CN113233967A - Photoinitiator cyclohexanedione-cyclic diene diketone and synthesis method thereof - Google Patents
Photoinitiator cyclohexanedione-cyclic diene diketone and synthesis method thereof Download PDFInfo
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- CN113233967A CN113233967A CN202110497367.9A CN202110497367A CN113233967A CN 113233967 A CN113233967 A CN 113233967A CN 202110497367 A CN202110497367 A CN 202110497367A CN 113233967 A CN113233967 A CN 113233967A
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- 238000001308 synthesis method Methods 0.000 title abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000012043 crude product Substances 0.000 claims abstract description 11
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000007787 solid Substances 0.000 claims abstract description 11
- 150000001263 acyl chlorides Chemical class 0.000 claims abstract description 7
- 239000003513 alkali Substances 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 239000003054 catalyst Substances 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 230000002194 synthesizing effect Effects 0.000 claims description 7
- 150000001993 dienes Chemical class 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- BHTWZQKERRCPRZ-RYRKJORJSA-N Estra-4,9-diene-3,17-dione Chemical compound C1CC(=O)C=C2CC[C@@H]([C@H]3[C@@](C)(C(CC3)=O)CC3)C3=C21 BHTWZQKERRCPRZ-RYRKJORJSA-N 0.000 claims 5
- 230000000977 initiatory effect Effects 0.000 abstract description 4
- 238000004383 yellowing Methods 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 231100000956 nontoxicity Toxicity 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 8
- 238000001723 curing Methods 0.000 description 7
- 238000000016 photochemical curing Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- -1 printing Substances 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/683—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings having unsaturation outside the aromatic rings
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/30—Ortho- or ortho- and peri-condensed systems containing three rings containing seven-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/36—Ortho- or ortho- and peri-condensed systems containing three rings containing eight-membered rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
Abstract
The invention discloses a photoinitiator cyclohexanedione and cyclic diene diketone and a synthesis method thereof, which comprises the following steps: the method comprises the following steps of (1): 0.25 of the intermediate is added into methanol, stirred at a constant speed for 10min, added with an alkali solution catalyst, protected by being shaded and introduced with nitrogen, reacted for 3 to 12 hours at a temperature of between 20 and 100 ℃ to obtain a light yellow solid, then recrystallized by ethanol to obtain an intermediate a, then the prepared intermediate a and acyl chloride are added into a reaction kettle according to a molar ratio of 1: 2, stirred at a constant speed and reacted for 4 hours to obtain a crude product, and then recrystallized to obtain a photoinitiator based on cyclohexanedione and cyclodiene; the photoinitiator has the advantages of simple synthesis, high visible light utilization rate, no toxicity, no odor, no yellowing and the like, has good initiation efficiency under an LED light source, can be used under an LED lamp light source, and has a wide application range.
Description
Technical Field
The invention belongs to the technical field of organic chemistry, and particularly relates to a photoinitiator cyclohexanedione and cyclic diene diketone and a synthesis method thereof.
Background
Photo-curing refers to a process in which a photoinitiator causes cross-linking polymerization reaction of oligomers under the irradiation of ultraviolet light or visible light to form a solid product. The photocuring reaction has the characteristics of high curing speed, energy conservation, environmental protection, low curing temperature, strong applicability and strong controllability; in addition, the polymer obtained by the photocuring reaction has high crosslinking density, good mechanical property and thermal stability and strong solvent resistance. Photopolymerization technology is widely applied in the fields of coatings, adhesives, printing, biological materials, microelectronics and the like.
Photopolymerisable systems generally comprise the following main three components: oligomers, monomers (also known as reactive diluents), and photoinitiators. Photoinitiators are a key component in photocuring systems. The photoinitiator should have the following characteristics: (1) the price is low, and the synthesis is easy; (2) the stability is good, and the storage is easy; (3) no toxicity and odor; (4) the absorption spectrum is matched with the emission band of the radiation light source, and the molar extinction coefficient is high; (5) higher intersystem crossing efficiency and initiation efficiency are required; (6) has good solubility in prepolymer. Photoinitiators mainly affect the curing speed, yellowing tendency and cost of the photocuring system.
At present, alpha-hydroxy ketones and alpha-amino ketones are the most widely used photoinitiators. These photoinitiators, after photocleavage, generate small molecular fragments, generate unpleasant odours and are poorly resistant to yellowing, limiting many fields of application.
Conventional photoinitiators, such as benzophenone, are generally colorless or yellowish crystals with an absorption maximum of about 340nm, no absorption in the visible region, matching the emission wavelength of mercury medium-pressure lamps, which are frequently initiated using mercury medium-pressure lamps. With the emergence of environmentally friendly and energy-saving LED lamps, there is an increasing interest in developing photoinitiators with good initiation efficiency under LED light sources. Therefore, the photoinitiator which can be used for the light source initiation of the LED lamp and can not cause yellowing phenomenon of the product after photocuring is developed, and the requirement of the prior photocuring field is met.
