CN113214266A - Crosslinking agent containing benzene ring and preparation method thereof - Google Patents
Crosslinking agent containing benzene ring and preparation method thereof Download PDFInfo
- Publication number
- CN113214266A CN113214266A CN202110452585.0A CN202110452585A CN113214266A CN 113214266 A CN113214266 A CN 113214266A CN 202110452585 A CN202110452585 A CN 202110452585A CN 113214266 A CN113214266 A CN 113214266A
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- benzene ring
- cross
- agent containing
- linking agent
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- 239000003431 cross linking reagent Substances 0.000 title claims abstract description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 25
- -1 benzene series compound Chemical class 0.000 claims abstract description 18
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 18
- UUGLSEIATNSHRI-UHFFFAOYSA-N 1,3,4,6-tetrakis(hydroxymethyl)-3a,6a-dihydroimidazo[4,5-d]imidazole-2,5-dione Chemical compound OCN1C(=O)N(CO)C2C1N(CO)C(=O)N2CO UUGLSEIATNSHRI-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003960 organic solvent Substances 0.000 claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 11
- 239000003377 acid catalyst Substances 0.000 claims abstract description 10
- 238000002156 mixing Methods 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 238000003756 stirring Methods 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 230000007935 neutral effect Effects 0.000 claims abstract description 7
- 238000000926 separation method Methods 0.000 claims abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- 239000003208 petroleum Substances 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- 150000007522 mineralic acids Chemical group 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 150000001555 benzenes Chemical class 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000001259 photo etching Methods 0.000 abstract description 9
- 229920002120 photoresistant polymer Polymers 0.000 abstract description 5
- 230000031700 light absorption Effects 0.000 abstract description 4
- 239000000243 solution Substances 0.000 description 28
- 239000007788 liquid Substances 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The embodiment of the invention discloses a cross-linking agent containing benzene rings and a preparation method thereof, wherein the method comprises the following steps: uniformly mixing tetramethylol glycoluril, a hydroxyl-containing benzene series compound and an alcohol compound in an organic solvent, adding an acid catalyst under a stirring state, heating for reaction, and reducing the temperature to room temperature after the reaction is finished to obtain a reaction solution; adjusting the pH of the reaction solution to be neutral, and then carrying out polarity separation on the reaction solution by using a developing agent to obtain a cross-linking agent solution containing benzene rings; and removing the solvent in the cross-linking agent solution containing the benzene ring to obtain the cross-linking agent containing the benzene ring. The cross-linking agent containing the benzene ring prepared by the method has high purity and moderate yield, can be used in the technical field of photoresist, improves the light absorption performance of the photoetching process, and greatly meets the requirements of the photoetching process.
Description
Technical Field
The invention relates to the technical field of cross-linking agents, in particular to a cross-linking agent containing benzene rings and a preparation method thereof.
Background
The cross-linking agent is also called bridging agent and is an important component of the hydrocarbon-polymerized photoresist, the photochemical curing action of the photoresist depends on the cross-linking agent with double photosensitive functional groups to participate in the reaction, and after exposure, the cross-linking agent generates double free radicals and interacts with the hydrocarbon-polymerized resin to form bridge bonds between polymer molecular chains and become insoluble substances with three-dimensional structures. In the technical field of photoresist, a cross-linking agent is applied to a photoetching process due to unique light absorption performance, particularly, the cross-linking agent containing a benzene ring structure can greatly improve the light absorption performance of the photoetching process, but in the prior art, when the photoetching process is carried out, the adopted cross-linking agent has fewer types and lower purity, and cannot meet the requirements of the photoetching process.
Disclosure of Invention
The embodiment of the invention provides a cross-linking agent containing benzene rings and a preparation method thereof, the cross-linking agent has high purity and moderate yield, and the requirements in a photoetching process are greatly met.
The embodiment of the invention provides a preparation method of a cross-linking agent containing benzene rings, which comprises the following steps:
s1, uniformly mixing tetramethylolglycoluril, a hydroxyl-containing benzene series compound and an alcohol compound in an organic solvent, adding an acid catalyst under a stirring state, heating for reaction, and cooling to room temperature after the reaction is finished to obtain a reaction solution;
s2, adjusting the pH of the reaction solution to be neutral, and then carrying out polarity separation on the reaction solution by using a developing agent to obtain a cross-linking agent solution containing benzene rings;
s3, removing the solvent in the cross-linking agent solution containing the benzene ring to obtain the cross-linking agent containing the benzene ring.
