CN103214643A - Method for performing two-step catalyzed synthesis on basic resin by using natural melanin - Google Patents
Method for performing two-step catalyzed synthesis on basic resin by using natural melanin Download PDFInfo
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- CN103214643A CN103214643A CN2013101562463A CN201310156246A CN103214643A CN 103214643 A CN103214643 A CN 103214643A CN 2013101562463 A CN2013101562463 A CN 2013101562463A CN 201310156246 A CN201310156246 A CN 201310156246A CN 103214643 A CN103214643 A CN 103214643A
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- 229920005989 resin Polymers 0.000 title claims abstract description 32
- 239000011347 resin Substances 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims abstract description 17
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 title abstract description 12
- 230000015572 biosynthetic process Effects 0.000 title abstract description 5
- 238000003786 synthesis reaction Methods 0.000 title abstract description 5
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 14
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims abstract description 12
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000463 material Substances 0.000 claims abstract description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims abstract description 6
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 claims abstract description 5
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims abstract description 5
- 229930040373 Paraformaldehyde Natural products 0.000 claims abstract description 4
- 229920002866 paraformaldehyde Polymers 0.000 claims abstract description 4
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 claims abstract 2
- 239000000049 pigment Substances 0.000 claims description 45
- 238000006555 catalytic reaction Methods 0.000 claims description 11
- 239000008367 deionised water Substances 0.000 claims description 10
- 229910021641 deionized water Inorganic materials 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 4
- 229940100630 metacresol Drugs 0.000 claims description 4
- 238000010792 warming Methods 0.000 claims description 4
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 5
- 230000007613 environmental effect Effects 0.000 abstract description 4
- 238000007171 acid catalysis Methods 0.000 abstract description 3
- 238000005815 base catalysis Methods 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 2
- 238000001308 synthesis method Methods 0.000 abstract description 2
- 239000003431 cross linking reagent Substances 0.000 abstract 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- 238000004134 energy conservation Methods 0.000 abstract 1
- 229940015043 glyoxal Drugs 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 238000007599 discharging Methods 0.000 description 8
- HVGQWHMSVYODLJ-GFCCVEGCSA-N melanochrome Natural products CC1(C)Oc2cc3OC(=CC(=O)c3c(O)c2C[C@H]1O)CO HVGQWHMSVYODLJ-GFCCVEGCSA-N 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 230000001133 acceleration Effects 0.000 description 6
- 239000006228 supernatant Substances 0.000 description 6
- 241000238366 Cephalopoda Species 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 241001070941 Castanea Species 0.000 description 3
- 235000014036 Castanea Nutrition 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 235000000023 Auricularia auricula Nutrition 0.000 description 2
- 241001149430 Auricularia auricula-judae Species 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 239000004566 building material Substances 0.000 description 2
- 230000005662 electromechanics Effects 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229920003987 resole Polymers 0.000 description 2
- 210000000582 semen Anatomy 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- 241000157282 Aesculus Species 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- 235000011437 Amygdalus communis Nutrition 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 244000248162 Xanthoceras sorbifolium Species 0.000 description 1
- 235000009240 Xanthoceras sorbifolium Nutrition 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- -1 be adjusted to pH 11 Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000006353 environmental stress Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 235000010181 horse chestnut Nutrition 0.000 description 1
- 230000002434 immunopotentiative effect Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000013520 petroleum-based product Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 239000000718 radiation-protective agent Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 239000005418 vegetable material Substances 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
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- Phenolic Resins Or Amino Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
The invention discloses a method for performing two-step catalyzed synthesis on a basic resin by using natural melanin. According to the method, the natural melanin serves as a basic raw material, the aldehyde material serves as a cross-linking agent, the natural melanin basic resin is synthesized through a two-step catalyzed synthesis method for performing base catalysis and acid catalysis sequentially. In the method, the aldehyde substances which can serve as the cross-linking agents comprise formaldehyde, paraformaldehyde, glyoxal, glutaraldehyde, furfural and the like, and the simple phenolic substances which can be added comprise phenol, resorcinol, m-cresol, xylenol and the like. The basic resin gel synthesized by the method has the advantages of environmental friendliness, energy conservation, simplicity in operation, easy industrial production and the like.
Description
Technical field
The invention belongs to bio-based base resin synthesis technical field, specifically relate to a kind of method with the synthetic base resin of acid catalysis after the base catalysis of natural black pigment elder generation.
