WO2023165522A1 - Dérivé de benzophénone, son procédé de préparation et son utilisation - Google Patents

Dérivé de benzophénone, son procédé de préparation et son utilisation Download PDF

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WO2023165522A1
WO2023165522A1 PCT/CN2023/079040 CN2023079040W WO2023165522A1 WO 2023165522 A1 WO2023165522 A1 WO 2023165522A1 CN 2023079040 W CN2023079040 W CN 2023079040W WO 2023165522 A1 WO2023165522 A1 WO 2023165522A1
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alkyl
unsubstituted
optionally substituted
photocurable composition
formula
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PCT/CN2023/079040
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English (en)
Chinese (zh)
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赵文超
麻忠利
王永林
邵俊峰
王辰龙
胡伟静
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艾坚蒙(安庆)科技发展有限公司
北京英力科技发展有限公司
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Publication of WO2023165522A1 publication Critical patent/WO2023165522A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • 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

Definitions

  • the present application relates to the field of photocuring technology, and relates to a benzophenone derivative, a preparation method and an application thereof.
  • N,N,N,N-tetraethyl-4,4'-diaminobenzophenone referred to as EMK
  • EMK N,N,N,N-tetraethyl-4,4'-diaminobenzophenone
  • EMK is a commonly used high-efficiency co-photoinitiator, which is very useful in inks, especially UV-LED curing inks. important.
  • patent documents such as CN107686450A, CN112707830A, DE2226039A1 and DE44077C the synthesis method of the compound is reported.
  • EP1078598A1, US2010081071A1, CN105974736A, CN104749882A, CN104710843A, etc. EMK is used as auxiliary photoinitiator and hydrogen abstraction type photoinitiator in various compositions to play the role of photopolymerization.
  • EMK is used as auxiliary photoinitiator and hydrogen abstraction type photoinitiator in various compositions to play the role of photopolymerization.
  • its disadvantage is that its molecular weight is small and has certain toxicity, and it is easy to migrate out of the cured material, which affects the stability and safety of the product properties.
  • the technical problem to be solved in this application is to overcome the defect of high migration of photoinitiator or co-photoinitiator in the prior art, so as to provide a benzophenone derivative, a preparation method and its use.
  • a kind of benzophenone derivative has the structure shown in formula (1):
  • n 1 and n 2 are each independently an integer of 0 to 10 (for example, 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10), but not 0 at the same time;
  • R O is optionally substituted C1-C12 alkyl
  • substituted means that any one or more hydrogen atoms on a specified atom are replaced by substituents, so long as the compound after substitution is stable.
  • optionally substituted means that it may or may not be substituted, and unless otherwise specified, the type and number of substituents may be arbitrary on an achievable basis.
  • the alkyl group may be a straight-chain alkyl group or a branched-chain alkyl group.
  • n 1 and n 2 are each independently an integer of 1-6. Further optionally, n 1 and n 2 are each independently an integer of 0-6, and the value of n 1 +n 2 is an integer of 1-6.
  • R 0 is an optionally substituted C1-C12 alkyl group.
  • alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, 2-methyl-1-propyl, 2-methyl-2-propyl, 2-methyl-1- Butyl, 3-methyl-1-butyl, 2-methyl-3-butyl, 2,2-dimethyl-1-propyl, 2-methyl-1-pentyl, 3-methyl -1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2,2- Dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl base
  • the alkyl group is C1-C10 alkyl, C1-C9 alkyl, C1-C8 alkyl, C1-C7 alkyl, C1-C6 alkyl, C1-C5 alkyl, C1-C4 alkyl , C1-C3 alkyl, C1-C2 alkyl or C1 alkyl.
  • the R 0 is preferably unsubstituted C1-C12 alkyl, more preferably unsubstituted C1-C6 alkyl, most preferably methyl or ethyl.
  • examples of the C1-C12 alkyl group include but are not limited to methyl, ethyl, n-propyl, isopropyl, 2-methyl-1-propyl , 2-methyl-2-propyl, 2-methyl-1-butyl, 3-methyl-1-butyl, 2-methyl-3-butyl, 2,2-dimethyl-1 -Propyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2 -Pentyl, 4-methyl-2-pentyl, 2,2-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl or neopentyl, etc.
  • the alkyl group is C1-C10 alkyl, C1-C9 alkyl, C1-C8 alkyl, C1-C7 alkyl, C1-C6 alkyl, C1-C5 alkyl, C1-C4 alkyl, C1-C3 alkyl, C1-C2 alkyl or C1 alkyl.
  • examples of C1-C8 alkyl groups include but are not limited to methyl, ethyl, n-propyl, isopropyl, 2-methyl-1-propyl, 2 -Methyl-2-propyl, 2-methyl-1-butyl, 3-methyl-1-butyl, 2-methyl-3-butyl, 2,2-dimethyl-1-propane Base, 2,2-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, etc.
  • the alkyl group is C1-C8 alkyl, C1-C7 alkyl, C1-C6 alkyl, C1-C5 alkyl, C1-C4 alkyl, C1-C3 alkyl, C1-C2 alkyl or C1 alkyl.
  • examples of C2-C8 alkenyl include vinyl, 1-propenyl, 2-propenyl, 1-methylvinyl, 1-butenyl, 2-but Alkenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1 -pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl or 3-methyl-1-butenyl and the like.
  • aryl is a cyclic aromatic hydrocarbon containing no heteroatoms in the ring.
