CN106749942B - A kind of 3D printing ultraviolet photocureable material and preparation method thereof - Google Patents
A kind of 3D printing ultraviolet photocureable material and preparation method thereof Download PDFInfo
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- CN106749942B CN106749942B CN201611161848.8A CN201611161848A CN106749942B CN 106749942 B CN106749942 B CN 106749942B CN 201611161848 A CN201611161848 A CN 201611161848A CN 106749942 B CN106749942 B CN 106749942B
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- 239000000463 material Substances 0.000 title claims abstract description 48
- 238000010146 3D printing Methods 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 13
- 239000000178 monomer Substances 0.000 claims abstract description 13
- 229920002396 Polyurea Polymers 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 10
- 239000003085 diluting agent Substances 0.000 claims abstract description 9
- 102000004190 Enzymes Human genes 0.000 claims abstract description 8
- 108090000790 Enzymes Proteins 0.000 claims abstract description 8
- 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 8
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 7
- 239000002270 dispersing agent Substances 0.000 claims abstract description 7
- 239000003999 initiator Substances 0.000 claims abstract description 7
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 7
- 238000007711 solidification Methods 0.000 claims description 6
- 230000008023 solidification Effects 0.000 claims description 6
- 229920001400 block copolymer Polymers 0.000 claims description 3
- 102000004882 Lipase Human genes 0.000 claims description 2
- 108090001060 Lipase Proteins 0.000 claims description 2
- 239000004367 Lipase Substances 0.000 claims description 2
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 claims description 2
- 229930006711 bornane-2,3-dione Natural products 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 235000019421 lipase Nutrition 0.000 claims description 2
- 229920000058 polyacrylate Polymers 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 230000009477 glass transition Effects 0.000 claims 2
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 claims 1
- CWXZAJNUTOBAOI-UHFFFAOYSA-N 1-(2,3-dimethoxyphenyl)-2-hydroxy-2-phenylethanone Chemical compound COC1=CC=CC(C(=O)C(O)C=2C=CC=CC=2)=C1OC CWXZAJNUTOBAOI-UHFFFAOYSA-N 0.000 claims 1
- JHQMEZRRZJJNAI-UHFFFAOYSA-N [(2-methylphenyl)-phenylphosphoryl]-phenylmethanone Chemical compound CC1=CC=CC=C1P(=O)(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 JHQMEZRRZJJNAI-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 238000000016 photochemical curing Methods 0.000 abstract description 13
- 238000001723 curing Methods 0.000 abstract description 11
- 230000005764 inhibitory process Effects 0.000 abstract description 5
- 230000009257 reactivity Effects 0.000 abstract description 4
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 238000011161 development Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 235000015511 Liquidambar orientalis Nutrition 0.000 description 1
- 239000004870 Styrax Substances 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- VGQLLUIFOUVAPI-UHFFFAOYSA-N [Cl].OC(=O)C=C Chemical compound [Cl].OC(=O)C=C VGQLLUIFOUVAPI-UHFFFAOYSA-N 0.000 description 1
- -1 allyl ester Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 125000002362 bornane-2,3-dione group Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000805 composite resin Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000010437 gem Substances 0.000 description 1
- 229910001751 gemstone Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B33—ADDITIVE MANUFACTURING TECHNOLOGY
- B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
- B33Y70/00—Materials specially adapted for additive manufacturing
-
- 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
Abstract
The invention belongs to 3D printing technique fields, and in particular to a kind of 3D printing ultraviolet photocureable material and preparation method thereof；The material includes following component: 25~50 parts by weight of aliphatic epoxy acrylate；20~40 parts by weight of aliphatic urethane acrylate；0~25 parts by weight of polyurea monomers；15~30 parts by weight of reactive diluent；0.05~1 parts by weight of initiator；Solidify 0.15~2 parts by weight of enzyme；0.3~3 parts by weight of dispersing agent；0.1~1.5 parts by weight of levelling agent.The photo-curing material has the advantages that elasticity is good, color inhibition；Reactivity with higher and curing rate；Curing materials of the invention have the advantages that good toughness, adhesive force are strong, reactivity is high, curing rate is fast；With great market prospects and economic value.
