KR20070039722A - Ink jet ink composition containing cyclic diether compound or cyclic dithiolan compound - Google Patents

Abstract

The present invention provides an inkjet ink composition comprising water, a colorant, and a cyclic diether compound or a cyclic dithiolane compound, an ink cartridge comprising the same, and an inkjet recording apparatus including the ink cartridge. According to the present invention, the ink composition maintains the feathering of the ink uniformly in the concentric direction, so that the edge of the image is clear and penetration into the print medium is easy, and the drying speed is high.

Description

Ink jet ink composition containing a cyclic diether compound or a cyclic dithiolan compound {Ink jet ink composition containing cyclic diether compound or cyclic dithiolan compound}

The present invention provides an inkjet ink composition, an ink cartridge, which maintains feathering of ink uniformly in a concentric direction, so that the edge of an image is clear, and ink is easily transmitted to improve the drying speed in a print medium. An ink jet recording apparatus.

In inkjet printing, ink droplets are ejected from a nozzle at a recording head of an inkjet printer onto a print medium such as paper to form dots called "dots" to record characters and images. Ink compositions used in inkjet printing are prepared by dissolving or dispersing water-soluble dyes or pigments in a solvent such as water.

An inkjet printer can be classified into a piezoelectric method for discharging ink using a piezoletric element and a thermal method for discharging ink using a heating element according to a method of discharging ink droplets.

In inkjet printers, the nozzles are very small in diameter and ink must not block the nozzles, and nozzle clogging is caused by an increase in viscosity due to the loss of the vehicle by evaporation.

The ink composition should be able to interact with the printing medium, in particular paper, to penetrate the medium without degrading image quality due to excessive smearing. Also, printed characters should be dried quickly to avoid smearing.

There has been a continuous study of ink compositions that meet all of the above properties.

The fast drying properties of the ink composition can be improved by adding penetrants. The penetrant may be a quasisurfactant.

In US Pat. No. 5,165,968, 0.05 wt% to 6 wt% of alcohol and up to 15 wt% of glycol, ketone or glycol ether or mixtures thereof were used simultaneously to shorten the drying time of the ink and prevent nozzle clogging.

US Pat. No. 5,156,675 used a co-solvent of 2 wt% to 40 wt% to dry the ink within 1 second on plain paper, and the co-solvent used herein can be seen to include one or more glycol ethers.

In addition, in order to shorten the drying time of the ink, U.S. Patent No. 5,534,050 simultaneously discloses a semisurfactant including acetylene polyalkylene oxide, 1,2-hexanediol, 1,2-octanediol and diethylene glycol monobutyl ether. Application to adjust the drying time of the ink.

However, the glycol ether or alcohol used in the conventional ink composition may facilitate the infiltration of ink on plain paper or premium grade plain paper, which is within a few micrometers even without a coating layer and thus cannot control the penetration of the ink. When the ink does not control the direction of ink movement, the blur of ink becomes severe, and the smell is strong, and in particular, the free OH group of the end group reacts with a constituent material such as a heater or adhesive constituting the inkjet printer head, and the ink Accelerating the coglation of the device is limited or not easy to use.

Especially for high speed printing using an array head, the edge of the image is kept sharp by optimizing the feathering and blurring of ink droplets while simultaneously improving the drying speed of the printing medium for the high printing speed. It is necessary to optimize the print quality and image density by efficiently maintaining the coverage of the ink.

 Therefore, the technical problem to be achieved by the present invention is to facilitate the absorption of ink on the surface of the printing medium composed of cellulose, with or without a coating layer, as well as to maintain the movement of the ink in the printing medium layer to blur the ink It is to provide an ink composition, an ink cartridge and an inkjet recording apparatus which can not only minimize the dot size of the ink but also keep the feathering the same.

In order to achieve the above technical problem, in the first aspect of the present invention;

coloring agent; And

It provides an inkjet ink composition comprising a cyclic diether compound of Formula 1 or a cyclic dithiolane compound:

<Formula 1>

In the above formula,

X is O or S atom,

R ₁ , R ₂ , R ₃ and R ₄ are each independently H, NH ₂ , NO ₂ , carboxylic acid, sulfuric acid or phosphoric acid or salts thereof, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted alkenyl, Substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy group, cycloalkyl having 3 to 8 carbon atoms, cycloalkenyl, cycloalkynyl group, heterocyclic hydrocarbon group having 4 to 10 carbon atoms, or aromatic hydrocarbon group having 5 to 10 carbon atoms ego,

It is an integer of 2≤n≤6 and 0≤m≤4.

According to an embodiment of the present invention, the inkjet ink composition according to the present invention may include 1 part by weight to 1000 parts by weight of the compound of Formula 1 based on 100 parts by weight of the colorant.

According to another embodiment of the present invention, the cyclic dithiolan compound or the cyclic diether compound of Formula 1 may be any one of the following compounds:

(1) cyclic diether compounds

(2) Cyclic Dithiolane Compound

In a second aspect of the present invention, there is provided an ink cartridge comprising the ink composition.

In a third aspect of the present invention, there is provided an ink jet recording apparatus provided with the ink cartridge.

