CN110218323A - One kind light-cured type composition of structures alone containing norbornene and light-cured type encapsulating material - Google Patents
One kind light-cured type composition of structures alone containing norbornene and light-cured type encapsulating material Download PDFInfo
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- CN110218323A CN110218323A CN201910489492.8A CN201910489492A CN110218323A CN 110218323 A CN110218323 A CN 110218323A CN 201910489492 A CN201910489492 A CN 201910489492A CN 110218323 A CN110218323 A CN 110218323A
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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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
- C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated compounds
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Abstract
The invention discloses a kind of light-cured type composition of structures alone containing norbornene and light-cured type encapsulating materials, and the light-cured type composition of structures alone containing norbornene includes: the first compound, contains at least one mercapto；Second compound, monomer or oligomer with an at least norbornene structure；And photoinitiator.Light-cured type encapsulating material then is cured by the light-cured type composition of structures alone containing norbornene.The mercapto of norbornene and the first compound that the present invention has by second compound is by the presence of photoinitiators, it is reacted by photocuring thiol-ene polymerization, obtain light-cured type encapsulating material, there is more preferably thermal stability and water resistance than the silicone monomers or oligomer light-cured type encapsulating material of the improvement of existing acrylate, so as to improve the problem that general acryl type photo-hardening material water preventing ability is insufficient and thermal stability is bad.
Description
Technical field
The present invention relates to a kind of composition and encapsulating materials, and in particular to a kind of light-cured type composition and light-cured type envelope
Package material.
Background technique
Epoxy resin or silicone resin are because of the translucency and thermal diffusivity that have, therefore by largely as light emitting diode
Encapsulating material, to protect the internal component of light emitting diode.
Existing encapsulating material can divide into thermohardening type, light-cured type or the encapsulation of two liquid types according to its different curing mode
Material (that is, combination of light-cured type and thermohardening type encapsulating material).Wherein, light-cured type encapsulating material meeting after light irradiates
Radical reaction or ionic reaction occurs, resin is made to crosslink reaction.For example, changing containing acrylate or epoxy acrylate
Property monomer or oligomer curing reaction can be completed in a short time after irradiation, and compare traditional thermohardening type potting resin tool
There are preferable chemical resistance, Physical Mechanical, water resistance.For example, Chinese patent CN101747860A discloses big function
The single component organic silicon packaging glue cured by ultraviolet of rate LED utilizes the ultraviolet curing monomelic silicone packaging plastic of great power LED
The polysiloxane oligomer system of acrylate is contained in encapsulating, i.e., the silicone monomers for containing acrylate using end and end
At light-cured type encapsulating material, curing time needed for shortening encapsulating material, to reach energy-efficient purpose.
However, can significantly deteriorate resin after using photo curable functional group (such as acrylate) improved resin characteristic
Thermal stability, the service life of component can be shortened when causing such resin as encapsulating material.
Therefore, there is the different previous light-cured type encapsulating material of one kind to be supplied, still at present to overcome light-cured type to encapsulate
The bad problem of material thermal stability.
Summary of the invention
The technical problem to be solved by the present invention is to overcome the deficiencies of existing technologies, a kind of list of structure containing norbornene is provided
Body light-cured type composition and light-cured type encapsulating material obtain having good by using component unlike the prior art
Thermal stability and water resistance encapsulating material.
Above-mentioned technical purpose of the invention has the technical scheme that
A kind of light-cured type composition of structures alone containing norbornene, comprising:
First compound contains at least one mercapto (sulfydryl)；
Second compound, monomer or oligomer with an at least norbornene structure；And
Photoinitiator.
As the first compound with mercapto of the invention, previously known person can be used.For example: 3- sulfydryl third
Sour methyl esters (methyl 3-mercaptopropionate), 3- mercaptopropionic acid 2- ethylhexyl (2-ethylhexyl 3-
Mercaptopropionate), 3- mercaptopropionic acid methoxybutyl (3-methoxybutyl mercaptopropionate) etc.
