CN109180841A - A kind of application of photoinitiator in the colourless photocuring 3D printing of long wavelength - Google Patents
A kind of application of photoinitiator in the colourless photocuring 3D printing of long wavelength Download PDFInfo
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- CN109180841A CN109180841A CN201811034114.2A CN201811034114A CN109180841A CN 109180841 A CN109180841 A CN 109180841A CN 201811034114 A CN201811034114 A CN 201811034114A CN 109180841 A CN109180841 A CN 109180841A
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- printing
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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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/46—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides selected from alkali metals
- C08F4/48—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides selected from alkali metals selected from lithium, rubidium, caesium or francium
Abstract
The present invention provides a kind of application of photoinitiator in the colourless photocuring 3D printing of long wavelength, the structure of the photoinitiator is as follows:Photoinitiator maximum absorption wavelength used is up to 480nm in the present invention, it is thus possible to cause cured 3D printing technique for long wavelength light；Meanwhile initiator itself decomposes after light-induced polymerization, is converted to colourless or close to colourless, has the function of photobleaching, so as to solve the problems, such as the effective color section of the coloured bring of long wavelength light initiator.
Description
Technical field
The present invention relates to photocuring 3D printing fields, solid in long wavelength's non-colored light in particular to a kind of photoinitiator
Change the application in 3D printing.
Background technique
3D printing technique is a kind of rapid shaping technique, appears in mid-term the 1990s earliest, obtains in recent years
It grows rapidly, and shows up prominently in multiple industries, show its application advantage.There are many molding modes of 3D printing, wherein light
Solidifying 3D printing technique is wherein to develop one of faster technology.The characteristics of due to photocuring, so that photocuring 3D printing technique
Have many advantages, such as that precision is high, shaping speed is fast, in personalized customization, such as the manufacture of medical domain, jewelry, model display field tool
There is important application.
Photocuring 3D printing technique is the technology by photocuring principle in conjunction with increases material manufacturing technology, is chemical science and machine
The embodiment of tool perfect combination, wherein the photocuring philosophy and technique embodied is consistent with traditional photocuring technology.Photocuring technology is
The novel green technology that the 1960s comes out, refers under the action of light (ultraviolet light or visible light), liquid-state oligomers warp
It crosses cross-linked polymeric and forms the process of solid product.Photocuring system generally comprises following three kinds of main components: 1. oligomer, assigns
Material is given with basic physical and chemical performance.2. monomer, also known as reactive diluent are mainly used for the viscosity of regulation system, but
Also have an impact to solidification rate and material property.3. photoinitiator, for generating the free radical or ion that can cause polymerization.
Wherein, photoinitiator (photoinitiator) is the key components of photocuring system, is to be related to formula
System low energy in illumination is no to be changed into solid determinant by liquid rapidly.Photoinitiator is according to its splitting mechanism and causes
The difference of mechanism can be divided into radical photoinitiator and cationic photoinitiator two major classes.And what photoinitiator decomposed
Key driving force is the matched light source of absorbing wavelength, also known as effective wavelength therewith.If the launch wavelength of light source is not light-initiated
Within the scope of the absorbing wavelength of agent, photoinitiator to the light stability, will not by photodegradation, also this means that its cannot cause it is poly-
It closes.
Currently, the light source for photocuring 3D printing technique is essentially LED light source, limited by LED encapsulation material, it is low
It there is no matured product at present in the LED light source of 365nm wavelength.And it is more stable higher than the light source of 400nm, market is widely used.
This requires develop photoinitiator Wavelength matched therewith.Belong to visible light due to being greater than 400nm wavelength, it is meant that therewith
The photoinitiator matched has visible absorption wavelength, that is to say, that applied initiator itself is coloured, and wavelength is got over
Long, color is deeper.Photoinitiator 784 is used as usual, and absorbing wavelength can arrive 460nm 400, and shiny red is presented in itself.This just makes
The product for obtaining long wavelength's 3D printing has certain color, this needs colourless or some products for having particular color requirement to some
It can not print.
