CN103724185B - Anacardol ether acid and preparation method thereof - Google Patents
Anacardol ether acid and preparation method thereof Download PDFInfo
- Publication number
- CN103724185B CN103724185B CN201310710153.0A CN201310710153A CN103724185B CN 103724185 B CN103724185 B CN 103724185B CN 201310710153 A CN201310710153 A CN 201310710153A CN 103724185 B CN103724185 B CN 103724185B
- Authority
- CN
- China
- Prior art keywords
- acid
- cardanol
- anacardol
- preparation
- organic solvent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 0 C*(*Oc1cc(C)ccc1)C(O)=O Chemical compound C*(*Oc1cc(C)ccc1)C(O)=O 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N Cc1cccc(O)c1 Chemical compound Cc1cccc(O)c1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
- C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/46—Polyesters chemically modified by esterification
- C08G63/48—Polyesters chemically modified by esterification by unsaturated higher fatty oils or their acids; by resin acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/676—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paints Or Removers (AREA)
Abstract
The invention provides anacardol ether acid which has a structural formula shown in the specification. The invention also provides a preparation method of the anacardol ether acid. The preparation method comprises the following steps: adding anacardol into a reaction vessel, adding an organic solvent to dissolve anacardol, then adding a metal hydroxide water solution into the reaction vessel, stirring, heating for refluxing, adding chlorinated fatty acid into the reaction vessel, heating for refluxing, carrying out vacuum distillation to remove excess organic solvent, adjusting pH to 1.5-3, adding ethyl acetate to layer, washing an organic phase by using distilled water, then drying by using anhydrous sodium sulfate, filtering to obtain a filter cake, rinsing the filter cake by using ethyl acetate, combining the organic phases, and removing the solvent by distillation to obtain paste solid, namely anacardol ether acid. According to the preparation method, the intermediate anacardol ether acid is synthesized by taking anacardol as a raw material, and then alkyd resin is synthesized by taking the intermediate anacardol ether acid as a raw material, so that not only is the cost of the raw materials reduced, but also the prepared alkyd resin has favorable performances in terms of heat resistance, hardness and the like.
Description
Technical field:
The present invention relates to chemical field, particularly relate to macromolecular material, particularly prepare the intermediate of Synolac, specifically a kind of cardanol ether acid and preparation method.
Background technology:
Synolac is the oily modified polyester resin by polyvalent alcohol, Tetra hydro Phthalic anhydride and lipid acid or oil (fatty acid triglyceride) condensation polymerization.By number and the structure of double bond in lipid acid (or oil) molecule, dryness, semi-drying and non-dryness three class can be divided into.Dry alkyd resin can solidify in atmosphere; Non-dry alkyd resin then will mix with aminoresin, could solidify through heating.In addition also can by the content of lipid acid used (or oil) or Tetra hydro Phthalic anhydride, be divided into short, in, the Synolac of long and extremely long four kinds of oil content.After Synolac film-forming, glossy and toughness, strong adhesion, and there are good wear resistance, weathering resistance and insulativity etc.
Although Synolac has lot of advantages, shortcoming is very important equally, because chain alkyl acid is as oleum lini, and tung oil, the existence of soybean wet goods, makes Synolac toughness have a surplus and undercapacity, and oleum lini, the price of tung oil etc. is more expensive.Cost is higher.Soybean oil, be food plant oil, consumption is too large, can impel its price increase, thus raise resident living cost.Normal oleum lini is the high edible oil of a kind of price comparison, and the oleum lini major part of current industrial application is transgenosis oleum lini, and a large amount of dependence on import, price is higher.Tung oil is special product of China oil plant seeds--the grease that tung oil tree seed squeezes, and due to output and broad-spectrum relation, price remains high always.
Summary of the invention:
The object of the present invention is to provide a kind of cardanol ether acid, described this cardanol ether acid will solve the technical problem that Synolac intensity of the prior art is not enough, cost is high.
