CN114276323A - Preparation method of carbonate group-containing photoresist resin monomer - Google Patents
Preparation method of carbonate group-containing photoresist resin monomer Download PDFInfo
- Publication number
- CN114276323A CN114276323A CN202111643372.2A CN202111643372A CN114276323A CN 114276323 A CN114276323 A CN 114276323A CN 202111643372 A CN202111643372 A CN 202111643372A CN 114276323 A CN114276323 A CN 114276323A
- Authority
- CN
- China
- Prior art keywords
- resin monomer
- carbonate group
- photoresist resin
- reduced pressure
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920005989 resin Polymers 0.000 title claims abstract description 25
- 239000011347 resin Substances 0.000 title claims abstract description 25
- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 24
- 239000000178 monomer Substances 0.000 title claims abstract description 20
- 125000005587 carbonate group Chemical group 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 33
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 21
- JFMGYULNQJPJCY-UHFFFAOYSA-N 4-(hydroxymethyl)-1,3-dioxolan-2-one Chemical compound OCC1COC(=O)O1 JFMGYULNQJPJCY-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 10
- -1 hydroxymethyl dioxolane ketone Chemical class 0.000 claims abstract description 10
- 239000000378 calcium silicate Substances 0.000 claims abstract description 8
- 229910052918 calcium silicate Inorganic materials 0.000 claims abstract description 8
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 claims abstract description 8
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000011230 binding agent Substances 0.000 claims abstract description 7
- 238000005886 esterification reaction Methods 0.000 claims abstract description 7
- 239000003112 inhibitor Substances 0.000 claims abstract description 7
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 7
- 238000000746 purification Methods 0.000 claims abstract description 6
- 150000002148 esters Chemical group 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 238000002156 mixing Methods 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 238000004821 distillation Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000000706 filtrate Substances 0.000 claims description 8
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 4
- 238000010791 quenching Methods 0.000 claims description 4
- 230000000171 quenching effect Effects 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 239000012295 chemical reaction liquid Substances 0.000 claims description 2
- 239000010410 layer Substances 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 claims description 2
- 238000000967 suction filtration Methods 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 239000002952 polymeric resin Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 229920003002 synthetic resin Polymers 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 230000009471 action Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Images
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention relates to a preparation method of a carbonate group-containing photoresist resin monomer, which comprises the following reaction route:
wherein R is a hydrogen atom or C1～C6Alkyl groups of (a); the preparation method comprises the following reaction steps: a) mixing glycerol, dimethyl carbonate and calcium silicate, removing generated methanol through ester exchange reaction, and purifying to obtain hydroxymethyl dioxolanone; b) dissolving hydroxymethyl dioxolane ketone, a polymerization inhibitor and an acid-binding agent in an organic solvent, then dropwise adding alkyl acryloyl chloride, and purifying after esterification reaction to obtain the carbonate group-containing photoresist resin monomer. The catalyst calcium silicate is used, so that the activity is higher, the post-treatment is simple, and the preparation method and the purification method ensure that the product has high yield and high purity.
Description
Technical Field
The invention relates to the technical field of photoresist, in particular to a preparation method of a carbonate group-containing photoresist resin monomer.
Background
The chemically amplified photoresist is a photoresist based on the principle of chemical amplification, and the main components of the chemically amplified photoresist are polymer resin, Photo Acid Generator (PAG), and corresponding additives (additives) and solvent. Among them, the polymer resin is formed by copolymerization between resin monomers having different side chain structures, which are key components for imparting desired functions to the polymer resin, and usually provides the polymer resin with a polar group and an acid-sensitive group. The polar group can balance the hydrophilicity and hydrophobicity of the resin, improve the adhesion between the resin and the substrate, and provide developability for the host resin. The acid sensitive group can be separated from the side chain under the action of a photoacid generator, so that the resin is converted from insoluble to alkali-soluble, and the solubility contrast of the exposed region and the unexposed region is realized.
The carbonic ester group-containing photoresist resin monomer is polymer resin widely applied to 193nm photoresist, can improve the adhesion between resin and a substrate, and has poor catalytic effect of a catalyst in the existing preparation process.
