CN105885004A - Bio-based photo-curable polyurethane and photoresist prepared with same - Google Patents
Bio-based photo-curable polyurethane and photoresist prepared with same Download PDFInfo
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- CN105885004A CN105885004A CN201610457541.6A CN201610457541A CN105885004A CN 105885004 A CN105885004 A CN 105885004A CN 201610457541 A CN201610457541 A CN 201610457541A CN 105885004 A CN105885004 A CN 105885004A
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- diisocyanate
- based light
- cured polyurethane
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3218—Polyhydroxy compounds containing cyclic groups having at least one oxygen atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/348—Hydroxycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
- C08G18/673—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen containing two or more acrylate or alkylacrylate ester groups
-
- 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
-
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention provides bio-based photo-curable polyurethane and a photoresist composition from the same and belongs to the field of photoresists. The photoresist composition is prepared by: reacting bio-based monomer isosorbide with a diisocyanate to obtain NCO-terminated monomer, reacting this monomer with dihydroxy acid to synthesize polyurethane prepolymer, terminating with acrylate monohydric alcohol to obtain bio-based photo-curable polyurethane, mixing the prepared polyurethane proportionally with a photoinitiator, a solvent, an active diluent and a pigment in the shade, and stirring well to enable full dissolution. By introducing the isosorbide, it is possible to improve corrosion resistance of the photoresist and improve its thermal performance and it is possible to produce an image with good comprehensive performance and high resolution.
Description
Technical field
The present invention relates to photoresist field, especially relate to a kind of by bio-based monomer isosorbide and two Carbimide .s
The bio-based light-cured polyurethane of esters monomer reaction gained and the photoresist of preparation thereof.
Background technology
Urethane acrylate (PUA) is to study at present more photoresist, combine polyurethane and
The premium properties of acrylate, has a higher laser curing velocity, good adhesive force, pliability,
Wearability, high rigidity, chemical resistance etc., be widely used to coating, ink and binding agent etc. multiple
Field.The general molecular weight of polyurethane is relatively big, and viscosity is higher, and the soft section of ratio accounted for is great.These performances make its glass
Glass transition temperature, hardness and acid number are the most relatively low, good toughness, and these performances are not suitable for applying leads at photoresist
Territory.
Isosorbide (ISB), as a kind of novel organism-based raw material, has good rigidity and without poison ring
The advantages such as guarantor can be as continuable intermediate polymer material.One study hotspot of its application is to be made
For comonomer for the modification of the polymer such as polyethers, polyester, polyurethane, Merlon, can significantly improve
The vitrification point of polymer, increase the intensity of polymer, high-temperature behavior and impact resistance, be introduced into into
Row is free-radical polymerized, improves the elching resistant of copolymer.
Add the acid number introducing regulation polyurethane of carboxyl so that copolymer has certain alkali solubility, finally
Can be applied in photoresist field.Therefore, synthetic glass transition temperature, hardness are higher, and acid number can
Adjusting, molecular weight is low, and the polyurethane that viscosity is little becomes technical key.Bio-based polyurethane is in photoetching at present
The application in glue field rarely has report.
Summary of the invention
The problems referred to above existed for prior art, the present invention provides a kind of bio-based light-cured polyurethane and system thereof
Standby photoresist.Bio-based light-cured polyurethane of the present invention have good adhesive force, wearability, higher hardness,
Chemical resistance and the advantage of good elching resistant.
Technical scheme is as follows:
A kind of bio-based light-cured polyurethane, its preparation method comprises the steps:
(1) by after diisocyanate and solvent, catalyst, polymerization inhibitor mixing, drip under the conditions of 40～60 DEG C
Isosorbide, insulation reaction 1.5～3.5h；
(2) 2 it are subsequently added, 2-dihydromethyl propionic acid or 2,2-dimethylolpropionic acid, protect under the conditions of 70～80 DEG C
Temperature reaction 4～8h；
(3) it is eventually adding polymerization inhibitor, adds the acrylate monomer of hydroxyl, protect under the conditions of 70～80 DEG C
Temperature reaction, during until can't detect the absworption peak of NCO with infrared spectrum, stopped reaction, prepare described biology
Base light-cured polyurethane.
In described step (1), diisocyanate is methyl diphenylene diisocyanate, polymeric diphenylmethane two
Isocyanates, toluene di-isocyanate(TDI), hexamethylene diisocyanate, isophorone diisocyanate, benzene two
One or more in methylene diisocyanate；Described catalyst is organic tin catalyst, tertiary amines catalysis
One or more in agent, the consumption of described catalyst is 0.01wt%～0.05wt% of total inventory.
In described step (1), diisocyanate is 2:1～2.5:1 with the mol ratio of isosorbide.
In described step (1), solvent is in N,N-dimethylformamide, N-Methyl pyrrolidone, acetone
Plant or multiple.
2,2-dihydromethyl propionic acid or 2,2-dimethylolpropionic acid and diisocyanate monomer in described step (2)
Mol ratio be 1.5～3:1.
In described step (3), polymerization inhibitor is MEHQ, hydroquinone, resorcinol, the tertiary fourth of 2,6-bis-
One or more in base paracresol, its consumption is 0.lwt%～0.5wt% of total inventory；Described hydroxyl
Acrylate monomer be 2-(Acryloyloxy)ethanol, hydroxyethyl methylacrylate, Hydroxypropyl acrylate, metering system
One in acid hydroxypropyl acrylate, pentaerythritol triacrylate.
In described step (3), the acrylate monomer of hydroxyl and the mol ratio of diisocyanate are 1:1～2.5:1.
Described step (1)～(3) whole during when using toluene-di-n-butylamine back titration method to measure reaction
NCO group content, after reaching theoretical value, carries out next step reaction.
A kind of photoresist of bio-based light-cured polyurethane, raw material and the quality of each raw material contained by described photoresist
Mark is:
Described reactive diluent is isobornyl acrylate, tripropylene glycol diacrylate, trimethylolpropane tris
Acrylate, dihydroxy methylpropane tetraacrylate, 1,6 hexanediol diacrylate, tetramethylolmethane tetrapropylene
One or more in acid esters；Described light trigger be 2-methyl isophthalic acid-(4-first mercaptophenyl)-2-morpholine-1-acetone,
Isopropyl thioxanthone, 2,4-diethyl sulfide how anthrone, 2,4,6-trimethyl benzoyl diphenyl base phosphine oxide, N-
Phenyl glycine, 4, one or more in 4-bis-(N, N '-dimethyl-amino) benzophenone；Described solvent is
In acetone, N,N-dimethylformamide, N-Methyl pyrrolidone, propylene glycol methyl ether acetate, butyl acetate
One or more.
Useful the having the technical effect that of the present invention
(1) bio-based light-cured polyurethane of the present invention uses the ring-type raw material that diisocyanate is resin, permissible
Increase the elching resistant of photoresist；Use isosorbide to increase the thermostability of urethane acrylate, improve tree
The glass transition temperature of fat, thus obtain that there is the mechanical property of excellence, thermostability, rub resistance, oxytolerant
The property changed and the resin of chemical resistance；Carboxylic dihydroxylic alcohols is used to introduce carboxyl in resin structure, from
And make resin have alkali solubility, meet photoresist the most solvable.
(2) acrylate monomer that bio-based light-cured polyurethane end of the present invention introduces hydroxyl makes it have
Heliosensitivity, only need to add a small amount of reactive diluent and can meet its light admittedly during preparation photoetching compositions formula
Change performance.
(3) bio-based light-cured polyurethane of the present invention is due to molecular weight, and viscosity is relatively low, during preparation photoresist
Need not use substantial amounts of solvent adjustment viscosity.
(4) bio-based light-cured polyurethane of the present invention and reactive diluent, solvent, light trigger, pigment etc.,
Cooperate between each component, synergism, make to prepare photoresist and be applied to development, prepare combination property good,
The image that resolution is higher.
Accompanying drawing explanation
Fig. 1 is the synthetic route chart of bio-based light-cured polyurethane described in the embodiment of the present invention 1.
Fig. 2 is the infrared spectrum of the bio-based light-cured polyurethane that embodiment 1 prepares, before (a) HEA grafting；
After (b) HEA grafting.
Fig. 3 is that after embodiment 1 prepares photoresist developing, the SEM of pattern schemes.
Detailed description of the invention
Below in conjunction with the accompanying drawings and embodiment, the present invention is specifically described.
Embodiment 1
(1) preparation of bio-based light-cured polyurethane:
Equipped with thermometer, reflux condensing tube, agitator tetra-mouthfuls of round-bottomed flasks of 250mL in add different Fo Er
Ketone diisocyanate (IPDI) 44.458g and dibutyl tin laurate (DBTDL) 0.295g, drips wherein
Enter isosorbide (ISB) 14.614g, add DMF 15g and carry out regulation system viscosity,
45 DEG C of insulation reaction 2h, are subsequently added 2,2-dihydromethyl propionic acid (DMPA) 6.706g, anti-75 DEG C of insulations
Answer 4h, be eventually adding polymerization inhibitor 2,6 ditertiary butyl p cresol 0.420g, add 2-(Acryloyloxy)ethanol
(HEA) 13.934g, until can't detect NCO at 2265cm with infrared spectrum-1During the absworption peak located, such as figure
Shown in 2, stopped reaction, required time is 5h, finally gives bio-based light-cured polyurethane.
The composite structure route of gained bio-based light-cured polyurethane is as shown in Figure 1.Whole process passes through toluene-two
N-butylamine back titration method measure reaction time NCO group content, when with theoretical NCO value close to time carry out next
Step reaction.
(2) preparation and the development of photoresist is tested:
Take bio-based light-cured polyurethane 42.4%, N,N-dimethylformamide 33.7%, 1,6-HD dipropyl
Alkene ester 15.2%, 2-methyl isophthalic acid-(4-first mercaptophenyl)-2-morpholine-1-acetone (907) and isopropyl thioxanthone (ITX)
Mixture (mass ratio is 2:1) 4.5%, phthalocyanine blue 4.2% are in centrifuge tube, and magnetic agitation, to mix homogeneously, obtains
To photoresist.
Gained photoresist is coated on copper coin, preliminary drying 30min under the conditions of 75 DEG C；Mask is covered and is being baked
Sample on, at 226mJ/cm2Under the conditions of expose；The sample exposed is placed in 0.5wt%Na2CO3Solution
In 45 seconds, obtain image after photoresist developing.The SEM of gained image schemes as shown in Figure 3.From Fig. 3
Can be seen that image is clear, lines are precipitous straight, and image resolution ratio reaches 40 μm.
Embodiment 2
(1) preparation of bio-based light-cured polyurethane:
Equipped with thermometer, reflux condensing tube, agitator tetra-mouthfuls of round-bottomed flasks of 250mL in add different Fo Er
Ketone diisocyanate (IPDI) 44.458g and dibutyl tin laurate (DBTDL) 0.295g, drips wherein
Enter isosorbide (ISB) 14.614g, add DMF 15g and carry out regulation system viscosity,
45 DEG C of insulation reaction 2h, are subsequently added 2,2-dihydromethyl propionic acid (DMPA) 6.706g, anti-75 DEG C of insulations
Answer 4h, be eventually adding polymerization inhibitor 2,6 ditertiary butyl p cresol 0.420g, add tetramethylolmethane three acrylic acid
Ester (PETA) 55.795g, until can't detect NCO at 2265cm with infrared spectrum-1During the absworption peak located,
Stopped reaction, required time is 5h, finally gives bio-based light-cured polyurethane.
NCO group content when whole process measures reaction by toluene-di-n-butylamine back titration method, when with theory
Nco value close to time carry out next step reaction.