The inkjet ink composition according to the present invention does not occur drying at the nozzle, and is excellent in permeability to the print medium, minimizes blur, and keeps feathering the same.

Hereinafter, the present invention will be described in detail.

An inkjet ink composition according to the present invention comprises water, a colorant and a cyclic diether compound or a cyclic dithiolane compound of formula (I):

<Formula 1>

In the above formula,

X is O or S atom,

R ₁ , R ₂ , R ₃ and R ₄ are each independently H, NH ₂ , NO ₂ , carboxylic acid, sulfuric acid or phosphoric acid or salts thereof, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted alkenyl, Substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy group, carboxyalkyl having 3 to 8 carbon atoms, cycloalkenyl, cycloalkynyl group, heterocyclic hydrocarbon group having 4 to 10 carbon atoms, or aromatic hydrocarbon group having 5 to 10 carbon atoms ego,

It is an integer of 2≤n≤6 and 0≤m≤4.

It is preferable that the cyclic dithiolane compound or cyclic dithio compound of the formula (1) included in the inkjet ink composition of the present invention is any one of the following compounds.

The cyclic dithiorane compound or the cyclic diether compound of Formula 1 is because the ring portion is more similar to the aromatic ring of the colorant in the composition than the metal, preventing the compound from reacting with the nozzle surface and printing for high printing speed in high speed printing By optimizing the feathering and blurring of ink droplets while improving the drying speed in the medium, it is possible to optimize the print quality and the image density by keeping the edges of the image clear and efficiently maintaining the coverage in the printing medium. In other words, the permeation characteristics of sulfur atoms or oxygen atoms are maintained and the reactivity with the metal material is minimized. In addition, since the structure of the cellulose constituting the print medium is similar, the miscibility with the print medium is improved, so that the mobility due to the capillary phenomenon of the ink can be maintained uniformly so that the dot size of the ink can be adjusted and the feathering can be kept the same.

The content of the cyclic dithiolan compound or the cyclic diether compound of Formula 1 in the inkjet ink composition according to the present invention is preferably 1 to 1000 parts by weight, more preferably 50 to 300 parts by weight based on 100 parts by weight of the colorant. to be.

If the content is less than 1 part by weight, the desired effect cannot be obtained. If the content is more than 1000 parts by weight, the optical density is lowered, which is not preferable.

The ink composition for inkjet recording of the present invention may use water as a liquid medium. In addition, the inkjet ink composition according to the present invention may further include a water-soluble organic solvent in addition to water as a liquid medium. Examples of the water-soluble organic solvent include aliphatic monohydric alcohols, polyhydric alcohols, and polyhydric alcohol derivatives.

The aliphatic monohydric alcohol can adjust the surface tension of the ink composition to improve the permeability, dot-forming ability, and drying characteristics of the printed image on recording media such as plain paper or specialty paper. The polyhydric alcohol and its derivatives do not evaporate easily, and by lowering the freezing point of the ink composition, it is possible to improve the storage stability of the ink composition and prevent clogging of the nozzle.

Examples of the aliphatic monohydric alcohol include C ₁ -C ₁₀ lower alcohols such as methyl alcohol, ethyl alcohol, n-propyl alcohol, i-propyl alcohol, n-butyl alcohol, s-butyl alcohol and t-butyl alcohol. have. In particular, ethyl alcohol, i-propyl alcohol and n-butyl alcohol are preferred.

Examples of the polyhydric alcohols include alkylene glycols such as ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, butylene glycol, and glycerol, polyalkylene glycols such as polyethylene glycol and polypropylene glycol, and thiodiglycols. Or mixtures thereof.

Examples of the polyhydric alcohol derivatives include lower alkyl ethers of polyhydric alcohols and lower carboxylic acid esters of polyhydric alcohols. Here, ethylene glycol dimethyl ether is an example of the lower alkyl ether of the polyhydric alcohol, and ethylene glycol diacetate is an example of the lower carboxylic acid ester of the polyhydric alcohol.

As the colorant used in the present invention, a self-disperse dye, a self-disperse pigment or a pigment in which a dispersant is commonly used may be used. As an example of the colorant, C.I. Basic Black 2, C.I. Direct Yellow 44, C.I. Basic Blue 26, C.I. Direct Red 227 or Projet Fast Cyan 2 (Zeneca), Projet Fast Magenta 2 (Zeneca), Projet Fast Yellow 2 (Zeneca) and Projet Fast Black 2 (Zeneca), but are not limited to these dyes.

The ink composition for ink jet recording of the present invention may further include additives such as surfactants, pH adjusting agents, preservatives or chelating agents. Here the total content of the additive is 50 to 500 parts by weight based on 100 parts by weight of the colorant.

The ink composition for inkjet recording of the present invention can be produced by uniformly mixing the colorant, water, and the cyclic dithiolan compound or the cyclic diether compound of the formula (1) by conventional techniques.

Preferably, the ink composition of the present invention can be usefully used in an inkjet printer cartridge employing an array head.

An inkjet printer employing an array head is capable of increasing the throughput of a printer because the inkjet printer prints at a high speed by using a plurality of chips, unlike a shuttle type inkjet printer that transfers and prints one chip.

