CN106632977A - Isocyanate curing agent with fluorescence characteristic and preparation method thereof - Google Patents
Isocyanate curing agent with fluorescence characteristic and preparation method thereof Download PDFInfo
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- CN106632977A CN106632977A CN201611146614.6A CN201611146614A CN106632977A CN 106632977 A CN106632977 A CN 106632977A CN 201611146614 A CN201611146614 A CN 201611146614A CN 106632977 A CN106632977 A CN 106632977A
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- Prior art keywords
- curing agent
- tetraphenylethylene
- isocyanate
- dihydroxy
- solvent
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- 239000012948 isocyanate Substances 0.000 title claims abstract description 40
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 40
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- JLZUZNKTTIRERF-UHFFFAOYSA-N tetraphenylethylene Chemical group C1=CC=CC=C1C(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)C1=CC=CC=C1 JLZUZNKTTIRERF-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000002904 solvent Substances 0.000 claims abstract description 20
- 239000002994 raw material Substances 0.000 claims abstract description 7
- 238000003756 stirring Methods 0.000 claims abstract description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- -1 Polymethylene Polymers 0.000 claims description 12
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 238000010792 warming Methods 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 229920006389 polyphenyl polymer Polymers 0.000 claims 1
- 239000003973 paint Substances 0.000 abstract description 13
- 230000002776 aggregation Effects 0.000 abstract description 5
- 238000004220 aggregation Methods 0.000 abstract description 5
- 230000000171 quenching effect Effects 0.000 abstract description 4
- 230000007547 defect Effects 0.000 abstract description 3
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 abstract 3
- 238000001816 cooling Methods 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- GTACSIONMHMRPD-UHFFFAOYSA-N 2-[4-[2-(benzenesulfonamido)ethylsulfanyl]-2,6-difluorophenoxy]acetamide Chemical compound C1=C(F)C(OCC(=O)N)=C(F)C=C1SCCNS(=O)(=O)C1=CC=CC=C1 GTACSIONMHMRPD-UHFFFAOYSA-N 0.000 description 1
- 101710130081 Aspergillopepsin-1 Proteins 0.000 description 1
- 102100031007 Cytosolic non-specific dipeptidase Human genes 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- ZYIGFXHZSKIVOO-OCEACIFDSA-N Oc(cc1)ccc1/C(/c1ccccc1)=C(\c1ccccc1)/c(cc1)ccc1O Chemical compound Oc(cc1)ccc1/C(/c1ccccc1)=C(\c1ccccc1)/c(cc1)ccc1O ZYIGFXHZSKIVOO-OCEACIFDSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000001427 coherent effect Effects 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 230000016507 interphase Effects 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 230000003678 scratch resistant effect Effects 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3215—Polyhydroxy compounds containing aromatic groups or benzoquinone groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/06—Polyurethanes from polyesters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/08—Polyurethanes from polyethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/22—Luminous paints
-
- 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
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
Abstract
The invention discloses an isocyanate curing agent with fluorescence characteristic and a preparation method thereof. The raw materials for preparing the isocyanate curing agent with fluorescence characteristic include polymethylene polyphenyl isocyanate and (E)-4,4'-dihydroxyl tetraphenylethylene, wherein the mass ratio of the polymethylene polyphenyl isocyanate to (E)-4,4'-dihydroxyl tetraphenylethylene is (99:1)-(80:20). The preparation scheme comprises the following steps: dissolving the polymethylene polyphenyl isocyanate and (E)-4,4'-dihydroxyl tetraphenylethylene in certain solvent, stirring and heating for reacting for certain time; cooling; and evaporating with a rotary evaporator to remove the solvent to obtain the designed product solvent. In the invention, the preparation technology of fluorescent paint is simplified, and the defect of aggregation-induced quenching effect easily caused by adopting traditional organic fluorescent molecules is overcome.
Description
Technical field
The present invention relates to fluorescent material field, more particularly to a kind of isocyanate curing agent with fluorescent characteristic and its system
Preparation Method.
