CN1394893A - Method for preparing optical material with high refractive index by using amino polybasic thioalcohol to solidify epoxy resin - Google Patents
Method for preparing optical material with high refractive index by using amino polybasic thioalcohol to solidify epoxy resin Download PDFInfo
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- CN1394893A CN1394893A CN 02132751 CN02132751A CN1394893A CN 1394893 A CN1394893 A CN 1394893A CN 02132751 CN02132751 CN 02132751 CN 02132751 A CN02132751 A CN 02132751A CN 1394893 A CN1394893 A CN 1394893A
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Abstract
The present invention relates to a method for preparing high refractive-index optical material by using nitrogen-containing polybasic thioalcohol amine (N-methyl diethyl thioalcohol amine or triethyl thioalclhol amine) solidifying epoxy resin with high refractive index. The polybasic thioalcohol amine can be made up by using polybasic alohol amine through the processes of chlorination, sulfurization and hydrolysis reaction. Said polybasic thioalcohol amine can be used individually or can be used together with other ethylene diamine or condensed ethylenediamine solidifying agent. The refractive index of the material obtained by solidifying general bisphenol A with triethyl trialcohol amine is up to 1.6145, light transmittance is up to 90.37 and impact strength is up to 57 KJ/sq.m.
Description
Technical field:
The present invention relates to a kind of synthetic method of novel high refractive index Resins, epoxy, thereby particularly relate to a kind of method for preparing the high refractive index optical material with the thiol-cured Resins, epoxy of amino polybasic.
Technical background:
The method for preparing the optical resin of high refractive index now mainly comprises following several: (1) synthesizes the sulfur-bearing unsaturated monomer, obtains crosslinked optical resin material with the method polymerization of radical polymerization; (2) make it polymerization by equivalent after the carbimide of synthetic multi-thiol and sulfur-bearing and obtain polyisocyanate lipid optical resin material; (3) epoxy and the epithio monomer of synthetic sulfur-bearing make it curing with solidifying agent and obtain epoxy and epithio class optical resin.
In above method, the epoxy and the epithio monomer of synthetic sulfur-bearing make it to solidify the method that obtains epoxy and epithio class optical resin because heat-resisting, the chemical-resistant resistance of the resin material of preparing and good mechanical property and extremely pay attention to solidifying agent.But, only concentrate in the former research on epoxy monomer synthetic of sulfur-bearing, to the research of epoxy hardener less (Kinmura hoosin.CN1046741A, 1990), the solidifying agent that is adopted mostly is common amine.The specific refractory power of these amines is lower, and then has influenced the specific refractory power of the resin after solidifying, and the solidifying agent of therefore synthetic high refractive index is the same with the epoxy monomer of synthetic high refractive index also to be the approach of a kind of necessity of preparation high refractive index epoxies optical resin material.And can make preparation high refractive index epoxies optical resin material want simple by the solidifying agent of synthetic high refractive index.
Summary of the invention:
Purpose of the present invention just provides a kind of novel method of easy preparation high refractive index epoxies optical material.Promptly epoxy hardener and its cured epoxy resin of employing by synthetic high refractive index prepares high refractive index epoxies optical material.
Practice shows, at room temperature not only can not solidify but also the tertiary amine that must add other is done curing catalyst with common multi-thiol cured epoxy resin.And N-methyl diethyl sulfide hydramine, three sulfur alcohol amine be multi-thiol are tertiary amines simultaneously, so N-methyl diethyl sulfide hydramine, three sulfur alcohol amine cured epoxy resin at room temperature, and the higher (n of the specific refractory power of three sulfur alcohol amine
d 20Be 1.59), this is very important to the specific refractory power that improves the optical resin material after solidifying.
Though N-methyl diethyl sulfide hydramine, three sulfur alcohol amine are class known compounds, coming cured epoxy resin as solidifying agent then is a kind of brand-new purposes.
