WO2023216432A1 - Dérivé de thioxanthone, son procédé de préparation et son utilisation - Google Patents

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

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Publication number
WO2023216432A1
WO2023216432A1 PCT/CN2022/109095 CN2022109095W WO2023216432A1 WO 2023216432 A1 WO2023216432 A1 WO 2023216432A1 CN 2022109095 W CN2022109095 W CN 2022109095W WO 2023216432 A1 WO2023216432 A1 WO 2023216432A1
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WIPO (PCT)
Prior art keywords
photocurable composition
printing
thioxanthone derivative
formula
thioxanthone
Prior art date
Application number
PCT/CN2022/109095
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English (en)
Chinese (zh)
Inventor
王辰龙
赵文超
王永林
吕东旭
张珏
Original Assignee
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 WO2023216432A1 publication Critical patent/WO2023216432A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
    • C07D335/12—Thioxanthenes
    • C07D335/14—Thioxanthenes 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 in position 9
    • C07D335/16—Oxygen atoms, e.g. thioxanthones
    • 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
    • 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
    • C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • C08F22/10—Esters
    • C08F22/1006—Esters of polyhydric alcohols or polyhydric phenols, e.g. ethylene glycol dimethacrylate
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16

Definitions

  • the present application relates to the field of photosensitive polymer materials, and relates to a thioxanthone derivative, its preparation method and its use.
  • Photoinitiators play an important role in UV curing systems. They can absorb energy of specific wavelengths to generate active species to initiate the polymerization of the entire system. However, adding small molecule photoinitiators to the system will cause a series of disadvantages such as yellowing, odor, and toxicity in the system.
  • macromolecule photoinitiators have attracted widespread attention because they can overcome the inherent defects of small molecule photoinitiator systems.
  • the macromolecules themselves have low toxicity. After curing, the fragments of the photoinitiator remain small. The transformation of the photoinitiator fragments into macromolecules can greatly reduce its mobility, which can greatly reduce its toxicity, yellowing and unpleasant odor. .
  • the current macromolecule photoinitiator IGM Resin Company's Omnipol TX can further reduce the migration problem of small molecules, its migration amount is still high.
  • acrylic esters will be bonded to thioxanthone in order to obtain The amount of migration is lower, but the reduction is limited. Therefore, it is necessary to develop a new photoinitiator or co-photoinitiator to further reduce the amount of migration.
  • the technical problem to be solved by this application is to overcome the defect of high migration amount of photoinitiator or photoinitiator in the prior art, thereby providing a thioxanthone derivative, preparation method and use thereof.
  • R 3 is optionally substituted C1-C8 alkylene
  • B 1 and B 2 are each independently a single bond, In the formula, R 1 and R 2 are each independently H, -CH 3 , and m is an integer ranging from 0 to 5;
  • R is H or -CH 3 .
  • the group after removal of hydroxyl group of n-hydric alcohol refers to the groups other than hydroxyl group in n-hydric alcohol.
  • n-valent alcohols examples include but are not limited to: pentaerythritol, di(trimethylolpropane) ether or di(pentaerythritol) ether, etc.
  • n-valent alcohols also include ethyl oxidation derivatives of n-valent alcohols or propyl oxidation derivatives thereof .
  • substituted means that any one or more hydrogen atoms on a specified atom are replaced by a substituent, as long as the substituted compound is stable.
  • optionally substituted means that it may or may not be substituted. Unless otherwise specified, the type and number of substituents may be arbitrary based on what is achievable.
  • the alkyl group may be a straight-chain alkyl group or a branched-chain alkyl group.
  • n n 1 +n 2
  • n is an integer from 4 to 6, such as 4, 5 or 6
  • n 2 is an integer from 3 to 5, such as 3, 4 or 5
  • n 1 is nn 2 , That is, n 1 is 1, 2 or 3.
  • R 3 is optionally substituted C1-C8 alkylene, preferably unsubstituted C1-C8 alkylene.
  • C1-C8 alkylene include but are not limited to the terms used herein.
  • Alkylene means a straight or branched chain consisting solely of carbon and hydrogen.
  • alkylene include methylene, ethylene, propylene, butylene, pentylene and 3-methylpentylene.
  • R3 is methylene.
  • G is selected from at least one of the following structures,
  • G can also be selected from the following structures:
  • the average of the sum of P 1 , P 2 , P 3 and P 4 is 5;
  • G is selected from glycerol, diglycerol, triglycerol, triethanolamine, trimethylolpropane, dimethylolpropane, pentaerythritol, dipentatriol, residues of sugar alcohols and mixtures thereof; preferably, the The sugar alcohols are sorbitol, mannitol and xylitol.
