CN1990620A - Branched Structured Compound Containing Multiple UV Crosslinking Reactive Groups and Its Application - Google Patents

Abstract

The invention relates to a spherical branched structure compound containing multiple UV crosslinking reactive groups, wherein the core of the compound is an isocyanurate group, the skeleton of the compound contains a plurality of polar functional groups, and the tail end of the compound is a UV crosslinking group. The invention also provides a precursor of the compound, and applications of various compounds such as an adhesion promoter, a photosensitive resin composition and an ink-jet ink, particularly the hardness and the water stability of the ink-jet ink after jet printing can be greatly improved.

Description

Branched Structured Compound Containing Multiple UV Crosslinking Reactive Groups and Its Application

technical field

The invention relates to a spherical branched structure compound containing multiple UV crosslinking reactive groups, and particularly relates to the application of the compound in ink-jet ink compositions.

Background technique

A variety of inkjet technologies have been applied to rapid printing. The more common methods include continuous inkjet printing and drop-on-demand. The former can make use of the principle of voltage bias, such as bidirectional deflection and multidirectional deflection, to supply ink according to the way of inkjet when charged and no inkjet when not charged. The principle of the latter is usually in the following two ways: moving the piezoelectric transformer to generate pressure waves to form ink droplets, commonly known as the piezoelectric method, and the other is to form ink droplets with heat pulses, commonly known as the thermal bubble method.

The composition of the ink can be roughly divided into water-soluble, oil-soluble, solvent-based, hot-melt and light-curable. Since the mechanism of the first two types is quite dependent on the penetration, absorption and drying of ink, the latter three are more suitable for use on metals, ceramics, plastics and other non-ink-absorbing materials. The present invention is particularly related to photocurable inkjet inks. The most important and basic patent is US Pat. No. 4,303,924 which discloses the use of various low molecular weight molecules containing carbon-carbon double bonds as photocurable components. Others, such as the photocurable ink disclosed in Taiwan Province of China Patent No. 207302, or disclosed in Taiwan Province of China Patent No. 207308, are photocurable inks that use monomers, oligomers, or resins containing carbon-carbon double bonds as pigments. Curing the components and applying the pigment to the production of LCD color filters. US Patent No. 4,680,368 discloses a photocurable ink composition including polyurethane. European Patent Nos. A0465039 and A0540203 also disclose photocurable inks containing various polymerizable monomers. These patents are difficult to avoid problems such as insufficient adhesion, insufficient chemical resistance and heat resistance, and embrittlement caused by insufficient crosslinking degree. In addition, too high fluidity will cause stability problems when the pigment is dispersed. However, if the chain-like photocurable components are elongated to increase their stability, the viscosity of the ink in the inkjet cartridge will increase. To solve this problem, it is necessary to introduce a variety of photocurable monomers for fine-tuning. This will cause trouble in subsequent improvement and quality control, thereby increasing costs.

Therefore, how to further design a photocurable molecule that solves the above problems, and then apply it to inkjet inks, is a problem that needs to be solved urgently. Dendrimer has been widely used in pharmaceutical, synthesis, supramolecular chemistry and other fields in recent years due to its large number of modifiable branched chains. The application of dendrites in photocurable inks includes the polyester aminated compounds disclosed in US2005/0147834A1, but like most of the skilled in the art, the branched chain ends of this patent are also aminated compounds, and cannot be processed. Photocuring reaction. The dendrimer disclosed in US6,221,933B1 has terminal amine groups, which improves the moisture resistance of the ink sprayed on the glass surface, and can be washed with alkaline water to recycle the glass. Even though the dendron as disclosed in US6,300,388B1 has carbon-carbon double bonds that can undergo photocuring reactions, the end of the branch chain is still an aminated compound, but the double bonds placed inside the molecule rather than at the end will cause photocuring The steric barrier of the reaction and reduces the rate and degree of ink curing. In addition, many people suspend the dye chromophore at the end of the dendrimer, one of which is US2003/0096885A1, although it can improve inkjet performance, enhance light resistance, water resistance, stain resistance and other properties, it still lacks the potential of US6,300,388B1. Photocurable terminal functional groups.

