CN109400761A - A kind of modified active amine aided initiating synthesis and preparation method - Google Patents
A kind of modified active amine aided initiating synthesis and preparation method Download PDFInfo
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- CN109400761A CN109400761A CN201710695551.8A CN201710695551A CN109400761A CN 109400761 A CN109400761 A CN 109400761A CN 201710695551 A CN201710695551 A CN 201710695551A CN 109400761 A CN109400761 A CN 109400761A
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- Prior art keywords
- aided initiating
- modified active
- active amine
- amine aided
- reaction
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- 230000000977 initiatory effect Effects 0.000 title claims abstract description 28
- 150000001412 amines Chemical class 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 230000015572 biosynthetic process Effects 0.000 title claims description 7
- 238000001308 synthesis method Methods 0.000 title description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 7
- DLYLVPHSKJVGLG-UHFFFAOYSA-N 4-(cyclohexylmethyl)cyclohexane-1,1-diamine Chemical compound C1CC(N)(N)CCC1CC1CCCCC1 DLYLVPHSKJVGLG-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 238000005516 engineering process Methods 0.000 claims description 4
- 239000005457 ice water Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003999 initiator Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 12
- 238000000016 photochemical curing Methods 0.000 abstract description 6
- 150000003512 tertiary amines Chemical class 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 2
- 238000012805 post-processing Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 8
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000005452 bending Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000003141 primary amines Chemical class 0.000 description 4
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 3
- -1 acrylic acid tetrahydrofuran ester Chemical class 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 238000006356 dehydrogenation reaction Methods 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008033 biological extinction Effects 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
- 229920006037 cross link polymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000005357 flat glass Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000000852 hydrogen donor Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/20—Oxygen atoms
-
- 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
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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention belongs to field of light-sensitive high molecular materials.The present invention provides a kind of modified active amine aided initiatings, acrylic double bond is introduced into amine aided initiating by synthetic reaction and forms reactive amines, participate in photocuring reaction, avoid in the past with low molecule tertiary amine smell it is big, photocuring reaction, residual disadvantage easy to migrate cannot be participated in.The present invention provides the preparation methods of this kind of reactive amines aided initiating, and reaction process is simple, and reaction condition is mild, and post-processing is simple and is easy purifying.
Description
Technical field
The invention belongs to field of light-sensitive high molecular materials, a kind of modified active amine aided initiating synthesis and preparation method thereof.
Background technique
Photocuring has been widely used in many important technology fields, especially because the advantage of itself, low
VOC release, is a kind of green technology, is mainly used in rapid curing coating, printing ink and adhesive etc..Photoinitiator
Occupy key player in UV curing system, the energy production reactive species that specific wavelength can be absorbed in they cause whole system
Polymerization.
Aided initiating is the hydrogen donor being used cooperatively with hydrogen-abstraction free radical photo-initiation, light-initiated with excitation state hydrogen-abstraction
Agent effect forms exciplex, and nitrogen-atoms loses an electronics, and N faces the H on a α-C in highly acid, it is easy to lose matter
Son generates the reactive amines alkyl diradical centered on C, causes oligomer and reactive diluent cross-linked polymeric.
Reactive amines are a kind of acrylate with tertiary amine group.They draw as aided initiating with hydrogen-abstraction free radical light
Hair agent is used cooperatively, and can improve photo-curing rate；The influence for reducing oxygen inhibition is conducive to improve surface cure；With polymerizable
Acrylic acid groups, participate in photocuring reaction, avoid in the past with low molecule tertiary amine smell it is big, photocuring reaction cannot be participated in, residual
Stay disadvantage easy to migrate.
Summary of the invention
The technical problem to be solved by the present invention is the migration bring smell of amine aided initiating.The present invention passes through synthesis one
Kind reactive amines aided initiating increases the molecular weight of aided initiating and introduces polymerizable double bond to improve crosslink density, reduces migration.
The present invention solves the technological means that technical problem uses: a kind of modified active amine aided initiating, molecular structure
Are as follows:
Wherein R can be selected from acrylate or acrylamide.
The present invention also provides the preparation method of the initiator, general synthesis technology is shown below:
Specific step is as follows for preparation:
4,4'- diamino-dicyclohexyl methane is added in the reaction vessel, and suitable methanol is added as solvent, Xiang Qi
In be passed through nitrogen, stirred under ice water bath environment.With the acrylate of 4 times of 4,4'- diamino-dicyclohexyl methane moles or
Acrylamide is dissolved in suitable methanol, is slowly added dropwise into reaction vessel.It is anti-after being added dropwise with the rate of about 0.5mL/min
It answers 2h, TLC to detect that the point of 4,4'- diamino-dicyclohexyl methane and acrylate or acrylamide disappears, takes out, decompression is steamed
It evaporates, obtains sample.
