CN112812241A - Controlled-activity photocuring 3D printing resin and preparation method and application thereof - Google Patents

Controlled-activity photocuring 3D printing resin and preparation method and application thereof Download PDF

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Publication number
CN112812241A
CN112812241A CN202110087359.7A CN202110087359A CN112812241A CN 112812241 A CN112812241 A CN 112812241A CN 202110087359 A CN202110087359 A CN 202110087359A CN 112812241 A CN112812241 A CN 112812241A
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acrylate
parts
polymerization inhibitor
activity
controlled
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杨义浒
王李
陈锐
徐建明
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Xiaogan Esun New Material Co ltd
Isun3d Tech Shenzhen Co ltd
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Xiaogan Esun New Material Co ltd
Isun3d Tech Shenzhen Co ltd
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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
    • C08F283/10—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers containing more than one epoxy radical per molecule
    • C08F283/105—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers containing more than one epoxy radical per molecule on to unsaturated polymers containing more than one epoxy radical per molecule
    • 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
    • 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

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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)
  • Engineering & Computer Science (AREA)
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Abstract

The invention belongs to the technical field of photosensitive resin, and particularly relates to photocuring 3D printing resin with controlled activity, and a preparation method and application thereof. The activity-controlled photocuring 3D printing resin comprises the following components in parts by weight: 30-50 parts of oligomeric acrylate, 0.1-2 parts of polymerization inhibitor, 0.5-4 parts of photoinitiator, 20-40 parts of reactive diluent, 0-5 parts of pigment and filler and 0.2-1 part of auxiliary agent. The technical scheme provided by the invention improves the forming precision of 3D printing light-cured resin and solves the problem of residue in the printing process of a black-and-white screen LCD printer; meanwhile, the problem of complete molding of the resin on a color screen LCD printer, a DLP printer and an SLA printer is solved.

