CN107892671A - Cardanol derivative and application thereof - Google Patents

Cardanol derivative and application thereof Download PDF

Info

Publication number
CN107892671A
CN107892671A CN201711110811.7A CN201711110811A CN107892671A CN 107892671 A CN107892671 A CN 107892671A CN 201711110811 A CN201711110811 A CN 201711110811A CN 107892671 A CN107892671 A CN 107892671A
Authority
CN
China
Prior art keywords
compound
formulas
cardanol derivative
dmso
nmr
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.)
Granted
Application number
CN201711110811.7A
Other languages
Chinese (zh)
Other versions
CN107892671B (en
Inventor
王利民
黄蒙恩
车飞
张景清
韩建伟
赵敏
田禾
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
SHANGHAI BANGGAO CHEMICAL CO Ltd
East China University of Science and Technology
Original Assignee
SHANGHAI BANGGAO CHEMICAL CO Ltd
East China University of Science and Technology
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by SHANGHAI BANGGAO CHEMICAL CO Ltd, East China University of Science and Technology filed Critical SHANGHAI BANGGAO CHEMICAL CO Ltd
Priority to CN201711110811.7A priority Critical patent/CN107892671B/en
Publication of CN107892671A publication Critical patent/CN107892671A/en
Application granted granted Critical
Publication of CN107892671B publication Critical patent/CN107892671B/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The present invention relates to a kind of Cardanol derivative and application thereof.The Cardanol derivative is compound shown in Formulas I.Cardanol derivative provided by the invention can be used as cationic surfactant.In Formulas I, R1For C15Chain alkyl, A be divalence C2~C4Chain alkyl, R2For the C of monovalence or divalence3~C17Nitrogen heterocyclic ring cation base, n are 1 or 2.