Disclosure of Invention
In order to overcome the technical problems, the invention provides a photoinitiator cyclohexanedione and cyclic diene diketone and a synthesis method thereof.
The purpose of the invention can be realized by the following technical scheme:
a photoinitiator cyclohexanedione-cyclic diene diketone has a structure shown as the following general formula (I):
wherein n is 0 to 8; r1, R2, R3 and R4 independently represent H or C1-C12The heterocyclic group of (1) is a linear or branched alkyl group, an aryl group, an alkylaryl group, a furan, a thiophene, or the like.
Further, n is 0, and R1, R2, R3, and R4 independently represent H, methyl, ethyl, or phenyl.
Further, n ═ 1, R1, R2, R3, and R4 independently represent H, methyl, ethyl, and phenyl.
Further, n ═ 2, R1, R2, R3, and R4 independently represent H, methyl, ethyl, and phenyl.
A method for synthesizing a photoinitiator cyclohexanedione-cyclic diene diketone comprises the following steps:
the method comprises the following steps of (1): 0.25 of the intermediate is added into methanol, the mixture is stirred at a constant speed for 10min, then an alkali solution catalyst is added, the mixture is protected by being shaded and introduced with nitrogen, the mixture reacts for 3 to 12 hours at the temperature of 20 to 100 ℃ to obtain a light yellow solid, then the light yellow solid is recrystallized by ethanol to obtain an intermediate a, the prepared intermediate a and acyl chloride are added into a reaction kettle according to the molar ratio of 1: 2, the mixture is stirred at a constant speed and reacted for 4 hours to obtain a crude product, and then the crude product is recrystallized to obtain the photoinitiator based on cyclohexanedione-ring diene.
The reaction process is as follows:
further, the alkali solution is any one of a sodium hydroxide solution with a mass fraction of 10% and a potassium hydroxide solution with a mass fraction of 10%.
Further, the amount of the alkali solution is 10% by weight of cyclohexanedione.
The invention has the beneficial effects that:
the invention relates to a photoinitiator cyclohexanedione-cyclic diene diketone, which is prepared by mixing cyclohexanedione and aldehyde compounds according to the molar ratio of 1: 0.25 of the intermediate a is added into methanol for reaction to prepare an intermediate a, and then the intermediate a reacts with acyl chloride to generate the cyclohexanedione and cyclodienedione photoinitiator.
Drawings
In order to facilitate understanding for those skilled in the art, the present invention will be further described with reference to the accompanying drawings.
FIG. 1 is a structure of formula (I);
FIG. 2 is a structure of general formula (II);
FIG. 3 is a structure of formula (II);
FIG. 4 shows the structure of general formula (III).
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example one
A method for synthesizing a photoinitiator cyclohexanedione-cyclic diene diketone comprises the following steps:
the method comprises the following steps of (1): 0.25 of the intermediate is added into methanol, the mixture is stirred at a constant speed for 10min, then sodium hydroxide aqueous solution with the mass fraction of 10% is added, the mixture is protected by nitrogen in a dark place, the mixture reacts for 3 hours at the temperature of 20 ℃ to obtain light yellow solid, then the light yellow solid is recrystallized by ethanol to obtain an intermediate a, the prepared intermediate a and acyl chloride are added into a reaction kettle according to the molar ratio of 1: 2, the mixture is stirred at a constant speed and reacts for 4 hours to obtain a crude product, and then the crude product is recrystallized to obtain the photoinitiator based on cyclohexanedione-ring diene.
The amount of sodium hydroxide solution used was 10% by weight of cyclohexanedione.
When n is 0, R1, R2, R3 and R4 independently represent H, methyl, ethyl and phenyl, the photoinitiator has a structure shown in the following general formula (II), and the reaction process is shown as follows:
a cyclohexanedione-ring diene-based photoinitiator has a structure shown as the following general formula (II):
example two
A method for synthesizing a photoinitiator cyclohexanedione-cyclic diene diketone comprises the following steps:
the method comprises the following steps of (1): 0.25 of the intermediate is added into methanol, the mixture is stirred at a constant speed for 10min, then sodium hydroxide aqueous solution with the mass fraction of 10% is added, the mixture is protected by nitrogen in a dark place, the mixture reacts for 5 hours at the temperature of 50 ℃ to obtain light yellow solid, then the light yellow solid is recrystallized by ethanol to obtain an intermediate a, the prepared intermediate a and acyl chloride are added into a reaction kettle according to the molar ratio of 1: 2, the mixture is stirred at a constant speed and reacts for 4 hours to obtain a crude product, and then the crude product is recrystallized to obtain the photoinitiator based on cyclohexanedione-ring diene.
