CN101885851B - Isocyanuric ring-containing terminal hydrogenpolysiloxane - Google Patents
Isocyanuric ring-containing terminal hydrogenpolysiloxane Download PDFInfo
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Abstract
The invention relates to a hydrogenpolysiloxane, shown as the formula (1), having isocyanuric ring, and has at least two terminal hydrogensiloxy: (X are mutually independent univalence organic group not containing unsaturated bonds, R are mutually independent methyl or phenyl, n is an integer from 1 to 50, m is an integer from 0 to 5, and P is an integer from 1 to 10). As the present invention is an isocyanuric ring-containing terminal hydrogenpolysiloxane having at least two hydrogensiloxys at ends, thus it is suitable for use in optical semiconductor sealants and the like agent.
Description
Technical field
The present invention relates to a kind of organopolysiloxane, it has the hydrogen polysiloxanes part endways, can make the hardening thing of the optical characteristics such as the gas-premeables such as the electrical specifications such as thermotolerance, physical strength, electric insulating quality, water-fast vapor transmission property, the transparency, chemical-resistant, water tolerance excellence.
Background technology
Formerly, be widely used hardening silicon rubber (siliconerubber) constituent of having used the addition sclerous reaction.The weathering resistance of this kind hardening silicon rubber composition (weather resistance), thermotolerance, electric insulating quality are excellent, and the shaped materials such as cushioning material (gasketmaterial), Embedding Material (potting material), coated material (coating material), roll material (roll material), moulage (impression material), coating electric wire that is widely used as electrical/electronic part is with material and automobile part material.And, can effectively bring into play its optical characteristics and apply flexibly sealing material or solid into photosemiconductor.
Yet, this kind hardening silicon rubber composition has the peculiar siloxane bond of silicone (siloxanebond), therefore owing to there is following phenomenon in its ionic bond (ion binding property): it is using under high-temperature humidifying etc. under the extremely strict environment for use, can not bring into play for example chemical-resistant, the water tolerance of silicone, the excellent specific property of gas-premeable.And, also exist following shortcoming: the surperficial toughness of hardening thing, easily adhere to dust etc.Although it is excellent particularly to contain the polymkeric substance gas-premeable of siloxane bond, is oxygen permeable membrane (oxygen enrichment membrane) can apply flexibly, yet as semi-conductive sealing material, its steam breathability existing problems.
The present invention forms in view of the above fact, and the present inventor has carried out with keen determination research, found that the organopolysiloxane that contains the isocyanuric acid ring can make the hardening thing of above-mentioned excellent.
Polymer, polymkeric substance, the sealing agent that contains the isocyanuric acid ring be known various compounds.Known have: make the polysiloxane that contains Si-H and diallyl list glycidyl isocyanuric acid ester carry out addition reaction and the polysiloxane that contains the isocyanuric acid base carry out the compound (Japanese Patent Laid-Open 2008-143954 communique) that the ring-opening reaction sclerosis of epoxy group(ing) forms, make the polysiloxane that contains the isocyanuric acid ring and the polysiloxane that contains Si-H carry out the compound (Japanese Patent Laid-Open 2008-150506 communique) that the addition reaction sclerosis forms, make iso-cyanuric acid triallyl ester (triallylisocyanurate) and the polysiloxane that contains Si-H carry out the compound (Japanese patent laid-open 9-291214 communique) that the addition reaction sclerosis forms, make the polysiloxane that contains isocyanuric acid ring and Si-H and the compound that contains thiazolinyl carry out compound (No. 4073223 communique of Japanese Patent that the addition reaction sclerosis forms, Japanese Patent Laid-Open 2006-291044 communique, Japanese Patent Laid-Open 2007-9041 communique).
Yet the polymer that contains the isocyanuric acid ring of Japanese Patent Laid-Open 2008-143954 communique and Japanese Patent Laid-Open 2008-150506 communique contains siloxane bond in host, although therefore have flexibility poor with the intermiscibility of linking agent.
And, the polymer that contains the isocyanuric acid ring of Japanese Patent Laid-Open 2008-143954 communique and Japanese Patent Laid-Open 2008-150506 communique is because the location of thiazolinyl is uncertain, therefore be difficult to carry out addition reaction and harden, can not effectively bring into play the feature (rapidly sclerous reaction) of hydrosilation (addition reaction).The polymeric cross-linking density that contains isocyanuric acid of Japanese patent laid-open 9-291214 communique, No. 4073223 communique of Japanese Patent, Japanese Patent Laid-Open 2006-291044 communique, Japanese Patent Laid-Open 2007-9041 communique is high, upright and outspoken and lack flexibility.