Description

Cardanol derivative and application thereof
Technical field
The present invention relates to a kind of Cardanol derivative and application thereof.
Background technology
Anacardol is a kind of plant or paddy of the purification from cashew nut shell oil (Cashew Nut Shell Liquid, CNSL) Material resource renewable raw materials.Anacardol includes four kinds of different meta alkyl phenols.Due to having on four kinds of monomer molecules of anacardol It is a variety of to can be used for chemically derived functional group：Carbon-carbon double bond on phenolic hydroxyl group, phenyl ring and carbon long-chain, anacardol are one non- Often with the molecular structure for having derivative potentiality.
The content of the invention
The present inventor it has been investigated that：It is C by meta15Chain alkyl the anacardol chain that passes through certain length Shape alkyl is connected with the aromatic compound (such as pyridine, N- methylimidazoles or 4,4'-Bipyridine) containing N, obtains a kind of structure Novel Cardanol derivative.Resulting Cardanol derivative has relatively low CMC value and γCMCValue, can be used as cation form Face activating agent uses.
A purpose of the invention is, there is provided a kind of novel Cardanol derivative of structure, the Cardanol derivative are Compound shown in Formulas I：
In Formulas I, R1For C15Chain alkyl, A be divalence C2~C4Chain alkyl, R2For the C of monovalence or divalence3~C17 Nitrogen heterocyclic ring cation (base), n are 1 or 2.
Another object of the present invention is, discloses a kind of purposes of above-mentioned cashew nut phenolic compound (compound shown in Formulas I). Application of the compound as cationic surfactant i.e. shown in Formulas I.
In addition, a further object of the invention is, there is provided a kind of method of compound shown in formula I.Methods described Comprise the following steps：
(1) with anacardol (compound shown in Formula II) for initiation material, compound and halogenated hydrocarbons (Y-A-Y) as shown in Formula II Reaction, shown in formula III the step of compound；And
(2) compound and respective compound (HR as shown in formula III2) reaction, obtain object (compound shown in Formulas I) Step.
Wherein, R1, R2With described previously identical, Y is halogen (F, Cl, Br or I) for definition with A.
Brief description of the drawings
Fig. 1 provide the surface tension concentration curve of Cardanol derivative for the present invention；
Wherein, transverse axis represents concentration (mol/L), and the longitudinal axis represents surface tension (mN/m).
Embodiment
In a preferable technical scheme of the invention, R2For one of following groups, (wherein curve mark part is substitution Position)：
In a preferable technical scheme of the invention, the method for compound shown in formula I of the present invention, specific bag Include following steps：
(1) under the conditions of having alkali compounds (potassium carbonate etc.) existing, compound and halogenated hydrocarbons (Y-A- as shown in Formula II Y) in organic solvent (such as acetone), kept at least 12 hours in reflux state, cooling, filtering and concentration filtrate are remaining Thing is purified (such as column chromatography), obtains compound shown in formula III；
(2) by compound shown in formula III and respective compound (HR2) it is placed in anhydrous organic solvent (such as dry toluene, anhydrous Acetonitrile or dry DMF etc.) in, at least 12 hours (preferably 12 to twenty four hours) are reacted in 80 DEG C~110 DEG C, are stopped After reaction, if any Precipitation, then cold filtration, filter cake are object after recrystallization；Such as without Precipitation, concentration reaction Liquid, precipitating reagent (such as n-hexane or absolute ether) to Precipitation, filtering, filter cake is added into residue is after recrystallization For object.
With reference to specific embodiment, the present invention is expanded on further.It should be understood that these embodiments are merely to illustrate the present invention Rather than limitation the scope of the present invention.The experimental method of unreceipted actual conditions in the following example, generally marked according to country Quasi- measure.If without corresponding national standard, built according to general international standard, normal condition or according to manufacturer The condition of view is carried out.
