CN107793503A - A kind of ultraviolet initiator and its synthetic method - Google Patents
A kind of ultraviolet initiator and its synthetic method Download PDFInfo
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- CN107793503A CN107793503A CN201710913670.6A CN201710913670A CN107793503A CN 107793503 A CN107793503 A CN 107793503A CN 201710913670 A CN201710913670 A CN 201710913670A CN 107793503 A CN107793503 A CN 107793503A
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- methyl isophthalic
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- 239000003999 initiator Substances 0.000 title claims abstract description 22
- 238000010189 synthetic method Methods 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 33
- 238000003756 stirring Methods 0.000 claims description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- 238000010792 warming Methods 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 5
- 238000007792 addition Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 238000009413 insulation Methods 0.000 claims description 4
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 claims description 3
- DTZKVZKYSZUBAG-UHFFFAOYSA-N 2-chloro-2-methylpropanoyl chloride Chemical compound CC(C)(Cl)C(Cl)=O DTZKVZKYSZUBAG-UHFFFAOYSA-N 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 239000012043 crude product Substances 0.000 claims description 3
- 230000006837 decompression Effects 0.000 claims description 3
- 238000006735 epoxidation reaction Methods 0.000 claims description 3
- 239000010813 municipal solid waste Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000012044 organic layer Substances 0.000 claims description 3
- 238000011084 recovery Methods 0.000 claims description 3
- 238000010583 slow cooling Methods 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 3
- 238000003786 synthesis reaction Methods 0.000 claims 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 230000008023 solidification Effects 0.000 abstract description 8
- 238000007711 solidification Methods 0.000 abstract description 8
- 239000002253 acid Substances 0.000 abstract description 4
- 150000001336 alkenes Chemical class 0.000 abstract description 4
- 238000002425 crystallisation Methods 0.000 abstract description 4
- 230000008025 crystallization Effects 0.000 abstract description 4
- 150000002148 esters Chemical class 0.000 abstract description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 239000000178 monomer Substances 0.000 abstract description 3
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 230000004888 barrier function Effects 0.000 abstract description 2
- 208000012839 conversion disease Diseases 0.000 abstract description 2
- 239000005548 dental material Substances 0.000 abstract description 2
- 229920002120 photoresistant polymer Polymers 0.000 abstract description 2
- 238000006116 polymerization reaction Methods 0.000 abstract description 2
- 230000035899 viability Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 150000002780 morpholines Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F120/10—Esters
- C08F120/12—Esters of monohydric alcohols or phenols
- C08F120/14—Methyl esters, e.g. methyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polymerisation Methods In General (AREA)
- Dental Preparations (AREA)
Abstract
The invention discloses a kind of ultraviolet initiator and its synthetic method, the initiator triggers olefin(e) acid ester type compound monomer internal double bond active under action of ultraviolet light, causes such compound polymerization, is crosslinked so as to complete solidification process.This initiator can be used cooperatively with other curing agent and prepare high density compact disc, photosensitive printed board, microporous barrier, dental material, photoresist, offset ink etc..The ultraviolet initiator and synthetic method of the present invention, technological operation is simple, equipment requirement is low, and discarded object is few, environmentally friendly, reaction conversion ratio can reach more than 95%, product purity is high, can reach more than 99.5%, commercial viability is high, dissolubility is fabulous in the product organic solvent, and the crystallization time is longer.
Description
Technical field
The present invention relates to a kind of ultraviolet initiator and its synthetic method.
Background technology
Ultraviolet light solidification mainly triggers matrix resin aggressiveness by ultraviolet excitation light trigger, so as to reach solidification mesh
's.Ultraviolet initiator is the middle important component that ultraviolet cured adhesive sticks agent, and its effect is：Chemistry occurs instead after absorbing ultraviolet light
Should, the reactive radical species for triggering solidification are produced, so that polymerisation solidification occurs for active group in adhesive.It is existing ultraviolet
Light trigger efficiency of initiation is low, and synthetic reaction difficulty is big, and yield is not high.
The content of the invention
It is an object of the invention to provide a kind of ultraviolet initiator and its synthetic method, and the initiator is under action of ultraviolet light
Trigger olefin(e) acid ester type compound (example acrylate, methacrylate) monomer internal double bond activity, cause such compound to polymerize,
It is crosslinked so as to complete solidification process.This initiator can with other curing agent with the use of prepare high density compact disc, photosensitive printed board,
Microporous barrier, dental material, photoresist, offset ink etc..
