CN100569877C - Contain the dendritic structural compounds of branch and the application thereof of many UV crosslinking reactive group - Google Patents
Contain the dendritic structural compounds of branch and the application thereof of many UV crosslinking reactive group Download PDFInfo
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Abstract
The sphere that the present invention relates to a kind of many UV of containing crosslinking reactive group is divided dendritic structural compounds, and its core is the isocyanuric acid ester group, and its skeleton contains a plurality of polar functional groups and end is the UV crosslinking group.The present invention also provides the precursor of this compound, and multiple application of compound such as adhesion promotor, photosensitive resin composition, ink for ink-jet print, particularly ink for ink-jet print hardness and the water stability behind spray printing can significantly promote.
Description
Technical field
The sphere that the present invention relates to a kind of many UV of containing crosslinking reactive group is divided dendritic structural compounds, further is particularly related to the application of this compound in ink jet ink composition.
Background technology
Multiple ink-jet technology has been applied on the quick print, and more common SOME METHODS comprises continous inkjet method (continuous ink jet printing) and promptly need promptly print method (drop-on-demand).The former can utilize voltage to produce principle such as two-way deflection and the multidirectional deflection of deflection, the mode ink supply of ink-jet and not ink-jet when not charged when foundation is charged.The latter's principle is generally following dual mode: mobile piezoelectric transformer produces pressure wave to form ink droplet, is generally called piezoelectric method, and is another kind of with thermal pulse formation ink droplet, is commonly referred to as thermal bubble type.
But the composition rough segmentation of ink is water-soluble type, oily molten type, solvent-borne type, hot-melting type and light-cured type.Because the mechanism of preceding amphitypy quite relies on the osmotic absorption of ink with dry, back three is fit to apply to metal, pottery, plastic cement etc. not on the material of blotting.The present invention is particularly to the ink for ink-jet print of light-cured type, and its most important also the most basic patent is a United States Patent (USP) the 4th, 303, and the low-molecular-weight molecule that has disclosed the multiple carbon-carbon double bonds of utilization for No. 924 is the photocuring composition.The photocurable ink that other are disclosed for No. 207302 as the tw Taiwan patent, or No. the 207308th, tw Taiwan patent disclose, be that utilization contains monomer, oligomer or the resin of the carbon-carbon double bond photocurable composition as pigment, and this pigment applied to the making of LCD colored filter.United States Patent (USP) the 4th, 680 has disclosed a kind of photocuring ink composition and has comprised a polyamines ethyl formate for No. 368.European patent A0465039 and A0540203 also disclose and contain the multiple photocuring ink that contains polymerisable monomer.These patents all are difficult to the sticking power deficiency of avoiding the degree of crosslinking deficiency to be caused, chemical resistant properties, thermotolerance deficiency, problems such as embrittlement.The problem of stability when in addition, too high flowability will cause colo(u)rant dispersion.But if chain photocurable composition is elongated its stability of increase, ink is improved in the viscosity of ink-jet casket, be head it off, must import multiple photo curable monomer again and do fine setting.This all can cause trouble in the control of follow-up improvement and quality, and then raises the cost.
Therefore how further designing a photocurable molecule that addresses the above problem, and then be applied to ink for ink-jet print, is a problem needing solution badly.Dendrimer (dendrimer) is owing to have a large amount of modifiable side chains, extensively applied in recent years in the fields such as pharmacy, synthetic, supramolecular chemistry.Dendrimer comprises the polyester class aminate that US2005/0147834 A1 is disclosed in the application of photocurable ink, but as the most technician in this area, a chain end of this patent also is an aminate, and can't carry out photocuring reaction.US 6,221, and the arborescence that 933 B1 disclose has terminal amido, improves the wet fastness of ink spray printing in glass surface, and available bases is washed the ink of clean spray printing to reclaim glass.Even as US 6,300, though the arborescence that 388 B1 are disclosed has the carbon-carbon double bond that can carry out photocuring reaction, its chain end still is an aminate, but place intramolecule but not terminal two keys, will cause the steric barrier of photocuring reaction and reduce the speed and the degree of ink cured.The end suspention dyestuff chromophore of many people with dendrimer also arranged in addition, and one of them is US 2003/0096885 A1, though can improve ink-jet, strengthen character such as fast light, water-fast, resistant, still as US 6,300,388 B1 lack photo curable functional end-group.
