CN109776345A - A kind of photo-curing monomer and preparation method thereof containing active amine structure - Google Patents
A kind of photo-curing monomer and preparation method thereof containing active amine structure Download PDFInfo
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- CN109776345A CN109776345A CN201910062269.5A CN201910062269A CN109776345A CN 109776345 A CN109776345 A CN 109776345A CN 201910062269 A CN201910062269 A CN 201910062269A CN 109776345 A CN109776345 A CN 109776345A
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- containing active
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- 239000000178 monomer Substances 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 238000000016 photochemical curing Methods 0.000 title abstract description 14
- 125000003277 amino group Chemical group 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 55
- 150000001412 amines Chemical group 0.000 claims abstract description 30
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 28
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 21
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000000126 substance Substances 0.000 claims abstract description 13
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- 239000003112 inhibitor Substances 0.000 claims abstract description 6
- 150000003335 secondary amines Chemical class 0.000 claims description 10
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims description 9
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 claims description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 5
- 229940043237 diethanolamine Drugs 0.000 claims description 5
- 239000012752 auxiliary agent Substances 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 3
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 claims description 3
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 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
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- -1 small molecule compound Chemical class 0.000 abstract description 10
- 238000000576 coating method Methods 0.000 abstract description 7
- 239000011248 coating agent Substances 0.000 abstract description 6
- 239000003999 initiator Substances 0.000 abstract description 5
- 238000000034 method Methods 0.000 abstract description 5
- 230000008569 process Effects 0.000 abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 abstract description 3
- 239000001301 oxygen Substances 0.000 abstract description 3
- 230000002411 adverse Effects 0.000 abstract description 2
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 230000002401 inhibitory effect Effects 0.000 abstract description 2
- 230000005012 migration Effects 0.000 abstract description 2
- 238000013508 migration Methods 0.000 abstract description 2
- 239000002861 polymer material Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000002253 acid Substances 0.000 description 14
- 238000010792 warming Methods 0.000 description 14
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000012855 volatile organic compound Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 238000006356 dehydrogenation reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Abstract
The problem of present invention discloses a kind of photo polymerization monomer containing active amine structure, is related to synthesis of polymer material field, is migrated easily from solidify coating based on initiator in existing photocuring system and propose, with following chemical structural formula:
Description
Technical field
The present invention relates to synthesis of polymer material fields, and in particular to a kind of photo-curing monomer containing active amine structure and
Preparation method.
Background technique
The volatile organic compounds (VOC) being emitted into atmosphere can pass through the chemical and photochemical of complexity with gases such as NOx
Act on forming ozone, photochemical fog etc..In recent years, the VOC emission amount in China is continuously increased, this seriously endangers the strong of the mankind
Health and ecological environment security.In order to promote energy conservation and environmental protection, develop low VOC coatings.Photocureable coating is a kind of with photocuring activity
Diluent is the coating system of solvent, participates in curing reaction using polymerizable monomer to avoid VOC emission.
Photopolymer System is mainly grouped as by following three kinds of groups: (1) oligomer (prepolymer): one kind containing photocuring reaction
The photoresist of group (such as C=C double bond, epoxy group), is the basic resin of photocurable formulation, can determine cured article
Basic performance；(2) monomer (reactive diluent): one kind for adjust photocuring system viscosity have carbon carbon unsaturated double-bond
Compound, the most frequently used is the monomer of the groups such as (methyl) acryloxy containing vinyl, allyl；(3) photoinitiator:
One kind generates the compound that can trigger the reactive species of monomer polymerization after the light for absorbing certain wavelength.
For free mafic Photopolymer System, radical photoinitiator can be divided into cracking type free radical photo-initiation
(I type of Norrish) and hydrogen-abstraction free radical photo-initiation (II type of Norrish).II type photoinitiator of Norrish is absorbing luminous energy
Afterwards, from ground state transition to excitation state, meanwhile, bimolecular effect occurs with aided initiating, is turned by hydrogen abstraction reaction or electronics/proton
The mode of shifting forms living radical.
Initiator is easily migrated from solidify coating in existing photocuring system, causes the dirt with the sample of coating layer touch
Dye, and the problem of oxygen inhibition easily occurs in Light Curing, influence the surface property of coating after photocuring.
Summary of the invention
The problem to be solved by the present invention is that initiator migrates analysis easily from solidify coating in existing photocuring system
Out.
The present invention adopts the following technical solutions solves above-mentioned technical problem:
A kind of photo polymerization monomer containing active amine structure, with following chemical structural formula:
Wherein R1For one of alkoxy, alkyl, benzyl, heterocycle.
