CN106977426A - A kind of anacardol phenylurea and preparation method thereof - Google Patents
A kind of anacardol phenylurea and preparation method thereof Download PDFInfo
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- CN106977426A CN106977426A CN201710392801.0A CN201710392801A CN106977426A CN 106977426 A CN106977426 A CN 106977426A CN 201710392801 A CN201710392801 A CN 201710392801A CN 106977426 A CN106977426 A CN 106977426A
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- anacardol
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
- C07C273/1818—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from -N=C=O and XNR'R"
- C07C273/1827—X being H
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/51—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
- C07D303/23—Oxiranylmethyl ethers of compounds having one hydroxy group bound to a six-membered aromatic ring, the oxiranylmethyl radical not being further substituted, i.e.
Abstract
A kind of anacardol phenylurea and preparation method thereof, it is related to a kind of anacardol phenylurea and preparation method thereof.Prepared the present invention seeks to the product anacardol using natural reproducible a kind of new without metal, nontoxic phenyl ureas compound.The structural formula of described anacardol phenylurea is：Method：First, the preparation of glycidyl cashew nut phenolic ether；2nd, the preparation of 1 hydroxyl 2 (2 amino-ethyl) amino-ethyl cashew nut phenolic ether；3rd, the preparation of anacardol phenylurea.Anacardol phenylurea prepared by the present invention is used as agricultural chemicals and epoxy curing agent.
Description
Technical field
The present invention relates to a kind of anacardol phenylurea and preparation method thereof.
Background technology
Phenylurea and its derivative are widely used in composite, agricultural chemicals, medicine and other fields.Phenyl Urea Derivatives
It is good plant growth regulator, Insecticides (tech) ＆ Herbicides (tech), has good application prospect in agriculture and forestry field.Phenylurea is synthesis
The intermediate of sulfa drugs.Phenyl ureas compound particularly in resin composite materials field, is hidden solid as hot type
The accelerator of agent, can be greatly reduced solidification temperature, and in middle low temperature, its catabolite can be consolidated rapidly after coordinating with epoxy resin
Change, obtain the composite that high heat resistance, pliability are good, intensity is high, adhesive force is strong, apply in glass fibre prepreg, powder painting
Expect paint, high enhancement construction sealing materials, leather and adhesive etc..Phenylurea is also used as polyvinyl chloride (PVC) heat
Stabilizer is valued by people.Polyvinyl chloride (PVC) is one of five big general-purpose plastics, with intensity it is high, can be plasticized, corrosion resistant
Erosion, fire retardant, good insulating, it is transparent high the advantages of, its product tool have been widely used.But, there is heat endurance difference in PVC
Shortcoming, must add appropriate heat stabilizer to suppress its thermal degradation during processing.The heat stabilizer industrially commonly used at present is main
There are inorganic lead salt, metallic soap and organotin etc..But, wherein most of conventional kinds are poisonous, this not only limits PVC systems
The application of product, moreover, it is endangered just with the sustainable growth that PVC product is produced using what is caused to environment and work health
It is rapid to deepen.For environmental protection, improve labour health condition, in recent years Europe, the U.S., Japan and domestic successively formulation
And implement policy and regulation of the limitation using poisonous and harmful chemicals.Therefore, find high performance complete heavy metal free (including
Without Zn) " organic group heat stabilizer is the forefront direction of current PVC heat stabilizer research.Phenylurea is had been reported as PVC
The thermal stability of heat stabilizer, transparent performance and electrical insulation capability are good.In a word, phenyl ureas material is widely applied because of it
Property more and more paid attention to, develop new phenyl ureas material and have great importance.It is contemplated that using naturally
Reproducible product anacardol exploitation is a kind of new without the nontoxic phenyl ureas compound of metal.
The content of the invention
The purpose of the present invention is a kind of new without metal, nontoxic phenyl using the product anacardol preparation of natural reproducible
Carbamide compounds.And a kind of anacardol phenylurea and preparation method thereof is provided.
A kind of structural formula of anacardol phenylurea of the present invention is：
Wherein X is H, Cl, Br, I, NO2、SO3H, COOH, OH, aliphatic substitution or aromatic substituents.
