CN105295050A - Triaryl sulfonium salts containing silicon-oxygen chain and application thereof in photocuring epoxy resin - Google Patents

Triaryl sulfonium salts containing silicon-oxygen chain and application thereof in photocuring epoxy resin Download PDF

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CN105295050A
CN105295050A CN201410276638.8A CN201410276638A CN105295050A CN 105295050 A CN105295050 A CN 105295050A CN 201410276638 A CN201410276638 A CN 201410276638A CN 105295050 A CN105295050 A CN 105295050A
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epoxy organosilicon
sulfonium salts
lamp
epoxy
cationic photocurable
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CN105295050B (en
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王涛
王孟强
史益忠
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Beijing University of Chemical Technology
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Abstract

The invention relates to triaryl sulfonium salts containing a silicon-oxygen chain and application thereof in photocuring epoxy resin. According to the invention, prepared (3,5-dimethyl-4-allyloxyphenyl)diphenyl sulfonium salts respectively react with hydrogen-contained siloxane so as to synthesize the triaryl sulfonium salts containing the silicon-oxygen chain. Due to good solubility in an epoxy organic silicone monomer or a prepolymer, the triaryl sulfonium salts containing the silicon-oxygen chain can be applied in a photocuring organic silicone resin system as a photosensitive initiator of the system.