Specifically, the solvent be one of methanol, ethyl alcohol, carbon tetrachloride, chloroform, methylene chloride and toluene or
It is several；
Specifically, the whipping temp can be 0-40 DEG C；
It is specifically, described that be stirred at reflux the time can be 0.5-3 hours；
Specifically, 4, the 4'- diamino-dicyclohexyl methane can be with the molar ratio of acrylate or acrylamide
1:4-5。
Compared with the prior art, the advantages of the present invention are as follows:
(1) synthesis step of the invention is simple, and preparation cost is low, and reaction condition is mild, and post-processing is simple.
(2) polymerizable double bond is introduced compared with former amine aided initiating, solidification crosslinking can be participated in, reduce small molecule
Residual and migration.
Specific embodiment
The present invention will be described in detail for the following example, but does not limit the scope of the invention.
Synthetic example 1:
1 structural formula of compound
100mL three-necked flask is sufficiently dry, lead to nitrogen.2.11g 4 is taken, 4'- diamino-dicyclohexyl methane is dissolved in
12.00g methanol is added in three-necked flask.5.64g acryloyl morpholine is taken, 19.81g methanol is dissolved in, constant pressure funnel is added.
The methanol solution of acryloyl morpholine is slowly dropped into three-necked flask under the conditions of ice-water bath, 3-4s mono- drips, and stirs simultaneously.It is added dropwise
After continue to stir 2h, detect that the point of 4,4'- diamino-dicyclohexyl methane and acryloyl morpholine disappears by TLC.Knot
Vacuum distillation removes solvent after beam, obtains product.
Sampling by IR test as can be seen that reaction after 910cm-1Neighbouring C=C bending vibration absorption peak disappears,
1590cm-1Neighbouring primary amine N-H bending vibration absorption peak disappears, 1630cm-1Neighbouring C=C stretching vibration absworption peak disappears,
3300cm-1Two neighbouring primary amine N-H stretching vibration absworption peaks disappear, it was demonstrated that fully reacting.
Synthetic example 2:
2 structural formula of compound
100mL three-necked flask is sufficiently dry, lead to nitrogen.2.11g 4 is taken, 4'- diamino-dicyclohexyl methane is dissolved in
12.00g methanol is added in three-necked flask.6.25g acrylic acid tetrahydrofuran ester is taken, 19.81g methanol is dissolved in, constant pressure drop is added
Liquid funnel.The methanol solution of acrylic acid tetrahydrofuran ester is slowly dropped into three-necked flask under the conditions of ice-water bath, 3-4s mono- drips,
It stirs simultaneously.Continue to stir 2h after being added dropwise, 4,4'- diamino-dicyclohexyl methane and acrylic acid four are detected by TLC
The point of hydrogen furans ester disappears.After vacuum distillation remove solvent, obtain product.
Sampling by IR test as can be seen that reaction after 895cm-1Neighbouring C=C bending vibration absorption peak disappears,
1590cm-1Neighbouring primary amine N-H bending vibration absorption peak disappears, 1635cm-1Neighbouring C=C stretching vibration absworption peak disappears,
3300cm-1Two neighbouring primary amine N-H stretching vibration absworption peaks disappear, it was demonstrated that fully reacting.
Comparative example 3:
1, photosensitive polymer combination is prepared
By product and 4 obtained by examples detailed above 1,2,4'- diamino-dicyclohexyl methane (PACM) is used as aided initiating,
Trimethylolpropane trimethacrylate (TMPTA) is used as matrix resin, and benzophenone (BP) is used as photoinitiator, according to following table
Middle proportional arrangement photosensitive polymer combination.
1 photoresist each group distribution ratio of table
| Embodiment 1 | Embodiment 2 | Comparative example 1 | |
| TMPTA | 100 | 100 | 100 |
| BP | 2 | 2 | 2 |
| PACM | 2 | ||
| Product 1 | 2 | ||
| Product 2 | 2 |
2, pencil hardness test
Above-mentioned composition is protected from light after being uniformly mixed, feeding is applied on polishing iron plate, using bar film, forms film
Thick about 25 μm of film, then uses mercury lamp light source (light intensity 240mJ/cm2) film is exposed, time for exposure 120s.Exposure
After, paint film pencil hardness test, test result is as follows table are carried out according to GB/T 6739-2006 standard.