  • the A group is at the 2- or 4-substituted position of the benzene ring.
  • R is H, n 1 is 1, and n 2 is an integer from 3 to 5.
  • the thioxanthone derivative is selected from any one of the following compounds:
  • the above compounds are easier to synthesize, and the product physical properties (such as fluidity and solubility) are more conducive to use in compositions.
  • This application also provides a method for preparing the thioxanthone derivative as described above, which includes the following steps:
  • step (b) reacting the reaction product of step (a) with the compound represented by formula (2) to obtain a thioxanthone derivative
  • R 4 is -OR 3 -COOH, and R 3 is optionally substituted C1-C8 alkylene.
  • R 3 has the same definition as in formula (1), preferably, R 3 is methylene.
  • step (a) and step (b) are performed independently in the presence of an acidic catalyst, a polymerization inhibitor and a solvent.
  • the acidic catalyst is selected from at least one of p-toluenesulfonic acid, benzenesulfonic acid or a strongly acidic cation exchange resin, and the added amount of the acidic catalyst is the mass of an acrylic compound. 1% to 20%, such as 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10% or 20%.
  • the acrylic compound may be acrylic acid or methacrylic acid.
  • a certain amount of polymerization inhibitor needs to be added to the reaction solution, and the polymerization inhibitor is selected from parabens.
  • the polymerization inhibitor is selected from parabens.
  • the amount of polymerization inhibitor added is 0.1% to 15% of the mass of the acrylic compound, For example, 1%, 2%, 3%, 4%, 5%, or 15%.
  • step (a) the reaction liquid of the n-alcohol in which G is the core group and the acrylic compound is subjected to extraction and separation, in order to remove unreacted n-alcohol and Its monoester and/or polyester.
  • the n-valent alcohol can be pentaethoxylated (EO5) pentaerythritol, with the structure The average of the sum of P 1 , P 2 , P 3 and P 4 is 5
  • G is selected from glycerol, diglycerol, triglycerol, triethanolamine, trimethylolpropane, dimethylolpropane, pentaerythritol, dipentatriol, residues of sugar alcohols and mixtures thereof; preferably, the The sugar alcohols are sorbitol, mannitol and xylitol.
  • step (a) water is used for extraction and separation, and the amount of water used is 0.1 to 0.5 times the weight of the n-valent alcohol with G as the core group, for example, 0.1 times, 0.2x, 0.3x, 0.4x or 0.5x.
  • the amount of water is below 0.1 times, the removal effect of intermediates with a low degree of esterification is not good.
  • the amount of water is 0.5 times, the intermediates with a low degree of esterification can be completely removed. If the water amount is increased further, it will lead to a waste of water.
  • step (b) it is preferable to add a catalyst. This is mainly because the polymerization inhibitor and catalyst will also separate with water during water extraction.
  • a catalyst In order to ensure the reaction of (b), add acrylic compound mass 1 ⁇ 20% of the catalyst, and the polymerization inhibitor is also 0.1% to 15% of the mass of the acrylic compound.
  • the reaction liquid with the compound represented by formula (2) is subjected to extraction and separation, with the purpose of removing components that do not contain thioxanthone groups.
  • an alkane solvent is used for extraction and separation.
  • the alkane solvent is selected from n-hexane, heptane, petroleum ether, cyclohexane or methylcyclohexane. of at least one.
  • Alkane solvents have good compatibility with fully esterified polyols, but have poor solubility for components containing thioxanthone. Therefore, components that do not contain thioxanthone groups can be well separated. .
  • step (b) the extraction separation meets at least one of the process conditions (1)-(2):
  • the extraction temperature is 25-70°C, preferably, the extraction temperature is 25-65°C;
  • the amount of alkane solvent used is 0.1 to 5 times the weight of the product.
  • the amount of alkane solvent used is 0.5 to 2 times the weight of the product.
  • the weight of the product here can be obtained by calculating the sum of the masses of the polyol, acrylic compound and thioxanthone contained in the product according to the structural formula of the product.
  • this application uses n-valent alcohol to first synthesize the intermediate polyol acrylate with at least 1 hydroxyl group with (meth)acrylic acid, and then removes the polyhydroxy compounds with insufficient esterification degree through extraction, and then Perform an esterification reaction with a carboxyl-containing thioxantrone compound, and use an alkane solvent to extract the components without thioxantrone groups to obtain the purified target product thioxanthone derivative, which contains more bis It contains bonding groups and does not contain non-curing components, which is more conducive to reducing the mobility of the photoinitiator.
  • the method includes:
  • the first esterification reaction liquid is extracted with water to remove unreacted n-valent alcohol or its ethoxylated or propoxylated derivatives and its monoesterified products and/or double esterified products.
  • the added amount of water is G is 0.1 to 0.5 times the weight of the n-alcohol of the core group;
  • the method includes:
  • the first esterification reaction liquid is extracted with water to remove unreacted n-valent alcohol or its ethoxylated or propoxylated derivatives and its monoesterified products and/or double esterified products.
  • the added amount of water is G is 0.1 to 0.5 times the weight of the n-alcohol of the core group;
  • the present application also provides a photocurable composition, comprising: (a) at least one thioxanthone derivative as described above and (b) at least one free radical polymerizable ethylenically unsaturated compound.
  • the photocurable composition including the aforementioned thioxanthone derivative has low mobility.
  • the added amount of component (a) is 0.1 to 25% of the total weight of the photocurable composition, and a more preferred addition amount is 0.1 to 25% of the total weight of the photocurable composition. 10%.
  • the added amount of component (b) is 90 to 99.9% of the total weight of the photocurable composition.
  • Ethylenically unsaturated compounds denote ethylenically unsaturated monomers, oligomers, prepolymers and mixtures thereof, which are capable of free radical polymerization.
  • the component (b) is selected from epoxy acrylate resin, modified epoxy acrylate resin, polyurethane acrylate resin, polyester acrylate resin, polyether acrylate resin Resin, acrylated polyacrylate, epoxy methacrylate resin, polyurethane methacrylate resin, polyester methacrylate resin, polyether methacrylate resin, acrylated polymethacrylate, vinyl At least one of a propyl ether compound, an acrylate monomer, or a methacrylate monomer.
  • the acrylate monomer or methacrylate monomer is independently monofunctional, difunctional or polyfunctional.
  • the acrylate monomer may be (3) propoxylated glyceryl triacrylate.
  • Additives can be used in the photocurable composition, and the additives are selected from triethylamine, triethanolamine, N-methyldiethanolamine, N,N-diethylethanolamine, amine additives Photomer 4250, N,N- Ethyl dimethylbenzoate, 2-ethylhexyl N,N-dimethylbenzoate, dimethylaminoethyl benzoate, 4-(dimethylamino)-benzoic acid-(2-ethyl) At least one of hexyl ester, 4-dimethylaminobenzoic acid ethyl ester, polyethylene glycol di-(p-dimethylaminobenzoic acid) ester or active amine.
  • the additives are selected from triethylamine, triethanolamine, N-methyldiethanolamine, N,N-diethylethanolamine, amine additives Photomer 4250, N,N- Ethyl dimethylbenzoate, 2-ethylhex
  • the photocurable composition may also contain other additives to meet performance requirements, such as pigments, fillers, leveling additives, defoaming additives, polymerization inhibitors, solvents, etc.
  • a photocurable product which is formed by photocuring a photocurable composition, wherein the photocurable composition is the photocurable composition as described above, preferably
  • the photocurable product is selected from any one of coatings, adhesives, and printing inks.
  • a curing method of a photocurable composition including:
  • the photocurable composition as described above is coated on the substrate; and, the photocurable composition is cured by using a light source with an emission band in the UV-visible light region.
  • 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, flexographic printing, inkjet printing or 3D printing, etc.
  • the coating amount of the photocurable composition is such that after photopolymerization, a coating with a thickness of 5 to 100 ⁇ m is obtained.
  • the thioxanthone derivatives provided by this application all contain acrylate groups, can participate in free radical polymerization, are fixed in the cross-linked network of the polymer, and do not contain non-curing components.
  • the thioxanthone derivative provided by this application has good compatibility with acrylate and has high migration stability. It does not need to add a solvent to dissolve the photoinitiator, and it can maintain a low migration amount even if a pigment is added. In terms of post-cured hardness, using the low-migration photoinitiator provided by this application will not significantly affect the post-cured hardness.
  • This embodiment provides a compound represented by formula (3), and its preparation method includes the following steps:
  • the upper cyclohexane solution contains pentaerythritol tetraacrylate.
  • the lower yellow oil is rotary evaporated under reduced pressure at 60°C to obtain 15.3g of a yellow transparent substance.
  • This embodiment provides a compound represented by formula (4), and its preparation method includes the following steps:
  • ethoxylated (EO5) pentaerythritol, 10g of acrylic acid, 0.9g of p-toluenesulfonic acid, 0.2g of 4-methoxyphenol, and 100g of toluene into a 250ml three-necked bottle. Pour air into the bottle and heat to 110°C. Reflux and reflux dehydration reaction for 6 hours. After the reaction solution reaches room temperature, add 10g of water, stir for 30 minutes, let stand for liquid separation, then add 0.6g of p-toluenesulfonic acid and 0.2g of 4-methoxyphenol to the separated organic phase.