Description

One class is containing silica chain triaryl sulfonium salts and apply in photo-curing epoxy resin
Technical field
The invention belongs to polymeric material field, particularly a class is containing the triaryl sulfonium salts of silica chain and the application in light-cured epoxy silicone resin thereof.。
Background technology
Silicone resin, because having excellent material property, is widely used in recent years in LED encapsulation material.Si-O key has higher ionic, and therefore organo-siloxane has the characteristic of inorganics and organic function: good heat resistance, low temperature resistant good, good weatherability (comprising wet fastness and ultraviolet aging resistance), transmitance advantages of higher.More common to the modification ratio of organo-siloxane in recent years, one of them is exactly epoxide modified organosilicon.This is because epoxy resin has excellent chemistry and physicals, be mainly manifested in: shrinking percentage, good stability, electrical insulation capability excellence that the cohesiveness of epoxy resin and a lot of material is higher, lower, physical strength is high, processibility good, good heat resistance and the advantage such as with low cost.Be widely used in the numerous areas such as coating, sizing agent, optical material, Electronic Packaging.
Modal epoxy organosilicon oxygen alkane is that hydrogen-containing siloxane and double bond containing epoxy compounds react, the epoxy organosilicon monomer obtained or organosilicon epoxy performed polymer.Such material not only can carry out thermofixation can also carry out cationic photocuring.The people such as J.V.Crivello [J.V.CrivelloandDaoshenBi.JournalofPolymerScience:PartA:P olymerChemistry, 1993,31,3121-3132] report containing oxyalkylsiloxane and epoxy monomer Si―H addition reaction, obtain the epoxy organosilicon monomer containing alkoxy-functional, with salt compounded of iodine under UV-irradiation, the strong acid of generation not only makes epoxy addition be polymerized, and make alkoxyl group generation condensation, in the couplant of polymkeric substance and filler, there is potential application, the people such as RicardoAcostaOrtiz [RicardoAcostaOrtiz, Mar é adeLourdesGuill é nCisneros, GracielaAriasGarc í a.Polymer, 2005, 46:10663 – 10671] will containing benzyl oxide group, epoxide group and 1, 1, 3, 3-tetramethyl disiloxane carries out Si―H addition reaction, obtain the epoxy organosilicon monomer of benzyl oxide class, , [RicardoAcostaOrtiz simultaneously, MarcoSangermano, RobertaBongiovanni, AidaE.GarciaValdez, LydiaBerlangaDuarte, IvonPatriciaSaucedo, AldoPriola.ProgressinOrganicCoatings, 2006, 57:159 – 164] synthesize and mixed organosilane monomer containing acrylate and epoxy, and have studied the photopolymerization of salt compounded of iodine as positively charged ion and the dual light trigger of free radical.
The key factor of the laser curing velocity of decision epoxy organosilicon oxygen performed polymer is cationic photoinitiator, the Cationic photoinitiator applied mainly contains aromatic diazo salt, diaryl group iodized salt, triaryl sulfonium salts (JamesV, Crivello.Polym.Sci.A:Polym.Chem., 1999,37 (23): 4241-4254), microcosmic salt and the luxuriant molysite compound of aryl (ThomasP.G.etal.Inorg.Chem., 1980,19:3007-3010) etc.
Along with the widespread use of silicone resin, in order to improve the intermiscibility of photoinitiator in silicone resin, in recent years, multiple organic-silicon-modified light trigger has been synthesized in research, and imparts the new function of these initiators.Polysiloxane is introduced in free radical photo-initiation and has been synthesized the novel silicon-containing polymeric photoinitiator of a class [Wang Ying, information-recording material, the 9th volume, the 1st phase in 2008] by the people such as Wang Ying.Wang Shengjie etc. have synthesized Dendritic Carbosilane Based Macrophotoinitiator [Wang Shengjie etc., polymer journal, 2006,5, (707-711)].NanZhang, the people such as FangSun utilize 4-dihydroxy benaophenonel for having synthesized a few class silicone macromolecule light trigger in light trigger basis, and its gradient polymeric is studied, [J.Mater.Chem., 2011,21 (43), 17290-17296.J.Mater.Chem., 2012,22 (18), 9166-9172.].
Above-mentioned research report is all organic-silicon-modified about radical photoinitiator, and this type of initiator can not cause epoxy organosilicon class material and carry out photocuring.And it is less about the report of organic-silicon-modified cationic photoinitiator, initiator at present for epoxy organosilicon solidification is the salt form initiator not having organosilicon chain, these initiators have immiscible property in epoxy organosilicon system, make the epoxy organosilicon system shortcoming that ubiquity laser curing velocity is slow in photocuring and photopolymerization application.
Summary of the invention
Bright object is to overcome existing cationic photoinitiator in the bad defect of cation type organic silicon epoxy systems intermiscibility, the epoxy organosilicon curing system of the cationic photocurable that a kind of initiator solvability is good is provided, in system, add the silicoorganic compound with carbazole group simultaneously, make this system have excellent laser curing velocity.