Embodiment 1
The preparation of compound shown in Formulas I a：
(1) the bromo- 2- butylene (30mmol, 3equiv) of trans- Isosorbide-5-Nitrae-two, Anhydrous potassium carbonate (60mmol, 6equiv) are dissolved in In acetone, the acetone soln of pentadecyl phenol between (10mmol, 1equiv) is added, backflow is overnight.After reaction terminates, filter, will Filtrate is outstanding to go 2/3rds, dry sample processed, silicagel column post separation (eluent is pure petroleum ether), obtains compound shown in formula III a；
(2) N- methylimidazoles (0.55mmol, 1.1equiv) are dissolved in dry toluene, are slowly added to formula III a shownization Compound (0.5mmol, 1equiv), 100 DEG C of reaction overnights.Decompression is outstanding to remove solvent, adds n-hexane, there is brown solid precipitation, mistake Filter obtains brown solid, washs (3 × 15mL) three times with n-hexane, methanol/ethyl acetate is recrystallized to give chemical combination shown in Formulas I a Thing (63%).
1H NMR(400MHz,DMSO)δ9.18(s,1H),7.74-7.80(m,2H),7.13-7.20(m,1H),6.70- 6.80 (m, 3H), 5.95-6.11 (m, 2H), 4.90 (d, J=8.0Hz, 2H), 4.56 (d, J=4.0Hz, 2H), 3.87 (s, 3H), 2.51-2.56 (m, 2H), 1.45-1.57 (m, 2H), 1.15-1.32 (m, 24H), 0.84 (t, J=8.0Hz, 3H)
13C NMR(101MHz,DMSO)δ157.98,144.00,136.49,131.74,129.20,125.40,123.76, 122.19,120.81,114.57,111.57,66.54,49.70,35.79,35.13,31.25,30.83,28.98,28.82, 28.66,22.06,13.91.
HRMS(ESI-TOF)m/z:[M-Br]+Calcd for C29H47N2O 439.3683；Found 439.3681.
Embodiment 2
The preparation of compound shown in Formulas I b：
Pyridine (1.10mmol, 1.1equiv) is dissolved in dry toluene, is slowly added to compound shown in formula III a (1.0mmol, 1equiv), 108 DEG C of reaction overnights.After reaction terminates, decompression is outstanding to remove solvent, adds absolute ether, there is solid analysis Go out, be filtrated to get solid, washed (3 × 15mL) three times with absolute ether, methanol/ethyl acetate is recrystallized to give Formulas I b shownization Compound (75%).
1H NMR (400MHz, DMSO) δ 9.10 (d, J=4.0Hz, 2H), 8.61-8.68 (m, 1H), 8.16-8.24 (m, 2H), 7.12-7.19 (m, 1H), 6.70-6.80 (m, 3H), 6.11-6.27 (m, 2H), 5.35 (d, J=8.0Hz, 2H), 4.59 (d, J=4.0Hz, 2H), 2.50-2.57 (m, 2H), 1.46-1.58 (m, 2H), 1.16-1.32 (m, 24H), 0.85 (t, J= 8.0Hz,3H).
13C NMR(101MHz,DMSO)δ157.91,145.84,144.66,143.99,130.21,129.19,128.21, 124.93,120.85,114.60,111.62,66.45,61.33,35.13,31.26,30.83,28.98,28.82,28.67, 22.06,13.91.
HRMS(ESI-TOF)m/z:[M-Br]+Calcd for C30H46NO 436.3574；Found 436.3569.
Embodiment 3
The preparation of compound shown in Formulas I c：
(1) divided by Isosorbide-5-Nitrae-dibromobutane alternative embodiment 1 outside the trans- bromo- 2- butylene of Isosorbide-5-Nitrae-two, other conditions and step with The step of embodiment 1 (1), is identical, obtains compound shown in formula III b；
(2) compound (1mmol, 1equiv) shown in formula III b and 4,4'-Bipyridine (5mmol, 5equiv) are dissolved in nothing In water DMF, 80 DEG C are reacted 22 hours, are cooled to room temperature, are filtrated to get precipitation, methanol/ethyl acetate is recrystallized to give Formulas I c institutes Show compound (59%).
1H NMR (400MHz, DMSO) δ 9.18 (d, J=4.0Hz, 2H), 8.85 (d, J=8.0Hz, 2H), 8.54 (d, J =8.0Hz, 2H), 8.01 (d, J=4.0Hz, 2H), 7.12-7.19 (m, 1H), 6.70-6.78 (m, 3H), 4.82 (t, J= 8.0Hz, 2H), 4.07 (t, J=4.0Hz, 2H), 2.56 (t, J=8.0Hz, 2H), 2.27-2.37 (m, 2H), 1.90-1.99 (m, 2H), 1.53-1.65 (m, 2H), 1.25-1.39 (m, 24H), 0.92 (t, J=8.0Hz, 3H)
13C NMR(101MHz,DMSO)δ158.39,152.28,150.97,145.34,143.93,140.83,129.16, 125.39,121.88,120.60,114.39,111.51,66.48,60.11,35.16,31.25,30.96,28.96,28.81, 28.65,27.68,25.31,22.06,13.92.
HRMS(ESI-TOF)m/z:[M-Br]+Calcd for C35H51N2O 515.3996；Found 515.3998.
Embodiment 4
The preparation of compound shown in Formulas I d：
Compound (1.0mmol, 1equiv) shown in formula III a and 4,4'-Bipyridine (5mmol, 5equiv) are dissolved in anhydrous In DMF, 80 DEG C are reacted 22 hours, are cooled to room temperature, add absolute ether, are produced precipitation, are filtrated to get precipitation, absolute ether is washed (3 × 20mL) three times, obtain compound (70%) shown in Formulas I d.
1H NMR (400MHz, DMSO) δ 9.21 (d, J=4.0Hz, 2H), 8.88 (d, J=4.0Hz, 2H), 8.66 (d, J =8.0Hz, 2H), 8.04 (d, J=4.0Hz, 2H), 7.14-7.21 (m, 1H), 6.73-6.80 (m, 3H), 6.13-6.30 (m, 2H), 5.35 (d, J=8.0Hz, 2H), 4.61 (d, J=4.0Hz, 2H), 2.53-2.58 (m, 2H), 1.45-1.58 (m, 2H), 1.15-1.30 (m, 24H), 0.88 (t, J=8.0Hz, 3H)