Disclosure of Invention
The present invention is directed to a method for preparing a monomer for a photoresist resin containing carbonate groups, which overcomes the above-mentioned drawbacks of the prior art.
In order to achieve the object of the present invention, the present application provides the following technical solutions.
In a first aspect, the present application provides a method for preparing a carbonate group-containing photoresist resin monomer, characterized in that the method comprises the following reaction scheme:
the preparation method comprises the following reaction steps:
a) mixing glycerol, dimethyl carbonate and calcium silicate, removing generated methanol through ester exchange reaction, and purifying to obtain hydroxymethyl dioxolanone;
b) dissolving hydroxymethyl dioxolane ketone, a polymerization inhibitor and an acid-binding agent in an organic solvent, then dropwise adding alkyl acryloyl chloride, and purifying after esterification reaction to obtain the carbonate group-containing photoresist resin monomer.
In an embodiment of the first aspect, step a) further includes the following technical features:
a1) the molar ratio of the glycerol to the dimethyl carbonate is 1 (1-2), such as 1: 1;
a2) the calcium silicate is 0.5-1.5 wt%, such as 1 wt% of glycerol;
a3) the temperature of the ester exchange reaction is 70-80 ℃, and the reaction time is 0.5-2 h;
a4) the distillation temperature for removing methanol was 72 ℃ as the internal temperature, and the distillation was terminated when the internal temperature was increased to 80 ℃.
In one embodiment of the first aspect, the purification in step a) comprises the steps of: removing the generated methanol, and performing suction filtration on the obtained reaction liquid to obtain a filtrate; the filtrate is decompressed and concentrated, and then decompressed and distilled.
In one embodiment of the first aspect, the temperature of the reduced pressure concentration is 35 to 45 ℃, the pressure of the reduced pressure concentration is 20 to 40mmHg, and the time of the reduced pressure concentration is 2 to 4 hours;
the temperature of the reduced pressure distillation is 50-60 ℃, the pressure of the reduced pressure distillation is 0.1-0.5 mmHg, and the time of the reduced pressure distillation is 2-4 hours.
In an embodiment of the first aspect, step b) further includes one of the following technical features:
b1) the polymerization inhibitor is selected from one of 4-methoxyphenol or an antioxidant 264;
b2) the acid-binding agent is selected from one of triethylamine or N, N-dimethyl ethylenediamine;
b3) the organic solvent is selected from one of dichloromethane or dichloroethane;
b4) the molar ratio of the hydroxymethyl dioxolanone to the alkyl acryloyl chloride to the acid-binding agent is 1 (1.1-1.5) to (1.3-2.0), such as 1: 1.2: 1.5;
b5) the polymerization inhibitor is 0.5 to 1.5 wt%, such as 1 wt%, of the hydroxymethyl dioxolanone.
In one embodiment of the first aspect, in the step b), the temperature for dropping the alkylacryloyl chloride is controlled to be 0 to 5 ℃.
In one embodiment of the first aspect, in the step b), the temperature of the esterification reaction is 25 to 30 ℃ and the reaction time is 1 to 3 hours.
In one embodiment of the first aspect, the purification in step b) comprises the steps of: adding water into the reaction solution after the esterification reaction for quenching, and layering the mixed solution into a water layer and an organic layer; the organic layer was washed with water, concentrated under reduced pressure to remove the organic solvent, and then distilled under reduced pressure using an oil pump.
In one embodiment of the first aspect, the temperature of the reduced pressure distillation is 70 to 80 ℃ and the time is 2 to 4 hours.
Compared with the prior art, the invention has the beneficial effects that:
the catalyst calcium silicate is used in the invention, so that the activity is higher, the post-treatment is simple, and the preparation method and the purification method of the invention ensure that the product has high yield and high purity.
Drawings
FIG. 1 is a nuclear magnetic spectrum of the product obtained in the first step of example 1;
FIG. 2 is a nuclear magnetic spectrum of the product obtained in the second step of example 1;
FIG. 3 is a GC spectrum of the product obtained in the second step of example 1.