The present invention includes following three steps:
1, synthetic N-methyl diethyl sulfide hydramine, three sulfur alcohol amine;
2, solidify different types of Resins, epoxy with the synthetic N-of institute methyl diethyl sulfide hydramine, three sulfur alcohol amine
Prepare optical resin material;
3, the performance of measuring optical resin material.
N-methyl diethyl sulfide hydramine and three sulfur alcohol amine can be with the preparations of on all four method, therefore only illustrate with the preparation method of three sulfur alcohol amine below.Three sulfur alcohol amine are by step synthetic such as chlorination, sulfuration and hydrolysis by trolamine.The raw material that adopts cheaply is easy to get, and simple synthetic method is easily gone.One, the building-up reactions of three sulfur alcohol amine:
The building-up reactions of three sulfur alcohol amine comprises following three steps: the chlorination reaction of (1) trolamine
Add 163ml thionyl chloride and 150ml chloroform in the 1000ml four-hole bottle, water-bath is cooled off, and adds the chloroformic solution (300ml) of 89g (0.67mol) trolamine with dropping funnel.In 1h, dropwise, prevent to react a large amount of heat releases; Drip post-heating backflow 5h-6h, till sour gas is emitted, reacted postcooling, suction filtration gets the white needles solid.Productive rate: 86%.(2) vulcanization reaction of chloro triethanolamine salt
The product 100g that obtains is above put into the 1000ml four-hole bottle, add 96g thiocarbamide and 400ml ethanol, back flow reaction 2h, cooling back stopped reaction, the adularescent solid is separated out, and suction filtration gets white solid product (isothiuronium salts) 168g.(3) hydrolysis reaction of isothiuronium salts
The isothiuronium salts 90g that previous step is obtained puts into the 1000ml four-hole bottle, adds 120ml H
2O and 31gNaOH/160mlH
2The solution of O is at N
2Protection is heated to 80 ℃ rapidly down, and insulation reaction to most oil droplet is separated out (approximately needing 20min) and is cooled to 15 ℃ with brine bath afterwards, uses CH
2Cl
2Extract three times, use 100ml at every turn, combining extraction liquid 20g anhydrous sodium sulfate drying.Small molecules is removed in decompression.Obtain 28g colourless transparent liquid three sulfur alcohol amine, n
d=1.59 (adopting the Abbe instrument to record).In diethyl ether solution behind the preparation hydrochloric acid salify, the mixed solution recrystallization of available alcohol-ether, at last white crystal be three sulfur alcohol amine hydrochlorates, mp:82～83 ℃.The structural characterization of (4) three sulfur alcohol amine
1, in the FTIR of the three sulfur alcohol amine spectrum, 3200～3400cm
-1The hydroxyl peak at place disappears, at 2543cm
-1Sulfydryl eigen vibration peak appears in the place, and this shows that hydroxyl all is converted into sulfydryl.
2, mass spectroscopy, M/Z=197, (theoretical moleculars 197 of three sulfur alcohol amine)
3,
1The H-NMR spectrum:
Three sulfur alcohol amine hydrochlorates
1In the H-NMR spectrum, the unimodal ownership of δ=1.68ppm and the hydrogen a on the hydrochloride; δ=2.0ppm is the chemical shift of sulfydryl, and it is subjected to the effect of contiguous methylene radical, splits to be divided into triplet, Jbc=8.8; Proton hydrogen c on the methylene radical that quartet about δ=3.07ppm belongs to sulfydryl directly links to each other; Proton hydrogen d on the methylene radical that triplet belongs to nitrogen-atoms links to each other at δ=3.3ppm place.4, the results of elemental analyses of results of elemental analyses three sulfur alcohol amine hydrochlorates shows that it is consistent with theoretical value, and is as shown in the table.
The results of elemental analyses of three sulfur alcohol amine hydrochlorates
Can determine that by above analysis institute's synthetic product both had been molecules of interest three sulfur alcohol amine.Two, solidify different types of Resins, epoxy with institute's synthetic three sulfur alcohol amine
| Plain | Theoretical value | Measured value |
| ????C％ | ????30.84 | ????30.59 |
| ????H％ | ????6.42 | ????6.99 |
| ????N％ | ????6.0 | ????6.19 |
| ????S％ | ????41.11 | ????39.50 |
N-methyl diethyl sulfide hydramine, three sulfur alcohol amine energy and epoxide group reaction, this is the primary condition of cured epoxy resin, and no matter epoxide group is connected on the polyester or is connected on the polyethers, as long as there is epoxide group to exist, N-methyl diethyl sulfide hydramine, three sulfur alcohol amine can both solidify.Therefore, N-methyl diethyl sulfide hydramine, three sulfur alcohol amine can be widely used for solidifying bisphenol A type epoxy resin, aliphatic glycidyl ether based epoxy resin, phenolic Resins, epoxy and other epoxide modified polyester and polyethers resin.
Solidify the refractive index n of the material of common bisphenol a resin gained with three sulfur alcohol amine
d 20Can reach 1.6145, transmittance T% is 90.37, and shock strength IPS is 57KJ/m
2Solidify 3 with three sulfur alcohol amine, 3 '-dimercapto sulfobenzide Resins, epoxy, the refractive index n of the material of gained
d 20Be 1.67.
As seen, N-methyl diethyl sulfide hydramine, effect such as three sulfur alcohol amine are used as solidifying agent, have applied range, and solidification effect is good.
Embodiment:
N-methyl diethyl sulfide hydramine, the condition of three sulfur alcohol amine curing various types of resins is similar substantially, the condition of three sulfur alcohol amine being solidified various types of resins is described in detail below by enforcement, and the condition of N-methyl diethyl sulfide hydramine curing various types of resins is only done simple explanation
Embodiment one: with three sulfur alcohol amine cured epoxy 618 resins (DGEBA)
After three sulfur alcohol amine and 618 epoxy resin mixed by equivalent, vacuumize degassing was injected the glass mold (sheet glass will be handled with releasing agent) that accompanies plastics tubing to there not being bubble under 40 ℃ of conditions; Put into baking oven then, solidify 0.5h at 60 ℃, 80 ℃ solidify 4h, rise to 120 ℃ with 10 ℃/20min speed then and solidify 1h, and curing is closed baking oven after finishing, the straight room temperature of naturally cooling, and the demoulding promptly gets resin plate.The resin plate that obtains is carried out performance characterization obtain following table;
The performance of 618 epoxy resin/three sulfur alcohol amine cured resins
| ????n d 20 | ????ν d | ????ρ ????g/cm 3 | ????Rwa ????wt％ | ??IPS ??kJ/m 2 | ??hard | ???T％ ???550nm | ??Y | ?US ?nm | ?Tg |
| ??1.6145 | ??36.0 | ??1.2250 | ??0.2538 | ????57 | ??HB | ???90.37 | ??0.071 | ?314 | ??44.7 |
In table: n
d 20Be specific refractory power; ν
dBe Abbe number; ρ density; The water-intake rate of Rwa sample; IPS is a shock strength; Hard is the surface hardness (pencil hardness) of sample; T% is a transmittance; US is the ultraviolet cut-on wavelength; T
gBe second-order transition temperature; Below each the table in symbolic significance identical.
Embodiment two:
Three sulfur alcohol amine can also mix use with other solidifying agent, can regulate the performance of solidifying the back resin by adding other solidifying agent.We adopt three sulfur alcohol amine and quadrol mixed curing agent to solidify the T that 618 Resins, epoxy improve the material after the curing
gQuadrol similar with the performance of the ethylenediamines that contracts they can do mixed curing agent and use, the quadrol and the quadrol that contracts can exchange in use.
Here the total amount of solidifying agent and Resins, epoxy are equivalent, and the percentage ratio that accounts for total solidifying agent with quadrol calculates the consumption of quadrol.