13C NMR(101MHz,DMSO)δ157.93,152.62,150.93,145.24,144.60,144.02,133.80, 129.22,125.56,124.96,121.93,120.89,114.57,111.67,66.47,61.00,35.13,31.25, 30.83,28.96,28.80,28.66,22.06,13.92.
HRMS(ESI-TOF)m/z:[M-Br]+Calcd for C35H49N2O 513.3839；Found 513.3832.
Embodiment 5
The preparation of compound shown in Formulas I e：
4,4'-Bipyridine (10mmol, 1equiv) is dissolved in dichloromethane, iodomethane (12mmol, 1.2equiv) is dissolved in Dichloromethane, the dichloromethane solution of iodomethane is instilled to the dichloromethane solution of 4,4'-Bipyridine, flowed back 1 hour.Reaction knot Room temperature is cooled to after beam, is filtrated to get precipitation, recrystallizing methanol obtains compound A；
Compound (0.6mmol, 1.2equiv) shown in compound A (0.5mmol, 1equiv) and formula III a is dissolved in anhydrous In acetonitrile, being reacted 24 hours under argon gas protection, be filtrated to get precipitation, sediment washs (3 × 15mL) three times with anhydrous acetonitrile, Acetone recrystallization obtains compound (46%) shown in Formulas I e.
1H NMR (400MHz, DMSO) δ 9.39 (d, J=8.0Hz, 2H), 9.31 (d, J=4.0Hz, 2H), 8.82 (d, J =4.0Hz, 2H), 8.78 (d, J=8.0Hz, 2H), 7.14-7.23 (m, 1H), 6.72-6.85 (m, 3H), 6.15-6.34 (m, 2H), 5.42 (d, J=4.0Hz, 2H), 4.62 (d, J=4.0Hz, 2H), 4.46 (s, 3H), 2.51-2.56 (m, 2H), 1.46- 1.47 (m, 2H), 1.16-1.32 (m, 24H), 0.85 (t, J=8.0Hz, 3H)
13C NMR(101MHz,DMSO)δ157.93,148.92,146.62,144.05,134.05,129.94,126.72, 124.71,120.91,114.58,111.59,66.46,61.46,48.03,35.14,31.25,30.08,28.98,28.82, 28.66,22.06,13.91.
HRMS(ESI-TOF)m/z:[M-Br-I]2+Calcd for[C36H52N2O]2+264.2034；Found 264.2037.
Embodiment 6
The preparation of compound shown in Formulas I f：
The addition 4,4'-Bipyridine (7mmol, 7equiv) in pressure pipe, benzyl bromine (1mmol, 1equiv), acetonitrile, 80 DEG C Reaction 24 hours.After reaction terminates, room temperature is cooled to, is filtrated to get solid, solid (3 × 20mL) three times is washed with acetonitrile, obtains To compound B
By compound B (0.5mmol, 1equiv), compound (0.6mmol, 1.2equiv) shown in formula III a is dissolved in anhydrous In acetonitrile, being reacted 24 hours under argon gas protection, be filtrated to get precipitation, sediment washs (3 × 15mL) three times with anhydrous acetonitrile, Acetone recrystallization obtains compound (39%) shown in Formulas I f.
1H NMR (400MHz, DMSO) δ 9.57 (d, J=8.0Hz, 2H), 9.38 (d, J=4.0Hz, 2H), 8.76-8.83 (m, 4H), 7.62-7.68 (m, 2H), 7.42-7.53 (m, 3H), 7.14-7.22 (m, 1H), 6.70-6.81 (m, 3H), 6.15- 6.35 (m, 2H), 5.99 (s, 2H), 5,42 (d, J=4.0Hz, 2H), 4.61 (d, J=4.0Hz, 2H), 2.52-2.54 (m, 2H), 1.47-1.58 (m, 2H), 1.17-1.28 (m, 24H), 0.85 (t, J=8.0Hz, 3H)
13C NMR(101MHz,DMSO)δ157.93,149.00,145.65,144.04,142.99,134.16,129.51, 129.25,129.23,128.95,127.17,126.89,124.69,120.90,114.58,111.59,66.46,63.30, 61.46,35.14,31.25,30.84,28.98,28.82,28.66,22.06,13.93.
HRMS(ESI-TOF)m/z:[M-2Br]+Calcd for[C42H56N2O]2+302.2191；Found 302.2187.
Embodiment 7
The measure of compound surface tension force shown in Formulas I a, Ib, Ic, Id, Ie and If：
Concrete operation step：The surface tension of 20mL deionized waters under test condition is measured first, then by four samples The solution that concentration is 0.002mol/L is made into respectively, and initially using 5 μ L as addition unit, each target is progressively added into deionized water The solution prepared of molecule, and measure the surface tension numerical value under corresponding concentration.Repeat the above steps, and suitably expand every The addition volume of secondary target product solution, until the surface tension of solution keeps stable.Measurement result is shown in Fig. 1.According to having surveyed The CMC value and γ of each molecule has been calculated with the data of change in concentration in the surface tension obtainedCMCValue, and with tester pair According to the results are shown in Table 1.
Table 1.
* tester is the cationic surfactant of commercialization：Cetyl trimethylammonium bromide (CTAB)
As shown in Table 1：The CMC value of six samples is far below commercially produced product CTAB, and can be incited somebody to action under at a fairly low concentration Solution surface tension is reduced to 25mN/m or so, and surface-active is quite excellent.