The core kind of dendrimer is a basic but important selection.Generally be with planar molecule such as triazine (triazine) or benzene as central element, but because of the two aromaticity and planarity are difficult for causing from all directions crosslinked of 3 D stereo, and reduce rerum natura such as hardness, photostabilization.Therefore the improvement of many this respects appears, one of them is United States Patent (USP) notification number US 2004/0163570 A1, become the globe (non-dendrimer) of a multichain with the external a plurality of side chains of symmetric silica cage (cage), its terminal for carbon-carbon double bond to carry out photocuring.Though the big core of this patent can be avoided the problem of steric barrier, silica cage that it is excessive and uncommon chemical property will be more more difficult than the arborescence that with the organic molecule is core in further extension and improvement.
Summary of the invention
In view of this, the present invention provides a sphere that contains many UV crosslinking reactive group to divide dendritic structural compounds especially, comprises: a core, its structure are the isocyanuric acid ester group; And the dendritic substituting group of a plurality of branches, its skeleton contains a plurality of polar functional groups, and end is the UV crosslinking reactive group.
The sphere of many UV of containing crosslinking reactive group of the present invention is divided in the dendritic structural compounds, the dendritic substituting group of these a plurality of branches, and its skeleton also comprises a plurality of aromatic bases.
The sphere of many UV of containing crosslinking reactive group of the present invention is divided in the dendritic structural compounds, and this UV crosslinking reactive group comprises carbon-carbon double bond.
The sphere of many UV of containing crosslinking reactive group of the present invention is divided dendritic structural compounds, and its structure can be as follows:
In the formula (I), R
1Be the segment after the epoxy alkane open loop; Ar is the aromatic base with a plurality of polar functional groups; And R
2Be the UV crosslinking reactive group, n is 1～5 integer.
In the above-mentioned formula (I), these polar functional groups that this Ar has can be ester group and hydroxyl.
The compound of above-mentioned formula (I), its concrete structure can be:
The present invention also provides a kind of spherical dendritic structural compounds that divides, and it divides the precursor of dendritic structural compounds for the sphere of above-mentioned many UV of containing crosslinking reactive group, and its structure is as follows:
In the formula (III), R
1Be the segment after the epoxy alkane open loop, Ar is the aromatic base with a plurality of polar functional groups.
In the above-mentioned formula (III), this Ar also can comprise following at least a substituting group: carboxylic acid group, hydroxyl or amido.
The compound of above-mentioned formula (III), its concrete structure can be:
The present invention also comprises a kind of photosensitive resin composition, comprising: a) 0.02～25wt% photo-sensitive initiators; B) sphere of above-mentioned many UV of the tool crosslinking reactive group of 1～99.8wt% is divided dendritic structural compounds; C) other photoresponse things of 0～98.98wt%.
The present invention also comprises a kind of ink jet ink composition, comprises a) solvent of 0.5～50wt%; B) colorant of 0.5～20wt%; C) photo-curing monomer of 1～90wt%; D) sphere of above-mentioned many UV of the tool crosslinking reactive group of 1～40wt% is divided dendritic structural compounds.
Ink jet ink composition of the present invention also can comprise e) light trigger of 0.1～25wt%.
In the ink jet ink composition of the present invention, this solvent comprises water, solvent or monomer.
Ink jet ink composition of the present invention, its viscosity are between 1～35cps, and surface tension is between 20～50 milli Newton/meter, and hardness is between 4H～4B.
The sphere of many UV of containing crosslinking reactive group of the present invention is divided dendritic structural compounds, can be used for adhesion promotor, photosensitive resin composition, ink for ink-jet print, the sphere that particularly comprises many UV of containing crosslinking reactive group of the present invention is divided the ink for ink-jet print of dendritic structural compounds, its hardness and water stability behind spray printing can significantly promote, and has good erasibility and sticking power.
Description of drawings
Figure 1A implements red black 3 actual ink-jet diagram.
Figure 1B is an actual ink-jet diagram of implementing green ink 3.
Fig. 1 C is an actual ink-jet diagram of implementing blue China ink 3.
Fig. 2 A is redder black 3 actual ink-jet diagram.
Fig. 2 B is the actual ink-jet diagram of comparison green ink 3.
Fig. 2 C is the actual ink-jet diagram of the blue China ink 3 of comparison.
