CN1293115C - Method for preparing epoxy resin in use for light solidified coating material - Google Patents
Method for preparing epoxy resin in use for light solidified coating material Download PDFInfo
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- CN1293115C CN1293115C CNB2004100232077A CN200410023207A CN1293115C CN 1293115 C CN1293115 C CN 1293115C CN B2004100232077 A CNB2004100232077 A CN B2004100232077A CN 200410023207 A CN200410023207 A CN 200410023207A CN 1293115 C CN1293115 C CN 1293115C
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- China
- Prior art keywords
- epoxy
- phase
- resin
- splitting
- epoxy chloropropane
- Prior art date
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- Expired - Lifetime
Links
- 239000011248 coating agent Substances 0.000 title claims abstract description 11
- 238000000576 coating method Methods 0.000 title claims abstract description 11
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 8
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 title claims abstract description 7
- 239000000463 material Substances 0.000 title abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 47
- 229920005989 resin Polymers 0.000 claims abstract description 40
- 239000011347 resin Substances 0.000 claims abstract description 40
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 24
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000004593 Epoxy Substances 0.000 claims abstract description 9
- 239000003513 alkali Substances 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 239000002994 raw material Substances 0.000 claims abstract description 5
- 238000007670 refining Methods 0.000 claims abstract description 5
- -1 ketone compounds Chemical class 0.000 claims description 14
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 8
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 8
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 7
- 239000012535 impurity Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 239000003518 caustics Substances 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000011084 recovery Methods 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 abstract 1
- 238000006266 etherification reaction Methods 0.000 abstract 1
- 238000005191 phase separation Methods 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 238000010792 warming Methods 0.000 description 12
- 238000009835 boiling Methods 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229920003002 synthetic resin Polymers 0.000 description 4
- 239000000057 synthetic resin Substances 0.000 description 4
- YWNYZQTZOONLGU-UHFFFAOYSA-N C(CC)Cl.[O] Chemical compound C(CC)Cl.[O] YWNYZQTZOONLGU-UHFFFAOYSA-N 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 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 2
- 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 2
- 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 2
- 239000012675 alcoholic extract Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical group OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Epoxy Compounds (AREA)
- Epoxy Resins (AREA)
Abstract
The present invention discloses a method for preparing photocurable coating material by using epoxy resin. Bisphenol A and epoxy chloropropane are used as principal raw material, and bisphenol A chlorohydrin bodies are firstly synthesized through etherification and cyclization under the action of alkali. After phase separating compositions are added for phase separation, refining is carried out to obtain epoxy resin products of which the epoxy value is from 0.50 to 0.53 eq/100g and of which the hydroxyl value is from 0.035 to 0.048 mol/100g. The epoxy resin products can be dissolved in methanol to obtain limpid resin-methanol solution and can satisfy specific requirements of photocurable coating material for resin.
Description
Technical field
The present invention relates to the preparation method of a kind of photo-cured coating with Resins, epoxy.
Background technology
In the prior art, the technical scheme that preparation Resins, epoxy adopts usually is: make main raw material with dihydroxyphenyl propane and epoxy chloropropane (ECH), earlier in dihydroxyphenyl propane: the mol ratio of epoxy chloropropane is 1.0: the ratio of (6.0～9.0) under the effect of caustic alkali through catalyst etherifying, cyclisation, synthesis of bisphenol A chloropharin body, reclaim ECH then, refining, extracting and separating, getting oxirane value is the epoxy resin product of 0.51～0.54eq/100g, the hydroxyl value of product is 0.028～0.037mol/100g, the solvability of this resin in methyl alcohol is undesirable, does not reach the particular requirement of photo-cured coating to resin.
Summary of the invention
The objective of the invention is to make and a kind ofly can be dissolved in methyl alcohol, thereby can satisfy the particular requirement of photo-cured coating well, and have the Resins, epoxy of the moulding processability of corresponding excellence.
