CN101798263A - Method for preparing unsaturated adamantane ester - Google Patents
Method for preparing unsaturated adamantane ester Download PDFInfo
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- CN101798263A CN101798263A CN 201010151328 CN201010151328A CN101798263A CN 101798263 A CN101798263 A CN 101798263A CN 201010151328 CN201010151328 CN 201010151328 CN 201010151328 A CN201010151328 A CN 201010151328A CN 101798263 A CN101798263 A CN 101798263A
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Abstract
The invention relates to a method for preparing unsaturated adamantane-base ester, comprising the following steps: adding and stirring adamantane alcohol and tertiary amine to organic solvent; dissolving unsaturated acyl chloride in the organic solvent to obtain organic unsaturated acyl chloride solution; dropwise adding the organic unsaturated acyl chloride solution to a three-neck flask in 3h; after finishing adding the organic unsaturated acyl chloride solution, continuously stirring reaction solution for 5 h, and making the reaction solution react at 0-5 DEG C; filtering the organic unsaturated acyl chloride solution, washing, drying and steaming rotationally to obtain the unsaturated adamantane ester. The monomer can be used as the structural unit for preparing photoresist main resin so as to improve the corrosion resistance of the photoresist main resin and can be also used as the active diluent for preparing photo-cured coating. The method for preparing the unsaturated adamantane-base ester ensures that the experimental step is simple, the reaction process is easy to control, the possibility of generating the byproduct can be reduced, thereby being easy to realize the industrialization.
Description
Technical field
The invention belongs to field of light-sensitive high molecular materials, be specifically related to a kind of preparation method of adamantyl unsaturated ester.
Background technology
Photoresist material is the key chemical materials of producing in the unicircuit Micrometer-Nanometer Processing Technology.Photoresist material claims photo-resist again, the photosensitive mixing liquid of being made up of photosensitive resin, sensitizing agent and three kinds of main components of solvent.Photocuring reaction can take place at exposure region in photosensitive resin soon after illumination, make the physicals, particularly solvability, affinity etc. of this material that considerable change take place.Handle through appropriate solvent, the molten soluble fractions that goes obtains required image.According to its chemical reaction mechanism and development principle, can be divided into negative photoresist and positive photoresist two classes.The imaging resolution of photoresist material and exposure wavelength, exposure machine lens openings number are inversely proportional to, and are the main paties that improves resolving power so shorten exposure wavelength.Along with the needs of the research and the production of nano level unicircuit, photoetching process has experienced from G line (436nm) photoetching, I line (365nm) photoetching, to deep ultraviolet 248nm photoetching, and the development course of present 193nm photoetching.
Early stage 193nm photoresist material uses poly-(methyl) acrylate derivative as matrix resin, mainly be since its at 193nm transparency height, the resolving power height, synthesis technique is simple, expense is cheap.But (low C/H than) anti-dry etching is poor because the linear structure of its main chain, though introduced the alicyclic ring hydrocarbon afterwards on its side chain, makes its corrosion stability obtain large increase, and its corrosion stability is compared with traditional resin certain gap.Owing on side chain, introduced very a high proportion of alicyclic ring, caused the hydrophobicity of polymkeric substance too big, with the poor adhesion of substrate; After another shortcoming was etching, the patterned surface roughness was big.Resistance so that adamantane esters is made as raw material is widely used owing to dry etching patience is high.