This cardanol ether acid of the present invention, its structural formula is as follows:
Present invention also offers a kind of method preparing above-mentioned cardanol ether acid, described method comprises the steps:
1) first cardanol, metal hydroxides and halogenated aliphatic acid is taken according to quality, the mol ratio of described cardanol, metal hydroxides and halogenated aliphatic acid is 1:1.0 ~ 2.0:1 ~ 1.5, metal hydroxides is configured to the aqueous solution that mass percent concentration is 30 ~ 60%, again cardanol is added in a reaction vessel, then the first organic solvent dissolution cardanol is added, the metal hydroxides aqueous solution is added in reaction vessel, stirring at room temperature, after 10 ~ 60 minutes, is heated to 40 ~ 80 DEG C and preferably adopts vigorous stirring mode to stir 10 ~ 60 minutes;
2) halogenated aliphatic acid is added dropwise in reaction vessel, continues heating 100 ~ 120 DEG C, reflux 50 ~ 80 minutes;
3) vacuum boils off the first unnecessary organic solvent in reaction vessel, then add hydrochloric acid and pH value is adjusted to 1.5 ~ 3, add the second organic solvent layering, organic phase distilled water wash, use anhydrous sodium sulfate drying again, filter, filter cake the second organic solvent rinses, and the merging of gained organic phase boils off solvent, and to obtain solid chemical compound be cardanol ether acid.
Further, described halogenated aliphatic acid includes but not limited to Mono Chloro Acetic Acid or bromoacetic acid or iodoacetic acid or 3-chloropropionic acid or 3-bromo-propionic acid or 3-iodopropionic acid or 4-chloro-butyric acid or 4-bromo-butyric acid or 4-iodine butyric acid.
Further, described metal hydroxides includes but not limited to NaOH or KOH.
Further, the first described organic solvent includes but not limited to that ethanol or mass percent concentration are aqueous ethanolic solution or methyl alcohol or toluene or the dimethylbenzene of 90% ~ 98%.
Further, the second described organic solvent includes but not limited to ethyl acetate or toluene or dimethylbenzene or methylene dichloride.
Further, the purity of described cardanol is greater than or equal to 80%.
Reaction equation of the present invention is as follows:
The reaction equation of follow-up Synolac is as follows:
The present invention is using cardanol as raw material, and it is edible not, obtains from the waste producing cashew nut, cheap, greatly reduces use cost.The most important thing is its relative to other grease containing an important group-phenyl ring, phenyl ring to have exploitation high temperature resistant, the material of high strength, strengthens the range of application of traditional alkyd resins, and the Synolac of material hardness other oil synthesis relative increases to some extent simultaneously.
The present invention's cheap cardanol to be raw material make after processing unsaturated fatty acids that unsaturated fatty acids replaces traditional Synolac, not only reduce raw materials cost, and special in benzene ring structure due to cardanol, make the Synolac made heat-resisting, the aspects such as hardness have good performance.
Relative to the comparing of certain traditional Synolac (surperficial pencil hardness is 2B, raw materials used tung oil, oleum lini) being all oil content 50%, hardness ratio the present invention cardanol is that the Synolac of Material synthesis is low, and thus adhesion strength is poor.The present invention is that the alkyd surface pencil hardness of Material synthesis is all at more than HB with cardanol.These vegetables oil are more expensive relative to cardanol ether acid price, and oleum lini can also eat, and raises price in a large number as industrial chemicals consumption, do not utilize resident's food price to stablize.And the main raw material cardanol not edible that the present invention is used, be from discarded cashew nut shell, refine processing, belonging to turns waste into wealth, and the feature of environmental protection is good.
Generally speaking, Synolac of the present invention has greater advantage in price, performance and environmental friendliness.
Embodiment:
Embodiment 1
First with cardanol and the Mono Chloro Acetic Acid cashew nut phenolic ether ethylhexyldithiophosphoric acid that has been Material synthesis, specifically synthesis is as follows for it: add in four-hole boiling flask by cardanol 195g (0.65mol), solubilizing agent 95% ethanol, then by sodium hydroxide (48g, 50% aqueous solution 1.2mol) slowly instills in this system, this reaction is at stirring at room temperature 30min, then reflux 30min, then by Mono Chloro Acetic Acid (122g, 1.3mol) be added drop-wise in system, this reaction continues reflux 60min, then vacuum boils off the unnecessary ethanol in this system, then add hydrochloric acid (1M) and regulate PH>2, add the layering of 300mL ethyl acetate, organic phase distilled water wash three times, then anhydrous sodium sulfate drying is used, filter, filter cake ethyl acetate (60mL) rinses twice, gained organic phase merges and boils off solvent and obtains light yellowish brown cream solid (222.987g, 95.8%).
Its molecular formula is:
MS(m/z）negative：355.2，357.2，359.2
HNMR(CDCl3)，δ11.00（s,1H）,7.29(t,1H),7.07(s,1H),6.81-6.85(q,2H),5.40-5.49(m,4H),4.66(s,2H),2.63(m,4H),2.18(m,4H),1.44(m,2H),1.29(6H,m),0.90(3H,t)
Embodiment 2
222.987g experiment 1 is obtained compound lipid acid, glycerine 93g adds in four-hole boiling flask, dimethylbenzene 45g is heated to 150 DEG C of esterifications, the water produced in esterification process is separated with water trap, after reaching theoretical aquifer yield, cool to 120 DEG C, reflux at adding phthalic enhydride (148g) 150-180 DEG C 5h in batches, after separating the water theory water yield, continue heating, steam dimethylbenzene, monitoring viscosity and acid number, when viscosity (dimethylbenzene opens rare 50%) is at about 7200mPa.S, pH=5 ~ 15, close heating, open rare to about 50% with dimethylbenzene when temperature drops to 120 DEG C, discharging obtains Synolac.
After the Synolac of 50% oil content made adds naphthenic acid rare earth and cobalt naphthenate catalyzer, its index of coated plate is as follows:
Viscosity: 7200mPa.S, solid content: 58%, acid number: 8mgKOH/g
Surface drying: 22min, complete drying: 24h
Surface hardness: >H, surfacing is smooth, Gao Guang.
Embodiment 3
First with cardanol and the 3-chloropropionic acid cashew nut phenolic ether ethylhexyldithiophosphoric acid that has been Material synthesis, specifically synthesis is as follows for it: add in four-hole boiling flask by cardanol 195g (0.65mol), solubilizing agent 95% ethanol, then by sodium hydroxide (48g, 50% aqueous solution 1.2mol) slowly instills in this system, this reaction is at stirring at room temperature 30min, then reflux 30min, then 141.5g3-chloropropionic acid (1.3mol) is added drop-wise in system, this reaction continues reflux 60min, then vacuum boils off the unnecessary ethanol in this system, then add hydrochloric acid (1M) and regulate PH>2, add the layering of 300mL ethyl acetate, organic phase distilled water wash three times, then anhydrous sodium sulfate drying is used, filter, filter cake ethyl acetate (60mL) rinses twice, gained organic phase merges and boils off solvent and obtains light yellow solid (TD2) 231.69g (96.0%).
Its molecular formula is:
MS(m/z）negative：369.2，371.2，373.2
HNMR(CDCl3)，δ11.01（s,1H）,7.29(t,1H),7.07(s,1H),6.81-6.85(q,2H),5.40-5.49(m,4H),4.21(t,2H),2.60(t,2H)2.63(m,4H),2.18(m,4H),1.44(m,2H),1.29(6H,m),0.90(3H,t)
Embodiment 4
231.69g experiment 3 is obtained compound lipid acid (TD2), glycerine 93g adds in four-hole boiling flask, dimethylbenzene 45g is heated to 150 DEG C of esterifications, the water produced in esterification process is separated with water trap, after reaching theoretical aquifer yield, cool to 120 DEG C, reflux at adding phthalic enhydride (148g) 150-180 DEG C 5h in batches, after separating the water theory water yield, continue heating, steam dimethylbenzene, monitoring viscosity and acid number, when viscosity (dimethylbenzene opens rare ~ 50%) is at about 8000mPa.S, pH=5 ~ 15, close heating, open rare to about 50% with dimethylbenzene when temperature drops to 120 DEG C, discharging obtains Synolac.
Character index:
Viscosity: 7600mPa.S, solid content: 56%, acid number: 10mgKOH/g
After the Synolac of 50% oil content made adds naphthenic acid rare earth and cobalt naphthenate catalyzer, its index of coated plate is as follows:
Surface drying: 20min, complete drying: 24h
Surface hardness: >H, surfacing is smooth, Gao Guang.
MS(m/z）negative：369.2，371.2，373.2
HNMR(CDCl3)，δ11.01（s,1H）,7.29(t,1H),7.07(s,1H),6.81-6.85(q,2H),5.40-5.49(m,4H),4.21(t,2H),2.60(t,2H)2.63(m,4H),2.18(m,4H),1.44(m,2H),1.29(6H,m),0.90(3H,t)
Embodiment 5
First with cardanol and the 4-chloro-butyric acid cardanol butyl that has been Material synthesis acid ether, specifically synthesis is as follows for it: add in four-hole boiling flask by cardanol 195g (0.65mol), solubilizing agent 95% ethanol, then by sodium hydroxide (48g, 50% aqueous solution 1.2mol) slowly instills in this system, this reaction is at stirring at room temperature 30min, then reflux 30min, then 159.315g chloro-butyric acid (1.3mol) is added drop-wise in system, this reaction continues reflux 60min, then vacuum boils off the unnecessary ethanol in this system, then add hydrochloric acid (1M) and regulate PH>2, add the layering of 300mL ethyl acetate, organic phase distilled water wash three times, then anhydrous sodium sulfate drying is used, filter, filter cake ethyl acetate (60mL) rinses twice, gained organic phase merges and boils off solvent and obtains light yellow solid (TD2) 240.427g (96%).
Its molecular formula is:
MS(m/z）negative：369.2，371.2，373.2
HNMR(CDCl3)，δ11.01（s,1H）,7.29(t,1H),7.07(s,1H),6.81-6.85(q,2H),5.40-5.49(m,4H),4.21(t,2H),2.60(t,2H)2.63(m,4H),2.30(t,2H),2.18(m,4H),2.08(m,2H)1.44(m,2H),1.29(6H,m),0.90(3H,t)
Embodiment 6
240.427g experiment 5 is obtained compound lipid acid (TD2), glycerine 93g adds in four-hole boiling flask, dimethylbenzene 45g is heated to 150 DEG C of esterifications, the water produced in esterification process is separated with water trap, after reaching theoretical aquifer yield, cool to 120 DEG C, reflux at adding phthalic enhydride (148g) 150-180 DEG C 5h in batches, after separating the water theory water yield, continue heating, steam dimethylbenzene, monitoring viscosity and acid number, when viscosity (dimethylbenzene opens rare ~ 50%) is at about 8000mPa.S, pH=5 ~ 15, close heating, open rare to about 50% with dimethylbenzene when temperature drops to 120 DEG C, discharging obtains Synolac.
Character index:
Viscosity: 9200mPa.S, solid content: 55%, acid number: 9.5mgKOH/g
After the Synolac of 50% oil content made adds naphthenic acid rare earth and cobalt naphthenate catalyzer, its index of coated plate is as follows:
Surface drying: 15min, complete drying: 24h
Surface hardness: >H, surfacing is smooth, Gao Guang.
Certain resin processing plant of Xinhua produce 364-2 medium oil alkyd, fatty acid ester be oleum lini and tung oil, viscosity 8000-10000mPa.S, solid content 48-52%, its room temperature surface drying time: 30-60min, complete drying 48 hours, surface hardness: 2B – HB.
As can be seen from above three examples, the present invention take cardanol as Material synthesis intermediate cardanol ether acid, again with the Synolac that intermediate cardanol ether acid is Material synthesis, its surface hardness is all more than H, and the 364-2 medium oil alkyd hardness that similar product Xinhua Resin Factory, Shanghai produces only has 2B-HB.The present invention successfully uses more cheap cardanol to be that Material synthesis dryness is faster, the Synolac product that surface hardness is higher.
Claims (5)
1. prepare a method for cardanol ether acid, it is characterized in that: comprise the steps:
1) first cardanol is taken according to quality, metal hydroxides and halogenated aliphatic acid, described halogenated aliphatic acid is selected from Mono Chloro Acetic Acid, or bromoacetic acid, or iodoacetic acid, or 3-chloropropionic acid, or 3-bromo-propionic acid, or 3-iodopropionic acid, or 4-chloro-butyric acid, or 4-bromo-butyric acid, or 4-iodine butyric acid, described cardanol, the mol ratio of metal hydroxides and halogenated aliphatic acid is 1:1.0 ~ 2.0:1 ~ 1.5, metal hydroxides is configured to the aqueous solution that mass percent concentration is 30 ~ 60%, again cardanol is added in a reaction vessel, then the first organic solvent dissolution cardanol is added, the metal hydroxides aqueous solution is added in reaction vessel, stirring at room temperature is after 10 ~ 60 minutes, be heated to 40 ~ 80 DEG C and stir 10 ~ 60 minutes,
2) halogenated aliphatic acid is added in reaction vessel, continue to be heated to 100 ~ 120 DEG C, reflux 50 ~ 80 minutes;
3) vacuum boils off the first unnecessary organic solvent in reaction vessel, then add hydrochloric acid and pH value is adjusted to 1.5 ~ 3, add the second organic solvent layering, organic phase distilled water wash, use anhydrous sodium sulfate drying, filtration again, filter cake the second organic solvent rinses, and gained organic phase merges and boils off solvent to obtain solid chemical compound be cardanol ether acid.
2. the preparation method of cardanol ether acid as claimed in claim 1, is characterized in that: described metal hydroxides is selected from NaOH or KOH.
3. the preparation method of cardanol ether acid as claimed in claim 1, is characterized in that: the first described organic solvent is selected from ethanol or methyl alcohol or toluene or dimethylbenzene.
4. the preparation method of cardanol ether acid as claimed in claim 1, is characterized in that: the second described organic solvent is selected from ethyl acetate or toluene or dimethylbenzene or methylene dichloride.
5. the preparation method of cardanol ether acid as claimed in claim 1, is characterized in that: the purity of described cardanol is greater than or equal to 80%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310710153.0A CN103724185B (en) | 2013-12-19 | 2013-12-19 | Anacardol ether acid and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310710153.0A CN103724185B (en) | 2013-12-19 | 2013-12-19 | Anacardol ether acid and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103724185A CN103724185A (en) | 2014-04-16 |
| CN103724185B true CN103724185B (en) | 2015-07-15 |
Family
ID=50448522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310710153.0A Expired - Fee Related CN103724185B (en) | 2013-12-19 | 2013-12-19 | Anacardol ether acid and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103724185B (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6023416A (en) * | 1983-07-20 | 1985-02-06 | Kashiyuu Kk | Synthetic resin and its preparation |
| JPH0699619B2 (en) * | 1986-07-16 | 1994-12-07 | 日本合成化学工業株式会社 | Polyester resin composition |
-
2013
- 2013-12-19 CN CN201310710153.0A patent/CN103724185B/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN103724185A (en) | 2014-04-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103755935B (en) | A kind of preparation method of the Synolac based on cardanol | |
| CN105294543A (en) | Method for preparing weather-proof anti-aging auxiliary agent simultaneously containing hindered phenol and hindered amine structures | |
| CN103145965A (en) | Preparation method of air drying type epoxy modified alkyd resin | |
| CN102351691B (en) | Method for synthesizing adipic acid monoethyl ester | |
| CN103724185B (en) | Anacardol ether acid and preparation method thereof | |
| CN103275308B (en) | Phosphorous flame-retardant water-based alkyd resin and preparation method thereof | |
| CN104529935B (en) | Method for synthesizing ethyl 2-(3-aldehyde-4-isobutyloxyphenyl)-4-methylthiazole-5-formate | |
| CN102391114B (en) | Method for synthesizing n-decanal ester | |
| CN105418903A (en) | Rosin-free high-solid-content alkyd resin and preparation method thereof | |
| CN110283149B (en) | Preparation of biomass diamine, salts thereof, and furanmethanamine and levulinic acid based thereon | |
| CN110776630B (en) | Low-VOC silicon-containing modified waterborne alkyd resin and preparation method thereof | |
| CN103555161B (en) | A kind of preparation technology of water alcohol acid environmental protection paint | |
| CN106540748A (en) | The preparation method of polythiophene tin dioxide composite material | |
| CN102050702B (en) | Method for promoting synthesis of resveratrol by micro waves | |
| CN101220016A (en) | Method for synthesizing 4-hydroxyl coumarin and derivant thereof | |
| CN102351699B (en) | Gulonate and preparation method thereof | |
| CN106673976B (en) | A kind of preparation method of Alpha-hydroxy cyclopentadecanone | |
| CN105949447A (en) | Alkyd resin for polyurethane paint | |
| CN105367416A (en) | Dimethyl succinate preparation method | |
| CN104098540B (en) | A kind of method preparing Zaltoprofen | |
| CN106518671A (en) | Preparation method of butylparaben | |
| CN104211634A (en) | Synthetic method of 2-bromocarbazole | |
| CN105085255A (en) | Synthesis technology for imidazolone herbicide intermediate 2-alkoxy-3-oxo-succinic acid diester | |
| CN115160848B (en) | Preparation method of metal phthalocyanine modified titanium dioxide anti-yellowing agent | |
| CN106748705B (en) | Method for artificially synthesizing curcumin and derivatives thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Anacardol ether acid and preparation method thereof Effective date of registration: 20200601 Granted publication date: 20150715 Pledgee: Quanjiao sub branch of Huishang Bank Co.,Ltd. Pledgor: ANHUI MEIDONG BIOLOGICAL MATERIAL Co.,Ltd. Registration number: Y2020980002657 |
|
| PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20150715 Termination date: 20211219 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |