CN105348849B - A kind of azoic dye and dye liquid crystal compound - Google Patents
A kind of azoic dye and dye liquid crystal compound Download PDFInfo
- Publication number
- CN105348849B CN105348849B CN201510653872.2A CN201510653872A CN105348849B CN 105348849 B CN105348849 B CN 105348849B CN 201510653872 A CN201510653872 A CN 201510653872A CN 105348849 B CN105348849 B CN 105348849B
- Authority
- CN
- China
- Prior art keywords
- formula
- liquid crystal
- dye
- compound
- expression
- 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.)
- Active
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 57
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 54
- 239000000203 mixture Substances 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 9
- 239000000975 dye Substances 0.000 description 33
- 238000003756 stirring Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- MEYRNRQMHWCAKV-UHFFFAOYSA-N heptane;naphthalene Chemical class CCCCCCC.C1=CC=CC2=CC=CC=C21 MEYRNRQMHWCAKV-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000013019 agitation Methods 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical class [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- -1 azo compound Chemical class 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- TZTDJBMGPQLSLI-UHFFFAOYSA-N (4-nitrophenyl)-phenyldiazene Chemical compound C1=CC([N+](=O)[O-])=CC=C1N=NC1=CC=CC=C1 TZTDJBMGPQLSLI-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- PEJOQASNBCUDMB-UHFFFAOYSA-N 2-aminonaphthalen-1-ol;hydrochloride Chemical class [Cl-].C1=CC=CC2=C(O)C([NH3+])=CC=C21 PEJOQASNBCUDMB-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000005267 amalgamation Methods 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
Abstract
The present invention relates to a kind of azoic dye and dye liquid crystal compound, azoic dye has following structural formula：The azoic dye that the present invention is provided shows that character is beautiful, and good with liquid crystal mixed stability, in liquid crystal, dissolubility is good, can be widely used in mixed liquid crystal material.
Description
Technical field
The present invention relates to a kind of azoic dye and dye liquid crystal compound, belong to technical field of organic synthesis.
Background technology
The species of dyestuff is various, good stability, and the dyestuff that can be used in liquid crystal material needs to carry out from numerous dyestuffs
Screening sets.Dye liquid crystal is master-guest's form, nematic liquid crystal as main body display material, dyestuff as additive, with liquid
Brilliant material is miscible, and in the case of energization, liquid crystal molecular movement can drive the molecule of dyestuff to move together, reach display effect,
Therefore it is required that liquid crystal dyestuff can have good intermiscibility with liquid crystal, molecular structure is similar to liquid crystal molecule structure, and has very well
Chemistry, light, heat endurance.Heterogeneous colours liquid crystal is high with its contrast, and it is clear to show, the characteristic such as display content is attractive in appearance, and one
High-end product --- the favor of-automobile instrument is directly subject to.In liquid crystal heterogeneous colours, azo compound is with its molecular structure
Into bar-shaped, good with liquid crystal material amalgamation, good stability is widely used on dye liquid crystal.
Liquid crystal dyestuff has azo, Anthraquinones, azines and oxa anthracenes etc., it is desirable to can have very well with liquid crystal composition
Intermiscibility, be added in mixed liquid crystal, do not reduce the stability of mixed liquid crystal material.Under liquid crystal material power-up field action,
Twisting can be synchronized with liquid crystal molecule, be equally directed to swear with liquid crystal molecule, when showing, there can be very bright face
Color, colourless under closed mode.
Domestic and foreign literature also has the azo dyes report of dependency structure：
These compounds all have the performance of dyestuff, but when used in liquid crystal, have certain defect, some display words
Symbol is not beautiful enough, and having bad with mixed liquid crystal dissolubility, the stability to liquid crystal is poor, the invention provides a kind of azo
Compound dyestuff, good with mixed liquid crystal intermiscibility, stability is high, can be widely used on mixed liquid crystal material.
Content of the invention
The deficiency that the present invention is present for heterogeneous colours compound in available liquid crystal, there is provided a kind of azoic dye and dye
Feed liquid crystal composite.