The core species of dendrites is a basic but important choice. Generally, planar molecules such as triazine or benzene are used as the central molecule, but because of the aromaticity and planarity of the above two, it is difficult to cause three-dimensional cross-linking in all directions, which reduces physical properties such as hardness and light resistance. Therefore, there are many improvements in this respect, one of which is U.S. Patent Publication No. US2004/0163570A1, which uses a symmetrical silicone cage (cage) to externally connect multiple branched chains to form a multi-chain ball (non-dendritic body). It is a carbon-carbon double bond for photocuring. Although the large core of this patent can avoid the problem of steric barriers, its oversized silicone cage and unusual chemical characteristics will make further extension and improvement more difficult than dendrites with organic molecules as the core.

Contents of the invention

In view of this, the present invention particularly provides a spherical branched structure compound containing many UV crosslinking reactive groups, comprising: a core whose structure is an isocyanurate group; and a plurality of branched substituents, Its skeleton contains multiple polar functional groups, and the end is a UV crosslinking reactive group.

In the spherical branched structure containing multiple UV crosslinking reactive groups of the present invention, the skeletons of the multiple branched substituents also include multiple aromatic groups.

In the spherical branched structure containing multiple UV crosslinking reactive groups of the present invention, the UV crosslinking reactive groups include carbon-carbon double bonds.

The structure of the spherical branched structure containing multiple UV crosslinking reactive groups of the present invention can be as follows:

式(I)

Formula (I)

In formula (I), R ₁ is a chain segment after alkylene oxide ring opening; Ar is an aromatic group with multiple polar functional groups; and R ₂ is a UV crosslinking reaction group, and n is an integer of 1 to 5.

In the above formula (I), the polar functional groups of Ar may be ester groups and hydroxyl groups.

The compound of above-mentioned formula (I), its specific structure can be:

Formula (II)

The present invention also provides a spherical branched structure compound, which is the precursor of the above-mentioned spherical branched structure compound containing multiple UV crosslinking reactive groups, and its structure is as follows:

式(III)

Formula (III)

In formula (III), R ₁ is a chain segment after the ring opening of alkylene oxide, and Ar is an aromatic group with multiple polar functional groups.

In the above formula (III), the Ar may further include at least one of the following substituents: carboxylic acid group, hydroxyl group, or amino group.

The compound of above-mentioned formula (III), its specific structure can be:

式(IV)

Formula (IV)

The present invention also includes a photosensitive resin composition, including: a) 0.02 to 25 wt% photoinitiator; b) 1 to 99.8 wt% of the above-mentioned spherical branched compound with multiple UV crosslinking reactive groups; c) 0 ~98.98wt% other photosensitive reactants.

The present invention also includes an inkjet ink composition, including a) 0.5-50wt% solvent; b) 0.5-20wt% colorant; c) 1-90wt% photocurable monomer; d) 1-40wt% The above-mentioned spherical branched structure compound with multiple UV crosslinking reactive groups.

The inkjet ink composition of the present invention may also include e) 0.1-25 wt% of a photoinitiator.

In the inkjet ink composition of the present invention, the vehicle includes water, a solvent, or a monomer.

The ink-jet ink composition of the present invention has a viscosity of 1-35 cps, a surface tension of 20-50 mN/m, and a hardness of 4H-4B.

The spherical branched structure containing multiple UV crosslinking reactive groups of the present invention can be used in adhesion promoters, photosensitive resin compositions, inkjet inks, especially the spherical branch containing multiple UV crosslinking reactive groups of the present invention. The ink-jet ink of the dendritic structure can greatly improve the hardness and water stability after printing, and has good rub resistance and adhesion.

Description of drawings

FIG. 1A is an actual ink jetting diagram of red ink 3 implemented.

FIG. 1B is an illustration of actual inkjet implementation of green ink 3 .

FIG. 1C is an illustration of actual ink jetting implementing blue ink 3 .

FIG. 2A is an actual jetting diagram of comparative red ink 3. FIG.

FIG. 2B is an actual jetting diagram of comparative green ink 3. FIG.

FIG. 2C is an actual jetting diagram of comparative blue ink 3. FIG.