These compounds are that the polysiloxane that contains the isocyanuric acid ring and the polysiloxane that contains Si-H carry out addition reaction and the hardening thing that forms, and be not that flexibility, hardening characteristics, intermiscibility are excellent, and the hardening thing of optical characteristics, water-fast vapor transmission property excellence.
This shows, above-mentioned existing hardening silicon rubber composition obviously still has inconvenience and defective, and demands urgently further being improved in product structure and use.In order to solve the problem of above-mentioned existence, relevant manufacturer there's no one who doesn't or isn't seeks solution painstakingly, but have no for a long time applicable design is finished by development always, and common product and method do not have appropriate structure and method to address the above problem, and this obviously is the problem that the anxious wish of relevant dealer solves.Therefore how to found a kind of new flexibility, hardening characteristics, intermiscibility can made excellent, and the compound of the hardening thing of optical characteristics, water-fast vapor transmission property excellence, real one of the current important research and development problem that belongs to, also becoming the current industry utmost point needs improved target.
Summary of the invention
The object of the present invention is to provide a kind of photosemiconductor that is suitable for the terminal hydrogen polysiloxanes that contains the isocyanuric acid ring in sealing agent etc.
The object of the invention to solve the technical problems realizes by the following technical solutions.For achieving the above object, according to a kind of organic hydrogen polysiloxanes of the present invention, described organic hydrogen polysiloxanes has the isocyanuric acid ring suc as formula shown in (1), and has at least 2 terminal hydrogen siloxies:
(for not containing any monovalent organic radical of unsaturated link(age), R is methyl or phenyl to X independently of each other independently of each other, and n is 1～50 integer, and m is 0～5 integer, and P is 1～10 integer).
The present invention compared with prior art has obvious advantage and beneficial effect.By technique scheme, the present invention's two ends have following advantages at least through the organopolysiloxane of monomethyl allyl group isocyanuric acid ring seal end:
The organopolysiloxane that contains the isocyanuric acid ring of the present invention has terminal hydrogen siloxy more than at least 2, therefore can react with the compound with vinyl the hardening thing of the mechanical characteristics of manufacturing organic silicone skeleton, thermotolerance, electric insulating quality, chemical-resistant, water tolerance, gas-premeable, optical characteristics excellence.This hardening thing be applicable to the LED of the essential transparency with lens or LED with the material in optical material or the particularly semi-conductive sealing materials such as sealing material.
In sum, the present invention relates to a kind of organic hydrogen polysiloxanes, described organic hydrogen polysiloxanes has the isocyanuric acid ring suc as formula shown in (1), and has at least 2 terminal hydrogen siloxies:
(for not containing any monovalent organic radical of unsaturated link(age), R is methyl or phenyl to X independently of each other independently of each other, and n is 1～50 integer, and m is 0～5 integer, and P is 1～10 integer).The present invention is owing to being a kind of terminal hydrogen polysiloxanes that contains the isocyanuric acid ring that has endways at least 2 hydrogen siloxies, thereby can be suitable for photosemiconductor with in the sealing agent etc.
Above-mentioned explanation only is the general introduction of technical solution of the present invention, for can clearer understanding technique means of the present invention, and can be implemented according to the content of specification sheets, and for above and other purpose of the present invention, feature and advantage can be become apparent, below especially exemplified by preferred embodiment, and the cooperation accompanying drawing, be described in detail as follows.
Description of drawings
Fig. 1 is the NMR spectrogram of the compound I of modulating among the embodiment.
Fig. 2 is the GPC spectrogram of the compound I of modulating among the embodiment.
Fig. 3 is the NMR spectrogram of the compound III of modulating among the embodiment.
Fig. 4 is the GPC spectrogram of the compound III of modulating among the embodiment.
Embodiment
Relevant aforementioned and other technology contents of the present invention, Characteristic can be known to present in the following detailed description that cooperates with reference to graphic preferred embodiment.By the explanation of embodiment, when can being to reach technique means and the effect that predetermined purpose takes to get one more deeply and concrete understanding to the present invention, yet appended graphic only provide with reference to the usefulness of explanation, the present invention is limited.
Organopolysiloxane of the present invention is the organopolysiloxane that contains the isocyanuric acid ring shown in the above-mentioned formula (1), it is characterized in that: have terminal hydrogen siloxy more than at least 2.
In formula (1), R is methyl or phenyl respectively independently, considers to be preferably methyl from hardening characteristics, flexibility and the synthetic easiness aspect of constituent, and preferably 50 molar percentages of all R are above is methyl.
X is not respectively independently for containing any monovalent organic radical of unsaturated link(age).X for example is alkyl, aryl, and wherein preferred carbon number is 1～4 alkyl, more preferably methyl.
N is 1～50 integer, is preferably 1～30 integer.
M is 0～5 integer, is preferably 0～2 integer.
P is 1～30 integer, is preferably 1～10 integer.
The weight average molecular weight of this organopolysiloxane is 500～10000, is preferably 600～5000.
The viscosity of this organopolysiloxane under 25 ℃ is 0.1PaS～100PaS, be preferably 0.5PaS～10PaS.
The organopolysiloxane that contains the isocyanuric acid ring of the present invention can be made by making the end shown in the diallyl isocyanuric acid ester shown in the following formula (2) and the following formula (3) carry out addition reaction through the organopolysiloxane of hydrogen siloxy (hydrogensiloxy) end-blocking.Temperature of reaction is room temperature～250 ℃, is preferably 50 ℃～180 ℃.In addition, the reaction times is 0.1 hour～120 hours, is preferably 1 hour～10 hours.
Herein, R, X, n, m are as mentioned above.
The organopolysiloxane of formula (3) is with respect to allyl group 1 equivalent, the Si-H base becomes 1.1 equivalents～2.1 equivalents, be preferably 1.1 equivalents～1.5 equivalents (the Si-H base is excessive) amount and with the compound reaction of formula (2).Can obtain to have thus the organopolysiloxane of terminal hydrogen siloxy more than at least 2.
End shown in this formula (3) for example can be enumerated following compound through the organopolysiloxane of hydrogen siloxy end-blocking.
In reaction, for example can use the compound that contains platinum, rhodium or palladium as catalyzer.The compound that wherein preferably contains platinum can use the sour hexahydrate of chlordene platinum (IV), platinum-carbonyl ethylene ylmethyl misfit thing, platinum-divinyl tetramethyl disiloxane misfit thing, platinum-cyclic vinyl methylsiloxane misfit thing, platinum-octanal/octanol misfit thing or be carried on platinum on the activated carbon.The allotment amount of catalyzer is for the compound of formula (2), and preferred contained amount of metal is 0.01ppm～10,000ppm, more preferably 0.1ppm～100ppm.
In addition, in the manufacturing of organopolysiloxane of the present invention, can in reaction mixture, add solvent.Solvent can use toluene, dimethylbenzene, sym-trimethylbenzene, diethylbenzene, tetrahydrofuran (THF), diethyl ether, Isosorbide-5-Nitrae-dioxs, phenyl ether etc.
But the compound that the organopolysiloxane illustration of utilizing aforesaid method and making is following.
The organopolysiloxane that contains the isocyanuric acid ring of the present invention can react the hardening thing of manufacturing machine characteristic, thermotolerance, electric insulating quality, chemical-resistant, water tolerance, gas-premeable, optical characteristics excellence with the compound with vinyl.This hardening thing be applicable to the LED of the essential transparency with lens or LED with the material in optical material or the particularly semi-conductive sealing materials such as sealing material.
[embodiment]
Below, with reference to example and comparative example the present invention further is illustrated, but the present invention is not limited by these embodiment.
[example 1]
With 1 of following formula (4), 1,3,3-tetramethyl disiloxane 300g (2.24 moles), toluene 300g are encased in the detachable flask (separable flask) of 2L, be heated to 80 ℃, after dripping Platinic chloride toluene solution 0.42g (platinum that contains 0.5wt%), drip the mixing solutions of monomethyl diallyl isocyanuric acid ester 250g (1.12 moles) and toluene 250g.After 8 hours, decompression is heated up in a steamer toluene and is obtained water white liquid 100 ℃ of lower stirrings.
