CN113174015A - Rigid photosensitive resin composition based on polyurethane acrylate and production method thereof - Google Patents
Rigid photosensitive resin composition based on polyurethane acrylate and production method thereof Download PDFInfo
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- CN113174015A CN113174015A CN202010926489.0A CN202010926489A CN113174015A CN 113174015 A CN113174015 A CN 113174015A CN 202010926489 A CN202010926489 A CN 202010926489A CN 113174015 A CN113174015 A CN 113174015A
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 22
- 239000011342 resin composition Substances 0.000 title claims abstract description 20
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 15
- 239000004814 polyurethane Substances 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 13
- 239000000178 monomer Substances 0.000 claims abstract description 31
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims abstract description 26
- 150000001336 alkenes Chemical class 0.000 claims abstract description 14
- 239000002518 antifoaming agent Substances 0.000 claims abstract description 14
- 239000003381 stabilizer Substances 0.000 claims abstract description 9
- 239000011347 resin Substances 0.000 claims description 23
- 229920005989 resin Polymers 0.000 claims description 23
- 125000000524 functional group Chemical group 0.000 claims description 8
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 claims description 5
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 5
- 125000004386 diacrylate group Chemical group 0.000 claims description 5
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 claims description 5
- 238000007599 discharging Methods 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 3
- 229940113115 polyethylene glycol 200 Drugs 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 2
- VEBCLRKUSAGCDF-UHFFFAOYSA-N ac1mi23b Chemical compound C1C2C3C(COC(=O)C=C)CCC3C1C(COC(=O)C=C)C2 VEBCLRKUSAGCDF-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000005442 diisocyanate group Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 2
- 229940068918 polyethylene glycol 400 Drugs 0.000 claims description 2
- 229920000151 polyglycol Polymers 0.000 claims description 2
- 239000010695 polyglycol Substances 0.000 claims description 2
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
- 238000012360 testing method Methods 0.000 description 8
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 5
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 5
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 5
- NWWQVENFTIRUMF-UHFFFAOYSA-N diphenylphosphanyl 2,4,6-trimethylbenzoate Chemical compound CC1=CC(C)=CC(C)=C1C(=O)OP(C=1C=CC=CC=1)C1=CC=CC=C1 NWWQVENFTIRUMF-UHFFFAOYSA-N 0.000 description 5
- 238000000016 photochemical curing Methods 0.000 description 3
- 238000005452 bending Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229940119545 isobornyl methacrylate Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/006—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00
- C08F283/008—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00 on to unsaturated polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
The invention discloses a rigid photosensitive resin composition based on polyurethane acrylate and a production method thereof. A rigid photosensitive resin composition based on urethane acrylate comprises the following components in parts by weight: 10-75 parts of urethane acrylate; 10-25 parts of a difunctional alkene monomer; 10-20 parts of a monofunctional alkene monomer; 0.1-5 parts of a photoinitiator; 0.1-6 parts of a defoaming agent; 0.1-5 parts of a stabilizer. The invention has the beneficial effects that: good rigidity, low cost and easy production.
Description
Technical Field
The invention relates to a rigid photosensitive resin composition based on polyurethane acrylate and the technical field of a production method thereof.
Background
The photosensitive resin is irradiated under specific wavelength, liquid can be polymerized and then converted into solid, and the photosensitive resin is widely applied to industries such as medical treatment, cartoon handling, aviation, electric appliances, artworks and the like in recent years. Particularly, due to the rapid development of desktop-level LCD printers, photosensitive resin plays an important role in the fields of office and jewelry models, and the photocuring technology is developing towards higher-precision micro-nano technology.
The polyurethane acrylate prepolymer without benzene rings and the low-odor acrylate monomer are reacted to form high polymers with high crosslinking density, so that the rigid photosensitive resin is obtained, and the photosensitive resin has great application prospect.
However, in China, most of photosensitive resins have certain toxicity and odor, and the problems of low precision and poor mechanical properties of finished products and the like, so that the development of the photosensitive resins in China is seriously hindered.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a rigid photosensitive resin composition based on urethane acrylate and a production method thereof, which have the advantages of good rigidity, low cost and easy production.