The preparation method of above-mentioned anacardol phenylurea, is specifically to carry out according to the following steps：
First, the preparation of glycidyl cashew nut phenolic ether：Anacardol is added in tetrahydrofuran, then adds quality point thereto
Number is 40% NaOH solution, stirs 15min~45min, obtains reaction system, epoxychloropropane is added into reaction system,
The tetrahydrofuran in reaction system is removed after back flow reaction 1.5h~3h, then dichloromethane is added into reaction system, using water
Washing 3~5 times, organic layer is concentrated to give glycidyl cashew nut phenolic ether；The quality of the anacardol and the volume ratio of tetrahydrofuran
For 1g:(8~12) mL；The volume ratio for the NaOH solution that the quality of the anacardol is 40% with mass fraction is 1g:(0.8~
1.2)mL；The mass ratio of the anacardol and epoxychloropropane is 1:(0.15~0.25)；The quality and dichloro of the anacardol
The volume ratio of methane is 1g:(8~12) mL；
2nd, the preparation of 1- hydroxyls -2- (2- amino-ethyls) amino-ethyl cashew nut phenolic ether：By glycidyl cashew nut phenolic ether and 2-
Aminoethyl is added in tetrahydrofuran, is heated to reflux after 1h~3h, is cooled to room temperature, and vacuum distillation removes tetrahydrofuran, then
Dichloromethane is added, uses mass fraction to be washed 3~5 times for the 10% NaCl aqueous solution, organic layer is concentrated to give 1- hydroxyls -2-
(2- amino-ethyls) amino-ethyl cashew nut phenolic ether；The quality of the glycidyl cashew nut phenolic ether and the volume ratio of tetrahydrofuran are
1g:(8~12) mL；The glycidyl cashew nut phenolic ether and the mass ratio of 2- aminoethyls are 1:(0.15~0.25)；The ring
The quality of oxygen propyl group cashew nut phenolic ether and the volume ratio of dichloromethane are 1g:(8~12) mL；
3rd, X- isocyanates, 1- hydroxyls -2- (2- amino-ethyls) amino-ethyl cashew nut phenolic ethers and toluene are mixed, heating
To 60~100 DEG C, after reaction 1h~3h under conditions of temperature is 60~100 DEG C, room temperature is cooled to, white solid is separated out, first
Cleaned again using 70% ethanol solution using water, repeated washing 3~5 times obtains anacardol phenylurea；The X- isocyanates with
The mass ratio of 1- hydroxyls -2- (2- amino-ethyls) amino-ethyl cashew nut phenolic ether is 1:(3~4)；The quality of the X- isocyanates
Volume ratio with dry toluene is 1g:(8~12) mL.
Advantages of the present invention：
The compound of the present invention is as Pesticide use, because longer aliphatic chain can improve the permeability of plant cell.Make
Used for epoxy curing agent, the pliability of epoxy resin can be improved.As PVC heat stabilizer, it can avoid using mesh
Preceding conventional inorganic metal lead salt, organotin etc. contains heavy metal substance.Meanwhile, environmentally friendly reproducible material is employed herein
Anacardol.
Brief description of the drawings
Fig. 1 is glycidyl cashew nut phenolic ether1H NMR spectras；
Fig. 2 is 1- hydroxyls -2- (2- amino-ethyls) amino-ethyl cashew nut phenolic ether1H NMR spectras；
Fig. 3 is anacardol phenylurea1H NMR spectras.
Embodiment
Embodiment one：A kind of structural formula of anacardol phenylurea of present embodiment is：
Wherein X is H, Cl, Br, I, NO2、SO3H, COOH, OH, aliphatic substitution or aromatic substituents.