Object of the present invention is achieved through the following technical solutions:
An epoxy organosilicon curing system for cationic photocurable, is characterized in that: comprise following composition by weight:
Epoxy organosilicon performed polymer 1-100 part of cationic photocurable
Containing triaryl sulfonium salts 0.5-5 part of silica chain
Carbazole sensitizing agent 0.5-5 part
Other additive 0-10 part
The wherein said triaryl sulfonium salts containing silica chain has following general structure:
Wherein, R 1, R 2for H, CH 3, C 2h 5, n-C 3h 7, i-C 3h 7, n-C 4h 9, s-C 4h 9, t-C 4h 9, i-C 4h 9or C 6h 5;
n≥1，m≥0。
Wherein said carbazole sensitizing agent has following general structure:
Wherein m >=1, n >=0.
The structural formula of the epoxy organosilicon performed polymer of described cationic photocurable is:
Wherein n >=1
Described additive comprises one or more in solvent, white pigment, filler, defoamer, flow agent, dispersion agent.
The preparation method of the epoxy organosilicon curing system of described cationic photocurable comprises following steps: join in container by the triaryl sulfonium salts containing silica chain, then epoxy organosilicon performed polymer is added, and constantly stirring makes it mix, and obtains the cationic photocurable epoxy organosilicon curing system of homogeneous phase transparent.
The curing of the epoxy organosilicon curing system of described cationic photocurable: by applying material to be solidified on base material, then radiation curing under the cure lamp of natural light or certain illumination, can obtain cured resin after irradiating for some time.
Described cure lamp comprises low pressure mercury lamp, medium pressure mercury lamp, high voltage mercury lamp, xenon lamp, dysprosium lamp, halogen lamp, tungsten sodium lamp or laser.
The present invention has following advantage and effect relative to prior art:
In the epoxy organosilicon curing system of cationic photocurable of the present invention, initiator used is the triaryl sulfonium salts containing silica chain, and it has intermiscibility in epoxy organosilicon performed polymer; Comprise the sensitizing agent with carbazole group in the epoxy organosilicon curing system of the cationic photocurable that the present invention relates to, act synergistically with the triaryl sulfonium salts containing silica chain, photo-curing rate is improved.
Accompanying drawing explanation
Fig. 1 .(3,5-dimethyl-4-allyloxy phenyl) infrared spectra of phenylbenzene sulfosalt.
Fig. 2 .(3,5-dimethyl-4-allyloxy phenyl) proton nmr spectra of phenylbenzene sulfosalt.
The infrared spectra of Fig. 3 .TPS-SiO-1.
The proton nmr spectra of Fig. 4 .TPS-SiO-1.
The infrared spectra of Fig. 5 .TPS-SiO-2.
The proton nmr spectra of Fig. 6 .TPS-SiO-2.
The infrared spectra of Fig. 7 .TPS-SiO-3.
The proton nmr spectra of Fig. 8 .TPS-SiO-3.
The uv-visible absorption spectra of Fig. 9 .TPS-SiO-1, TPS-SiO-2, TPS-SiO-3.
Figure 10. different sorts light trigger causes the characteristic curve of Ep-SiO polymerization when fixing sensitizing agent content is 3%.
Figure 11. the TPS-SiO-3 photoinitiator of different concns under the existence of the Ep-Cz-Si of 3% to the characteristic curve of the polymerization of Ep-SiO
Figure 12. the sensitizing agent Ep-Cz-Si of different concns causes the characteristic curve of Ep-SiO polymerization when the content of fixing TPS-SiO-3 is 3%
Embodiment
Further illustrate as to of the present invention using specific examples below, but should not limit the scope of the invention with this.
Embodiment 1: the synthesis of cation light initiator TPS-SiO-1
The preparation of the first step: 1-(3,5-dimethyl-4-allyloxy) phenyl phenylbenzene sulphur hexafluorophosphate
Take 1-(3,5-dimethyl-4-hydroxyl) phenyl phenylbenzene sulphur hexafluorophosphate 9.0g (0.02mol) to add in 100mL there-necked flask, after adding 20mLTHF dissolving, add 4.1g (0.03mol) K 2cO 3stir half an hour.Add 3.2g (0.03mol) 3-bromopropylene, control temperature is 45 DEG C, by TLC point plate monitoring reaction.After completion of the reaction, decompress filter removing solid, underpressure distillation removing THF, obtains faint yellow solid.Thick product is dissolved in methylene dichloride, washes with water for several times, be transferred to by organic layer in Erlenmeyer flask, with anhydrous magnesium sulfate drying, later decompress filter, underpressure distillation, except desolventizing, obtains faint yellow solid.Productive rate is 84.1%.Through fusing point to measure fusing point for 114-117 DEG C.
Product 1h-NMR characterization data: 1h-NMR (400MHz, Acetone) δ 8.10 – 7.74 (m, 10H), 7.70 (s, 2H), 6.17 (ddd, j=22.6,10.8,5.6Hz, 1H), 5.39 (ddd, j=13.8,11.6,1.4Hz, 2H), 4.52 (d, j=5.5Hz, 2H), 2.37 (s, 6H).
Product IR (KBr) characterization data: 3091 (ν =C-H), 1576,1474,1447 (ν c=C), 836,557 (ν p-F).
Second step: the synthesis of cation light initiator TPS-SiO-1