Background technology
It is generally used for finish paint based on the paint of polyurethane resin to use, finish paint affects great for the property of coating, with
The development and growth in the living standard of science and technology, the also more and more higher of the requirement to tricoat finish, except with advantageous mechanical property
Can, that is, outside including with good hardness, scratch-resistant, toughness etc., other requirements are added again now, as with special
The characteristics such as light, electricity, sound, to be applied to some special occasions.As topcoat has photoluminescent property, you can make it in decoration, light
Applied in the field such as quick.
Fluorescent paint is a kind of gorgeous quick-dry enamel of color specially fresh, and, with pigment with day-light fluorescence coloring, brightness is up to one for fluorescent paint
As the three times or so painted, be that other paint are incomparable, while color is especially bright-coloured, excitation is high.Fluorescent paint is sent
The wave-length coverage width of light, the color of light can pass through the species of added fluorescent material to change.But for organic fluorescence material
Material, its most application all concentrate on the luminescent properties being dispersed under solvent state, and now fluorescence molecule has with solvent
Stronger intermolecular interaction, but the interphase interaction of its molecule is more faint.Such as：3,4,9,10- perylene 4 formyl-2-imides etc., pass
Though system fluorescence molecule has stronger fluorescent characteristic under solution state, fluorescent characteristic drastically declines even under solid states
Disappear.This phenomenon is determined to affect by its molecular structure：Conventional fluorescent molecule typically all has the molecule in the fair face of big conjugation
Structure, causes have stronger intermolecular force i.e. π-π stackings (similar to the effect of H- aggregations) between molecule, produced
Intramolecule electron transition dipole moment phenomenon causes when it is in coherent condition (solid state is scattered in poor solvent), swashs
Sending out group can form between fluorescence molecule, and this normally results in excitation energy and dissipates in radiationless form, fluorescence molecule
The fluorescence meeting red shift for being sent and remitted its fury, this phenomenon is referred to as aggregation inducing quenching effect.
Due to this aggregation quenching effect, application of traditional organic fluorescence small molecule material in fluorescent paint is caused to be limited
System.In view of this, a kind of isocyanate curing agent with fluorescent characteristic of exploitation and preparation method thereof is necessary in fact, with solution
State problem.
The content of the invention
For the deficiencies in the prior art part, it is an object of the invention to provide a kind of isocyanates with fluorescent characteristic is solid
Agent and preparation method thereof, defect or problem that the doping of traditional organic fluorescent powder of forgoing is brought are synthesized with fluorescence
The isocyanate curing agent of characteristic and PEPA or PPG reaction solidification, you can obtain superior performance and with glimmering
The topcoat of light property.
In order to reach above-mentioned technique effect, the present invention is achieved through the following technical solutions：
A kind of isocyanate curing agent with fluorescent characteristic, preparing the raw material required for the product includes：Polymethylene
Many phenyl isocyanates and (E) -4,4 '-dihydroxy tetraphenylethylene, wherein, the polymethylene multi-phenenyl isocyanate with
(E) -4, the quality of 4 '-dihydroxy tetraphenylethylene is 99 than scope:1～80:20, (E) -4,4 '-dihydroxy tetraphenyl
The chemical structural formula of ethene is as follows：
Preferably, the polymethylene multi-phenenyl isocyanate is the product of Chinese Wanhua Chemical Group Co., Ltd.
Product, its model：PM200.
Further, this case also provides a kind of method for preparing the above-mentioned isocyanate curing agent with fluorescent characteristic, its
It is obtained by following steps：
The first step：Polymethylene multi-phenenyl isocyanate and (E) -4,4 '-dihydroxy tetraphenylethylene are dissolved in necessarily
In solvent, the concentration range of mixture is：0.5g/ml～10g/ml；
Second step：50～80 DEG C are warming up under nitrogen protection, and with 500 revs/min～2000 revs/min of speed, stirring is anti-
Answer 2～8 hours；
3rd step：The product for obtaining is evaporated through Rotary Evaporators, solvent is removed, the isocyanide with fluorescent characteristic is obtained
Acid esters curing agent.
