CN106749241A - Formoxyl diimide derivative of 1,4,5,8 naphthalene four and application thereof - Google Patents
Formoxyl diimide derivative of 1,4,5,8 naphthalene four and application thereof Download PDFInfo
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- CN106749241A CN106749241A CN201611232060.1A CN201611232060A CN106749241A CN 106749241 A CN106749241 A CN 106749241A CN 201611232060 A CN201611232060 A CN 201611232060A CN 106749241 A CN106749241 A CN 106749241A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
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- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25D—PROCESSES FOR THE ELECTROLYTIC OR ELECTROPHORETIC PRODUCTION OF COATINGS; ELECTROFORMING; APPARATUS THEREFOR
- C25D3/00—Electroplating: Baths therefor
- C25D3/02—Electroplating: Baths therefor from solutions
- C25D3/38—Electroplating: Baths therefor from solutions of copper
Abstract
The present invention relates to formoxyl diimide derivative of a kind of 1,4,5,8 naphthalene four and application thereof.Described Isosorbide-5-Nitrae, the formoxyl diimide derivative of 5,8 naphthalene four is compound shown in formula I, and it can be used as the application of the smoothing agent of acid copper plating.In formula I, R1And R2It is respectively selected from：Hydrogen, C1~C6Alkyl, the C of halo1~C6Alkyl, group shown in formula II or group shown in formula III, and R1And R2In at least one be group shown in formula II or group shown in formula III；M is 1 or 2；X is halogen；Wherein, R3~R8It is respectively and independently selected from：C1~C3A kind of in alkyl, n is 1~12 integer, and p is 1~6 integer.
Description
Technical field
The present invention relates to a kind of naphthoyl imide compounds and application thereof, specifically, it is related to a kind of Isosorbide-5-Nitrae, 5,8- naphthalene tetramethyls
Acyl group diimide derivative and application thereof.
Background technology
Electroplating engineering is to study electroplating industry with the chemical process and physics mistake conducted in the production of other related industries
One engineering science of journey common law, is one of key technology of advanced manufacturing technology industrial chain.It is with chemistry, physics
A cross discipline based on, electronics, machinery and mathematics.Since the mid-term electroplating technology application of 19th century, the technology
Constantly improved and developed.After especially into 21 century, development and needs with electronic technology, copper electroplating layer is because of it
There is good electric conductivity, thermal conductivity and mechanical ductility and be widely used in the fields such as electronics and IT products.Electricity
Coating technology has evolved into indispensable important component in national economic development, and is widely used in machinery, shipbuilding, aviation
Many aspects such as space flight, military project, electronics, nuclear industry, light industry, dairy industry, with the corrosion resistance for improving product, ornamental and work(
Can property.The piece surfaces such as door handle, instrument board, trade mark such as in automobile can become its outward appearance after having plated layer of metal coating
Obtain more aesthetically pleasing；Hard chrome is plated in cylinder inner wall, the wearability of product can be improved so as to extend the service life of product；In fastening
Zinc and the corrosion resistance of product can be greatly improved after appropriate post processing flow on part plated surface；The plated with gold on sanitaryware
Category coating can improve the corrosion resistance of product, the service life of extension product can make product appearance get a promotion again.Therefore, electroplate
Closely bound up with daily life, small to lighter, spectacle frame, greatly to aircraft, the surface treatment of automobile, we can
The most of product seen all is by electroplating processes.
Because the geomery of electroplating device in industrial production is different, the current density of workpiece surface each point is each in electroplating bath
It is different, if depend merely on the modes such as the convection current for improving plating solution and being difficult to obtain thickness distribution uniformly and meeting the copper plating of various functions requirement
Layer.Therefore industrially in order to obtain the uniform copper coating of surface-brightening, excellent physical properties, thickness distribution, conventional method is
Organic additive is added in electrolytic copper plating solution.
