CN104387755B - A kind of photosensitive resin and preparation method thereof - Google Patents
A kind of photosensitive resin and preparation method thereof Download PDFInfo
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- CN104387755B CN104387755B CN201410610090.6A CN201410610090A CN104387755B CN 104387755 B CN104387755 B CN 104387755B CN 201410610090 A CN201410610090 A CN 201410610090A CN 104387755 B CN104387755 B CN 104387755B
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Abstract
The invention belongs to 3D printing field of new materials, particularly belong to photosensitive resin field.The photosensitive resin is prepared including following weight percents component：Acrylate accounting, which weighs 5~80%, epoxy resin accounting and weighs 5~80%, radical initiator accounting and weigh 0.5~8%, cationic initiator accounting and weigh 0.5~5%, diluent accounting and weigh 5~50%, aerosil accounting, weighs 0.5~5%.The bending modulus and stretch modulus of the photosensitive resin of the present invention reach more than 2000Mpa, it is big that photosensitive resin resists flexural deformation stress in elastic limit, intensity is high, it is small to be deformed ability relativity, mechanical strength is big, greatly increases service life, and cubical contraction is 1.0% or so, extremely low cubical contraction is realized, meets industrial use requirement.
Description
Technical field
The invention belongs to 3D printing field of new materials, particularly belong to photosensitive resin field.
Background technology
Photocuring solid forming is using stereosopic printing (Stereo Lithography Apparatus, SLA) principle
A kind of technique and occur earliest, the most ripe and most widely used rapid prototyping technology of technology, by U.S. 3D Systems
Company releases in the late 1980s.The manufacturing process of SLA is to fill with liquid photosensitive resin in resin liquid bath, make its
Rapid curing under the irradiation of laser beam, when forming process starts, liftable workbench is in the next section thickness of liquid level
Highly, the laser beam after focusing under control of the computer, according to the requirement of cross section profile, is scanned along liquid level, makes to be swept
The resin solidification in region is retouched, so as to obtain the plastic tab of the cross section profile.Then, workbench declines the height of one layer of thin slice,
Cured plastic tab is new to cure to carry out second layer laser scanning curing just by one layer of new liquid resin institute head cover
One layer securely it is withered knot in preceding layer, so repeat endlessly, until entire product shaping finishes.
Presently used photocuring system is mostly ultraviolet system, is mainly used for industrial rapid prototyping, due to ultraviolet light meeting
Ozone, skin ambustion are generated, and can be caused serious injury to human eye, operating personnel need to be equipped with special labor and social security equipment, institute
Enter daily life to limit ultraviolet light cured article.
Invention content
The present invention mainly overcomes the injury hidden danger that ultraviolet light is brought, and the cured photosensitive tree of blue light can be based on by providing one kind
Fat without ultraviolet light, does not generate ozone, to skin without the effect of burning, improves the safety of product.
The purpose of the present invention is to provide a kind of photosensitive resins, and by weight percentage, the photosensitive resin includes following
Component：
The photosensitive resin is as 3D printing materials'use, and the acrylate is aromatic urethane acrylate, fat
At least one of fat adoption urethane acrylate.
Preferably, for cure the light source of the photosensitive resin be 440~490nm of wavelength blue light.
Preferably, the epoxy resin is at least one of epoxy acrylate, novolac epoxy resin.
Preferably, the radical initiator and cationic initiator are blue light sensitive initiator.
Preferably, the radical initiator is 2,6-, bis- fluoro- 3- pyrroles's phenyl titanocenes, benzophenone, styrax two
At least one of methyl ether, chlorinated diphenyl ketone, 2,4- diethyl thioxanthones.
Preferably, the cationic initiator is diaryl hexafluorophosphoric acid salt compounded of iodine, diaryl hexafluoroarsenate salt compounded of iodine, two
Aryl hexafluoro-antimonic acid salt compounded of iodine, triaryl hexafluorophosphoric acid salt compounded of iodine, triaryl hexafluoroarsenate salt compounded of iodine, triaryl hexafluoro-iodide antimonate
At least one of salt.