In view of this, the present invention is specifically proposed.
Summary of the invention
The first object of the present invention is to provide a kind of application of photoinitiator in the colourless photocuring 3D printing of long wavelength,
Photoinitiator used has and causes under long wavelength in the present invention, and crack and initiation reaction after self color take off, become nothing
Color connects subdiaphanous characteristic, has the function of photobleaching, to solve the problems, such as 3D printing workpiece with color.
In order to realize above-mentioned purpose of the invention, the following technical scheme is adopted:
A kind of application of photoinitiator in the colourless photocuring 3D printing of long wavelength, the structure of the photoinitiator are as follows:
Wherein, in formula (I), R1-R6It is independently hydrogen, halogen, functional group, with or without functional group
Alkyl, alkenyl or the alkynyl of linear chain or branched chain, the aryl of with or without functional group；
R7、R8It is independently hydrogen, the alkyl of the linear chain or branched chain of with or without functional group, alkenyl or alkynes
Base, the aryl of with or without functional group；Alternatively, R7、R8Saturated or unsaturated ring, institute are formed with adjacent carbon atom
It is optional substituted or non-substituted to state arbitrary hydrogen atom on ring；
Y1、Y2It is independently O, S, N-R9Or R10-C-R11；
R9-R11It is independently hydrogen, halogen, functional group, the linear chain or branched chain of with or without functional group
Alkyl, alkenyl or alkynyl, the aryl of with or without functional group；
Wherein, the functional group being had in R base as above are as follows: the functional group with nitrogen, oxygen or sulphur.
Preferably, light-initiated in application of the photoinitiator of the present invention in the colourless photocuring 3D printing of long wavelength
The structure of agent is as follows:
Or
Wherein, in formula (III), n be 1~8 integer；
R11、R12It is independently hydrogen, halogen, functional group, the linear chain or branched chain of with or without functional group
Alkyl, alkenyl or alkynyl, the aryl of with or without functional group；Wherein, the functional group is with nitrogen, oxygen or sulphur
Functional group.
Preferably, light-initiated in application of the photoinitiator of the present invention in the colourless photocuring 3D printing of long wavelength
The structure of agent is as follows:
Preferably, in application of the photoinitiator of the present invention in the colourless photocuring 3D printing of long wavelength, the official
Energy group are as follows: at least one in aldehyde radical, hydroxyl, carboxyl, carbonyl, amino, nitro, cyano, sulfydryl, sulfonic group or sulfanyl
Kind.
Preferably, in application of the photoinitiator of the present invention in the colourless photocuring 3D printing of long wavelength, 3D printing
Optical source wavelength be 330~480nm；It is furthermore preferred that the optical source wavelength of 3D printing is 390~450nm.
Preferably, in application of the photoinitiator of the present invention in the colourless photocuring 3D printing of long wavelength, 3D printing
Monomer include: esters of acrylic acid, methyl acrylic ester or vinyl ethers monomer；It is furthermore preferred that the monomer of 3D printing
It include: polyethylene glycols (methyl) acrylate.
Preferably, light-initiated in application of the photoinitiator of the present invention in the colourless photocuring 3D printing of long wavelength
The dosage of agent is the 0.005~5% of monomer mass；It is furthermore preferred that the dosage of photoinitiator be monomer mass 0.00625~
2%.
Preferably, in application of the photoinitiator of the present invention in the colourless photocuring 3D printing of long wavelength, institute is printed
Workpiece is obtained after secondary light photograph, the color fading of workpiece is colourless.
Preferably, in application of the photoinitiator of the present invention in the colourless photocuring 3D printing of long wavelength, secondary light
According to wavelength be 330~480nm；It is furthermore preferred that the wavelength that secondary light is shone is 390~450nm.
Preferably, in application of the photoinitiator of the present invention in the colourless photocuring 3D printing of long wavelength, secondary light
According to time be less than 5h；It is furthermore preferred that the time that secondary light is shone is 5~30min.
Compared with prior art, the invention has the benefit that
Photoinitiator maximum absorption wavelength used is up to 480nm in the present invention, it is thus possible to cause for long wavelength light solid
The 3D printing technique of change；Meanwhile initiator itself decomposes after light-induced polymerization, is converted to colourless or close to colourless, has
Photobleaching function, so as to solve the problems, such as the effective color section of the coloured bring of long wavelength light initiator.
Detailed description of the invention
In order to more clearly explain the embodiment of the invention or the technical proposal in the existing technology, to embodiment or will show below
There is attached drawing needed in technical description to be briefly described.
Fig. 1 is that the embodiment of the present invention 1 prints obtained analog cochlea；
Fig. 2 is the cochlea analog cochlea that color is become colorless by yellow after secondary light is shone that the embodiment of the present invention 1 obtains.
Specific embodiment
Embodiment of the present invention is described in detail below in conjunction with embodiment, but those skilled in the art will
Understand, the following example is merely to illustrate the present invention, and is not construed as limiting the scope of the invention.It is not specified in embodiment specific
Condition person carries out according to conventional conditions or manufacturer's recommended conditions.Reagents or instruments used without specified manufacturer is
The conventional products that can be obtained by commercially available purchase.
In view of in the presence of existing 3D printing face is had with printing workpiece caused by color initiator
The technical issues of color, the present invention provides it is a kind of it is new, can draw in the light of the application in the colourless photocuring 3D printing of long wavelength
Agent is sent out, since photoinitiator of the present invention itself can decompose after light-induced polymerization, so that gained workpiece is being beaten
Can be become colorless by lighting process after print, so solve existing photoinitiator in use the problems of.
Specifically, the structure of photoinitiator provided by the present invention is as follows:
Wherein, in formula (I), R1-R6Independently can be with are as follows: hydrogen；Halogen (F, Cl, Br, I)；Functional group (aldehyde radical, hydroxyl
One of base, carboxyl, amino, nitro, cyano, sulfydryl or sulfonic group)；The straight chain of with or without functional group or
The C1-C30 alkyl (preferably C1-C12 alkyl, more preferably C1-C6 alkyl) of branch, C2-C30 alkenyl (preferably C2-C12
Alkenyl, more preferably C1-C6 alkenyl) or C2-C30 alkynyl (preferably C2-C12 alkynyl, more preferably C1-C6 alkynyl), as above
The functional group that may be had in alkyl is aldehyde radical, hydroxyl, carboxyl, carbonyl, amino, nitro, cyano, sulfydryl, sulfonic group or sulphur
At least one of alkyl；The C5-C30 aryl (the preferably aryl of C5-C12) of with or without functional group, it is as above fragrant
The functional group that may be had in base is aldehyde radical, hydroxyl, carboxyl, carbonyl, amino, nitro, cyano, sulfydryl, sulfonic group or sulfane
At least one of base.
R7、R8It is independently hydrogen, the C1-C30 alkyl of the linear chain or branched chain of with or without functional group is (preferably
For C1-C12 alkyl, more preferably C1-C6 alkyl), C2-C30 alkenyl (preferably C2-C12 alkenyl, more preferably C1-C6 alkene
Base) or C2-C30 alkynyl (preferably C2-C12 alkynyl, more preferably C1-C6 alkynyl), the function that may be had in alkyl as above
Group is at least one of aldehyde radical, hydroxyl, carboxyl, carbonyl, amino, nitro, cyano, sulfydryl, sulfonic group or sulfanyl；Band
Have or without functional group C5-C30 aryl (the preferably aryl of C5-C12), the functional group that may be had in aryl as above
For at least one of aldehyde radical, hydroxyl, carboxyl, carbonyl, amino, nitro, cyano, sulfydryl, sulfonic group or sulfanyl；
Alternatively, R7、R8Saturated or unsaturated five yuan, hexa-atomic, seven yuan, eight yuan, nine yuan, ten are formed with adjacent carbon atom
The cyclic structure of the annular atoms such as member (carbon) number, and upper arbitrary hydrogen atom is optional in cyclic structure is substituted or non-takes
Generation can be C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, C5-C30 aryl, halogen as the substituent group being optionally present
(F, Cl, Br, I) perhaps functional group (one in aldehyde radical, hydroxyl, carboxyl, amino, nitro, cyano, sulfydryl or sulfonic group
At least one of kind).