Detailed Description
Unless otherwise indicated, implied from the context, or customary in the art, all parts and percentages herein are by weight and the testing and characterization methods used are synchronized with the filing date of the present application. Where applicable, the contents of any patent, patent application, or publication referred to in this application are incorporated herein by reference in their entirety and their equivalent family patents are also incorporated by reference, especially as they disclose definitions relating to synthetic techniques, products and process designs, polymers, comonomers, initiators or catalysts, and the like, in the art. To the extent that a definition of a particular term disclosed in the prior art is inconsistent with any definitions provided herein, the definition of the term provided herein controls.
The numerical ranges in this application are approximations, and thus may include values outside of the ranges unless otherwise specified. A numerical range includes all numbers from the lower value to the upper value, in increments of 1 unit, provided that there is a separation of at least 2 units between any lower value and any higher value. For example, if a component, physical or other property (e.g., molecular weight, etc.) is recited as 100 to 1000, it is intended that all individual values, e.g., 100, 101,102, etc., and all subranges, e.g., 100 to 166,155 to 170,198 to 200, etc., are explicitly recited. For ranges containing a numerical value less than 1 or containing a fraction greater than 1 (e.g., 1.1, 1.5, etc.), then 1 unit is considered appropriate to be 0.0001, 0.001, 0.01, or 0.1. For ranges containing single digit numbers less than 10 (e.g., 1 to 5), 1 unit is typically considered 0.1. These are merely specific examples of what is intended to be expressed and all possible combinations of numerical values between the lowest value and the highest value enumerated are to be considered to be expressly stated in this application. It should also be noted that the terms "first," "second," and the like herein do not define a sequential order, but merely distinguish between different structures.
When used with respect to chemical compounds, the singular includes all isomeric forms and vice versa (e.g., "hexane" includes all isomers of hexane, individually or collectively) unless expressly specified otherwise. In addition, unless explicitly stated otherwise, the use of the terms "a", "an" or "the" are intended to include the plural forms thereof.
The terms "comprising," "including," "having," and derivatives thereof do not exclude the presence of any other component, step or procedure, and are not intended to exclude the presence of other elements, steps or procedures not expressly disclosed herein. To the extent that any doubt is eliminated, all compositions herein containing, including, or having the term "comprise" may contain any additional additive, adjuvant, or compound, unless expressly stated otherwise. Rather, the term "consisting essentially of … …" excludes any other components, steps or processes from the scope of any of the terms hereinafter recited, except those necessary for performance. The term "consisting of … …" does not include any components, steps or processes not specifically described or listed. Unless explicitly stated otherwise, the term "or" refers to the listed individual members or any combination thereof.
Examples
The following will describe in detail the embodiments of the present invention, which are implemented on the premise of the technical solution of the present invention, and the detailed embodiments and the specific operation procedures are given, but the scope of the present invention is not limited to the following embodiments.
Example 1
The first step is as follows:
the reaction equation is as follows:
material proportioning:
the operation process is as follows:
under the protection of nitrogen, glycerol (460.5g, 5mol), dimethyl carbonate (450.1g, 5mol) and calcium silicate (4.6g) were added to a 2000mL four-necked flask, and the mixture was refluxed at elevated temperature. After the reaction for 1 hour after refluxing, methanol was distilled off, and the internal temperature was 72 ℃ and increased to 80 ℃ as methanol was distilled off, thereby completing the reaction.
After the reaction, the reaction solution is filtered to remove solids, the filtrate is concentrated under reduced pressure at 40 ℃ and 20-40 mmHg for 2-4 hours to remove the solvent, and then the filtrate is distilled under reduced pressure at 50-60 ℃ and 0.1-0.5 mmHg for 2-4 hours to obtain 425g of colorless liquid hydroxymethyl dioxolanone, wherein the nuclear magnetic spectrum of the hydroxymethyl dioxolanone is shown in FIG. 1, (GC-95%, and the yield y-72%).
The second step is that:
the reaction equation is as follows:
material proportioning:
hydroxymethyl-dioxolanone (354.2g, 3mol) obtained in the first step was charged into a 2L four-necked reaction flask, stirring was turned on, methylene chloride (1100g), 4-methoxyphenol (3.5g), and triethylamine (455.4g, 4.5mol) were added under nitrogen, and the mixture was cooled to 0 ℃ after being stirred to dissolve.