After mixing by equivalent with 618 epoxy resin after three sulfur alcohol amine and quadrol mixed according to a certain ratio, vacuumize degassing is injected the glass mold (sheet glass will be handled with releasing agent) that accompanies plastics tubing to there not being bubble at ambient temperature again; Put into baking oven then, solidify 0.5h at 60 ℃, 80 ℃ solidify 4h, rise to 120 ℃ with 10 ℃/20min speed then and solidify 1h, and curing is closed baking oven after finishing, the straight room temperature of naturally cooling, and the demoulding promptly gets resin plate.The resin plate that obtains is carried out performance characterization obtains following table:
The performance of 618 epoxy resin resin behind three sulfur alcohol amine and quadrol co-curing
| Quadrol equivalent % | ???n d 20 | ???ν d | ????ρ ??g/cm 3 | ??Rwa ??wt％ | ????IPS ???kJ/m 2 | ?hard | ??T％ ??550nm | ????Y | ??US ??nm | ??Tg |
| ??5％ | ??1.6129 | ??35.7 | ??1.2239 | ?0.2324 | ????- | ??HB. | ??87.82 | ??0.011 | ??313.5 | |
| ??10％ | ??1.6117 | ??35.5 | ??1.2211 | ?0.1986 | ????53 | ??HB | ??88.56 | ??0.010 | ??303 | |
| ??20％ | ??1.6105 | ??35.4 | ??1.2195 | ?0.1896 | ????31 | ??HB | ??95.87 | ??0.068 | ??304 | ??61.5 |
| ??40％ | ??1.6040 | ??34.8 | ??1.2105 | ??0.1421 | ????- | ??H | ??82.35 | ??0.134 | ??304.5 |
Embodiment three:
Solidify 3 with three sulfur alcohol amine, 3 '-dimercapto sulfobenzide Resins, epoxy.With three sulfur alcohol amine and 3, after 3 '-dimercapto sulfobenzide Resins, epoxy mixed by equivalent, vacuumize degassing was injected the glass mold (sheet glass will be handled with releasing agent) that accompanies plastics tubing to there not being bubble at ambient temperature; Put into baking oven then, solidify 0.5h at 60 ℃, 80 ℃ solidify 4h, rise to 120 ℃ with 10 ℃/20min speed then and solidify 1h, and curing is closed baking oven after finishing, the straight room temperature of naturally cooling, and the demoulding promptly gets resin plate.The resin plate that obtains is carried out performance characterization obtain following table.
3, the performance of 3 '-dimercapto sulfobenzide Resins, epoxy/three sulfur alcohol amine co-curing systems
| ??n d 20 | ν d | ??ρg/cm 3 | ??Rwa ??wt％ | ?hard | ??T％ ??550nm | ??Y | ??US ??nm |
| ??1.67 | ?29 | ??1.3799 | ?0.457 | ?HB | ??76.7 | ??0.383 | ??359.0 |
Embodiment four:
Solidify 3 with three sulfur alcohol amine, 3 '-dimercapto sulfobenzide Resins, epoxy and 618 Resins, epoxy, the performance that can regulate cured product with the mixture of the different Resins, epoxy of three sulfur alcohol amine curing is to adapt to different needs.Here the percentage ratio that accounts for the total yield of Resins, epoxy with 618 Resins, epoxy calculates the content of 618 Resins, epoxy.
