CN115710457B - Ultraviolet light curing composition and preparation method and application thereof - Google Patents
Ultraviolet light curing composition and preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to an ultraviolet light curing composition, which comprises the following components: 40-60 parts of oligomer, 40-55 parts of active thin monomer, 3-5 parts of photoinitiator, 2-5 parts of auxiliary agent and 0-1.5 parts of ultraviolet light absorber. Wherein the photoinitiator is a benzophenone derivative, and the structural formula is shown in (A); the ultraviolet absorbent is 1, 4-di (2-phenylsulfanyl phenyl) -1, 3-diacetylene. The two compounds can effectively absorb 250-360 nm ultraviolet light, and have good compatibility with resin or monomer and no smell. The photo-curing composition is prepared into transparent coating liquid according to a certain proportion, and the cured film which is coated on different base materials and cured is smooth and transparent and has excellent hardness and adhesive force. The ultraviolet absorbent 1, 4-di (2-phenylsulfanyl phenyl) -1, 3-diacetylene not only increases the ultraviolet resistance of the cured coating of the photo-curing composition, but also is easy to manufacture and store the photo-curing composition product.
Description
Technical Field
The present invention relates to a photocurable composition, and more particularly, to a photopolymerizable composition comprising a compound having a benzophenone skeleton and 1, 4-bis (2-phenylsulfanyl) 1, 3-diacetylene, and a method for preparing the same and use thereof.
Background
The ultraviolet curing technology is a technology for initiating prepolymer and monomer polymerization by utilizing ultraviolet light to excite a photoinitiator, has the advantages of environmental protection, high curing speed, less pollution and the like, and is widely used in the fields of coating, printing ink, electronic materials and the like. The photoinitiator in the composition system is a key component and determines various properties (such as adhesion, yellowing, hardness, odor, etc.) of the cured product. The benzophenone photoinitiator commonly used at the present stage has low ultraviolet absorption intensity and obvious oxygen polymerization inhibition phenomenon. Meanwhile, in the photocuring process, a plurality of photolysis products which are easy to volatilize and migrate and pollute the small molecular weight are generated. In particular, unsubstituted benzene rings tend to oxidize to quinone compounds and cause yellowing of the cured coating. Aiming at the defects, some research institutions and companies carry out proper modification and modification on the benzophenone type small molecular photoinitiators to develop a series of macromolecular benzophenone derivatives, and the increase of molecular weight can overcome the defects of easy migration, easy volatilization, odor and the like of the small molecular photoinitiators to a certain extent, but simultaneously the problems of poor compatibility caused by the growth of molecular chains and entanglement of intermolecular chains occur. Therefore, introducing a plurality of functional groups into the benzophenone molecular skeleton establishes a better structure-activity relationship, and developing a photoinitiator with high efficiency, low toxicity, low migration and difficult yellowing of a photo-cured product is an urgent need in the current photo-curing field.
On the other hand, due to the influence of ultraviolet rays in sunlight, the ultraviolet curing composition needs to be prepared under a light-shielding condition, the storage time is not long, the product is easy to deteriorate and turn yellow, is crisp and has reduced transparency, and an ultraviolet absorber needs to be added into the formula. Therefore, the design of photoinitiators and ultraviolet absorbers with high efficiency, low toxicity and low migration of photolysis products in ultraviolet light curing compositions is certainly a focus of research.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides an ultraviolet light curing composition, and a preparation method and application thereof.
The invention provides an ultraviolet light curing composition which comprises the following components in parts by mass: 40-60 parts of oligomer, 40-55 parts of active thin monomer, 3-5 parts of photoinitiator, 2-5 parts of auxiliary agent and 0-1.5 parts of ultraviolet light absorber;
the photoinitiator is a diphenyl ketone derivative (A) and has the following structural formula:
R 1 the method comprises the following steps: -H, -OCH 3 、or-Cl;
R 2 -R 3 the method comprises the following steps: -H, -OCH 3 、
R 4 The method comprises the following steps: -H,
The ultraviolet absorbent is 1, 4-di (2-phenylsulfanyl phenyl) -1, 3-diacetylene (B), and the structural formula is as follows:
the oligomer is acrylic oligomer, namely one or a mixture of two of epoxy acrylate, polyurethane acrylate, acrylate resin and the like.
The reactive diluent monomer is one or a mixture of two of monofunctional, difunctional and multifunctional reactive diluent monomers.
The auxiliary agent is amine donor (triethanolamine, methyldiethanolamine, triisopropanolamine, etc.), preferably triethanolamine.
Compared with the prior art, the invention has the beneficial effects that:
in the photo-curing composition, the ultraviolet initiator benzophenone derivative (A) is simple and convenient to prepare, raw materials are easy to obtain, and the yield is high; after the sulfonate group, the propylene oxygen group, the C-F bond and other groups are introduced on the basis of the diphenyl ketone skeleton, the function of the derivative is increased, the ultraviolet light with the wavelength of 250-325 nm can be effectively absorbed, and the absorption intensity is strong; the introduction of sulfonyl ester groups in the molecular structure improves the compatibility of the derivative with oligomers and monomers, and the preparation does not need heating and dissolving; the terminal ethylenic bond can participate in the crosslinking and curing of the oligomer or the monomer, so that the network crosslinking density is increased, and the phenomena of release and migration of benzene and yellowing of a cured coating can be reduced in the curing and film forming process and the product; the introduction of the C-F bond can reduce the surface energy of the compound, increase the concentration of the compound on the surface layer of the composition or the product, generate a high concentration effect, effectively inhibit the oxygen polymerization inhibition phenomenon of the photoinitiator, and facilitate the acceleration of photopolymerization.
In addition, the high-efficiency linear ultraviolet absorbent 1, 4-di (2-phenylsulfanyl phenyl) -1, 3-diacetylene not only increases the ultraviolet resistance of the cured coating of the photo-curing composition; meanwhile, no heat is generated after the energy is absorbed, the heat-sensitive adhesive is applicable to heat-sensitive substrates, and the effects of preventing the products from yellowing and deteriorating are achieved; but also is easy to manufacture and store the photo-curing composition product.
Therefore, the photo-curing composition can be used as a coating (containing a finishing agent) and can also be applied to the fields of printing ink, adhesive and the like.
Drawings
FIG. 1 ultraviolet absorption spectrum of derivatives A1-A4, benzophenone (BP)
FIG. 2 ultraviolet absorption spectrum of derivatives A5-A8, benzophenone (BP)
FIG. 3 is a diagram showing an experimental curing of a portion of a material having an ultraviolet light curable composition as an adhesive
Detailed Description
EXAMPLE 1 Synthesis of photoinitiator (A)
To the vessel was added benzophenone compound (1 mmol), triethylamine (1.5 mmol), and the mixture was dissolved in 3ml of methylene chloride, and then, under ice-water bath conditions, different sulfonyl chlorides (1.2 mmol) were slowly added, followed by stirring and reaction for 3 hours. After the reaction is finished, ethyl acetate is used for extraction, an organic phase is collected, then the organic phase is washed with water and dried, and the organic solvent is removed by rotary evaporation; and carrying out column chromatography separation by using petroleum ether/ethyl acetate (volume ratio is 10:1) as an eluent to obtain the benzophenone derivative (A).
TABLE 1 comparison of reaction starting materials and product derivatives (A1-A8)
Derivative A1: the structural formula of the compound is as follows:
white solid, yield 56%, m.p.81-83 ℃. 1 H NMR(600MHz,CDCl 3 )δ:7.66–7.33(m,8H),7.15(d,J＝7.9Hz,2H),7.00–6.82(m,2H),6.05(ddt,J＝16.4,10.7,5.2Hz,1H),5.40(dd,J＝56.0,13.9Hz,2H),4.59(d,J＝5.3Hz,2H),2.35(s,3H). 13 C NMR(151MHz,CDCl 3 )δ:21.70,69.31,110.09,113.50,118.61,125.48,128.02,128.50,129.67,130.01,131.81,132.06,132.24,132.85,137.26,145.49,147.95,161.53,192.87.
Derivative A2: the structural formula of the compound is as follows:
pale yellow solid, yield 62%, m.p.76-78 ℃. 1 H NMR(600MHz,CDCl 3 )δ:7.68–7.35(m,8H),7.15(d,J＝7.9Hz,2H),6.99–6.81(m,2H),3.87(s,3H),2.35(s,3H). 13 C NMR(151MHz,CDCl 3 )δ21.66,55.81,109.47,112.70,125.38,128.09,128.49,129.66,130.06,131.72,132.36,132.83,137.33,145.45,148.04,162.58,192.83.
Derivative A3: the structural formula of the compound is as follows:
pale yellow liquid with 96% yield. 1 H NMR(600MHz,CDCl 3 )δ:7.81–7.65(m,4H),7.42(d,J＝8.5Hz,1H),7.33(d,J＝8.1Hz,2H),7.08–6.97(m,2H),6.59–6.49(m,2H),3.89(s,3H),3.69(s,3H),2.47(s,3H). 13 C NMR(151MHz,CDCl 3 )δ:21.76,55.48,55.56,98.77,104.78,120.86,121.95,128.61,129.87,131.23,132.14,132.40,137.65,145.67,152.35,159.64,163.75,194.13.
Derivative A4: the structural formula of the compound is as follows:
white solid, yield 96%, m.p.121-123 ℃. 1 H NMR(600MHz,CDCl 3 )δ:7.78–7.71(m,6H),7.52–7.46(m,2H),7.36(d,J＝8.1Hz,2H),7.17–7.11(m,2H),2.48(s,3H). 13 C NMR(151MHz,CDCl 3 )δ:21.79,122.39,128.53,128.81,129.98,131.34,131.68,132.13,135.35,135.86,139.33,145.85,152.67,194.10.
Derivative A5: the structural formula of the compound is as follows:
pale yellow oily liquid with 63% yield. 1 H NMR(600MHz,CDCl 3 )δ:7.70–7.54(m,5H),7.45–7.37(m,3H),7.08–6.91(m,4H),6.06(ddt,J＝17.4,10.5,5.3Hz,1H),5.61–5.24(m,2H),4.62(dt,J＝5.4,1.6Hz,2H). 13 C NMR(151MHz,CDCl 3 )δ:69.37,110.18,113.63,116.40,116.52,118.64,125.30,128.22,130.00,130.80,130.83,131.38,131.44,132.03,132.29,133.03,137.24,147.90,161.67,165.48,167.17,192.73,215.04.
Derivative A6: the structural formula of the compound is as follows:
pale yellow solid, yield 89%, m.p.108-110 ℃.1H NMR (600 MHz, CDCl) 3 )δ:7.71–7.50(m,5H),7.47–7.38(m,3H),7.05(t,J＝8.5Hz,2H),6.98–6.87(m,2H),3.90(s,3H). 13 C NMR(151MHz,CDCl 3 )δ55.88,109.50,112.89,116.37,116.52,125.22,128.20,129.97,130.88,131.38,131.44,132.32,133.01,137.26,147.75,162.69,165.21,166.92,192.65.
Derivative A7: the structural formula of the compound is as follows:
pale yellow oily liquid with 96% yield. 1 H NMR(600MHz,CDCl 3 )δ7.94–7.80(m,2H),7.76–7.69(m,2H),7.42(d,J＝8.5Hz,1H),7.23(t,J＝8.4Hz,2H),7.09–7.02(m,2H),6.60–6.47(m,2H),3.89(s,3H),3.69(s,3H). 13 C NMR(151MHz,CDCl 3 )δ55.53,55.59,98.81,104.89,116.64,116.79,120.76,121.86,131.32,132.44,137.92,152.07,159.65,163.82,165.27,166.98,194.18.
Derivative A8: the structural formula of the compound is as follows:
white solid yield 97%, m.p.180-181 ℃. 1 H NMR(600MHz,CDCl 3 )δ7.97–7.87(m,2H),7.81–7.71(m,4H),7.52–7.45(m,2H),7.28–7.24(m,2H),7.19–7.13(m,2H). 13 C NMR(151MHz,CDCl 3 )δ116.77,116.91,122.37,128.85,131.37,131.44,131.73,135.18,136.10,139.38,152.36,165.36,167.07,193.96.
Ultraviolet light absorption Properties of derivative (A)
At a concentration of 1X 10 -5 mol·L -1 The ultraviolet absorption spectrum of the derivative A1-A8 at 200-400 nm is tested under the condition that the solvent is methylene dichloride, the characteristic absorption peak is determined, the molar extinction coefficient at the maximum absorption wavelength is calculated by using the Lambert-Beer law, and meanwhile, the molar extinction coefficient is compared with benzophenone BP (see table 2, attached figures 1 and 2). The compound can effectively absorb 250-310 nm ultraviolet light, has stronger ultraviolet light absorption performance, and the absorption intensity is 2-5 times of that of benzophenone.
TABLE 2 ultraviolet absorption of derivatives A1-A8, BP
Examples 2-9 preparation and use of the Photocurable composition (containing comparative example 1)
(1) The following examples are illustrative of the preparation of the photocurable compositions of the present invention, and in particular, the use of the photoinitiator benzophenone derivatives A1-A8 in UV curable coatings, but are not limited to the uses of the following examples.
The photocurable composition was formulated as follows:
experimental formula (mass portion):
the oligomer used therein was urethane acrylate (UV 2100 Jiangsu Sanmu group) and the monomer was 1, 6-hexanediol diacrylate (HDDA Jiangsu Sanmu group).
Working conditions:
adding 3g of benzophenone derivative or Benzophenone (BP) and 45g of 1, 6-hexanediol diacrylate (HDDA), 50g of polyurethane acrylate (UV 2100) and 2g of triethanolamine into a glass container, stirring uniformly at room temperature until the solution is transparent, carrying out ultrasonic degassing for 10 minutes, and standing for later use. The composition was then applied to a clean glass plate with a film thickness of 75um using an applicator and cured by irradiation with a medium pressure mercury lamp having a power of 400W. The performance of the coating film and the cured film was measured, and the evaluation results are shown in table 3.
a. And (3) surface dry time test: refers to a dry method or a cotton ball method.
b. Hardness test pencil hardness method was tested according to GB/T6739-1996. The scratch mark of the paint film is observed by using a film pencil scratch hardness tester, and a pencil with no scratch is taken as the pencil hardness of the film.
c. Adhesion test: cross-hatch measurement (see GB 9286-88). And judging whether the adhesive force of the coating is good or not through a cross-hatch experiment method. The degree of damage can be classified into 6 grades of 0 to 5 grades, preferably 0 grade, the film surface does not fall off any small lattice, the 5 grades are extremely poor, and serious peeling occurs on the film surface.
d. Gel fraction test, namely peeling and collecting the solidified film, heating the film in a 60 ℃ oven for 3 hours, cooling the film to room temperature, and weighing the film to be m 1 Then willSoaking the membrane in acetone solution for 24 hr, filtering, collecting the residue, oven drying, cooling to room temperature, weighing, and recording as m 2 Gel fraction= (m) 2 /m 1 )×100％。
TABLE 3 comparison of application Properties of benzophenone derivatives A1 to A8 with BP
From the test results in the above table, it can be seen that: compared with the commercially available free radical photoinitiator benzophenone BP, the benzophenone derivatives A1-A8 provided by the invention all show excellent curing speed, film forming hardness and adhesive force.
Example 10 (containing comparative examples 2-8)
The following examples are examples of the use of the photocurable composition in uv-curable coatings after addition of the uv-light absorber 1, 4-bis (2-phenylsulfanylphenyl) -1, 3-diacetylene (B) based on the formulation of the photocurable composition described above, but are not limited to the use of the following examples.
The photocurable composition was formulated as follows:
experimental formula (mass portion):
the oligomer used is polyurethane acrylic ester (UV 2100 Jiangsu Sanmu group), the monomer is 1, 6-hexanediol diacrylate (HDDA Jiangsu Sanmu group), and the photoinitiator is the benzophenone derivative A5.
Working conditions:
3g of benzophenone derivative (A5), 44g of 1, 6-hexanediol diacrylate (HDDA), 50g of polyurethane acrylate (UV 2100), 2g of triethanolamine and 0.8g of ultraviolet absorbent are added into a glass container, stirred evenly at room temperature until the coating liquid is transparent, degassed for 15 minutes by ultrasound and standing for standby. Dividing the prepared coating liquid into two parts, respectively, filling one part into a transparent glass bottle, covering a daily indoor storage, and evaluating the storage result (table 4); a part of the glass plate was coated with a paint film having a thickness of 75 μm using a paint brush, and then cured by an ultraviolet curing apparatus at a speed of 5 m/min (a light irradiation time of about 10 seconds), and cured coating properties were evaluated (Table 5).
Table 4 evaluation of storage results after uv-curable coating formulation
As is clear from Table 4, the preparation of the ultraviolet light paint is usually carried out under a dark condition, and the paint can not be stored for a long time under the influence of ultraviolet light in sunlight (comparative example 2). After the ultraviolet absorbent 1, 4-di (2-phenylsulfanyl phenyl) -1, 3-diacetylene is added, a stricter light-shielding condition is not needed when the coating is prepared, and the ultraviolet absorption effect is stronger than that of the commercial ultraviolet absorbent UV-0.
TABLE 5 evaluation results of ultraviolet light absorber B, UV-0 cured coating Performance
As can be seen from table 5, when no photoinitiator is added to the uv-curable coating composition, the composition cannot be cured into a film (comparative example 6), which shows that the uv-light absorber of the present invention does not participate in curing into a film, ensuring the storage property of the coating; the cured film obtained in example 10 had the advantages of firm film wiping, smooth and uniform surface, no irritating odor, and the like.
Example 11
The composition of example 6 was used as an adhesive for preliminary bonding experiments of different materials (glass, plastic, metal, cement board, template).
Working conditions: the composition of example 6 was coated with a clear coating liquid on a glass plate, a wood plate or a cement plate, respectively, with a thickness of 100 μm, and a glass, plastic, metal, wood plate or cement plate material was placed on the film, and then cured by an ultraviolet curing apparatus at a speed of 5 m/min (light irradiation time of about 10 seconds), and the respective adhesiveness was observed. The bonding is primarily judged to be firm by a shovel mode, so that the composition transparent coating liquid has strong bonding property, and is particularly suitable for bonding optical glass and electronic devices (see figure 3).
The photo-curing composition is not limited to the application of the photo-curing composition as a coating and an adhesive, and can be applied to the fields of finishing agents, printing ink and the like.
Claims (6)
1. The ultraviolet curing composition is characterized by comprising the following components in parts by weight: 40-60 parts of oligomer, 40-55 parts of reactive diluent monomer, 3-5 parts of photoinitiator, 2-5 parts of auxiliary agent and 0-1.5 parts of ultraviolet light absorber;
the photoinitiator is a diphenyl ketone derivative containing sulfonate groups, and the structural formula is as follows:
R 1 the method comprises the following steps: -H, -OCH 3 、or-Cl;
R 2 、R 3 、R 4 the method comprises the following steps: -H, -OCH 3 、R 2 、R 3 、R 4 It is necessary that one of the groups contains a sulfonate group.
The ultraviolet absorbent is 1, 4-di (2-phenylsulfanyl phenyl) -1, 3-diacetylene.
2. An ultraviolet light curing composition as defined in claim 1, wherein the oligomer is one or a mixture of two of epoxy acrylate, urethane acrylate and acrylate resin.
3. An ultraviolet light curing composition as claimed in claim 1, wherein the reactive diluent monomer is one or a mixture of two of monofunctional, difunctional and multifunctional reactive diluent monomers.
4. An ultraviolet light curing composition according to claim 1, wherein the auxiliary agent is triethanolamine, methyldiethanolamine or triisopropanolamine.
5. The ultraviolet light curing composition according to claim 1, wherein the weight portion of the oligomer is 50, the weight portion of the reactive diluent monomer is 45, the weight portion of the photoinitiator is 3, the weight portion of the auxiliary agent is 2, and the weight portion of the ultraviolet absorber is 0.8.
6. Use of the uv curable composition according to any one of claims 1-5 as a coating, ink or adhesive.
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| WO2004092105A1 (en) * | 2003-04-16 | 2004-10-28 | Hwan-Kyu Kim | Novel uv-curable perfluorinated, multifunctionalized acrylates monomers, copolyacrylates and their synthetic methods for photonic devices |
| CN108976470A (en) * | 2018-07-20 | 2018-12-11 | 山西大学 | Application of (2- the Phenylsulfanylphenyl) -1,3- diacetylene of 1,4- bis- as UV absorbers |
| CN110283080A (en) * | 2019-07-05 | 2019-09-27 | 山西大学 | A kind of fluorine-containing benzophenone derivates and its preparation method and application |
| CN111138290A (en) * | 2019-12-25 | 2020-05-12 | 山西大学 | Aromatic ring-containing benzophenone derivative and preparation method and application thereof |
| AU2020101245A4 (en) * | 2020-07-03 | 2020-08-13 | Shanxi University | A Benzophenone Derivative Containing Aromatic Ester Group and Preparation Method and Application Thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004092105A1 (en) * | 2003-04-16 | 2004-10-28 | Hwan-Kyu Kim | Novel uv-curable perfluorinated, multifunctionalized acrylates monomers, copolyacrylates and their synthetic methods for photonic devices |
| CN108976470A (en) * | 2018-07-20 | 2018-12-11 | 山西大学 | Application of (2- the Phenylsulfanylphenyl) -1,3- diacetylene of 1,4- bis- as UV absorbers |
| CN110283080A (en) * | 2019-07-05 | 2019-09-27 | 山西大学 | A kind of fluorine-containing benzophenone derivates and its preparation method and application |
| CN111138290A (en) * | 2019-12-25 | 2020-05-12 | 山西大学 | Aromatic ring-containing benzophenone derivative and preparation method and application thereof |
| AU2020101245A4 (en) * | 2020-07-03 | 2020-08-13 | Shanxi University | A Benzophenone Derivative Containing Aromatic Ester Group and Preparation Method and Application Thereof |
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