Embodiment
The present invention provides a sphere that contains many UV crosslinking reactive group to divide dendritic structural compounds especially, comprises a core, and its structure is the isocyanuric acid ester group; The dendritic substituting group of a plurality of branches, its skeleton contain a plurality of aromatic bases, a plurality of polar functional group, and end is the UV crosslinking reactive group.Contain the polar functional group that the sphere of many UV crosslinking reactive group divides dendritic structural compounds to have and comprise amide group, amido, ester group, hydroxyl or ketone group, preferred embodiment of the present invention is ester group, hydroxyl and amido, and these polar functional groups can increase tack, hardness and the erasibility after the ink ink-jet moulding.Aromatic base comprises phenyl, pyridyl, naphthyl, anthryl, is preferably phenyl.Terminal UV crosslinking reactive group, the UV crosslinking reactive group that seemingly is not inserted in the skeleton has different chemical environments and steric barrier, therefore can make this molecule also carry out photocuring reaction fast uniformly.Above-mentioned UV crosslinking reactive group can comprise carbon carbon triple bond, carbon-carbon double bond, reach other suitable functional groups, and the preferred embodiment of this experiment is a carbon-carbon double bond.The preferable sphere that contains many UV crosslinking reactive group divide dendritic structural compounds have 18 ester groups, 3 amidos, with 15 hydroxyls, and end has 12 carbon-carbon double bonds.Ester group, amido, be not limited to a definite sequence or rule with the arrangement mode of hydroxyl, those skilled in the art are from kind and the number that can need adjust polar functional group with it, as long as end has the UV crosslinking reactive group carrying out photocuring reaction, such as the compound of array structure down:
Formula (I)
R
1Be the segment after the epoxy alkane open loop; Ar is the aromatic base with a plurality of polar functional groups; R
2Be the UV crosslinking reactive group, n is 1～5 integer.
Preferred embodiment comprises that a structure is as follows:
The invention provides the arborescence that a kind of core is the isocyanuric acid ester group, can divide the precursor of dendritic structural compounds as the sphere of many UV of tool crosslinking reactive group, its structure is as follows:
Formula (III)
Core texture is the isocyanuric acid ester group; R
1Be the segment after the epoxy alkane open loop; Ar is the aromatic base with a plurality of polar functional groups, and these polar functional groups comprise carboxylic acid group, hydroxyl or amido, and aromatic base comprises phenyl, pyridyl, naphthyl, anthryl, is preferably phenyl.This precursor is not a unique channel of finishing the object of the invention, and intermolecular arrangement still has other may.After it should be noted that above-mentioned precursor also can carry out other dendriticization (dendrimerize) reaction, carry out subsequent step again and make its end have the UV crosslinking reactive group, preferable precursor has following structural formula:
The selectable synthesis mode of arborescence mainly divides two kinds: the reducing-pitch thread (convergent) of divergence expression from inside to outside (divergent) and ecto-entad.If " generation " between core and functional end-group is (generation) more, then adopt reducing-pitch thread preferable; If in generation, is less, then based on more simple divergence expression; After also can divergence expression setting up the core in less generation, form target molecule with reducing-pitch thread synthetic functional end-group bond.Therefore the present invention is main synthesis strategy with divergence expression because generation is less, but also can reducing-pitch thread or mode that both all have synthetic.For instance, the initiator that contains core and be the isocyanuric acid ester group comprises symclosene (trichloroisocyanuric acid), three (2, the 3-epoxypropyl)-isocyanuric acid ester (tris (2,3-epoxypropyl) isocyanurate), iso-cyanuric acid triallyl ester (triallyl-1,3,5-triazine-2,4,6 (1H, 3H, 5H)-trione), preferable initiator is three (2, the 3-epoxypropyl)-isocyanuric acid esters.Three (2, the 3-epoxypropyl)-isocyanuric acid esters are carried out ring-opening reaction with a nucleophilicity (Nucleophile) reagent down in solvent, and this nucleophilicity reagent comprises following compounds:
Formula V
C wherein
nBe a C
1-C
10Alkyl, Nu is reactive nucleophilicity functional group than the reactive difference of secondary amine, comprises hydroxyl, with the primary amine (if not protecting its reactivity will be higher than secondary amine) of protecting group protection, preferable Nu is a hydroxyl.This nucleophilicity reagent also comprises other possibilities, such as 1,3, and 5-three amido benzene, 1,3,5-trihydroxybenzene or other have the compound of symmetry three nucleophilicity functional groups.