Description
Technical field
The invention belongs to 3D printing technique fields, and in particular to a kind of 3D printing ultraviolet photocureable material and its preparation side
Method.
Background technique
Quick forming fabri-cation is also in 3D printing, is known as the new industry of " leading the third time industrial revolution ".In numerous 3D
In printing shaping technique, SLA (stereo laser solidifies) is a kind of environmentally protective curing technology, have environmental-friendly, energy consumption less,
The advantages that quick solidifying, precision are high, cured product performance is excellent, be widely used in jewel design, building, medical instrument, automobile,
The industries such as aerospace are a kind of current quick molding methods most widely used on the market.
Break foreign technology monopolization and determine the protective barrier that machine is expected surely, promotes production domesticization 3D printing technique UV Stereolithography
Development, exploitation low viscosity, curing rate is fast, shrinking percentage is small, the 3D printing photosensitive resin of good mechanical performance is domestic development
The inexorable trend of UV photo-curing material.
Photo-curing material refers to the cured resin material under specific light (ultraviolet light) photograph as its name suggests.Not due to the material
It needs the processing technologys such as heating, high pressure, but by being layering into preset model, therefore can have that matter is crisp, mechanical property
The defect of difference is to limit its large-scale application.Based on this, domestic and foreign scholars are by the methods of activeness and quietness to photocuring material
The mechanical property of material is modified.It is photosensitive that CN104629231A discloses free radical initiation allyl ester resin composite glass fiber
Resin, obtained photo-curing material has good intensity and rigidity, but content of glass fiber is excessively high to be made in its resin
It is uneven in dispersion, and hard and crisp also it is unfavorable for large-scale promotion；CN104893224A discloses polyether acrylate or polycyclic
Modified (branching) polyether acrylate of amine is the 3D printing material that raw material is prepared, and the cure shrinkage of material is small, xanthochromia
Small, hardness and flexibility are moderate.
In order to improve 3D printing photo-curing material flexibility, expands the application field of photo-curing material, develop curing rate
Fastly, shrinking percentage is small, color inhibition, the 3D printing that elasticity is good become the inevitable requirement of era development with photo-curing material.
Summary of the invention
For this purpose, technical problem to be solved by the present invention lies in overcome existing photo-curing material viscosity is high, curing rate is slow,
The technical bottlenecks such as shrinking percentage is low, develop that a kind of curing rate is fast, shrinking percentage is small, color inhibition, the 3D printing photocuring that elasticity is good
Material.
In order to solve the above technical problems, a kind of 3D printing ultraviolet photocureable material of the invention, the material includes as follows
Component:
Preferably, the degree of functionality of the aliphatic epoxy acrylate is 2, and viscosity is 1100cps under room temperature, and vitrifying turns
Temperature is 40 DEG C.
Preferably, the degree of functionality of the aliphatic urethane acrylate is 4, and viscosity is 4500cps, vitrifying under room temperature
Transition temperature is 33 DEG C.
Preferably, the viscosity of the polyurea monomers at normal temperature is 2000-3000cps, and elongation at break is greater than 600%.
Preferably, the reactive diluent is in tripropylene glycol class diacrylate or trimethylolpropane trimethacrylate
One or two.
Preferably, the initiator is camphorquinone, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, styrax diformazan
One or both of ether.
Preferential, the solidification enzyme is that the solidification enzyme is lipase.
Preferably, the dispersing agent be amino modified block copolymer, in polybasic carboxylic acid based block copolymer at least
It is a kind of.
Preferably, the levelling agent is polyacrylate.
The invention also discloses the preparation methods of any one ultraviolet photocureable material, which is characterized in that the method
Are as follows:
A, prepared by polyurea monomers: take acryloyl chloride, in sodium hydroxide and it is rear be added 50% toluene solvant, through washing,
Polyurea monomers are made after dehydration, separation；
B, in the reaction kettle equipped with blender, thermometer, condenser and charging spout, aliphatic epoxy acrylic acid is added
Ester, aliphatic urethane acrylate and polyurea monomers and reactive diluent, stirring；
C, dispersing agent, levelling agent in a kettle, is added, stirs evenly；
D, toward addition initiator inside reaction kettle and solidification enzyme, temperature of reaction kettle is 40-60 DEG C, to the transparent color of solution
Stop stirring afterwards.