And (3) beginning to dropwise add methacryloyl chloride (376.3g, 3.6mol), controlling the dropwise adding temperature to be 0-5 ℃, and after dropwise adding, heating to 25-30 ℃ to continue reacting for 1 hour. Sampling (the content of hydroxymethyl dioxolanone is less than or equal to 0.5 percent).
After the product is qualified, 200g of water is added dropwise for quenching, and the mixture is stirred for 0.5 hour.
The organic phase was washed once more with 200g of water. Concentrating under reduced pressure to remove solvent, and distilling under reduced pressure at 70-80 deg.C for 2-4 hr with oil pump to obtain colorless transparent liquid 475.7g, wherein the nuclear magnetic spectrum and GC spectrum are shown in FIG. 2 and FIG. 3 respectively. (purity GC 99.0%, yield y 85%).
Comparative example 1
The first step is as follows:
under the protection of nitrogen, glycerol (460.5g, 5mol), dimethyl carbonate (450.1g, 5mol) and calcium oxide (4.6g) were added into a 2000mL four-necked flask, and the mixture was refluxed at elevated temperature. After the reaction for 1 hour after refluxing, methanol was distilled off, and the internal temperature was 72 ℃ and increased to 80 ℃ as methanol was distilled off, thereby completing the reaction.
After the reaction is finished, filtering the reaction solution to remove solids, concentrating the filtrate under reduced pressure at 40 ℃ and 20-40 mmHg for 2-4 hours to remove the solvent, distilling the filtrate under reduced pressure at 50-60 ℃ and 0.1-0.5 mmHg for 2-4 hours to obtain 354.2g of colorless liquid hydroxymethyl dioxolane ketone, and detecting by nuclear magnetism, wherein GC is 86%, and the yield y is 60%.
Also in this operation, more dimethyl carbonate remains and calcium oxide removal is more difficult, being doped in hydroxymethyl-dioxolanone.
Second step of
The hydroxymethyl dioxolanone (354.2g, 3mol) prepared in the first step was added in its entirety to a 2L four-necked reaction flask, stirring was turned on, methylene chloride (1100g), 4-methoxyphenol (3.5g), and triethylamine (455.4g, 4.5mol) were added under nitrogen, and after stirring and dissolution, the temperature was lowered to 0 ℃.
And (3) beginning to dropwise add methacryloyl chloride (376.3g, 3.6mol), controlling the dropwise adding temperature to be 0-5 ℃, after dropwise adding, heating to 25-30 ℃ to continue reacting for 1 hour until the content of hydroxymethyl dioxolane ketone is detected to be less than or equal to 0.5%.
After the product is qualified, 200g of water is added dropwise for quenching, and the mixture is stirred for 0.5 hour.
The organic phase was washed once more with 200g of water. Concentrating under reduced pressure to remove the solvent, and distilling under reduced pressure at 70-80 deg.C for 2-4 hr by using oil pump to obtain colorless transparent liquid 325g, wherein the purity GC is 82.0% and the yield y is 58.1%.
The embodiments described above are intended to facilitate the understanding and appreciation of the application by those skilled in the art. It will be readily apparent to those skilled in the art that various modifications to these embodiments may be made, and the generic principles described herein may be applied to other embodiments without the use of the inventive faculty. Therefore, the present application is not limited to the embodiments herein, and those skilled in the art who have the benefit of this disclosure will appreciate that many modifications and variations are possible within the scope of the present application without departing from the scope and spirit of the present application.
Claims (9)
1. A preparation method of a carbonate group-containing photoresist resin monomer is characterized by comprising the following reaction route:
the preparation method comprises the following reaction steps:
a) mixing glycerol, dimethyl carbonate and calcium silicate, removing generated methanol through ester exchange reaction, and purifying to obtain hydroxymethyl dioxolanone;
b) dissolving hydroxymethyl dioxolane ketone, a polymerization inhibitor and an acid-binding agent in an organic solvent, then dropwise adding alkyl acryloyl chloride, and purifying after esterification reaction to obtain the carbonate group-containing photoresist resin monomer.
