 7～15h, reaction solution is cooled to room temperature, decompression steams aromatic organic solvent, it is 7.5～9.5 that residuum is neutralized to PH with alkaline matter, crude product is separated out in filtration, with existing recrystallization method of purification, get the percentage of A-class goods is 90～94% to crude product again.
2. according to the described fluorine-containing benzyl benzimidazole compound manufacture method of claim 1, it is characterized in that described substituted o-phenylenediamine is 4 replacements, substituting group is Me, Et.
3. according to the described fluorine-containing benzyl benzimidazole compound manufacture method of claim 1, it is characterized in that described aromatic organic solvent is toluene, dimethylbenzene or chlorobenzene.
4. according to the described fluorine-containing benzyl benzimidazole compound manufacture method of claim 1, it is characterized in that described fluorine-containing organic acid is 3,4-difluorophenyl acetic acid, 2,6-difluorophenyl acetic acid or 2,4 difluorobenzene acetate.
5. according to the described fluorine-containing benzyl benzimidazole compound manufacture method of claim 1, it is characterized in that described mineral acid or organic acid are dense stream acid, phosphoric acid, polyphosphoric acid or tosic acid.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102827084A (en) * | 2012-08-21 | 2012-12-19 | 江苏恒祥化工有限责任公司 | Preparation method of 2-(dichloromethyl)benzimidazole |
| CN103058931A (en) * | 2012-12-31 | 2013-04-24 | 广东东硕科技有限公司 | Four 2-(3', 5'-dihalo-benzyl) benzimidazole type novel compounds and preparation method thereof |
| CN108752585A (en) * | 2018-04-17 | 2018-11-06 | 同济大学 | A kind of polybenzimidazoles compound of fluorine-containing side group and preparation method thereof |
| CN109379857A (en) * | 2018-09-18 | 2019-02-22 | 宏维科技（深圳）有限公司 | A kind of preparation method and application method being bonded inorganic agent, the inorganic agent |
| CN110563926A (en) * | 2019-08-26 | 2019-12-13 | 长春长光宇航复合材料有限公司 | Fluorine-containing epoxy resin curing agent and preparation method thereof, and epoxy resin material and preparation method thereof |
| CN115490668A (en) * | 2022-08-30 | 2022-12-20 | 深圳市贝加电子材料有限公司 | Pyrimidyl imidazole compound, preparation method thereof and organic weldable protective agent |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101448978A (en) * | 2006-05-19 | 2009-06-03 | 四国化成工业株式会社 | Metal surface treatment agent and use of same |
| CN101891688A (en) * | 2010-07-30 | 2010-11-24 | 孝感市诚嘉药物研究所 | Preparation method for bendazol in industrialized production |
-
2011
- 2011-02-23 CN CN 201110043353 patent/CN102153514B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101448978A (en) * | 2006-05-19 | 2009-06-03 | 四国化成工业株式会社 | Metal surface treatment agent and use of same |
| CN101891688A (en) * | 2010-07-30 | 2010-11-24 | 孝感市诚嘉药物研究所 | Preparation method for bendazol in industrialized production |
Non-Patent Citations (1)
| Title |
|---|
| 《Science of Synthesis》 20020508 M.R.Grimmett et al. Five-menbered hetarenes with two nitrogen or phosphorus atoms Georg Thieme Verlag 537-540 第12卷, * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102827084A (en) * | 2012-08-21 | 2012-12-19 | 江苏恒祥化工有限责任公司 | Preparation method of 2-(dichloromethyl)benzimidazole |
| CN103058931A (en) * | 2012-12-31 | 2013-04-24 | 广东东硕科技有限公司 | Four 2-(3', 5'-dihalo-benzyl) benzimidazole type novel compounds and preparation method thereof |
| CN108752585A (en) * | 2018-04-17 | 2018-11-06 | 同济大学 | A kind of polybenzimidazoles compound of fluorine-containing side group and preparation method thereof |
| CN109379857A (en) * | 2018-09-18 | 2019-02-22 | 宏维科技（深圳）有限公司 | A kind of preparation method and application method being bonded inorganic agent, the inorganic agent |
| CN110563926A (en) * | 2019-08-26 | 2019-12-13 | 长春长光宇航复合材料有限公司 | Fluorine-containing epoxy resin curing agent and preparation method thereof, and epoxy resin material and preparation method thereof |
| CN115490668A (en) * | 2022-08-30 | 2022-12-20 | 深圳市贝加电子材料有限公司 | Pyrimidyl imidazole compound, preparation method thereof and organic weldable protective agent |
| CN115490668B (en) * | 2022-08-30 | 2024-04-02 | 深圳市贝加电子材料有限公司 | Pyrimidylimidazole compound, preparation method thereof and organic solderability preservative |
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