Detailed ways

The present invention particularly provides a spherical branched structure compound containing multiple UV crosslinking reactive groups, including a core, whose structure is isocyanuric acid ester group; multiple branched substituents, whose skeleton contains multiple aromatic group, multiple polar functional groups, and the terminal is a UV crosslinking reaction group. The polar functional groups of the spherical branched structure compound containing multiple UV crosslinking reactive groups include amide groups, amine groups, ester groups, hydroxyl groups, or ketone groups. The preferred embodiment of the present invention is ester groups, hydroxyl groups and amine groups. These polar functional groups can increase the adhesion, hardness and rub resistance of the ink after inkjet molding. Aryl groups include phenyl, pyridyl, naphthyl, anthracenyl, preferably phenyl. The UV cross-linking reactive group at the end has a different chemical environment and steric barrier than the UV cross-linking reactive group inserted in the backbone, so the molecule can undergo photocuring reaction quickly and uniformly. The above-mentioned UV crosslinking reactive groups may include carbon-carbon triple bonds, carbon-carbon double bonds, and other suitable functional groups, and a preferred embodiment of this experiment is carbon-carbon double bonds. A preferred spherical branched structure compound containing multiple UV crosslinking reactive groups has 18 ester groups, 3 amine groups, and 15 hydroxyl groups, and has 12 carbon-carbon double bonds at the end. The arrangement of ester groups, amine groups, and hydroxyl groups is not limited to a certain order or rules, and those skilled in the art can adjust the types and numbers of polar functional groups according to their needs, as long as the terminal has a UV cross-linking reactive group for photocatalysis. Curing reactions, such as compounds of the following structure:

Formula (I)

R ₁ is a chain segment after the ring opening of alkylene oxide; Ar is an aromatic group with multiple polar functional groups; R ₂ is a UV crosslinking reaction group, and n is an integer of 1-5.

A preferred embodiment includes a structure as follows:

Formula (II)

The present invention provides a dendrite whose core is an isocyanurate group, which can be used as a precursor of a spherical branched structure compound with multiple UV crosslinking reactive groups. Its structure is as follows:

式(III)

Formula (III)

The core structure is an isocyanurate group; _R1 is a chain segment after alkylene oxide ring opening; Ar is an aromatic group with multiple polar functional groups, these polar functional groups include carboxylic acid groups, hydroxyl groups, or amines The aryl group includes phenyl, pyridyl, naphthyl, anthracenyl, preferably phenyl. This precursor is not the only way to accomplish the purpose of the present invention, and there are still other possibilities for the arrangement of molecules. It is worth noting that the above-mentioned precursors can also undergo other dendrimerize reactions, and then perform subsequent steps to make their ends have UV cross-linking reactive groups. A preferred precursor has the following structural formula:

式(IV)

Formula (IV)

There are two main synthesis methods for dendrimers: divergent from inside to outside and convergent from outside to inside. If there are many "generations" between the core and the terminal functional groups, it is better to use the convergent method; if there are fewer generations, the simpler divergent method is the main method; after establishing a core with fewer generations, the divergent method can also be used. Bond with the terminal functional groups of convergent synthesis to form target molecules. In the present invention, because the generation is less, the divergent formula is used as the main synthesis strategy, but the convergent formula or both can also be synthesized. For example, starters containing isocyanurate groups as the core include trichloroisocyanuric acid, tris(2,3-epoxypropyl)-isocyanuric acid, (tris(2,3-epoxypropyl)isocyanurate), triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione), compared with A preferred starter is tris(2,3-epoxypropyl)-isocyanurate. Three (2,3-epoxypropyl)-isocyanurate is subjected to a ring-opening reaction with a nucleophile (Nucleophile) reagent in a solvent, and the nucleophile reagent includes the following compounds:

Formula (V)

Wherein C _n is a C ₁ -C ₁₀ alkyl group, and Nu is a nucleophilic functional group that is less reactive than secondary amines, including hydroxyl and primary amines protected by protecting groups (if not protected, its reactivity will be higher than that of secondary amines) , preferably Nu is hydroxyl. The nucleophilic reagent also includes other possibilities, such as 1,3,5-triaminobenzene, 1,3,5-trihydroxybenzene, or other compounds with symmetrical three nucleophilic functional groups.