With 3, after mixing, 3 '-dimercapto sulfobenzide Resins, epoxy and 618 Resins, epoxy mix with three sulfur alcohol amine of equivalent again, vacuumize degassing is injected the glass mold (sheet glass will be handled with releasing agent) that accompanies plastics tubing to there not being bubble at ambient temperature; Put into baking oven then, solidify 0.5h at 60 ℃, 80 ℃ solidify 4h, rise to 120 ℃ with 10 ℃/20min speed then and solidify 1h, and curing is closed baking oven after finishing, the straight room temperature of naturally cooling, and the demoulding promptly gets resin plate.The resin plate that obtains is carried out performance characterization obtains following table:
3,3 '-dimercapto sulfobenzide Resins, epoxy and 618 epoxy resin hybrid resin
The performance of system behind three sulfur alcohol amine co-curings
| ??DGEBA ??wt％ | ????n d 20 | ??ν d | ??ρ ??g/cm 3 | ??Rwa ??wt％ | ??hard | ??T％ ??550nm | ????Y | ???US ???nm |
| ??0％ | ???1.67 | ??29 | ??1.3799 | ??0.457 | ??HB | ??76.7 | ??0.383 | ??359.0 |
| ??10％ | ???1.665 | ??30.5 | ??1.3598 | ??0.748 | ??H | ??85.5 | ??0.3012 | ??358.0 |
| ??30％ | ???1.655 | ??31.7 | ??1.3183 | ??0.563 | ??H | ??84.6 | ??0.1809 | ??357.5 |
| ??50％ | ???1.645 | ??32.8 | ??1.2962 | ??0.573 | ??2H | ??82.4 | ??0.1191 | ??355.0 |
| ??70％ | ???1.631 | ??34.0 | ??1.2771 | ??0.628 | ??2H | ??81.5 | ??0.1241 | ??354.0 |
| ??100％ | ???1.6145 | ??36.0 | ??1.2250 | ??0.2538 | ??HB | ??90.37 | ??0.071 | ??314 |
Embodiment five:
Solidify 618 Resins, epoxy with N-methyl diethyl sulfide hydramine.After N-methyl diethyl sulfide hydramine and 618 Resins, epoxy were mixed by equivalent, vacuumize degassing was injected the glass mold (sheet glass will be handled with releasing agent) that accompanies plastics tubing to there not being bubble at ambient temperature; Put into baking oven then, solidify 0.5h at 60 ℃, 80 ℃ solidify 4h, rise to 120 ℃ with 10 ℃/20min speed then and solidify 1h, and curing is closed baking oven after finishing, the straight room temperature of naturally cooling, and the demoulding promptly gets resin plate.The resin plate that obtains is carried out performance characterization obtain following table.
The performance of 618 epoxy resin/N-methyl diethyl sulfide hydramine cured resin
| ??n d 20 | ??ν d | ????ρ ???g/cm 3 | ??Rwa ??wt％ | ??IPS ??kJ/m 2 | ??hard | ???T％ ???550nm |
| ??1.6015 | ??39.0 | ??1.2123 | ??0.2538 | ???59 | ???HB | ???91.37 |
Claims (7)
1, a kind of method for preparing the high refractive index optical material with the thiol-cured Resins, epoxy of amino polybasic, comprise the synthetic of multi-thiol amine hardener, two steps of multi-thiol epoxy-amine resin, it is characterized in that: with polyhydric alcohol amine through chlorination, the multi-thiol amine that makes after sulfuration and the hydrolysis reaction step is as solidifying agent, after mixing by equivalent with Resins, epoxy, vacuumize degassing is to there not being bubble under 40 ℃ of conditions, injection accompanies the glass mold through the releasing agent processing of plastics tubing, put into baking oven then, solidify 0.5h at 60 ℃, 80 ℃ solidify 4h, rise to 120 ℃ with 10 ℃/20min speed then and solidify 1h, close baking oven after solidifying end, the straight room temperature of naturally cooling, the demoulding promptly gets high refractive index optical resin sheet material.
2, the method for preparing the high refractive index optical material with the thiol-cured Resins, epoxy of amino polybasic as claimed in claim 1, it is characterized in that: multi-thiol amine can also be used for cured epoxy resin with other solidifying agent composition mixed curing agent and prepare the high refractive index optical material, mixed curing agent and Resins, epoxy equivalent.
3, as claimed in claim 1 or 2ly prepare the method for high refractive index optical material with the thiol-cured Resins, epoxy of amino polybasic, it is characterized in that: the multi-thiol amine hardener can be N-methyl diethyl sulfide hydramine or three sulfur alcohol amine.
4, as claimed in claim 1 or 2ly prepare the method for high refractive index optical material with the thiol-cured Resins, epoxy of amino polybasic, it is characterized in that: available multi-thiol amine solidified Resins, epoxy comprises bisphenol A type epoxy resin, aliphatic glycidyl ether based epoxy resin, phenolic Resins, epoxy or other epoxide modified polyester and polyethers resin.