The technical scheme that the present invention solves above-mentioned technical problem is as follows：
A kind of azoic dye, it is characterised in that its chemical structural formula is as follows：
N is 0,1 or 2；D is-NH2、-NO2、-OH、-F、-Cl、-H；Alkyl or alkoxyl of the E for C1-C12.
Further, its chemical structural formula is as follows：
The azoic dye that the present invention is provided, its advantage are as follows：The azoic dye that the present invention is provided shows character
Beautiful, good with liquid crystal mixed stability, in liquid crystal, dissolubility is good, can be widely used in mixed liquid crystal material.
The present invention is also claimed a kind of dye liquid crystal compound, including below formula compound：
In formula (I)～(V), the alkyl of the expression C1-C12 of R independences, alkoxyl or thiazolinyl, the expression 1 or 2 of m independences,
The expression 0,1 or the expression of 2, A independence of g independencesOrThe table of X, Y, Z, W independence
Show-F ,-Cl or-H, the alkyl or alkoxyl of the independent expression C1-C12 of R ', the expression-COO- or singly-bound of L independences, formula (G)
In, n is 0,1 or 2；Expression-the NH of D independences2、-NO2、-OH、-F、-Cl、-H；The alkyl or alcoxyl of the expression C1-C12 of E independences
Base；
In above-mentioned composition, the ratio of each component is as follows：By weight, the chemical combination that there is formula (I) one or more
Thing：0～40%；The compound that there is formula (II) one or more：5～80%；The change that there is formula (III) one or more
Compound：3～50%；The compound that there is formula (IV) one or more：0～50%；There is formula (V) one or more
Compound：0～30%；The dye composition that there is formula (G) one or more：0.3～15%.
Further, the compound with formula (I) is：
Further, the compound with formula (II) is：
Further, the compound with formula (III) is：
Further, the compound with formula (IV) is：
Further, the compound with formula (V) is：
Further, the compound with formula (G) is：
Further, a kind of dye liquid crystal compound, it is characterised in that by weight, each component in the composition
Ratio is as follows：
The compound that there is formula (I) one or more：3～25%；
The compound that there is formula (II) one or more：10～50%；
The compound that there is formula (III) one or more：12～40%；
The compound that there is formula (IV) one or more：5～40%；
The compound that there is formula (V) one or more：3～20%；
The dye composition that there is formula (G) one or more：0.5～8%.
The invention has the beneficial effects as follows：Liquid-crystal composition low temperature performance well, temperature range width, refractive index are big, good stability,
Can be used for the display of onboard instruments.
The synthetic route of the azoic dye that the present invention is provided is as follows：
The dye is described by taking the synthesis of 1- (4 '-(4 "-amino-phenylazo)-phenylazo) -4- epoxide in heptan naphthalenes as an example below
The synthetic method of material：
1) synthesis to two ammonium of benzene
15.0 grams (0.109mol) are added in the 250ml there-necked flasks for being furnished with mechanical agitation, thermometer, condenser to nitre
Base aniline, 100.0ml DMF, 0.2 gram of Pd/C (5wt%) heat to 60--65 DEG C while stirring, are passed through thereto high-purity
Hydrogen, insulation reaction 1.5 hours while stirring, TLC detection raw materials are not detected, and are filtered, and filtrate concentrates, and concentrate is cooled to 0 DEG C
Left and right, adds 0 DEG C or so of isopropanol, filters, and dries, obtains 11.22 grams of bronzing p-phenylenediamine product (0.104mol), yield
96.0%.
2) synthesis of 4- (4 '-nitro-azobenzene)-aniline
To with mechanical agitation, add step 1 in the 500ml there-necked flasks of thermometer) in obtain to two ammonium product of benzene
It is 5mol/L watery hydrochloric acid with 250.0ml concentration, is cooled to -5 DEG C of temperature while stirring -- 0 DEG C, slowly dripped with constant pressure funnel
Solubilization maintains the temperature at -5 DEG C in 7.11 grams of (0.103mol) sodium nitrite in aqueous solution of 40.0ml water, dropwise addition process -- and 0 DEG C, drop
Add after finishing in 0--5 DEG C of insulated and stirred 60 minutes, be added dropwise to the urea that 10 grams (0.166mol) are dissolved in 40.0ml water, stirring 0.5
Hour, the dilute hydrochloric acid solution that 14.35 grams of (0.104mol) paranitroanilinum are dissolved in 50.0ml 5mol/L is added dropwise, after completion of dropping
Continue reaction 0.5 hour, low temperature with unsaturated carbonate potassium solution neutralize, filter, obtain sediment, be vacuum dried, obtain product 4- (4 '-
Nitro-azobenzene) 24.44 grams of-aniline (0.101mol), yield 97.1%.