In copper sulfate baths commonly use additive by its effect in the plating solution can be divided mainly into inhibitor, brightener and
Three kinds of leveling agent.In actual electroplating process, in the case that additive is subject to diffusing step to control, electroplating additive particle is usual
Diffusion occurs, and adsorbs at the larger electrode surface protrusion of tension force and on the avtive spot of electro-deposition, cause in electricity
The metallic atom of pole Adsorption on Surface constantly moves to the recess of electrode surface and enters inside metal lattice, so as to play
The bright levelling effect of additive.The concentration of additive often only has 1/102 to 1/105 times of concentration of metal ions, but this
A little a small amount of additives can bring coating morphology composition and crystal lattice orientation strong influence.Therefore, in order that plated material
Surface topography and physical property meet standard and the requirement of every profession and trade, electroplating additive is served in acid copper sulfate plating
Very key effect.
Then from last century the nineties so far, external major Additive Production business (German Atotech, Japan is big and waits)
Dye-type additives such as " 210 " " Ultra " is proposed in the domestic market for general hardware electroplating industry copper facing.And dye-type
The use of electroplating additive can increase the cost of economy and environment, and the plating addition of existing dye-type in water pollution control
Agent has that species is few, difficult prepare (preparation technology complicated), easily decomposes and the defect such as cost is high.So research and development preparation technology is relatively simple
Single, low cost, and environmentally friendly reactive monoazo dyestuffs type electroplating additive enjoys the concern of this area scientist.
Chinese patent literature CN 105646346A are disclosed as the naphthoyl imide compounds of straight and even dose of acid electroplating,
But its performance still has room for improvement.
The content of the invention
The present inventor designs and has synthesized a kind of novel formoxyl imidodicarbonic diamide of 1,4,5,8- naphthalenes four of structure and spreads out
Biology, after tested, the series derivates show the good chemical property for suppressing copper deposition.
A purpose of the invention is, there is provided a kind of novel Isosorbide-5-Nitrae of structure, the formoxyl imidodicarbonic diamide of 5,8- naphthalene four derives
Thing.
The described formoxyl diimide derivative of 1,4,5,8- naphthalenes four is compound shown in formula I：
In formula I, R1And R2It is respectively selected from：Hydrogen (H), C1~C6Alkyl, the C in halogen (F, Cl, Br or I) generation1~C6Alkyl, formula II
Shown group or group shown in formula III, and R1And R2In at least one be group shown in formula II or group shown in formula III；M be 1 or
2；X is halogen (F, Cl, Br or I)；
In formula II and III, R3~R8It is respectively and independently selected from：C1~C3A kind of in alkyl, n is 1~12 integer, and p is 1~6
Integer, curve mark for substitution position (similarly hereinafter).
Another object of the present invention is to disclose above-mentioned Isosorbide-5-Nitrae, a kind of use of the formoxyl diimide derivative of 5,8- naphthalene four
On the way：I.e. shown in formula I compound as the smoothing agent of acid copper plating (such as with copper sulphate as electroplate liquid) application.
Additionally, the method that the present invention also provides compound shown in a kind of formula I, methods described has main steps that：With
Isosorbide-5-Nitrae, the formoxyl dianhydride of 5,8- naphthalene four (compound shown in formula IV) is initiation material, first, using prior art by shown in formula IV
Compound is converted into the formoxyl imidodicarbonic diamide of 1,4,5,8- naphthalenes four (compound shown in formula V)；Then, by shownization of formula IV or V
Compound and R1aY or R2aY, and/or NH2R1bNH2、NH2R2bNH2、H2R1bY、NH2R2bY、YR1bY or YR2bY reacts, and obtains intermediate；
Finally, gained intermediate is reacted through " quaternization ", obtains object (compound shown in formula I).
Wherein, Y is halogen (F, Cl, Br or I)；R1aAnd R2aIt is respectively selected from：C1~C6Alkyl or halogen (F, Cl, Br or I) generation
C1~C6It is a kind of in alkyl；R1bAnd R2bIt is respectively selected from：It is a kind of in group shown in a of formula II or group shown in a of formula III；N's and p determines
It is adopted identical with described previously.