After carrying out the above reaction, a dendrite intermediate with a nucleophilic reactive group at one end is obtained. The intermediate is reacted with an aromatic group having multiple polar functional groups. If the terminal functional group of the intermediate is hydroxyl and the polar functional group of the aromatic group is carboxylic acid or anhydride, an esterification reaction is carried out. If the terminal functional group of the intermediate is a primary amine (deprotection reaction is carried out first), and when the polar functional group of the aromatic group is a carboxylic acid or an anhydride, an amidation reaction is carried out. Aromatic groups having multiple polar functional groups include 1,2,3-benzenetricarboxylic anhydride, 1,2,4-benzenetricarboxylic anhydride, and 1,3,5-benzenetricarboxylate. Aromatic groups with polar functional groups also include the following structures:

Formula (VI)

C _m is a C ₁ -C ₁₀ alkyl group having a polar functional group such as an ester group or an amide group. n is an integer of 1-6, and X is a halo group, which is good for substitution reaction with the above-mentioned nucleophilic functional group.

Finally, other unreacted polar functional groups on the aromatic group, such as carboxylic acid groups, react with a compound having a UV crosslinking reactive group at one end to obtain a spherical branched compound with multiple UV crosslinking reactive groups. These polar functional groups do not react with the UV cross-linking reactive group, but react with other functional groups of the compound, such as epoxy group (for ring-opening reaction), halogen group (for substitution reaction). If the structure of the aromatic group with a polar functional group is the following formula (VI), then the compound with a UV crosslinking reactive group at the end must have a nucleophilic functional group such as a hydroxyl or an amine group to carry out a substitution reaction, rather than an epoxy group or Halo.

式(VI)

Formula (VI)

In short, as long as it is a dendrite with an isocyanurate group as the core, a UV crosslinkable functional group as the end, and a variety of polar functional groups as the backbone, under reasonable reaction conditions, it can be In the design of the present invention, the above synthetic strategies and the following examples are not limited.

The present invention also includes the application of spherical branched structural compounds with multi-UV crosslinking reactive groups to adhesion promoters, which can be used as adhesives for bonding materials such as paper, metal, ceramics, wood, glass, and plastics.

The invention provides a photosensitive resin composition, which includes 0.02-25wt% of a photoinitiator, 1-99.8wt% of the above-mentioned spherical branched compound with multiple UV crosslinking reactive groups and 0-98.98wt% of other photosensitive Reactant. Common photoinitiators include the following molecules: benzoin alkyl ether, 2,2-dimethoxy-2-phenylacetophenone, benzophenone (benzophenone), pentabromomonochlorocyclohexane, pentachlorobenzene, polychlorinated biphenyl, 2-ethylanthraquinone, 1-chloroethylnaphthalene ( 1-chloroethylnaphthalene), 2-bromoethyl ether (2-bromoethyl ether), or other suitable photoinitiators. Other photosensitive reactants such as tetraethylene glycol diacrylate (tetraethylene glycoldiacrylate, TGD), isobornyl acrylate (IBOA), inhibitors such as: 1,6-hexanediol diacrylate (1,6- Hexanediol diacrylate, HPDA). The application of the photosensitive resin includes the manufacture of negative photoresists for optoelectronic products.