3) synthesis of 4- amino -1- naphthalene heptyl ethers
30.00 grams of (0.153mol) 4- are added in mechanical agitation, thermometer, the 500ml there-necked flasks of condenser
Amino -1- naphthalenol hydrochlorides, add 200.0ml DMF, add 30.00 grams of (0.217mol) potassium carbonate, add 1.00 grams of 18-
Crown- 6, is heated while stirring, treats that temperature rises to 70 DEG C -- and 75 DEG C, it is added dropwise with constant pressure funnel and is dissolved in 50.0ml DMF's
35.00 grams of (0.154mol) 1- iodine heptane, after completion of dropping, continue reaction 4.5 hours, and reaction terminates, and filters, and concentration is dried,
Obtain 38.43 grams of product 4- amino -1- naphthalene heptyl ethers (1.3.3) (0.149mol), yield 97.3%.
4) synthesis of 1- (4 '-(4 "-nitro-phenylazo)-phenylazo) -4- epoxide in heptan naphthalenes
4- (4 '-nitros-idol are added in the 1000ml there-necked flasks for being furnished with mechanical agitation, thermometer, constant pressure funnel
Pyridine)-aniline and 500.0ml 5mol/L watery hydrochloric acid, be cooled to 0--5 DEG C while stirring, be added dropwise with constant pressure funnel
9.00 grams of natrium nitrosums for being dissolved in 60.0ml water, are added dropwise 0--5 DEG C of process control temp, after completion of dropping, continue stirring 0.5 little
When, during 10.00 grams of (0.166) urea for being dissolved in 40.0ml water are also added dropwise into mixed reaction solution, continue stirring 0.5 hour, drop
Plus 26.08 grams (0.101mol) is dissolved in the product (1.3.3) of 200.0ml acetic acid, after completion of dropping, temperature is controlled at 0--5 DEG C,
Reaction 3.5 hours.After completion of the reaction, the wet chemical adjustment PH with saturation is filtered, sediment isopropyl to alkalescent
Alcohol：Water=1:2 mixed solvent recrystallization, be vacuum dried product 1- (4 '-(4 "-nitro-phenylazo)-phenylazo)-
43.10 grams of naphthalene of 4- epoxides in heptan (0.087mol), yield 86.1%.
5) synthesis of 1- (4 '-(4 "-amino-phenylazo)-phenylazo) -4- epoxide in heptan naphthalenes
To in the 1L there-necked flasks for being furnished with mechanical agitation, thermometer, condenser add step 4) in gained product, add
300.0ml DMF, heat while stirring, when temperature rises to 55 DEG C -- 0.45 gram 5% of Pd/C when 60 DEG C, is added, is imported high-purity
Hydrogen, reacts 4.5 hours, and TLC is tracked, and filters catalyst after raw material reaction is finished while hot, and filtrate is transferred to the dense sulphur of 130.0ml
In the mixture of acid/ice, it is cooled to below room temperature, filters, solids isopropanol：Water=5:8 ratio recrystallization, obtains product
1- (4 '-(4 "-amino-phenylazo)-phenylazo) 23.57 grams of naphthalene of -4- epoxides in heptan (0.0506mol), yield 58.2%.
Description of the drawings
Fig. 1 is the UV absorption of 1- (4 '-(4 "-amino-phenylazo)-phenylazo) -4- epoxide in the heptan naphthalenes of the present invention
(wavelength of maximum absorption band is 433nm to spectrogram, and the absorbance of maximum absorption band is for 0.91).