Brief description of the drawings
Fig. 1 are the cyclic voltammetry curve of compound shown in the A of formula I；
Fig. 2 are the cyclic voltammetry curve of compound shown in the B of formula I；
Fig. 3 are the cyclic voltammetry curve of compound shown in the C of formula I；
Fig. 4 are the cyclic voltammetry curve of compound shown in the D of formula I；
Fig. 5 are the cyclic voltammetry curve of compound shown in the E of formula I；
Fig. 6 are the cyclic voltammetry curve of compound shown in formula Nap；
Fig. 7 are the cyclic voltammetry curve of compound shown in formula JGB.
Specific embodiment
In a preferred technical scheme of the invention, R1And R2It is respectively selected from：H, the C in halogen (F, Cl, Br or I) generation1~C6
Alkyl, group shown in formula II or group shown in formula III, and R1And R2In at least one be group shown in formula II or base shown in formula III
Group；M is 1 or 2；X is halogen (F, Cl, Br or I)；
In formula II and III, R3~R8It is respectively and independently selected from：C1~C3A kind of in alkyl, n is 1~6 integer, and p is 1~3
Integer.
Further preferred scheme is：R1And R2It is respectively selected from：The C in H, F generation6Alkyl, group shown in formula II or the institute of formula III
Show group, and R1And R2In at least one be group shown in formula II or group shown in formula III；M is 1 or 2；X is Br or I；
In formula II and III, R3~R8Methyl is, n is 1~6 integer, and p is 1 or 2.
Further preferred scheme is again：R1And R2It is respectively selected from one kind in following groups：
Below by embodiment, the present invention is further elaborated, it is therefore intended that is best understood from present disclosure, is lifted
Example do not limit the scope of the invention.
Embodiment 1
The preparation of the formoxyl imidodicarbonic diamide of 1,4,5,8- naphthalenes four (compound shown in formula V)：
By Isosorbide-5-Nitrae, the formoxyl dianhydride (2g, 7.5mmol) of 5,8- naphthalene four and ammonium acetate (11.5g, 150mmol) are dissolved in acetic acid
(40mL), heating stirring back flow reaction 1h.Reaction solution is cooled to room temperature, depressurize suction filtration and with acetic acid (50mL) and ether
(100mL) washing filter cake obtains yellow solid (compound shown in formula V), yield 95%.
Embodiment 2
The preparation of compound shown in the A of formula I：
By compound (2.14g, 8mmol) shown in formula IV, 80mL deionized waters, N, N- dimethyl -1,3- diaminopropanes
(2.82g, 32mmol) mixing is placed in reaction bulb, is heated to 80 DEG C, stirring reaction 15h.Stop reaction, be cooled to room temperature, use
Dichloromethane (20mL) is extracted 5 times, collects organic phase, and use anhydrous sodium sulfate drying.Product is concentrated and through silica gel column layer point
From (dichloromethane：Triethylamine is 40：1 (v/v)), chromatography obtain product again with ethyl alcohol recrystallization obtain yellow solid (in
Mesosome A), yield 85%.
Intermediate A (0.434g, 1mmol) is taken to be dissolved in 20mL acetonitriles, then in reaction system add iodomethane (2.28g,
16mmol), 18h is stirred at room temperature.Reaction solution is depressurized suction filtration, resulting filter cake obtains yellow solid after being washed with acetonitrile (20mL)
(compound shown in the A of formula I), yield 90%.
Intermediate A：1H NMR(400MHz,CDCl3):δ 8.75 (s, 4H), 4.26 (t, J=7.6Hz, 4H), 2.44 (t, J
=7.2Hz, 4H), 2.24 (s, 12H), 1.92 (m, 4H)；13C NMR(100MHz,CDCl3):162.8,130.9,126.7,
126.6,57.2,45.4,39.4,25.9；HRMS(TOF-ESI)：m/z：calcd for C24H29N4O4：437.5159；
Found：437.5157.
Compound shown in the A of formula I：1H NMR(400MHz,DMSO):δ 8.73 (s, 4H), 4.16 (t, J=7.6Hz, 4H),
3.48(m,4H),3.05(s,18H),2.17(m,4H)；13C NMR(100MHz,DMSO):162.9,130.5,126.4,
126.2,63.2,52.2,37.4,21.6；HRMS(TOF-ESI)：m/z：calcd for C13H34N2O2：233.1285；
Found：233.1287.