Preferably, in the preparation method of the crosslinking agent containing the benzene ring, the benzene series containing the hydroxyl group is one or more of phenol and benzyl alcohol.
Preferably, in the preparation method of the crosslinking agent containing a benzene ring, the alcohol compound is one or more of methanol and ethanol.
Preferably, in the method for preparing the crosslinking agent containing a benzene ring, the acid catalyst is an inorganic acid.
Preferably, in the preparation method of the crosslinking agent containing a benzene ring, the inorganic acid is one or more of concentrated nitric acid, concentrated hydrochloric acid, concentrated sulfuric acid and phosphoric acid.
Preferably, in the preparation method of the cross-linking agent containing the benzene ring, the organic solvent is one or more of ethyl acetate, dichloromethane, n-hexane, methanol, ethanol and petroleum ether.
Preferably, in the method for producing a crosslinking agent containing a benzene ring, the molar ratio of the tetramethylol glycoluril to the phenolic organic compound to the alcohol compound to the organic solvent is 1: (2-3): (2-3): (3-10), the temperature of the heating reaction in the S1 is 40-50 ℃, and the reaction time is 2-4 h.
Preferably, in the method for preparing the crosslinking agent containing a benzene ring, the pH of the reaction solution is adjusted to be neutral by using an alkaline agent in S2, wherein the alkaline agent is one or more of sodium hydroxide, potassium hydroxide, sodium carbonate and tetramethylammonium hydroxide.
Preferably, in the preparation method of the crosslinking agent containing the benzene ring, the developing agent comprises petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 100: 1.
The invention also provides a cross-linking agent containing benzene rings, which is prepared by the preparation method of the cross-linking agent containing benzene rings.
Compared with the prior art, the embodiment of the invention provides a cross-linking agent containing benzene rings and a preparation method thereof, wherein the method comprises the following steps: uniformly mixing tetramethylol glycoluril, a hydroxyl-containing benzene series compound and an alcohol compound in an organic solvent, adding an acid catalyst under a stirring state, heating for reaction, and reducing the temperature to room temperature after the reaction is finished to obtain a reaction solution; adjusting the pH of the reaction solution to be neutral, and then carrying out polarity separation on the reaction solution by using a developing agent to obtain a cross-linking agent solution containing benzene rings; and removing the solvent in the cross-linking agent solution containing the benzene ring to obtain the cross-linking agent containing the benzene ring. The cross-linking agent containing the benzene ring prepared by the method has high purity and moderate yield, can be used in the technical field of photoresist, improves the light absorption performance of the photoetching process, and greatly meets the requirements of the photoetching process.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are some, but not all, embodiments of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
It will be understood that the terms "comprises" and/or "comprising," when used in this specification and the appended claims, specify the presence of stated features, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, and/or groups thereof.
It is also to be understood that the terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. As used in the specification of the present invention and the appended claims, the singular forms "a," "an," and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise.
It should be further understood that the term "and/or" as used in this specification and the appended claims refers to and includes any and all possible combinations of one or more of the associated listed items.
The invention provides a cross-linking agent containing benzene rings and a preparation method thereof, wherein the method comprises the following steps: uniformly mixing tetramethylol glycoluril, a hydroxyl-containing benzene series compound and an alcohol compound in an organic solvent, adding an acid catalyst under a stirring state, heating for reaction, and reducing the temperature to room temperature after the reaction is finished to obtain a reaction solution; adjusting the pH of the reaction solution to be neutral by adopting an alkaline agent, and then carrying out polarity separation on the reaction solution by using a developing agent to obtain a cross-linking agent solution containing benzene rings; and removing the solvent in the cross-linking agent solution containing the benzene ring to obtain the high-purity cross-linking agent containing the benzene ring.