In order to achieve the above object, the present invention has adopted following technical scheme:
Adopt dihydroxyphenyl propane and epoxy chloropropane to make main raw material, in dihydroxyphenyl propane: the mol ratio of epoxy chloropropane is 1.0: the ratio of (6.0～9.0) under the effect of caustic alkali through catalyst etherifying, cyclisation, synthesis of bisphenol A chloropharin body; After reclaiming ECH, get the crude resin body, the phase-splitting composition that adds crude resin body gross weight 10%～25% carries out phase-splitting to be handled, remove the inorganic impurity that reaches mutually, add alkali then and carry out phase-splitting composition, solubilizing agent extraction, washing, desolventizing in refining reaction, the recovery system, oxirane value be that 0.50～0.53eq/100g, hydroxyl value are the epoxy resin product of 0.035～0.048mol/100g.
Wherein the phase-splitting composition is the mixture of aromatics, ketone compounds, alcohol compound, and the volume parts of three kinds of compounds is in the mixture:
Aromatics: 2～10 parts
Ketone compounds: 8～15 parts
Alcohol compound: 1 part
Aromatics is selected from toluene, dimethylbenzene, benzene; Ketone compounds is selected from acetone, butanone, methyl iso-butyl ketone (MIBK); Alcohol compound is selected from methyl alcohol, ethanol, propylene glycol.
In implementing process of the present invention, concrete reactions steps and working method are:
1, synthesis of bisphenol A chloropharin body: in BPA: ECH: the mol ratio of caustic alkali is 1.0: (6.0～9.0): an amount of reactant of the ratio input of (0.05～0.15) is in reactor, catalyst etherifying is 3 hours under 60 ± 3 ℃ temperature, then 66 ± 3 ℃ temperature and-0.080～-dripped caustic alkali 4 hours under the vacuum of 0.086MPa, its add-on is 1.80～1.90 of a BPA mol ratio, dewater dihydroxyphenyl propane chloropharin body;
2, synthetical resin products: after above-mentioned dihydroxyphenyl propane chloropharin body taken off ECH, the crude resin body.The phase-splitting composition that adds crude resin body total amount 10%～25% carries out phase-splitting to the crude resin body to be handled, add caustic alkali at resin in mutually then, its add-on is 0.40～0.55 of a dihydroxyphenyl propane mol ratio, reaction under 85～88 ℃ the temperature about 1 hour, phase-splitting composition in the recovery system, solubilizing agent carries out extracting and separating, washing, recovery solvent to system again, and promptly getting oxirane value is that 0.50～0.53eq/100g, hydroxyl value are the epoxy resin product of 0.035～0.048mol/100g.
In implementing process of the present invention, during synthesis of bisphenol A chloropharin body, the consumption of strict control epoxy chloropropane, with dihydroxyphenyl propane: the mol ratio of epoxy chloropropane is 1.0: be advisable (6.0～9.0), not too high or too low, otherwise, the quality of product and the physical and mechanical properties of finished product can be influenced; When carrying out the phase-splitting processing, the consumption of phase-splitting composition is 10%～25% of a crude resin body gross weight, to guarantee that the resin physical efficiency contacts with the phase-splitting composition fully, inorganic other impurity that reaches mutually can be separated into suitable effectively, do not add too much, otherwise can influence the reaction of the latter half, increase operational difficulty, increase load.
Phase-splitting is handled and has been adopted the similar principle that mixes, crude resin can be dissolved in the organic composite well, inorganics and other impurity can be separated well, formed uniform resin liquid, make between the molecular resin chain and can contact fully, increased the polyreaction between the molecular resin chain, the alcoholic extract hydroxyl group content in the sold resin is increased.
Compared with prior art, the present invention has following tangible advantage:
1, the consistency of Fa Ming resin and methyl alcohol is relatively good, is difficult for producing turbid phenomenon.
According to relevant bibliographical information, the solubility parameters of Resins, epoxy is about 10.2, and methyl alcohol is 14.28, differs bigger, and the principle close according to solubility parameters, Resins, epoxy and methyl alcohol are that consistency is bad in itself.