The technical scheme adopted by the invention is as follows:
a rigid photosensitive resin composition based on urethane acrylate comprises the following components in parts by weight:
75 parts of urethane acrylate; 25 parts of difunctional alkene monomer; 20 parts of monofunctional alkene monomers; 0.1 part of photoinitiation; 0.1 part of defoaming agent; 0.1 part of stabilizer.
The polyurethane acrylate prepolymer contains a carbamate group (-NH-COO-) in a molecular chain, and the number average molecular weight is 2000-8000.
The polyurethane acrylate prepolymer is aliphatic polyurethane acrylate prepared from diisocyanate and polyglycol.
The difunctional alkene monomer is one or more of acrylate monomers containing 2 functional groups, vinyl ether monomers containing 2 functional groups or 2 norbornene monomers.
The acrylate monomers containing 2 functional groups include, but are not limited to, dipropylene glycol diacrylate, tricyclodecane dimethanol diacrylate, polyethylene glycol 200 diacrylate, polyethylene glycol 400 diacrylate, 1, 6-hexanediol diacrylate, tripropylene glycol diacrylate, tetra (ethylene glycol) diacrylate, and blends thereof.
The acrylate monomer containing 2 functional groups is 1, 6-hexanediol diacrylate, tripropylene glycol diacrylate or dipropylene glycol diacrylate.
A method for producing a rigid photosensitive resin composition based on urethane acrylate, comprising the steps of:
s1, a stirrer is arranged, a charging barrel is arranged on the stirrer, a cover is arranged at the upper end of the charging barrel, and a light-shading space is formed between the charging barrel and the cover in a matching manner; 6 feeding machines are arranged on the stirrer, each feeding machine is provided with a discharging port, and each discharging port is arranged in the light-shading space; the 6 feeding machines are respectively a first feeding machine, a second feeding machine, a third feeding machine, a fourth feeding machine, a fifth feeding machine and a sixth feeding machine; the 6 feeding machines and the stirrer are electrically connected with a controller; putting polyurethane acrylate on a first feeding machine; feeding a difunctional alkene monomer onto a second feeding machine; feeding the monofunctional alkene monomer into a third feeding machine; putting the photoinitiator into a fourth feeding machine; putting the defoaming agent into a fifth feeding machine; putting the stabilizer into a sixth feeding machine;
s2, under the condition of keeping out of the sun, putting urethane acrylate into a light-proof space through a first feeding machine, putting a difunctional monomer into the light-proof space through a second feeding machine, putting the monofunctional monomer into the light-proof space through a third feeding machine, putting a photoinitiator into the light-proof space through a fourth feeding machine, putting an antifoaming agent into the light-proof space through a fifth feeding machine, and putting a stabilizing agent into the light-proof space through a sixth feeding machine;
and S3, stirring uniformly by a stirrer to obtain the photosensitive resin.
The controller is electrically connected with a photosensitive sensor, the photosensitive sensor is installed in the light-shading space, and the controller is electrically connected with an input module; when the input module receives the control signal, the controller detects the light intensity inside the light-shading space through the photosensitive sensor; if the light intensity in the light-shading space is larger than a preset value, the controller stops the work of the 6 feeding machines; if the light intensity in the light-shading space is smaller than the preset value, the controller allows 6 feeding machines to feed materials.
The invention has the beneficial effects that: good rigidity, low cost and easy production.
Drawings
FIG. 1 is a first schematic diagram of the present invention;
fig. 2 is a schematic diagram of the principle of the present invention.
Detailed Description
As shown in fig. 1 to 2, a rigid photosensitive resin composition based on urethane acrylate and a method for preparing the same according to the present invention.
Example 1
300g of urethane acrylate prepolymer SL-01 (number average molecular weight 1000), 50g of 1, 6-hexanediol diacrylate, 35g of hydroxyethyl methacrylate, 16g of acryloylmorpholine, 8g of diphenyl- (2,4, 6-trimethylbenzoyl) oxyphosphorus, 4g of hydroquinone and 5g of an antifoaming agent were stirred uniformly in the absence of light to obtain photosensitive resin A1.