Fig. 2 is that the IR spectrograms of 1- (4 '-(4 "-amino-phenylazo)-phenylazo) -4- epoxide in the heptan naphthalenes of the present invention (go out
Peak position is set to 3030～3000cm-1,2810cm-1, 1630～1600cm-1, 1590～1575cm-1, 1480～1470cm-1,
1470～1430cm-1,1300cm-1,1240cm-1,1100cm-1,846cm-1,740cm-1,610cm1, 500～400cm-1).
Fig. 3 is 1- (4 '-(4 "-amino-phenylazo)-phenylazo) -4- epoxide in the heptan naphthalenes of the present invention13C-NMR is composed
Figure；Signal data is as follows：
δ 125.8,128.6,142.5,144.1,148.9,154.7,157.5 (s)
δ103.9,115.4,119.9,121.9,123,123.5,125.0,126.2,127.3(d)
δ23.1,26.6,30.2,30.6,32.5,72.7(t)
δ14.0(q)
Specific embodiment
The principle and feature of the present invention are described below in conjunction with example, example is served only for explaining the present invention, and
Non- for limiting the scope of the present invention.
The code description of compound used therefor in liquid-crystal composition：
E- ——COO—— T- ——C≡C——
n- CnH2n+1—— On- ——O
V- CH=CH2
nV- CnH2nCH=CH2N- ——CN
nVm- ——CnH2nCH=CHCmH2m+1F- ——F
K- NH2——
The use of compound code is described with instantiation below：
Embodiment 1:
A kind of dye liquid crystal compound, by weight, its formula is as follows：
| Sequence number | Compound code | Ratio |
| 1 | 2VPEG-N | 6 |
| 2 | 2CPEG-N | 3 |
| 3 | 4CPEG-N | 5 |
| 4 | 5PEG-N | 8 |
| 5 | 3CPEG-N | 5 |
| 6 | 5CPEG-N | 5 |
| 7 | 2PEG-N | 3 |
| 8 | 3PEG-N | 5 |
| 9 | 4PEG-N | 10 |
| 10 | 3UTPP2 | 5 |
| 11 | VCP-N | 10 |
| 12 | 3PP-N | 3 |
| 13 | 5PP-N | 5 |
| 14 | VCC3 | 12 |
| 15 | 3CPPC5 | 5 |
| 16 | 3CPPC4 | 5 |
| 17 | 3CCEPC5 | 5 |
| ⅰ | KAzAzNpO3 | 1 |
| ⅱ | KAzAzNhO3 | 0.5 |
| ⅲ | KAzAzNnO2 | 0.5 |
The test physical parameter of above-mentioned composition is as follows：
| Test event | Test data |
| Tni(℃) | 98 |
| △n(589nm,20℃) | 0.205 |
| ne(589nm,20℃) | 1.712 |
| no(589nm,20℃) | 1.507 |
| △ε(1KHz,25℃) | 31.2 |
| ε⊥(1KHz,25℃) | 7.8 |
| Vth(25℃,1/1D,1/1B) | 1.14 |
| Vsat(25℃,1/1D,1/1B) | 1.73 |
| ST | 1.52 |
| η(25℃) | 56 |
| - 40 DEG C of low-temperature storage | pass |
Embodiment 2：
A kind of dye liquid crystal compound, by weight, its formula is as follows：
The test physical parameter of above-mentioned composition is as follows：
| Test event | Test data |
| Tni(℃) | 101 |
| △n(589nm,20℃) | 0.260 |
| ne(589nm,20℃) | 1.774 |
| no(589nm,20℃) | 1.514 |
| △ε(1KHz,25℃) | 32.8 |
| ε⊥(1KHz,25℃) | 8.3 |
| Vth(25℃,1/1D,1/1B) | 1.11 |
| Vsat(25℃,1/1D,1/1B) | 1.61 |
| ST | 1.45 |
| η(25℃) | 52 |
| - 40 DEG C of low-temperature storage | pass |
Embodiment 3：
A kind of dye liquid crystal compound, by weight, its formula is as follows：
| Sequence number | Compound code | Ratio |
| 1 | VCPU-N | 5 |