Embodiment 3
The preparation of compound shown in the B of formula I：
By compound (0.532g, 2mmol) shown in formula V, Isosorbide-5-Nitrae-dibromobutane (0.322g, 1.5mmol), potassium carbonate
(0.552g, 2mmol), the KI of catalytic amount is dissolved in the DMF of 40mL (DMF), is heated to 60 DEG C, is stirred
Mix reaction 20h.Reaction solution is poured into 200mL water, a large amount of solids are separated out, decompression suction filtration obtains filter cake, rinsed with water (50mL)
Clean filter cake, dries to obtain gray solid (intermediate B), yield 80%.
By intermediate B (0.4g, 1mmol), trimethy-lammonium chloride (0.96g, 10mmol), sodium acid carbonate (0.84g,
10mmol) it is dissolved in 30mL acetonitriles, is heated to 80 DEG C, stirring reaction 12h.Question response liquid is cooled to room temperature, rotates acetonitrile molten
Agent, yellow solid (compound shown in the B of formula I), yield 85% are obtained with methyl alcohol/recrystallized from acetonitrile.
Intermediate B：1H NMR(400MHz,CDCl3):δ 11.52 (s, 1H), 8.69 (s, 4H), 3.75 (t, J=7.6Hz,
2H), 3.56 (t, J=7.2Hz, 2H), 1.92 (m, 2H), 1.75 (m, 2H)；13C NMR(100MHz,CDCl3):160.8,
138.9,133.7,122.6,47.2,39.4,28.4,27.9；HRMS(TOF-ESI)：m/z：calcd for C18H14BrN2O4：
401.0131；Found：401.0128.
Compound shown in the B of formula I：1H NMR(400MHz,DMSO):δ11.43(s,1H),8.62(s,4H),3.56(s,
9H), 3.22 (t, J=7.6Hz, 2H), 3.14 (t, J=7.2Hz, 2H), 1.71 (m, 2H), 1.56 (m, 2H)；13C NMR
(100MHz,DMSO):160.8,138.9,133.7,122.6,54.8,47.2,39.4,28.4,27.9；HRMS(TOF-ESI)：
m/z：calcd for C21H22N3O4：380.1605；Found：380.1601.
Embodiment 4
The preparation of compound shown in the C of formula I：
Compound (2g, 7.5mmol) shown in formula IV and 6- bromines hexylamine (2.88g, 16mmol) are dissolved in the N, N- bis- of 40mL
In NMF (DMF), 50 DEG C of reaction 4h are heated to, are again heated to 120 DEG C of reaction 12h.Reaction solution is cooled to room temperature, is revolved
Solvent is evaporated, brown crude product is obtained, then (dichloromethane/acetone is 10/1- dichloromethane/acetone (2% first with chromatography
Alcohol) 10/3) to obtain light yellow solid (intermediate C), (3.77g, 85%).
By intermediate C (0.59g, 1mmol), trimethy-lammonium chloride (0.96g, 10mmol), sodium acid carbonate (0.84g,
10mmol) it is dissolved in 30mL acetonitriles, is heated to 80 DEG C, stirring reaction 12h.Question response liquid is cooled to room temperature, rotates acetonitrile molten
Agent, yellow solid 0.467g (compound shown in the C of formula I), yield 85% are obtained with methyl alcohol/recrystallized from acetonitrile.
Intermediate C：1H NMR(400MHz,CDCl3):δ 8.71 (s, 4H), 4.16 (t, J=7.6Hz, 4H), 2.61 (t, J
=7.2Hz, 4H), 1.82 (m, 4H), 1.62 (m, 4H), 1.36 (m, 8H)；13C NMR(100MHz,CDCl3):162.8,
130.9,126.7,126.6,57.2,45.4,43.8,39.4,36.8,25.9；HRMS(TOF-ESI)：m/z：calcd for
C26H29Br2N4O4：593.0468；Found：593.0464.