The invention provides an inkjet ink composition, which includes 0.5-50wt% of solvent, which can be: 0.5-20wt% of colorant; 1-90wt% of photocurable monomer; A compound with a spherical branched structure of linked reactive groups. Stir the above composition for 10-20 minutes to obtain an inkjet ink. The solvent is an organic solvent that can dissolve other compositions. The above-mentioned colorant includes dyes or pigments, such as Pigment Red 149, Pigment Green 36, or Pigment Blue 15:3 sold by Ciba Company. The average particle size of the pigment is between 70 ~220nm, preferably 90~200nm. Photocurable monomers such as tetraethylene glycol diacrylate (tetraethylene glycol diacrylate, TGD), isobornyl acrylate (isobornyl acrylate, IBOA), inhibitors such as: 1,6-hexanediol diacrylate (1,6- hexanediol diacrylate, HPDA), 2,6-di-tert-butyl-4-methylphenol (2,6-di-tert-butyl-4-methyphenol, BHT). In a preferred embodiment, 0.1-15wt% photoinitiator is also included. Common photoinitiators include the following molecules: 2-hydroxy-1-phenyl-1-acetone (2-hydroxy-1-phenyl-propyl-1-one), benzoin alkyl ether (benzoin alkyl ether), 2, 2-dimethoxy-2-phenylacetophenone (2,2-dimethoxy-2-phenylacetophenone), benzophenone (benzophenone), pentabromomonochlorocyclohexane (pentabromomonochlorocyclohexane), pentachlorobenzene (pentacjlobenzene), Polychlorinated biphenyl, 2-ethylanthraquinone, 1-chloroethylnaphthalene, 2-bromoethyl ether, or other suitable photoinitiator.

The viscosity of the above-mentioned inkjet ink composition is between 1-35 cps, and the surface tension is between 20-50 millinewtons/meter. The ink in this viscosity range will not be too viscous to block the nozzle before ejection, nor will it be too thin to cause It cannot be molded after spraying. The hardness of the ink after injection molding is between 4H and 4B, and it has good water stability, abrasion resistance and adhesion (Cross-Cut Tester), which can be printed on non-ink-absorbing substrates such as It has good hardness and scratch resistance on metal, ceramic, glass and plastic. Furthermore, when UV light is irradiated after printing, since the photocurable UV crosslinking reactive group can increase the polymerization reaction with other monomers or oligomers, the preservation and physical properties of the printed matter can be further improved.

Preparation example one:

The first stage:

2.55g (10mmol) three (2,3 epoxypropyl)-isocyanurate (TGIC, tris (2,3-epoxypropyl) isocyanurate) and 3.75g (36mmol, 1.2 equivalents) diethanolamine (diethanolamine) After stirring at room temperature for three hours, a violent exotherm occurs. Control the temperature below 120°C. After the end of the exotherm, control the reaction temperature at 100°C and continue the reaction for 10 hours. Follow the reaction with FT-IR (Fourier Transform Infrared Spectroscopy) , the reaction is complete when the signals of 3050~3000cm ^-1 (signal of NH) and 950~810cm ^-1 (signal of epoxy group) disappear, the reaction is as follows:

(Reaction 1)

second stage:

17.28g (90mmol, 1.5 equivalents) of 1,2,4-benzenetricarboxylic anhydride (trimelticanhydride, TMA) and 100mL of N-methyl-α-pyrrolidone (NMP, N-methyl-α-pyrrolidone) were added to the above reaction and React at 90°C for 4 hours, track the reaction with FT-IR, and the reaction is complete when 1780cm ^-1 (signal of anhydride) disappears. The reaction formula is as follows:

(Reaction 2)

The third phase:

Add 17.04g (120mmol, 2 equivalents) of glycidyl methacrylate (GMA, glycidyl methacrylate) to the above reaction and react at 90°C for 6 hours to obtain the product, whose structure is as follows:

式(II)

Formula (II)

In addition, the present invention provides preferred inkjet ink embodiments and comparative examples as follows:

Example 1

Use photoinitiator (2-hydroxyl-1-phenyl-1-acetone), photocurable monomer (BHT, TGD), and dendritic compound of the present invention (Preparation Example 1) to form photocurable ink in different proportions The basic formulation of the photoinitiator is based on weight (1 part), BHT is fixed at 0.04 part, and the ratio of TGD and dendrite of the present invention is adjusted to form implementation formulas 1-3.

Table 1 recipe number Photoinitiator BHT TGD Compounds of the invention Implement Recipe 1 1 copy 0.04 parts 109.5 copies 52 copies Implement Recipe 2 1 copy 0.04 parts 142.8 copies 26 copies Implement Recipe 3 1 copy 0.04 parts 165 copies 9 servings

Then, according to the table below, the implementation formulas 1-3, co-solvent, and surfactant were mixed and stirred for ten minutes. The co-solvent is 2-pyrrolidone (2-pyrrolidone, 2PO), and the surfactant is preferably BYK 333 sold by BYK Company. Add the above mixture to water, and stir with a high-speed homogenizer at 5,000 rpm for 5 minutes and wait for the foam to disappear. The three formulations were coated on glass with a doctor blade to form a 25 micron thick film and baked at 110°C for 60 minutes, then baked at 170°C for 45 minutes and then irradiated with UV light to cure the film. The hardness test is shown in Table 2.

Table 2 batch number H ₂ O 2PO Basic recipe (12.5 servings) water stability hardness 100 grid% Implementation Film 1 20 copies 50 copies Implement Recipe 1 Stablize 5H 100 Implementation Film 2 20 copies 50 copies Implement Recipe 2 Stablize 4H 100 Implement Thin Film 3 20 copies 50 copies Implement Recipe 3 Stablize 3H 100

It can be found from Table 2 that when the proportion of dendrites of the present invention increases, the hardness of the film after photocuring can indeed be improved.

Comparative Example 1

Epoxy acrylic oligomer (Sartomer N120) is used as the formula of photocurable ink. The ratios are as follows, except that the compound of the present invention is replaced by N120, the ratios of other components are the same.

table 3 recipe number Photoinitiator BHT TGD N120 Compare Recipe 1 1 copy 0.04 parts 109.5 copies 52 copies Compare Recipe 2 1 copy 0.04 copies 142.8 copies 26 copies Compare Formula 3 1 copy 0.04 parts 165 copies 9 servings

Adhesion is the same as that of Example 1, and comparative formulas 1-3 are formed into comparative films 1-3 by the same steps, and the hardness test is performed as shown in Table 4.

Table 4 batch number H ₂ O 2PO Compare Recipe (12.5 Servings) water stability hardness 100 grid% Compare Film 1 20 copies 50 copies Compare Recipe 1 Stablize 2H 100 Compare Film 2 20 copies 50 copies Compare Recipe 2 Stablize 2H 100 Compare Thin Film 3 20 copies 50 copies Compare Formula 3 Stablize f 100

Although it can be seen from Table 4 that N120 has the same light-curing effect, but at the same ratio, the effect of the spherical dendrimer of the present invention on light-curing is better than that of the chain oligomer N120.

Example 2

Mix and stir the implementation formulas 1-3 and the pigment concentrates of L1R1, L1G03, and L1B14 to measure their properties. Grind red pigments such as Pigment Red 21, Pigment Green 03, and Pigment Blue 15:3 to obtain self-made pigments L1R21, L1G03, and L1B14. The physical properties are as follows:

table 5 paint color L1R21(red) L1G03(green) L1B14 (blue) pigment PR149 PG36 PB15:3 Pigment ratio (%) 15.1 14.9 14.9 pH value 7.9 5.5 7.7 Viscosity (cps) 7.5 90 62 Surface tension (mN/m) 47 48.9 49.8 Average particle size (nm) 198.8 91 155.8

Add the same proportion of water (7.57%), 2PO (20.83%), and surfactant BYK333 (both 0.8%) to implementation formulas 1 to 3 (Example 1) and comparative formulas 1 to 3 (Comparative Example 1). , after self-made pigments (all accounting for 58.3%), stir for 15 minutes to form the inkjet ink composition, form a 25 micron thick ink film on the glass with a scraper and bake 60 minutes with 110 ℃, then with 170 After baking at ℃ for 45 minutes, UV light was irradiated to cure the ink film, and the hardness test was performed as shown in Table 6.