The used to achieve the above object technical scheme of the present invention is：A kind of ultraviolet initiator, the initiator are
2- methyl isophthalic acids-(9.9- dialkyl fluorenyls) -2- morpholinyl -1- acetone, its structural formula are：
Wherein, R=CnH2n+1, n=2~8.
The synthetic method of above-mentioned ultraviolet initiator is that following three step of reaction point is carried out：
1)
2)
3)
Further, the specific synthetic method of step 1) is：Fluorenes adds dichloromethane, chloro isobutyryl chloride, opens stirring,
- 5-0 DEG C are cooled to, adds alchlor, less than 10 DEG C reaction 6h is finished, reaction solution is poured into and mixed by what hydrochloric acid and trash ice formed
Acidolysis in compound, add dichloromethane and stir 3 hours, concentration of organic layers after liquid separation, methanol, cooling knot are added when there is solid
Crystalline substance, filtering, drying obtain celadon solid, the chloro- 1- acetone of as 2- methyl isophthalic acids-fluorenyl -2-.
Further, the specific synthetic method of step 2) is：Nitrogen protection is lower to add 2- methyl isophthalic acids-chloro- 1- third of fluorenyl -2-
With sodium methoxide epoxidation reaction occurs for ketone, oxidized calcium treating, is incubated 68 DEG C and reacts 6 hours, is cooled to 50 DEG C of addition morpholines and protects
125 DEG C are warming up to after temperature stirring 0.5h, methanol, stirring reaction 14h are reclaimed by rectifier unit in temperature-rise period, cooling decompression returns
Morpholine is received, crude product adds toluene and the stirring 2 hours of 50 DEG C of activated carbon is decolourized, and filtering, removal of solvent under reduced pressure toluene adds methanol liter
Temperature crystallization, obtains yellow solid, as 2- methyl isophthalic acids-fluorenyl -2- morpholinyl -1- acetone to return stirring 1.0h slow coolings；
Further, the specific synthetic method of step 3) is：2- methyl isophthalic acids-fluorenyl -2- morpholinyl -1- acetone, the tetrabutyl
Ammonium bromide and chlorobutane mixing, it is warming up to 78 DEG C and the 50%NaOH aqueous solution is added dropwise to system, drip and finish 82 DEG C of insulation reaction 4.0h, instead
It should terminate to cool, add water and toluene stirring 0.5h, liquid separation is organic to be added to activated carbon decolorizing, filtering, removal of solvent under reduced pressure first
Benzene adds methanol crystallizing at room temperature 6~8 hours, continues to be cooled to 0~5 DEG C of stirring 5h after separating out solid, filters, drying, obtain white
Color solid 2- methyl isophthalic acids-(9.9- dibutylfluorenyls) -2- morpholinyl -1- acetone.
The ultraviolet initiator and synthetic method of the present invention, technological operation is simple, and equipment requirement is low, and discarded object is few, to ring
Border is friendly, and reaction conversion ratio can reach more than 95%, and product purity is high, can reach more than 99.5%, and commercial viability is high,
Dissolubility is fabulous in the product organic solvent, and the crystallization time is longer.
Embodiment
Explanation is further explained to the present invention with reference to specific embodiment.
The ultraviolet initiator of the present invention is 2- methyl isophthalic acids-(9.9- dialkyl fluorenyls) -2- morpholinyl -1- acetone, and it is tied
Structure formula is：
Wherein, R=CnH2n+1, n=2~8.
Its synthetic method is specially：
1) fluorenes 35.5g adds 120g dichloromethane, chloro isobutyryl chloride 30.1g, opens stirring, is cooled to -5-0 DEG C, point
(10 times) addition alchlors are criticized, less than 10 DEG C reaction 6h is finished, reaction solution is poured into what is be made up of 50g hydrochloric acid and 150g trash ices
Acidolysis in mixture, add 150g dichloromethane and stir 3 hours.Concentration of organic layers after liquid separation, 150g is added when there is solid
Methanol, decrease temperature crystalline, filtering, drying obtain the chloro- 1- acetone of celadon solid 46.3g, as 2- methyl isophthalic acid-fluorenyl -2-, contained
Amount：98.5%, yield：80%；
2) 2- methyl isophthalic acids-chloro- 1- acetone 27g of fluorenyl -2- are added in the lower 250ml there-necked flasks of nitrogen protection, is aoxidized through 1.76g
With 7.0g sodium methoxides epoxidation reaction occurs for calcium treating, is incubated 68 DEG C and reacts 6 hours, is cooled to 50 DEG C and adds the insulation of 68g morpholines
125 DEG C are warming up to after stirring 0.5h, methanol, stirring reaction 14h, cooling decompression recovery are reclaimed by rectifier unit in temperature-rise period
Morpholine, crude product adds 170g toluene and the stirring 2 hours of 50 degree of 1.76g activated carbons is decolourized, filtering.Removal of solvent under reduced pressure toluene adds
60g methanol is warming up to return stirring 1.0h slow coolings, crystallization, obtains yellow solid 31.2g, as 2- methyl isophthalic acid-fluorenyls-
2- morpholinyl -1- acetone, yield 77%, content 98.5%.