People such as Isaac O.Donkor have studied (Bioorganic ﹠amp; MedicinalChemistry, 1998 (6): the 563-568) preparation method of adamantyl acetyl triethyl and adamantyl ethyl ester.People such as D.Briers have studied (Polymer, 2004 (45): 19-24) have the polymkeric substance and the correlated performance thereof of adamantyl metacrylic acid ester structure.People such as Hui Chuan (photographic science and photochemistry, 2007 (25): 357-363) utilize 2-Buddha's warrior attendant ketone,, synthesized methacrylic acid (2-methyl-2-diamantane) ester and methacrylic acid (2-ethyl-2-diamantane) ester by grignard reaction, esterification.Lou Jie waits the people to study (Anhui chemical industry, 2009 (35): the 29-30) synthetic method of (methyl) vinylformic acid diamantane methyl alcohol ester clearly.Chinese patent CN1429195A (open day: a kind of alkylating reagent that is made of organometallic compound is disclosed to the diamantane ketoalkylation 2003.7.9), then with the metal alkyl alkoxide that obtains by chloride thing esterification method.Chinese patent CN1527810A (open day: 2004.9.8) disclose a kind of alkylating reagent that constitutes by organometallic compound, adopted the preparation method of carboxylic acid then to the esterification of adamantyl alkoxide cpd to the diamantane ketoalkylation.Chinese patent CN1444557A (open day: 2003.9.24) disclose a kind of in the presence of acid catalyst the preparation method of adamantanol and carboxylic acid cpd prepared in reaction adamantane esters.Chinese patent CN1678646A (open day: 2005.10.5) disclose a kind of fluorinated polymer that in photo-resist and microplate print process, uses, comprised vinylformic acid hydroxyadamantane ester in the structural unit of polymkeric substance.
More than these methods have following shortcoming: 1, reactions steps is more, is easy to generate by product, and its result makes the yield of object ester significantly reduce; 2, the restriction of the usage quantity of acyl chlorides is bigger, and the easy hydrolysis of unnecessary acyl chlorides produces acid, and the adamantane esters that acid can cause generating decomposes, thereby reduces productive rate.3, do not have under the condition of existence of other any additives, use under the situation of adamantanol as raw material of tertiary alcohols, the dehydration reaction of alcohol preferentially takes place, and makes the yield of product adamantane esters obviously reduce.4, experiment condition is more loaded down with trivial details, is difficult to control, is unfavorable for scale operation.
Summary of the invention
The objective of the invention is to solve the problems of the prior art, provide the possibility that a kind of synthesis step is few, by product appears in reduction, the monomeric preparation method of simple function group unsaturated ester.
The preparation method of adamantyl unsaturated ester provided by the invention, this unsaturated ester monomer can be used as the structural unit of preparation photoresist material matrix resin, is used to improve corrosion stability.Also can be used as reactive thinner, be used to prepare the light solidifying coating material.
General structure is as follows:
In the formula, R
1A kind of in hydrogen atom, the methyl; R
2A kind of in hydrogen atom, hydroxyl, the amido; R
3, R
4A kind of in hydrogen atom, acid chloride group, the methyl; R
1' be a kind of in hydrogen atom, the methyl; R
2' be a kind of in hydrogen atom, methyl, the ethyl; R
3', R
4' be a kind of in hydrogen atom, acid chloride group, the methyl.
1, a kind of synthetic method that is used to prepare photoresist material matrix resin adamantyl unsaturated ester is characterized in that may further comprise the steps:
(1) adamantanol is dissolved in the organic solvent, joins in the there-necked flask simultaneously with tertiary amine and stir, wherein the mol ratio of adamantanol and tertiary amine is 1: 1～3;
(2) unsaturated acyl chlorides is dissolved in obtains unsaturated acyl chlorides organic solution in the organic solvent, in there-necked flask, drip this unsaturated acyl chlorides organic solution in 3 hours, after dropwising, reaction solution continues to stir 5 hours, temperature of reaction is 0-5 ℃, and wherein the mol ratio of adamantanol and acyl chlorides is 1: 1～2;
(3) above-mentioned solution is carried out suction filtration, washing then, dry, rotary evaporation promptly get the adamantyl unsaturated ester monomer.
2, method according to claim 1, it is characterized in that, adamantanol described in the step (1) is 1-adamantanol, 2-adamantanol, 2-methyl-2-adamantanol, 2-ethyl-2-adamantanol, 3-amido-1-adamantanol, 1, a kind of in 3-two adamantanols.
3, method according to claim 1 is characterized in that, the tertiary amine described in the step (1) is a kind of in triethylamine, tripropyl amine, tri-isopropyl amine, the tri-n-butylamine.
