CN106316970A - Bis-benzotriazole containing organic dyestuff with super thermal stability - Google Patents

Bis-benzotriazole containing organic dyestuff with super thermal stability Download PDF

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Publication number
CN106316970A
CN106316970A CN201610659793.7A CN201610659793A CN106316970A CN 106316970 A CN106316970 A CN 106316970A CN 201610659793 A CN201610659793 A CN 201610659793A CN 106316970 A CN106316970 A CN 106316970A
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China
Prior art keywords
organic dyestuff
benzotriazole
thermal stability
bis
hyperthermostable
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Pending
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CN201610659793.7A
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Chinese (zh)
Inventor
荆川
王震强
高放
李红茹
张胜涛
罗自萍
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Chongqing University
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Chongqing University
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Priority to CN201610659793.7A priority Critical patent/CN106316970A/en
Publication of CN106316970A publication Critical patent/CN106316970A/en
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18—Benzotriazoles
    • C07D249/20—Benzotriazoles with aryl radicals directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B13/00—Oxyketone dyes
    • C09B13/06—Oxyketone dyes of the acetophenone series

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses bis-benzotriazole containing organic dyestuff with super thermal stability. The chemical general formula of the organic dyestuff is shown in the description. The organic dyestuff with super thermal stability comprises the following synthesis steps that 1-[3-(2H-benzotriazole-2-yl)-4-hydroxylphenyl]aceton and a phthalic aldehyde derivative are added into a three-mouth flask according to the ratio of 2:1, ethyl alcohol with the volume 20-30 times that of 1-[3-(2H-benzotriazole-2-yl)-4-hydroxylphenyl]aceton is added to serve as a solvent, magnetic stirring is carried out at the temperature of 80-90 DEG C for 20 hours, suction filtration, ethyl alcohol washing and vacuum drying are carried out after the reaction is over, and the target compound is obtained. The bis-benzotriazole containing organic dyestuff with super thermal stability can exist stably even at the high temperature of 400 DEG C, which proves that the organic dyestuff is a thermal stabilizer with excellent performance.