2 pencil hardness test result of table
| Embodiment 1 | Embodiment 2 | Comparative example 1 | |
| Pencil hardness | 4H | 4H | 3H |
From table 2 it can be seen that compared with aided initiating before modified, the reactive amines aided initiating as described in this patent can be with
Polymerization is participated in, crosslink density is improved, to improve the hardness of paint film.
3, mobility is tested
Above-mentioned composition is protected from light after being uniformly mixed, is injected into homemade 30mm × 5mm × 1mm mold.Sample
It is clamped up and down with sheet glass, illumination 5min, light intensity 30mW/cm in UV solidification case2, completion of cure.Then batten is crushed,
0.1g is respectively taken, is extracted at room temperature 5 days with 10ml acetonitrile.Finally, same amount of extract liquor is taken to carry out UV absorption test.
Relative mobility of the product relative to PACM can be obtained by formula (1) and (2).
C=A/ (ε × b) formula (1)
R=CProduct/CPACM× 100% formula (2)
Wherein C is the concentration (molL of aided initiating in extract liquor-1)；A is absorbance；ε is molar extinction coefficient (L
mol-1·cm-1)；B is sample cell thickness (cm)；CProductFor the concentration of product in extract liquor；CPACMFor in extract liquor PACM it is dense
Degree；R is the relative mobility of reactive amines aided initiating.
Test result is as follows table.
3 mobility test result of table
| Embodiment 1 | Embodiment 2 | Comparative example 1 | |
| Mobility/R | 42 | 36 | 100 |
From table 3 it can be seen that the reactive amines aided initiating as described in this patent participates in compared with aided initiating before modified
Polymerization, is fixed in crosslinked polymer network, to reduce mobility, reduces the toxicity of cured film.
Claims (7)
1. a kind of modified active amine aided initiating, it is characterised in that the molecular structure of this kind of initiator is as follows:
Wherein R can be selected from acrylate or acrylamide.
2. one kind modified active amine aided initiating according to claim 1, it is characterised in that its general synthesis technology is such as
Shown in following formula.
3. one kind modified active amine aided initiating according to claim 2, it is characterised in that the reactive amines aided initiating
Preparation process the following steps are included:
It is added acrylate or acrylamide and 4 in a solvent, 4'- diamino-dicyclohexyl methane, in logical nitrogen, ice-water bath
Under the conditions of stir, monitored by TLC method to fully reacting, revolving.
4. one kind modified active amine aided initiating according to claim 2, it is characterised in that: the solvent is methanol, second
One or more of alcohol, carbon tetrachloride, chloroform, methylene chloride and toluene.
5. one kind modified active amine aided initiating according to claim 2, it is characterised in that: the whipping temp can be
0-40℃。
6. one kind modified active amine aided initiating according to claim 2, it is characterised in that: it is described be stirred at reflux the time can
Think to be 0.5-3 hours.
7. one kind modified active amine aided initiating according to claim 2, it is characterised in that: 4, the 4'- diamino two
The molar ratio of cyclohexyl-methane and acrylate or acrylamide can be 1:4-5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710695551.8A CN109400761A (en) | 2017-08-15 | 2017-08-15 | A kind of modified active amine aided initiating synthesis and preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710695551.8A CN109400761A (en) | 2017-08-15 | 2017-08-15 | A kind of modified active amine aided initiating synthesis and preparation method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109400761A true CN109400761A (en) | 2019-03-01 |
Family
ID=65454056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710695551.8A Pending CN109400761A (en) | 2017-08-15 | 2017-08-15 | A kind of modified active amine aided initiating synthesis and preparation method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109400761A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112830982A (en) * | 2020-12-31 | 2021-05-25 | 天津久日新材料股份有限公司 | Amine co-initiator and preparation method and application thereof |
| CN112852284A (en) * | 2021-02-25 | 2021-05-28 | 管善月 | Organosilicon modified urethane acrylate photocureable coating and preparation method thereof |
-
2017
- 2017-08-15 CN CN201710695551.8A patent/CN109400761A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112830982A (en) * | 2020-12-31 | 2021-05-25 | 天津久日新材料股份有限公司 | Amine co-initiator and preparation method and application thereof |
| CN112830982B (en) * | 2020-12-31 | 2023-05-12 | 天津久日新材料股份有限公司 | Amine assisted initiator and preparation method and application thereof |
| CN112852284A (en) * | 2021-02-25 | 2021-05-28 | 管善月 | Organosilicon modified urethane acrylate photocureable coating and preparation method thereof |
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