Background technology
Base resin is one of important synthesis material of matrix material.Resol is the important base resin of a class wherein, have premium propertiess such as acid and alkali-resistance, cold-resistant, fire-retardant, electric insulation, dimensional stabilizing, have a wide range of applications in fields such as packing, building materials, electromechanics, environmental protection, traffic, become the industrial production indispensable material.Traditional resol is by phenol, Resorcinol, meta-cresol etc. and the crosslinked synthetic of aldehyde material, and these aldehydes matters are petroleum-based products, all belong to Nonrenewable resources.
Melanochrome (Melanin) is the general name that a class extensively is present in the various polymer pigment of the complex structure that is formed by phenols or Benzazole compounds oxypolymerization in the organic sphere.This class pigment is generally black or brown, owing to form the structure difference, also has minority redness, yellow, purple, blueness and green melanochrome.Such material can be organism structural strength or the biological injury of avoiding environment-stress such as ultraviolet ray, ionizing rays, heavy metal, low temperature and high temperature of protection is provided.They are not only a class bright protective agent, antiradiation agent, sequestrant, antioxidant and immunopotentiating agent, but also are class bio-semiconductor materials.At present, melanochrome both can carry out chemosynthesis by the oxidation of tyrosine or derivatives thereof, also can extract in the driven vegetable material, can also utilize microbe fermentation method synthetic.The natural black pigment wide material sources, aboundresources, in hair, eyes, skin and the internal organ of some animals, the pericarp of some plants, plant in skin, the leaf and in sporophore of some fungies or the conidial cell wall content higher.Tealeaves melanochrome and squid ink can batch production productions, also really plant from fragrans seed, horse-chestnut, chestnut shell, civil official to extract the biomass such as the meat of skin, almond peel, Semen Sesami Nigrum kind skin, Pericarpium Musae, squid ink sac, Gallus Domesticus and bone, animal hair, black fungus at present to have obtained melanochrome.Because natural black pigment comes from organism, has recyclability, be bio-based materials therefore as raw material synthetic material, the product of production belongs to the bio-based product, has good application prospects.
Up to now, do not see the method for the synthetic base resin of useful natural black pigment in the prior art as yet.
Summary of the invention
The objective of the invention is at the deficiencies in the prior art, a kind of method of utilizing the synthetic base resin of natural black pigment is provided, using no or little under the situation of simple aldehydes matter, the synthetic base resin of acid catalysis after elder generation's base catalysis, use pollution on the environment thereby effectively reduce simple phenols raw material, and production of resins is to the dependency of oil.
Purpose of the present invention is achieved by the following technical programs.
Except as otherwise noted, percentage ratio of the present invention is mass percent; Umber is a mass fraction.
A kind of method with the synthetic base resin of natural black pigment may further comprise the steps:
(1) natural black pigment aqueous solution preparation: 100 parts of natural black pigments are put into reactor, add 1000～5000 parts deionized water, regulate pH value to 10～14, pigment is fully dissolved make the natural black pigment aqueous solution that concentration is 20～100g/L;
(2) in the natural black pigment aqueous solution that makes, add 140～600 parts of linking agents and 0～500 part of simple aldehydes matter, regulate pH value to 7～12, be warming up to 60～100 ℃, base catalyzed reactions 3～24 hours;
(3) finish the material that obtains behind the base catalyzed reactions and regulate pH value to 1～3 earlier, acid catalyzed reaction 0.5～6 hour under 60～100 ℃ of conditions obtains the natural black pigment base resin again after centrifugal or filtration then.
Described linking agent be formaldehyde, Paraformaldehyde 96, oxalic dialdehyde, one or more arbitrary combination in glutaraldehyde or the furfural; Described simple aldehydes matter is one or more the arbitrary combination in phenol, Resorcinol, meta-cresol or the xylenol.
With respect to prior art, the present invention has the following advantages:
1, this method substitutes or the alternative petroleum-based simple aldehydes matter of part with the natural black pigment of bio-based, with the aldehyde material is linking agent, by the synthetic base resin of two-step catalysis synthesis method, can effectively reduce the consumption of simple phenols raw material in traditional phenolic resin synthesis technique, reduce using pollution that simple aldehydes matter brings environment and the production of resins dependency to oil, is a kind of environmental protection and energy saving and continuable base resin synthetic method.
2, the made natural black pigment base resin of the present invention is gel, but utilizes behind the convection drying, or as the raw material synthetic composite material, is applicable to fields such as packing, building materials, electromechanics, environmental protection, traffic.
Description of drawings
Fig. 1 is embodiment 1～5 described process flow sheet that utilizes the synthetic base resin of natural black pigment two-step catalysis under the simple aldehydes matter situation that do not add;
Fig. 2 is for utilizing the process flow sheet of the synthetic base resin of natural black pigment two-step catalysis under the simple aldehydes matter situation of embodiment 6～8 described interpolations.
Embodiment
Below in conjunction with drawings and Examples the present invention is described in further detail.But drawings and Examples only are used to understand the present invention, are not limited to the technical solution.
Embodiment 1
As shown in Figure 1, get chestnut shell pigment 10g and put into the reactor that volume is 500mL, add the 200mL deionized water, be adjusted to pH 10 with NaOH, pigment is fully dissolved, add 40mL concentration then and be 37% formaldehyde, regulate pH to 11, be warming up to 60 ℃ with NaOH, react after 24 hours and regulate pH to 2 with HCl, continue 60 ℃ of reaction dischargings after 6 hours down, the 5000g centrifugal acceleration is centrifugal 5 minutes behind the naturally cooling, and abandoning supernatant obtains natural black pigment base base resin.
Embodiment 2
As shown in Figure 1, get Semen Sesami Nigrum melanochrome 10g and put into reactor, add the 100mL deionized water, be adjusted to pH 11, pigment is fully dissolved, add 50% glutaraldehyde 60mL then, regulate pH to 12, place under 95 ℃ of constant temperature and reacted 3 hours, use H then with KOH with KOH
2SO
4Regulate pH to 1, continue 95 ℃ of reaction dischargings after 2 hours down, the 5000g centrifugal acceleration is centrifugal 5 minutes behind the naturally cooling, and abandoning supernatant obtains natural black pigment base base resin.
Embodiment 3
As shown in Figure 1, get Wood of Shinyleaf Yellowhorn kind hull melanin 10g and put into reactor, add the 200mL deionized water, be adjusted to pH 12 with NaOH, pigment is fully dissolved, add 99% furfural 60mL then, regulate pH to 10 with NaOH, place under 90 ℃ of constant temperature and reacted 6 hours, use H then
3PO
4Regulate pH to 3, continue 95 ℃ of reaction dischargings after 1 hour down, the 5000g centrifugal acceleration is centrifugal 5 minutes behind the naturally cooling, and abandoning supernatant obtains natural black pigment base base resin.
Embodiment 4
As shown in Figure 1, get squid ink 10g and put into reactor, add the 400mL deionized water, be adjusted to pH 14 with NaOH, pigment is fully dissolved, add the 15g Paraformaldehyde 96 then, regulate pH to 12, place under 60 ℃ of constant temperature and reacted 24 hours with NaOH and HCl, regulate pH to 2 with Phenylsulfonic acid then, continue 60 ℃ of reaction dischargings after 6 hours down, the 5000g centrifugal acceleration is centrifugal 5 minutes behind the naturally cooling, and abandoning supernatant obtains natural black pigment base base resin.
Embodiment 5
As shown in Figure 1, get auricularia auriculajudae melanochrome 10g and put into reactor, add the 400mL deionized water, be adjusted to pH 11 with NaOH, pigment is fully dissolved, add 20mL concentration then and be 37% formaldehyde, 5mL concentration and be 99% furfural and 12mL concentration and be 50% glutaraldehyde, regulate pH to 10 with NaOH and HCl, be warming up to 100 ℃, base catalyzed reactions 3 hours is regulated pH to 2 with oxalic acid then, continues 100 ℃ of reaction dischargings after 0.5 hour down, naturally cooling after-filtration, filter residue are natural black pigment base base resin.
Embodiment 6
As shown in Figure 2, get chestnut shell pigment 10g and put into reactor, add the 300mL deionized water, be adjusted to pH 11 with KOH, pigment is fully dissolved, add Resorcinol 1g, meta-cresol 5g and 37% formaldehyde 50mL then, treat to dissolve fully the back and regulate pH to 10, place under 60 ℃ of constant temperature and reacted 12 hours with KOH, regulate pH to 2 with HCl then, continue 60 ℃ of reaction dischargings after 6 hours down, the 5000g centrifugal acceleration is centrifugal 5 minutes behind the naturally cooling, and abandoning supernatant obtains natural black pigment base base resin.
Embodiment 7
As shown in Figure 2, get squid ink 10g and put into reactor, add the 300mL deionized water, be adjusted to pH 14 with KOH, pigment is fully dissolved, add phenol 2g and 37% formaldehyde 60mL then, treat to dissolve fully the back and regulate pH to 10, place under 60 ℃ of constant temperature and reacted 12 hours, regulate pH to 2 with HCl then, continue 60 ℃ of reaction dischargings after 6 hours down, the 5000g centrifugal acceleration is centrifugal 5 minutes behind the naturally cooling, and abandoning supernatant obtains natural black pigment base base resin.
Embodiment 8
As shown in Figure 2, get auricularia auriculajudae melanochrome 10g and put into the 1000mL reactor, add the 500mL deionized water, be adjusted to pH 11 with KOH, pigment is fully dissolved, add phenol 20g, Resorcinol 30g, 40% oxalic dialdehyde 51mL and 99% furfural 40mL then, use NaCO after treating to dissolve fully
3Regulate pH to 7, place under 90 ℃ of constant temperature and reacted 6 hours, regulate pH to 1 with HCl then, 90 ℃ of reaction dischargings after 2 hours down then, naturally cooling after-filtration, filter residue are natural black pigment base base resin.
Claims (2)
1. method with the synthetic base resin of natural black pigment may further comprise the steps:
(1) natural black pigment aqueous solution preparation: 100 parts of natural black pigments are put into reactor, add 1000～5000 parts deionized water, regulate pH value to 10～14, pigment is fully dissolved make the natural black pigment aqueous solution that concentration is 20～100g/L;
(2) in the natural black pigment aqueous solution that makes, add 140～600 parts of linking agents and 0～500 part of simple aldehydes matter, regulate pH value to 7～12, be warming up to 60～100 ℃, base catalyzed reactions 3～24 hours;
(3) finish the material that obtains behind the base catalyzed reactions and regulate pH value to 1～3 earlier, acid catalyzed reaction 0.5～6 hour under 60～100 ℃ of conditions obtains the natural black pigment base resin again after centrifugal or filtration then.
2. the method with the synthetic base resin of natural black pigment according to claim 1 is characterized in that: described linking agent be formaldehyde, Paraformaldehyde 96, oxalic dialdehyde, one or more arbitrary combination in glutaraldehyde or the furfural; Described simple aldehydes matter is one or more the arbitrary combination in phenol, Resorcinol, meta-cresol or the xylenol.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201310156246.3A CN103214643B (en) | 2013-04-28 | 2013-04-28 | A kind of method that uses natural melanin two-step catalytic synthesis base resin |
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| CN201310156246.3A CN103214643B (en) | 2013-04-28 | 2013-04-28 | A kind of method that uses natural melanin two-step catalytic synthesis base resin |
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| CN103214643A true CN103214643A (en) | 2013-07-24 |
| CN103214643B CN103214643B (en) | 2014-10-01 |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104672430A (en) * | 2015-02-05 | 2015-06-03 | 西南林业大学 | Preparation method of natural-melanin-base epoxy resin |
| CN106140107A (en) * | 2015-03-27 | 2016-11-23 | 西南林业大学 | A kind of method that natural black pigment base resin is prepared in ammonia catalytic thermal solidification |
| CN106146773A (en) * | 2015-03-29 | 2016-11-23 | 西南林业大学 | A kind of method of the natural melanin synthesized base resin of direct acid catalysis |
| CN106146770A (en) * | 2015-03-30 | 2016-11-23 | 西南林业大学 | A kind of method of radical polymerization natural melanin synthesized base resin |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101012340A (en) * | 2007-02-02 | 2007-08-08 | 西北农林科技大学 | Method of extracting and purifying melanin from almond peel |
| CN102757663A (en) * | 2011-04-26 | 2012-10-31 | 中国科学院沈阳应用生态研究所 | Chestnut shell pigment grading method |
-
2013
- 2013-04-28 CN CN201310156246.3A patent/CN103214643B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101012340A (en) * | 2007-02-02 | 2007-08-08 | 西北农林科技大学 | Method of extracting and purifying melanin from almond peel |
| CN102757663A (en) * | 2011-04-26 | 2012-10-31 | 中国科学院沈阳应用生态研究所 | Chestnut shell pigment grading method |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104672430A (en) * | 2015-02-05 | 2015-06-03 | 西南林业大学 | Preparation method of natural-melanin-base epoxy resin |
| CN106140107A (en) * | 2015-03-27 | 2016-11-23 | 西南林业大学 | A kind of method that natural black pigment base resin is prepared in ammonia catalytic thermal solidification |
| CN106140107B (en) * | 2015-03-27 | 2019-06-21 | 西南林业大学 | A kind of ammonia catalysis-thermal curing method for preparing natural melanin-based resin |
| CN106146773A (en) * | 2015-03-29 | 2016-11-23 | 西南林业大学 | A kind of method of the natural melanin synthesized base resin of direct acid catalysis |
| CN106146773B (en) * | 2015-03-29 | 2018-05-04 | 西南林业大学 | A kind of method of the directly natural melanin synthesized base resin of acid catalysis |
| CN106146770A (en) * | 2015-03-30 | 2016-11-23 | 西南林业大学 | A kind of method of radical polymerization natural melanin synthesized base resin |
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