Claims (4)

1. a kind of Cardanol derivative, the Cardanol derivative is compound shown in Formulas I：
In Formulas I, R1For C15Chain alkyl, A be divalence C2~C4Chain alkyl, R2For the C of monovalence or divalence3~C17It is nitrogenous Heterocyclic onium cations base, n are 1 or 2.
2. Cardanol derivative as claimed in claim 1, it is characterised in that wherein R2For one of following groups：
3. Cardanol derivative as claimed in claim 2, it is characterised in that described Cardanol derivative is following compounds One of：
4. application of the Cardanol derivative as cationic surfactant as described in any one in claims 1 to 3.
CN201711110811.7A 2017-11-10 2017-11-10 Cardanol derivative and application thereof Expired - Fee Related CN107892671B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201711110811.7A CN107892671B (en) 2017-11-10 2017-11-10 Cardanol derivative and application thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201711110811.7A CN107892671B (en) 2017-11-10 2017-11-10 Cardanol derivative and application thereof

Publications (2)

Publication Number Publication Date
CN107892671A true CN107892671A (en) 2018-04-10
CN107892671B CN107892671B (en) 2021-03-26

Family

ID=61805122

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201711110811.7A Expired - Fee Related CN107892671B (en) 2017-11-10 2017-11-10 Cardanol derivative and application thereof

Country Status (1)

Country Link
CN (1) CN107892671B (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108658846A (en) * 2018-06-12 2018-10-16 上海邦高化学有限公司 Quaternary amine of the group containing anacardol and application thereof
CN109796396A (en) * 2019-02-18 2019-05-24 山西医科大学 A kind of preparation method of N- methyl -4,4 '-bipyridyl iodide
CN110105284A (en) * 2019-05-30 2019-08-09 上海邦高化学有限公司 Cashew nut phenol quaternary ammonium salt and application thereof
CN110590581A (en) * 2019-09-06 2019-12-20 天津理工大学 Cardanol-based aqueous phase dispersing auxiliary agent for improving carbon nano tube aqueous phase sterilizing capability and synthesis method thereof

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007176751A (en) * 2005-12-28 2007-07-12 Fujifilm Corp Organized layered silicate, its production method, and resin composition
CN102824876A (en) * 2012-09-11 2012-12-19 上海美东生物材料有限公司 Anacardol cationic surface active agent and preparation method thereof
CN103145568A (en) * 2013-03-18 2013-06-12 东北石油大学 Cardanol cationoid quaternary ammonium salt and preparation method thereof
CN103554442A (en) * 2013-11-20 2014-02-05 哈尔滨师范大学 Cardanol derivative curing agent and preparation method thereof
BR102014030002A2 (en) * 2014-11-24 2016-05-31 Fundação Universidade Fed De Mato Grosso Do Sul Ufms efficient purification process of cardanol isolated from cashew nut shell liquid (lcc) and production of derivatives of industrial interest
CN108948410A (en) * 2018-06-25 2018-12-07 青岛海尔股份有限公司 Glycol composition and its polyurethane rigid foam plastic of preparation

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007176751A (en) * 2005-12-28 2007-07-12 Fujifilm Corp Organized layered silicate, its production method, and resin composition
US20090306260A1 (en) * 2005-12-28 2009-12-10 Fujifilm Corporation Organized Layered Silicate And Method For Producing Same, Resin Composition
CN102824876A (en) * 2012-09-11 2012-12-19 上海美东生物材料有限公司 Anacardol cationic surface active agent and preparation method thereof
CN103145568A (en) * 2013-03-18 2013-06-12 东北石油大学 Cardanol cationoid quaternary ammonium salt and preparation method thereof
CN103554442A (en) * 2013-11-20 2014-02-05 哈尔滨师范大学 Cardanol derivative curing agent and preparation method thereof
BR102014030002A2 (en) * 2014-11-24 2016-05-31 Fundação Universidade Fed De Mato Grosso Do Sul Ufms efficient purification process of cardanol isolated from cashew nut shell liquid (lcc) and production of derivatives of industrial interest
CN108948410A (en) * 2018-06-25 2018-12-07 青岛海尔股份有限公司 Glycol composition and its polyurethane rigid foam plastic of preparation