(2) preparation and the development of photoresist is tested:
Take bio-based light-cured polyurethane 42.4%, N,N-dimethylformamide 33.7%, 1,6-HD dipropyl
Alkene ester 15.2%, 2-methyl isophthalic acid-(4-first mercaptophenyl)-2-morpholine-1-acetone (907) and isopropyl thioxanthone (ITX)
Mixture (mass ratio is 2:1) 4.5%, phthalocyanine blue 4.2% are in centrifuge tube, and magnetic agitation, to mix homogeneously, obtains
To photoresist.
Gained photoresist is coated on copper coin, preliminary drying 30min under the conditions of 75 DEG C；Mask is covered and is being baked
Sample on, at 226mJ/cm2Under the conditions of expose；The sample exposed is placed in 0.5wt%Na2CO3Solution
In 45 seconds, obtain image after photoresist developing.
Embodiment 3
(1) preparation of bio-based light-cured polyurethane:
Equipped with thermometer, reflux condensing tube, agitator tetra-mouthfuls of round-bottomed flasks of 250mL in add isophorone
Diisocyanate (IPDI) 44.458g and dibutyl tin laurate (DBTDL)) 0.295g, drips wherein
Enter isosorbide (ISB) 14.614g, add DMF 15g and carry out regulation system viscosity,
45 DEG C of insulation reaction 2h, are subsequently added 2,2-dihydromethyl propionic acid (DMPA)) 6.706g, 75 DEG C of insulations
Reaction 4h, is eventually adding polymerization inhibitor 2,6 ditertiary butyl p cresol 0.420g, adds 2-(Acryloyloxy)ethanol (HEA)
13.934g, until can't detect NCO at 2265cm with infrared spectrum-1During the absworption peak located, stopped reaction,
Required time is 5h, finally gives bio-based light-cured polyurethane.
NCO group content when whole process measures reaction by toluene-di-n-butylamine back titration method, when with theory
Nco value close to time carry out next step reaction.
(2) preparation and the development of photoresist is tested:
Take bio-based light-cured polyurethane 42.4%, N,N-dimethylformamide 33.7%, 1,6-HD dipropyl
Alkene ester 15.2%, 2-methyl isophthalic acid-(4-first mercaptophenyl)-2-morpholine-1-acetone (907) and isopropyl thioxanthone (ITX)
Mixture (mass ratio is 2:1) 4.5%, phthalocyanine blue 4.2% are in centrifuge tube, and magnetic agitation, to mix homogeneously, obtains
To photoresist.
Gained photoresist is coated on copper coin, preliminary drying 30min under the conditions of 75 DEG C；Mask is covered and is being baked
Sample on, at 226mJ/cm2Under the conditions of expose；The sample exposed is placed in 0.5wt%Na2CO3Solution
In 45 seconds, obtain image after photoresist developing.
Claims (10)
1. a bio-based light-cured polyurethane, it is characterised in that the preparation side of described bio-based light-cured polyurethane
Method comprises the steps:
(1) by after diisocyanate and solvent, catalyst, polymerization inhibitor mixing, drip under the conditions of 40～60 DEG C
Isosorbide, insulation reaction 1.5～3.5h；
(2) 2 it are subsequently added, 2-dihydromethyl propionic acid or 2,2-dimethylolpropionic acid, protect under the conditions of 70～80 DEG C
Temperature reaction 4～8h；
(3) it is eventually adding polymerization inhibitor, the acrylate monomer of hydroxyl, insulation reaction under the conditions of 70～80 DEG C,
During until can't detect the absworption peak of NCO with infrared spectrum, stopped reaction, prepare described bio-based photocuring
Polyurethane.
Bio-based light-cured polyurethane the most according to claim 1, it is characterised in that described in step (1)
Diisocyanate is methyl diphenylene diisocyanate, polymeric diphenylmethane diisocyanate, toluene diisocyanate
In acid esters, hexamethylene diisocyanate, isophorone diisocyanate, XDI
One or more；Described catalyst is one or more in organic tin catalyst, tertiary amine catalyst, institute
State 0.01wt%～0.05wt% that consumption is total inventory of catalyst.