Preferably, the solvent can be：In tetrahydrofuran, dimethylbenzene, ethyl acetate, butyl acetate at least one
Kind.
The invention has the beneficial effects as follows：
1st, the isocyanate curing agent with fluorescent characteristic of cross-linkable solidifying is prepared for, the preparation of conventional fluorescent paint is reduced
When need the preparation process of doping fluorescent powder again, simplify the preparation technology of fluorescent paint；
2nd, the defect of aggregation inducing quenching effect that the organic fluorescence powder of conventional fluorescent paint doping has itself is avoided；
3rd, the doping of fluorescent material is avoided, is conducive to solidified paint that there is good mechanical property, it is to avoid fluorescent material dry linting
Phenomenon occurs.
Specific embodiment
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 restriction the scope of the present invention.In addition, it is to be understood that after the content for having read instruction of the present invention, people in the art
Member can make various changes or modifications to the present invention, and these equivalent form of values equally fall within the application appended claims and limited
Scope.
Embodiment one
A kind of isocyanate curing agent with fluorescent characteristic, preparing the raw material required for the product includes：
Polymethylene multi-phenenyl isocyanate (product of Chinese Wanhua Chemical Group Co., Ltd., its model：
PM200) and (E) -4,4 '-dihydroxy tetraphenylethylene, wherein, polymethylene multi-phenenyl isocyanate and (E) -4,4 '-dihydroxy
The mass ratio of base tetraphenylethylene is 99:1, (E) -4, the chemical structural formula of 4 '-dihydroxy tetraphenylethylene is as follows：
Isocyanate curing agent with fluorescent characteristic is obtained by following steps：
The first step：Polymethylene multi-phenenyl isocyanate and (E) -4,4 '-dihydroxy tetraphenylethylene are dissolved in into diformazan
In benzene solvent, the concentration of mixture is：10g/ml；
Second step：80 DEG C are warming up under nitrogen protection, with 2000 revs/min of speed, stirring reaction 2 hours；
3rd step：The product for obtaining is evaporated through Rotary Evaporators, solvent is removed, the isocyanide with fluorescent characteristic is obtained
Acid esters curing agent.
Embodiment two
A kind of isocyanate curing agent with fluorescent characteristic, preparing the raw material required for the product includes：Polymethylene
Many phenyl isocyanate (product of Chinese Wanhua Chemical Group Co., Ltd., its model：) and (E)-4,4 ' PM200-
Dihydroxy tetraphenylethylene, wherein, polymethylene multi-phenenyl isocyanate and (E) -4, the quality of 4 '-dihydroxy tetraphenylethylene
Than for 95:5, (E) -4, the chemical structural formula of 4 '-dihydroxy tetraphenylethylene is as follows：
Isocyanate curing agent with fluorescent characteristic is obtained by following steps：
The first step：Polymethylene multi-phenenyl isocyanate and (E) -4,4 '-dihydroxy tetraphenylethylene are dissolved in into tetrahydrochysene
In THF solvent, the concentration of mixture is：5g/ml；
Second step：70 DEG C are warming up under nitrogen protection, with 1500 revs/min of speed, stirring reaction 4 hours；
3rd step：The product for obtaining is evaporated through Rotary Evaporators, solvent is removed, the isocyanide with fluorescent characteristic is obtained
Acid esters curing agent.