Embodiment two：A kind of preparation method of anacardol phenylurea of present embodiment, is specifically according to the following steps
Carry out：
First, the preparation of glycidyl cashew nut phenolic ether：Anacardol is added in tetrahydrofuran, then adds quality point thereto
Number is 40% NaOH solution, stirs 15min~45min, obtains reaction system, epoxychloropropane is added into reaction system,
The tetrahydrofuran in reaction system is removed after back flow reaction 1.5h~3h, then dichloromethane is added into reaction system, using water
Washing 3~5 times, organic layer is concentrated to give glycidyl cashew nut phenolic ether；The quality of the anacardol and the volume ratio of tetrahydrofuran
For 1g:(8~12) mL；The volume ratio for the NaOH solution that the quality of the anacardol is 40% with mass fraction is 1g:(0.8~
1.2)mL；The mass ratio of the anacardol and epoxychloropropane is 1:(0.15~0.25)；The quality and dichloro of the anacardol
The volume ratio of methane is 1g:(8~12) mL；
2nd, the preparation of 1- hydroxyls -2- (2- amino-ethyls) amino-ethyl cashew nut phenolic ether：By glycidyl cashew nut phenolic ether and 2-
Aminoethyl is added in tetrahydrofuran, is heated to reflux after 1h~3h, is cooled to room temperature, and vacuum distillation removes tetrahydrofuran, then
Dichloromethane is added, uses mass fraction to be washed 3~5 times for the 10% NaCl aqueous solution, organic layer is concentrated to give 1- hydroxyls -2-
(2- amino-ethyls) amino-ethyl cashew nut phenolic ether；The quality of the glycidyl cashew nut phenolic ether and the volume ratio of tetrahydrofuran are
1g:(8~12) mL；The glycidyl cashew nut phenolic ether and the mass ratio of 2- aminoethyls are 1:(0.15~0.25)；The ring
The quality of oxygen propyl group cashew nut phenolic ether and the volume ratio of dichloromethane are 1g:(8~12) mL；
3rd, X- isocyanates, 1- hydroxyls -2- (2- amino-ethyls) amino-ethyl cashew nut phenolic ethers and toluene are mixed, heating
To 60~100 DEG C, after reaction 1h~3h under conditions of temperature is 60~100 DEG C, room temperature is cooled to, white solid is separated out, first
Cleaned again using 70% ethanol solution using water, repeated washing 3~5 times obtains anacardol phenylurea；The X- isocyanates with
The mass ratio of 1- hydroxyls -2- (2- amino-ethyls) amino-ethyl cashew nut phenolic ether is 1:(3~4)；The quality of the X- isocyanates
Volume ratio with dry toluene is 1g:(8~12) mL.
The preparation method of anacardol phenylurea described in present embodiment is realized by following course of reaction：
Wherein X is H, Cl, Br, I, NO2、SO3H, COOH, OH, aliphatic substitution or aromatic substituents.
Toluene described in present embodiment is by drying process.
Embodiment three：Present embodiment from unlike embodiment two：Anacardol described in step one
Quality and tetrahydrofuran volume ratio be 1g:10mL.It is other identical with embodiment two.
Embodiment four：Present embodiment from unlike embodiment two or three：Waist described in step one
The volume ratio for the NaOH solution that the quality of fruit phenol is 40% with mass fraction is 1g:1mL.Other and embodiment two or three
It is identical.
Embodiment five：Unlike one of present embodiment and embodiment two to four：Institute in step one
The mass ratio for stating anacardol and epoxychloropropane is 1:0.19.It is other identical with one of embodiment two to four.
Embodiment six：Unlike one of present embodiment and embodiment two to five：Institute in step one
It is 1g to state the quality of anacardol and the volume ratio of dichloromethane:10mL.It is other identical with one of embodiment two to five.
Embodiment seven：Unlike one of present embodiment and embodiment two to six：Institute in step 2
It is 1g to state the quality of glycidyl cashew nut phenolic ether and the volume ratio of tetrahydrofuran:10mL.Other and embodiment two to six
One of it is identical.
Embodiment eight：Unlike one of present embodiment and embodiment two to seven：Institute in step 2
The mass ratio for stating glycidyl cashew nut phenolic ether and 2- aminoethyls is 1:0.17.Other phases one of with embodiment two to seven
Together.
Embodiment nine：Unlike one of present embodiment and embodiment two to eight：Institute in step 2
It is 1g to state the quality of glycidyl cashew nut phenolic ether and the volume ratio of dichloromethane:10mL.Other and embodiment two to eight
One of it is identical.
Embodiment ten：Unlike one of present embodiment and embodiment two to nine：Institute in step 3
The mass ratio for stating X- isocyanates and 1- hydroxyls -2- (2- amino-ethyls) amino-ethyl cashew nut phenolic ether is 1:3.15.Other and tool
One of body embodiment two to nine is identical.
Embodiment 11：Unlike one of present embodiment and embodiment two to ten：In step 3
The quality of the X- isocyanates and the volume ratio of toluene are 1g:10mL.It is other identical with one of embodiment two to ten.
Embodiment 12：Present embodiment from unlike embodiment two to one of 11：Step 3
Described in X- isocyanates X be H, Cl, Br, I, NO2、SO3H, COOH, OH, aliphatic substitution or aromatic substituents.Its
It is identical with embodiment two to one of 11.