Preferably, the diluent is double pentaerythritol methacrylate, 1,6- hexanediyl esters, dipropylene glycol
At least one of diacrylate, polyethyleneglycol diacrylate.
Another object of the present invention is to provide a kind of preparation method of photosensitive resin, which includes following step
Suddenly：
(1) in the special glass there-necked flask equipped with blender and condenser pipe, sequentially add the acrylate 5 of formula ratio~
80 parts, 5~80 parts of epoxy resin, 0.5~8 part of radical initiator, 0.5~5 part of cationic initiator, 5~50 parts of diluent
Uniformly mixing, side mixing marginal not enter 0.5~5 part of aerosil；
(2) mixture that step (1) obtains is warming up to 60~75 DEG C, under the conditions of low whipping speed is 60-100 revs/min
20~30min is stirred, faint yellow uniform liquid is obtained, is kept in dark place, can as be based on the cured photosensitive resin of blue light.
Using above-mentioned photosensitive resin and preparation method thereof, the present invention has the following advantages：
(1) photosensitive resin of the invention is in use because with blue light illumination, generating ozone, will not skin ambustion,
The injury caused by human eye is reduced, the security risk brought using violet exposure is avoided, has promoted 3D printing in daily life
In application；
(2) bending modulus of photosensitive resin of the invention and stretch modulus reach more than 2000Mpa, and photosensitive resin exists
It resists that flexural deformation stress is big, and intensity is high in elastic limit, is deformed that ability relativity is small, and mechanical strength is big, greatly increase
Service life meets industrial use requirement；
(3) cubical contraction of photosensitive resin of the invention realizes extremely low cubical contraction 1.0% or so,
So that 3D printing product will not occur compared with large deformation in use because of contraction, for obtaining high-precision printed product
It is most important, conducive to the holding of shape of product；
(4) photosensitive resin prepared by the present invention has many advantages, such as that shaping speed is fast, mechanical strength is high, dimensional stability, this
Outer preparation process is simple, easy to utilize.
Specific embodiment
Below by way of specific embodiment, the present invention is further explained, but is not limited to following embodiments.
First, specific embodiment
Embodiment 1
1st, photosensitive resin raw material is configured according to the following ratio
2nd, preparation method
(1) in the special glass there-necked flask equipped with blender and condenser pipe, sequentially add 70 parts of urethane acrylate,
8 parts of epoxy acrylate, bis- fluoro- 1 part of 3- pyrroles's phenyl titanocenes of 2,6-, 0.5 part of benzophenone, six acrylic acid of bipentaerythrite
18 parts of ester is allowed to uniformly mix, and side mixing marginal not enters 2.5 parts of aerosil；
(2) mixture that step (1) obtains is warming up to 60 DEG C, low whipping speed stirs under the conditions of being 100 revs/min
25min obtains faint yellow uniform liquid, is sealed, and can as be based on the cured photosensitive resin of blue light.
Photosensitive resin made from above-mentioned preparation method with the blue light that wavelength is 440nm is cured, both obtains 3D printing product.
Embodiment 2
1st, photosensitive resin raw material is configured according to the following ratio
2nd, preparation method
(1) in the special glass there-necked flask equipped with blender and condenser pipe, sequentially add 35 parts of urethane acrylate,
15 parts of aliphatic urethane acrylate, 38 parts of novolac epoxy resin, 0.5 part of diaryl hexafluorophosphoric acid salt compounded of iodine, chlorinated diphenyl
5 parts of ketone, 5 parts of 1,6- hexanediyl esters are allowed to uniformly mix, and side mixing marginal not enters 1.5 parts of aerosil；
(2) mixture that step (1) obtains is warming up to 70 DEG C, low whipping speed stirs under the conditions of being 80 revs/min
20min obtains faint yellow uniform liquid, is sealed, and can as be based on the cured photosensitive resin of blue light.
Photosensitive resin made from above-mentioned preparation method with the blue light that wavelength is 450nm is cured, both obtains 3D printing product.
Embodiment 3
1st, photosensitive resin raw material is configured according to the following ratio
2nd, preparation method
(1) in the special glass there-necked flask equipped with blender and condenser pipe, aromatic urethane acrylic acid is sequentially added
5 parts of ester, 35 parts of epoxy acrylate, 45 parts of novolac epoxy resin, 4 parts of triaryl hexafluoroarsenate salt compounded of iodine, triaryl hexafluoro antimony
Sour 4 parts of salt compounded of iodine, 2 parts of dimethoxybenzoin, 4 parts of dipropylene glycol diacrylate are allowed to uniformly mix, and side mixing marginal not enters 1
The aerosil of part；
(2) mixture that step (1) obtains is warming up to 75 DEG C, low whipping speed stirs under the conditions of being 60 revs/min
30min is sealed, and obtains faint yellow uniform liquid, can as be based on the cured photosensitive resin of blue light.
Photosensitive resin made from above-mentioned preparation method with the blue light that wavelength is 490nm is cured, both obtains 3D printing product.
Embodiment 4
1st, photosensitive resin raw material is configured according to the following ratio
2nd, preparation method
(1) in the special glass there-necked flask equipped with blender and condenser pipe, sequentially add 80 parts of urethane acrylate,
5 parts of novolac epoxy resin, 3 parts of triaryl hexafluorophosphoric acid salt compounded of iodine, 1 part of 2,4- diethyl thioxanthones, two propylene of polyethylene glycol
5 parts of acid esters, 5 parts of 1,6- hexanediyl esters are allowed to uniformly mix, and side mixing marginal not enters 1 part of aerosil；
(2) mixture that step (1) obtains is warming up to 65 DEG C, low whipping speed stirs under the conditions of being 70 revs/min
20min obtains faint yellow uniform liquid, is sealed, and can as be based on the cured photosensitive resin of blue light.
Photosensitive resin made from above-mentioned preparation method with the blue light that wavelength is 455nm is cured, both obtains 3D printing product.
Embodiment 5
1st, photosensitive resin raw material is configured according to the following ratio
2nd, preparation method
(1) in the special glass there-necked flask equipped with blender and condenser pipe, sequentially add 21 parts of aliphatic acrylate,
15 parts of epoxy acrylate, 6 parts of triaryl hexafluoroarsenate salt compounded of iodine, 1 part of benzophenone, 2 parts of dimethoxybenzoin, double seasons penta
50 parts of six acrylate of tetrol is allowed to uniformly mix, and side mixing marginal not enters 5 parts of aerosil；
(2) mixture that step (1) obtains is warming up to 68 DEG C, low whipping speed stirs under the conditions of being 60 revs/min
30min obtains faint yellow uniform liquid, is sealed, and can as be based on the cured photosensitive resin of blue light.
Photosensitive resin made from above-mentioned preparation method with the blue light that wavelength is 460nm is cured, both obtains 3D printing product.
Embodiment 6
1st, photosensitive resin raw material is configured according to the following ratio
2nd, preparation method
(1) in the special glass there-necked flask equipped with blender and condenser pipe, aromatic urethane acrylic acid is sequentially added
5 parts of ester, 30 parts of epoxy acrylate, 30 parts of novolac epoxy resin, 2 parts of diaryl hexafluorophosphoric acid salt compounded of iodine, diaryl hexafluoro antimony
Sour 2 parts of salt compounded of iodine, 0.5 part of benzophenone, 30 parts of 1,6- hexanediyl esters are allowed to uniformly mix, and side mixing marginal not enters
0.5 part of aerosil；
(2) mixture that step (1) obtains is warming up to 60 DEG C, low whipping speed stirs under the conditions of being 100 revs/min
25min obtains faint yellow uniform liquid, is sealed, and can as be based on the cured photosensitive resin of blue light.
Photosensitive resin made from above-mentioned preparation method with the blue light that wavelength is 480nm is cured, both obtains 3D printing product.
Embodiment 7
1st, photosensitive resin raw material is configured according to the following ratio
2nd, preparation method
(1) in the special glass there-necked flask equipped with blender and condenser pipe, aromatic urethane acrylic acid is sequentially added
17 parts of ester, 23 parts of aliphatic urethane acrylate, 20 parts of epoxy acrylate, 27 parts of novolac epoxy resin, diaryl hexafluoro
1 part of phosphoric acid salt compounded of iodine, 4 parts of diaryl hexafluoro-antimonic acid salt compounded of iodine, 4 parts of chlorinated diphenyl ketone, double pentaerythritol methacrylate 0.5
Part, 0.5 part of dipropylene glycol diacrylate are allowed to uniformly mix, and side mixing marginal not enters 3 parts of aerosil；
(2) mixture that step (1) obtains is warming up to 70 DEG C, low whipping speed stirs under the conditions of being 75 revs/min
25min obtains faint yellow uniform liquid, is sealed, and can as be based on the cured photosensitive resin of blue light.
Photosensitive resin made from above-mentioned preparation method with the blue light that wavelength is 470nm is cured, both obtains 3D printing product.
Embodiment 8
1st, photosensitive resin raw material is configured according to the following ratio
2nd, preparation method
(1) in the special glass there-necked flask equipped with blender and condenser pipe, aromatic urethane acrylic acid is sequentially added
12 parts of ester, 10 parts of aliphatic urethane acrylate, 8 parts of aromatic urethane acrylate, 20 parts of epoxy acrylate, three virtues
3 parts of base hexafluorophosphoric acid salt compounded of iodine, 1 part of diaryl hexafluoro-antimonic acid salt compounded of iodine, 0.5 part of chlorinated diphenyl ketone, 2,4- diethyl thias
0.5 part of anthrone, 40 parts of polyethyleneglycol diacrylate are allowed to uniformly mix, and side mixing marginal not enters 2 parts of aerosil；
(2) mixture that step (1) obtains is warming up to 65 DEG C, low whipping speed stirs under the conditions of being 85 revs/min
20min obtains faint yellow uniform liquid, is sealed, and can as be based on the cured photosensitive resin of blue light.
Photosensitive resin made from above-mentioned preparation method with the blue light that wavelength is 475nm is cured, both obtains 3D printing product.
Embodiment 9
1st, photosensitive resin raw material is configured according to the following ratio
2nd, preparation method
(1) in the special glass there-necked flask equipped with blender and condenser pipe, aliphatic polyurethane acrylic acid is sequentially added
12 parts of ester, 45 parts of epoxy acrylate, 25 parts of novolac epoxy resin, bis- fluoro- 2 parts of 3- pyrroles's phenyl titanocenes of 2,6-, 2,4- bis-
0.5 part of ethyl thioxanthone, 7 parts of polyethyleneglycol diacrylate, 3 parts of dipropylene glycol diacrylate, bipentaerythrite 6 third
5 parts of olefin(e) acid ester is allowed to uniformly mix, and side mixing marginal not enters 0.5 part of aerosil；
(2) mixture that step (1) obtains is warming up to 75 DEG C, low whipping speed stirs under the conditions of being 95 revs/min
20min obtains faint yellow uniform liquid, is sealed, and can as be based on the cured photosensitive resin of blue light.
Photosensitive resin made from above-mentioned preparation method with the blue light that wavelength is 485nm is cured, both obtains 3D printing product.
2nd, performance test
Shore hardness
By the photosensitive resin sample obtained by embodiment 1-9 under the conditions of 23 ± 5 DEG C, measured with shore D type hardness testers.
Viscosity test
By the photosensitive resin sample obtained by embodiment 1-9 under the conditions of 25 DEG C, with II+Pro type viscosity of Bookfield DV-
It measures.
Photosensitive property is tested
The photosensitive property of photosensitive resin is the important indicator for characterizing photocuring characteristic, including critical solidification amount EcIt is deep with transmission
Spend Dp。EcRefer to that the photosensitive resin of the unit area under transmission depth reaches the minimum solidification energy needed for gel state；DpThen table
The relationship of cured thickness and luminous energy is levied.
By photosensitive resin sample made from embodiment 1-9 under the conditions of different laser scanning speeds and energy exposure, often
A embodiment makes different samples respectively, then tests the thickness of these samples respectively.With different thickness in each embodiment
Degree and energy make working curve, then the slope of curve is Dp, curve and X-axis intersection point are Ec。
Shrinking percentage is tested
With specific weight determine method, proportion when first testing photosensitive resin sample liquid made from above-described embodiment 1-9, calculation
It is as follows：
γ=G/V, wherein, γ represents proportion (unit g/cm3), (unit g), V represent volume (unit to G representation qualities
cm3)。
Sample proportion after being cured again with same procedure test, calculation are as follows：
γ '=G'/V'
Then shrinking percentage H=(γ '-γ)/γ × 100%
3rd, test result analysis
Sample made from above-described embodiment 1-9 is measured into shore hardness, viscosity, boundary solidification amount E respectivelyc, transmission depth Dp、
Bending modulus, stretch modulus, the data measured are as follows：
The experimental result that sample made from 1 embodiment 1-9 of table measures
As it can be seen from table 1 the bending modulus of photosensitive resin sample and stretch modulus reach made from embodiment 1-9
More than 2000Mpa, it follows that photosensitive resin is resisted in elastic limit, flexural deformation stress is big, and intensity is high, is deformed energy
Power relativity is small, and mechanical strength is big, and obtained 3D products are strong to extraneous resistance, greatly increase service life, meet industry
Change requirement.
The shore hardness of photosensitive resin sample reaches 60 degree or more made from embodiment 1-9, has reached medium hardness modeling
The hardness requirement of glue has ensured the formability of 3D products.
The critical solidification energy E of photosensitive resin sample made from embodiment 1-9cIn 10mJ/cm2Left and right, to curing light
It is relatively low according to energy requirement.Because blue light penetration capacity is strong, light energy is high, meets solidifying requirements with blue light illumination, conducive to curing molding.
The cubical contraction of photosensitive resin sample made from embodiment 1-9 realizes extremely low volume 1.0% or so
Shrinking percentage so that 3D printing product will not occur compared with large deformation in use because of contraction, high-precision for obtaining
Printed product is most important, conducive to the holding of shape of product.
The present invention prepares photosensitive resin has that shaping speed is fast, mechanical strength is high, dimensional stability etc. under blue light illumination
Advantage, preparation process is simple in addition, easy to utilize.Because blue light illumination is better than ultraviolet light, greatly reduce to ring around
The adverse effect in border improves the safety of product.
It will be apparent to those skilled in the art that technical solution that can be as described above and design, make other various
Corresponding change and deformation, and all these changes and deformation should all belong to the protection domain of the claims in the present invention
Within.
Claims (7)
1. a kind of photosensitive resin can be cured by blue light, be comprised the following components in percentage by weight：
The photosensitive resin is as 3D printing materials'use, and the acrylate is aromatic urethane acrylate, aliphatic
At least one of urethane acrylate, the epoxy resin are at least one in epoxy acrylate, novolac epoxy resin
Kind.
2. a kind of photosensitive resin according to claim 1, it is characterised in that：Light source for curing the photosensitive resin is
The blue light of 440~490nm of wavelength.
3. a kind of photosensitive resin according to claim 1, it is characterised in that：The radical initiator and cation cause
Agent is blue light sensitive initiator.
4. a kind of photosensitive resin according to claim 3, it is characterised in that：The radical initiator is fluoro- for 2,6- bis-
In 3- pyrroles's phenyl titanocenes, benzophenone, dimethoxybenzoin, chlorinated diphenyl ketone, 2,4- diethyl thioxanthones extremely
Few one kind.
5. a kind of photosensitive resin according to claim 4, it is characterised in that：The cationic initiator is diaryl hexafluoro
Phosphoric acid salt compounded of iodine, diaryl hexafluoroarsenate salt compounded of iodine, diaryl hexafluoro-antimonic acid salt compounded of iodine, triaryl hexafluorophosphoric acid salt compounded of iodine, three
At least one of aryl hexafluoroarsenate salt compounded of iodine, triaryl hexafluoro-antimonic acid salt compounded of iodine.
6. a kind of photosensitive resin according to claim 1, it is characterised in that：The diluent is six propylene of bipentaerythrite
At least one of acid esters, 1,6 hexanediol diacrylate, dipropylene glycol diacrylate, polyethyleneglycol diacrylate.
7. a kind of preparation method of photosensitive resin as described in claim 1, it is characterised in that：Include the following steps：
(1) in the special glass there-necked flask equipped with blender and condenser pipe, acrylate, the asphalt mixtures modified by epoxy resin of formula ratio are sequentially added
Fat, radical initiator, cationic initiator, diluent are allowed to uniformly mix, and side mixing marginal not enters the gas phase dioxy of formula ratio
SiClx；
(2) mixture that step (1) obtains is warming up to 60~75 DEG C, low whipping speed stirs under the conditions of being 60-100 revs/min
20~30min obtains faint yellow uniform liquid, is kept in dark place, and can as be based on the cured photosensitive resin of blue light.
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| CN104788625A (en) * | 2015-04-27 | 2015-07-22 | 北京印刷学院 | Free radical photo-curing material for manufacturing flexographic plate as well as preparation method and application of photo-curing material |
| CN105542628A (en) * | 2016-02-01 | 2016-05-04 | 深圳市思迈科新材料有限公司 | 3D (three dimensional) print light-cured resin composition and preparation method thereof |
| CN105754052B (en) * | 2016-03-02 | 2018-01-23 | 辽宁拜斯特复合材料有限公司 | A kind of 3D printing photocurable resin material and its preparation method and application |
| CN106243290B (en) * | 2016-05-11 | 2018-10-09 | 杭州乐一新材料科技有限公司 | A kind of rubber-type photocuring 3D printing material and preparation method thereof |
| CN105884981B (en) * | 2016-06-17 | 2019-01-18 | 湖南华曙高科技有限责任公司 | A kind of low-shrinkage light-cured resin for 3D printing |
| CN106749986A (en) * | 2016-12-12 | 2017-05-31 | 中山大简高分子材料有限公司 | A kind of epoxy phenolic resin composition for photocuring rapid prototyping |
| CN108410162B (en) * | 2018-04-13 | 2021-06-08 | 广州有得新材料科技有限公司 | Photocuring 3D printing material and preparation method and application thereof |
| CN110499130A (en) * | 2018-05-17 | 2019-11-26 | 深圳市绎立锐光科技开发有限公司 | Visible light curing adhesive and preparation method thereof |
| CN110724234B (en) * | 2018-06-28 | 2021-01-19 | 比亚迪股份有限公司 | Photosensitive resin composition for 3D printing, 3D printing forming method and 3D product |
| CN108976777A (en) * | 2018-07-04 | 2018-12-11 | 宁波市石生科技有限公司 | A kind of flexible material and its application for photocuring 3D printing |
| CN108841345B (en) * | 2018-07-09 | 2020-06-26 | 烟台德邦科技有限公司 | Hybrid curing photo-darkening acrylate adhesive |
| CN108546393A (en) * | 2018-07-19 | 2018-09-18 | 东莞蚂蚁三维科技有限公司 | A kind of resistance to ultralow temperature 3D printing photosensitive nanocomposite and its preparation |
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| C06 | Publication | ||
| PB01 | Publication | ||
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| CB03 | Change of inventor or designer information |
Inventor after: Liu Yaowen Inventor after: Xiong Ji Inventor after: Hang Haibo Inventor after: Dou Shouwen Inventor before: Liu Yaowen Inventor before: Hang Haibo Inventor before: Dou Shouwen |
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| COR | Change of bibliographic data | ||
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