Take 1,1,3,3-tetramethyl disiloxane 0.5g (2.00mmol) and 1-(3,5-dimethyl-4-allyloxy) phenyl phenylbenzene sulphur hexafluorophosphate 2.0g (2.06mmol) joins in 100mL tri-mouthfuls of round-bottomed flasks, add 10mL tetrahydrofuran (THF) and make (THF) solvent, two chloroplatinic acid catalysts are added after dissolving, control temperature is 60 DEG C, by TLC point plate monitoring reaction, developping agent is acetone: sherwood oil=3:2, until 1-(3,5-dimethyl-4-allyloxy) phenyl phenylbenzene sulphur hexafluorophosphate reacts completely.After completion of the reaction, steaming removing reaction solvent THF is revolved.Catalyzer is removed by column chromatography.
Product IR (KBr) characterization data: 2166 (ν si-H), 1601,1581,1477,1447 (ν c=C), 1272 (ν si-C), 1105 (ν si-O-Si), 842,580 (ν p-F).
1H-NMR characterizes: 7.25-7.85ppm is Ar-H peak on phenyl ring, 6.00-6.25,5.25-5.50 and 4.25-4.50 place-CH=CH 2peak disappears, and 2.25-2.50 is-O-CH 2-peak.
embodiment 2: the synthesis of cation light initiator TPS-SiO-2:
Identical with the preparation method of embodiment 1, just in the 4th step, 1,1,3,3-tetramethyl disiloxane, 1,3,5,7-tetramethyl-ring tetrasiloxane is replaced.
4th step is as follows:
Take 1,1,3,3-tetramethyl disiloxane 0.5g (2.00mmol) and 1-(3,5-dimethyl-4-allyloxy) phenyl phenylbenzene sulphur hexafluorophosphate 4.0g (8.12mmol) joins in 100mL tri-mouthfuls of round-bottomed flasks, add 10mL tetrahydrofuran (THF) and make (THF) solvent, two chloroplatinic acid catalysts are added after dissolving, control temperature is 60 DEG C, by TLC point plate monitoring reaction, developping agent is acetone: sherwood oil=3:2, until 1-(3,5-dimethyl-4-allyloxy) phenyl phenylbenzene sulphur hexafluorophosphate reacts completely.After completion of the reaction, steaming removing reaction solvent THF is revolved.Catalyzer is removed by column chromatography.
Product IR (KBr) characterization data: 1601,1581,1477,1447 (ν c=C), 1272 (ν si-C), 1105 (ν si-O-Si), 842 ,580 (ν p-F)..
1H-NMR characterizes: 7.25-7.85ppm is Ar-H peak on phenyl ring, 6.00-6.25,5.25-5.50 and 3.75-place-CH=CH 2peak disappears, and 2.25-2.50 is-O-CH 2-peak.
embodiment 3: the synthesis of cation light initiator TPS-SiO-3
The preparation method of embodiment 1 is identical, is just replaced by 1,1,3,3-tetramethyl disiloxane, 1,1,1,3,5,5,5-heptamethyltrisiloxane in the 4th step.
Its 4th step is as follows:
Take 1,1,1,3,5,5,5-heptamethyltrisiloxane 0.9g (4.05mmol) and 1-(3,5-dimethyl-4-allyl oxygen
Base) phenyl phenylbenzene sulphur hexafluorophosphate 2.0g (4.06mmol) joins in 100mL tri-mouthfuls of round-bottomed flasks, add 10mL tetrahydrofuran (THF) and make (THF) solvent, two chloroplatinic acid catalysts are added after dissolving, control temperature is 60 DEG C, by TLC point plate monitoring reaction, developping agent is acetone: sherwood oil=3:2, until 1-(3,5-dimethyl-4-allyloxy) phenyl phenylbenzene sulphur hexafluorophosphate reacts completely.After completion of the reaction, steaming removing reaction solvent THF is revolved.Catalyzer is removed by column chromatography.
Product IR (KBr) characterization data: 1581,1476 (ν c=C), 1259 (ν si-C),1080 (ν si-O-Si), 839,554 (ν p-F),
1H-NMR characterizes: 7.25-7.85ppm is Ar-H peak on phenyl ring, 6.00-6.25,5.25-5.50 and 4.25-4.50 place-CH=CH 2peak disappears, and 2.25-2.50 is-O-CH 2-peak.
embodiment 4: different sorts light trigger causes the characteristic curve of Ep-SiO polymerization
Characteristic curve data are recorded by gel fraction method.Gel (residue film) rate method is a kind of with the method for gravimetric determination solidification content, i.e. cured product and the weight ratio of solidifying front photosensitive system, and the relation curve of gel fraction and time shutter is characteristic curve.
Three classes contain silica chain sulfosalt as light trigger, and under the existence of the epoxy organosilicon monomer (Ep-Cz-Si) of sensitizing agent N-allyl carbazole modification, cause epoxy organosilicon (Ep-SiO) polymerization, the composition of curing system is as table 1:
(quality is mixture to be spread upon the cover glass of 1.5cm × 1.5cm with glass stick w 0 g) on, thickness is approximately 100 μm, weighs total mass in the balance to be w 1 g,at high voltage mercury lamp (wavelength 365nm place intensity of illumination I=1mW cm -2) under irradiate for some time (being specially: 5s, 10s, 20s, 30s, 40s, 60s, 100s, 160s, 220s), then soak in dehydrated alcohol and within 30 minutes, wash away the component of non-photocuring.Keep 80 DEG C afterwards in an oven till cover glass quality no longer changes, taking now quality is w 2 g,calculation formula (as follows) according to gel fraction (Gelyield):
Figure 10 illustrates light application time and gel fraction curve in embodiment 4.
The TPS-SiO-3 photoinitiator of different concns under the existence of the Ep-Cz-Si of 3% to the photobehavior of the polymerization of Ep-SiO
The composition of photocuring system is as shown in table 2:
Figure 11 illustrates light application time and gel fraction curve in embodiment 5.
embodiment 6the sensitizing agent Ep-Cz-Si of different concns causes the photobehavior experiment of Ep-SiO polymerization when the content of fixing TPS-SiO-3 is 3%
The composition of photocuring system is as shown in table 3:
Figure 12 illustrates light application time and gel fraction curve in embodiment 6.

Claims (6)

1. an epoxy organosilicon curing system for cationic photocurable, is characterized in that: comprise following composition by weight:
Epoxy organosilicon performed polymer 1-100 part of cationic photocurable
Containing triaryl sulfonium salts 0.5-5 part of silica chain
Carbazole sensitizing agent 0.5-5 part
Other additive 0-10 part
The wherein said triaryl sulfonium salts containing silica chain has following general structure:
Wherein, R 1, R 2for H, CH 3, C 2h 5, n-C 3h 7, i-C 3h 7, n-C 4h 9, s-C 4h 9, t-C 4h 9, i-C 4h 9or C 6h 5;
n≥1，m≥0。
2. the epoxy organosilicon curing system of cationic photocurable according to claim 1, is characterized in that: wherein said sensitizing agent has following general structure:
Wherein m >=1, n >=0.
3. the epoxy organosilicon curing system of cationic photocurable according to claim 1, is characterized in that:
The structural formula of the epoxy organosilicon performed polymer of described cationic photocurable is:
Wherein n >=1,
Additive comprises one or more in solvent, white pigment, filler, defoamer, flow agent, dispersion agent.
4. the preparation method of the epoxy organosilicon curing system of an a kind of cationic photocurable according to claim 1, it is characterized in that comprising following steps: the triaryl sulfonium salts containing silica chain is joined in container, then epoxy organosilicon performed polymer is added, and constantly stirring makes it mix, and obtains the cationic photocurable epoxy organosilicon curing system of homogeneous phase transparent.
5. the curing of the epoxy organosilicon curing system of a kind of cationic photocurable that one of claim 1 ~ 2 is described, it is characterized in that comprising following steps: by applying material to be solidified on base material, then radiation curing under the cure lamp of natural light or certain illumination, can obtain cured resin after irradiating for some time.
6. curing according to claim 4, is characterized in that: described cure lamp comprises low pressure mercury lamp, medium pressure mercury lamp, high voltage mercury lamp, xenon lamp, dysprosium lamp, halogen lamp, tungsten sodium lamp or laser.
CN201410276638.8A 2014-06-20 2014-06-20 A kind of triaryl sulfonium salts of chain containing silica and its applied in photo-curing epoxy resin Expired - Fee Related CN105295050B (en)

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Cited By (1)

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Publication number Priority date Publication date Assignee Title
EP3744758A1 (en) * 2019-05-31 2020-12-02 Henkel AG & Co. KGaA Onium-functionalized siloxanes

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Publication number Priority date Publication date Assignee Title
EP3744758A1 (en) * 2019-05-31 2020-12-02 Henkel AG & Co. KGaA Onium-functionalized siloxanes
WO2020239615A1 (en) * 2019-05-31 2020-12-03 Henkel Ag & Co. Kgaa Onium-functionalized siloxanes

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