CN109825034A - It is a kind of to realize sulfydryl-epoxy deep layer photocuring method and combinations thereof - Google Patents
It is a kind of to realize sulfydryl-epoxy deep layer photocuring method and combinations thereof Download PDFInfo
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- CN109825034A CN109825034A CN201910052139.3A CN201910052139A CN109825034A CN 109825034 A CN109825034 A CN 109825034A CN 201910052139 A CN201910052139 A CN 201910052139A CN 109825034 A CN109825034 A CN 109825034A
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- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/66—Mercaptans
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K7/00—Use of ingredients characterised by shape
- C08K7/02—Fibres or whiskers
- C08K7/04—Fibres or whiskers inorganic
- C08K7/14—Glass
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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Abstract
Sulfydryl-epoxy deep layer photocuring method and combinations thereof is realized the invention discloses a kind of, Photocurable composition is irradiated to generate reactive species in the point light source of 220-400nm using wave-length coverage, Photocurable composition is set to be uniformly dispersed in irradiation process, the heated rear baking of composition after irradiation, can be realized sulfydryl-epoxy deep layer photocuring；The Photocurable composition includes photocurable epoxy resin, photocurable mercapto monomers, photosensitizer, Photobase generator.The present invention keeps Photocurable composition evenly dispersed during ultraviolet light, be conducive to the generation of reactive species in this way, and it is dispersed in reactive species in system, it can avoid inactive kind of non-irradiated region and be difficult to realize solidification process, and then lead to not realize deep cure.The present invention can obtain required sulfydryl-epoxy deep layer photo-curing material with mock-up design according to actual needs, breach the problem that traditional sulfydryl-epoxy is difficult to deep layer photocuring, widened the application field of light polymerization technique.
Description
Technical field
The invention belongs to photopolymerization material fields, and in particular to it is a kind of realize sulfydryl-epoxy deep layer photocuring method and
Its composition.
Technical background
Sulfydryl-epoxy photocuring reaction is as a kind of typical " click chemistry " reaction, reaction high with regioselectivity
Mild condition, system shrinking percentage be small, without oxygen inhibition, hot property and mechanical performance are excellent the advantages that, be widely used in coating,
Adhesive, the preparation of high molecular material and the numerous areas such as modification and the preparation of biological responding material.But due to traditional purple
Outer light is limited in the penetrability of resin system, plus inner shield caused by initiator, pigment, filler etc. in system, is absorbed and instead
The effect of penetrating leads to not realize deep cure, existing sulfydryl-ring so that the non-irradiated region of system is difficult to realize solidification process
Oxygen photo-curing material solidifies the preparation for being mainly limited to two-dimensional material, limits its application.
The patent document of Publication No. CN105348414A and CN105330790A individually disclose a kind of deep layer cation
The method of photopolymerization and deep layer radical photopolymerization adds up-conversion into cationic system and free radical system respectively,
The solidified sample that depth of cure is 5 centimetres or more and 10 centimetres or more is respectively obtained, but this method addresses only cation
The problem of system and free radical system deep layer photopolymerization.The patent document of Publication No. CN105199643A provide it is a kind of sun from
The preparation method of the dual deep cure adhesive of the ultraviolet light and heat of subtype, the invention is by the way that photoinitiator is added into resin system
And thermal initiator, the curing depth of adhesive is improved, but the addition of thermal initiator also results in the uncontrollability of polymerization-filling.
Summary of the invention
In view of the above shortcomings of the prior art, the object of the present invention is to provide a kind of realization sulfydryl-epoxy deep layer light
Cured method and combinations thereof.
To achieve the above object, the present invention adopts the following technical scheme:
A method of realizing sulfydryl-epoxy deep layer photocuring, this method uses wave-length coverage in the point light of 220-400nm
Photocurable composition is irradiated in source makes Photocurable composition be uniformly dispersed to generate reactive species, in irradiation process, the combination after irradiation
It is dried after object is heated, sulfydryl-epoxy deep layer photocuring can be realized；The Photocurable composition includes photocurable asphalt mixtures modified by epoxy resin
Rouge, photocurable mercapto monomers, photosensitizer, Photobase generator and face/filler.
The present invention keeps Photocurable composition evenly dispersed during ultraviolet light, is conducive to the production of reactive species in this way
It is raw, and it is dispersed in reactive species in system, it can avoid inactive kind of non-irradiated region and be difficult to realize solidification process, in turn
Lead to not realize deep cure.
Preferably, the temperature dried after heating is 70~100 DEG C.
Preferably, the time dried after heating is 5~60min.
Preferably, making Photocurable composition be uniformly dispersed by stirring or ultrasound in irradiation process.
Realization sulfydryl-epoxy deep layer photocuring composition provided by the invention, the component including following mass parts: can light
40-80 parts of cured epoxy resin, 20-60 parts of photocurable mercapto monomers, 0.1-40 parts of photosensitizer, 0.2-8 parts of Photobase generator.
Preferably, the photocurable epoxy resin is glycidyl ether type epoxy resin, glycidol esters epoxy
One of resin, glycidyl amine epoxy resin, alicyclic based epoxy resin or linear aliphatic same clan epoxy resin are more
Kind.
Preferably, the photocurable mercapto monomers are trimethylolpropane tris (3-thiopropionate), bis- (3- sulfydryls
Propionic acid) glycol ester, 1,4- butanediol bis- (mercaptoacetates), tetraethylene glycol bis- (3-thiopropionates), four (3- sulfydryls third
Acid) pentaerythritol ester, four (3- mercaptobutyric acid) pentaerythritol esters, (3- mercaptobutyric acid) ester of 1,4- butanediol two or three (3- sulfydryls
Butoxyethyl group) one of chlorinated isocyanurates or a variety of.
Preferably, the photosensitizer is thioxanthone or derivatives thereof.
Preferably, the Photobase generator is tetraphenylboronic acid salt Photobase generator, thioxanthones Photobase generator or nitrogen
One of heterocycle amidine class Photobase generator is a variety of.
Preferably, further include face/filler, the face/filler be organic pigment, inorganic pigment, glass, carbon nanotube or
One of carbon fiber is a variety of.Face/the filler can be 0~4 part.
Compared with prior art, the invention has the following beneficial effects:
(1) present invention produces system by the point light source irradiation of 200-400nm wave-length coverage under room temperature or lower temperature
Liveliness proof kind makes system component be uniformly dispersed in irradiation process, is conducive to the generation of reactive species by way of stirring or ultrasound,
And reactive species is made uniformly to diffuse to non-irradiated area, drying after heated can be realized deep cure；Reactive species are in room temperature or more low temperature
Low without initiating power or efficiency of initiation to system under degree, stable system can keep mobility for a long time, be the processing and forming of material
Provide effective time window；After heating, system reactive species efficiency of initiation is promoted, can curing molding in the short time, thus real
Show that sulfydryl-epoxy is uniform, efficient deep cure.
(2) baking temperature is lower after the method for the present invention, and the curing reaction time is short, and technical process is efficient, simple, easy to operate, and
Applicability is wide, can be used for the fields such as light curing compound material, photocuring thick coating, is able to achieve most of photocurable sulfydryl-rings
The deep cure material homogeneity of the deep cure of oxygen system, acquisition is good, and the reaction time of deep cure and space are controllable, can
Different building shape is customized according to actual needs.
Detailed description of the invention
Fig. 1 is that photocuring reaction schematic diagram occurs for the present composition.
Specific embodiment
Further details of the technical solution of the present invention combined with specific embodiments below.
Realization sulfydryl-epoxy deep layer photocuring method provided by the invention, this method use 200-400nm wave-length coverage
Point light source irradiation Photocurable composition to generate reactive species, so that Photocurable composition is uniformly dispersed in irradiation process, after irradiation
Composition it is heated after dry, sulfydryl-epoxy deep layer photocuring can be realized；The Photocurable composition includes photocurable ring
Oxygen resin, photocurable mercapto monomers, photosensitizer and Photobase generator.
It wherein, can be in room temperature or lower temperature using the point light source irradiation Photocurable composition of 200-400nm wave-length coverage
Lower progress, such as 5~30 DEG C, the composition after irradiation can be injected as needed in the mold of different shape and depth, reheated solid
Chemical conversion type.
As shown in Figure 1, photocurable epoxy resin, photocurable mercapto monomers, photosensitizer, Photobase generator (can also be wrapped
Include face/filler) it injects in culture dish after mixing, at room temperature, mechanical stirring in point light source irradiation process induces excitation state light
Quick dose and Photobase generator generation energy transfer generation basic active kind, basic active kind uniformly diffuses to entire body under stirring
System dries generation photocuring reaction and obtains photo-crosslinking figure solidfied material after heated.
Wherein mixing time can be 5-30min, such as 10min, 15min, 20min, 25min；Stirring also could alternatively be
Other dispersing modes such as ultrasound.
It can be 70~100 DEG C, such as 80 DEG C, 85 DEG C, 90 DEG C, 95 DEG C that temperature is dried after heating；Heating time can for 5~
60min, such as 10min, 15min, 20min, 25min, 25min, 30min, 40min, 50min.
Photocurable composition provided by the invention includes: 40-80 parts of photocurable epoxy resin, photocurable mercapto monomers
20-60 parts, 0.1-4 parts of photosensitizer, Photobase generator 0.2-8；Preferably, it may also include face/0-4 parts of filler.
Wherein, photocurable epoxy resin can be 50 parts, 55 parts, 60 parts, 65 parts, 70 parts, 75 parts etc.；Photocurable sulfydryl
Monomer can be 25 parts, 30 parts, 35 parts, 40 parts, 45 parts, 50 parts, 55 parts etc.；0.1-4 parts of photosensitizer can be 0.5 part, 1 part, 1.5
Part, 2 parts, 2.5 parts, 3 parts, 3.5 parts etc.；Photobase generator can for 0.5 part, 1 part, 1.5 parts, 2 parts, 2.5 parts, 3 parts, 3.5 parts, 4 parts,
4.5 parts, 5 parts, 5.5 parts, 6 parts, 6.5 parts, 7 parts, 7.5 parts etc.；Face/filler can for 0.5 part, 0.8 part, 1 part, 1.5 parts, 2 parts,
2.5 parts, 3 parts, 3.5 parts etc..
Embodiment 1
The present embodiment realizes sulfydryl-epoxy deep layer photocuring composition, comprising:
Above-mentioned composition is injected into culture dish after mixing, at room temperature, using 385nm point light source in irradiation
After mechanical stirring 15min, it is transferred to the cylindrical Teflon mold and length and width, thick difference that diameter is 30mm, depth is 20mm
For in the rectangular die of 60mm, 12mm, 3.6mm, mold in 90 DEG C of baking ovens after dry 45min, can get having a size of 30mm ×
The cylinder pattern product and 60mm × 12mm of the completion of cure of 20mm × 3.6mm completion of cure rectangular body pattern product.
Cylindrical sample is cut into a series of different depth (h=0cm, h=0.5cm, h=1cm, h=1.5cm and h=
2cm) turn with 9 parts of different radii (r=0cm, r=0.5cm, r=1cm and r=1.5cm), the epoxy for measuring different piece
Rate is 80% or so, it is seen that Gu the homogeneity of reactionization degree is preferable.By carrying out crooked test, discovery to Rectangular samples
Its bending modulus reaches 7.0GPa.
Embodiment 2
The component and number of the present embodiment Photocurable composition are same as Example 1, the difference lies in that in the present embodiment
385nm point light source time for stir in irradiation is 20min, and irradiated sample by injection diameter is 3cm, the circle that depth is 2cm
In cylindricality Teflon mold and length and width, the thick respectively rectangular die of 60mm, 12mm, 3.6mm, mold is in 90 DEG C of baking ovens
In after to dry the time be 35min, other conditions are consistent.
The present embodiment obtains the cylinder that size is respectively 30mm × 20mm and 60mm × 12mm × 3.6mm completion of cure
With rectangular body pattern product, the cutting process with embodiment 1 is carried out to cylindrical sample, measure solidified sample in different radii and
The conversion ratio of the epoxy group of depth is about 89%, by carrying out crooked test to Rectangular samples, it is found that its bending modulus reaches
7.9GPa。
Embodiment 3
For the present embodiment with embodiment 2 the difference lies in that 1 part of filler is added, filler is glass fibre powder, is utilized
Sample by injection diameter is 3cm, the cylinder four that depth is 2cm in irradiation after mechanical stirring 20min by 385nm point light source
In vinyl fluoride mold and length and width, the thick respectively rectangular die of 60mm, 12mm, 3.6mm, mold is rear in 90 DEG C of baking ovens to be dried
35min, other conditions are consistent.
The present embodiment obtain completion of cure cylinder and rectangular body pattern product, according to embodiment 1 to sample at
Reason, measuring solidified sample in the conversion ratio of different radii and the epoxy group of depth is about 87%, and bending modulus increases to
12GPa。
Embodiment 4
For the present embodiment with embodiment 1 the difference lies in that 0.5 part of filler is added, filler is carbon nanotube, is utilized
Sample by injection diameter is 3cm, the cylinder four that depth is 2cm in irradiation after mechanical stirring 30min by 385nm point light source
In vinyl fluoride mold and length and width, the thick respectively rectangular die of 60mm, 12mm, 3.6mm, mold is rear in 90 DEG C of baking ovens to be dried
45min, other conditions are consistent.
The present embodiment obtains the cylinder pattern product of the completion of cure having a size of 3cm × 2cm, according to embodiment 1 to sample
Product are handled, and measuring solidified sample in the conversion ratio of different radii and the epoxy group of depth is about 82%, and bending modulus increases
Add to 12.8GPa.
Embodiment 5
The present embodiment realizes sulfydryl-epoxy deep layer photocuring composition, comprising:
Above-mentioned composition is injected into culture dish after mixing, at room temperature, using 365nm point light source in irradiation
After mechanical stirring 20min, by sample be transferred to 3cm × 2cm cylindrical Teflon mold and length and width, it is thick be respectively 60mm,
In the rectangular die of 12mm, 3.6mm, mold is rear in 90 DEG C of baking ovens to dry 30min, can get the colourless cylinder of completion of cure
Figure composite sample and rectangular body pattern product, are handled sample according to embodiment 1, find solidified sample in difference
Radius and the epoxy conversion ratio of depth about 91%, bending modulus 11.3GPa.
Embodiment 6
The present embodiment realizes sulfydryl-epoxy deep layer photocuring composition, comprising:
Above-mentioned composition is injected into culture dish after mixing, at room temperature, using 385nm point light source in irradiation
Sample after mechanical stirring 20min, pours into standard dog bone Teflon mold to (long * wide * thickness is 75mm*12.5mm*
2mm), 20min is dried after being put into later in 95 DEG C of baking ovens, can get the black dumbbell shape composite sample of completion of cure, Gu
Change the surface loop oxygen conversion rate of sample up to 89%, extension test finds its stretch modulus with 2805MPa.
Embodiment 7
The present embodiment realizes sulfydryl-epoxy deep layer photocuring composition, comprising:
Above-mentioned composition is injected into culture dish after mixing, at room temperature, using 365nm point light source in irradiation
Sample after mechanical stirring 10min, pours into standard dog bone Teflon mold to (long * wide * thickness is 75mm*12.5mm*
2mm), 25min is dried after being put into later in 90 DEG C of baking ovens, can get the dumbbell shape composite sample of completion of cure, solidifies sample
The surface loop oxygen conversion rate of product is up to 77%, stretch modulus 1162MPa.
Finally, it is stated that the above examples are only used to illustrate the technical scheme of the present invention and are not limiting, although referring to compared with
Good embodiment describes the invention in detail, those skilled in the art should understand that, it can be to skill of the invention
Art scheme is modified or replaced equivalently, and without departing from the objective and range of technical solution of the present invention, should all be covered at this
In the scope of the claims of invention.
Claims (10)
1. a kind of realize sulfydryl-epoxy deep layer photocuring method, which is characterized in that using wave-length coverage 220-400nm's
Point light source irradiates Photocurable composition to generate reactive species, so that Photocurable composition is uniformly dispersed in irradiation process, after irradiation
It is dried after composition is heated, sulfydryl-epoxy deep layer photocuring can be realized；
The Photocurable composition includes photocurable epoxy resin, photocurable mercapto monomers, photosensitizer and Photobase generator.
2. realization sulfydryl-epoxy deep layer photocuring method according to claim 1, which is characterized in that dried after heating
Temperature is 70~100 DEG C.
3. realization sulfydryl-epoxy deep layer photocuring method according to claim 2, which is characterized in that dried after heating
Time is 5~60min.
4. realization sulfydryl-epoxy deep layer photocuring method according to claim 1, which is characterized in that in irradiation process
Photocurable composition is set to be uniformly dispersed by stirring or ultrasound.
5. a kind of realize sulfydryl-epoxy deep layer photocuring composition, which is characterized in that the component including following mass parts: can
40-80 parts of photo-curing epoxy resin, 20-60 parts of photocurable mercapto monomers, 0.1-4 parts of photosensitizer, 0.2-8 parts of Photobase generator.
6. realization sulfydryl-epoxy deep layer photocuring composition according to claim 5, which is characterized in that it is described can light
Cured epoxy resin be glycidyl ether type epoxy resin, glycidyl ester epoxy resin, glycidyl amine epoxy resin,
One of alicyclic based epoxy resin or linear aliphatic same clan epoxy resin are a variety of.
7. realization sulfydryl-epoxy deep layer photocuring composition according to claim 5, which is characterized in that it is described can light
Solidification mercapto monomers are trimethylolpropane tris (3-thiopropionate), bis- (3- mercaptopropionic acid) glycol esters, 1,4- butanediol
Bis- (mercaptoacetates), tetraethylene glycol bis- (3-thiopropionates), four (3- mercaptopropionic acid) pentaerythritol esters, four (3- sulfydryl fourths
Acid) in pentaerythritol ester, (3- mercaptobutyric acid) ester of 1,4- butanediol two or three (3- sulfydryl butoxyethyl group) chlorinated isocyanurates
It is one or more.
8. realization sulfydryl-epoxy deep layer photocuring composition according to claim 5, which is characterized in that described photosensitive
Agent is thioxanthone or derivatives thereof.
9. realization sulfydryl-epoxy deep layer photocuring composition according to claim 5, which is characterized in that the light produces
Alkaline agent be one of tetraphenylboronic acid salt Photobase generator, thioxanthones Photobase generator or azacyclo- amidine class Photobase generator or
It is a variety of.
10. realization sulfydryl-epoxy deep layer photocuring composition according to claim 5, which is characterized in that further include
Face/filler, the face/filler are one of organic pigment, inorganic pigment, glass, carbon nanotube or carbon fiber or a variety of.
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| CN201910052139.3A CN109825034B (en) | 2019-01-21 | 2019-01-21 | Method for realizing mercapto-epoxy deep photocuring and composition thereof |
| PCT/CN2020/071868 WO2020151527A1 (en) | 2019-01-21 | 2020-01-14 | Method for implementing mercapto-epoxy deep photocuring and application thereof |
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| CN201910052139.3A CN109825034B (en) | 2019-01-21 | 2019-01-21 | Method for realizing mercapto-epoxy deep photocuring and composition thereof |
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| WO2020151527A1 (en) * | 2019-01-21 | 2020-07-30 | 江南大学 | Method for implementing mercapto-epoxy deep photocuring and application thereof |
| CN112080241A (en) * | 2020-09-24 | 2020-12-15 | 广东普赛达密封粘胶有限公司 | Photo-curing adhesive and preparation method and application thereof |
| CN113201203A (en) * | 2021-03-15 | 2021-08-03 | 苏州市汇涌进光电有限公司 | Light-cured transparent epoxy material and application thereof |
| CN116410682A (en) * | 2023-04-14 | 2023-07-11 | 南通康池新材料有限公司 | Thermosetting UV pressure-sensitive adhesive and preparation method thereof |
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| CN116410682A (en) * | 2023-04-14 | 2023-07-11 | 南通康池新材料有限公司 | Thermosetting UV pressure-sensitive adhesive and preparation method thereof |
| CN116410682B (en) * | 2023-04-14 | 2024-09-13 | 南通康尔乐复合材料有限公司 | Thermosetting UV pressure-sensitive adhesive and preparation method thereof |
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| CN109825034B (en) | 2020-10-30 |
| WO2020151527A1 (en) | 2020-07-30 |
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