Description

Controlled-activity photocuring 3D printing resin and preparation method and application thereof
Technical Field
The invention belongs to the technical field of photosensitive resin, and particularly relates to photocuring 3D printing resin with controlled activity, and a preparation method and application thereof.
Background
The photosensitive resin is found for nearly two hundred years till now and goes from a natural resin stage to an artificial resin stage; the field of application also evolves from photographic cardboard technology to photolithography. The photocuring 3D printing technology is started in the 80 th 20 th century, and gradually develops and forms subdivided molding modes such as SLA, DLP, LCD, Polyjet and the like after decades of development. The LCD forming technology has been rapidly developed due to low technical threshold and low equipment cost.
Compared with DLP forming technology, the LCD photocuring printer has DLP light source replaced with LCD, and the LCD liquid crystal board imaging principle is that the light is projected through red, green and blue filters to filter out infrared ray and ultraviolet ray, and the three primary colors are projected through three liquid crystal boards for combined projection imaging. LCD 3D printer in the market mainly adopts the light source scheme of perpendicular chip LED emission light source plus bowl, and the LCD screen mainly adopts the various screen of RGB. The consequence of this is that after the ultraviolet light passes through the LCD screen, the central optical power of the light source is high, and the peripheral optical power is low, resulting in a large size deviation in a model (± 0.05mm) with a high print size requirement precision due to different optical power at different positions and different ultraviolet energy absorbed by the resin during the curing process.
With the technical progress of LCD printing equipment and the use requirements of terminal customers, black and white screen 3D printers are gradually introduced by current mainstream printer manufacturers in recent years. The black-white screen 3D printer adopts black-white monochromatic imaging display technology, and light can directly evenly shine black-white screen, can improve the utilization ratio of light under the same power, and the penetration rate of purple light is higher than 3 ~ 4 times of the various screen of RGB under the same condition, and it is efficient to print, and the printing precision is high, and the radiating effect of printing process is good. The increase in printing speed is actually reflected by the reduction in exposure time, and compared to the conventional color screen, the transmittance of the black and white screen is greatly increased (the color filter and the backlight are removed, the polarizer is optimally adjusted, and the aperture opening ratio is optimally adjusted), so that the light source can provide the energy required by resin curing in a shorter time.
Compared with the conventional color screen, the black-white screen has the following characteristics:
1. the higher light transmittance is improved to 6 percent from about 1 percent of the color screen;
2. the printing speed is higher, the single-layer exposure time is generally 2-4s, and the printing speed is 1/4-1/2 of a color screen type;
3. longer screen life, typically at least 3000 hours for the screen. The large-format black-and-white screen printer has an industrial molding size and can meet more demands of the market.
The black-and-white screen printer has the important significance of greatly shortening the printing time and improving the printing efficiency, and particularly, the large-format LCD printer matched with a 2K/4K resolution screen meets the requirement of the market on large size, so that the LCD technology is important to industrial production, the gap between the LCD technology and industrial-grade SLA is shortened, and the use cost is reduced.
While black and white screen LCD printers have the above advantages, they also present some significant problems. Resin suitable for color screen printers in the market has the fatal problem of easily producing residues on black and white screen printers, particularly large-format equipment, the residue problem is more prominent, the use experience of terminal customers is seriously influenced, and the existing resin cannot be suitable for the black and white screen printers, particularly the large-format black and white screen printers.
This patent control photocuring 3D prints active method of resin, has overcome the defect that above-mentioned printing apparatus exists, has solved the residue problem that current resin printed the existence on black and white screen printer, has also improved the shaping precision that the model was printed to the resin simultaneously on traditional color screen printer.
Disclosure of Invention
In order to solve the defects of the prior art and overcome the defects of the prior printing material, the invention provides a photocuring 3D printing resin with controlled activity and a preparation method and application thereof. The technical scheme provided by the invention improves the forming precision of 3D printing light-cured resin and solves the problem of residue in the printing process of a black-and-white screen LCD printer; meanwhile, the problem of complete molding of the resin on a color screen LCD printer, a DLP printer and an SLA printer is solved.
The technical scheme provided by the invention is as follows:
a controlled-activity photocuring 3D printing resin comprises the following components in parts by weight: the paint comprises the following components in parts by weight: 30-50 parts of oligomeric acrylate, 0.1-2 parts of polymerization inhibitor, 0.5-4 parts of photoinitiator, 20-40 parts of reactive diluent, 0-5 parts of pigment and filler and 0.2-1 part of auxiliary agent, wherein the oligomeric acrylate is selected from one or more of polyurethane acrylate, polyurethane methacrylate, epoxy acrylate and epoxy methacrylate, the reactive diluent is selected from one or more of acrylate and acryloyl morpholine, the photoinitiator is a free radical type photoinitiator, and the polymerization inhibitor is a free radical polymerization inhibitor.
The activity-controlled photocuring 3D printing resin provided by the technical scheme has the advantages that the addition and content control of the polymerization inhibitor can ensure that the resin in the non-exposure area can not penetrate through the whole screen due to extremely weak blue light in the printing process, and the phenomenon that residues generated by curing are attached to the release film after long-time accumulation is avoided. Therefore, the problem that residues are easy to appear when the existing resin is printed on a black-white screen printer, particularly a large-format black-white screen printer, is solved, and the original printing performance of the printing resin is not influenced.
The cured resin obtained by curing the activity-controlled photocuring 3D printing resin provided by the technical scheme contains
Figure BDA0002911372370000031
And/or
Figure BDA0002911372370000032
And (5) structure.
Specifically, the polymerization inhibitor is a polymerization inhibitor A and/or a polymerization inhibitor B:
the polymerization inhibitor A is selected from N, N '- (hexane-1, 6-diyl) bis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionamide ], N' -bis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionyl ] hydrazine, distyrylbis benzoxazole, 2, 5-bis (5-tert-butyl-2-benzoxazolyl) thiophene, 2- (2H-benzotriazol-2-yl) -4, 6-di-tert-amylphenol, 2- (2-hydroxy-5-tert-octylphenyl) benzotriazole, bis (1,2,2,6, 6-pentamethyl-4-piperidine) sebacate; one or more of 1- (methyl) -8- (1,2,2,6, 6-pentamethyl-4-piperidine) sebacate;
the polymerization inhibitor B is selected from one or more of hydroxyanisole, hydroquinone, 2- (4, 6-diphenyl-1, 3, 5-triazine-2) -5-n-hexylalkoxyphenol and 4- (2-benzoxazolyl) -4' - (5-methyl-2-benzoxazolyl) stilbene.
The polymerization inhibitor provided by the technical scheme is mainly from polymerization inhibitors used in plastic synthesis. The inventors have found that the polymerization inhibitor has advantages of lowering resin activity, improving model resolution, and reducing residues, compared with other polymerization inhibitors. Therefore, the above-mentioned polymerization inhibitors are selected.
Specifically, the oligomeric acrylate is at least one selected from urethane acrylate, urethane methacrylate, epoxy acrylate or epoxy methacrylate, the urethane acrylate/urethane methacrylate can be aliphatic urethane acrylate, aromatic urethane acrylate, aliphatic urethane methacrylate or aromatic urethane methacrylate, and the epoxy acrylate/epoxy methacrylate can be modified epoxy acrylate, modified bisphenol a epoxy acrylate, modified epoxy methacrylate or modified bisphenol a epoxy methacrylate.
Specifically, the auxiliary agent is selected from any one or more of a leveling agent, a defoaming agent and a wetting dispersing agent.
Specifically, the reactive diluent is at least one selected from the group consisting of acrylate and morpholine, the acrylate may be hydroxyethyl acrylate, hydroxypropyl acrylate, 4-hydroxybutyl acrylate, lauryl acrylate, isobornyl methacrylate, trimethylolpropane formal acrylate, 4-tert-butylcyclohexyl acrylate, tetrahydrofuran methacrylate, N-dimethylacrylamide, tripropylene glycol diacrylate, 1, 6-hexanediol diacrylate, propoxylated neopentyl glycol diacrylate, tricyclodecane dimethanol diacrylate, polyethylene glycol (200) diacrylate, dipropylene glycol diacrylate, ethoxylated trimethylolpropane triacrylate, propoxylated glycerol triacrylate, ethoxylated pentaerythritol tetraacrylate, ethoxylated trimethylolpropane triacrylate, propylene glycol triacrylate, hydrogenated pentaerythritol tetraacrylate, propylene glycol diacrylate, propylene glycol, Dipentaerythritol hexaacrylate, wherein the morpholine can be N-methylmorpholine, N-formylmorpholine, N-acetylmorpholine, acryloyl morpholine and N-methylmorpholine oxide; preferably, the reactive diluent is tripropylene glycol diacrylate, ethoxylated trimethylolpropane triacrylate, acryloylmorpholine.
Specifically, the free radical type photoinitiator is at least one selected from thioxanthone, acylphosphine oxide and dialkoxyacetophenone. Preferably, the radical photoinitiator is isopropyl thioxanthone, diphenyl (2,4, 6-trimethylbenzoyl) phosphine oxide, 2-diethoxyacetophenone.
Specifically, the pigment and filler is selected from organic color paste or/and inorganic color paste. Preferably, the color paste is red, yellow or white paste.
The invention also provides a preparation method of the activity-controlled photocuring 3D printing resin, which comprises the following steps: according to the amount of the formula, the components are heated and stirred uniformly, the heating temperature is 30-90 ℃, and the heating time is not less than 0.5h, so that the Chinese medicinal composition is obtained.
The invention also provides application of the photocuring 3D printing resin with controlled activity, and the photocuring resin can be used as a photocuring resin material for black-and-white screen LCD printers, a photocuring resin material for color screen LCD printers, a photocuring resin material for DLP printers or a photocuring resin material for SLA printers.
The technical scheme provided by the invention improves the forming precision of 3D printing light-cured resin and solves the problem of residue in the printing process of a black-and-white screen LCD printer; meanwhile, the problem of complete molding of the resin on a color screen LCD printer, a DLP printer and an SLA printer is considered, so that the resin can be used as a printing material of the various printers.
Drawings
FIG. 1 is an optical photograph of a resin provided in the prior art printed over-exposed residue on a black and white screen printer.
FIG. 2 is an optical photograph of a residue-free model printed on a black and white screen printer with the resin provided by the present invention.
Detailed Description
The principles and features of this invention are described below in conjunction with examples which are set forth to illustrate, but are not to be construed to limit the scope of the invention.
Example 1
Light-curable resin (A)
The oligomeric acrylate is prepared from sandoman CN 10440 parts, the active diluent is prepared from tripropylene glycol diacrylate 36 parts and ethoxylated trimethylolpropane triacrylate 20 parts, the free radical photoinitiator is prepared from 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide 4 parts, the color paste is prepared from black 0.024 parts, white 0.4 parts and blue 0.03 parts, and no polymerization inhibitor is added, and the mixture is heated in a water bath at 60 ℃ and stirred for 30min to obtain the photocuring resin (A).
Example 2
Light-curable resin (B)
In contrast to example 1, 0.4 part of N, N' - (hexane-1, 6-diyl) bis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionamide ] was added as a polymerization inhibitor.
Table 1: comparison of printing results
TABLE 1
Figure BDA0002911372370000061
Example 3
Light-curable resin (C)
The difference from example 2 is that 583-1 parts of double bonds are used as oligomeric acrylates.
Example 4
Light-curing resin (D)
The diluent monomers different from the monomer in the embodiment 2 are 36 parts of acryloyl morpholine and 26 parts of diethylene glycol dimethacrylate.
Table 2: comparison of printing results
TABLE 2
Figure BDA0002911372370000071
Example 5
Light-curable resin (E)
The difference from example 2 was that 0.4 part of N, N '- (hexane-1, 6-diyl) bis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionamide ] and 0.1 part of 4- (2-benzoxazolyl) -4' - (5-methyl-2-benzoxazolyl) stilbene were used as the polymerization-inhibiting auxiliary.
Example 6
Light-curable resin (F)
Different from example 3, the polymerization inhibitor is 0.4 part of 2- (2H-benzotriazole-2-yl) -4, 6-di-tert-amylphenol and 0.1 part of 2- (4, 6-diphenyl-1, 3, 5-triazine-2) -5-n-hexylalkoxyphenol.
Table 3: comparison of printing results
TABLE 3
Figure BDA0002911372370000081
The comparison of the results of the light-cured resins (E) and (F) shows that different polymerization inhibiting auxiliary agents have different influences on the molding precision of the model.
Example 7
Light-curable resin (G)
The difference from example 5 was that 0.5 part of N, N '- (hexane-1, 6-diyl) bis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionamide ] and 0.3 part of 4- (2-benzoxazolyl) -4' - (5-methyl-2-benzoxazolyl) stilbene were used as the polymerization-inhibiting auxiliary.
Table 4: comparison of printing results
TABLE 4
Figure BDA0002911372370000082
Comparison of the results of the photocurable resins (E) and (G) shows that the resolution of the model can be improved by appropriately increasing the amount of the polymerization inhibitor.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.

Claims (8)

1. The activity-controlled photocuring 3D printing resin is characterized by comprising the following components in parts by weight: 30-50 parts of oligomeric acrylate, 0.1-2 parts of polymerization inhibitor, 0.5-4 parts of photoinitiator, 20-40 parts of reactive diluent, 0-5 parts of pigment and filler and 0.2-1 part of auxiliary agent, wherein the oligomeric acrylate is selected from one or more of polyurethane acrylate, polyurethane methacrylate, epoxy acrylate and epoxy methacrylate, the reactive diluent is selected from one or more of acrylate and acryloyl morpholine, the photoinitiator is a free radical type photoinitiator, and the polymerization inhibitor is a free radical polymerization inhibitor.
2. The activity-controlled photocurable 3D printing resin as claimed in claim 1, characterized in that:
the polymerization inhibitor is polymerization inhibitor A or polymerization inhibitor B, or the mixture of polymerization inhibitor A and polymerization inhibitor B:
the polymerization inhibitor A is selected from N, N '- (hexane-1, 6-diyl) bis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionamide ], N' -bis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionyl ] hydrazine, distyrylbis benzoxazole, 2, 5-bis (5-tert-butyl-2-benzoxazolyl) thiophene, 2- (2H-benzotriazol-2-yl) -4, 6-di-tert-amylphenol, 2- (2-hydroxy-5-tert-octylphenyl) benzotriazole, bis (1,2,2,6, 6-pentamethyl-4-piperidine) sebacate; any one or more of 1- (methyl) -8- (1,2,2,6, 6-pentamethyl-4-piperidine) sebacate;
the polymerization inhibitor B is any one or more of hydroxyanisole, hydroquinone, 2- (4, 6-diphenyl-1, 3, 5-triazine-2) -5-n-hexylalkoxyphenol and 4- (2-benzoxazolyl) -4' - (5-methyl-2-benzoxazolyl) stilbene.
3. The activity-controlled photocurable 3D printing resin as claimed in claim 2, characterized in that: the oligomeric acrylic ester is selected from any one or mixture of more of aliphatic polyurethane acrylic ester, aromatic polyurethane acrylic ester, aliphatic polyurethane methacrylic ester, aromatic polyurethane methacrylic ester, modified epoxy acrylic ester, modified bisphenol A epoxy acrylic ester, modified epoxy methacrylic ester and modified bisphenol A epoxy methacrylic ester.
4. The activity-controlled photocurable 3D printing resin as claimed in claim 2, characterized in that: the reactive diluent is selected from any one or a mixture of more of hydroxyethyl acrylate, hydroxypropyl acrylate, 4-hydroxybutyl acrylate, lauryl acrylate, isobornyl methacrylate, trimethylolpropane formal acrylate, 4-tert-butyl cyclohexyl acrylate, tetrahydrofuran methacrylate, acryloyl morpholine, tripropylene glycol diacrylate, 1, 6-hexanediol diacrylate, propoxylated neopentyl glycol diacrylate, tricyclodecane dimethanol diacrylate, polyethylene glycol (200) diacrylate, dipropylene glycol diacrylate, ethoxylated trimethylolpropane triacrylate, propoxylated glycerol triacrylate, ethoxylated pentaerythritol tetraacrylate and dipentaerythritol hexaacrylate.
5. The activity-controlled photocurable 3D printing resin as claimed in claim 2, characterized in that: the auxiliary agent is selected from any one or more of a leveling agent, a defoaming agent and a wetting dispersing agent.
6. The controlled activity photocurable 3D printing resin of claim 2, wherein: the pigment and the filler are selected from one or more of organic pigments or inorganic pigments.
7. A method of preparing a controlled activity photocurable 3D printing resin according to any of claims 1 to 6, characterized in that it comprises the following steps: according to the amount of the formula, the components are heated and stirred uniformly, the heating and stirring operation temperature is 30-90 ℃, and the heating and stirring operation time is not less than 0.5h, so that the Chinese herbal medicine is obtained.
8. Use of the controlled activity photocurable 3D printing resin according to any of claims 1 to 6, characterized in that: the resin material is used as a black-and-white screen LCD printer light-cured resin material, a color screen LCD printer light-cured resin material, a DLP printer light-cured resin material or an SLA printer light-cured resin material.
CN202110087359.7A 2021-01-22 2021-01-22 Controlled-activity photocuring 3D printing resin and preparation method and application thereof Pending CN112812241A (en)

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CN115286743A (en) * 2022-08-17 2022-11-04 中山大简科技有限公司 Photocuring resin for high-precision matte 3D printing and preparation method thereof

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CN108892837A (en) * 2018-05-26 2018-11-27 龙南天开科技有限公司 A kind of high-intensitive molding wax and preparation method thereof for MJP3D printing
CN108761863A (en) * 2018-05-30 2018-11-06 株洲晶彩电子科技有限公司 A kind of LCD techniques
CN109400177A (en) * 2018-10-30 2019-03-01 西安点云生物科技有限公司 For the ceramic material of 3D Stereolithography printing and the preparation method of ceramic objects
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113717323A (en) * 2021-08-10 2021-11-30 珠海市三绿实业有限公司 Low-irritation photosensitive resin
CN115286743A (en) * 2022-08-17 2022-11-04 中山大简科技有限公司 Photocuring resin for high-precision matte 3D printing and preparation method thereof

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