Y1、Y2It is independently O, S, N-R9Or R10-C-R11；
R9-R11It is independently hydrogen；Halogen (F, Cl, Br, I)；Functional group (aldehyde radical, hydroxyl, carboxyl, amino, nitre
One of base, cyano, sulfydryl or sulfonic group)；The C1-C30 alkyl of the linear chain or branched chain of with or without functional group
(preferably C1-C12 alkyl, more preferably C1-C6 alkyl), C2-C30 alkenyl (preferably C2-C12 alkenyl, more preferably C1-
C6 alkenyl) or C2-C30 alkynyl (preferably C2-C12 alkynyl, more preferably C1-C6 alkynyl), it may have in alkyl as above
Functional group is at least one in aldehyde radical, hydroxyl, carboxyl, carbonyl, amino, nitro, cyano, sulfydryl, sulfonic group or sulfanyl
Kind；The C5-C30 aryl (the preferably aryl of C5-C12) of with or without functional group may have in aryl as above
Functional group is at least one in aldehyde radical, hydroxyl, carboxyl, carbonyl, amino, nitro, cyano, sulfydryl, sulfonic group or sulfanyl
Kind.
It is further preferred that as above formula (I) structural compounds can be with are as follows:
Or
Wherein, formula (II), R1-R6、Y1、Y2(and Y1、Y2The middle R that may include9-R11) definition with as in above formula (I)
Definition it is identical；
Preferably, in formula (II), R1=R6, R2=R5, R3=R6, Y1=Y2；I.e. formula (II) compound is preferably symmetrical structure
Compound；
Specifically, formula (II) compound can be with are as follows:
Meanwhile in formula (III), R1-R6、Y1、Y2(and Y1、Y2The middle R that may include9-R11) definition with such as above formula (I)
In definition it is identical；
In formula (III), n be 1~8 integer (i.e. 1,2,3,4,5,6,7 or 8)；
R11、R12It is independently hydrogen；Halogen (F, Cl, Br, I)；Functional group (aldehyde radical, hydroxyl, carboxyl, amino, nitre
One of base, cyano, sulfydryl or sulfonic group)；The C1-C30 alkyl of the linear chain or branched chain of with or without functional group
(preferably C1-C12 alkyl, more preferably C1-C6 alkyl), C2-C30 alkenyl (preferably C2-C12 alkenyl, more preferably C1-
C6 alkenyl) or C2-C30 alkynyl (preferably C2-C12 alkynyl, more preferably C1-C6 alkynyl), it may have in alkyl as above
Functional group is at least one in aldehyde radical, hydroxyl, carboxyl, carbonyl, amino, nitro, cyano, sulfydryl, sulfonic group or sulfanyl
Kind；The C5-C30 aryl (the preferably aryl of C5-C12) of with or without functional group may have in aryl as above
Functional group is at least one in aldehyde radical, hydroxyl, carboxyl, carbonyl, amino, nitro, cyano, sulfydryl, sulfonic group or sulfanyl
Kind；
Preferably, in formula (III), R1=R6, R2=R5, R3=R6, Y1=Y2；I.e. formula (III) compound is preferably symmetrical junction
Structure compound.
Further, as above formula (III) compound can be with are as follows:
In formula (IV), R1-R6、Y1、Y2(and Y1、Y2The middle R that may include9-R11) definition determine with such as above formula (I)
Justice is identical
Preferably, in formula (IV), R1=R6, R2=R5, R3=R6, Y1=Y2；I.e. formula (III) compound is preferably symmetrical junction
Structure compound；
Specifically, formula (IV) compound can be with are as follows:
Particularly, formula (I) compound can be with are as follows: two furfurylidene cyclohexanone, two furfurylidene-acetones, two sulfurous sulfuryl hexamethylenes
Ketone, two sulfurous sulfuryl acetone etc..
Meanwhile the present invention can also provide a kind of colourless photocuring 3D printing system of long wavelength, and in the 3D printing system, packet
Containing photoinitiator as described above and 3D printing monomer；
Wherein, the monomer of the 3D printing includes: esters of acrylic acid, methyl acrylic ester or vinyl ethers list
Body；Preferably, the monomer of 3D printing includes: polyethylene glycols (methyl) acrylate (for example, polyethylene glycol acrylate, poly-
Glycolmethacrylate etc.)；
Meanwhile the dosage of photoinitiator is the 0.005~5% of monomer gross mass, such as can be, but be not limited to 0.01,
0.05,0.1,0.5,1,2,3,4% etc.；Preferably the 0.00625~2% of monomer mass.
Further, the 3D printing process of the colourless photocuring 3D printing system of present invention long wavelength as above is as follows:
After each raw material is mixed, under the conditions of optical source wavelength is 330~480nm (preferably 390~450nm) LED light source,
3D printing is carried out, is obtained after solidification with coloured semi-finished product；
Semi-finished product is progress under the conditions of 330~480nm (preferably 390~450nm) LED light source with optical source wavelength
Secondary light less than 5h (preferably 5~30min) is shone, and after secondary light is shone, semi-finished product becomes colorless, and obtains finished product work
Part.
Embodiment 1
With 100 grams of polyethylene glycol acrylate, two 0.05 gram of furfurylidene cyclohexanone are raw material, in the LED light of 405nm wavelength
Solidify in 3D printer, print analog cochlea, gained analog cochlea is as shown in Figure 1, whole is in yellow；
Then, it is irradiated analog cochlea 20 minutes with the LED light source secondary light of 390nm wavelength, the cochlea mould after secondary light photograph
As shown in Fig. 2, after secondary light is shone, the color of analog cochlea is become colorless type by yellow.
Embodiment 2
With 50 grams of polyethylene glycol acrylate, 50 grams of hydroxy ethyl methacrylate, two 0.5 gram of furfurylidene cyclohexanone are raw material,
In the LED light solidification 3D printer of 420nm wavelength, analog cochlea is printed；
Then, it is shone analog cochlea 30 minutes with the LED light source secondary light of 405nm wavelength, the color of analog cochlea is by yellow
It becomes colorless；Experiment effect is same as Example 1.
Embodiment 3
With 50 grams of polyethylene glycol acrylate, 50 grams of epoxy acrylate, two 1 gram of furfurylidene-acetones are raw material, in 450nm
In the LED light solidification 3D printer of wavelength, analog cochlea is printed；
Then, it is shone analog cochlea 50 minutes with the LED light source secondary light of 405nm wavelength, the color of analog cochlea is by yellow
It becomes colorless；Experiment effect is same as Example 1.
Embodiment 4
With 30 grams of hydroxy-ethyl acrylate, 30 grams of polyethylene glycol acrylate, 40 grams of polyester acrylate, two sulfurous sulfuryl rings
2 grams of hexanone are raw material, in the LCD photocuring 3D printer of 420nm wavelength, print analog cochlea；
Then, to be shone analog cochlea 60 minutes with the LED light source secondary light of 420nm wavelength, the color of analog cochlea is by Huang
Color becomes colorless；Experiment effect is same as Example 1.
Although illustrate and describing the present invention with specific embodiment, it will be appreciated that without departing substantially from of the invention
Many other change and modification can be made in the case where spirit and scope.It is, therefore, intended that in the following claims
Including belonging to all such changes and modifications in the scope of the invention.
Claims (10)
1. a kind of application of photoinitiator in the colourless photocuring 3D printing of long wavelength, which is characterized in that the photoinitiator
Structure is as follows:
Wherein, in formula (I), R1-R6It is independently hydrogen, halogen, functional group, the straight chain of with or without functional group
Or alkyl, alkenyl or the alkynyl of branch, the aryl of with or without functional group；
R7、R8It is independently hydrogen, the alkyl of the linear chain or branched chain of with or without functional group, alkenyl or alkynyl, band
Have or without functional group aryl；
Alternatively, R7、R8Saturated or unsaturated ring is formed with adjacent carbon atom, arbitrary hydrogen atom can be optional on the ring
Be substituted or it is non-substituted；
Y1、Y2It is independently O, S, N-R9Or R10-C-R11；
R9-R11It is independently hydrogen, halogen, functional group, the alkyl of the linear chain or branched chain of with or without functional group,
Alkenyl or alkynyl, the aryl of with or without functional group；
Wherein, the functional group being had in R base as above are as follows: the functional group with nitrogen, oxygen or sulphur.
2. application of the photoinitiator according to claim 1 in the colourless photocuring 3D printing of long wavelength, which is characterized in that
The structure of the photoinitiator is as follows:
Wherein, in formula (III), n be 1~8 integer；
R11、R12It is independently hydrogen, halogen, functional group, the alkyl of the linear chain or branched chain of with or without functional group,
Alkenyl or alkynyl, the aryl of with or without functional group；
Wherein, the functional group is the functional group with nitrogen, oxygen or sulphur.
3. application of the photoinitiator according to claim 2 in the colourless photocuring 3D printing of long wavelength, which is characterized in that
The structure of the photoinitiator is as follows:
4. application of the photoinitiator according to any one of claim 1-3 in the colourless photocuring 3D printing of long wavelength,
It is characterized in that, the functional group are as follows: aldehyde radical, hydroxyl, carboxyl, carbonyl, amino, nitro, cyano, sulfydryl, sulfonic group, or
At least one of sulfanyl.
5. application of the photoinitiator according to any one of claim 1-3 in the colourless photocuring 3D printing of long wavelength,
It is characterized in that, the optical source wavelength of 3D printing is 330~480nm；
Preferably, the optical source wavelength of 3D printing is 390~450nm.
6. application of the photoinitiator according to any one of claim 1-3 in the colourless photocuring 3D printing of long wavelength,
It is characterized in that, the monomer of 3D printing includes: esters of acrylic acid, methyl acrylic ester or vinyl ethers monomer；
Preferably, the monomer of 3D printing includes: polyethylene glycols (methyl) acrylate.
7. application of the photoinitiator according to claim 6 in the colourless photocuring 3D printing of long wavelength, which is characterized in that
The dosage of photoinitiator is the 0.005~5% of monomer mass；
Preferably, the dosage of photoinitiator is the 0.00625~2% of monomer mass.
8. application of the photoinitiator according to any one of claim 1-3 in the colourless photocuring 3D printing of long wavelength,
It is characterized in that, printing gained workpiece, after secondary light photograph, the color fading of workpiece is colourless.
9. application of the photoinitiator according to claim 8 in the colourless photocuring 3D printing of long wavelength, which is characterized in that
The wavelength that secondary light is shone is 330~480nm；
Preferably, the wavelength that secondary light is shone is 390~450nm.
10. application of the photoinitiator according to claim 8 in the colourless photocuring 3D printing of long wavelength, feature exist
In the time that secondary light is shone is less than 5h；
Preferably, the time that secondary light is shone is 5~30min.
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Application publication date: 20190111 |
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