Embodiment three
A kind of isocyanate curing agent with fluorescent characteristic, preparing the raw material required for the product includes：
Polymethylene multi-phenenyl isocyanate (product of Chinese Wanhua Chemical Group Co., Ltd., its model：
PM200) and (E) -4,4 '-dihydroxy tetraphenylethylene, wherein, polymethylene multi-phenenyl isocyanate and (E) -4,4 '-dihydroxy
The mass ratio of base tetraphenylethylene is 90:10, (E) -4, the chemical structural formula of 4 '-dihydroxy tetraphenylethylene is as follows：
Isocyanate curing agent with fluorescent characteristic is obtained by following steps：
The first step：Polymethylene multi-phenenyl isocyanate and (E) -4,4 '-dihydroxy tetraphenylethylene are dissolved in into acetic acid
In butyl ester solvent, the concentration of mixture is：4g/ml；
Second step：60 DEG C are warming up under nitrogen protection, with 1000 revs/min of speed, stirring reaction 6 hours；
3rd step：The product for obtaining is evaporated through Rotary Evaporators, solvent is removed, the isocyanide with fluorescent characteristic is obtained
Acid esters curing agent.
Example IV
A kind of isocyanate curing agent with fluorescent characteristic, preparing the raw material required for the product includes：
Polymethylene multi-phenenyl isocyanate (product of Chinese Wanhua Chemical Group Co., Ltd., its model：
PM200) and (E) -4,4 '-dihydroxy tetraphenylethylene, wherein, polymethylene multi-phenenyl isocyanate and (E) -4,4 '-dihydroxy
The mass ratio of base tetraphenylethylene is 80:20, (E) -4, the chemical structural formula of 4 '-dihydroxy tetraphenylethylene is as follows：
Isocyanate curing agent with fluorescent characteristic is obtained by following steps：
The first step：Polymethylene multi-phenenyl isocyanate and (E) -4,4 '-dihydroxy tetraphenylethylene are dissolved in into acetic acid
In ethyl ester solvent, the concentration of mixture is：0.5g/ml；
Second step：50 DEG C are warming up under nitrogen protection, with 500 revs/min of speed, stirring reaction 8 hours；
3rd step：The product for obtaining is evaporated through Rotary Evaporators, solvent is removed, the isocyanide with fluorescent characteristic is obtained
Acid esters curing agent.
Although embodiment of the present invention is disclosed as above, it is not limited in listed fortune in specification and embodiment
With, it can be applied to completely various suitable the field of the invention, for those skilled in the art, can be easily real
Now other modification, therefore under the universal limited without departing substantially from claim and equivalency range, the present invention is not limited to
Specific details and shown here as the legend with description.
Claims (4)
1. a kind of isocyanate curing agent with fluorescent characteristic, it is characterised in that preparing the raw material required for the product includes：
Polymethylene multi-phenenyl isocyanate and (E) -4,4 '-dihydroxy tetraphenylethylene, wherein, the polymethylene polyphenyl isocyanide
Acid esters and (E) -4, the quality of 4 '-dihydroxy tetraphenylethylene is 99 than scope:1～80:20, (E) -4,4 '-dihydroxy
The chemical structural formula of tetraphenylethylene is as follows：
2. there is as claimed in claim 1 the isocyanate curing agent of fluorescent characteristic, it is characterised in that the polymethylene is more
Phenyl isocyanate is the product of Chinese Wanhua Chemical Group Co., Ltd., its model：PM200.
3. a kind of preparation method of the isocyanate curing agent with fluorescent characteristic as any one of claim 1 or 2,
Characterized in that, being obtained by following steps：
The first step：Polymethylene multi-phenenyl isocyanate and (E) -4,4 '-dihydroxy tetraphenylethylene are dissolved in into certain solvent
In, the concentration range of mixture is：0.5g/ml～10g/ml；
Second step：50～80 DEG C are warming up under nitrogen protection, with 500 revs/min～2000 revs/min of speed, stirring reaction 2～
8 hours；
3rd step：The product for obtaining is evaporated through Rotary Evaporators, solvent is removed, the isocyanates with fluorescent characteristic is obtained
Curing agent.