Example 2
300g of urethane acrylate prepolymer SL-01 (number average molecular weight 1000), 50g of tripropylene glycol diacrylate, 35g of hydroxyethyl methacrylate, 16g of acryloylmorpholine, 8g of diphenyl- (2,4, 6-trimethylbenzoyl) oxyphosphorus, 4g of hydroquinone and 5g of an antifoaming agent are stirred uniformly in the absence of light to obtain photosensitive resin A2.
Example 3
300g of urethane acrylate prepolymer SL-02 (number average molecular weight 1000), 50g of isobornyl methacrylate, 35g of hydroxyethyl methacrylate, 16g of acryloylmorpholine, 8g of diphenyl- (2,4, 6-trimethylbenzoyl) oxyphosphorus, 4g of hydroquinone and 5g of an antifoaming agent are stirred uniformly under the condition of keeping out of light to obtain photosensitive resin A3.
Example 4
Under the condition of avoiding light, 300g of urethane acrylate prepolymer SL-03 (with the number average molecular weight of 1000), 50g of polyethylene glycol 200 diacrylate, 35g of hydroxyethyl methacrylate, 16g of acryloyl morpholine, 8g of diphenyl- (2,4, 6-trimethylbenzoyl) oxyphosphorus, 4g of hydroquinone and 5g of defoaming agent are stirred uniformly to obtain the photosensitive resin A4.
Example 5
300g of urethane acrylate prepolymer SL-04 (number average molecular weight 1000), 50g of dipropylene glycol diacrylate, 35g of hydroxyethyl methacrylate, 16g of acryloylmorpholine, 8g of diphenyl- (2,4, 6-trimethylbenzoyl) oxyphosphorus, 4g of hydroquinone and 5g of an antifoaming agent were stirred uniformly under the condition of keeping out of light to obtain photosensitive resin A5.
A method for producing a rigid photosensitive resin composition based on urethane acrylate, comprising the steps of:
s1, a stirrer 1 is arranged, a charging barrel 2 is arranged on the stirrer 1, a cover 3 is arranged at the upper end of the charging barrel 2, and a light-shading space is formed between the charging barrel 2 and the cover 3 in a matching manner; 6 feeding machines 4 are arranged on the stirrer, each feeding machine 4 is provided with a discharge port, and each discharge port is arranged in the light-shading space; the 6 feeding machines are respectively a first feeding machine, a second feeding machine, a third feeding machine, a fourth feeding machine, a fifth feeding machine and a sixth feeding machine; the 6 feeding machines and the stirrer are electrically connected with a controller; putting polyurethane acrylate on a first feeding machine; feeding a difunctional alkene monomer onto a second feeding machine; feeding the monofunctional alkene monomer into a third feeding machine; putting the photoinitiator into a fourth feeding machine; putting the defoaming agent into a fifth feeding machine; putting the stabilizer into a sixth feeding machine;
s2, under the condition of keeping out of the sun, putting urethane acrylate into a light-proof space through a first feeding machine, putting a difunctional monomer into the light-proof space through a second feeding machine, putting the monofunctional monomer into the light-proof space through a third feeding machine, putting a photoinitiator into the light-proof space through a fourth feeding machine, putting an antifoaming agent into the light-proof space through a fifth feeding machine, and putting a stabilizing agent into the light-proof space through a sixth feeding machine;
s3, stirring uniformly by a stirrer 1 to obtain the photosensitive resin.
The controller is electrically connected with a photosensitive sensor 5, the photosensitive sensor 5 is installed in the light-shading space, and the controller is electrically connected with an input module; when the input module receives the control signal, the controller detects the light intensity inside the light-shading space through the photosensitive sensor; if the light intensity in the light-shading space is larger than a preset value, the controller stops the work of the 6 feeding machines; if the light intensity in the light-shading space is smaller than the preset value, the controller allows 6 feeding machines to feed materials. The amount of investment is controlled by the manufacturer. The input module is a combination of keys and a touch screen. The feeding machine 4 is a metering delivery pump.