Preferably, the photo polymerization monomer containing active amine structure, chemical structural formula are one in following structural formula
Kind:
The present invention also provides a kind of preparation methods of photo polymerization monomer containing active amine structure, comprising the following steps:
(1) using glycidyl methacrylate as major ingredient, auxiliary agent is added, mixing is added acrylic acid, obtains reactant
System；
(2) secondary amine is added into the reaction system of step (1), is reacted；
(3) after reacting, cooling is dried to obtain product.
Preferably, the auxiliary agent in the step (1) is catalyst and polymerization inhibitor.
Preferably, the catalyst in the step (1) is tetramethyl ammonium chloride, in tetrabutylammonium bromide, triphenyl phosphorus
It is one or two kinds of.
Preferably, the additional amount of the catalyst is the 1- of glycidyl methacrylate and acrylic acid gross mass
3wt%.
Preferably, the polymerization inhibitor in the step (1) is hydroxyanisol.
Preferably, in the step (1) polymerization inhibitor additional amount be reaction system gross mass 0.1-0.5wt%.
Preferably, the reaction temperature in the step (1) is 90-110 DEG C, reaction time 4-5h.
Preferably, secondary amine is added dropwise into the reaction system of step (1), the rate of addition of the secondary amine is 10-30g/min.
Preferably, the secondary amine is one of diethanol amine, diethylamide, N- methylbenzylamine, morpholine.
Preferably, the molar ratio of the secondary amine and acrylic acid is 1:1.
The beneficial effects of the present invention are:
(1) by acrylic acid and glycidyl methacrylate ring-opening reaction, acrylate and methacrylic acid are utilized
The difference of ester double bond reactivity is added reactive amines and reacts with acrylic double bond, preparation contains by Michael addition reaction
There are the photo-curing monomer of active amine structure the active reactive amines of photocuring may participate in solidification process, molecular structure after solidification
It is connected in converging network, can avoid the migration of small molecule compound, prevent from adversely affecting photocuring system；
(2) amine structure is introduced into polymerization system, can obtain certain resistance to the oxygen inhibiting polymerization performance, to obtain preferable table
Face curing performance makes the initiator of cured film have low toxicity at the same time as the aided initiating of hydrogen-abstraction initiator system, low to move
Shifting property；
(3) reaction process is simple, and process conditions are easily controllable.
Specific embodiment
The present invention is described in further details below with reference to embodiment.
Test material and reagent as used in the following examples etc., unless otherwise specified, commercially obtain.
Embodiment 1
The reaction equation of photo polymerization monomer preparation process containing reactive amines is as follows:
Embodiment 2
A kind of preparation method of the photo polymerization monomer containing active amine structure, comprising the following steps:
(1) glycidyl methacrylate 64g is weighed, tetramethyl ammonium chloride 3.0g, hydroxyanisol 0.1g is added, in
In three-necked flask, stirring is warming up to 90 DEG C, and acrylic acid 37.8g is added dropwise into reaction system using constant pressure funnel, drips
Acid value is tested after Bi Hou, the reaction was continued 4h, when acid value is less than 10mg KOH/g, stops reaction；
(2) after cooling, in ice bath, diethanol amine 55g is added dropwise into reaction system, after being added dropwise, is warming up to 60 DEG C,
The reaction was continued 2h；
(3) after reaction, it is cooled to room temperature, product is washed with deionized 2-3 times, then is water-soluble with 1wt%NaOH
Liquid washs 2-3 times, is finally washed with deionized to neutrality, is transferred in beaker, suitable anhydrous sodium sulfate is added, dry
For 24 hours, it filters to get the propenoic acid ester photocureable monomer containing reactive amines is arrived.
The chemical structural formula of the monomer is as follows:
Embodiment 3
(1) glycidyl methacrylate 64g is weighed, tetrabutylammonium bromide 1.2g, hydroxyanisol 0.5g is added, in
In three-necked flask, stirring is warming up to 110 DEG C, and acrylic acid 43.2g is added dropwise into reaction system using constant pressure funnel, drips
Acid value is tested after Bi Hou, the reaction was continued 4h, when acid value is less than 10mgKOH/g, stops reaction；
(2) under condition of ice bath, diethanol amine 63g is added dropwise into reaction system, after being added dropwise, is warming up to 80 DEG C, after
Continuous reaction 2h；
(3) after reaction, it is cooled to room temperature, product is washed with deionized 2-3 times, then is water-soluble with 1wt%NaOH
Liquid washs 2-3 times, is finally washed with deionized to neutrality, is transferred in beaker, suitable anhydrous sodium sulfate is added, dry
For 24 hours, it filters to get the propenoic acid ester photocureable monomer containing reactive amines is arrived.
