CN109384670A - A kind of water-soluble light trigger and preparation method thereof - Google Patents
A kind of water-soluble light trigger and preparation method thereof Download PDFInfo
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- CN109384670A CN109384670A CN201710650594.4A CN201710650594A CN109384670A CN 109384670 A CN109384670 A CN 109384670A CN 201710650594 A CN201710650594 A CN 201710650594A CN 109384670 A CN109384670 A CN 109384670A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- -1 4- (2- hydroxy ethoxy) phenyl Chemical group 0.000 claims abstract description 13
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000008065 acid anhydrides Chemical class 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- 239000013067 intermediate product Substances 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 238000000926 separation method Methods 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000012535 impurity Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 5
- 238000005227 gel permeation chromatography Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 238000001291 vacuum drying Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract description 3
- 239000000376 reactant Substances 0.000 abstract description 3
- 150000003839 salts Chemical class 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000178 monomer Substances 0.000 description 10
- 238000010907 mechanical stirring Methods 0.000 description 8
- 230000000977 initiatory effect Effects 0.000 description 6
- 239000003999 initiator Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000000016 photochemical curing Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000012805 post-processing Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- MFGALGYVFGDXIX-UHFFFAOYSA-N 2,3-Dimethylmaleic anhydride Chemical compound CC1=C(C)C(=O)OC1=O MFGALGYVFGDXIX-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
-
- 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
Abstract
The invention belongs to field of light-sensitive high molecular materials.The present invention is based on 2- hydroxyl -1- (4- (2- hydroxy ethoxy) phenyl) -2- methyl acetone (Darocur 2959), triethylamine, different types of acid anhydrides to be prepared for a kind of water-soluble light trigger.By introducing carboxyl in the molecular structure, in the form that it is generated to quaternary ammonium salt with reactant salt, its water solubility is improved while guaranteeing its space charge force.Synthesis step of the invention is simple, and preparation cost is low, and the water solubility of product is good, has wide practical use in UV-curable waterborne field.
Description
Technical field
The invention belongs to field of light-sensitive high molecular materials, a kind of water-soluble light trigger and preparation method thereof.
Background technique
Photocuring technology is mild as a kind of reaction condition, reaction speed is fast, to substrate damage it is small, without three waste discharge,
Green friendly technology free from environmental pollution, appearance achieve quick development so far.And in ink, coating, photoresist, micro- electricity
Son, biomaterial and teeth repairing material etc. are widely used in.In general, photocuring system includes oligomerisation
Object, monomer, photoinitiator and auxiliary agent, though wherein the shared content of photoinitiator is less plays vital work to whole system
With, because initiator can absorb luminous energy and generate reactive species, free radical or ion under the ultraviolet light of certain wavelength, from
And cause monomer polymerization.
Compared with conventional curing technology, photocuring technology already has very big superiority.In most of photocuring body
In system, using monomer come the reactive diluent for the system of serving as, but monomer reduction system viscosity is limited, some monomers are readily volatilized
And smell and toxicity are generated, and the possible unreacted of some monomers remains in system completely under illumination condition, in use process
In can move to product surface influence use.So in order to overcome these drawbacks, water soluble photo-curable system enters into researcher
Sight.Water soluble photo-curable system makees diluent with water, and water is cheaply easy to get safely, it can be achieved that monomer-free formula, avoids by list
Cure shrinkage caused by body is easy to adjust viscosity, is suitable for various spraying methods, without smell and toxicity.It is water-soluble light-initiated
Agent caused the close attention of people as the most important a part of water soluble photo-curable system in recent years, studies and answers
With also at heat subject.
Summary of the invention
The technical problem to be solved by the present invention is having to solve general photocuring system monomer regulation system viscosity
Limit, and the problem of monomer is readily volatilized, toxic and uncured monomer can move to product surface, the present invention provides one
Kind water-soluble light trigger, makees diluent with water, solves with monomer and serve as reactive diluent bring a series of problems.It is logical
It crosses and introduces carboxyl in photoinitiator molecules structure, in the form that it is generated to quaternary ammonium salt with reactant salt, guaranteeing that its is light-initiated
Its water solubility is improved while active.The raising of solubility and initiation oligomer efficiency are drawn with unmodified preceding photoinitiator in water
It is similar to send out efficiency, it is sufficient to illustrate that it is a kind of good water-soluble light trigger.The present invention provides this water solubility is light-initiated
The preparation method of agent, reaction process is simple, and reaction condition is mild, and post-processing is simple and is easy purifying.