Description

One class has containing double benzene the triazole organic dyestuff of Hyperthermostable
Technical field
The invention belongs to organic Hyperthermostable organic material field, it is double that particularly one class has containing of Hyperthermostable BTA organic dyestuff and synthesis thereof.
Background technology
Recently, organic small molecule material has a wide range of applications in terms of material science, Chemical Engineering.Due to organic molecule Chemical bond easy fracture, therefore organic material is at 400 DEG C of very difficult stable existences, thus at present heat decomposition temperature 400 DEG C or more than Organic small molecule material actually rare.
Summary of the invention
The invention aims to overcome the deficiency of above-mentioned background technology, and synthesize a class and there is containing of Hyperthermostable Double BTA organic dyestuff.
The present invention relates to has organic high thermal stability compound, and its chemical formula is:
The synthetic method of the above-mentioned containing double benzene with Hyperthermostable triazole organic dyestuff is as follows:
By 1-[3-(2H-benzotriazole-2-base)-4-hydroxy phenyl] ethyl ketone and the phthalaldehyde ratio with mol ratio as 2:1 Example adds in there-necked flask, and addition volume is 1-[3-(2H-benzotriazole-2-base)-4-hydroxy phenyl] ethyl ketone 20～30 times Ethanol is solvent, 80～90 DEG C of magnetic agitation 20 hours, and reaction terminates, sucking filtration, washing with alcohol, and vacuum drying obtains targeted Compound.
The synthetic route of above-claimed cpd is as follows:
Accompanying drawing explanation
Fig. 1. (2E, 2'E)-3,3'-benzene-1,4-diyl two { 1-[3-(2H-benzotriazole-2-the base)-4-in embodiment 1 Hydroxy phenyl] acrylate-2-alkene-1-ketone }1H nmr spectrum (1H-NMR)；
Fig. 2. (2E, 2'E)-3,3'-benzene-1,2-diyl two { 1-[3-(2H-benzotriazole-2-the base)-4-in embodiment 2 Hydroxy phenyl] acrylate-2-alkene-1-ketone }1H nmr spectrum (1H-NMR)；
(2E, 2'E)-3,3'-benzene-1,4-diyl two { 1-[3-(2H-benzotriazole-2-base)-4-in Fig. 3 embodiment 3 Hydroxy phenyl] acrylate-2-alkene-1-ketone thermogravimetric analysis collection of illustrative plates；
Fig. 4. (2E, 2'E)-3,3'-benzene-1,2-diyl two { 1-[3-(2H-benzotriazole-2-the base)-4-in embodiment 4 Hydroxy phenyl] acrylate-2-alkene-1-ketone thermogravimetric analysis collection of illustrative plates；
Detailed description of the invention
The present invention is further illustrated below in conjunction with instance graph and accompanying drawing:
Embodiment 1
(2E, 2'E)-3,3'-benzene-1,4-diyl two { 1-[3-(2H-benzotriazole-2-base)-4-hydroxy phenyl] acrylate-2- Alkene-1-ketone }
By 1-[3-(2H-benzotriazole-2-base)-4-hydroxy phenyl] ethyl ketone (0.20mmol, 0.120g), with terephthaldehyde Aldehyde (0.10mmol, 0.013g) mixes in there-necked flask, and with 15mL ethanol as solvent, 80～90 DEG C of magnetic agitation are after 20 hours Terminate reaction, sucking filtration, washing with alcohol, vacuum drying, obtain target product, productivity 76%, its1H nmr spectrum such as Fig. 1.1H-NMR(CDCl3, 400MHZ) and δ (ppm): 11.469 (s, 2H ,-OH), 8.599-8.596 (t, J=1.2Hz, 2H, Ar-H), 8.307-8.289 (m, 2H, Ar-H), 8.078-8.045 (m, 7H, Ar-H), 7.958 (s, J=12.4Hz, 3H, Ar-H), 7.788-7.762 (d, J=10.4Hz, 2H, Ar-H), 7.551-7.535 (m, 4H ,-CH=CH-), 7.304-7.289 (d, J= 6Hz,2H,Ar-H)。
Embodiment 2
(2E, 2'E)-3,3'-benzene-1,2-diyl two { 1-[3-(2H-benzotriazole-2-base)-4-hydroxy phenyl] acrylate-2- Alkene-1-ketone }
By 1-[3-(2H-benzotriazole-2-base)-4-hydroxy phenyl] ethyl ketone (0.20mmol, 0.120g), with O-phthalic Aldehyde (0.10mmol, 0.013g) mixes in there-necked flask, and with 15mL ethanol as solvent, 80～90 DEG C of magnetic agitation are after 20 hours Terminate reaction, sucking filtration, by washing with alcohol, vacuum drying, obtain target product, productivity 68%, its1H nmr spectrum such as figure 2。1H-NMR(CDCl3,400MHZ)δ(ppm):11.472(s,2H,-OH),8.584(s,2H,Ar-H),8.303-8.288(s,J =6Hz, 2H, Ar-H), 8.078-8.045 (m, 6H, Ar-H), 7.958 (s, 4H, Ar-H), 7.787-7.761 (d, J= 10.4Hz, 2H, Ar-H), 7.550-7.535 (m, 4H ,-CH=CH-), 7.300-7.286 (d, J=5.6Hz, 2H, Ar-H).
Embodiment 3
To sample (2E, 2'E)-3,3'-benzene-1,4-diyl two { 1-[3-(2H-benzotriazole-2-base)-4-hydroxy phenyl] Acrylate-2-alkene-1-ketone } carry out thermogravimetric analysis, parameter is: temperature elevating range 0～600 DEG C, 10 DEG C/min of heating rate.It is completed After, draw thermogravimetric collection of illustrative plates 3.Heat decomposition temperature is 407.35 DEG C, is shown to be the dye molecule that a kind of thermal stability is superior.
Embodiment 4
To sample (2E, 2'E)-3,3'-benzene-1,2-diyl two { 1-[3-(2H-benzotriazole-2-base)-4-hydroxy phenyl] Acrylate-2-alkene-1-ketone } carry out thermogravimetric analysis, parameter is: temperature elevating range 0～600 DEG C, 10 DEG C/min of heating rate.It is completed After, draw thermogravimetric collection of illustrative plates 4.Heat decomposition temperature is 409.43 DEG C, is shown to be the dye molecule that a kind of thermal stability is superior.