Compound shown in the C of formula I：1H NMR(400MHz,DMSO):δ 8.62 (s, 4H), 4.16 (t, J=7.6Hz, 4H),
3.48 (t, J=7.2Hz, 4H), 3.05 (s, 18H), 1.71 (m, 8H), 1.45 (m, 8H)；13C NMR(100MHz,DMSO):
162.4,130.3,126.1,125.8,63.2,52.2,48.9,45.6,42.3,37.4,21.6；HRMS(TOF-ESI)：m/z：
calcd for C16H23N2O2：275.1754；Found：275.1756.
Embodiment 5
The preparation of compound shown in the D of formula I：
By compound (0.532g, 2mmol) shown in formula V, compound a (0.825g, 3mmol), potassium carbonate (0.828g,
1.5mmol), the KI of catalytic amount is dissolved in the DMF of 30mL (DMF), is heated to 120 DEG C, stirring reaction
20h.Reaction solution is poured into 200mL water, a large amount of solids are separated out, depressurize suction filtration, gained filter cake rinses filter cake with water (50mL), dries
Do to obtain gray solid, light yellow solid (intermediate is obtained through silicagel column column chromatography for separation (dichloromethane/acetone=10/3 (v/v))
D) (0.921g, 75%).
Take intermediate D (0.656g, 1mmol), trimethy-lammonium chloride (0.96g, 10mmol), sodium acid carbonate (0.84g,
10mmol) it is dissolved in 30mL acetonitriles, is heated to 80 DEG C, stirring reaction 12h.Question response liquid is cooled to room temperature, rotates acetonitrile molten
Agent, yellow solid 0.544 (compound shown in the D of formula I), yield 85% are obtained with methyl alcohol/recrystallized from acetonitrile.
Intermediate D：1H NMR(400MHz,CDCl3):δ 8.78 (s, 4H), 4.16 (t, J=7.6Hz, 4H), 3.89 (t, J
=7.2Hz, 4H), 3.51 (t, J=7.2Hz, 4H), 3.31 (t, J=7.6Hz, 4H), 3.15 (m, 8H)；13C NMR(100MHz,
CDCl3):163.4,130.6,125.9,124.6,67.2,65.4,58.8,39.4,36.8,25.9；HRMS(TOF-ESI)：m/
z：calcd for C26H29Br2N4O8：657.0265；Found：657.0264.
Compound shown in the D of formula I：1H NMR(400MHz,DMSO):δ 8.75 (s, 4H), 4.14 (t, J=7.6Hz, 4H),
3.84 (t, J=7.2Hz, 4H), 3.48 (t, J=7.2Hz, 4H), 3.26 (t, J=7.6Hz, 4H), 3.15 (m, 8H) 3.05 (s,
18H)；13C NMR(100MHz,DMSO):163.3,130.4,125.8,124.4,67.2,65.4,58.8,46.8,39.4,
36.8,25.9；HRMS(TOF-ESI)：m/z：calcd for C13H23N2O4：307.1652；Found：307.1649.
Embodiment 6
The preparation of compound shown in the E of formula I：
By compound (0.532g, 2mmol) shown in formula V, 1,1,2,2- tetrahydrochysene perfluoro-hexyl iodide (0.935g,
2.5mmol), potassium carbonate (1.656g, 3mmol), the KI of catalytic amount is dissolved in the DMF of 30mL (DMF)
In, it is heated to 100 DEG C, stirring reaction 8h.Reaction solution is poured into 200mL water after being cooled to room temperature, separates out a large amount of solids, decompression
Suction filtration, resulting filter cake water (50mL) rinses filter cake well, and filter cake is recrystallized with ethanol as solvent, dries greyish white
Color solid (intermediate E a) (0.512g, 50%).
By intermediate E a (0.512g, 1mmol), Isosorbide-5-Nitrae-dibromobutane (0.322g, 1.5mmol), potassium carbonate (0.552g,
2mmol), the KI of catalytic amount is dissolved in the DMF of 30mL (DMF), is heated to 100 DEG C, stirring reaction
8h.Reaction solution is poured into 200mL water after being cooled to room temperature, separates out a large amount of solids, depressurize suction filtration, resulting filter cake water
(50mL) rinses filter cake well, then chromatography (methylene chloride/methanol=50/1 (v/v)) is carried out to filter cake dries white solid
Body (intermediate E b) (0.485g, 75%).