The above technical solution of the present invention has the following advantages over the prior art: the present invention is poly- using the long-chain of low viscosity
Urethane acrylate and epoxy acrylate are oligomer, and UV photo-curing material of the invention is made to have high-flexibility and attachment
Power；The addition of acrylic acid chlorine modified polyurea monomer, makes photo-curing material of the invention have the advantages that elasticity is good, color inhibition；With
TPGDA bifunctional imparts the higher reactivity of material and curing rate as diluent；Curing materials of the invention
Have the advantages that good toughness, color inhibition, reactivity are high, curing rate is fast；With great market prospects and economic value.
Specific embodiment
Embodiment
Embodiment 1: present embodiment discloses a kind of 3D printing ultraviolet photocureable material, specific ingredient is as follows:
Embodiment 2: present embodiment discloses a kind of 3D printing ultraviolet photocureable material, specific ingredient is as follows:
Embodiment 3: present embodiment discloses a kind of 3D printing ultraviolet photocureable material, specific ingredient is as follows:
Embodiment 4: present embodiment discloses a kind of 3D printing ultraviolet photocureable material, specific ingredient is as follows:
Embodiment 5: present embodiment discloses a kind of 3D printing ultraviolet photocureable material, specific ingredient is as follows:
Embodiment 6: present embodiment discloses a kind of 3D printing ultraviolet photocureable material, specific ingredient is as follows:
Embodiment 7: present embodiment discloses a kind of 3D printing ultraviolet photocureable material, specific ingredient is as follows:
Present embodiment discloses the preparation methods of ultraviolet photocureable material described in embodiment 1-7 for embodiment 8:
1) preparation of polyurea monomers: acryloyl chloride, in sodium hydroxide and it is rear be added 50% toluene solvant, through washing,
Required polyurea monomers are made after dehydration, separation；
2) according to the ratio requirement of each embodiment, each raw material is weighed；
3) it in the reaction kettle equipped with blender, thermometer, condenser and charging spout, is matched according to experiment and oligomer is added
Aliphatic epoxy acrylate aliphatic urethane acrylate and modified polyurea monomer and reactive diluent, after mixing evenly；
4) in the reaction kettle equipped with monomer and diluent, it is slowly added to dispersing agent, levelling agent, is stirred evenly；
5) toward addition initiator inside reaction kettle and solidification enzyme, temperature of reaction kettle is heated to 40-60 DEG C, transparent to solution
Stop stirring up to target product after color, be fitted into black plastic bottle after being down to room temperature.
Photo-curing material prepared by embodiment is placed in 3D printer and carries out printing test by experimental example, solid to 3D printing light
The performance for changing solid material and shaped article is tested, and test result is as shown in table 1:
Table 1
Obviously, the above embodiments are merely examples for clarifying the description, and does not limit the embodiments.It is right
For those of ordinary skill in the art, can also make on the basis of the above description it is other it is various forms of variation or
It changes.There is no necessity and possibility to exhaust all the enbodiments.And it is extended from this it is obvious variation or
It changes still within the protection scope of the invention.
Claims (10)
1. a kind of 3D printing ultraviolet photocureable material, which is characterized in that the material includes following component:
25~50 parts by weight of aliphatic epoxy acrylate；
20~40 parts by weight of aliphatic urethane acrylate；
5~25 parts by weight of polyurea monomers；
15~30 parts by weight of reactive diluent；
0.05~1 parts by weight of initiator；
Solidify 0.15~2 parts by weight of enzyme；
0.3~3 parts by weight of dispersing agent；
0.1~1.5 parts by weight of levelling agent.
2. ultraviolet photocureable material as described in claim 1, which is characterized in that the function of the aliphatic epoxy acrylate
Degree is 2, and viscosity is 1100cps under room temperature, and glass transition temperature is 40 DEG C.
3. ultraviolet photocureable material as claimed in claim 2, which is characterized in that the official of the aliphatic urethane acrylate
Energy degree is 4, and viscosity is 4500cps under room temperature, and glass transition temperature is 33 DEG C.
4. ultraviolet photocureable material as claimed in claim 3, which is characterized in that the viscosity of the polyurea monomers at normal temperature is
2000-3000cps。
5. ultraviolet photocureable material as claimed in claim 4, which is characterized in that the reactive diluent is tripropylene glycol dipropyl
One or both of olefin(e) acid ester or trimethylolpropane trimethacrylate.
6. ultraviolet photocureable material as claimed in claim 5, which is characterized in that the initiator be camphorquinone, 2,4,6- tri-
One or both of methyl benzoyl diphenyl phosphine oxide, dimethoxybenzoin.
7. ultraviolet photocureable material as claimed in claim 6, which is characterized in that the solidification enzyme is lipase.
8. ultraviolet photocureable material as claimed in claim 7, which is characterized in that the dispersing agent is total for amino modified block
At least one of polymers, polybasic carboxylic acid based block copolymer.
9. ultraviolet photocureable material as claimed in claim 8, which is characterized in that the levelling agent is polyacrylate.
10. a kind of preparation method of such as described in any item ultraviolet photocureable materials of claim 1-9, which is characterized in that described
Method are as follows:
A, in the reaction kettle equipped with blender, thermometer, condenser and charging spout, aliphatic epoxy acrylate, rouge is added
Fat adoption urethane acrylate and polyurea monomers and reactive diluent, stirring；
B, dispersing agent, levelling agent in a kettle, is added, stirs evenly；
C, toward addition initiator inside reaction kettle and solidification enzyme, temperature of reaction kettle is 40-60 DEG C, is stopped after the transparent color of solution
Only stir.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201611161848.8A CN106749942B (en) | 2016-12-15 | 2016-12-15 | A kind of 3D printing ultraviolet photocureable material and preparation method thereof |
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| CN201611161848.8A CN106749942B (en) | 2016-12-15 | 2016-12-15 | A kind of 3D printing ultraviolet photocureable material and preparation method thereof |
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| CN106749942B true CN106749942B (en) | 2019-03-12 |
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Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108587100A (en) * | 2018-05-18 | 2018-09-28 | 深圳永昌和科技有限公司 | Environment and human body friendly vegetable oil base ultraviolet light cure 3D printing resin |
| CN108690327A (en) * | 2018-05-29 | 2018-10-23 | 上海云铸三维科技有限公司 | A kind of 3D printing UV curing photosensitive resin and preparation method thereof |
| CN108690328A (en) * | 2018-05-29 | 2018-10-23 | 上海云铸三维科技有限公司 | A kind of photosensitive resin and preparation method thereof for 3D printing |
| CN111534244B (en) * | 2020-05-12 | 2022-07-05 | 江西蓝海芯科技集团有限公司 | Protective film applied to curved surface display screen |
| CN112250831B (en) * | 2020-10-12 | 2022-11-25 | 深圳飞扬骏研新材料股份有限公司 | UV resin and preparation method thereof |
| CN114573763B (en) * | 2022-03-22 | 2023-11-17 | 广州黑格智造信息科技有限公司 | 3D printing photo-curing material for dental model and preparation method thereof |
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| CN105199058A (en) * | 2015-09-30 | 2015-12-30 | 惠州市安品新材料有限公司 | 3D printing light-cured resin composition and modeling matter prepared from same |
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| CN106749942A (en) | 2017-05-31 |
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Denomination of invention: A UV curing material for 3D printing and its preparation method Effective date of registration: 20210422 Granted publication date: 20190312 Pledgee: Shenzhen hi tech investment small loan Co.,Ltd. Pledgor: SHENZHEN FEIYANG XINGYE TECHNOLOGY Co.,Ltd. Registration number: Y2021980002908 |