| 2 | 3CPU-N | 5 |
| 3 | 3PEG-N | 3 |
| 4 | 5PEG-N | 5 |
| 5 | 2VPEG-N | 5 |
| 6 | 2VPEU-N | 3 |
| 7 | 3PTP02 | 3 |
| 8 | 2UTPP3 | 5 |
| 9 | 3UTPP2 | 2 |
| 10 | 4UTPP3 | 2 |
| 11 | 3UTPP4 | 3 |
| 12 | VCP-N | 12 |
| 13 | 1VCP-N | 8 |
| 14 | 3CP-N | 6 |
| 15 | 5PP-N | 14 |
| ⅰ | KAzAzNpO7 | 5 |
| ⅱ | KAzAzNa3 | 8 |
| ⅲ | KAzAzNhO3 | 2 |
The test physical parameter of above-mentioned composition is as follows：
| Test event | Test data |
| Tni(℃) | 105 |
| △n(589nm,20℃) | 0.205 |
| ne(589nm,20℃) | 1.719 |
| no(589nm,20℃) | 1.514 |
| △ε(1KHz,25℃) | 21.2 |
| ε⊥(1KHz,25℃) | 5.8 |
| Vth(25℃,1/1D,1/1B) | 1.31 |
| Vsat(25℃,1/1D,1/1B) | 1.83 |
| ST | 1.40 |
| η(25℃) | 43 |
| - 40 DEG C of low-temperature storage | pass |
Embodiment 4:
A kind of dye liquid crystal compound, by weight, its formula is as follows：
The test physical parameter of above-mentioned composition is as follows：
| Test event | Test data |
| Tni(℃) | 108 |
| △n(589nm,20℃) | 0.258 |
| ne(589nm,20℃) | 1.768 |
| no(589nm,20℃) | 1.510 |
| △ε(1KHz,25℃) | 23.3 |
| ε⊥(1KHz,25℃) | 5.9 |
| Vth(25℃,1/1D,1/1B) | 1.32 |
| Vsat(25℃,1/1D,1/1B) | 1.81 |
| ST | 1.37 |
| η(25℃) | 58 |
| - 40 DEG C of low-temperature storage | pass |
Embodiment 5：
A kind of dye liquid crystal compound, by weight, its formula is as follows：
| Sequence number | Compound code | Ratio |
| 1 | 2UTPP3 | 10 |
| 2 | 4CPTP3 | 4 |
| 3 | 3CPTP02 | 4 |
| 4 | 3UTPP4 | 9 |
| 5 | 3UTPP2 | 10 |
| 6 | VCP-N | 3 |
| 7 | VCC3 | 20 |
| 8 | 3CC4 | 5 |
| 9 | 5CC3 | 5 |
| 10 | VCC5 | 15 |
| 11 | VCC4 | 5 |
| 12 | 3CCEPC4 | 3 |
| ⅰ | KAzAzNp3 | 1 |
| ⅱ | KAzAzNpO5 | 2 |
| ⅲ | KAzAzNpO7 | 2 |
The test physical parameter of above-mentioned composition is as follows：
| Test event | Test data |
| Tni(℃) | 103 |
| △n(589nm,20℃) | 0.259 |
| ne(589nm,20℃) | 1.773 |
| no(589nm,20℃) | 1.514 |
| △ε(1KHz,25℃) | 6.3 |
| ε⊥(1KHz,25℃) | 3.7 |
| Vth(25℃,1/1D,1/1B) | 2.45 |
| Vsat(25℃,1/1D,1/1B) | 3.36 |
| ST | 1.37 |
| η(25℃) | 25 |
| - 40 DEG C of low-temperature storage | pass |
Embodiment 6：
A kind of dye liquid crystal compound, by weight, its formula is as follows：
The test physical parameter of above-mentioned composition is as follows：
Embodiment 7：
A kind of dye liquid crystal compound, by weight, its formula is as follows：
The test physical parameter of above-mentioned composition is as follows：
| Test event | Test data |
| Tni(℃) | 108 |
| △n(589nm,20℃) | 0.205 |
| ne(589nm,20℃) | 1.727 |
| no(589nm,20℃) | 1.522 |
| △ε(1KHz,25℃) | 3.3 |
| ε⊥(1KHz,25℃) | 3.4 |
| Vth(25℃,1/1D,1/1B) | 3.45 |
| Vsat(25℃,1/1D,1/1B) | 4.86 |
| ST | 1.41 |
| η(25℃) | 22.1 |
| - 40 DEG C of low-temperature storage | pass |
Embodiment 8：