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
GULATI, A等: "Quaternary nitrogen germicides derived from the monophenolic components of cashew nut shell liquid", 《INDIAN JOURNAL OF CHEMISTRY》 *
RENJITH SAS，ET AL.: "High Performing Biobased Ionic Liquid Crystal Electrolytes for Supercapacitors", 《ACS SUSTAINABLE CHEMISTRY & ENGINEERING》 *
丁晨亭等: "腰果酚衍生物的合成", 《黑龙江科技信息》 *
胡仲禹等: "腰果酚衍生物的合成及应用研究进展", 《江西科技师范大学学报》 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108658846A (en) * 2018-06-12 2018-10-16 上海邦高化学有限公司 Quaternary amine of the group containing anacardol and application thereof
CN108658846B (en) * 2018-06-12 2021-03-26 上海邦高化学有限公司 Quaternary ammonium salt containing cardanol group and application thereof
CN109796396A (en) * 2019-02-18 2019-05-24 山西医科大学 A kind of preparation method of N- methyl -4,4 '-bipyridyl iodide
CN110105284A (en) * 2019-05-30 2019-08-09 上海邦高化学有限公司 Cashew nut phenol quaternary ammonium salt and application thereof
CN110105284B (en) * 2019-05-30 2022-07-12 上海邦高化学有限公司 Quaternary ammonium salt of cardanol and application thereof
CN110590581A (en) * 2019-09-06 2019-12-20 天津理工大学 Cardanol-based aqueous phase dispersing auxiliary agent for improving carbon nano tube aqueous phase sterilizing capability and synthesis method thereof

Also Published As

Publication number Publication date
CN107892671B (en) 2021-03-26

Similar Documents

Publication Publication Date Title
CN107892671A (en) Cardanol derivative and application thereof
AU775157B2 (en) Method of inhibiting amyloid protein aggregation and imaging amyloid deposits
CN109529940A (en) Diphenylamines-phosphine-oxazoline ligand, its synthetic method and its metal complex and purposes
Li et al. An insight into the extraction of transition metal ions by picolinamides associated with intramolecular hydrogen bonding and rotational isomerization
CN110483252A (en) A kind of synthetic method of asymmetry triarylmethane derivatives
Desroches et al. Nitration of thiacalix [4] arene using nitrosium nitrate complexes: synthesis and characterization of tetranitro-, tetraamino-, and tetra (4-pyridylimino) tetrahydroxythiacalix [4] arene
Rapi et al. Synthesis and recognition properties of α-D-glucose-based fluorescent crown ethers incorporating an acridine unit
KR20180026754A (en) Substituted benzotriazole phenolate salts and antioxidant compositions formed therefrom
CN105924450B (en) Synthesis method of azafluorene spiro-aromatic hydrocarbon
US9056314B2 (en) Palladium catalyst, method for its preparation and its use
CN110423217A (en) A kind of preparation method of conjugated enynes compound
CN107253921B (en) A kind of acylhydrazone and its preparation method and application containing pyrenyl
CN108911937B (en) Synthesis method of tetraarylethylene compound
CN115850254A (en) Synthetic method of sulfuryl pyraflufen
CN113416162B (en) Double-chiral binaphthyl O-N-N tridentate ligand and preparation method thereof
CN102153483B (en) Axial chirality vicinal diamine compound and preparation method thereof
US4031111A (en) Macrocyclic hetero imine complexing agents
CN111440178B (en) benzothiazole-Schiff base-Tryger's base derivative and preparation method and application thereof
Kurjatschij et al. Synthesis and structures of crystalline solvates formed of pyridinium N-phenoxide (Reichardt's-type) betaine dyes and alcohols
JP5232989B2 (en) Optically active 2,6-bisaminomethylpyridine derivative, production method thereof and use thereof
Mukhopadhyay et al. An ionic liquid [secbmim]+ Br—as a “dual reagent catalyst” for the multicomponent synthesis of (quinolinyl-and isoquinolinyl-amino) alkylnaphthols, their bis-analogs and a facile route to naphthoxazines
CN113416149B (en) Biaryl axial chiral compound synthesized by nitrogen heterocyclic carbene catalysis and preparation method thereof
CN114349732B (en) Lycorine derivative intermediate, application thereof and preparation method of lycorine derivative HYL78
CN110437227A (en) A kind of polysubstituted tetrahydroisoquinoline and preparation method thereof with polycyclic bridge ring skeleton
CN114989048B (en) Cyclobut-1-enamine compound, preparation method thereof and application thereof in anti-II-type dengue virus drugs

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20210326

Termination date: 20211110

CF01 Termination of patent right due to non-payment of annual fee