2. The method for preparing a carbonate group-containing photoresist resin monomer according to claim 1, wherein the step a) further comprises the following technical features:
a1) the molar ratio of the glycerol to the dimethyl carbonate is 1 (1-2);
a2) the calcium silicate accounts for 0.5-1.5 wt% of the glycerol;
a3) the temperature of the ester exchange reaction is 70-80 ℃, and the reaction time is 0.5-2 h;
a4) the distillation temperature for removing methanol was 72 ℃ as the internal temperature, and the distillation was terminated when the internal temperature was increased to 80 ℃.
3. The method for preparing a carbonate group-containing photoresist resin monomer according to claim 1, wherein the purification in step a) comprises the steps of: removing the generated methanol, and performing suction filtration on the obtained reaction liquid to obtain a filtrate; the filtrate is decompressed and concentrated, and then decompressed and distilled.
4. The method for preparing a carbonate group-containing photoresist resin monomer according to claim 3, wherein the temperature of the concentration under reduced pressure is 35 to 45 ℃, the pressure of the concentration under reduced pressure is 20 to 40mmHg, and the time of the concentration under reduced pressure is 2 to 4 hours;
the temperature of the reduced pressure distillation is 50-60 ℃, the pressure of the reduced pressure distillation is 0.1-0.5 mmHg, and the time of the reduced pressure distillation is 2-4 hours.
5. The method for preparing a carbonate group-containing photoresist resin monomer according to claim 1, wherein step b) further comprises one of the following technical features:
b1) the polymerization inhibitor is selected from one of 4-methoxyphenol or an antioxidant 264;
b2) the acid-binding agent is selected from one of triethylamine or N, N-dimethyl ethylenediamine;
b3) the organic solvent is selected from one of dichloromethane or dichloroethane;
b4) the molar ratio of the hydroxymethyl dioxolanone to the alkyl acryloyl chloride to the acid-binding agent is 1 (1.1-1.5) to 1.3-2.0;
b5) the polymerization inhibitor is 0.5-1.5 wt% of hydroxymethyl dioxolanone.
6. The method for preparing a photoresist resin monomer containing a carbonate group according to claim 1, wherein the temperature of dropping the alkylacryloyl chloride in the step b) is controlled to be 0 to 5 ℃.
7. The method for preparing a carbonate group-containing photoresist resin monomer according to claim 1, wherein in step b), the temperature of the esterification reaction is 25 to 30 ℃ and the reaction time is 1 to 3 hours.
8. The method for preparing a carbonate group-containing photoresist resin monomer according to claim 1, wherein the purification in step b) comprises the steps of: adding water into the reaction solution after the esterification reaction for quenching, and layering the mixed solution into a water layer and an organic layer; the organic layer was washed with water, concentrated under reduced pressure to remove the organic solvent, and then distilled under reduced pressure using an oil pump.