The chemical structural formula of the monomer is as follows:
Embodiment 4
(1) glycidyl methacrylate 64g is weighed, tetramethyl ammonium chloride 2.5g, hydroxyanisol 0.3g is added, in
In three-necked flask, stirring is warming up to 100 DEG C, and acrylic acid 39.6g is added dropwise into reaction system using constant pressure funnel, drips
Acid value is tested after Bi Hou, the reaction was continued 4h, when acid value is less than 10mg KOH/g, stops reaction；
(2) under condition of ice bath, diethylamide 39g is added dropwise into reaction system, after being added dropwise, is warming up to 60 DEG C, after
Continuous reaction 2h；
(3) after reaction, it is cooled to room temperature, product is washed with deionized 2-3 times, then is water-soluble with 1wt%NaOH
Liquid washs 2-3 times, is finally washed with deionized to neutrality, is transferred in beaker, suitable anhydrous sodium sulfate is added, dry
For 24 hours, it filters to get the propenoic acid ester photocureable monomer containing reactive amines is arrived.
The chemical structural formula of the monomer is as follows:
Embodiment 5
(1) glycidyl methacrylate 64g is weighed, triphenyl phosphorus 1.5g, hydroxyanisol 0.5g, Yu Sankou is added
In flask, stirring is warming up to 110 DEG C, and acrylic acid 37.8g is added dropwise into reaction system using constant pressure funnel, is added dropwise
Afterwards, acid value is tested after the reaction was continued 4h, when acid value is less than 10mgKOH/g, stops reaction；
(2) under condition of ice bath, diethanol amine 25.4g is added dropwise into reaction system, after being added dropwise, is warming up to 70 DEG C,
The reaction was continued 2h；
(3) after reaction, it is cooled to room temperature, product is washed with deionized 2-3 times, then is water-soluble with 1wt%NaOH
Liquid washs 2-3 times, is finally washed with deionized to neutrality, is transferred in beaker, suitable anhydrous sodium sulfate is added, dry
For 24 hours, it filters to get the propenoic acid ester photocureable monomer containing reactive amines is arrived.
The chemical structural formula of the monomer is as follows:
Embodiment 6
(1) glycidyl methacrylate 64g is weighed, tetramethyl ammonium chloride 2.0g, hydroxyanisol 0.3g is added, in
In three-necked flask, stirring is warming up to 100 DEG C, and acrylic acid 37.8g is added dropwise into reaction system using constant pressure funnel, drips
After Bi Hou, the reaction was continued 4h, acid value is tested, when acid value is less than 10mgKOH/g, stops reaction；
(2) under condition of ice bath, morpholine 45.6g is added dropwise into reaction system, after being added dropwise, is warming up to 70 DEG C, continues
React 2h；
(3) after reaction, it is washed with deionized 2-3 times in separatory funnel, then washs 2- with 1wt%NaOH aqueous solution
It 3 times, is finally washed with deionized to neutrality, is transferred in beaker, suitable anhydrous sodium sulfate is added, it is dry to filter for 24 hours,
Obtain the propenoic acid ester photocureable monomer containing reactive amines.
The chemical structural formula of the monomer is as follows:
Embodiment 7
(1) glycidyl methacrylate 64g is weighed, tetramethyl ammonium chloride 3.0g, hydroxyanisol 0.1g is added, in
In three-necked flask, stirring is warming up to 90 DEG C, and acrylic acid 39.6g is added dropwise into reaction system using constant pressure funnel, drips
Acid value is tested after Bi Hou, the reaction was continued 4h, when acid value is less than 10mgKOH/g, stops reaction；
(2) under condition of ice bath, diethylamine 39g is added dropwise into reaction system, after being added dropwise, is warming up to 70 DEG C, continues anti-
Answer 2h；
(3) after reaction, it is cooled to room temperature, product is washed with deionized 2-3 times, then with 1wt%NaOH aqueous solution
Washing 2-3 times, is finally washed with deionized to neutrality, is transferred in beaker, and suitable anhydrous sodium sulfate is added, and dries for 24 hours,
It filters to get the propenoic acid ester photocureable monomer containing reactive amines is arrived.