4. there is as claimed in claim 3 the preparation method of the isocyanate curing agent of fluorescent characteristic, it is characterised in that described
Solvent can be：At least one in tetrahydrofuran, dimethylbenzene, ethyl acetate, butyl acetate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611146614.6A CN106632977A (en) | 2016-12-13 | 2016-12-13 | Isocyanate curing agent with fluorescence characteristic and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611146614.6A CN106632977A (en) | 2016-12-13 | 2016-12-13 | Isocyanate curing agent with fluorescence characteristic and preparation method thereof |
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|---|---|
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Family
ID=58825200
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107629184A (en) * | 2017-09-26 | 2018-01-26 | 东北师范大学 | A kind of S dinaphthols polyurethane and preparation method and application |
| CN109400836A (en) * | 2018-12-06 | 2019-03-01 | 黑龙江大学 | Urethane derivative and its preparation method and application containing tertiary aromatic amine structure and tetraphenyl ethylene group |
| CN109575230A (en) * | 2018-12-06 | 2019-04-05 | 黑龙江大学 | A kind of multifunctional polyurethane derivative and its preparation method and application |
| CN109912773A (en) * | 2019-03-29 | 2019-06-21 | 中国科学院宁波材料技术与工程研究所 | A kind of shape memory polyurethane and preparation method thereof |
| CN110527283A (en) * | 2019-07-26 | 2019-12-03 | 河北大学 | A kind of PES base flexible white fluorescent polyester and preparation method thereof |
| CN114560984A (en) * | 2022-04-07 | 2022-05-31 | 安徽科润美新材料科技股份有限公司 | Self-monitoring polyurethane and preparation method and application thereof |
| CN114920904A (en) * | 2022-05-31 | 2022-08-19 | 郑州大学 | Preparation method and application of colorless transparent high-strength polyurethane anti-counterfeiting material |
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| CN1526071A (en) * | 2001-07-02 | 2004-09-01 | ����˹ҽ������˾ | Two-photon absorbing dipyrromethenboron difluoride dyes and their applications |
| CN104114646A (en) * | 2011-12-23 | 2014-10-22 | 通用电气公司 | High-density fluorescent dye clusters |
| CN106008920A (en) * | 2016-06-26 | 2016-10-12 | 苏州吉人高新材料股份有限公司 | Modified epoxy resin with fluorescent characteristic and preparation method thereof |
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| CN107629184B (en) * | 2017-09-26 | 2020-06-23 | 东北师范大学 | A kind of R-binaphthol polyurethane and preparation method and application |
| CN109400836A (en) * | 2018-12-06 | 2019-03-01 | 黑龙江大学 | Urethane derivative and its preparation method and application containing tertiary aromatic amine structure and tetraphenyl ethylene group |
| CN109575230A (en) * | 2018-12-06 | 2019-04-05 | 黑龙江大学 | A kind of multifunctional polyurethane derivative and its preparation method and application |
| CN109575230B (en) * | 2018-12-06 | 2021-01-22 | 黑龙江大学 | A kind of preparation method and application of multifunctional polyurethane derivative |
| CN109912773A (en) * | 2019-03-29 | 2019-06-21 | 中国科学院宁波材料技术与工程研究所 | A kind of shape memory polyurethane and preparation method thereof |
| CN109912773B (en) * | 2019-03-29 | 2021-10-26 | 中国科学院宁波材料技术与工程研究所 | Shape memory polyurethane and preparation method thereof |
| CN110527283A (en) * | 2019-07-26 | 2019-12-03 | 河北大学 | A kind of PES base flexible white fluorescent polyester and preparation method thereof |
| CN110527283B (en) * | 2019-07-26 | 2021-05-11 | 河北大学 | PES (polyether sulfone) based flexible white fluorescent polyester and preparation method thereof |
| CN114560984A (en) * | 2022-04-07 | 2022-05-31 | 安徽科润美新材料科技股份有限公司 | Self-monitoring polyurethane and preparation method and application thereof |
| CN114920904A (en) * | 2022-05-31 | 2022-08-19 | 郑州大学 | Preparation method and application of colorless transparent high-strength polyurethane anti-counterfeiting material |
| CN114920904B (en) * | 2022-05-31 | 2024-01-30 | 郑州大学 | Preparation method and application of colorless transparent high-strength polyurethane anti-counterfeiting material |
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Application publication date: 20170510 |