9. The method for preparing a carbonate group-containing photoresist resin monomer according to claim 8, wherein the temperature of the reduced pressure distillation is 70 to 80 ℃ for 2 to 4 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111643372.2A CN114276323B (en) | 2021-12-29 | 2021-12-29 | Preparation method of carbonate-based photoresist resin monomer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111643372.2A CN114276323B (en) | 2021-12-29 | 2021-12-29 | Preparation method of carbonate-based photoresist resin monomer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114276323A true CN114276323A (en) | 2022-04-05 |
| CN114276323B CN114276323B (en) | 2023-12-29 |
Family
ID=80878239
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111643372.2A Active CN114276323B (en) | 2021-12-29 | 2021-12-29 | Preparation method of carbonate-based photoresist resin monomer |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114276323B (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4691041A (en) * | 1986-01-03 | 1987-09-01 | Texaco Inc. | Process for production of ethylene glycol and dimethyl carbonate |
| CN105709785A (en) * | 2014-12-05 | 2016-06-29 | 临沂中通科技有限公司 | Catalyst for preparing glycerol carbonate, using method and application thereof |
| CN110180524A (en) * | 2019-06-04 | 2019-08-30 | 大连理工大学 | A method of carbonic acid glyceride is prepared based on calcium silicates based composite catalyst |
-
2021
- 2021-12-29 CN CN202111643372.2A patent/CN114276323B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4691041A (en) * | 1986-01-03 | 1987-09-01 | Texaco Inc. | Process for production of ethylene glycol and dimethyl carbonate |
| CN105709785A (en) * | 2014-12-05 | 2016-06-29 | 临沂中通科技有限公司 | Catalyst for preparing glycerol carbonate, using method and application thereof |
| CN110180524A (en) * | 2019-06-04 | 2019-08-30 | 大连理工大学 | A method of carbonic acid glyceride is prepared based on calcium silicates based composite catalyst |
Non-Patent Citations (2)
| Title |
|---|
| KATHRYN A. BERCHTOLD 等: "Reactivity of Monovinyl (Meth)Acrylates Containing Cyclic Carbonates", MACROMOLECULES, vol. 41, no. 23, pages 9035 - 9043 * |
| PARMILA DEVI 等: "Production of glycerol carbonate using a novel Ti-SBA-15 catalyst", CHEMICAL ENGINEERING JOURNAL, vol. 346, pages 477 - 488 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN114276323B (en) | 2023-12-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPWO2015080240A1 (en) | Method for purifying compound or resin | |
| KR100970837B1 (en) | Fluorene-based resin polymer and negative photo-sensitive resin composition including the same | |
| KR20030076660A (en) | Fluorine-containing compounds and polymers and processes for producing the same | |
| KR102281960B1 (en) | (meth)acrylate compound, (meth)acrylic copolymer and photosensitive resin composition containing same | |
| CN111056945A (en) | Photoresist resin monomer synthesized from spiro [5.5] undecane-3, 9-dione and synthesis method thereof | |
| CN114276323A (en) | Preparation method of carbonate group-containing photoresist resin monomer | |
| KR101085839B1 (en) | Diolmethacrylate compound containing urethane bond, method of the preparation thereof, and polymer thereof | |
| EP3763752A1 (en) | Novel bifunctional (meth)acrylate compound and polymer | |
| KR100740803B1 (en) | Fluorine-containing vinyl ethers, their polymers, and resist compositions using such polymers | |
| KR100653302B1 (en) | Styrene Derivatives | |
| US11597696B2 (en) | Method for purifying polymerizable fluoromonomer by distillation | |
| US7312294B2 (en) | Norbornane lactone (meth)acrylate and polymer thereof | |
| CN114315625A (en) | Preparation method of acid diffusion inhibitor | |
| CN114276239B (en) | Preparation method of ketal structure-containing acid-sensitive photoresist resin monomer | |
| JP2009286721A (en) | alpha-SUBSTITUTED ACRYLATE DERIVATIVE, AND METHOD FOR PRODUCING THE SAME | |
| CN114292183B (en) | Preparation method of hydroxyl structure-containing photoresist resin monomer | |
| CN109485565B (en) | Preparation method of 1-methyl cyclohexyl methacrylate | |
| WO2006123605A1 (en) | Polymerizable compound for photoresist, polymer thereof, and photoresist composition containing such polymer | |
| CN112390718A (en) | Degradable photoresist resin monomer synthesized from trimethylbicyclo [2.2.2] octane dione and synthesis method thereof | |
| CN114213246B (en) | Preparation method of photoresist resin monomer | |
| JP4401050B2 (en) | Process for producing 1,3,5-adamantanetriol mono (meth) acrylate | |
| CN111138280A (en) | Photoresist resin monomer synthesized from 3-ethylbicyclo [3.3.1] nonane-2, 4-diketone and synthesis method thereof | |
| US8304572B2 (en) | Synthesis of fluoroalcohol-substituted (meth)acrylate esters and polymers derived therefrom | |
| CN114315573B (en) | Preparation method of acid-sensitive photoresist resin monomer | |
| CN114315766A (en) | Preparation method of photoresist resin monomer containing lactone structure |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |