WO2016000477A1 - (4-phényl benzoyl)benzoate et son utilisation en tant que photoamorceur - Google Patents

(4-phényl benzoyl)benzoate et son utilisation en tant que photoamorceur Download PDF

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Publication number
WO2016000477A1
WO2016000477A1 PCT/CN2015/077081 CN2015077081W WO2016000477A1 WO 2016000477 A1 WO2016000477 A1 WO 2016000477A1 CN 2015077081 W CN2015077081 W CN 2015077081W WO 2016000477 A1 WO2016000477 A1 WO 2016000477A1
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Prior art keywords
compound
formula
group
phenylbenzoyl
benzoic acid
Prior art date
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PCT/CN2015/077081
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English (en)
Chinese (zh)
Inventor
赵文超
李静
李家齐
邵俊峰
姚丽秀
Original Assignee
北京英力科技发展有限公司
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Publication of WO2016000477A1 publication Critical patent/WO2016000477A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • 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
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
    • C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/48—Polymers modified by chemical after-treatment
    • 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
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • C09D163/10—Epoxy resins modified by unsaturated compounds

Definitions

  • the present invention relates to a macromolecularized (4-phenylbenzoyl) benzoate.
  • the compound can be used as a photoinitiator alone or in combination with other photoinitiators for formulating photocurable compositions, particularly suitable for photocuring varnishes, printing inks and the like which require low odor, low migration.
  • the present invention also provides a photopolymerizable composition comprising at least one compound of the present invention as a photoinitiator to formulate an unsaturated carbon-carbon double bond-containing compound.
  • Photoinitiators for photocuring varnish formulations require good cure speeds, especially good surface cure activity, low odor, low yellowness, and good solubility.
  • many small molecular weight substances are excluded from the permitted list, such as Compounds such as benzophenone, 2-hydroxy-2-methyl-1-phenyl-1-propanone, and methyl benzoylcarboxylate have small molecular weights, and they may be formed during the construction of the composition and after polymerization and film formation. Contamination caused by migration to its contact or volatilization into the air. Therefore, the tendency of the compound used for the photoinitiator to migrate out of the carrier to which it is attached or to be dissolved by the external medium should also be as small as possible.
  • Benzophenone is still the most widely used photoinitiator for ultraviolet (UV) cured overprint varnishes because of its good surface cure, high solubility, and low cost, but benzophenone has a strong odor and is extremely easy to print. Migrate and dissolve into packaged foods.
  • UV ultraviolet
  • the photoinitiator is highly reactive, has good solubility in the coating formulation, has a very low odor of the cured coating, and has a tendency to migrate and be dissolved much lower than most existing benzophenones and the like. There is a real need.
  • the inventors have surprisingly discovered a compound that meets the above requirements, namely (4-phenylbenzoyl)benzoic acid. ester.
  • the effective group properties of such compounds ensure that they have high initiating activity, polyfunctionalization allows them to maintain a relatively high effective weight per unit weight, and their core groups make them have good solubility and low in photopolymerizable compositions. Mobility.
  • the present invention provides a compound of formula I,
  • G is a residue of a polyhydroxy compound, the number of hydroxyl groups in the polyhydroxy compound is an integer n, and 2 ⁇ n ⁇ 6; x 1 is a positive integer, and 2 ⁇ x 1 ⁇ n, and x 2 is nx 1 ;
  • A is an oxygen atom or A is independent of each other or Group of which:
  • R 1 and R 2 represents a hydrogen atom, and the other represents a hydrogen atom, a methyl group or an ethyl group;
  • R is a hydrogen atom, a C 1 -C 12 alkyl acyl group, an aryl acyl group, or a C 2 -C 4 conjugated enoyl group.
  • the invention also provides a photoinitiator comprising at least one compound of formula I.
  • the invention also provides the use of a compound of formula I as a photoinitiator.
  • the present invention also provides a photoinitiator composition characterized in that the composition consists of two or more compounds of the formula I in any ratio.
  • the present invention provides a photopolymerizable composition comprising the following components:
  • a polymerizable component comprising at least one ethylenically unsaturated monomer or oligomer
  • a photoinitiator of the invention is a photoinitiator of the invention.
  • the present invention also provides a method of curing the photopolymerizable composition of the present invention, that is, coating the photopolymerizable composition on a substrate and placing it under light irradiation, especially under ultraviolet radiation. The coating is cured.
  • one or more mixtures of other types of known photoinitiators, as well as additives which improve the properties of the composition may be included in the composition; known photoinitiators are available from IGM Resins. Omnipol BP, Omnipol TX, etc.; as a polymerization promoter, for example, polyethylene glycol bis(p-dimethylaminobenzoic acid) ester, Cytec P115. Additives such as matting agents, antifoaming agents, leveling agents and the like to the composition can adjust the properties of the composition.
  • the photoinitiator of the present invention is used in an amount of 0.1-15% by weight of the composition, and usually it is 1-10%. Play a good photopolymerization.
  • the prepared photopolymerizable composition can be designed to be used on various substrate surfaces, such as paper, wood, plastic, metal, and coated and irradiated with light in a manner commonly used by those skilled in the art to complete curing. process.
  • the 2-(4-phenylbenzoyl)benzoate compound provided by the invention overcomes the defects of low stimulating activity and difficulty in production of benzophenone and other existing photoinitiators, and has extremely low odor and ultraviolet ray.
  • the curing formula has the advantages of high solubility, migration and tendency to be dissolved by the external medium; the photo-curing experiment results show that the photo-initiated activity per unit weight is almost equivalent to benzophenone itself, and its reactivity is significantly higher than that of commonly used diphenyl.
  • the 4-phenylbenzoylphenyl group of the compound of the formula I of the present invention is referred to as a photocurable effective group, and is bonded to (A)x 1 -G-(AR)x via a carbonyl group (-CO-).
  • a of 2 and (A) x 1 -G-(AR)x 2 is the core of the compound.
  • -CO-A- attached to 4-phenylbenzoylbenzene may be attached to any position of the phenyl group, for example, ortho-position with 4-phenylbenzoyl, Bit or alignment.
  • the specific A is an oxygen atom or a representative formula a group; more specific A represents an oxygen atom, or a group wherein one of R 1 and R 2 represents a hydrogen atom, the other represents a hydrogen atom, a methyl group or an ethyl group; a is 1 or 2; b is 4 or 5; and y is an integer from 1 to 30;
  • G is a residue of a polyhydroxy compound, the number of hydroxyl groups in the polyhydroxy compound is an integer n, and 2 ⁇ n ⁇ 6; x 1 is a positive integer, and 2 ⁇ x 1 ⁇ n, and x 2 is nx 1 ;
  • R is a hydrogen atom, a C 1 -C 12 alkyl acyl group, an aryl acyl group, or a C 2 -C 4 conjugated enoyl group.
  • x 1 may be an integer greater than or equal to 2
  • the core (A) x 1 -G-(A) x 2 group of the compounds of the invention has a significant effect on the properties of the compound.
  • the (A) x 1 -G-(A)x 2 group contains one or more polyether and/or polyester segments of low degree of polymerization, which makes the compound It is often in a liquid state and helps it dissolve in the coating formulation.
  • the molecular weight of the group (A) x 1 -G-(A)x 2 is not more than 2,000, and the excessively high molecular weight causes a low content per unit weight of the photoinitiator.
  • G is ethylene glycol, propylene glycol, butanediol, glycerol, trimethylolpropane, ditrimethylolpropane, pentaerythritol The residue of an alcohol or dipentaerythritol.
  • a residue of a polyhydroxy compound or "a residue of an alcohol” means a group remaining after the polyol or the alcohol loses one or more hydroxyl groups.
  • the residue of HOCH 2 CH 2 OH is HOCH 2 CH 2 - or -CH 2 CH 2 -.
  • other functional groups may be contained in addition to the hydroxyl group as long as these functional groups do not substantially adversely affect the synthesis or use of the compound of the present invention.
  • the compound of the present invention contains a free hydroxyl group or these free hydroxyl groups are esterified.
  • ester there is no particular restriction on the nature of the ester thus obtained, including lower molecular weight C 1 -C 12 fatty acid esters, C 2 -C 4 enoates, examples of such esters including acetates, propionates , butyrate, valerate or acrylate.
  • the numbers a, b and y in the above formula may not be integers, since in the preparation of the compounds, when the raw materials used are not In the case of a single compound, the product obtained is a mixture of several compounds of the formula (I).
  • a, b and y are integers for each individual molecule of the product, and a single compound can also be isolated separately, and those skilled in the art will appreciate that when a single polyol is used as the starting material A single pure compound can be obtained, but in practical applications, a mixture of different polymerization degrees of these polyhydroxy compounds is often used.
  • the compound of the present invention is obtained by reacting, for example, 2-(4-phenylbenzoyl)benzoic acid of the formula II or 3-(4-phenylbenzoyl)benzoic acid of the formula III with a core compound of the formula IV.
  • the esterification reaction is preferably carried out in the presence of a solvent, and the nature of the solvent is not critical to the present invention as long as it does not adversely affect the reagent or reaction.
  • Suitable solvents include: alkanes such as cyclohexane; aromatic hydrocarbons such as benzene, toluene or xylene.
  • the esterification reaction is selected in an acidic catalyst such as a sulfonic acid (for example p-toluenesulfonic acid or methanesulfonic acid), a mineral acid (such as sulfuric acid, hydrochloric acid or polyphosphoric acid) or a Lewis acid (for example boron trifluoride or organic titanate).
  • an acidic catalyst such as a sulfonic acid (for example p-toluenesulfonic acid or methanesulfonic acid), a mineral acid (such as sulfuric acid, hydrochloric acid or polyphosphoric acid) or a Lewis acid (for example boron trifluoride or organic titanate).
  • a sulfonic acid for example p-toluenesulfonic acid or methanesulfonic acid
  • a mineral acid such as sulfuric acid, hydrochloric acid or polyphosphoric acid
  • a Lewis acid for example boron trifluoride or organic titanate
  • the temperature of the esterification reaction can be varied within a relatively wide range depending on the conditions of the reaction and the nature of the reagents and the solvent, as long as the temperature is high enough to remove water generated during the reaction to ensure completion of the reaction. We find that it is usually close It is most convenient to carry out the reaction at the reflux temperature of the reaction mixture. The time required to complete the reaction varies widely, depending on the reaction temperature. Under the above optimum conditions, usually only 2 to 20 hours of reaction is required.
  • the above esterified product contains a free hydroxyl group which is esterified with another having a carboxylic acid group.
  • acids include acetic acid, butyric acid, acrylic acid or methacrylic acid.
  • the esterification is carried out by the same process as the above esterification reaction.
  • reaction After completion of the reaction, it may be subjected to a post-treatment by a usual method, for example, washing the mixture with water and/or alkali water, drying, and then evaporating the solvent under reduced pressure to give a product.
  • a post-treatment by a usual method, for example, washing the mixture with water and/or alkali water, drying, and then evaporating the solvent under reduced pressure to give a product.
  • the compounds of the invention are particularly suitable for use as photoinitiators, for example as photoinitiators in photocurable varnishes or inks. However, they can also be used as photoinitiators in many other photopolymerizable compositions at levels ranging from 0.1% to 15% by weight of the total composition.
  • Photocurable compositions employing the compounds of the present invention typically comprise at least one photocurable monomer and/or oligomer, a compound of the invention, and optionally a reactive diluent.
  • the composition also includes a colorant, i.e., a pigment.
  • the photocurable monomer or oligomer is preferably an ethylenically unsaturated compound, typically an acrylate oligomer or an acrylate monomer.
  • Suitable acrylate oligomers include: aliphatic or aromatic acrylate urethanes, polyether acrylates, polyester acrylates and epoxy acrylates (e.g., external bisphenol A epoxy acrylate).
  • Suitable acrylate monomers include: hexanediol diacrylate, trimethylolpropane triacrylate, ditrimethylolpropane tetraacrylate, dipentaerythritol pentaacrylate, polyether acrylate (eg ethoxylated) Trimethylolpropane triacrylate, glycerol propoxy triacrylate, ethoxylated pentaerythritol tetraacrylate, and epoxy acrylate (such as Cytec's Ebecryl 500), and diol diacrylate (for example, tripropylene glycol diacrylate).
  • the photopolymerizable composition of the present invention preferably contains at least one synergist such as an amino acrylate or a p-dimethylamino benzoate.
  • the synergist is preferably p-dimethylaminobenzoate, and in the case of varnish, the synergist is preferably an amino acrylate.
  • photocurable monomer or oligomer The amount of photocurable monomer or oligomer, photoinitiator, synergist, and optional colorant will vary depending on the type of varnish or ink, the particular equipment used for coating, and the application.
  • the compounds of formula I When used as a photoinitiator in varnishes or inks, the compounds of formula I generally comprise, in addition to the ingredients mentioned above, pigments, waxes, stabilizers and rheological aids.
  • n represents the degree of polymerization, which can be roughly derived from the molecular weight of the compound, and the values of a plurality of n in the same structural formula may be different.
  • Example 3 According to the procedure of Example 3, the raw material polytetrahydrofuran (average molecular weight 250) was replaced with polytetrahydrofuran (average molecular weight of 1000) to obtain a pale yellow viscous liquid in a yield of 82%, and the HPLC analysis showed that the target content was 98.0% in total.
  • Example 5 According to the process of Example 5, wherein the raw material polyethylene glycol (average molecular weight of 400) was replaced by polyethylene glycol (average molecular weight of 600) to obtain a pale yellow viscous liquid, the yield was 90%, and the HPLC analysis result: total target content 98.2%.
  • Example 5 According to the process of Example 5, the raw material polyethylene glycol (average molecular weight of 400) was replaced by polyethylene glycol (average molecular weight of 800) to obtain a pale yellow viscous liquid with a yield of 89%. HPLC analysis results: total target content 97.6%.
  • Photoinitiator 7 Amino acrylate auxiliaries (Ebecryl P115, Cytec) 8 Epoxy acrylate oligomer (6210G, Changxing Company) 25 Polyfunctional monomer, GPTA (EM2385 glycerol tripropoxylated triacrylate, Changxing) 60
  • the resulting varnish formulation was applied to a tinplate using a 10 micron bar coater and cured at a speed of 100 meters per minute using a 100 watt/cm medium pressure mercury lamp. Record the number of passes under the lamp required to obtain a good surface and complete cure, and immediately evaluate the odor level: a maximum of 5 and a minimum of 1. The results are shown in Table 4 below.
  • the compound of the present invention at least corresponds to or is close to the curing speed of benzophenone in terms of curing speed, and the curing speed is significantly higher than other benzophenone macromolecular light in Comparative Example 1 or Comparative Example 2.
  • Initiator All of the compositions in which the product of the examples was a photoinitiator had a lower odor than benzophenone after complete curing. All examples showed similar yellowness after curing.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un composé représenté par la formule (I), son procédé de synthèse et une utilisation de celui-ci en tant que photoamorceur. Dans la formule, chaque A représente un atome d'oxygène ou représente indépendamment un groupe de formule (AA), (BB) ou (CC); G représente un résidu d'un composé polyol comprenant n groupes hydroxyle et 2 ≤ n ≤ 6; x1 est un nombre entier positif, 2 ≤ x1 ≤ n et x2 est n-x; et R représente un atome d'hydrogène, un alkyl en C1-C12 acyle, un aryl acyle ou un alcénoyle en C2-C4 conjugué.
PCT/CN2015/077081 2014-07-02 2015-04-21 (4-phényl benzoyl)benzoate et son utilisation en tant que photoamorceur WO2016000477A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201410311886.1A CN105218372A (zh) 2014-07-02 2014-07-02 (4-苯基苯甲酰基)苯甲酸酯及其作为光引发剂的用途
CN201410311886.1 2014-07-02

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Cited By (1)

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WO2024083791A1 (fr) * 2022-10-18 2024-04-25 Sun Chemical B.V. Compositions d'encre, de revêtement et d'apprêt durcissables par énergie contenant des acrylates de glycérol hautement alcoxylés pour applications d'emballage en autoclave

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CN108623717B (zh) * 2017-03-20 2021-09-28 常州强力电子新材料股份有限公司 一种多官能度苯甲酰类大分子光引发剂及其制备方法

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CN103059168A (zh) * 2013-01-17 2013-04-24 长沙新宇高分子科技有限公司 一种二苯甲酮类光引发剂及其制备方法
WO2013107588A1 (fr) * 2012-01-20 2013-07-25 Cytec Surface Specialties, S.A. Liant photoréactif
WO2013107587A1 (fr) * 2012-01-20 2013-07-25 Cytec Surface Specialties, S.A. Liant amino photoréactif
CN103429680A (zh) * 2011-04-05 2013-12-04 湛新比利时股份有限公司 可辐射固化组合物
CN103443215A (zh) * 2011-04-05 2013-12-11 湛新比利时股份有限公司 可辐射固化组合物
WO2015010729A1 (fr) * 2013-07-23 2015-01-29 Allnex Belgium S.A. Photoamorceurs polymères

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CN103429680A (zh) * 2011-04-05 2013-12-04 湛新比利时股份有限公司 可辐射固化组合物
CN103443215A (zh) * 2011-04-05 2013-12-11 湛新比利时股份有限公司 可辐射固化组合物
WO2013107588A1 (fr) * 2012-01-20 2013-07-25 Cytec Surface Specialties, S.A. Liant photoréactif
WO2013107587A1 (fr) * 2012-01-20 2013-07-25 Cytec Surface Specialties, S.A. Liant amino photoréactif
CN103059168A (zh) * 2013-01-17 2013-04-24 长沙新宇高分子科技有限公司 一种二苯甲酮类光引发剂及其制备方法
WO2015010729A1 (fr) * 2013-07-23 2015-01-29 Allnex Belgium S.A. Photoamorceurs polymères

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024083791A1 (fr) * 2022-10-18 2024-04-25 Sun Chemical B.V. Compositions d'encre, de revêtement et d'apprêt durcissables par énergie contenant des acrylates de glycérol hautement alcoxylés pour applications d'emballage en autoclave

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