CN102503868A - Novel high-refractive index resin - Google Patents
Novel high-refractive index resin Download PDFInfo
- Publication number
- CN102503868A CN102503868A CN2011103522692A CN201110352269A CN102503868A CN 102503868 A CN102503868 A CN 102503868A CN 2011103522692 A CN2011103522692 A CN 2011103522692A CN 201110352269 A CN201110352269 A CN 201110352269A CN 102503868 A CN102503868 A CN 102503868A
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- Prior art keywords
- refractive index
- novel high
- compound
- high refractive
- resin
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Abstract
The invention discloses novel high-refractive index resin. The high-refractive index resin has a structural general formula which is shown in the specification, wherein n is 1, 2 or 3; m is 0, 1, 2 or 3; and R is -H or -CH3. The resin has a high refractive index which reaches more than 1.59, and can be applied in a hardened coating made of an optical film material.
Description
Technical field
The present invention relates to a kind of improved high refractive index resins.
Background technology
The raising of phenyl ring refractive index mainly is its easy polarizability, but the increase rate of refractive index is limited, must introduce other group and just can obtain the more resin of high refractive index.Improve the effective ways of fluoropolymer resin specific refractory power and in molecular structure, introduce sulphur atom exactly, the existing lower specific density of sulphur atom, less chromatic dispersion simultaneously higher molar refraction is arranged again, so the over-all properties of thioretinite is superior to other resin.Generally introduce element sulphur with the form of thioether bond, thioester bond, sulfuryl, thiocarbamate and epithio.
Disclose a kind of application of high refractive index resins among the Japanese Patent JP2008 94987, the present invention proposes a kind of novel high refractive index resins on the high refractive index resins architecture basics.
Summary of the invention
Technical problem to be solved by this invention provides a kind of novel high refractive index resins.
For solving the problems of the technologies described above, the technical scheme that the present invention adopts is:
A kind of novel high refractive index resins, said high refractive index resins has following general structure:
In the formula: n representes 1,2 or 3, preferred 2 or 3;
M representes 0,1,2 or 3, preferred 1 or 2;
R representes-H or-CH
3
The concrete structure of said novel high refractive index resins is following:
Compound 1
Compound 2
Compound 3
Compound 4
; Or
Compound 5
Compound 6
Compared with prior art, the present invention contains the substituting group of sulphur atom through introducing, and a kind of novel high refractive index resins is provided, and the specific refractory power of resin is brought up to more than 1.59 by 1.57, and can be used for the hardening coat of optical thin film material.
Embodiment
Below in conjunction with specific embodiment the present invention is done further detailed description, but the present invention is not limited to this.
Embodiment 1
Synthesizing of compound 2:
Reaction formula:
Operation:
In 250 milliliters of there-necked flasks of whisking appliance and reflux condensing tube are housed, add 18.6 grams (0.1 mole) (A), 6.2 gram (0.11 mole) Pottasium Hydroxide, 13.75 grams (0.11 mole) (B) with 110 ml waters, stir and be heated to 100 ℃ down and reacted 1 hour; Cooling with 150 milliliters of ethyl acetate extractions twice, is told organic layer; Wash twice; Use anhydrous magnesium sulfate drying, solvent is steamed remove, obtain yellow solid (C).
Add 9.1 gram (0.12 mole) vinylformic acid, 1.7 gram Resorcinol, 130 milliliters of toluene, be heated to backflow under stirring, connect water trap and divide water outlet; Reacted 2 hours, cooling, 10% sodium chloride solution is washed once; Washing once; The toluene layer of telling is used anhydrous magnesium sulfate drying, remove toluene under reduced pressure and obtain light yellow liquid (D) 27.4 grams, yield 95.1%.
It is following to record the result with AVANCE 400 superconduction nuclear magnetic resonance spectrometers:
NMR： CDCl
3
3.00 （2H， -SCH
2-），
4.21 （2H， -CH
2O-），
5.79，6.04 （2H，-CH=CH-），
6.33 （1H， =CH-），
7.26-7.52 （9H， -A
rH），
The use Abbe refractometer records refractive index and is: 1.5975.
Embodiment 2
Synthesizing of compound 4:
Reaction formula:
。
Operation:
In 100 milliliters of there-necked flasks, add 9.3 grams (0.05 mole) (A), 3.1 gram (0.055 mole) Pottasium Hydroxide, 6.8 grams (0.055 mole) (B) with 45 ml waters, stirring and refluxing 2 hours, cooling; Extract at twice with 60 milliliters of ETHYLE ACETATE; Merge organic layer, anhydrous magnesium sulfate drying is used in washing twice behind the separatory; Remove solvent under reduced pressure, obtain yellow solid (C).Operation obtains light yellow liquid (D) 15.2 grams, yield 92.7% with embodiment 1 below.
It is following to record the result with AVANCE 400 superconduction nuclear magnetic resonance spectrometers:
NMR： CDCl
3
2.95 （2H， -SCH
2-），
3.63 （2H， -OCH
2-），
3.71 （2H， -CH
2O-），
4.33 （2H， -CH
2O-），
5.79，6.05 （2H， -CH=CH-），
6.45 （1H， =CH-），
7.17-7.48 （9H， -A
rH），
The use Abbe refractometer records refractive index and is: 1.5971.