By intermediate E b (0.323g, 0.5mmol), trimethy-lammonium chloride (0.96g, 10mmol), sodium acid carbonate (0.84g,
10mmol) it is dissolved in 30mL acetonitriles, is heated to 80 DEG C, stirring reaction 12h.Question response liquid is cooled to room temperature, rotates acetonitrile molten
Agent, yellow solid (compound shown in the E of formula I) (0.266g, 85%) is obtained with methyl alcohol/recrystallized from acetonitrile.
Intermediate E a：1H NMR(400MHz,CDCl3):δ 11.27 (s, 1H), 8.63 (s, 4H), 3.79 (t, J=7.6Hz,
2H),1.98(m,2H)；13C NMR(100MHz,CDCl3):159.1,138.6,135.8,124.6,124.0,121.3,
120.6,118.5,117.2,109.5,28.9,24.7；19F NMR(400MHz,CDCl3):δ-80.9(m,3F),-114.7(m,
2F),-124.3(m,2F),-126.0(m,2F)；HRMS(TOF-ESI)：m/z：calcd for C20H10F9N2O4：
513.0491；Found：513.0489.
Intermediate E b：1H NMR(400MHz,CDCl3):δ 8.62 (s, 4H), 3.72 (t, J=7.6Hz, 2H), 3.52 (t, J
=7.2Hz, 2H), 3.14 (t, J=7.6Hz, 2H), 1.82-1.89 (m, 4H), 1.56 (m, 2H)；13C NMR(100MHz,
CDCl3):159.1,138.6,135.8,124.6,124.0,121.3,120.6,118.5,117.2,109.5,69.3,67.9,
50.5,46.7,29.1,24.7；19F NMR(400MHz,CDCl3):δ-80.9(m,3F),-114.6(m,2F),-124.4(m,
2F),-126.0(m,2F)；HRMS(TOF-ESI)：m/z：calcd for C24H17BrF9N2O4:647.0222；Found:
647.0223.
Compound shown in the E of formula I：1H NMR(400MHz,DMSO):δ 8.61 (s, 4H), 3.72 (t, J=7.6Hz, 2H),
3.47(s,9H),3.14-3.18(m,4H),2.13(m,2H),1.58-1.61(m,4H)；13C NMR(100MHz,DMSO):
159.1,138.6,135.8,124.6,124.0,121.3,120.6,118.5,117.2,109.5,69.3,67.9,54.8,
50.5,46.7,29.1,24.7；19F NMR(400MHz,DMSO):δ-80.9(m,3F),-114.6(m,2F),-124.4(m,
2F),-126.0(m,2F)；HRMS(TOF-ESI)：m/z：calcd for C27H25F9N3O4：626.1696；Found：
626.1698。
Embodiment 7
Prepare a CuSO containing 50g/L4·5H2O and 250g/L H2SO4Copper-bath, with Pt rotating disk electrode (r.d.e)s make
It is working electrode, platinum rod is used as to electrode and Ag/AgCl, used as reference electrode, rotating speed is under conditions of 2000 revs/min, in solution
It is 2.5g/L by above-described embodiment prepare compound IA~IE that 0.02mL, concentration is added dropwise in (100mL) every time, does cyclic voltammetric
Curve is tested, and gained cyclic voltammetry curve is shown in Fig. 1~5.The addition of additive is bigger during cyclic voltammetry, the oxidation for obtaining
Peak area is smaller, and corresponding is stronger inhibitory action, and when peak area ratio is less than 0.5, the EOT end of test.
Comparative example
With the smoothing agent of existing commercial acid copper plating：" being good for that green " (compound shown in formula b, be abbreviated as " JGB ")
Being reported with CN 105646346A can be used as the naphthoyl imide compounds (chemical combination shown in formula c of the smoothing agent of acid copper plating
Thing, is abbreviated as " Nap ") test of embodiment 7 is repeated, its test loop volt-ampere curve is shown in Fig. 6~7, and titration results are shown in Table 1..