Simple function mercaptan；Ethylene glycol bis- (2 mercaptopropionic acid esters) (ethylene glycol bis (3-mercaptopropionate)),
Diethylene glycol bis- (2 mercaptopropionic acid esters) (diethylene glycol bis (3-mercaptopropionate)), 1,4- fourth
Glycol bis- (2 mercaptopropionic acid esters) (1,4-butanediol bis (3-mercaptopropionate)), bis- (the 3- mercaptos of ethylene glycol
Base butyrate) (ethylene glycol bis (3-mercaptobutyrate)), diethylene glycol be bis- (3- mercaptobutylate)
(diethylene glycol bis (3-mercapto butyrate)), bis- (3- the mercaptobutylate) (1,2- of 1,2- propylene glycol
Propylene glycol bis (3-mercaptobutylate)), bis- (3- the mercaptobutylate) (1,3- of 1,3- propylene glycol
Propylene glycol bis (3-mercaptobutylate)), bis- (3- the mercaptobutylate) (1,4- of 1,4- butanediol
Butanediol bis (3-mercaptobutylate)) etc. with two mercaptos multi-functional thiol；Trimethylolpropane
Three (3- mercaptobutylates) (trimethylolpropane tris (3-mercaptobutyrate)), trimethylolethane trimethacrylate
(3- mercaptobutylate) (trimethylolethane tris (3-mercaptobutyrate)), three [2- (3- mercaptobutyric acids
Base) ethyl] there are three mercaptan for the tool such as chlorinated isocyanurates (tris (3-mercaptobutyryloxyethyl) isocyanurate)
The multi-functional thiol of base；Pentaerythrite four (2 mercaptopropionic acid ester) (pentaerythritol tetrakis (2-
Mercaptopropionate)), pentaerythrite four (2- mercaptobutylate) (pentaerythritol tetrakis (2-
Mercaptobutylate)), pentaerythrite four (3- mercaptobutylate) (pentaerythritol tetrakis (3-
)) etc. mercaptobutylate there are four the multi-functional thiols of mercapto for tool.
For further increasing the gas barrier property that blocks water of double bond reactivity and crosslink density to improve encapsulating material, preferably
, first compound is the compound containing at least two mercaptos.On the other hand, it just further provides for more preferably being formulated
For stability, optical property and mechanical performance, first compound is preferably the second level with good stability in storage
Mercaptan compound.For example, first compound can be trimethylolpropane tris (3- mercaptobutylate), trihydroxy methyl second
Alkane three (3- mercaptobutylate), 1,4- butanediol bis- (3- mercaptobutylates), three [2- (3- mercaptobutyric acid base) ethyl] isocyanides urine
At least one of acid esters, but it is not limited only to this.