4, method according to claim 1 is characterized in that, the organic solvent described in the step (1) is a kind of in benzene,toluene,xylene, methylene dichloride, the trichloromethane.
5, method according to claim 1 is characterized in that, the unsaturated acyl chlorides described in the step (2) is acrylate chloride, methacrylic chloride, maleic chloride, 2-butylene acyl chlorides, 3, a kind of in the 3-dimethyl acryloyl chloride.
6, method according to claim 1 is characterized in that, solution suction filtration, washing after reaction is finished described in the step (3), and wherein washing process is used 1mol/LHCl solution, 1mol/L NaHCO respectively
3Solution, deionized water wash three times.
Compared with prior art, the present invention has the following advantages:
1, the preparation method of adamantyl unsaturated ester provided by the invention has simplified synthesis step, avoids generating in reaction multiple by product.
2, added the tertiary amine compound among the preparation method of adamantyl unsaturated ester provided by the invention, make the chloride compounds of reaction system activate, transformation efficiency improves, and the use mol ratio of chloride compounds can be changed in very wide scope, also can suppress product effectively and decompose.
3, the preparation method of adamantyl unsaturated ester provided by the invention has added the catalyzer tertiary amine, can avoid taking place the dehydration reaction of alcohol.
4, the present invention uses acyl chloride reaction to synthesize target product, and experimental technique is easy, and speed of response is fast, and the reaction process easy handling helps this Product industrialization.
Description of drawings
The infrared spectrum of the 2-adamantyl acrylate of Fig. 1, embodiment 1 preparation.
The nuclear magnetic spectrogram of the 2-adamantyl acrylate of Fig. 2, embodiment 1 preparation.
Embodiment
Embodiment 1
The preparation of 2-adamantyl acrylate
After together adding 5g 2-adamantanol, 5g triethylamine and 100mL toluene in the there-necked flask that has mechanical stirring device, temperature of reaction is 2 ℃, and take by weighing the 3.6g acrylate chloride, and it is dissolved in the 40mL toluene again, in 3 hours, splash in the there-necked flask, after dropwising, continue to stir standing over night, suction filtration 5 hours, obtain light yellow liquid, use dilute hydrochloric acid solution (1mol/L), NaHCO successively
3(1mol/L) behind solution and the distilled water wash light yellow liquid (retaining liquid is upper strata liquid), use anhydrous Na
2SO
4Drying is filtered, and rotary evaporation removes and desolvates, and obtains the light yellow 2-adamantyl of 3.5g acrylate liquid (productive rate is 51.7%), and its structural formula is as follows
Embodiment 2
The preparation of 1-adamantyl acrylate
After together adding 5g 1-adamantanol, 5g triethylamine and 100mL toluene in the there-necked flask that has mechanical stirring device, temperature of reaction is 3 ℃, and take by weighing the 3.6g acrylate chloride, and it is dissolved in the 40mL toluene again, in 3 hours, splash in the there-necked flask, after dropwising, continue to stir standing over night, suction filtration 5 hours, obtain light yellow liquid, use dilute hydrochloric acid solution (1mol/L), NaHCO successively
3(1mol/L) behind solution and the distilled water wash light yellow liquid (retaining liquid is upper strata liquid), use anhydrous Na
2SO
4Drying is filtered, and rotary evaporation removes and desolvates, and obtains the light yellow 1-adamantyl of 3.3g acrylate liquid (productive rate is 48.7%), and its structural formula is as follows
Embodiment 3
The preparation of 2-adamantyl methacrylic ester
After together adding 5g 2-adamantanol, 14g tripropyl amine and 200mL benzene in the there-necked flask that has mechanical stirring device, temperature of reaction is 2 ℃, and take by weighing the 6.9g methacrylic chloride, and it is dissolved in the 60mL benzene again, in 3 hours, splash in the there-necked flask, after dropwising, continue to stir standing over night, suction filtration 5 hours, obtain light yellow liquid, use dilute hydrochloric acid solution (1mol/L), NaHCO successively