After carrying out above-mentioned reaction, obtain an end and be the arborescence intermediate of nucleophillic attack base.The aromatic base that this intermediate and is had a plurality of polar functional groups reacts, if the functional end-group of intermediate is a hydroxyl, when the polar functional group of aromatic base is carboxylic acid or acid anhydrides, then carries out an esterification.If the functional end-group of intermediate is primary amine (carrying out protective reaction earlier), when the polar functional group of aromatic base is carboxylic acid or acid anhydrides, then carry out the monoamide reaction.Aromatic base with a plurality of polar functional groups comprises 1,2,3-benzene tricarboxylic acid acid anhydride, 1,2,4-benzene tricarboxylic acid acid anhydride, 1,3,5-tricarboxylic acid benzene.Aromatic base with polar functional group also comprises array structure down:
Formula (VI)
C
mBe one to have the C of polar functional group such as ester group or amide group
1-C
10Alkyl.N is the integer of 1-6, and X is a halogen, and good and above-mentioned nucleophilicity functional group carries out substitution reaction.
At last, the compound that other unreacted polar functional groups such as carboxylic acid group and an end have a UV crosslinking reactive group on the aromatic base reacts, and the sphere that then obtains many UV of tool crosslinking reactive group is divided dendritic structural compounds.These polar functional groups are not to react with UV cross-linking reaction base, but react with other functional groups of this compound, such as epoxy group(ing) (carrying out ring-opening reaction), halogen (carrying out substitution reaction).If its structure of aromatic base with polar functional group is following formula (VI), then terminal compound with UV crosslinking reactive group must have nucleophilicity functional group such as hydroxyl or amido carrying out substitution reaction, but not epoxy group(ing) or halogen.
In brief, so long as can be core with the isocyanuric acid ester group, but the UV crosslinking functionality is terminal, and with various polarity functional group is the arborescence of skeleton, under rational reaction conditions, all in design of the present invention, and be not subject to above-mentioned synthesis strategy and the following example.
The present invention also comprises and divides dendritic structural compounds to be applied to adhesion promotor the sphere of many UV crosslinking reactive group, can be used for the tackiness agent of materials such as paper, metal, pottery, timber, glass, plastic cement when bonding.
The invention provides a kind of photosensitive resin composition, comprised that the sphere of above-mentioned many UV of tool crosslinking reactive group of the photo-sensitive initiators of 0.02～25wt% and 1～99.8wt% is divided dendritic structural compounds and other photoresponse things of 0～98.98wt%.Common photo-sensitive initiators comprises following molecule: the perfume base alkyl oxide of resting in peace (benzoin alkyl ether), 2,2-dimethoxy-2-phenyl acetophenone (2,2-dimethoxy-2-phenylacetophenone), benzophenone (benzophenone), pentabromo-one chlorine hexanaphthene (pentabromomonochlorocyclohexane), pentachlorobenzene (pentachlorobenzene), polychlorobiphenyl (polychlorinated biphenyl), 2-ethyl-anthraquinone (2-ethylanthraquinone), 1-chloroethyl naphthalene (1-chloroethylnaphthalene), 2-bromotrifluoromethane ether (2-bromoethyl ether), or other suitable light triggers.Other photoresponse things such as Viscoat 335HP (tetraethylene glycoldiacrylate, TGD), isobornyl acrylate (isobornyl acrylate, IBOA), inhibitor as: 1,6-hexylene glycol dipropyl dilute acid ester (1,6-hexanediol diacrylate, HPDA).The application of this photosensitive resin comprises the negative photoresistance of making photovoltaic.
The invention provides a kind of ink jet ink composition, comprise the solvent of 0.5～50wt%, can be; 0.5 the colorant of～20wt%; The photo-curing monomer of 1～90wt%; The sphere of many UV of tool crosslinking reactive group that 1～40wt% is above-mentioned is divided dendritic structural compounds.Above-mentioned composition was stirred 10～20 minutes, get final product an ink for ink-jet print.Solvent is the organic solvent of solvable other compositions, above-mentioned colorant has comprised dyestuff or pigment, Pigment Red 149, the Pigment Green 36 or the Pigment Blue 15:3 that are sold of Ciba company for example, the median size of pigment is preferably 90～200nm between 70～220nm.Photo-curing monomer for example is Viscoat 335HP (tetraethylene glycol diacrylate, TGD), and isobornyl acrylate (isobornyl acrylate, IBOA), inhibitor as: 1, the 6-hexanediyl ester (1,6-hexanediol diacrylate, HPDA), 2, the 6-di-tert-butyl-4-methy phenol (2,6-di-tert-butyl-4-methyphenol, BHT).In the preferred embodiment, also comprise the light trigger of 0.1～15wt%.Common photo-sensitive initiators comprises following molecule: 2-hydroxyl-1-phenyl-1-acetone (2-hydroxy-1-phenyl-propyl-1-one), the perfume base alkyl oxide (benzoin alkyl ether) of resting in peace, 2,2-dimethoxy-2-phenyl acetophenone (2,2-dimethoxy-2-phenylacetophenone), benzophenone (benzophenone), pentabromo-one chlorine hexanaphthene (pentabromomonochlorocyclohexane), pentachlorobenzene (pentacjlorobenzene), polychlorobiphenyl (polychlorinated biphenyl), 2-ethyl-anthraquinone (2-ethylanthraquinone), 1-chloroethyl naphthalene (1-chloroethylnaphthalene), 2-bromotrifluoromethane ether (2-bromoethyl ether), or other suitable light triggers.
Above-mentioned ink jet ink composition viscosity is between 1～35cps, and surface tension is between 20～50 milli Newton/meter, to such an extent as to the ink of this range of viscosities can too sticking plug nozzle before ejection, also can too rarely not cause can't moulding after the ejection.The hardness of ink after the ejection moulding is between 4H～4B, and has (the hundred lattice test of good water stability, erasibility and sticking power, Cross-Cut Tester), but spray printing on the base material of no blotting such as metal, pottery, glass, plastic cement, it has good hardness and scratch resistance.Moreover, the irradiation UV light time behind the spray printing, but because irradiation solidified UV crosslinking reactive group can increase the polyreaction with other monomers or oligomer, keeping quality and the rerum natura that can further promote the thing of prining.
Preparation example one:
Fs:
With 2.55g (10mmol) three (2,3 epoxypropyl)-isocyanuric acid ester (TGIC, tris (2,3-epoxypropyl) isocyanurate) with 3.75g (36mmol, 1.2 equivalent) diethanolamine (diethanolamine) produces very exothermic after stirring three hours under the room temperature, and temperature is controlled in below 120 ℃, treats after heat release finishes temperature of reaction to be controlled in 100 ℃ and sustained reaction 10 hours, with FT-IR (Fourier transform infrared spectroscopy) following response, treat 3050～3000cm
-1(signal of N-H) and 950～810cm
-1The blackout of (signal of epoxy group(ing)) promptly represent the reaction finish its reaction formula such as figure below:
Subordinate phase:
With 17.28g (90mmol, 1.5 equivalent) 1,2,4-benzene tricarboxylic acid acid anhydride (trimelliticanhydride, TMA) (NMP, N-methyl-α-pyrrolidone) add above-mentioned reaction and in 90 ℃ of reactions 4 hours with N-methyl-alpha-pyrrolidone of 100mL, with the FT-IR following response, treat 1780cm
-1(signal of acid anhydrides) disappears promptly to represent to react and finishes its reaction formula such as figure below:
Phase III:
17.04g (120mmol, 2 equivalents) methyl-prop diluted acid Racemic glycidol fat (GMA, glycidyl methacrylate) is added above-mentioned reaction and promptly gets product in 90 ℃ of reactions after 6 hours, and its structure is as follows:
It is as follows to the invention provides preferable ink for ink-jet print embodiment and comparing embodiment in addition:
Embodiment 1
Form the basic recipe of light-cured type ink according to different ratios with light trigger (2-hydroxyl-1-phenyl-1-acetone), photocurable monomer (BHT, TGD) and dendritic compound of the present invention (preparation example one), with the light trigger is weight basis (1 part), BHT is fixed as 0.04 part, and the ratio of adjustment TGD and arborescence of the present invention is implemented prescription 1～3 to form.