The present invention solves the technological means that technical problem uses: a kind of water-soluble light trigger, structure are as follows:
The preparation reaction equation of water-soluble light trigger are as follows:
The preparation method of the water-soluble light trigger, includes the following steps:
2- hydroxyl -1- (4- (2- hydroxy ethoxy) phenyl) -2- methyl acetone (Darocur is added in step 1) in a solvent
2959) it and acid anhydrides, is stirred under heating condition；
The anhydrous AlCl of catalyst is added in step 2) in the mixture of step 1)3Reaction 1 hour；
Step 3) after the reaction was completed, is filtered to remove solid impurity, and revolving removes solvent, finally vacuum drying remove solvent and
After water, intermediate product A is obtained；
Intermediate product A and triethylamine is added in step 4) in a solvent, reacts 16 hours at room temperature；
Step 5) after the reaction was completed, is washed three times with hydrochloric acid or ethyl acetate, solvent is rotated and is removed, gel chromatographic columns are used
Separation further purification, finally obtains clean product.
Specifically, the acid anhydrides type is more；
Specifically, the molar ratio of 2959 photoinitiator of Darocur and acid anhydrides is 1.5:1；
Specifically, the temperature of the heating condition is 90-110 DEG C；
Specifically, the molar ratio of the intermediate product A and triethylamine is 1:1；
Specifically, the solvent is one or more of toluene, pyridine, tetrahydrofuran and carbon tetrachloride.
The beneficial effects of the present invention are: introducing carboxyl in photoinitiator molecules structure, it is being generated into season with reactant salt
The form of ammonium salt improves its water solubility while guaranteeing its space charge force.The raising and initiation of solubility are oligomeric in water
Object efficiency is similar to unmodified preceding photoinitiator efficiency of initiation, it is sufficient to illustrate that it is a kind of good water-soluble light trigger.This
Invention provides the preparation method of this water-soluble light trigger, and reaction process is simple, and reaction condition is mild, and post-processing is simple simultaneously
And it is easy purifying.
Specific embodiment
The present invention will be described in detail for the following example, but does not limit the scope of the invention.
Embodiment 1:
The structural formula of compound 1:
By 2- hydroxyl -1- (4- (2- hydroxy ethoxy) phenyl) -2- methyl acetone (Darocur 2959) (33.69g,
0.15mol), maleic anhydride (9.81g, 0.1mol), the anhydrous AlCl of catalyst3(10.67,0.08mol) and 100ml toluene are molten
Liquid is added in the 250ml three-necked flask for being equipped with mechanical stirring and constant pressure funnel, 90 DEG C of stirring 60min.Reaction terminates
Afterwards, be filtered to remove solid impurity, 3 washing, liquid separation removings water phases, revolving remove toluene, finally vacuum drying remove solvent with
After water, intermediate product A is obtained；The intermediate product A and triethylamine (10.22g, 0.1mol) being then dissolved in 60ml carbon tetrachloride
It is added in the 250ml three-necked flask for being equipped with mechanical stirring and constant pressure funnel, 16h is stirred at room temperature.After the reaction was completed, it uses
Hydrochloric acid or ethyl acetate are washed three times, and solvent is rotated and is removed, is further purified, is finally obtained pure with gel chromatography post separation
Product 1, and Structural Identification is carried out by NMR spectrum.
1HNMR(400MHz,Acetone-d6)δ(ppm):6.99-7.94(4H,aromatics),3.28-4.52
(10H,-CH2), 6.44-7.94 (2H ,-CH=), 4.62 (1H ,-OH) 1.25-1.35 (15H ,-CH3).
Embodiment 2
The structural formula of compound 2 are as follows:
By 2- hydroxyl -1- (4- (2- hydroxy ethoxy) phenyl) -2- methyl acetone (Darocur 2959) (33.69g,
0.15mol), phthalic anhydride (14.81g, 0.1mol), the anhydrous AlCl of catalyst3(10.67,0.08mol) and 120ml first
Benzole soln is added in the 250ml three-necked flask for being equipped with mechanical stirring and constant pressure funnel, 110 DEG C of stirring 60min.Reaction
After, it is filtered to remove solid impurity, 3 washing, liquid separation removing water phases, revolving removes toluene, and finally vacuum drying removes molten
After agent and water, intermediate product A is obtained；Then by the intermediate product A and triethylamine that are dissolved in 80ml tetrahydrofuran (10.22g,
It 0.1mol) is added in the 250ml three-necked flask for being equipped with mechanical stirring and constant pressure funnel, 18h is stirred at room temperature.It has reacted
Cheng Hou is washed three times with hydrochloric acid or ethyl acetate, solvent is rotated and is removed, is further purified with gel chromatography post separation, finally
Clean product 2 is obtained, and Structural Identification is carried out by NMR spectrum.