Specifically, the benzene series containing hydroxyl is one or more of phenol and benzyl alcohol, the alcohol compound is one or more of methanol and ethanol, the acid catalyst is an inorganic acid, the organic solvent is one or more of ethyl acetate, dichloromethane, n-hexane, methanol, ethanol and petroleum ether so as to facilitate recovery, the alkaline agent is one or more of sodium hydroxide, potassium hydroxide, sodium carbonate and tetramethylammonium hydroxide, the developing agent comprises petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 100: 1. In this embodiment, the acid catalyst is preferably one of concentrated hydrochloric acid, concentrated nitric acid, and concentrated sulfuric acid, and the alkaline agent is preferably sodium hydroxide, so as to finally obtain 1, 3-diphenoxy-4, 6-dimethoxymethylglycine as the crosslinking agent containing benzene ring, and the chemical reaction equation is as follows:
in a specific implementation process, the molar ratio of the tetramethylolglycoluril to the phenolic organic compound to the alcoholic compound to the organic solvent is 1: (2-3): (2-3): (3-10) uniformly mixing the tetramethylol glycoluril, the phenolic organic matter and the alcohol compound in an organic solvent, adding an acid catalyst under a stirring state, heating to 40-50 ℃, reacting for 2-4h to obtain a crude product of the cross-linking agent containing benzene rings, and then separating the crude product to remove impurities to obtain the cross-linking agent containing the benzene rings.
The crosslinking agent containing a benzene ring prepared in the following specific examples is 1, 3-diphenoxy-4, 6-dimethoxymethylglycine, and the purity of the prepared 1, 3-diphenoxy-4, 6-dimethoxymethylglycine is 97% or more, and the yield is 63% or more.
Example 1
Respectively adding 24.6g of tetramethylolglycoluril, 18.8g of phenol, 7.2g of methanol and 100g of n-hexane into a four-mouth bottle with condensation reflux for mixing, then adding 2ml of concentrated hydrochloric acid under a stirring state, simultaneously heating to 50 ℃ for carrying out constant temperature reaction for 3 hours, cooling to room temperature after the reaction is finished, then regulating the pH of the reaction solution to 7 by using NaOH aqueous solution, removing the n-hexane in the reaction solution, and reacting the reaction solution after the n-hexane is removed with petroleum ether: ethyl acetate 100:1 is used as a developing agent to carry out column treatment, and finally, the reaction solution after column treatment is subjected to solvent removal, so that 38g of colorless viscous liquid can be obtained, wherein the colorless viscous liquid is 1, 3-diphenoxy-4, 6-dimethoxymethylglycine, the purity of the colorless viscous liquid is 97.73%, and the yield of the colorless viscous liquid is 85.9%.
Example 2
Respectively adding 24.6g of tetramethylolglycoluril, 21.6g of benzyl alcohol, 7.2g of methanol and 100g of n-hexane into a four-mouth bottle with condensation reflux for mixing, then adding 2ml of concentrated sulfuric acid under a stirring state, simultaneously heating to 50 ℃ for carrying out constant temperature reaction for 3 hours, cooling to room temperature after the reaction is finished, then regulating the pH of the reaction solution to 7 by using NaOH aqueous solution, removing the n-hexane in the reaction solution, and reacting the reaction solution after the n-hexane is removed with petroleum ether: ethyl acetate 100:1 is used as a developing agent to carry out column treatment, and finally the reaction solution after column treatment is subjected to solvent removal, so that 30g of colorless viscous liquid can be obtained, wherein the colorless viscous liquid is 1, 3-diphenoxy-4, 6-dimethoxymethylglycine, the purity of the colorless viscous liquid is 98, 56%, and the yield of the colorless viscous liquid is 63.8%.
Example 3
Respectively adding 24.6g of tetramethylolglycoluril, 18.8g of phenol, 9.2g of ethanol and 100g of dichloromethane into a four-mouth bottle with condensing reflux for mixing, then adding 2ml of concentrated hydrochloric acid under a stirring state, simultaneously heating to 40 ℃ for carrying out constant temperature reaction for 3 hours, cooling to room temperature after the reaction is finished, then regulating the pH of the reaction solution to 7 by using NaOH aqueous solution, removing dichloromethane in the reaction solution, and adding petroleum ether: ethyl acetate 100:1 is used as a developing agent to carry out column treatment, and finally, the reaction solution after column treatment is subjected to solvent removal, so that 38g of colorless viscous liquid can be obtained, wherein the colorless viscous liquid is 1, 3-diphenoxy-4, 6-dimethoxymethylglycine, the purity of the colorless viscous liquid is 97.54%, and the yield of the colorless viscous liquid is 74.5%.
While the invention has been described with reference to specific embodiments, the invention is not limited thereto, and various equivalent modifications and substitutions can be easily made by those skilled in the art within the technical scope of the invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.
Claims (10)
1. A preparation method of a cross-linking agent containing a benzene ring is characterized by comprising the following steps:
s1, uniformly mixing tetramethylolglycoluril, a hydroxyl-containing benzene series compound and an alcohol compound in an organic solvent, adding an acid catalyst under a stirring state, heating for reaction, and cooling to room temperature after the reaction is finished to obtain a reaction solution;
s2, adjusting the pH of the reaction solution to be neutral, and then carrying out polarity separation on the reaction solution by using a developing agent to obtain a cross-linking agent solution containing benzene rings;
s3, removing the solvent in the cross-linking agent solution containing the benzene ring to obtain the cross-linking agent containing the benzene ring.
2. The method for preparing a crosslinking agent containing a benzene ring according to claim 1, wherein the benzene series containing a hydroxyl group is one or more of phenol and benzyl alcohol.
3. The method for preparing a crosslinking agent containing a benzene ring according to claim 1, wherein the alcohol compound is one or more of methanol and ethanol.
4. The method of claim 1, wherein the acid catalyst is an inorganic acid.
5. The method of claim 4, wherein the inorganic acid is one or more of concentrated nitric acid, concentrated hydrochloric acid, concentrated sulfuric acid, and phosphoric acid.
6. The method for preparing a crosslinking agent containing a benzene ring according to claim 1, wherein the organic solvent is one or more of ethyl acetate, dichloromethane, n-hexane, methanol, ethanol, and petroleum ether.
7. The method of claim 1, wherein the molar ratio of the tetramethylol glycoluril to the phenolic organic compound to the alcoholic compound to the organic solvent is 1: (2-3): (2-3): (3-10), the temperature of the heating reaction in the S1 is 40-50 ℃, and the reaction time is 2-4 h.
8. The method according to claim 1, wherein the pH of the reaction solution is adjusted to neutral in S2 by using an alkaline agent, wherein the alkaline agent is one or more selected from sodium hydroxide, potassium hydroxide, sodium carbonate, and tetramethylammonium hydroxide.
9. The method for preparing the crosslinking agent containing the benzene ring according to claim 1, wherein the developing solvent comprises petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 100: 1.
10. A crosslinking agent containing a benzene ring, which is produced by the production method of the crosslinking agent containing a benzene ring according to any one of claims 1 to 9.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110452585.0A CN113214266A (en) | 2021-04-26 | 2021-04-26 | Crosslinking agent containing benzene ring and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110452585.0A CN113214266A (en) | 2021-04-26 | 2021-04-26 | Crosslinking agent containing benzene ring and preparation method thereof |
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| Publication Number | Publication Date |
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| CN113214266A true CN113214266A (en) | 2021-08-06 |
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| CN202110452585.0A Pending CN113214266A (en) | 2021-04-26 | 2021-04-26 | Crosslinking agent containing benzene ring and preparation method thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114262396A (en) * | 2021-12-24 | 2022-04-01 | 宁波南大光电材料有限公司 | Etching-adjustable glycoluril oligomer and preparation method thereof |
| CN114292273A (en) * | 2021-12-30 | 2022-04-08 | 宁波南大光电材料有限公司 | Preparation method of cross-linking agent containing benzene ring |
| CN114315841A (en) * | 2021-12-29 | 2022-04-12 | 宁波南大光电材料有限公司 | Aryl-containing glycoluril oligomer and application thereof |
| CN115974880A (en) * | 2022-12-28 | 2023-04-18 | 上海彤程电子材料有限公司 | A kind of crosslinking agent and preparation method thereof, photoresist |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114262396A (en) * | 2021-12-24 | 2022-04-01 | 宁波南大光电材料有限公司 | Etching-adjustable glycoluril oligomer and preparation method thereof |
| CN114315841A (en) * | 2021-12-29 | 2022-04-12 | 宁波南大光电材料有限公司 | Aryl-containing glycoluril oligomer and application thereof |
| CN114292273A (en) * | 2021-12-30 | 2022-04-08 | 宁波南大光电材料有限公司 | Preparation method of cross-linking agent containing benzene ring |
| CN115974880A (en) * | 2022-12-28 | 2023-04-18 | 上海彤程电子材料有限公司 | A kind of crosslinking agent and preparation method thereof, photoresist |
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