Embodiment 3
Synthesizing of compound 5:
Reaction formula:
Operation:
100 milliliters of there-necked flasks are equipped with whisking appliance and reflux condensing tube, add 9.3 grams (0.05 mole) (A), 5.1 grams (0.055 mole) (B), 2.2 gram (0.055 mole) sodium hydroxide and 45 ml waters; Stir and to be heated to 50 ℃ of reactions 3 hours down, cool off, with twice of 50 milliliters of dichloromethane extraction; Merge organic layer; Anhydrous magnesium sulfate drying is used in washing twice, obtains faint yellow solid (C) after steaming desolventizes.
Add 4.7 gram (0.055 mole) methylacrylic acids, 0.8 gram Resorcinol and 55 milliliters of toluene, 115-120 ℃ of reflux water-dividing of heating is 4 hours under stirring, cooling, post-treating method obtains light yellow liquid (D) 14.5 grams, yield 92.9% with embodiment 1.
It is following to record the result with AVANCE 400 superconduction nuclear magnetic resonance spectrometers:
NMR： CDCl
3
1.91 （2H， -CH
2-），
1.93 （3H， -CH
3），
2.75 （2H， -SCH
2-），
4.16 （2H， -CH
2O-），
5.57，6.15 （2H， ?CH
2=），
7.08-7.49 （9H， -A
rH），
The use Abbe refractometer records refractive index and is: 1.5966.
Claims (3)
1. a novel high refractive index resins is characterized in that, said high refractive index resins has following general structure:
In the formula: n representes 1,2 or 3;
M representes 0,1,2 or 3;
R representes-H or-CH
3
2. novel high refractive index resins according to claim 1 is characterized in that said n representes 2 or 3; M representes 1 or 2.
3. novel high refractive index resins according to claim 1 and 2 is characterized in that, the concrete structure of said resin is:
Compound 1
; Or
Compound 2
Compound 3
; Or
Compound 4
Compound 5
Compound 6
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011103522692A CN102503868A (en) | 2011-11-09 | 2011-11-09 | Novel high-refractive index resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011103522692A CN102503868A (en) | 2011-11-09 | 2011-11-09 | Novel high-refractive index resin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102503868A true CN102503868A (en) | 2012-06-20 |
Family
ID=46216019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2011103522692A Pending CN102503868A (en) | 2011-11-09 | 2011-11-09 | Novel high-refractive index resin |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102503868A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105418674A (en) * | 2015-11-10 | 2016-03-23 | 中国乐凯集团有限公司 | High-refraction-rate resin and application thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11167007A (en) * | 1997-12-02 | 1999-06-22 | Seed Co Ltd | Synthetic resin lens |
| CN101095065A (en) * | 2004-12-30 | 2007-12-26 | 3M创新有限公司 | High refractive index, durable hard coats |
| JP2008094987A (en) * | 2006-10-13 | 2008-04-24 | Nippon Kayaku Co Ltd | Resin composition with high refractive index for optical material and its cured article |
| US20080200582A1 (en) * | 2007-02-20 | 2008-08-21 | Liliana Craciun | High refractive index monomers, compositions and uses thereof |
-
2011
- 2011-11-09 CN CN2011103522692A patent/CN102503868A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11167007A (en) * | 1997-12-02 | 1999-06-22 | Seed Co Ltd | Synthetic resin lens |
| CN101095065A (en) * | 2004-12-30 | 2007-12-26 | 3M创新有限公司 | High refractive index, durable hard coats |
| JP2008094987A (en) * | 2006-10-13 | 2008-04-24 | Nippon Kayaku Co Ltd | Resin composition with high refractive index for optical material and its cured article |
| US20080200582A1 (en) * | 2007-02-20 | 2008-08-21 | Liliana Craciun | High refractive index monomers, compositions and uses thereof |
Non-Patent Citations (2)
| Title |
|---|
| WEI-FANG SU等: "Thermal properties of high refractive index epoxy resin system", 《THERMOCHIMICA ACTA》, 31 December 2002 (2002-12-31), pages 385 - 389 * |
| 尹玖梅等: "一种高折光指数聚合物透明树脂的合成与性质", 《吉林大学学报(理学版)》, vol. 46, no. 3, 31 May 2008 (2008-05-31), pages 539 - 542 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105418674A (en) * | 2015-11-10 | 2016-03-23 | 中国乐凯集团有限公司 | High-refraction-rate resin and application thereof |
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| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C53 | Correction of patent of invention or patent application | ||
| CB02 | Change of applicant information |
Address after: South Street, new urban lucky 071054 Hebei province Baoding City No. 6 Applicant after: China Lucky Group Corporation Address before: 071054 Kennan street, Hebei, Baoding, No. 6 Applicant before: Chinese Lekai Film Group Co |
|
| COR | Change of bibliographic data |
Free format text: CORRECT: APPLICANT; FROM: CHINESE LEKAI FILM GROUP CO TO: CHINA LUCKY GROUP CORPORATION |
|
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20120620 |