Comparative example 1
Rigid resins for commercial use-brand of Yisheng
Comparative example 2
Rigid resin for commercial use-brand of Xin
Application example Performance testing
First, experiment method
1. Tensile strength
According to the international standard ISO, a dumbbell type spline model is drawn, the photosensitive resins of the examples 1-5 and the control groups 1-2 are used, a same-style photo-curing printer is used for printing dumbbell type test splines, a mechanical property test is carried out through a universal testing machine, the tensile rate is 10mm/min, each sample is measured in parallel for 5 times, and the average value is taken.
2. Bending strength
Drawing a rectangular sample strip model, printing a rectangular test sample strip by using photosensitive resins of examples 1-5 and a control group 1-2 and a photo-curing printer of the same model, carrying out mechanical property test by using a universal tester, wherein the compression rate is 10mm/min, each sample is subjected to parallel measurement for 5 times, and an average value is taken.
3. Shrinkage on polymerization
Under a test environment of 25 ℃, the density of the photosensitive resin of the examples 1 to 5 and the control groups 1 to 2 before curing and the density of the photosensitive resin after curing are tested by an electron densitometer, and the shrinkage can be obtained according to the following calculation formula:
4. viscosity measurement
The viscosities of the photosensitive resins of examples 1 to 5 and control groups 1 to 2 were measured by a digital viscometer with a rotor and a rotation speed selected as appropriate under a test environment of 25 ℃.
Second, experimental results
| Photosensitive resin system | Polymerization shrinkage | Tensile strength | Viscosity of the oil | Bending strength |
| C1 | ||||
| C2 | ||||
| A1 | ||||
| A2 | ||||
| A3 | ||||
| A4 | ||||
| A5 |
The invention has the beneficial effects that: good rigidity, low cost and easy production.
Claims (9)
1. A rigid photosensitive resin composition based on polyurethane acrylate is characterized by comprising the following components in parts by weight:
2. the rigid photosensitive urethane acrylate-based resin composition according to claim 1, wherein: 75 parts of urethane acrylate; 25 parts of difunctional alkene monomer; 20 parts of monofunctional alkene monomers; 0.1 part of photoinitiator; 0.1 part of defoaming agent; 0.1 part of stabilizer.
3. The rigid photosensitive urethane acrylate-based resin composition according to claim 1, wherein: the polyurethane acrylate prepolymer contains a carbamate group (-NH-COO-) in a molecular chain, and the number average molecular weight is 2000-8000.
4. The rigid photosensitive urethane acrylate-based resin composition according to claim 3, wherein: the polyurethane acrylate prepolymer is aliphatic polyurethane acrylate prepared from diisocyanate and polyglycol.
5. The rigid photosensitive urethane acrylate-based resin composition according to claim 4, wherein: the difunctional alkene monomer is one or more of acrylate monomers containing 2 functional groups, vinyl ether monomers containing 2 functional groups or 2 norbornene monomers.
6. The rigid photosensitive urethane acrylate-based resin composition according to claim 5, wherein: the acrylate monomers containing 2 functional groups include, but are not limited to, dipropylene glycol diacrylate, tricyclodecane dimethanol diacrylate, polyethylene glycol 200 diacrylate, polyethylene glycol 400 diacrylate, 1, 6-hexanediol diacrylate, tripropylene glycol diacrylate, tetra (ethylene glycol) diacrylate, and blends thereof.
7. The rigid photosensitive urethane acrylate-based resin composition according to claim 6, wherein: the acrylate monomer containing 2 functional groups is 1, 6-hexanediol diacrylate, tripropylene glycol diacrylate or dipropylene glycol diacrylate.
8. A method for producing a rigid photosensitive urethane acrylate-based resin composition, which is applied to the rigid photosensitive urethane acrylate-based resin composition according to any one of claims 1 to 7, comprising the steps of:
s1, a stirrer is arranged, a charging barrel is arranged on the stirrer, a cover is arranged at the upper end of the charging barrel, and a light-shading space is formed between the charging barrel and the cover in a matching manner; 6 feeding machines are arranged on the stirrer, each feeding machine is provided with a discharging port, and each discharging port is arranged in the light-shading space; the 6 feeding machines are respectively a first feeding machine, a second feeding machine, a third feeding machine, a fourth feeding machine, a fifth feeding machine and a sixth feeding machine; the 6 feeding machines and the stirrer are electrically connected with a controller; putting polyurethane acrylate on a first feeding machine; feeding a difunctional alkene monomer onto a second feeding machine; feeding the monofunctional alkene monomer into a third feeding machine; putting the photoinitiator into a fourth feeding machine; putting the defoaming agent into a fifth feeding machine; putting the stabilizer into a sixth feeding machine;
s2, under the condition of keeping out of the sun, putting urethane acrylate into a light-proof space through a first feeding machine, putting a difunctional monomer into the light-proof space through a second feeding machine, putting the monofunctional monomer into the light-proof space through a third feeding machine, putting a photoinitiator into the light-proof space through a fourth feeding machine, putting an antifoaming agent into the light-proof space through a fifth feeding machine, and putting a stabilizing agent into the light-proof space through a sixth feeding machine;
and S3, stirring uniformly by a stirrer to obtain the photosensitive resin.
9. The method for producing a rigid photosensitive resin composition based on urethane acrylate according to claim 8, wherein: the controller is electrically connected with a photosensitive sensor, the photosensitive sensor is installed in the light-shading space, and the controller is electrically connected with an input module; when the input module receives the control signal, the controller detects the light intensity inside the light-shading space through the photosensitive sensor; if the light intensity in the light-shading space is larger than a preset value, the controller stops the work of the 6 feeding machines; if the light intensity in the light-shading space is smaller than the preset value, the controller allows 6 feeding machines to feed materials.
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| CN202010926489.0A CN113174015A (en) | 2020-09-07 | 2020-09-07 | Rigid photosensitive resin composition based on polyurethane acrylate and production method thereof |
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| CN202010926489.0A CN113174015A (en) | 2020-09-07 | 2020-09-07 | Rigid photosensitive resin composition based on polyurethane acrylate and production method thereof |
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| CN108117624A (en) * | 2018-01-24 | 2018-06-05 | 中国科学院福建物质结构研究所 | A kind of preparation and application of the photosensitive resin of 3D printing containing POSS |
| CN110358040A (en) * | 2018-05-28 | 2019-10-22 | 岭南师范学院 | A kind of photocureable rapid shaping photosensitive resin composition |
| CN109517111A (en) * | 2018-09-30 | 2019-03-26 | 先临三维科技股份有限公司 | 3D printing method, 3D printing photocuring discoloration instruction resin and preparation method thereof |
| CN109535334A (en) * | 2018-10-30 | 2019-03-29 | 西安点云生物科技有限公司 | One kind is for quickly molding photosensitive resin of continuous liquid level and preparation method thereof |
| CN109776735A (en) * | 2019-01-25 | 2019-05-21 | 深圳锐沣科技有限公司 | For the molding optical solidified liquid resin of 3 D stereo |
| CN111116833A (en) * | 2019-12-30 | 2020-05-08 | 先临三维科技股份有限公司 | Resin composition for 3D printing, anti-oxygen polymerization-resistant resin, 3D printing product and preparation method |
| CN111251603A (en) * | 2020-02-07 | 2020-06-09 | 上海普利生机电科技有限公司 | Method for photocuring 3D printing using solid-state cured photosensitive resin |
| CN111378074A (en) * | 2020-04-17 | 2020-07-07 | 阜阳师范大学 | Three-arm acrylate polyurethane 3D printing photosensitive resin and preparation method thereof |
| CN111471139A (en) * | 2020-04-27 | 2020-07-31 | 孝感市易生新材料有限公司 | Soft photocuring 3D printing resin material and preparation method thereof |
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Application publication date: 20210727 |