3) weigh 2- methyl isophthalic acids-fluorenyl -2- morpholinyl -1- acetone 30g, TBAB 0.6g and 34 grams of chlorobutane is mixed
Close, be warming up to 78 DEG C and 50%NaOH aqueous solution 72g is added dropwise to system, drip and finish 82 DEG C of insulation reaction 4.0h, reaction terminates cooling, added
Enter water 50g and toluene 58g stirring 0.5h, liquid separation, it is organic be added to 3g activated carbon decolorizings, filtering, removal of solvent under reduced pressure toluene add
Enter 38g methanol crystallizing at room temperature 6~8 hours, continue to be cooled to 0~5 DEG C of stirring 5h after separating out solid, filter, drying, obtain white
Solid 2- methyl isophthalic acids-(9.9- dibutylfluorenyls) -2- morpholinyl -1- acetone, 30.5g, yield 80%, content 99.5%.
This product triggers double in olefin(e) acid ester type compound (example acrylate, methacrylate) monomer under action of ultraviolet light
Key activity, cause such compound polymerization, be crosslinked so as to complete solidification process, can directly be inferred to solidify by product structure
Principle is as follows：
The initiation and growth of chain：
Olefin(e) acid ester type compound solidification process is realized based on above-mentioned principle.
Photoinitiation Property is studied：
| Numbering | Title | Source |
| 1 | 2- methyl isophthalic acids-(9.9- diethyl fluorenyl) -2- morpholinyl -1- acetone | Self-control |
| 2 | 2- methyl isophthalic acids-(9.9- dibutylfluorenyls) -2- morpholinyl -1- acetone | Self-control |
| 3 | 2- methyl isophthalic acids-(9.9- dioctyls fluorenyl) -2- morpholinyl -1- acetone | Self-control |
Prepolymer：Methyl acrylate
Laboratory apparatus：Uv analyzer
Product Photoinitiation Property is tested：
| Numbering | Aerobic hardening time (min) | Anaerobic hardening time (min) | Temperature (DEG C) |
| 1 | 63 | 48 | 25 |
| 2 | 70 | 50 | 25 |
| 3 | 78 | 55 | 25 |
Dissolubility is fabulous in organic solvent for product, with 2- methyl isophthalic acids-(9.9- dibutylfluorenyls) -2- morpholinyls -1- third
(sample 100g is taken exemplified by ketone), and data are as follows:
Claims (5)
1. a kind of ultraviolet initiator, it is characterised in that the initiator is 2- methyl isophthalic acids-(9.9- dialkyl fluorenyls) -2-
Quinoline base -1- acetone, its structural formula are：
Wherein, R=CnH2n+1, n=2~8.
2. the synthetic method of ultraviolet initiator as claimed in claim 1, it is characterised in that following three step of reaction point is carried out：
1)
2)
3)
3. the synthetic method of ultraviolet initiator according to claim 2, it is characterised in that the specific synthesis side of step 1)
Method is：Fluorenes adds dichloromethane, chloro isobutyryl chloride, opens stirring, is cooled to -5-0 DEG C, adds alchlor, finishes 10 DEG C
6h is reacted below, reaction solution is poured into acidolysis in the mixture being made up of hydrochloric acid and trash ice, is added dichloromethane and is stirred 3 hours,
Concentration of organic layers after liquid separation, methanol is added when there is solid, decrease temperature crystalline, filtering, dries and obtains celadon solid, as 2-
The chloro- 1- acetone of methyl isophthalic acid-fluorenyl -2-.
4. the synthetic method of ultraviolet initiator according to claim 2, it is characterised in that the specific synthesis side of step 2)
Method is：Nitrogen protection is lower to add 2- methyl isophthalic acids-chloro- 1- acetone of fluorenyl -2-, and oxidized calcium treating and sodium methoxide generation epoxidation are anti-
Should, it is incubated 68 DEG C and reacts 6 hours, is warming up to 125 DEG C after being cooled to 50 DEG C of addition morpholine insulated and stirred 0.5h, leads in temperature-rise period
Rectifier unit recovery methanol is crossed, stirring reaction 14h, cooling decompression recovery morpholine, crude product adds toluene and 50 DEG C of activated carbon stirs 2
Hour decolourizes, and filtering, removal of solvent under reduced pressure toluene adds methanol and is warming up to return stirring 1.0h slow coolings, crystallizes, obtains Huang
Color solid, as 2- methyl isophthalic acid-fluorenyl -2- morpholinyl -1- acetone；
5. the synthetic method of ultraviolet initiator according to claim 2, it is characterised in that the specific synthesis side of step 3)
Method is：2- methyl isophthalic acids-fluorenyl -2- morpholinyl -1- acetone, TBAB and chlorobutane mixing, are warming up to 78 DEG C of dropwise additions
For the 50%NaOH aqueous solution to system, drop finishes 82 DEG C of insulation reaction 4.0h, and reaction terminates cooling, addition water and toluene stirring 0.5h,
Liquid separation, it is organic be added to activated carbon decolorizing, filtering, removal of solvent under reduced pressure toluene add methanol crystallizing at room temperature 6~8 hours, separate out
Continue to be cooled to 0~5 DEG C of stirring 5h after solid, filter, drying, obtain white solid 2- methyl isophthalic acids-(9.9- dibutylfluorenyls)-
2- morpholinyl -1- acetone.
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| CN201710913670.6A CN107793503A (en) | 2017-09-28 | 2017-09-28 | A kind of ultraviolet initiator and its synthetic method |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108117616A (en) * | 2017-11-22 | 2018-06-05 | 惠州市华泓新材料股份有限公司 | Dibutylfluorenyl derivative and its application as photoinitiator |
| WO2020241328A1 (en) * | 2019-05-29 | 2020-12-03 | 株式会社Ｄｎｐファインケミカル | Photosensitive colored resin composition for color filter, cured object, color filter, and display device |
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| CN103012317A (en) * | 2012-12-23 | 2013-04-03 | 惠州市华泓新材料有限公司 | Alkyl phenyl derivative and application of alkyl phenyl derivative as photoinitiator |
| CN106883114A (en) * | 2015-12-15 | 2017-06-23 | 常州强力先端电子材料有限公司 | A kind of fluorenes class polyfunctionality light trigger and its preparation and application |
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| US6673850B1 (en) * | 1999-05-10 | 2004-01-06 | Ciba Specialty Chemicals Corporation | Photoinitiators and their applications |
| CN103012317A (en) * | 2012-12-23 | 2013-04-03 | 惠州市华泓新材料有限公司 | Alkyl phenyl derivative and application of alkyl phenyl derivative as photoinitiator |
| CN106883114A (en) * | 2015-12-15 | 2017-06-23 | 常州强力先端电子材料有限公司 | A kind of fluorenes class polyfunctionality light trigger and its preparation and application |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108117616A (en) * | 2017-11-22 | 2018-06-05 | 惠州市华泓新材料股份有限公司 | Dibutylfluorenyl derivative and its application as photoinitiator |
| WO2019101142A1 (en) * | 2017-11-22 | 2019-05-31 | 惠州市华泓新材料股份有限公司 | Dibutylfluorene derivative and application thereof as photoinitiator |
| CN108117616B (en) * | 2017-11-22 | 2019-08-09 | 惠州市华泓新材料股份有限公司 | Dibutylfluorenyl derivative and its application as photoinitiator |
| US11560362B2 (en) | 2017-11-22 | 2023-01-24 | Huizhou Huahong New Material Co., Ltd. | Dibutylfluorene derivative and application thereof as photoinitiator |
| WO2020241328A1 (en) * | 2019-05-29 | 2020-12-03 | 株式会社Ｄｎｐファインケミカル | Photosensitive colored resin composition for color filter, cured object, color filter, and display device |
| JP6817503B1 (en) * | 2019-05-29 | 2021-01-20 | 株式会社Ｄｎｐファインケミカル | Photosensitive colored resin compositions for color filters, cured products, color filters, and display devices |
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