3(1mol/L) behind solution and the distilled water wash light yellow liquid (retaining liquid is upper strata liquid), use anhydrous Na
2SO
4Drying is filtered, and rotary evaporation removes and desolvates, and obtains light yellow 3.8g 2-adamantyl methacrylic ester liquid (productive rate is 52%), and its structural formula is as follows
Embodiment 4
The preparation of 2-ethyl-2-adamantyl methacrylic ester
After together adding 5g 2-ethyl-2-adamantanol, 6.6g tri-n-butylamine and 100mL trichloromethane in the there-necked flask that has mechanical stirring device, temperature of reaction is 5 ℃, and take by weighing the 2g methacrylic chloride, and it is dissolved in the 30mL trichloromethane again, in 3 hours, splash in the there-necked flask, after dropwising, continue to stir standing over night, suction filtration 5 hours, obtain light yellow liquid, use dilute hydrochloric acid solution (1mol/L), NaHCO successively
3(1mol/L) behind solution and the distilled water wash light yellow liquid (retaining liquid is subnatant), use anhydrous Na
2SO
4Drying is filtered, and rotary evaporation removes and desolvates, and obtains the light yellow 2-ethyl of 3g-2-adamantyl methacrylic ester liquid (productive rate is 49%), and its structural formula is as follows
Embodiment 5
The preparation of (2-methyl 2-adamantyl) 2-butylene acid esters
After together adding 5g 2-methyl-2-adamantanol, 2g triethylamine and 100mL dimethylbenzene in the there-necked flask that has mechanical stirring device, temperature of reaction is 4 ℃, and take by weighing 2g 2-butylene acyl chlorides, and it is dissolved in the 30mL dimethylbenzene again, in 3 hours, splash in the there-necked flask, after dropwising, continue to stir standing over night, suction filtration 5 hours, obtain light yellow liquid, use dilute hydrochloric acid solution (1mol/L), NaHCO successively
3(1mol/L) behind solution and the distilled water wash light yellow liquid (retaining liquid is upper strata liquid), use anhydrous Na
2SO
4Drying is filtered, and rotary evaporation removes and desolvates, and obtains the light yellow 2-of 3g (2-methyl 2-adamantyl) crotonate liquid (productive rate is 48%), and its structural formula is as follows
Embodiment 6
(2-adamantyl) 3, the preparation of 3-dimethacrylate
After together adding 5g 2-adamantanol, 9.4g tripropyl amine and 150mL methylene dichloride in the there-necked flask that has mechanical stirring device, temperature of reaction is 2 ℃, and takes by weighing 4g 3, the 3-dimethyl acryloyl chloride, it is dissolved in the 50mL methylene dichloride again, in 3 hours, splash in the there-necked flask, after dropwising, continue to stir 5 hours, standing over night, suction filtration obtains light yellow liquid, uses dilute hydrochloric acid solution (1mol/L), NaHCO successively
3(1mol/L) and distilled water wash light yellow liquid (retaining liquid is subnatant) after, use anhydrous Na
2SO
4Drying is filtered, and rotary evaporation removes and desolvates, and obtains light yellow (the 2-adamantyl) 3 of 3.9g, 3-dimethacrylate liquid (productive rate is 51%), and its structural formula is as follows
Embodiment 7
The preparation of (3-hydroxyl-1-adamantyl) 2-butylene acid esters
With 5g 1, after 3-two adamantanols, 6g triethylamine and 100mL benzene together added in the there-necked flask that has mechanical stirring device, temperature of reaction was 2 ℃, and took by weighing 3.7g 2-butylene acyl chlorides, it is dissolved in the 40mL benzene again, in 3 hours, splash in the there-necked flask, after dropwising, continue to stir 5 hours, standing over night, suction filtration obtains light yellow liquid, uses dilute hydrochloric acid solution (1mol/L), NaHCO successively
3(1mol/L) and distilled water wash light yellow liquid (retaining liquid is upper strata liquid) after, use anhydrous Na
2SO
4Drying is filtered, and rotary evaporation removes and desolvates, and obtains 3.5g light yellow (3-hydroxyl-1-adamantyl) 2-butylene acid esters liquid (productive rate is 50%), and its structural formula is as follows
Embodiment 8
The preparation of (2-adamantyl) 2-butylene acid esters
After together adding 5g 2-adamantanol, 9g tri-n-butylamine and 150mL trichloromethane in the there-necked flask that has mechanical stirring device, temperature of reaction is 3 ℃, and take by weighing 4.1g 2-butylene acyl chlorides, and it is dissolved in the 50mL trichloromethane again, in 3 hours, splash in the there-necked flask, after dropwising, continue to stir standing over night, suction filtration 5 hours, obtain light yellow liquid, use dilute hydrochloric acid solution (1mol/L), NaHCO successively
3(1mol/L) and distilled water wash light yellow liquid (retaining liquid is subnatant) after, use anhydrous Na
2SO
4Drying is filtered, and rotary evaporation removes and desolvates, and obtains 3.5g light yellow (2-adamantyl) 2-butylene acid esters liquid (productive rate is 48%), and its structural formula is as follows
Embodiment 9
The preparation of 3-amido-1-adamantyl acrylate
After together adding 5g 3-amido-1-adamantanol, 6.4g tripropyl amine and 100mL toluene in the there-necked flask that has mechanical stirring device, temperature of reaction is 2 ℃, and take by weighing the 3.3g acrylate chloride, and it is dissolved in the 40mL toluene again, in 3 hours, splash in the there-necked flask, after dropwising, continue to stir standing over night, suction filtration 5 hours, obtain light yellow liquid, use dilute hydrochloric acid solution (1mol/L), NaHCO successively
3(1mol/L) and distilled water wash light yellow liquid (retaining liquid is upper strata liquid) after, use anhydrous Na
2SO
4Drying is filtered, and rotary evaporation removes and desolvates, and obtains the light yellow 3-amido of 3.1g-1-adamantyl acrylate liquid (productive rate is 47%), and its structural formula is as follows
Embodiment 10
The preparation of butene dioic acid two diamantane-2-alcohol ester
After together adding 5g 2-adamantanol, 18g tri-n-butylamine and 200mL trichloromethane in the there-necked flask that has mechanical stirring device, temperature of reaction is 0 ℃, and take by weighing the 5g maleic chloride, and it is dissolved in the 50mL trichloromethane again, in 3 hours, splash in the there-necked flask, after dropwising, continue to stir standing over night, suction filtration 5 hours, obtain light yellow liquid, use dilute hydrochloric acid solution (1mol/L), NaHCO successively
3(1mol/L) and distilled water wash light yellow liquid (retaining liquid is subnatant) after, use anhydrous Na
2SO
4Drying is filtered, and rotary evaporation removes and desolvates, and obtains light yellow butene dioic acid two diamantane of 3g-2-alcohol ester liquid (productive rate is 47%), and its structural formula is as follows
Claims (6)
1. the synthetic method of an adamantyl unsaturated ester is characterized in that may further comprise the steps:
(1) adamantanol is dissolved in the organic solvent, joins in the there-necked flask simultaneously with tertiary amine and stir, wherein the mol ratio of adamantanol and tertiary amine is 1: 1～3;
(2) unsaturated acyl chlorides is dissolved in obtains unsaturated acyl chlorides organic solution in the organic solvent, in there-necked flask, drip this unsaturated acyl chlorides organic solution in 3 hours, after dropwising, reaction solution continues to stir 5 hours, temperature of reaction is 0-5 ℃, and wherein the mol ratio of adamantanol and acyl chlorides is 1: 1～2;
(3) above-mentioned solution is carried out suction filtration, washing then, dry, rotary evaporation promptly get the adamantyl unsaturated ester monomer.
2. method according to claim 1, it is characterized in that, adamantanol described in the step (1) is 1-adamantanol, 2-adamantanol, 2-methyl-2-adamantanol, 2-ethyl-2-adamantanol, 3-amido-1-adamantanol, 1, a kind of in 3-two adamantanols.
3. method according to claim 1 is characterized in that, the tertiary amine described in the step (1) is a kind of in triethylamine, tripropyl amine, tri-isopropyl amine, the tri-n-butylamine.
4. method according to claim 1 is characterized in that, the organic solvent described in the step (1) is a kind of in benzene,toluene,xylene, methylene dichloride, the trichloromethane.
5. method according to claim 1 is characterized in that, the unsaturated acyl chlorides described in the step (2) is acrylate chloride, methacrylic chloride, maleic chloride, 2-butylene acyl chlorides, 3, a kind of in the 3-dimethyl acryloyl chloride.
6. method according to claim 1 is characterized in that, solution suction filtration, washing after reaction is finished described in the step (3), and wherein washing process is used 1mol/L HCl solution, 1mol/LNaHCO respectively
3Solution, deionized water wash three times.
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|---|---|---|---|
| CN 201010151328 CN101798263A (en) | 2010-04-16 | 2010-04-16 | Method for preparing unsaturated adamantane ester |
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| CN 201010151328 CN101798263A (en) | 2010-04-16 | 2010-04-16 | Method for preparing unsaturated adamantane ester |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102241678A (en) * | 2011-04-26 | 2011-11-16 | 辽宁利锋科技开发有限公司 | Antitumor effect and application of alicyclic structure-containing compound |
| CN102875397A (en) * | 2012-10-24 | 2013-01-16 | 上海万代制药有限公司 | Meclofenoxatum preparation method |
| CN109503654A (en) * | 2018-12-28 | 2019-03-22 | 山东泰和水处理科技股份有限公司 | The separation method of catalyst in a kind of esterification system |
| CN112661637A (en) * | 2020-12-23 | 2021-04-16 | 上海博栋化学科技有限公司 | Degradable resin monomer synthesized from adamantanone and preparation method thereof |
| CN113717314A (en) * | 2021-08-26 | 2021-11-30 | 江苏集萃光敏电子材料研究所有限公司 | Photosensitive film-forming resin, photoresist composition and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1429195A (en) * | 2000-05-16 | 2003-07-09 | 株式会社德山 | Process for producing 2-alkyl-2-adamantyl ester |
-
2010
- 2010-04-16 CN CN 201010151328 patent/CN101798263A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1429195A (en) * | 2000-05-16 | 2003-07-09 | 株式会社德山 | Process for producing 2-alkyl-2-adamantyl ester |
Non-Patent Citations (1)
| Title |
|---|
| 《中国优秀硕士学位论文全文数据库工程科技Ⅰ辑B014-36》 20051115 吴纬纬 N_芳香基丙烯酰胺的Baylis_Hillman反应及几个精细化学品的合成研究 第28-29页2.2.2节分步合成 1-6 , 第7期 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102241678A (en) * | 2011-04-26 | 2011-11-16 | 辽宁利锋科技开发有限公司 | Antitumor effect and application of alicyclic structure-containing compound |
| CN102875397A (en) * | 2012-10-24 | 2013-01-16 | 上海万代制药有限公司 | Meclofenoxatum preparation method |
| CN109503654A (en) * | 2018-12-28 | 2019-03-22 | 山东泰和水处理科技股份有限公司 | The separation method of catalyst in a kind of esterification system |
| CN112661637A (en) * | 2020-12-23 | 2021-04-16 | 上海博栋化学科技有限公司 | Degradable resin monomer synthesized from adamantanone and preparation method thereof |
| CN113717314A (en) * | 2021-08-26 | 2021-11-30 | 江苏集萃光敏电子材料研究所有限公司 | Photosensitive film-forming resin, photoresist composition and preparation method thereof |
| CN113717314B (en) * | 2021-08-26 | 2023-09-22 | 江苏集萃光敏电子材料研究所有限公司 | Photosensitive film-forming resin, photoresist composition and preparation method thereof |
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Application publication date: 20100811 |