5, as claimed in claim 3ly prepare the method for high refractive index optical material with the thiol-cured Resins, epoxy of amino polybasic, it is characterized in that: available multi-thiol amine solidified Resins, epoxy comprises bisphenol A type epoxy resin, aliphatic glycidyl ether based epoxy resin, phenolic Resins, epoxy or other epoxide modified polyester and polyethers resin.
6, as claimed in claim 2ly prepare the method for high refractive index optical material with the thiol-cured Resins, epoxy of amino polybasic, it is characterized in that: employed other solidifying agent can be the quadrol or the ethylenediamines solidifying agent that contracts in the mixed curing agent that multi-thiol amine and other solidifying agent are formed.
7, as claimed in claim 6ly prepare the method for high refractive index optical material with the thiol-cured Resins, epoxy of amino polybasic, it is characterized in that: available multi-thiol amine solidified Resins, epoxy comprises bisphenol A type epoxy resin, aliphatic glycidyl ether based epoxy resin, phenolic Resins, epoxy or other epoxide modified polyester and polyethers resin.
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| CNB021327513A CN1166717C (en) | 2002-08-08 | 2002-08-08 | Method for preparing optical material with high refractive index by using amino polybasic thioalcohol to solidify epoxy resin |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103278880A (en) * | 2013-06-26 | 2013-09-04 | 涌德电子股份有限公司 | Light guiding body and manufacturing method thereof |
| CN103345015A (en) * | 2013-06-26 | 2013-10-09 | 涌德电子股份有限公司 | Light guiding body structure and manufacturing method thereof |
| CN105368269A (en) * | 2014-08-26 | 2016-03-02 | 中国石油天然气集团公司 | Low-temperature-cured liquid-state anticorrosive epoxy resin coating and preparation method thereof |
| CN106279289A (en) * | 2016-08-11 | 2017-01-04 | 江苏华天通科技有限公司 | A kind of sulfur-containing epoxy resin monomer, optical resin material and preparation method thereof |
| CN110343495A (en) * | 2019-08-13 | 2019-10-18 | 山东益丰生化环保股份有限公司 | A kind of epoxy resin adhesive and preparation method thereof |
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2002
- 2002-08-08 CN CNB021327513A patent/CN1166717C/en not_active Expired - Fee Related
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103278880A (en) * | 2013-06-26 | 2013-09-04 | 涌德电子股份有限公司 | Light guiding body and manufacturing method thereof |
| CN103345015A (en) * | 2013-06-26 | 2013-10-09 | 涌德电子股份有限公司 | Light guiding body structure and manufacturing method thereof |
| CN103345015B (en) * | 2013-06-26 | 2016-01-20 | 东莞建冠塑胶电子有限公司 | A kind of guide structure and preparation method thereof |
| CN105368269A (en) * | 2014-08-26 | 2016-03-02 | 中国石油天然气集团公司 | Low-temperature-cured liquid-state anticorrosive epoxy resin coating and preparation method thereof |
| CN105368269B (en) * | 2014-08-26 | 2017-09-01 | 中国石油天然气集团公司 | A kind of low-temperature setting liquid-state epoxy resin anticorrosive coating and its manufacture method |
| CN106279289A (en) * | 2016-08-11 | 2017-01-04 | 江苏华天通科技有限公司 | A kind of sulfur-containing epoxy resin monomer, optical resin material and preparation method thereof |
| CN106279289B (en) * | 2016-08-11 | 2019-05-24 | 江苏华天通科技有限公司 | A kind of sulfur-containing epoxy resin monomer, optical resin material and preparation method thereof |
| CN110343495A (en) * | 2019-08-13 | 2019-10-18 | 山东益丰生化环保股份有限公司 | A kind of epoxy resin adhesive and preparation method thereof |
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|---|---|
| CN1166717C (en) | 2004-09-15 |
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