The amount of sodium hydroxide solution used was 10% by weight of cyclohexanedione.
When n is 1, R1, R2, R3 and R4 independently represent H, methyl, ethyl and phenyl, the photoinitiator has a structure shown in the following general formula (III), and the reaction process is shown as follows:
a cyclohexanedione-cyclic diene-based photoinitiator has a structure shown in the following general formula (III):
EXAMPLE III
A method for synthesizing a photoinitiator cyclohexanedione-cyclic diene diketone comprises the following steps:
the method comprises the following steps of (1): 0.25 of the intermediate is added into methanol, the mixture is stirred at a constant speed for 10min, then sodium hydroxide aqueous solution with the mass fraction of 10% is added, the mixture is protected by nitrogen in a dark place, the mixture reacts for 12 hours at 100 ℃ to obtain light yellow solid, then the light yellow solid is recrystallized by ethanol to obtain an intermediate a, the prepared intermediate a and acyl chloride are added into a reaction kettle according to the molar ratio of 1: 2, the mixture is stirred at a constant speed and reacts for 4 hours to obtain a crude product, and then the crude product is recrystallized to obtain the photoinitiator based on cyclohexanedione-cyclodiene.
The amount of sodium hydroxide solution used was 10% by weight of cyclohexanedione.
When n is 1, R1, R2, R3 and R4 independently represent H, methyl, ethyl and phenyl, the photoinitiator has a structure shown in the following general formula (IIII), and the reaction process is shown as follows:
a cyclohexanedione-cyclic diene-based photoinitiator has a structure represented by the following general formula (IIII):
comparative example 1
This comparative example is a commercial Irgacure TPO BASF Pasteff TPO photoinitiator.
The coating layers obtained by compounding examples 1 to 3 and comparative example 1 under the conditions shown in Table 1 below and then exposing them under the exposure conditions shown in Table 2 were tested for their properties, and the results are shown in Table 3 below:
TABLE 1
TABLE 2
TABLE 3
As can be seen from the above table, examples 1 to 3 formed the coating as the curing agent with a hardness test of 7 to 8H and a curing rate of 93 to 95%, and comparative example 1 formed the coating as the curing agent with a hardness test of 5H and a curing efficiency of 86%.
In the description herein, references to the description of "one embodiment," "an example," "a specific example" or the like are intended to mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the invention. In this specification, the schematic representations of the terms used above do not necessarily refer to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.
The foregoing is illustrative and explanatory only and is not intended to be exhaustive or to limit the invention to the precise embodiments described, and various modifications, additions, and substitutions may be made by those skilled in the art without departing from the scope of the invention or exceeding the scope of the claims.
Claims (7)
1. A photoinitiator cyclohexanedione-cyclic diene diketone is characterized by having a structure shown in the following general formula (I):
wherein n is 0 to 8; r1, R2, R3 and R4 independently represent H or C1-C12The heterocyclic group of (1) is a linear or branched alkyl group, an aryl group, an alkylaryl group, a furan, a thiophene, or the like.
2. A photoinitiator cyclohexanedione-cyclic dienedione according to claim 1, wherein n is 0, and R1, R2, R3 and R4 independently represent H, methyl, ethyl or phenyl.
3. A photoinitiator cyclohexanedione-cyclic dienedione according to claim 1, wherein n-1, R1, R2, R3, R4 independently represent H, methyl, ethyl, phenyl.
4. A photoinitiator cyclohexanedione-cyclic dienedione according to claim 1, wherein n is 2, and R1, R2, R3 and R4 independently represent H, methyl, ethyl or phenyl.
5. The method for synthesizing the photoinitiator cyclohexanedione-cyclic diene diketone according to claim 1, which is characterized by comprising the following steps:
the method comprises the following steps of (1): 0.25 of the intermediate is added into methanol, the mixture is stirred at a constant speed for 10min, then an alkali solution catalyst is added, the mixture is protected by being shaded and introduced with nitrogen, the mixture reacts for 3 to 12 hours at the temperature of 20 to 100 ℃ to obtain a light yellow solid, then the light yellow solid is recrystallized by ethanol to obtain an intermediate a, the prepared intermediate a and acyl chloride are added into a reaction kettle according to the molar ratio of 1: 2, the mixture is stirred at a constant speed and reacted for 4 hours to obtain a crude product, and then the crude product is recrystallized to obtain the photoinitiator based on cyclohexanedione-ring diene.
6. The method for synthesizing cyclohexanedione-cyclic diene dione as a photoinitiator according to claim 5, wherein the alkali solution is any one of a sodium hydroxide solution with a mass fraction of 10% and a potassium hydroxide solution with a mass fraction of 10%.
7. The method for synthesizing cyclohexanedione-cyclic diene dione as a photoinitiator in claim 5, wherein the alkali solution is used in an amount of 10% by weight of the cyclohexanedione.
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