The chemical structural formula of the monomer is as follows:
Embodiment 8
(1) glycidyl methacrylate 64g is weighed, tetramethyl ammonium chloride 3.0g, hydroxyanisol 0.1g is added, in
In three-necked flask, stirring is warming up to 90 DEG C, and acrylic acid 39.6g is added dropwise into reaction system using constant pressure funnel, drips
Acid value is tested after Bi Hou, the reaction was continued 4h, when acid value is less than 10mg KOH/g, stops reaction；
(2) under condition of ice bath, N- methylbenzylamine 39g is added dropwise into reaction system, after being added dropwise, is warming up to 70 DEG C, after
Continuous reaction 2h；
(3) after reaction, it is cooled to room temperature, product is washed with deionized 2-3 times, then with 1wt%NaOH aqueous solution
Washing 2-3 times, is finally washed with deionized to neutrality, is transferred in beaker, and suitable anhydrous sodium sulfate is added, and dries for 24 hours,
It filters to get the propenoic acid ester photocureable monomer containing reactive amines is arrived.
The chemical structural formula of the monomer is as follows:
The above is only the preferred embodiment of the present invention, protection scope of the present invention is not limited merely to above-described embodiment,
It is within the scope of the invention with present inventive concept without the various process programs of substantial differences.
Claims (10)
1. a kind of photo polymerization monomer containing active amine structure, it is characterised in that: have following chemical structural formula:
Wherein R1For one of alkoxy, alkyl, benzyl, heterocycle.
2. the photo polymerization monomer according to claim 1 containing active amine structure, it is characterised in that: its chemical structural formula is
One of following structural formula:
3. a kind of preparation method for preparing the photo polymerization monomer as described in claim 1 containing active amine structure, feature exist
In: the following steps are included:
(1) using glycidyl methacrylate as major ingredient, auxiliary agent is added, mixing is added acrylic acid, obtains reaction system；
(2) secondary amine is added into the reaction system of step (1), is reacted；
(3) after reacting, cooling is dried to obtain product.
4. the preparation method of the photo polymerization monomer according to claim 3 containing active amine structure, it is characterised in that: described
Auxiliary agent in step (1) is catalyst and polymerization inhibitor.
5. the preparation method of the photo polymerization monomer according to claim 4 containing active amine structure, it is characterised in that: described
Catalyst in step (1) is one or both of tetramethyl ammonium chloride, tetrabutylammonium bromide, triphenyl phosphorus.
6. the preparation method of the photo polymerization monomer according to claim 4 containing active amine structure, it is characterised in that: described
Polymerization inhibitor in step (1) is hydroxyanisol.
7. the preparation method of the photo polymerization monomer according to claim 3 containing active amine structure, it is characterised in that: described
Reaction temperature in step (1) is 90-110 DEG C, reaction time 4-5h.
8. the preparation method of the photo polymerization monomer according to claim 3 containing active amine structure, it is characterised in that: Xiang Bu
Suddenly secondary amine is added dropwise in the reaction system of (1), the rate of addition of the secondary amine is 10-30g/min.
9. the preparation method of the photo polymerization monomer according to claim 3 containing active amine structure, it is characterised in that: described
Secondary amine is one of diethanol amine, diethylamide, N- methylbenzylamine, morpholine.
10. the preparation method of the photo polymerization monomer according to claim 3 containing active amine structure, it is characterised in that: institute
The molar ratio for stating secondary amine and acrylic acid is 1:1.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| CN114292183A (en) * | 2021-12-29 | 2022-04-08 | 徐州博康信息化学品有限公司 | Preparation method of photoresist resin monomer containing hydroxyl structure |
| CN114672127A (en) * | 2021-12-28 | 2022-06-28 | 深圳市纵维立方科技有限公司 | Resin composite material and method for producing same |
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| CN103958460A (en) * | 2011-10-05 | 2014-07-30 | 阿克马法国公司 | Polyhydroxyl - substituted amino compounds, polymers containing, and their use |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103958460A (en) * | 2011-10-05 | 2014-07-30 | 阿克马法国公司 | Polyhydroxyl - substituted amino compounds, polymers containing, and their use |
Non-Patent Citations (2)
| Title |
|---|
| G. Q. WU等: "Synthesis and Photopolymerization of Ethylene Glycol 3-Morpholine-propionate Methacrylate for Potential Dental Composite Application", 《JOURNAL OF APPLIED POLYMER SCIENCE》 * |
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Cited By (4)
| 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 |
| CN114672127A (en) * | 2021-12-28 | 2022-06-28 | 深圳市纵维立方科技有限公司 | Resin composite material and method for producing same |
| CN114292183A (en) * | 2021-12-29 | 2022-04-08 | 徐州博康信息化学品有限公司 | Preparation method of photoresist resin monomer containing hydroxyl structure |
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