A kind of dye liquid crystal compound, by weight, its formula is as follows：
| Sequence number | Compound code | Ratio |
| 1 | 2VPEU-N | 3 |
| 2 | 5PTP03 | 5 |
| 3 | 3PTP1 | 3 |
| 4 | 3PTP2 | 3 |
| 5 | 4PTP03 | 5 |
| 6 | 3PTP4 | 3 |
| 7 | 4PTP3 | 3 |
| 8 | 3CPTP02 | 3 |
| 9 | 2UTPP3 | 12 |
| 10 | 3UTPP2 | 12 |
| 11 | 3UTPP4 | 15 |
| 12 | 4UTPP3 | 16 |
| 13 | VCP-N | 5 |
| 14 | VCC3 | 7 |
| 15 | VCC5 | 5 |
| ⅰ | KAzAzNh3 | 0.5 |
| ⅱ | KAzAzNpO7 | 0.5 |
| ⅲ | KAzAzNaO5 | 0.2 |
The test physical parameter of above-mentioned composition is as follows：
| Test event | Test data |
| Tni(℃) | 105 |
| △n(589nm,20℃) | 0.260 |
| ne(589nm,20℃) | 1.773 |
| no(589nm,20℃) | 1.513 |
| △ε(1KHz,25℃) | 3.2 |
| ε⊥(1KHz,25℃) | 3.4 |
| Vth(25℃,1/1D,1/1B) | 3.35 |
| Vsat(25℃,1/1D,1/1B) | 4.75 |
| ST | 1.42 |
| η(25℃) | 26.3 |
| - 40 DEG C of low-temperature storage | pass |
The foregoing is only presently preferred embodiments of the present invention, not in order to limit the present invention, all spirit in the present invention and
Within principle, any modification, equivalent substitution and improvements that is made etc. are should be included within the protection domain of invention.
Claims (10)
1. a kind of azoic dye, it is characterised in that its chemical structural formula is as follows：
The expression 0,1 or 2 of n independences；Expression-the NH of D independences2、-NO2、-OH、-F、-Cl、-H；The alkane of the expression C1-C12 of E independences
Base or alkoxyl.
2. a kind of azoic dye according to claim 1, it is characterised in that its chemical structural formula is:
3. a kind of dye liquid crystal compound, it is characterised in that including the compound of below formula：
In formula (I)～(V), the alkyl of the expression C1-C12 of R independences, alkoxyl or thiazolinyl, the expression 1 or 2 of m independences, g are only
Vertical expression 0,1 or the expression of 2, A independence Expression-the F of X, Y, Z, W independence ,-
Cl or-H, R ' independent expression C1-C12 alkyl or alkoxyl, the expression-COO- or singly-bound of L independences, in formula (G), n is only
Vertical expression 0,1 or 2；Expression-the NH of D independences2、-NO2、-OH、-F、-Cl、-H；The alkyl or alkane of the expression C1-C12 of E independences
Epoxide；
In above-mentioned composition, the ratio of each component is as follows：By weight, the compound that there is formula (I) one or more：0～
40%；The compound that there is formula (II) one or more：5～80%；The compound that there is formula (III) one or more：3
～50%；The compound that there is formula (IV) one or more：0～50%；The compound that there is formula (V) one or more：
0～30%；The dye composition that there is formula (G) one or more：0.3～15%.