Bio-based light-cured polyurethane the most according to claim 1, it is characterised in that described in step (1)
Diisocyanate is 2:1～2.5:1 with the mol ratio of isosorbide.
Bio-based light-cured polyurethane the most according to claim 1, it is characterised in that described in step (1)
Solvent is one or more in N,N-dimethylformamide, N-Methyl pyrrolidone, acetone.
Bio-based light-cured polyurethane the most according to claim 1, it is characterised in that described in step (2)
The mol ratio of 2,2-dihydromethyl propionic acid or 2,2-dimethylolpropionic acid and diisocyanate monomer is 1.5～3:1.
Bio-based light-cured polyurethane the most according to claim 1, it is characterised in that described in step (3)
Polymerization inhibitor be the one in MEHQ, hydroquinone, resorcinol, DBPC 2,6 ditertiary butyl p cresol or
Multiple, its consumption is 0.lwt%～0.5wt% of total inventory；The acrylate monomer of described hydroxyl is third
Olefin(e) acid hydroxyl ethyl ester, hydroxyethyl methylacrylate, Hydroxypropyl acrylate, Hydroxypropyl methacrylate, tetramethylolmethane
One in triacrylate.
Bio-based light-cured polyurethane the most according to claim 1, it is characterised in that described in step (3)
The acrylate monomer of hydroxyl and the mol ratio of diisocyanate are 1:1～2.5:1.
Bio-based light-cured polyurethane the most according to claim 1, it is characterised in that described step (1)～
(3) NCO group content when using toluene-di-n-butylamine back titration method to measure reaction during whole, when
After reaching theoretical value, carry out next step reaction.
9. one kind by the photoresist of bio-based light-cured polyurethane described in claim 1, it is characterised in that described light
The mass fraction of raw material contained by photoresist and each raw material is:
Photoresist the most according to claim 9, it is characterised in that described reactive diluent is that acrylic acid is different
Norbornene ester, tripropylene glycol diacrylate, trimethylolpropane trimethacrylate, dihydroxy methylpropane tetrapropylene
One or more in acid esters, 1,6 hexanediol diacrylate, tetramethylol methane tetraacrylate；Described light draws
Sending out agent is 2-methyl isophthalic acid-(4-first mercaptophenyl)-2-morpholine-1-acetone, isopropyl thioxanthone, 2,4-diethyl sulfide
How anthrone, 2,4,6-trimethyl benzoyl diphenyl base phosphine oxide, N-phenyl glycine, 4,4-bis-(N, N '-two
Methyl-amino) one or more in benzophenone；Described solvent is acetone, N,N-dimethylformamide, N-
One or more in methyl pyrrolidone, propylene glycol methyl ether acetate, butyl acetate.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610457541.6A CN105885004A (en) | 2016-06-22 | 2016-06-22 | Bio-based photo-curable polyurethane and photoresist prepared with same |
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| CN201610457541.6A CN105885004A (en) | 2016-06-22 | 2016-06-22 | Bio-based photo-curable polyurethane and photoresist prepared with same |
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| CN111269380A (en) * | 2018-12-04 | 2020-06-12 | 南通立方新材料科技有限公司 | Photocuring arabinose-based polyurethane acrylate and preparation method thereof |
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| CN115016228A (en) * | 2022-05-10 | 2022-09-06 | 常州大学 | Polyurethane acrylate photoresist and preparation method thereof |
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| CN115016228A (en) * | 2022-05-10 | 2022-09-06 | 常州大学 | Polyurethane acrylate photoresist and preparation method thereof |
| CN115016228B (en) * | 2022-05-10 | 2024-03-15 | 常州大学 | Polyurethane acrylic ester photoresist and preparation method thereof |
| CN117304439A (en) * | 2023-09-26 | 2023-12-29 | 无锡爱勒普科技有限公司 | Polymer polyurethane special for semiconductor photoresist and production process thereof |
| CN117304439B (en) * | 2023-09-26 | 2024-04-12 | 无锡爱勒普科技有限公司 | Polymer polyurethane special for semiconductor photoresist and production process thereof |
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