Beneficial effects of the present invention are verified by tests below：
Experiment one：A kind of preparation method of anacardol phenylurea, is specifically to carry out according to the following steps：
First, the preparation of glycidyl cashew nut phenolic ether：10g anacardols are added in 100mL tetrahydrofurans, then added thereto
Enter the NaOH solution that 10mL mass fractions are 40%, stir 30min, obtain reaction system, epoxy chlorine is added into reaction system
The tetrahydrofuran in reaction system, then the addition 100mL dichloromethanes into reaction system are removed after propane 1.9g, back flow reaction 2h
Alkane, using water washing 3~5 times, organic layer is concentrated to give glycidyl cashew nut phenolic ether；Obtained glycidyl cashew nut phenolic ether
NMR(CDCl3)δ：0.88~0.92 (m3H, CH3), 1.16~1.42 (m, 24H), 1.59 (m, 2H), 2.54~2.57 (m, 2H),
2.71~2.86 (m, 2H), 3.11 (m, 1H), 3.92~4.17 (m, 2H, OCH2CH), 3.92~4.17 (m, 4H), 6.70~
7.21 (m, 4H, ArH)；
2nd, the preparation of 1- hydroxyls -2- (2- amino-ethyls) amino-ethyl cashew nut phenolic ether：By 10g glycidyl cashew nut phenolic ethers
It is added in 100mL tetrahydrofurans, is heated to reflux after 2h with 1.7g2- aminoethyls, be cooled to room temperature, vacuum distillation removes four
Hydrogen furans, adds 100mL dichloromethane, uses mass fraction to be washed 3~5 times for the 10% NaCl aqueous solution, organic layer is dense
Contracting obtains 1- hydroxyls -2- (2- amino-ethyls) amino-ethyl cashew nut phenolic ether；Obtained 1- hydroxyls -2- (2- amino-ethyls) amino second
NMR (the CDCl of base cashew nut phenolic ether3)δ：0.86~0.92 (m, 3H, CH3), 1.03~1.40 (m, 24H), 1.58 (m, 2H), 2.03
~2.56 (m, 4H), 2.60~2.80 (m, 4H), 3.93~3.97 (m, 2H, OCH2), 4.11~4.33 (m, 1H, CH (OH)),
5.26~5.83 (m, 4H), 6.69~7.25 (m, 4H, ArH)；
3rd, by 2gX- isocyanates, 6.3g1- hydroxyls -2- (2- amino-ethyls) amino-ethyl cashew nut phenolic ethers and 100mL first
Benzene is mixed, and is warming up to 80 DEG C, after reaction 2h under conditions of temperature is 80 DEG C, is cooled to room temperature, is separated out white solid, first use
Water is cleaned using 70% ethanol solution again, and repeated washing 3~5 times obtains anacardol phenylurea；The yield of anacardol phenylurea is
95%；NMR (the CDCl of obtained anacardol phenylurea3)δ：0.86~0.92 (m, 3H, CH3), 1.30~1.40 (m, 24H),
1.58 (m, 2H), 2.03~2.56 (m, 2H), 2.60~2.80 (m, 4H), 3.56~3.64 (m, 2H, OCH2), 4.11~4.33
(m, 1H, CH (OH)), 5.26~5.83 (m, 4H), 6.69~7.25 (m, 9H, ArH).
Fig. 1 is glycidyl cashew nut phenolic ether1H NMR spectras；Fig. 2 is 1- hydroxyls -2- (2- amino-ethyls) amino-ethyl
Cashew nut phenolic ether1H NMR spectras；Fig. 3 is anacardol phenylurea1H NMR spectras.It can be seen that and prepare from Fig. 1~Fig. 3
Anacardol phenylurea.
Claims (10)
1. a kind of anacardol phenylurea, it is characterised in that the structural formula of anacardol phenylurea is：
Wherein X is H, Cl, Br, I, NO2、SO3H, COOH, OH, aliphatic substitution or aromatic substituents.