1HNMR(400MHz,Acetone-d6)δ(ppm):6.99-7.94(8H,aromatics),3.28-4.62
(10H,-CH2-),4.62(1H,-OH)1.25-1.35(15H,-CH3).
Embodiment 3
The structural formula of compound 3 are as follows:
By 2- hydroxyl -1- (4- (2- hydroxy ethoxy) phenyl) -2- methyl acetone (Darocur 2959) (33.69g,
0.15mol), itaconic anhydride (11.22g, 0.1mol), the anhydrous AlCl of catalyst3(10.67,0.08mol) and 800ml toluene
Solution is added in the 250ml three-necked flask for being equipped with mechanical stirring and constant pressure funnel, 90 DEG C of stirring 60min.Reaction knot
Shu Hou is filtered to remove solid impurity, 3 washing, liquid separation removing water phases, and revolving removes toluene, and finally vacuum drying removes solvent
After water, intermediate product A is obtained；Then by the intermediate product A and triethylamine that are dissolved in 60ml carbon tetrachloride (10.22g,
It 0.1mol) is added in the 250ml three-necked flask for being equipped with mechanical stirring and constant pressure funnel, 16h is stirred at room temperature.It has reacted
Cheng Hou is washed three times with hydrochloric acid or ethyl acetate, solvent is rotated and is removed, is further purified with gel chromatography post separation, finally
Clean product 3 is obtained, and Structural Identification is carried out by NMR spectrum.
1HNMR(400MHz,Acetone-d6)δ(ppm):6.99-7.94(4H,aromatics),3.28-4.52
(10H,-CH2-),4.62(1H,-OH)1.25-1.35(15H,-CH3), 5.56-6.28 (2H ,=CH2).
Embodiment 4
The structural formula of compound 4 are as follows:
By 2- hydroxyl -1- (4- (2- hydroxy ethoxy) phenyl) -2- methyl acetone (Darocur 2959) (33.69g,
0.15mol), 2,3- dimethyl maleic anhydride (12.61g, 0.1mol), the anhydrous AlCl of catalyst3(10.67,0.08mol) and
100ml toluene solution is added in the 250ml three-necked flask for being equipped with mechanical stirring and constant pressure funnel, 90 DEG C of stirrings
60min.After reaction, it is filtered to remove solid impurity, 3 washing, liquid separation removing water phases, revolving removes toluene, last vacuum
After drying and removing solvent and water, intermediate product A is obtained；The intermediate product A and triethylamine being then dissolved in 60ml pyridine
(10.22g, 0.1mol) is added in the 250ml three-necked flask for being equipped with mechanical stirring and constant pressure funnel, is stirred at room temperature
16h.After the reaction was completed, it is washed three times with hydrochloric acid or ethyl acetate, solvent is rotated and is removed, it is further with gel chromatography post separation
Purification, finally obtains clean product 4, and carry out Structural Identification by NMR spectrum.
1HNMR(400MHz,Acetone-d6)δ(ppm):6.99-7.94(4H,aromatics),3.28-4.52
(10H,-CH2), 6.44-7.94 (2H ,-CH=), 4.62 (1H ,-OH) 1.25-2.34 (21H ,-CH3).
Comparison example 5
By product obtained by above-described embodiment 1-4 and 2- hydroxyl -1- (4- (2- hydroxy ethoxy) phenyl) -2- methyl-prop
Ketone (Darocur 2959) causes acrylamide polymerization in aqueous solution, and methyl diethanolamine (MDEA) is aided initiating.Wherein,
The concentration of acrylamide is 2mol/L, and the concentration of each initiator and MDEA are 0.02mol/L, light intensity 50mW/cm2.Propylene
Final conversion ratio of the amide after the initiation of different initiators is shown in Table 1.The result shows that prepared photoinitiator draws in aqueous solution
Send out acrylamide polymerization efficiency it is different degrees of be higher than Darocur 2959, although Darocur 2959 have it is certain water-soluble
Property, but by the way that carboxyl to be introduced into its molecular structure, the form for generating quaternary ammonium salt is being reacted with amine salt, it can further increase
The dissolubility of these initiators in water.
Final conversion ratio of 1 acrylamide of table after the initiation of different initiators
Claims (6)
1. the preparation method of a kind of water-soluble light trigger, it is characterised in that include the following steps:
2- hydroxyl -1- (4- (2- hydroxy ethoxy) phenyl) -2- methyl acetone (Darocur 2959) is added in step 1) in a solvent
And acid anhydrides, it stirs under heating condition；
The anhydrous AlCl of catalyst is added in step 2) in the mixture of step 1)3Reaction 1 hour；
Step 3) after the reaction was completed, is filtered to remove solid impurity, and revolving removes solvent, and finally vacuum drying removes solvent and water
Afterwards, intermediate product A is obtained；
Intermediate product A and triethylamine is added in step 4) in a solvent, reacts 16 hours at room temperature；
Step 5) after the reaction was completed, is washed three times with hydrochloric acid or ethyl acetate, solvent is rotated and is removed, with gel chromatography post separation
Further purification, finally obtains clean product；
The structural formula of the water-soluble light trigger are as follows:
。
2. the preparation method of one kind water-soluble light trigger as described in claim 1, it is characterised in that: the acid anhydrides type
It is more.
3. the preparation method of one kind water-soluble light trigger as described in claim 1, it is characterised in that: the Darocur
The molar ratio of 2959 photoinitiators and acid anhydrides is 1.5:1.
4. the preparation method of one kind water-soluble light trigger as described in claim 1, it is characterised in that: the heating condition
Temperature is 90-110 DEG C.
5. the preparation method of one kind water-soluble light trigger as described in claim 1, it is characterised in that: the intermediate product A
Molar ratio with triethylamine is 1:1.
6. the preparation method of one kind water-soluble light trigger as described in claim 1, it is characterised in that: the solvent is first
One or more of benzene, pyridine, tetrahydrofuran and carbon tetrachloride.
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| CN201710650594.4A CN109384670A (en) | 2017-08-02 | 2017-08-02 | A kind of water-soluble light trigger and preparation method thereof |
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| CN201710650594.4A CN109384670A (en) | 2017-08-02 | 2017-08-02 | A kind of water-soluble light trigger and preparation method thereof |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110105471A (en) * | 2019-06-04 | 2019-08-09 | 连州市祥丰化工有限公司 | Water-soluble light trigger and preparation method thereof |
| CN110684135A (en) * | 2019-10-28 | 2020-01-14 | 南昌航空大学 | Itaconic acid modified photoinitiator and preparation method thereof |
| CN111153800A (en) * | 2020-01-17 | 2020-05-15 | 南昌航空大学 | Rare earth terbium modified α -hydroxyketone photoinitiator and preparation method thereof |
| CN114656592A (en) * | 2020-12-23 | 2022-06-24 | 北京化工大学 | Water-soluble macromolecular photoinitiator and preparation method and application thereof |
| CN114656591A (en) * | 2020-12-23 | 2022-06-24 | 北京化工大学 | Water-soluble macromolecular photoinitiator and preparation method and application thereof |
-
2017
- 2017-08-02 CN CN201710650594.4A patent/CN109384670A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110105471A (en) * | 2019-06-04 | 2019-08-09 | 连州市祥丰化工有限公司 | Water-soluble light trigger and preparation method thereof |
| CN110105471B (en) * | 2019-06-04 | 2021-04-09 | 连州市祥丰化工有限公司 | Water-soluble photoinitiator and preparation method thereof |
| CN110684135A (en) * | 2019-10-28 | 2020-01-14 | 南昌航空大学 | Itaconic acid modified photoinitiator and preparation method thereof |
| CN111153800A (en) * | 2020-01-17 | 2020-05-15 | 南昌航空大学 | Rare earth terbium modified α -hydroxyketone photoinitiator and preparation method thereof |
| CN114656592A (en) * | 2020-12-23 | 2022-06-24 | 北京化工大学 | Water-soluble macromolecular photoinitiator and preparation method and application thereof |
| CN114656591A (en) * | 2020-12-23 | 2022-06-24 | 北京化工大学 | Water-soluble macromolecular photoinitiator and preparation method and application thereof |
| CN114656591B (en) * | 2020-12-23 | 2023-06-13 | 北京化工大学 | Water-soluble macromolecular photoinitiator and preparation method and application thereof |
| CN114656592B (en) * | 2020-12-23 | 2023-06-13 | 北京化工大学 | Water-soluble macromolecular photoinitiator and preparation method and application thereof |
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