  • EO5 pentaerythritol 10g of acrylic acid, 0.9g of p-toluenesulfonic acid, 0.2g of 4-methoxyphenol, and 100g of toluene into a 250ml three-necked bottle. Pour air into the bottle and heat to 110°C. Reflux and reflux dehydration reaction for 6
  • the upper n-hexane solution contains ethoxylated pentaerythritol tetraacrylate, and the lower yellow oil is evaporated under reduced pressure at 60°C to obtain 25.6g yellow transparent liquid, 1H-NMR data ⁇ : (CDCl3, ppm) 3.4-3.7 (integrated area 21.21, ethoxy hydrogen atom), 4.2-4.3 (integrated area 8.00, pentaerythritol methylene hydrogen atom), 4.7 -4.8 (integrated area 2.08, hydrogen atom of 2-carboxymethoxythioxanthone methylene group), 5.8-6.4 (integrated area 8.98, hydrogen atom of acryloyl group), 7.2-8.5 (integrated area 7.12, aromatic hydrogen atom ), the product was determined to be a compound of formula (4).
  • This embodiment provides a compound represented by formula (5), and its preparation method includes the following steps:
  • the separated organic The phase contains pentaerythritol triacrylate, then add 0.3g p-toluenesulfonic acid, 0.25g inhibitor 701, 6.29g 2-carboxymethoxythioxanthone to the organic phase, heat to reflux, reflux dehydration reaction for 4 hours, reduce to room temperature. Then add 2g sodium carbonate and 30g water, wash with water for 30 minutes, and let stand for liquid separation. The upper organic phase is washed twice with 30g of water, 30 minutes each time. After standing for liquid separation, the organic phase is evaporated at 60°C to remove the organic phase. A yellow viscous substance was obtained from the toluene in the solution, then 25g petroleum ether was added, stirred at room temperature for 30 minutes and then separated.
  • the petroleum ether phase contained dicondensate (1,1,1-trimethylolpropane) tetraacrylate, and the lower layer was yellow.
  • the oil was desolvated by rotary evaporation at 60°C to obtain 10.2g of yellow transparent liquid, 1H-NMR data ⁇ : (CDCl3, ppm) 0.8-0.9 (integrated area 6.00, dicondensation (1,1,1-trimethylolpropane ), 1.3-1.5 (integrated area 4.05, hydrogen atom of methylene group on dicondensation (1,1,1-trimethylolpropane)), 3.5-3.6 (integrated area 3.99, dicondensate) Dicondensation (1,1,1-trimethylolpropane) hydrogen atoms of methylene groups at both ends of the oxygen ether), 3.8-4.1 (integrated area 8.35, dicondensation (1,1,1-trimethylolpropane) -OCH2- hydrogen atom connected to the ester), 4.7-4.9 (
  • This embodiment provides a compound represented by formula (6), and its preparation method includes the following steps:
  • 2-Carboxymethoxythioxanthone heated to reflux, reflux dehydration reaction for 4 hours, then cooled to room temperature. Add 2g sodium carbonate and 40g water, wash with water for 30 minutes, and let stand for liquid separation. The upper organic phase is washed twice with 40g of water, 30 minutes each time. After standing for liquid separation, the organic phase is rotary evaporated at 60°C to remove the organic phase. of toluene, then add 40g of methylcyclohexane, keep it at 50°C, stir for 30 minutes and then separate the liquids. The upper methylcyclohexane phase contains dipentaerythritol hexaacrylate. The lower yellow oil is evaporated under reduced pressure at 60°C.
  • G3POTA is (3) propoxylated glyceryl triacrylate, produced by Taiwan Guojing Chemical Co., Ltd.;
  • Photomer 3316 is a low viscosity modified epoxy acrylate resin produced by IGM RESINS;
  • Photomer 4250 is an acrylated amine sensitizer, manufactured by IGM RESINS;
  • Ciba CROMOPHTAL BLUE A3R is a blue pigment produced by Ciba
  • ITX 2-isopropylthiaxantrone, and the manufacturer is IGM RESINS.
  • This embodiment provides a photocurable composition, and its preparation method includes the following steps: weigh the following raw materials: G3POTA 2.3g, Photomer 3316 2.3g, Photomer 4250 0.3g and formula (4) compound 0.2g; then put it at 60 °C, stir and dissolve, then lower to room temperature, and prepare a photocurable composition.
  • This embodiment provides a photocurable composition, and its preparation method includes the following steps: weigh the following raw materials: G3POTA 2.3g, Photomer 3316 2.3g, Photomer 4250 0.3g and formula (6) compound 0.2g; however, put it at 60 °C, stir and dissolve, then lower to room temperature, and prepare a photocurable composition.
  • This embodiment provides a photocurable composition, and its preparation method includes the following steps: weigh the following raw materials: G3POTA 2.3g, Photomer 3316 2.3g, Photomer 4250 0.3g, Ciba CROMOPHTAL BLUE A3R pigment 0.5g and the compound of formula (4) 0.2g; then stir and dissolve it at 60°C and then lower it to room temperature to prepare a photocurable composition.
  • This embodiment provides a photocurable composition, and its preparation method includes the following steps: weigh the following raw materials: G3POTA 2.3g, Photomer 3316 2.3g, Photomer 4250 0.3g, Ciba CROMOPHTAL BLUE A3R pigment 0.5g and the compound of formula (6) 0.2g; then stir and dissolve it at 60°C and then lower it to room temperature to prepare a photocurable composition.
  • This comparative example provides a comparative compound represented by formula (8), and its preparation method includes the following steps:
  • EO7 ethoxylated
  • This comparative example provides a photocurable composition, and its preparation method includes the following steps: weigh the following raw materials: G3POTA 2.3g, Photomer 3316 2.3g, Photomer 4250 0.3g and formula (8) compound 0.2g; then put it at 60 °C, stir and dissolve, then lower to room temperature, and prepare a photocurable composition.
  • This comparative example provides a photocurable composition, and its preparation method includes the following steps: weigh the following raw materials: G3POTA 2.3g, Photomer 3316 2.3g, Photomer 4250 0.3g and ITX 0.2g; then stir and dissolve them at 60°C Cool to room temperature and prepare a photocurable composition.
  • This comparative example provides a photocurable composition, and its preparation method includes the following steps: weigh the following raw materials: G3POTA 2.3g, Photomer 3316 2.3g, Photomer 4250 0.3g, Ciba CROMOPHTAL BLUE A3R pigment 0.5g and the compound of formula (8) 0.2g; then stir and dissolve it at 60°C and then lower it to room temperature to prepare a photocurable composition.
  • This comparative example provides a photocurable composition, and its preparation method includes the following steps: weigh the following raw materials: G3POTA 2.3g, Photomer 3316 2.3g, Photomer 4250 0.3g, Ciba CROMOPHTAL BLUE A3R pigment 0.5g and ITX 0.2g; then Stir and dissolve it at 60°C and then lower it to room temperature to prepare a photocurable composition.
  • the photocurable compositions obtained in Examples 5-8 and Comparative Examples 2-5 were coated on a glass plate using a 25 ⁇ m wire rod, and cured once under a 395 nm LED light source at a speed of 10 m/min, and the cured coating film was tested. Pendulum hardness.
  • Example 5 Example 6 Comparative example 2 Comparative example 3 Pendulum hardness 0.685 0.702 0.680 0.720 mobility 0.52% 0.25% 5.23% 69.75%
  • Example 7 Example 8 Comparative example 4 Comparative example 5 Pendulum hardness 0.620 0.655 0.650 0.662 mobility 0.95% 0.30% 8.25% 72.30%
  • the mobility of the compounds of formula (4) and formula (6) provided in this application is significantly lower than the comparative example of the compound of formula (8) containing only two acrylate double bonds. Since the low-migration photoinitiator provided in this application contains more double bonds, its mobility is significantly reduced compared to the comparative compound having two double bonds per molecule. Therefore, the low-migration photoinitiator provided in this application is more suitable for fields such as food and drug packaging that have strict requirements on initiator mobility.

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  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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Abstract

La présente demande concerne un dérivé de thioxanthone, son procédé de préparation et son utilisation. Le dérivé de thioxanthone a une structure représentée par la formule (1). Le dérivé de thioxanthone selon la présente invention contient plus de doubles liaisons, et peut participer à des réactions de polymérisation. Il ne contient pas de composants non durcissants, ce qui est bénéfique pour réduire le taux de mobilité des photo-initiateurs. Le dérivé de thioxanthone peut être utilisé dans les domaines de l'impression d'emballage alimentaire, l'impression d'emballage de médicament, la peinture de meuble, l'impression de livre, l'impression publicitaire et analogues.
PCT/CN2022/109095 2022-05-10 2022-07-29 Dérivé de thioxanthone, son procédé de préparation et son utilisation WO2023216432A1 (fr)

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