Table 1
Titration results (being shown in Table 1) are the amount for having investigated the additive consumed when peak area ratio is by 0.8, compound addition
Amount is fewer, shows that the inhibitory action of compound is stronger.In other words, the planarization effects of gained coating are also got in electroplating process
It is good.
From table 1., Isosorbide-5-Nitrae provided by the present invention, the plating of the formoxyl diimide derivative of 5,8- naphthalene four suppresses effect
Fruit is superior to JGB and Nap (particularly compound shown in Formulas I A, IC and ID), is expected to be developed to a kind of plating of excellent performance
Smoothing agent.
Claims (7)
1. a kind of Isosorbide-5-Nitrae, the formoxyl diimide derivative of 5,8- naphthalene four, it is compound shown in formula I：
In formula I, R1And R2It is respectively selected from：Hydrogen, C1~C6Alkyl, the C of halo1~C6Alkyl, shown in group shown in formula II or formula III
Group, and R1And R2In at least one be group shown in formula II or group shown in formula III；M is 1 or 2；X is halogen；
Wherein, R3~R8It is respectively and independently selected from：C1~C3A kind of in alkyl, n is 1~12 integer, and p is 1~6 integer.
2. Isosorbide-5-Nitrae as claimed in claim 1, the formoxyl diimide derivative of 5,8- naphthalene four, it is characterised in that wherein, n is 1
~6 integer, p is 1~3 integer.
3. Isosorbide-5-Nitrae as claimed in claim 2, the formoxyl diimide derivative of 5,8- naphthalene four, it is characterised in that wherein, R1And R2
It is respectively selected from：Hydrogen, the C of fluoro6Alkyl, group shown in formula II or group shown in formula III, and R1And R2In at least one be formula II
Shown group or group shown in formula III；M is 1 or 2；X is Br or I.
4. Isosorbide-5-Nitrae as claimed in claim 3, the formoxyl diimide derivative of 5,8- naphthalene four, it is characterised in that wherein, R1And R2
It is respectively selected from one kind in following groups：
H
5. Isosorbide-5-Nitrae as claimed in claim 4, the formoxyl diimide derivative of 5,8- naphthalene four, it is characterised in that described Isosorbide-5-Nitrae,
The formoxyl diimide derivative of 5,8- naphthalenes four is one kind in following compounds：
6. the formoxyl diimide derivative of 1,4,5,8- naphthalenes four as described in any one in Claims 1 to 5 is used as acidity
The application of the smoothing agent of electro-coppering.
7. application as claimed in claim 6, it is characterised in that the electroplate liquid of wherein described acid copper plating is copper sulphate.
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| CN110372700A (en) * | 2019-06-27 | 2019-10-25 | 黄冈师范学院 | A kind of naphthalene-Isosorbide-5-Nitrae, the synthetic method of 5,8- tetra- formyl, two hydrazine |
| CN110983389A (en) * | 2019-12-31 | 2020-04-10 | 广州三孚新材料科技股份有限公司 | Cyanide-free alkaline copper electroplating solution for steel parts and preparation method thereof |
| CN114874211A (en) * | 2022-03-30 | 2022-08-09 | 西安交通大学 | Imide derivative, preparation method and application in flow battery |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110372700A (en) * | 2019-06-27 | 2019-10-25 | 黄冈师范学院 | A kind of naphthalene-Isosorbide-5-Nitrae, the synthetic method of 5,8- tetra- formyl, two hydrazine |
| CN110983389A (en) * | 2019-12-31 | 2020-04-10 | 广州三孚新材料科技股份有限公司 | Cyanide-free alkaline copper electroplating solution for steel parts and preparation method thereof |
| CN110983389B (en) * | 2019-12-31 | 2020-11-13 | 广州三孚新材料科技股份有限公司 | Cyanide-free alkaline copper electroplating solution for steel parts and preparation method thereof |
| CN114874211A (en) * | 2022-03-30 | 2022-08-09 | 西安交通大学 | Imide derivative, preparation method and application in flow battery |
| CN114874211B (en) * | 2022-03-30 | 2023-09-26 | 西安交通大学 | Imide derivative, preparation method and application thereof in flow battery |
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| CN106749241B (en) | 2019-05-24 |
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