4. a kind of dye liquid crystal compound according to claim 3, it is characterised in that the chemical combination with formula (I)
Thing is：
5. a kind of dye liquid crystal compound according to claim 3, it is characterised in that the chemical combination with formula (II)
Thing is：
6. a kind of dye liquid crystal compound according to claim 3, it is characterised in that the chemical combination with formula (III)
Thing is：
7. a kind of dye liquid crystal compound according to claim 3, it is characterised in that the chemical combination with formula (IV)
Thing is：
8. a kind of dye liquid crystal compound according to claim 3, it is characterised in that the chemical combination with formula (V)
Thing is：
9. a kind of dye liquid crystal compound according to claim 3, it is characterised in that the chemical combination with formula (G)
Thing is：
10. a kind of dye liquid crystal compound according to claim 3, it is characterised in that by weight, the composition
The ratio of middle each component is as follows：
The compound that there is formula (I) one or more：3～25%；
The compound that there is formula (II) one or more：10～50%；
The compound that there is formula (III) one or more：12～40%；
The compound that there is formula (IV) one or more：5～40%；
The compound that there is formula (V) one or more：3～20%；
The azoic dye that there is formula (G) one or more：0.5～8%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510653872.2A CN105348849B (en) | 2015-10-10 | 2015-10-10 | A kind of azoic dye and dye liquid crystal compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510653872.2A CN105348849B (en) | 2015-10-10 | 2015-10-10 | A kind of azoic dye and dye liquid crystal compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105348849A CN105348849A (en) | 2016-02-24 |
| CN105348849B true CN105348849B (en) | 2017-03-15 |
Family
ID=55324921
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510653872.2A Active CN105348849B (en) | 2015-10-10 | 2015-10-10 | A kind of azoic dye and dye liquid crystal compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105348849B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3529334B1 (en) * | 2016-10-19 | 2020-10-07 | Merck Patent GmbH | Liquid-crystalline medium |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH594897A5 (en) * | 1976-06-23 | 1978-01-31 | Bbc Brown Boveri & Cie | |
| DE3529988A1 (en) * | 1985-08-22 | 1987-02-26 | Basf Ag | TRISAZO DYES AND THEIR USE IN LIQUID CRYSTAL MATERIALS |
| JPH0517776A (en) * | 1991-06-18 | 1993-01-26 | Mitsubishi Kasei Corp | Light modulating material and light modulating element containing the same material |
| JP5029032B2 (en) * | 2007-01-23 | 2012-09-19 | 三菱化学株式会社 | Dichroic dye composition, liquid crystal composition containing the same, and liquid crystal element |
| CN101698802B (en) * | 2009-10-09 | 2013-03-20 | 江苏和成显示科技股份有限公司 | Liquid crystal mixture with low negative dielectric |
| CN103347958B (en) * | 2011-02-07 | 2014-11-12 | 日本化药株式会社 | Azo compound, salt thereof, and dye-based polarizing film and polarizing plate containing same |
| CN103305022A (en) * | 2012-03-16 | 2013-09-18 | 上海汇友精密化学品有限公司 | Azo type direct dye and preparation method thereof |
-
2015
- 2015-10-10 CN CN201510653872.2A patent/CN105348849B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN105348849A (en) | 2016-02-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Saeed et al. | Synthesis and characterization of high wash fastness novel azo reactive dyes incorporating aromatic bridged diamines | |
| FR2564476A1 (en) | NOVEL AZOIC COMPOUNDS, THEIR USE AND THEIR PREPARATION AS COLORANTS | |
| CN105348849B (en) | A kind of azoic dye and dye liquid crystal compound | |
| US3947435A (en) | Disazo acid compounds containing one sulphonic acid group and one phosphonic or methyl-phosphinic acid group | |
| Gong et al. | Trisazo direct black dyes based on nonmutagenic 3, 3′-disubstituted benzidines | |
| KR101850427B1 (en) | Reactive dye composition | |
| Patel et al. | Synthesis, characterization and application of novel bisazo reactive dyes on various fibers | |
| US9512315B2 (en) | Quenching dye for labeling biomolecules and method for preparing the same | |