Table 1
| Formula number | Light trigger | BHT | TGD | The compounds of this invention |
| Implement prescription 1 | 1 part | 0.04 part | 109.5 part | 52 parts |
| Implement prescription 2 | 1 part | 0.04 part | 142.8 part | 26 parts |
| Implement prescription 3 | 1 part | 0.04 part | 165 parts | 9 parts |
To implement prescription 1～3, cosolvent, tensio-active agent according to following table afterwards mixes and stirred ten minutes.Cosolvent is that (2-pyrrolidone, 2PO), tensio-active agent is preferably the BYK 333 that BYK company sells to 2-Pyrrolidone.Said mixture is added entry, and change stirring with the high-speed stirring clarifixator with per minute 5000 and wait for lather collapse quietly after 5 minutes.With scraper three kinds of prescriptions are coated the film of formation 25 micron thickness on glass and with 110 ℃ of bakings 60 minutes, carried out ultra violet lamp with cured film with 170 ℃ of bakings after 45 minutes again, carry out hardness test such as table 2.
Table 2
| Lot number | H 2O | 2PO | Basic recipe (12.5 parts) | Water stability | Hardness | Hundred lattice % |
| Implement film 1 | 20 parts | 50 parts | Implement prescription 1 | Stable | 5H | 100 |
| Implement film 2 | 20 parts | 50 parts | Implement prescription 2 | Stable | 4H | 100 |
| Implement film 3 | 20 parts | 50 parts | Implement prescription 3 | Stable | 3H | 100 |
Can find by table 2, when arborescence ratio of the present invention improves, can improve the film hardness behind the photocuring really.
Comparing embodiment 1
With the prescription of propylene oxide oligomer (epoxy acrylic oligomer, Sartomer N120) as the light-cured type ink.Its ratio is as follows, and except The compounds of this invention is replaced as the N120, other components in proportions are all identical.
Table 3
| Formula number | Light trigger | BHT | TGD | N120 |
| Relatively fill a prescription 1 | 1 part | 0.04 part | 109.5 part | 52 parts |
| Relatively fill a prescription 2 | 1 part | 0.04 part | 142.8 part | 26 parts |
| Relatively fill a prescription 3 | 1 part | 0.04 part | 165 parts | 9 parts |
The bonding practice as embodiment 1, will relatively fill a prescription with the same step 1～3 forms relatively film 1～3 and carries out hardness test such as table 4.
Table 4
| Lot number | H 2O | 2PO | Relatively fill a prescription (12.5 parts) | Water stability | Hardness | Hundred lattice % |
| Compare film 1 | 20 parts | 50 parts | Relatively fill a prescription 1 | Stable | 2H | 100 |
| Compare film 2 | 20 parts | 50 parts | Relatively fill a prescription 2 | Stable | 2H | 100 |
| Compare film 3 | 20 parts | 50 parts | Relatively fill a prescription 3 | Stable | F | 100 |
Though can find that by table 4 N120 equally has the effect of photocuring, under the same ratio, spherical arborescence of the present invention is good than the effect of chain oligomer N120 in the effect of photocuring.
Embodiment 2
Mix stirring to survey its character with implementing prescription 1～3 with the pigment concentrated solution of L1R1, L1G03, L1B14.Grind respectively with red pigment such as Pigment Red (Pigment red) 21, Pigment Green (Pigment green) 03, with Pigment Blue (Pigment blue) 15:3 and can make pigment L1R21, L1G03, L1B14 by oneself, its rerum natura such as following table:
Table 5
| Pigment color | L1R21 (redness) | L1G03 (green) | L1B14 (blueness) |
| Pigment | PR149 | PG36 | PB15:3 |
| Pigment ratio (%) | 15.1 | 14.9 | 14.9 |
| The pH value | 7.9 | 5.5 | 7.7 |
| Viscosity (cps) | 7.5 | 90 | 62 |
| Surface tension (milli Newton/meter) | 47 | 48.9 | 49.8 |
| Median size (nm) | 198.8 | 91 | 155.8 |
After will implementing water (7.57%), 2PO (20.83%), surfactant B YK333 (all accounting for 0.8%) that prescription 1～3 (embodiment 1) and 1～3 (comparing embodiment 1) of relatively filling a prescription add the same ratio separately, making pigment (all accounting for 58.3%) by oneself, stir 15 minutes to form ink jet ink composition, with scraper with its coat formation 25 micron thickness on glass ink film and with 110 ℃ the baking 60 minutes, carry out ultra violet lamp with the solidified ink film with 170 ℃ of bakings after 45 minutes again, carry out hardness test such as table 6.