2. a kind of preparation method of anacardol phenylurea as claimed in claim 1, it is characterised in that the system of anacardol phenylurea
Preparation Method, is specifically to carry out according to the following steps：
First, the preparation of glycidyl cashew nut phenolic ether：Anacardol is added in tetrahydrofuran, then adds mass fraction thereto and is
40% NaOH solution, stirs 15min~45min, obtains reaction system, epoxychloropropane is added into reaction system, flows back
The tetrahydrofuran removed after 1.5h~3h in reaction system is reacted, then dichloromethane is added into reaction system, using water washing 3
~5 times, organic layer is concentrated to give glycidyl cashew nut phenolic ether；The quality of the anacardol and the volume ratio of tetrahydrofuran are 1g:
(8~12) mL；The volume ratio for the NaOH solution that the quality of the anacardol is 40% with mass fraction is 1g:(0.8~1.2)
mL；The mass ratio of the anacardol and epoxychloropropane is 1:(0.15~0.25)；The quality and dichloromethane of the anacardol
Volume ratio be 1g:(8~12) mL；
2nd, the preparation of 1- hydroxyls -2- (2- amino-ethyls) amino-ethyl cashew nut phenolic ether：By glycidyl cashew nut phenolic ether and 2- amino
Ethamine is added in tetrahydrofuran, is heated to reflux after 1h~3h, is cooled to room temperature, and vacuum distillation removes tetrahydrofuran, added
Dichloromethane, uses mass fraction to be washed 3~5 times for the 10% NaCl aqueous solution, organic layer is concentrated to give 1- hydroxyl -2- (2-
Amino-ethyl) amino-ethyl cashew nut phenolic ether；The quality of the glycidyl cashew nut phenolic ether and the volume ratio of tetrahydrofuran are 1g:(8
~12) mL；The glycidyl cashew nut phenolic ether and the mass ratio of 2- aminoethyls are 1:(0.15~0.25)；The glycidyl
The quality of cashew nut phenolic ether and the volume ratio of dichloromethane are 1g:(8~12) mL；
3rd, X- isocyanates, 1- hydroxyls -2- (2- amino-ethyls) amino-ethyl cashew nut phenolic ethers and toluene are mixed, is warming up to 60
~100 DEG C, after reaction 1h~3h under conditions of temperature is 60~100 DEG C, room temperature is cooled to, white solid is separated out, first uses
Water is cleaned using 70% ethanol solution again, and repeated washing 3~5 times obtains anacardol phenylurea；The X- isocyanates and 1- hydroxyls
The mass ratio of base -2- (2- amino-ethyls) amino-ethyl cashew nut phenolic ether is 1:(3~4)；The quality of the X- isocyanates is with doing
The volume ratio of dry toluene is 1g:(8~12) mL.
3. a kind of preparation method of anacardol phenylurea according to claim 2, it is characterised in that waist described in step one
The volume ratio for the NaOH solution that the quality of fruit phenol is 40% with mass fraction is 1g:1mL.
4. a kind of preparation method of anacardol phenylurea according to claim 2, it is characterised in that waist described in step one
The mass ratio of fruit phenol and epoxychloropropane is 1:0.19.
5. a kind of preparation method of anacardol phenylurea according to claim 2, it is characterised in that waist described in step one
The quality of fruit phenol and the volume ratio of dichloromethane are 1g:10mL.
6. a kind of preparation method of anacardol phenylurea according to claim 2, it is characterised in that ring described in step 2
Oxygen propyl group cashew nut phenolic ether and the mass ratio of 2- aminoethyls are 1:0.17.
7. a kind of preparation method of anacardol phenylurea according to claim 2, it is characterised in that ring described in step 2
The quality of oxygen propyl group cashew nut phenolic ether and the volume ratio of dichloromethane are 1g:10mL.
8. a kind of preparation method of anacardol phenylurea according to claim 2, it is characterised in that X- described in step 3
The mass ratio of isocyanates and 1- hydroxyls -2- (2- amino-ethyls) amino-ethyl cashew nut phenolic ether is 1:3.15.
9. a kind of preparation method of anacardol phenylurea according to claim 2, it is characterised in that X- described in step 3
The quality of isocyanates and the volume ratio of toluene are 1g:10mL.
10. a kind of preparation method of anacardol phenylurea according to claim 2, it is characterised in that X- described in step 3
X is H, Cl, Br, I, NO in isocyanates2、SO3H, COOH, OH, aliphatic substitution or aromatic substituents.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114656376A (en) * | 2022-04-13 | 2022-06-24 | 常州大学 | Method for synthesizing cardanol modified dicyclopentadiene phenol resin by adopting bisphenol method |
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2017
- 2017-05-27 CN CN201710392801.0A patent/CN106977426A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4010189A (en) * | 1972-12-15 | 1977-03-01 | Imperial Chemical Industries Limited | Alkanolamine derivatives |
| WO2008083054A2 (en) * | 2006-12-26 | 2008-07-10 | Bristol-Myers Squibb Pharma Company | Ligands for cardiac beta1 adrenoceptor for imaging congestive heart failure |
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| KLAUS KOPKA ET AL.: "Design of new β1-selective adrenoceptor ligands as potential radioligands for in vivo Imaging", 《BIOORGANIC & MEDICINAL CHEMISTRY》 * |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114656376A (en) * | 2022-04-13 | 2022-06-24 | 常州大学 | Method for synthesizing cardanol modified dicyclopentadiene phenol resin by adopting bisphenol method |
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