  • Aryl groups include, but are not limited to, phenyl, azulenyl, heptenyl, biphenyl, fluorenyl, phenanthrenyl, triphenylene, pyrenyl, naphthacene, biphenylene, anthracenyl, and naphthyl .
  • Aryl groups can contain from 6 to 20 carbons in the ring portion of the group.
  • Aryl groups may be unsubstituted or substituted, preferably unsubstituted aryl groups.
  • the benzophenone derivative is selected from one of the following compounds:
  • the resulting reaction product is reacted with an end-capping agent
  • R 0 is optionally substituted C1-C12 alkyl, which has the same definition as above-mentioned R 0 , preferably unsubstituted C1-C12 alkyl, more preferably unsubstituted C1-C6 alkyl, Most preferably methyl or ethyl;
  • the blocking agent is selected from acid anhydride, acid chloride, isocyanate, acid anhydride is R 8 COOOCR 8 , acid chloride is R 8 COCl, isocyanate is R 9 NCO, isocyanate is R 9 NCO, R 8 and R 9 have the same formula (1) the same definition;
  • the molar ratio of the compounds of formula (2) and formula (3) is 1:(1-20).
  • reaction with the capping agent is optional, if both R 5 and R 5 ' in the compound of formula (1) are H, the step of reacting with the capping agent is not required here.
  • both R 5 and R 5 ' are groups other than H, a step of reacting with an end-capping agent is required if necessary.
  • R 10 is H.
  • R 11 is H or unsubstituted C1-C4 alkyl.
  • reaction temperature of the compound represented by formula (2) and the compound represented by formula (3) is 80-120° C., and the reaction time is 40-80 hours.
  • the catalyst is selected from alkali catalysts, preferably from hydroxides of alkali metals or alkaline earth metals, more preferably sodium hydroxide or potassium hydroxide.
  • the method further includes the steps of purifying and removing the solvent after reacting with the capping agent.
  • Exemplary purification methods such as purification by washing with water, solvent removal methods are distillation.
  • the preparation method of the benzophenone derivative comprises the following steps:
  • R 0 is optionally substituted C1-C12 alkyl, which has the same definition as above-mentioned R 0 , preferably unsubstituted C1-C12 alkyl, more preferably unsubstituted C1-C6 alkyl, Most preferably methyl or ethyl;
  • the molar ratio of the compounds of formula (2) and formula (3) is 1:(1-20).
  • the reaction temperature is 80-120° C.
  • the reaction time is 40-80 hours.
  • the base catalyst is sodium hydroxide or potassium hydroxide, and the molar ratio of the base catalyst to the compound of formula (2) is (0.05-0.2):1.
  • the temperature is lowered to 25-40° C., and the organic solvent is dichloroethane.
  • the preparation method of the benzophenone derivative comprises the following steps:
  • step 2) Take the reaction product obtained in step 1), mix it with an organic solvent and an end-capping agent, heat and stir to react, after the reaction is completed, add an alkaline solution to wash, then wash with water until neutral, remove the solvent, and obtain said benzophenone derivative;
  • R 0 is optionally substituted C1-C12 alkyl, which has the same definition as above-mentioned R 0 , preferably unsubstituted C1-C12 alkyl, more preferably unsubstituted C1-C6 alkane group, most preferably methyl or ethyl;
  • the blocking agent is selected from acid anhydride, acid chloride, isocyanate, acid anhydride is R 8 COOOCR 8 , acid chloride is R 8 COCl, isocyanate is R 9 NCO, isocyanate is R 9 NCO, R 8 and R 9 have the same formula (1) same definition.
  • the molar ratio of the compounds of formula (2) and formula (3) in step 1) is 1:(1 ⁇ 20); the reaction temperature is 80 ⁇ 120°C, and the reaction time is 40 ⁇ 80 hours; the base catalyst is hydrogen oxidation Sodium or potassium hydroxide, the molar ratio of the base catalyst to the compound of formula (2) is (0.05-0.2):1; after the reaction, the temperature is lowered to 25-40°C, and the organic solvent is dichloroethane.
  • the organic solvent described in step 2) is dichloroethane, and the mass ratio of the reaction product obtained in step 1) to the end-capping agent is (1-10): (0.5-5); the heating and stirring reaction temperature is 25-40°C, heating and stirring reaction time is 10-30h; the alkaline solution can be sodium carbonate solution, the mass concentration of sodium carbonate solution is 1-10%.
  • the preparation method of the benzophenone derivative comprises the following steps:
  • R 0 is optionally substituted C1-C12 alkyl, which has the same definition as above-mentioned R 0 , preferably unsubstituted C1-C12 alkyl, more preferably unsubstituted C1-C6 alkyl, Most preferably methyl or ethyl;
  • the blocking agent is selected from acid anhydride, acid chloride, isocyanate, acid anhydride is R 8 COOOCR 8 , acid chloride is R 8 COCl, isocyanate is R 9 NCO, isocyanate is R 9 NCO, R 8 and R 9 have the same formula (1) same definition.
  • the molar ratio of the compounds of formula (2) and formula (3) is 1:(1 ⁇ 20); the reaction temperature is 80 ⁇ 120°C, and the reaction time is 40 ⁇ 80 hours; the alkali catalyst is sodium hydroxide or hydrogen Potassium oxide, the molar ratio of the base catalyst to the compound of formula (2) is (0.05-0.2): 1; the organic solvent is ethylene dichloride.
  • the mass ratio of the compound of formula (2) to the blocking agent is (1-10): (0.5-5); after adding the blocking agent, the step of adding an organic amine is also included, and the organic amine is triethylamine , the molar ratio of the amount added to the capping agent is (1-1.2):1.
  • the preparation method of the benzophenone derivative comprises the following steps:
  • R 0 is optionally substituted C1-C12 alkyl, which has the same definition as above-mentioned R 0 , preferably unsubstituted C1-C12 alkyl, more preferably unsubstituted C1-C6 alkyl, Most preferably methyl or ethyl;
  • the blocking agent is selected from acid anhydride, acid chloride, isocyanate, acid anhydride is R 8 COOOCR 8 , acid chloride is R 8 COCl, isocyanate is R 9 NCO, isocyanate is R 9 NCO, R 8 and R 9 have the same formula (1) same definition.
  • the mol ratio of formula (2) and formula (3) compound is 1:(1 ⁇ 20);
  • the base catalyst is sodium hydroxide or potassium hydroxide, and the mol ratio of base catalyst and formula (2) compound is ( 0.05-0.2): 1; the organic solvent is ethylene dichloride.
  • the mass ratio of the compound of formula (2) to the blocking agent is (1-10): (0.5-5); after adding the blocking agent, the step of adding an organic amine is also included, and the organic amine is triethylamine , the molar ratio of the amount added to the capping agent is (1-1.2):1.
  • a photocuring agent composition including: a photoinitiator that can be used for radical polymerization and the above-mentioned benzophenone derivative.
  • a photocurable composition comprising: a photocuring agent component and a radically polymerizable ethylenically unsaturated compound, the photocuring agent component including the photocuring agent as described above Curing composition.
  • the photocurable composition includes:
  • a photocurable composition including the aforementioned photoinitiator composition has low mobility.
  • the added amount of the component (a) is 0.1-20% of the total weight of the photocurable composition, such as 1%, 5%, 10%, 15% or 20% .
  • the component (b) is selected from benzophenones (benzophenones and their derivatives other than the present application), thioxanthones , one or more of ⁇ -hydroxy ketone compounds, ⁇ -amino ketone compounds, acyl phosphine oxide compounds or oxime lipid compounds, preferably selected from benzophenone, 2-isopropylthioxanthone, At least one of the macromolecular photoinitiator series products Omnipol TX, Omnipol 910 or Omnipol TP of IGM Resins.
  • the photoinitiator Omnipol TX, photoinitiator Omnipol 910 or photoinitiator Omnipol TP is selected from the macromolecular photoinitiator series products Omnipol TX, Omnipol 910 or Omnipol TP of IGM Resin Company.
  • the added amount of the component (b) is 0.1-10% of the total weight of the photocurable composition, such as 0.1%, 2%, 4%, 6%, 8% or 10%.
  • Ethylenically unsaturated compounds mean ethylenically unsaturated monomers, oligomers, prepolymers and mixtures thereof, which are capable of undergoing free-radical polymerization.
  • the component (c) is selected from epoxy acrylate resin, polyurethane acrylate resin, polyester acrylate resin, polyether acrylate resin, acrylated polyacrylate , epoxy methacrylate resin, polyurethane methacrylate resin, polyester methacrylate resin, polyether methacrylate resin, acrylated polymethacrylate, allyl ether compound, acrylate mono At least one of monomers or methacrylate monomers.
  • the acrylate monomer or methacrylate monomer is independently monofunctional, difunctional or multifunctional.
  • the photocurable composition may also contain other additives to meet performance requirements, such as pigments, fillers, leveling aids, polymerization inhibitors, solvents, and the like.
  • a photocurable product which is formed by photocuring a photocurable composition, wherein the photocurable composition is the photocurable composition as described above, preferably
  • the light-cured product is selected from coatings, adhesives, printing Any kind of ink.
  • a curing method of a photocurable composition comprising:
  • Substrates include, but are not limited to: wood, paper, plastic, coating or metal, etc.
  • Coating methods include but are not limited to: offset printing, gravure printing, flexo printing, inkjet printing or 3D printing, etc.
  • the photocurable composition is cured by irradiating with UV-visible light having a wavelength of 200 to 425 nm, preferably by irradiating with UV-visible light having a wavelength of 365 to 405 nm.
  • the photocurable composition is cured.
  • the present application uses di(dialkylamino)benzophenone compounds containing hydroxyl groups and epoxy compounds as raw materials to carry out ring-opening addition reaction to synthesize a large molecular weight EMK derivative.
  • the obtained benzophenone derivative has the characteristics of good compatibility with photocuring system and low mobility.
  • the method is easy to synthesize, and the hydroxyl group can also be further capped.
  • the benzophenone derivative can be used as an important co-initiator in the UV photocuring formula to initiate photopolymerization of unsaturated carbon-carbon double bond compounds together with other photoinitiators.
  • the compound shown in formula (1) has very low mobility because of its relatively large molecular weight, and is suitable for replacing N, N, N, N-tetraethyl-4,4'-diaminobenzophenone in food packaging and printing formulations and other fields.
  • Omnirad DETX is 2,4-diethylthioxanthone, a product of IGM RESINS;
  • Omnirad EMK is Tetraethyl Michler's Ketone, a product of IGM RESINS;
  • Photomer 4072 is trimethylolpropane propoxyl (3) triacrylate, a product of IGM RESINS;
  • Photomer 3316 is a low-viscosity modified epoxy acrylate, a product of IGM RESINS.
  • This embodiment provides a preparation method of the compound shown in formula (4), comprising the following steps:
  • This embodiment provides a preparation method of the compound shown in formula (5), comprising the following steps:
  • Example 1 With 5.40 g of the product obtained in Example 1, add 17.0 g of dichloroethane, add 1.22 g (12 mmol) of acetic anhydride, heat and stir the reaction, the reaction temperature is 30° C., react for 12 hours, sample HPLC detection, to the obtained product in Example 1 The product reacted completely. Then add 6.4 g of 10% mass concentration sodium carbonate aqueous solution, wash once, and then wash with water until neutral. The solvent was distilled off under reduced pressure to obtain 5.62 g of the product of formula (5).
  • This embodiment provides a preparation method of the compound shown in formula (6), comprising the following steps:
  • This embodiment provides a preparation method of the compound shown in formula (7), comprising the following steps:
  • This embodiment provides a preparation method of the compound shown in formula (8), comprising the following steps:
  • This embodiment provides a preparation method of the compound shown in formula (9), comprising the following steps:
  • reaction temperature was 40°C, and the reaction was carried out for 4 hours, and all the components of the etherified product were completely reacted.
  • the solvent was dried under reduced pressure to obtain 5.94 g of the product of formula (9).
  • This embodiment provides a preparation method of the compound shown in formula (10), comprising the following steps:
  • This embodiment provides a photocurable composition, including the following components: Photomer 4072 4.8g, Photomer 3316 4.8g, the product of formula (4) in Example 1 0.2g and Omnirad DETX 0.2g.
  • the preparation method of the above-mentioned photocurable composition comprises the following steps: stirring the above-mentioned components at 60° C. until they are dissolved into a homogeneous solution, and then cooling down to room temperature to prepare a photocurable composition.
  • This embodiment provides a photocurable composition, including the following components: Photomer 4072 4.8g, Photomer 3316 4.8g, Example 2 formula (5) product 0.2g and Omnirad DETX 0.2g.
  • the preparation method of the above-mentioned photocurable composition comprises the following steps: stirring the above-mentioned components at 60° C. until they are dissolved into a homogeneous solution, and then cooling down to room temperature to prepare a photocurable composition.
  • This embodiment provides a photocurable composition, including the following components: Photomer 4072 4.8g, Photomer 3316 4.8g, Example 5 formula (8) product 0.2g and Omnirad DETX 0.2g.
  • the preparation method of the above-mentioned photocurable composition comprises the following steps: stirring the above-mentioned components at 60° C. until they are dissolved into a homogeneous solution, and then cooling down to room temperature to prepare a photocurable composition.
  • This embodiment provides a photocurable composition, including the following components: Photomer 4072 4.8g, Photomer 3316 4.8g, Example 7 formula (10) product 0.2g and Omnirad DETX 0.2g.
  • the preparation method of the above-mentioned photocurable composition comprises the following steps: stirring the above-mentioned components at 60° C. until they are dissolved into a homogeneous solution, and then cooling down to room temperature to prepare a photocurable composition.
  • This comparative example provides a photocurable composition, including the following components: Photomer 4072 4.8g, Photomer 3316 4.8g, Omnirad EMK 0.2g and Omnirad DETX 0.2g.
  • the preparation method of the above-mentioned photocurable composition comprises the following steps: stirring the above-mentioned components at 60° C. until they are dissolved into a homogeneous solution, and then cooling down to room temperature to prepare a photocurable composition.
  • Pendulum hardness test The above-mentioned photocurable compositions were respectively cured once on a coated glass plate (under a 395nm LED lamp) at a belt speed of 10m/min using a 25 ⁇ m wire rod, and the pendulum hardness after curing was tested.
  • Mobility test Use a 25 ⁇ m wire rod to cure the above photocurable composition on paper with a coating film length and width of 5 ⁇ 20cm, and cure it once under a 395nm LED lamp at a belt speed of 10m/min.
  • the cured paper is 100cm 2 , Put into the acetic acid aqueous solution of mass content 3% of 100g, place 10 days under 40 °C of conditions, then use HPLC to migrate to the photoinitiator component in the acetic acid aqueous solution (photoinitiator component refers to embodiment 1 formula (4) product component, embodiment 2 formula (5) product component, embodiment 5 formula (8) product component, embodiment 7 formula (10) product component or Omnirad EMK) carry out quantitative analysis.

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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)

Abstract

La présente demande concerne un dérivé de benzophénone, son procédé de préparation et son utilisation. Le dérivé de benzophénone a une structure telle que représentée par la formule (1). Le dérivé de benzophénone peut être utilisé en tant que co-initiateur important dans une formule de photodurcissement aux UV pour co-initier, conjointement avec d'autres photo-initiateurs, la photopolymérisation d'un composé à double liaison carbone-carbone insaturé. Le composé tel que représenté par la formule (1) a une mobilité très faible en raison d'un poids moléculaire relativement grand, et est approprié pour remplacer le N,N,N,N-tétraéthyl-4,4'-diaminobenzophénone dans les domaines de l'emballage de produits alimentaires, des formules d'impression, etc.
PCT/CN2023/079040 2022-03-02 2023-03-01 Dérivé de benzophénone, son procédé de préparation et son utilisation WO2023165522A1 (fr)

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CN202210198943.4A CN116730854A (zh) 2022-03-02 2022-03-02 一种二苯甲酮衍生物、制备方法及其用途

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104749882A (zh) * 2013-12-25 2015-07-01 Jsr株式会社 着色组合物、着色固化膜和显示元件
CN107686450A (zh) * 2017-10-27 2018-02-13 天津久日新材料股份有限公司 四乙基米氏酮的制备方法
CN112707830A (zh) * 2020-12-28 2021-04-27 天津久日新材料股份有限公司 一种四乙基米氏酮的制备方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104749882A (zh) * 2013-12-25 2015-07-01 Jsr株式会社 着色组合物、着色固化膜和显示元件
CN107686450A (zh) * 2017-10-27 2018-02-13 天津久日新材料股份有限公司 四乙基米氏酮的制备方法
CN112707830A (zh) * 2020-12-28 2021-04-27 天津久日新材料股份有限公司 一种四乙基米氏酮的制备方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
TAKANORI, S. ET AL.: "Electrochiroptical Response in Aqueous Media: 9,10-Dihydrophenanthrene-9,10-diyl Dications with Michlar’s Hydrol Blue Chromophores Attached with Oligoethylene Glycol Units", CHEMISTRY LETTERS, vol. 43, no. 7, 29 March 2014 (2014-03-29), XP009548371 *

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