It is monomer or oligomer with an at least norbornene structure as second compound of the invention.It is described
The compound comprising at least one norbornene functional group is meant with an at least norbornene structure.For example, include
The general formula of the compound of one norbornene functional group can be R-N, wherein N is norbornene functional group, and R is hydrogen, chlorine, carbon
Straight-chain or branched alkyl or phenyl of the number for 1 to 18.The norbornene functional group belongs to low polar cycloolefin knot
Structure, and the norbornene functional group and mercapto have good reactivity, can form cross-linked network structure, provide good
Mechanical properties.Specifically, the second compound can be dodecyl norborneol -2- alkene -5- carboxylate (dodecyl
Norbornen-2-ene-5 carboxylate), 1,6 hexylene glycol, two-(norborneol -2- alkene -5- carboxylate) (1,6-
Hexanediol bis (norbornen-2-ene-5 carboxylate)), trimethylolpropane tris-(norborneol -2- alkene -5-
Carboxylate) (trimethylolpropane tris (norbornen-2-ene-5 carboxylate)), tetrahydrofuran drop ice
Piece -2- alkene -5- carboxylate (tetrahydrofurfuryl norbornen-2-ene-5 carboxylate, ring trihydroxy methyl
Propane dimethoxym ethane norborneol -2- alkene -5- carboxylate (cyclic trimethylolpropane formal norbornen-2-
Ene-5 carboxylate), dipropylene glycol two-(norborneol -2- alkene -5- carboxylate) (dipropylene glycol bis
(norbornen-2-ene-5 carboxylate)), tripropylene glycol two-(norborneol -2- alkene -5- carboxylate)
Monomers such as (tripropylene glycol bis (norbornen-2-ene-5 carboxylate)) or combinations thereof；Described
Two compounds can also for 2 to 6 functional groups and molecular weight between 800 to 5000 the anti-adoption ammoniacum norborneol -2- alkene-of rouge
5- carboxylate (aliphatic urethane norbornen-2-ene-5 carboxylates) has 2 to 6 functional groups
And molecular weight is between 800 to 5000 aromatic series polyurethane norborneol -2- alkene -5- carboxylate (aromatic urethane
Norbornen-2-ene-5 carboxylates), with 2 to 6 functional groups and molecular weight is dropped between 500 to 2000 epoxy
Borneol -2- alkene -5- carboxylate (epoxy norbornen-2-ene-5 carboxylates) has 2 to 6 functional groups and divides
Son measures polyesters norborneol -2- alkene -5- carboxylate (the polyester norbornen-2-ene-5 between 700 to 3000
The oligomers or combinations thereof such as carboxylates), but it is not limited only to this.
It just further increases the reaction efficiency between reactive group and more preferably formulation stability, optical property and machinery is provided
For performance, the second compound is dodecyl norborneol -2- alkene -5- carboxylate, 1,6 two-(norborneol -2- of hexylene glycol
Alkene -5- carboxylate), at least one of trimethylolpropane tris-(norborneol -2- alkene -5- carboxylate).
As photoinitiator of the invention, as long as can complete to be irradiated by light and promote the cured mesh of light-cured type composition
, it is not particularly limited.Preferably, the photoinitiator can for crack type photoinitiator, hydrogen-capture-type light initiator or its
Combination.
As the photoinitiator advanced optimized, the crack type photoinitiator can be styrax based compound
(benzoin-based compound)；Specifically, present invention crack type photoinitiator applicatory is for example: styrax
(benzoin), benzoin methyl ether (benzyl methyl ether), benzoin ethyl ether (benzyl ethyl ether), rest in peace
Fragrant isopropyl ether (benzyl isopropyl ether), benzoin isobutyl ether (benzyl isobutyl ether), benzyl diformazan
Base ketal (benzyl dimethyl ketal), 1- hydroxycyclohexyl phenyl ketone (l-hydroxy-cyclohexyl
Phenyl ketone), 2,2- dimethoxy -2- Phenyl ethyl ketone (2,2-dimethoxy-2-phenylacetophenone), 2-
Hydroxy-2-methyl -1- phenyl -1- acetone (2-hydroxy-2-methylpropiophenone) or (2,4,6- trimethylbenzene first
Acyl group) diphenyl phosphine oxide (diphenyl (2,4,6-trimethylbenzoyl) phosphine oxide), but not only limit
In this.
As the photoinitiator advanced optimized, the hydrogen-capture-type light initiator can be benzophenone-based compound
(benzophenone-based compound)；Specifically, present invention hydrogen-capture-type light initiator applicatory is for example: hexichol
Ketone (benzophenone), 4- phenyl benzophenone (4-phenyl benzophenone), 2- isopropyl thioxanthone (2-
Isopropylthioxanthone) or 2,4- diethyl thioxanthone (2,4-diethylthioxanthone), but not only
It is limited to this.
One kind light-cured type composition of structures alone containing norbornene of the invention, composition are combined with whole light-cured type
On the basis of the total amount of object, the dosage of the first compound is 25 wt% to 70 wt%, and the dosage of second compound is 25 wt% to 70
Wt%, the dosage of photoinitiator are 0.1 wt% to 20wt%.
As the dosage of the composition advanced optimized, for the performance of the photo-curing material improved, composition with
On the basis of the total amount of whole light-cured type composition, the dosage of the first compound is 35 wt% to 60 wt%, second compound
Dosage is 35 wt% to 60 wt%, and the dosage of photoinitiator is 0.5 wt% to 10 wt%.
The present invention also provides a kind of light-cured type encapsulating materials, are consolidated by the light of structures alone containing norbornene as previously described
Change type composition then is cured.
Preferably, the energy of the illumination is 100mJ between 2000 mJ.Accordingly, this creation can be without increasing illumination
Under the premise of energy, photo-hardening type composition completion of cure is enabled, is obtained so that it is guaranteed that solidifying the photo-hardening type encapsulating material formed
It obtains good surface drying.
In conclusion the invention has the following advantages:
(1) mercapto for the norbornene and the first compound that the present invention has by second compound passes through in photoinitiator
In the presence of, it is reacted by photocuring thiol-ene polymerization, obtains light-cured type encapsulating material, it is more poly- than the improvement of existing acrylate
Siloxanyl monomers or oligomer light-cured type encapsulating material have more preferably thermal stability and water resistance, so as to specifically improve one
As acryl type photo-hardening material water preventing ability is insufficient and thermal stability is bad problem.
(2) encapsulating material that the present invention is obtained by the method for photocuring, preparation method is fast, the property of obtained encapsulating material
Can be good, be conducive to save existing resource.Encapsulating material can protect the component of the inside not interfered by temperature, aqueous vapor and oxygen, into
And ensure the service life of encapsulating material inner assembly.
Specific embodiment
The invention will be further described below.Following embodiment is only used for clearly illustrating technical side of the invention
Case, and not intended to limit the protection scope of the present invention.
Photoinitiator: bis- (2,4, the 6- trimethylbenzoyl) phosphine oxides of phenyl, marque: Irgacure 819, purchase
From BASF AG.
Photoinitiator: diphenyl (4- thiophenyl) phenylbenzimidazole sulfonic acid hexafluorophosphate, marque: CPI-100P is purchased from
San-Apro company.
First compound: three (3- mercaptobutyric acid) trimethylolethane esters, marque: TEMB is purchased from Showa electrician
Company.
First compound: three (3- mercaptobutyric acid) trihydroxymethylpropanyl esters, marque: TPMB is purchased from Showa electrician
Company.
Second compound: dodecyl norborneol -2- alkene -5- carboxylate, marque: LN is derived from Heng Qiao industry companies.
Second compound: trimethylolpropane tris-(norborneol -2- alkene -5- carboxylate), marque: TMPTN is derived from
Heng Qiao industry companies.
Acrylate monomer: 2- dodecylacrylate, marque: AgisynTM2896, it is purchased from Xin Limei company.
Acrylate monomer: trimethylolpropane trimethacrylate, marque: AgisynTM2811, it is purchased from Xin Limei
Company.
Light-cured type silicone resin: 2- (3,4- epoxycyclohexyl) ethyl trimethoxy silane-dimethyldimethoxysil,ne
Copolymer, marque: 6730A is derived from Heng Qiao industry companies.
Embodiment 1 to 4 and comparative example 1 to 3: light-cured type composition
It is matched according to shown in the following table 1, the first compound, second compound and photoinitiator is sequentially added in reaction flask, passed through
The light-cured type composition of embodiment 1 to 4 Yu comparative example 1 to 3 is respectively obtained after stirring.
Embodiment 5 to 8 and comparative example 4 to 6: production light-cured type encapsulating material test film
With about 3 cm of diameter, 400 μm of thickness of transparent mould, by previous embodiment 1 to 4 and the light-cured type of comparative example 1 to 3
Composition is respectively filled in wherein；Reuse D lamp, make its solidification after 1000 mJ of prolonged exposure energy accumulation, from mold remove after according to
The secondary light-cured type encapsulating material test film for obtaining embodiment 5 to 8 and comparative example 4 to 6.
The performance test of the light-cured type encapsulating material test film of embodiment 5 to 8 and comparative example 4 to 6 is as shown in table 2 below,
The light-cured type encapsulating material test film that each embodiment and comparative example are about 400 μm of film thickness.
Table 1: the proportion of the light-cured type composition of embodiment 1 to 4 and comparative example 1 and 3.
By detecting heat resistance, thermal stability and the water boiling resistance of light-cured type encapsulating material, to light-cured type package material
The characteristic of material is analyzed.
Embodiment 5 to 8 and comparative example 4 made of the light-cured type composition of embodiment 1 to 4 and comparative example 1 to 3 solidifies
It is as shown in table 2 below to the heat resistance of 6 light-cured type encapsulating material test film, thermal stability and water boiling resistance result.To ensure
The experiment meaning of specificity analysis, each light-cured type composition form each light-cured type encapsulating material with identical curing method, and
Each light-cured type encapsulating material is also analyzed by identical test method.It can be seen that the spy of each light-cured type encapsulating material
Sex differernce in each light-cured type encapsulating composition mainly due to forming caused by difference.
Test method:
Heat resistance: each light-cured type encapsulating material test film is placed in 180 °C of baking ovens 120 minutes, taking-out temperature rolls back room
Wen Hou, whether there is or not Yellowings for observation.If light-cured type encapsulating material test film without Yellowing, determines that heat resistance is good, under
"○" is expressed as in table 2；If light-cured type encapsulating material test film has Yellowing, determine that heat resistance is bad, in the following table 2
It is expressed as "×".
Thermal stability (TGA analysis): each light-cured type encapsulating material test film is analyzed with thermogravimetric analyzer, by thermogravimetric
Degradation temperature measured by analyzer assesses the thermal stability of each light-cured type encapsulating material test film；Degradation temperature, that is, material
Cracking temperature, the higher expression thermal stability of degradation temperature is better.
Water boiling resistance: each light-cured type encapsulating material test film is placed in 100 °C of boiling water 120 minutes, after taking-up is dried,
Whether there is or not white haze phenomenons for observation.If light-cured type encapsulating material test film without white haze phenomenon, determines that water boiling resistance is good, in the following table 2
In be expressed as "○"；If light-cured type encapsulating material test film has white haze phenomenon, represents aqueous vapor and penetrate into light-cured type encapsulating material
In test film, then determine that water boiling resistance is bad, is expressed as "×" in the following table 2.
Table 2: light-cured type selected by the photocuring encapsulating material test film of production embodiment 5 to 8 and comparative example 4 to 6
The specificity analysis knot of the photocuring encapsulating material test film of the sample number into spectrum and embodiment 5 to 8 and comparative example 4 to 6 of composition
Fruit.
| Embodiment 5 | Embodiment 6 | Embodiment 7 | Embodiment 8 | Comparative example 4 | Comparative example 5 | Comparative example 6 | |
| The sample number into spectrum of light-cured type composition | Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 | Comparative example 1 | Comparative example 2 | Comparative example 3 |
| Heat resistance | ○ | ○ | ○ | ○ | × | × | ○ |
| Degradation temperature (DEG C) | 354.7 | 353.6 | 353.4 | 349.9 | 341.1 | 337.9 | 350.0 |
| Water boiling resistance | ○ | ○ | ○ | ○ | ○ | ○ | × |
Shown in table 2 as above, it is elected to complete at least monomer of a norbornene structure or the second compound of oligomer
When portion replaces the acrylic ester polymerization monomer practised (the light-cured type composition of the embodiment of the present invention 1 to 4), made from
Light-cured type encapsulating material test film (i.e. embodiment 5 to 8) all has the advantages that heat resistance is good.
On the contrary, the light-cured type encapsulating material test film of comparative example 4 and 5, the light-cured type combination as selected by it
Be mainly general acrylic ester polymerization monomer in object, cause the light-cured type encapsulating material test film of comparative example 4 and 5 all there are
The disadvantage of water boiling resistance difference.
In addition, by the light-cured type encapsulating material test film of embodiment 5 to 8 and the light-cured type encapsulating material of comparative example 6
The water boiling resistance comparison result of test film is it is found that the light-cured type composition institute shape added with the first compound and second compound
At light-cured type encapsulating material test film (embodiment 5 to 8), water boiling resistance be better than comparative example 6 light-cured type package material
Expect test film.
The above analysis result in light-cured type composition it is found that add the list with an at least norbornene structure
It is solid to be conducive to promotion light for the technological means such as the second compound of body or oligomer and the composition for adjusting light-cured type composition
The water boiling resistance and heat resistance of change type encapsulating material, and then promote photo-curing type of the invention and sealed applied to light emitting diode
The application value of dress.
The above is only a preferred embodiment of the present invention, protection scope of the present invention is not limited merely to above-mentioned implementation
Example, all technical solutions belonged under thinking of the present invention all belong to the scope of protection of the present invention.It should be pointed out that for the art
Those of ordinary skill for, several improvements and modifications without departing from the principles of the present invention, these improvements and modifications
It should be regarded as protection scope of the present invention.
Claims (8)
1. a kind of light-cured type composition of structures alone containing norbornene, characterized in that include:
First compound contains at least one mercapto；
Second compound, monomer or oligomer with an at least norbornene structure；And
Photoinitiator.
2. one kind structures alone containing norbornene light-cured type composition according to claim 1, characterized in that described the
One compound is second level mercaptan compound.
3. one kind structures alone containing norbornene light-cured type composition according to claim 1, characterized in that described the
One compound is free trimethylolpropane tris (3- mercaptobutylate), trimethylolethane trimethacrylate (3- mercaptobutylate), 1,4-
At least one of butanediol bis- (3- mercaptobutylates) and three [2- (3- mercaptobutyric acid base) ethyl] chlorinated isocyanurates.
4. one kind structures alone containing norbornene light-cured type composition according to claim 1, characterized in that described the
Two compounds are dodecyl norborneol -2- alkene -5- carboxylate, 1,6 hexylene glycols two-(norborneol -2- alkene -5- carboxylate), three
At least one of hydroxymethyl-propane three-(norborneol -2- alkene -5- carboxylate).
5. one kind light-cured type composition of structures alone containing norbornene according to claim 1, characterized in that the light
Initiator is crack type photoinitiator, hydrogen-capture-type light initiator or combinations thereof.
6. described in any item a kind of light-cured type compositions of structures alone containing norbornene according to claim 1 ~ 5, feature
It is that for composition on the basis of the total amount of whole light-cured type composition, the dosage of the first compound is 25 wt% to 70 wt%, the
The dosage of two compounds is 25 wt% to 70 wt%, and the dosage of photoinitiator is 0.1 wt% to 20wt%.
7. one kind light-cured type composition of structures alone containing norbornene according to claim 6, characterized in that composition
On the basis of the total amount of whole light-cured type composition, the dosage of the first compound is 35 wt% to 60 wt%, second compound
Dosage be 35 wt% to 60 wt%, the dosage of photoinitiator is 0.5 wt% to 10 wt%.
8. a kind of light-cured type encapsulating material, the light of the structures alone containing norbornene as described in any one of claim 1 ~ 5 is solid
Change type composition then is cured.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114345273A (en) * | 2021-12-30 | 2022-04-15 | 南京恒桥化学技术材料有限公司 | Preparation method of photocuring composition |
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| CN114345273B (en) * | 2021-12-30 | 2024-03-08 | 南京恒桥化学技术材料有限公司 | Preparation method of photo-curing composition |
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Application publication date: 20190910 |