Table 6 ink number formula pigment water stability Viscosity (cps) Surface tension (mN/m) hardness One hundred cells (%) Implement Red Ink 1 Implement Recipe 1 L1R21 Stablize 11.8 34.5 4H 100 Implement Red Ink 2 Implement Recipe 2 L1R21 Stablize 10.1 34.5 3H 100 Implement Red Ink 3 Implement Recipe 3 L1R21 Stablize 7.98 34 h 100 Implement Green Ink 1 Implement Recipe 1 L1G03 Stablize 8.47 33.5 4B 100 Implement Green Ink 2 Implement Recipe 2 L1G03 Stablize 7.94 33 4B 100 Implement Green Ink 3 Implement Recipe 3 L1G03 Stablize 7.87 33 4B 100 Implement Blue Ink 1 Implement Recipe 1 L1B14 Stablize 18.6 34.5 <4B 100 Implement Blue Ink 2 Implement Recipe 2 L1B14 Stablize 17.9 34 f 100 Implement Blue Ink 3 Implement Recipe 3 L1B14 Stablize 16.7 34.5 HB 100 Compare Red Ink 1 Compare Recipe 1 L1R21 jelly jelly jelly -- -- Compare Red Ink 2 Compare Recipe 2 L1R21 thicken 11.8 34.5 HB 100 Compare Red Ink 3 Compare Formula 3 L1R21 Stablize 9.53 34 HB 100 Compare Green Ink 1 Compare Recipe 1 L1G03 Stablize 8.84 32.5 <4B 100 Compare Green Ink 2 Compare Recipe 2 L1G03 Stablize 7.92 32.5 <4B 100 Compare Green Ink 3 Compare Formula 3 L1G03 Stablize 7.62 33 <4B 100 Compare Blue Ink 1 Compare Recipe 1 L1B14 Stablize 23.7 34 3B 100 Compare Blue Ink 2 Compare Recipe 2 L1B14 Stablize 20.3 33.5 <4B 100 Compare Blue Ink 3 Compare Formula 3 L1B14 Stablize 19.1 34 2B 100

The above table clearly reveals that the red ink 1-3, the green ink 1-3, the blue ink 1-3, and the comparison red ink 1-3, the green ink 1-3, and the comparison of Sartomer N120 using the compound of the present invention are clearly revealed. Compared with blue inks 1 to 3, they all have better hardness, especially in the water stability of red pigments.

Example 3

In order to further compare in the embodiment of the present invention 2, the performance of the ink of the embodiment of the present invention and the comparative embodiment in actual application, the ink of 9 kinds of embodiments and the ink of 9 kinds of comparative embodiments are respectively packed into HP51626 inkjet cartridge, with The ink drop forming observer measures the ink jet ink drop to compare the ink jet performance, as shown in Table 7 and Figure 1A-1C, Figure 2A-2C:

Table 7 ink number Inkjet speed inkjet performance Implement Red Ink 1 2m/sec inkjet too short Compare Red Ink 1 jelly jelly Implement Red Ink 2 3m/sec Inkjet is very stable Compare Red Ink 2 5m/sec Inkjet will be biased Implement Red Ink 3 (Figure 1A) 5m/sec Inkjet is very stable Compare Red Ink 3 (Figure 2A) 6m/sec Inkjet will be biased Implement Green Ink 1 8m/sec Inkjet is very stable Compare Green Ink 1 8m/sec Inkjet builds up Implement Green Ink 2 8m/sec Inkjet is very stable Compare Green Ink 2 8m/sec Inkjet builds up Implement Green Ink 3 (Figure 1B) 8m/sec Inkjet is very stable Compare Green Ink 3 (Figure 2B) 8m/sec Inkjet builds up Implement Blue Ink 1 8m/sec Inkjet is very stable Compare Blue Ink 1 8m/sec Inkjet builds up Implement Blue Ink 2 8m/sec Inkjet is very stable Compare Blue Ink 2 8m/sec Inkjet builds up Implementation of Blue Ink 3 (Figure 1C) 8m/sec Inkjet is very stable Compare Blue Ink 3 (Figure 2C) 8m/sec Inkjet builds up

From Table 7 and FIGS. 1A to 1C , and 2A to 2C , it can be clearly found that the inkjet stability of the present invention is better. It can be seen that the dendrimer of the present invention is more suitable as an inkjet ink composition than the chain photocurable oligomer.

The above description is only a preferred embodiment of the present invention, but it is not intended to limit the scope of the present invention. Any person familiar with this technology can make further improvements on this basis without departing from the spirit and scope of the present invention. Improvements and changes, so the protection scope of the present invention should be defined by the claims of the present application.

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 structurizing thing, 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 structurizing thing, 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 structurizing thing, it is characterized in that, its structure is as follows:

Formula (I)

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).

Formula (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:

Formula (III)

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).

Formula (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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