| Deligeorgiev et al. | Preparation of cationic azo dyes derived from 2-amino-6-(2-chloroethoxy) benzothiazole and 2-amino-4-(2-hydroxyethoxy) benzothiazole | |
| Awale et al. | Synthesis, Characterization and Antimicrobial activity of 2-Amino-1, 3-benzothiazole, Schiff bases and Azo dyes of 2-Amino-1, 3-benzothiazole | |
| US5997587A (en) | Azo dye mixtures, azo dyes, processes for their preparation, and their use | |
| Gamit et al. | Synthesis, characterization and application of some new reactive dyes based on 5, 51-Methylenebis (2-Aminobenzensulfonic acid) | |
| CN105713015B (en) | A kind of imidazoheterocycles azo derivative and its preparation method and application | |
| TWI300792B (en) | Basic mono-and bisazo compounds | |
| KR101621930B1 (en) | Quencher dye for laveling biomolecule and preparation method thereof | |
| Rădulescu et al. | Synthesis and characterization of new cationic dyes for synthetic fibres | |
| US2390152A (en) | Substantive azo dyestuffs | |
| Patel et al. | Studies on Synthesis and Dyeing Preformance of Acid Dyes Based on 4, 7‐Dihydroxy‐1, 10‐Phenanthroline‐2, 9‐Dione | |
| Wadia et al. | Synthesis and Application of Acid Dyes Based on 3‐(4‐Aminophenyl)‐5‐benzylidene‐2‐substituted phenyl‐3, 5‐dihydroimidazol‐4‐one | |
| CN116082854B (en) | Off-site substituted pentamethine cyanine dye and synthetic method and application thereof | |
| RU2540865C1 (en) | Cyclo-bis[(1z)-1-imino-2-methyl-1h-inden-3-yl-1,2,4-thiadiazole-3,5-diamine], possessing property of acid dye for silk, wool and polyamide 6 | |
| US658055A (en) | Brown cotton dye and process of making same. | |
| US2203818A (en) | Azo dyestuffs | |
| JPS5828298B2 (en) | Production method of high purity trisazo direct dye | |
| US650292A (en) | Brown sulfur dye. |
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 | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Azo type dye and dye liquid crystal composition Effective date of registration: 20170928 Granted publication date: 20170315 Pledgee: Yantai re Company limited by guarantee Pledgor: YANTAI XIANHUA CHEM-TECH Co.,Ltd. Registration number: 2017370000151 |
|
| PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
| PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20201030 Granted publication date: 20170315 Pledgee: Yantai re Company limited by guarantee Pledgor: YANTAI XIANHUA CHEM-TECH Co.,Ltd. Registration number: 2017370000151 |
|
| EE01 | Entry into force of recordation of patent licensing contract | ||
| EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20160224 Assignee: Yantai Yida Financial Leasing Co.,Ltd. Assignor: YANTAI XIANHUA CHEM-TECH Co.,Ltd. Contract record no.: X2020980008900 Denomination of invention: Azo dye and dye liquid crystal composition Granted publication date: 20170315 License type: Exclusive License Record date: 20201208 |
|
| PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Azo dye and dye liquid crystal composition Effective date of registration: 20201218 Granted publication date: 20170315 Pledgee: Yantai Yida Financial Leasing Co.,Ltd. Pledgor: YANTAI XIANHUA CHEM-TECH Co.,Ltd. Registration number: Y2020980009565 |
|
| CP03 | Change of name, title or address | ||
| CP03 | Change of name, title or address |
Address after: 264006 No. 6, Yongjiang third branch road, F-12 community, Yantai Development Zone, Yantai area, China (Shandong) pilot Free Trade Zone, Yantai City, Shandong Province Patentee after: Yantai Xianhua Technology Group Co.,Ltd. Address before: 264006 No. 6, Yongjiang Sanzhi Road, F-12 District, Yantai Development Zone, Shandong Province Patentee before: YANTAI XIANHUA CHEM-TECH Co.,Ltd. |
|
| EC01 | Cancellation of recordation of patent licensing contract | ||
| EC01 | Cancellation of recordation of patent licensing contract |
Assignee: Yantai Yida Financial Leasing Co.,Ltd. Assignor: YANTAI XIANHUA CHEM-TECH Co.,Ltd. Contract record no.: X2020980008900 Date of cancellation: 20240304 |
|
| PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
| PC01 | Cancellation of the registration of the contract for pledge of patent right |
Granted publication date: 20170315 Pledgee: Yantai Yida Financial Leasing Co.,Ltd. Pledgor: YANTAI XIANHUA CHEM-TECH Co.,Ltd. Registration number: Y2020980009565 |