Table 6
| The ink numbering | Prescription | Pigment | Water stability | Viscosity (cps) | Surface tension (milli Newton/meter) | Hardness | Hundred lattice (%) |
| Implement red black 1 | Implement prescription 1 | L1R21 | Stable | 11.8 | 34.5 | 4H | 100 |
| Implement red black 2 | Implement prescription 2 | L1R21 | Stable | 10.1 | 34.5 | 3H | 100 |
| Implement red black 3 | Implement prescription 3 | L1R21 | Stable | 7.98 | 34 | H | 100 |
| Implement green ink 1 | Implement prescription 1 | L1G03 | Stable | 8.47 | 33.5 | 4B | 100 |
| Implement green ink 2 | Implement prescription 2 | L1G03 | Stable | 7.94 | 33 | 4B | 100 |
| Implement green ink 3 | Implement prescription 3 | L1G03 | Stable | 7.87 | 33 | 4B | 100 |
| Implement blue China ink 1 | Implement prescription 1 | L1B14 | Stable | 18.6 | 34.5 | ＜4B | 100 |
| Implement blue China ink 2 | Implement prescription 2 | L1B14 | Stable | 17.9 | 34 | F | 100 |
| Implement blue China ink 3 | Implement prescription 3 | L1B14 | Stable | 16.7 | 34.5 | HB | 100 |
| Redder black 1 | Relatively fill a prescription 1 | L1R21 | Jelly | Jelly | Jelly | - | - |
| Redder black 2 | Relatively fill a prescription 2 | L1R21 | Retrogradation | 11.8 | 34.5 | HB | 100 |
| Redder black 3 | Relatively fill a prescription 3 | L1R21 | Stable | 9.53 | 34 | HB | 100 |
| Compare green ink 1 | Relatively fill a prescription 1 | L1G03 | Stable | 8.84 | 32.5 | ＜4B | 100 |
| Compare green ink 2 | Relatively fill a prescription 2 | L1G03 | Stable | 7.92 | 32.5 | ＜4B | 100 |
| Compare green ink 3 | Relatively fill a prescription 3 | L1G03 | Stable | 7.62 | 33 | ＜4B | 100 |
| Relatively more blue China ink 1 | Relatively fill a prescription 1 | L1B14 | Stable | 23.7 | 34 | 3B | 100 |
| Relatively more blue China ink 2 | Relatively fill a prescription 2 | L1B14 | Stable | 20.3 | 33.5 | ＜4B | 100 |
| Relatively more blue China ink 3 | Relatively fill a prescription 3 | L1B14 | Stable | 19.1 | 34 | 2B | 100 |
Last table clearly disclose the enforcement of using The compounds of this invention red black 1～3, implement green ink 1～3, implement blue China ink 1～3 with use Sartomer N120 redder black 1～3, relatively green ink 1～3, relatively more blue China ink 1～3 are compared down, all have preferable hardness, preferable performance is particularly arranged on the water stability of red pigment.
Embodiment 3
For further comparing in the embodiment of the invention 2, the ink of the embodiment of the invention and comparing embodiment is in the performance of practical application, with the ink of the ink of 9 kinds of embodiment and the 9 kinds of comparing embodiments HP51626 ink-jet casket of packing into separately, measure ink-jet ink-droplet with relatively ink-jet performance with ink droplet moulding visualizer, as table 7 and Figure 1A～Fig. 1 C, shown in Fig. 2 A～Fig. 2 C:
Table 7
| The ink numbering | Jet speed | The ink-jet performance |
| Implement red black 1 | 2m/sec | Ink-jet is too short |
| Redder black 1 | Jelly | Jelly |
| Implement red black 2 | 3m/sec | Ink-jet is very steady |
| Redder black 2 | 5m/sec | The ink-jet meeting is inclined to one side |
| Implement red black 3 (Figure 1A) | 5m/sec | Ink-jet is very steady |
| Redder black 3 (Fig. 2 A) | 6m/sec | The ink-jet meeting is inclined to one side |
| Implement green ink 1 | 8m/sec | Ink-jet is very steady |
| Compare green ink 1 | 8m/sec | The long-pending China ink of ink-jet meeting |
| Implement green ink 2 | 8m/sec | Ink-jet is very steady |
| Compare green ink 2 | 8m/sec | The long-pending China ink of ink-jet meeting |
| Implement green ink 3 (Figure 1B) | 8m/sec | Ink-jet is very steady |
| Compare green ink 3 (Fig. 2 B) | 8m/sec | The long-pending China ink of ink-jet meeting |
| Implement blue China ink 1 | 8m/sec | Ink-jet is very steady |
| Relatively more blue China ink 1 | 8m/sec | The long-pending China ink of ink-jet meeting |
| Implement blue China ink 2 | 8m/sec | Ink-jet is very steady |
| Relatively more blue China ink 2 | 8m/sec | The long-pending China ink of ink-jet meeting |
| Implement blue China ink 3 (Fig. 1 C) | 8m/sec | Ink-jet is very steady |
| Relatively more blue China ink 3 (Fig. 2 C) | 8m/sec | The long-pending China ink of ink-jet meeting |
Can know that with Figure 1A～Fig. 1 C, Fig. 2 A～Fig. 2 C discovery ink-jet stability of the present invention is preferable by table 7.Hence one can see that, and arborescence of the present invention is more suitable for as ink jet ink composition than catenate photocurable oligomer.
The above only is preferred embodiment of the present invention; so it is not in order to limit scope of the present invention; any personnel that are familiar with this technology; without departing from the spirit and scope of the present invention; can do further improvement and variation on this basis, so the scope that claims were defined that protection scope of the present invention is worked as with the application is as the criterion.
Claims (14)
1. a sphere that contains many UV crosslinking reactive group is divided dendritic structural compounds, it is characterized in that, comprises:
One core, its structure are the isocyanuric acid ester; And
The dendritic substituting group of a plurality of branches, its skeleton contains a plurality of polar functional groups, and end is the UV crosslinking reactive group.
2. the sphere of many UV of containing crosslinking reactive group according to claim 1 is divided dendritic structural compounds, it is characterized in that, and the dendritic substituting group of these a plurality of branches, its skeleton also comprises a plurality of aromatic bases.
3. the sphere of many UV of containing crosslinking reactive group according to claim 1 is divided dendritic structural compounds, it is characterized in that, this UV crosslinking reactive group comprises carbon-carbon double bond.
4. the sphere of many UV of containing crosslinking reactive group according to claim 1 is divided dendritic structural compounds, it is characterized in that, its structure is as follows:
In the following formula (I), R
1Be the segment after the epoxy alkane open loop;
Ar is the aromatic base with a plurality of polar functional groups; And
R
2Be the UV crosslinking reactive group, n is 1～5 integer.
5. the sphere of many UV crosslinking reactive group according to claim 4 is divided dendritic structural compounds, it is characterized in that, these polar functional groups that this Ar has are ester group and hydroxyl.
6. the sphere that many UV crosslinking reactive group volume according to claim 4 reaches is divided dendritic structural compounds, it is characterized in that, its structure is as shown in the formula shown in (II).
7. the dendritic structural compounds of spherical branch is characterized in that, the dendritic structural compounds of described spherical branch is the precursor that the sphere of described many UV of the containing crosslinking reactive group of claim 1 is divided dendritic structural compounds, and its structure is as follows:
In the following formula (III), R
1Be the segment after the epoxy alkane open loop; And
Ar is the aromatic base with a plurality of polar functional groups.
8. the spherical dendritic structural compounds that divides according to claim 7 is characterized in that this Ar also comprises following at least a substituting group: carboxylic acid group, hydroxyl or amido.
9. the spherical dendritic structural compounds that divides according to claim 7 is characterized in that its structure is as shown in the formula shown in (IV).
10. a photosensitive resin composition is characterized in that, comprising:
A) 0.02～25wt% photo-sensitive initiators;
B) sphere of 1～99.8wt% many UV of containing crosslinking reactive group according to claim 1 is divided dendritic structural compounds; And
C) other photoresponse things of 0～98.98wt%.
11. an ink jet ink composition is characterized in that, comprising:
A) solvent of 0.5～50wt%;
B) colorant of 0.5～20wt%;
C) photo-curing monomer of 1～90wt%; And
D) sphere of 1～40wt% many UV of containing crosslinking reactive group according to claim 1 is divided dendritic structural compounds.
12. ink jet ink composition according to claim 11 is characterized in that, also comprises e) light trigger of 0.1～25wt%.
13. ink jet ink composition according to claim 11 is characterized in that, this solvent comprises water, solvent or monomer.
14. ink jet ink composition according to claim 11 is characterized in that, its viscosity is between 1～35cps, and surface tension is between 20～50 milli Newton/meter, and hardness is between 4H～4B.
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