The present invention mainly sets about from technical recipe, processing condition, reaction principle, by optimization production technology, select rational refining reaction system, make various structure components and molecular weight in the synthetic Resins, epoxy that rational distribution be arranged, mainly make the increases such as cl content reduction, molecular weight and hydroxy radical content in the resin, thereby the solubility parameters of resin is improved, and with the close together of methyl alcohol solubility parameters, consistency improves.
Resin before the technology and resin of the present invention and the anhydrous methanol ratio according to resin/methyl alcohol=1g/10ml will be improved, respectively get the methyl alcohol of 10g resin and 100ml, add in the transparent vial, in 25～40 ℃ water bath with thermostatic control, stir, do the contrast experiment, the result is as follows:
| Resin/methyl alcohol=1g/10ml | Improve the preceding resin of technology | Resin of the present invention |
| 40℃ | Little mixing | Transparent |
| 30℃ | Muddy | Transparent |
| 25℃ | Muddy | Transparent |
2, the rosin products quality is good, can satisfy the particular requirement of photo-cured coating to resin.
This rosin products is dissolved in methyl alcohol, can obtain as clear as crystal resin-methanol solution, uses more conveniently, and use properties is relatively good, does not ftracture during as the water curtain test of photo-cured coating, and coating is during as finish paint, and the surface evenly.
3, technology is simple, and is easy to operate.Its main technique does not change, and just existing technology is improved, and is simple.The phase-splitting composition that adopts is the mixture of aromatic compound, ketone compounds, alcohol compound composition, and each raw material is cheap and easy to get, and cost is low.
Embodiment
Below by specific embodiment embodiments of the present invention are described in further detail:
Embodiment 1:
At volume is 1000ml, be furnished with that to add 0.75mol (171g) dihydroxyphenyl propane, the epoxy chloropropane (417g) of 4.5mol99.9%, 0.0375mol concentration in the four-hole boiling flask of thermometer, agitator, reflux exchanger be 45% NaOH (3.3g) solution, be warming up to 60 ℃ after being heated to 55 ℃ voluntarily, reaction is 3 hours under this temperature.After frame reinstalls stream phase splitter, dropping funnel, NaOH (120g) solution that in dropping funnel, adds 1.35mol concentration 45%, evenly drip in 4 hours, react under-0.082MPa the vacuum tightness at 66 ± 3 ℃, pressure, epoxy chloropropane and water form azeotrope, constantly from reactor, steams, and phase-splitting in phase splitter, the epoxy chloropropane of lower floor is back in the reactor in the phase splitter, discharges the water on upper strata.After being added dropwise to complete, NaOH is warming up to 100 ℃ gradually, dehydration, improve vacuum more gradually to-0.098MPa, be warming up to 150 ℃, decylization oxygen chloropropane (the about altogether 250ml of epoxy chloropropane+water) is about half an hour, system is cooled to below 100 ℃ after replying normal pressure, add phase-splitting composition (toluene 5.3ml, methyl iso-butyl ketone (MIBK) 39ml, methyl alcohol 2.7ml) 47ml, 75 ± 3 ℃ are stirred half an hour down, material are poured in the separating funnel, tell the inorganic substance and the impurity of lower floor, the organic substance on upper strata is poured in the four-hole boiling flask, and adding 0.3mol concentration is 45% NaOH (26.7g) solution, 73g water, adjust the temperature to about 85 ℃ and reacted 1 hour, reclaim the phase-splitting composition, add the 260ml solvent again, add water 100ml and stirred 5 minutes, leave standstill after 30 minutes and remove out lower layer of water, add an amount of 10%H
3PO
4Being neutralized to reactant PH is 7, stirs, removes out lower layer of water behind the standing demix, and reaction mixture is warming up to 160 ℃, be decompressed to-the 0.098MPa desolventizing gets the 240g resin half an hour.Synthetic resin quality index is:
Oxirane value: 0.506eq/100g
Viscosity: 13800mPa.s (25 ℃)
Organochlorine: 234ppm
Fugitive constituent: 0.17%
Hydroxyl value: 0.043mol/100g
Embodiment 2:
At volume is 1000ml, be furnished with that to add 0.75mol (171g) dihydroxyphenyl propane, the epoxy chloropropane (625g) of 6.75mol99.9%, 0.11mol concentration in the four-hole boiling flask of thermometer, agitator, reflux exchanger be 45% NaOH (9.78g) solution, be warming up to 60 ℃ after being heated to 55 ℃ voluntarily, reaction is 3 hours under this temperature.After frame reinstalls stream phase splitter, dropping funnel, NaOH (127.1g) solution that in dropping funnel, adds 1.43mol concentration 45%, evenly drip in 4 hours, react under-0.082MPa the vacuum tightness at 66 ± 3 ℃, pressure, epoxy chloropropane and water form azeotrope, constantly from reactor, steams, and phase-splitting in phase splitter, the epoxy chloropropane of lower floor is back in the reactor in the phase splitter, discharges the water on upper strata.After being added dropwise to complete, NaOH is warming up to 100 ℃ gradually, dehydration, improve vacuum more gradually to-0.098MPa, be warming up to 150 ℃, decylization oxygen chloropropane (the about altogether 460ml of epoxy chloropropane+water) is about half an hour, system is cooled to below 100 ℃ after replying normal pressure, add phase-splitting composition (dimethylbenzene 62ml, methyl iso-butyl ketone (MIBK) 50ml, ethanol 6ml) 118ml, 75 ± 3 ℃ are stirred half an hour down, material are poured in the separating funnel, tell the inorganic substance and the impurity of lower floor, the organic substance on upper strata is poured in the four-hole boiling flask, and adding 0.41mol concentration is 45% NaOH (36.7g) solution, 83g water, adjust the temperature to about 85 ℃ and reacted 1 hour, after reclaiming the phase-splitting composition, add the 260ml solvent again, add water 100ml and stirred 5 minutes, leave standstill after 30 minutes and remove out lower layer of water, add an amount of 10%H
3PO
4Being neutralized to reactant PH is 7, stirs, removes out lower layer of water behind the standing demix, and reaction mixture is warming up to 160 ℃, be decompressed to-the 0.098MPa desolventizing gets the 245g resin half an hour.Synthetic resin quality index is:
Oxirane value: 0.528eq/100g
Viscosity: 13500mPa.s (25 ℃)
Organochlorine: 224ppm
Fugitive constituent: 0.18%
Hydroxyl value: 0.038mol/100g
Embodiment 3:
At volume is 1000ml, be furnished with that to add 0.75mol (171g) dihydroxyphenyl propane, the epoxy chloropropane (521g) of 5.63mol99.9%, 0.075mol concentration in the four-hole boiling flask of thermometer, agitator, reflux exchanger be 45% NaOH (6.67g) solution, be warming up to 60 ℃ after being heated to 55 ℃ voluntarily, reaction is 3 hours under this temperature.After frame reinstalls stream phase splitter, dropping funnel, NaOH (123.6g) solution that in dropping funnel, adds 1.39mol concentration 45%, evenly drip in 4 hours, react under-0.082MPa the vacuum tightness at 66 ± 3 ℃, pressure, epoxy chloropropane and water form azeotrope, constantly from reactor, steams, and phase-splitting in phase splitter, the epoxy chloropropane of lower floor is back in the reactor in the phase splitter, discharges the water on upper strata.After being added dropwise to complete, NaOH is warming up to 100 ℃ gradually, dehydration, improve vacuum more gradually to-0.098MPa, be warming up to 150 ℃, decylization oxygen chloropropane (the about altogether 355ml of epoxy chloropropane+water) is about half an hour, system is cooled to below 100 ℃ after replying normal pressure, add phase-splitting composition (benzene 26ml, butanone 52ml, propylene glycol 4ml) 82ml, 75 ± 3 ℃ are stirred half an hour down, material are poured in the separating funnel, tell the inorganic substance and the impurity of lower floor, the organic substance on upper strata is poured in the four-hole boiling flask, and adding 0.36mol concentration is 45% NaOH (32.0g) solution, 78g water, adjust the temperature to about 85 ℃ and reacted 1 hour, after reclaiming the phase-splitting composition, add the 260ml solvent again, add water 100ml and stirred 5 minutes, leave standstill after 30 minutes and remove out lower layer of water, add an amount of 10%H
3PO
4Being neutralized to reactant PH is 7, stirs, removes out lower layer of water behind the standing demix, and reaction mixture is warming up to 160 ℃, be decompressed to-the 0.098MPa desolventizing gets the 242g resin half an hour.Synthetic resin quality index is:
Oxirane value: 0.515eq/100g
Viscosity: 13600mPa.s (25 ℃)
Organochlorine: 234ppm
Fugitive constituent: 0.16%
Hydroxyl value: 0.040mol/100g
Claims (2)
1, a kind of photo-cured coating preparation method of Resins, epoxy, it is characterized in that: adopt dihydroxyphenyl propane and epoxy chloropropane to make main raw material, in dihydroxyphenyl propane: the mol ratio of epoxy chloropropane is 1.0: the ratio of (6.0～9.0) under the effect of caustic alkali through catalyst etherifying, cyclisation, synthesis of bisphenol A chloropharin body; After reclaiming epoxy chloropropane, get the crude resin body, the phase-splitting composition that adds crude resin body gross weight 10%～25% carries out phase-splitting to be handled, remove the inorganic impurity that reaches mutually, add alkali then and carry out phase-splitting composition, solubilizing agent extraction, washing, desolventizing in refining reaction, the recovery system, oxirane value be that 0.50～0.53eq/100g, hydroxyl value are the epoxy resin product of 0.035～0.048mol/100g;
Wherein the phase-splitting composition is the mixture of aromatics, ketone compounds, alcohol compound, and the volume parts of three kinds of compounds is in the mixture:
Aromatics: 2～10 parts
Ketone compounds: 8～15 parts
Alcohol compound: 1 part.
2, method according to claim 1 is characterized in that: aromatics is selected from toluene, dimethylbenzene, benzene; Ketone compounds is selected from acetone, butanone, methyl iso-butyl ketone (MIBK); Alcohol compound is selected from methyl alcohol, ethanol, propylene glycol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100232077A CN1293115C (en) | 2004-05-12 | 2004-05-12 | Method for preparing epoxy resin in use for light solidified coating material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100232077A CN1293115C (en) | 2004-05-12 | 2004-05-12 | Method for preparing epoxy resin in use for light solidified coating material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1696170A CN1696170A (en) | 2005-11-16 |
| CN1293115C true CN1293115C (en) | 2007-01-03 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2004100232077A Expired - Lifetime CN1293115C (en) | 2004-05-12 | 2004-05-12 | Method for preparing epoxy resin in use for light solidified coating material |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1293115C (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102618144A (en) * | 2012-03-26 | 2012-08-01 | 江苏冠军涂料科技集团有限公司 | Special primer for heavy-duty machinery |
| CN103756459A (en) * | 2014-01-22 | 2014-04-30 | 青岛金海鲨光电科技有限公司 | Nano optical waterproof glue and nano waterproof lamp employing same |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1118788A (en) * | 1994-01-26 | 1996-03-20 | 布兰科尼尔有机合成研究院 | Method to manufacture liquid epoxy resins |
| CN1133305A (en) * | 1994-10-17 | 1996-10-16 | 布兰科尼尔有机合成研究院 | Process for making solid epoxy resin |
| JPH09328534A (en) * | 1996-06-11 | 1997-12-22 | Nippon Steel Chem Co Ltd | High-purity heat-resistant epoxy resin and molding material for electronic material |
-
2004
- 2004-05-12 CN CNB2004100232077A patent/CN1293115C/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1118788A (en) * | 1994-01-26 | 1996-03-20 | 布兰科尼尔有机合成研究院 | Method to manufacture liquid epoxy resins |
| CN1133305A (en) * | 1994-10-17 | 1996-10-16 | 布兰科尼尔有机合成研究院 | Process for making solid epoxy resin |
| JPH09328534A (en) * | 1996-06-11 | 1997-12-22 | Nippon Steel Chem Co Ltd | High-purity heat-resistant epoxy resin and molding material for electronic material |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1696170A (en) | 2005-11-16 |
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