1The result that H-NMR measures is based near crest (5.0ppm～5.4ppm, the 5.7ppm～6.0ppm) disappearance, still remaining based near the crest (4.6ppm) of Si-H proton of vinyl proton, but the allyl group of confirmation form methyl diallyl isocyanuric acid ester and above-mentioned 1 thus, 1, the Si-H radical reaction of one end of 3,3-tetramethyl disiloxane.
Resultant is the mixture of the unreacting material resultant of reaction different from the polymerization degree, according to the measurement result of GPC and NMR, can confirm to contain following formula (5) as principal constituent (being designated as " compound I ").The result that GPC measures is that weight conversion molecular weight is 1260.(P: average out to 2.9, SiH value: 3.69mmol/g, viscosity (25 ℃): 1.1PaS)
NMR, the GPC of compound I are shown among Fig. 1, Fig. 2.
NMR:JMNLA-300WB (manufacturing of JEOL company),
1H-NMR
GPC:SC-8020 (manufacturing of Tosoh company)
The viscosity of each compound is to use BM type rotational viscosimeter 25 ℃ of lower mensuration.
[example 2]
Terminal hydrogen siloxane 650g (0.89 mole), the toluene 650g of following formula (6) are encased in the detachable flask of 3L, be heated to 80 ℃, after dripping Platinic chloride toluene solution 0.84g (platinum that contains 0.5wt%), drip the mixing solutions of monomethyl diallyl isocyanuric acid ester 100g (0.44 mole) and toluene 100g.After 8 hours, decompression is heated up in a steamer toluene and is obtained water white liquid 100 ℃ of lower stirrings.
1The result that H-NMR measures is based near crest (5.0ppm～5.4ppm, the 5.7ppm～6.0ppm) disappearance, still remaining based near the crest (4.6ppm) of Si-H proton of vinyl proton, but the Si-H radical reaction of an end of the terminal hydrogen siloxane of the allyl group of confirmation form methyl diallyl isocyanuric acid ester and above-mentioned formula (6) thus.
Resultant is the mixture of the unreacting material resultant of reaction different from the polymerization degree, according to the measurement result of GPC and NMR, can confirm to contain following formula (7) as principal constituent (being designated as " compound I I ").The result that GPC measures is that weight conversion molecular weight is 2440.(P: average out to 1.8, SiH value: 0.59mmol/g, viscosity (25 ℃): 0.2PaS)
[example 3]
Terminal hydrogen siloxane 900g (2.73 moles), the toluene 900g of following formula (8) are encased in the detachable flask of 3L, be heated to 100 ℃, after dripping Platinic chloride toluene solution 0.71g (platinum that contains 0.5wt%), drip the mixing solutions of monomethyl diallyl isocyanuric acid ester 300g (1.34 moles) and toluene 300g.After 8 hours, decompression is heated up in a steamer toluene and is obtained water white liquid 100 ℃ of lower stirrings.
1The result that H-NMR measures is based near crest (5.0ppm～5.4ppm, the 5.7ppm～6.0ppm) disappearance, still remaining based near the crest (4.6ppm) of Si-H proton of vinyl proton, but the Si-H radical reaction of an end of the terminal hydrogen siloxane of the allyl group of confirmation form methyl diallyl isocyanuric acid ester and above-mentioned formula (8) thus.
Resultant is the mixture of the unreacting material resultant of reaction different from the polymerization degree, according to the measurement result of GPC and NMR, can confirm to contain following formula (9) as principal constituent (being designated as " compound III ").The result that GPC measures is that weight conversion molecular weight is 2470.(P: average out to 3.8, SiH value: 4.54mmol/g, viscosity (25 ℃): 0.4PaS)
NMR, the GPC of compound III are shown among Fig. 3, Fig. 4.
[utilizability on the industry]
The organopolysiloxane that contains the isocyanuric acid ring of the present invention has terminal hydrogen siloxy more than at least 2, therefore can react with the compound with vinyl the hardening thing of the mechanical characteristics of manufacturing organic silicone skeleton, thermotolerance, electric insulating quality, chemical-resistant, water tolerance, gas-premeable, optical characteristics excellence.This hardening thing be applicable to the LED of the essential transparency with lens or LED with the material in optical material or the particularly semi-conductive sealing materials such as sealing material.
The above, it only is preferred embodiment of the present invention, be not that the present invention is done any pro forma restriction, although the present invention discloses as above with preferred embodiment, yet be not to limit the present invention, any those skilled in the art, within not breaking away from the technical solution of the present invention scope, when the method that can utilize above-mentioned announcement and technology contents are made a little change or be modified to the equivalent embodiment of equivalent variations, in every case be the content that does not break away from technical solution of the present invention, any simple modification that foundation technical spirit of the present invention is done above embodiment, equivalent variations and modification all still belong in the scope of technical solution of the present invention.
Claims (2)
1. organic hydrogen polysiloxanes, described organic hydrogen polysiloxanes has the isocyanuric acid ring suc as formula shown in (1), and has at least 2 terminal hydrogen siloxies:
In the described formula (1), X is 1～4 alkyl independently of each other for carbon number, and R is methyl or phenyl independently of each other, and n is 1～50 integer, and m is 0～5 integer, and P is 1～10 integer.
2. organic hydrogen polysiloxanes according to claim 1, the m in the wherein said formula (1) is 1～5 integer.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009117360A JP2010265374A (en) | 2009-05-14 | 2009-05-14 | Isocyanuric ring-containing polysiloxane with terminal hydrogen |
| JP2009-117360 | 2009-05-14 |
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| CN101885851A CN101885851A (en) | 2010-11-17 |
| CN101885851B true CN101885851B (en) | 2013-05-01 |
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| JP (1) | JP2010265374A (en) |
| KR (1) | KR20100123607A (en) |
| CN (1) | CN101885851B (en) |
| TW (1) | TW201041938A (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP5933932B2 (en) * | 2011-05-06 | 2016-06-15 | 株式会社カネカ | Curable composition |
| JP5618903B2 (en) * | 2011-05-23 | 2014-11-05 | 信越化学工業株式会社 | Polymer having silphenylene structure and siloxane structure and method for producing the same |
| JP5673496B2 (en) * | 2011-11-07 | 2015-02-18 | 信越化学工業株式会社 | Resin composition, resin film, semiconductor device and manufacturing method thereof |
| EP2918638B1 (en) | 2012-11-09 | 2017-09-06 | Sumitomo Seika Chemicals Co. Ltd. | Silicone resin composition, cured silicone resin, and sealed optical semiconductor element |
| JP5716139B1 (en) | 2013-08-19 | 2015-05-13 | 住友精化株式会社 | Addition-curable silicone resin composition, addition-curable silicone resin cured product, and optical semiconductor element encapsulant |
| US9963552B2 (en) | 2013-08-20 | 2018-05-08 | Sumitomo Seika Chemicals Co., Ltd. | Condensation-curable silicone resin composition, condensation-curable silicone resin cured product, and sealed optical semiconductor element |
| JP6111174B2 (en) * | 2013-09-19 | 2017-04-05 | 四国化成工業株式会社 | Glycoluril ring-containing organosilane, glycoluril ring-containing organosiloxane and process for producing them |
| EP3245256A4 (en) * | 2015-01-13 | 2018-08-08 | Henkel AG & Co. KGaA | Organopolysiloxane prepolymer and curable organopolysiloxane composition comprising same |
| KR20210074309A (en) * | 2018-10-16 | 2021-06-21 | 신에쓰 가가꾸 고교 가부시끼가이샤 | Addition curing liquid silicone rubber composition for LED headlamps and LED headlamps |
| CN113929915B (en) * | 2021-10-26 | 2022-10-28 | 中国石油大学(华东) | Preparation method and application of modified siloxane supercritical carbon dioxide thickener |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008143954A (en) * | 2006-12-06 | 2008-06-26 | Jsr Corp | Isocyanuric ring-containing polymer, method for producing the same, and composition containing the same |
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| JP2003268251A (en) * | 2002-03-20 | 2003-09-25 | Kanegafuchi Chem Ind Co Ltd | Sealant, method for sealing semiconductor or the like, method for manufacturing semiconductor device, and semiconductor device |
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- 2010-04-29 KR KR1020100039919A patent/KR20100123607A/en not_active Application Discontinuation
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2008143954A (en) * | 2006-12-06 | 2008-06-26 | Jsr Corp | Isocyanuric ring-containing polymer, method for producing the same, and composition containing the same |
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| TW201041938A (en) | 2010-12-01 |
| CN101885851A (en) | 2010-11-17 |
| JP2010265374A (en) | 2010-11-25 |
| KR20100123607A (en) | 2010-11-24 |
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