Claims (3)

1. a class has containing double benzene the triazole organic dyestuff of Hyperthermostable, and its chemical formula is:
。
A class the most as claimed in claim 1 has the synthetic method of the containing double benzene of Hyperthermostable triazole organic dyestuff such as Under:
By 1-[3-(2H-benzotriazole-2-base)-4-hydroxy phenyl] ethyl ketone and phthalaldehyde derivant with mol ratio as 2:1 Ratio adds in there-necked flask, and addition volume is 1-[3-(2H-benzotriazole-2-base)-4-hydroxy phenyl] ethyl ketone 20～30 times Ethanol be solvent, 80～90 DEG C of magnetic agitation 20 hours, reaction terminates, sucking filtration, washing with alcohol, vacuum drying, obtains target Compound.
A class the most as claimed in claim 1 has containing double benzene the triazole organic dyestuff of Hyperthermostable, and its purposes is: should Heat stable material can under the hot environment of 400 DEG C stable existence, can be as a kind of superior heat stabilizer.
CN201610659793.7A 2016-08-11 2016-08-11 Bis-benzotriazole containing organic dyestuff with super thermal stability Pending CN106316970A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107353668A (en) * 2017-07-05 2017-11-17 浙江山峪科技股份有限公司 A kind of monoazo thiazole heterocycle type disperse dye and preparation method thereof

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6419064A (en) * 1987-07-15 1989-01-23 Hitachi Ltd Unsaturated bisimide compound
JPS6456643A (en) * 1987-08-28 1989-03-03 Hitachi Ltd Addition reaction type compound, production and related substance thereof
JPS6461484A (en) * 1987-08-31 1989-03-08 Hitachi Ltd Addition type imide based compound, production and composition thereof
JPS6463560A (en) * 1987-09-03 1989-03-09 Hitachi Ltd Cinnamanilide, its preparation and use
JPH0196173A (en) * 1987-10-07 1989-04-14 Hitachi Ltd Bipyridine-based compound, production and composition thereof
US4853471A (en) * 1981-01-23 1989-08-01 Ciba-Geigy Corporation 2-(2-Hydroxyphenyl)-benztriazoles, their use as UV-absorbers and their preparation
CN1183442A (en) * 1996-11-07 1998-06-03 希巴特殊化学控股公司 Benzotriazole UV absorbers having enhanced durability
CN101537746A (en) * 2008-03-18 2009-09-23 株式会社理光 Heat resistance improver and reversible thermosensitive recording medium

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4853471A (en) * 1981-01-23 1989-08-01 Ciba-Geigy Corporation 2-(2-Hydroxyphenyl)-benztriazoles, their use as UV-absorbers and their preparation
JPS6419064A (en) * 1987-07-15 1989-01-23 Hitachi Ltd Unsaturated bisimide compound
JPS6456643A (en) * 1987-08-28 1989-03-03 Hitachi Ltd Addition reaction type compound, production and related substance thereof
JPS6461484A (en) * 1987-08-31 1989-03-08 Hitachi Ltd Addition type imide based compound, production and composition thereof
JPS6463560A (en) * 1987-09-03 1989-03-09 Hitachi Ltd Cinnamanilide, its preparation and use
JPH0196173A (en) * 1987-10-07 1989-04-14 Hitachi Ltd Bipyridine-based compound, production and composition thereof
CN1183442A (en) * 1996-11-07 1998-06-03 希巴特殊化学控股公司 Benzotriazole UV absorbers having enhanced durability
CN101537746A (en) * 2008-03-18 2009-09-23 株式会社理光 Heat resistance improver and reversible thermosensitive recording medium

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107353668A (en) * 2017-07-05 2017-11-17 浙江山峪科技股份有限公司 A kind of monoazo thiazole heterocycle type disperse dye and preparation method thereof

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