Further, an ink cartridge containing the ink composition according to the present invention can be used in an ink jet recording apparatus.

Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples. The following examples are intended to illustrate the present invention, and the scope of the present invention is not limited by the following examples.

Example

A colorant, a cyclic diether compound or a cyclic dithiolane compound and other additives were mixed with the following composition, and then water was added to make a final 100 g, which was sufficiently stirred for 30 minutes or more in a stirrer to make a uniform state. The mixture was then passed through a filter of 0.45 μm for dyes and a filter of 0.80 μm for pigments to prepare an ink composition.

The numbers in parentheses in the following table are parts by weight.

coloring agent Penetrant Other additives * water* Example 1 Carbon black (100) 1,3-dioxane-5,5-dimethanol (200) DEG (120) Glycerin (80) Surfynol 465 (16) Deionized Water (400) Example 2 D.Y 132 (100) 1,5-dithiacyclooctan-3-ol (160) Glycerin (100) Caprolactam (150) Deionized Water (400) Example 3 Cabot IJX 266 100 (magenta) 1,3-Dithiane (125) DEG 180 EG 100 Tergitol 20 Deionized Water (520) Comparative Example 1 D.B 199 (100) DEG-MBE (130) DEG (120) 1,5-PD (200) Tween 20 (30) Deionized Water (400) Comparative Example 2 Cabot IJX 273 (100) (yellow) IPA (100) EG 200 Surfynol 485 40 Deionized Water (500) Comparative Example 3 Carbon Black (100) - DEG 200 EG 150 Tergitol 20 Deionized Water (500)

Experimental Example 1: Ink Storage Stability

100 ml of the ink compositions obtained in Examples 1 to 3 and Comparative Examples 1 to 3 were placed in a heat resistant glass bottle, and then sealed at the inlet and stored in a 60 ° C. thermostat for 2 months, and then the presence or absence of sedimentation and separation of the bottom It evaluated as follows, and the result is shown in following Table 1.

(Circle): No precipitation, No layer separation.

(Triangle | delta): No precipitation, There exists layer separation.

X: precipitation occurs

Example Comparative example No. One 2 3 One 2 3 Storage stability × ○ △ ○ X X

The poor storage stability of Example 1 in Table 1 is because the colorant is a pigment.

Experimental Example 2: Rub Resistance

The ink compositions obtained in Examples 1 to 3 and Comparative Examples 1 to 3 were refilled in M-50 and C-60 cartridges to print text and solid images on general paper using an MJC-3300P Samsung printer for 24 hours in the air. After drying, rubbing the printed image by hand in a 25% 50% RH environment and visually judging.

○: Image does not stain

(Triangle | delta): An image may be slightly smeared, but a character can be read.

X: Pictures are smeared and characters cannot be read.

Example Comparative example No. One 2 3 One 2 3 Rub resistance △ ○ △ △ X X

Experimental Example 3: Water Resistance Test

Refill the ink compositions obtained in Examples 1 to 3 and Comparative Examples 1 to 3 to the M-50 and C-60 cartridges to print a stick figure (2 * 10 cm) in a printer (MJC-3300p, manufactured by Samsung) for 5 minutes. After that, 5 drops of water were dropped and dried for 24 hours, and then the water flowed down and the OD decreased as a percentage compared to the OD of the stick figure, and evaluated as follows.

A = (image after water flows OD / OD of circle bar plot) ㅧ 100 (%)

 ○: A> 95

△: 90 ≤ A <95

 X: A <90

As a result, when using the ink compositions of Examples 1 and 3, it was confirmed that the water resistance is improved to A> 95 or more.

Example Comparative example No. One 2 3 One 2 3 Water resistance ○ X ○ X △ △

 The inferior water resistance of Example 2 is due to the colorant.

Experimental Example 4: Nozzle Clogging Test

In the ink compositions obtained in Examples 1-3 and Comparative Examples 1 to 3, the color ink was refilled in the ink cartridge C-60 (Samsung Electronics), and the black ink was refilled in the ink cartridge M-50 (Samsung Electronics). ), Two weeks at low temperature (-18 ℃) and after printing the number of nozzle cleaning required to enable normal printing when the printing was measured and evaluated as follows and the results are shown in Table 1 below.

◎: Normal printing is possible when cleaning nozzle once.

○: Normal printing is possible when the nozzle is cleaned 2 ~ 4 times.

△: Normal printing is possible when the nozzle is cleaned 5-10 times.

X: Normal print impossible even if the nozzle is cleaned 10 times

Example Comparative example No. One 2 3 One 2 3 Nozzle clogging △ ○ △ ○ X X

Experimental Example 5: Color Bleeding Test

In the ink compositions obtained in Examples 1-3 and Comparative Example 1, the color ink is refilled in the ink cartridge C-60 (Samsung Electronics), and the black ink is refilled in the ink cartridge M-50 (Samsung Electronics), and the color is based on the stick figure. A bleeding pattern with black text was printed to evaluate the degree of color bleeding between the text and the background interface.

○: Image does not blur

(Triangle | delta): Although an image blurs slightly, a character can be read.

X: Images are blurred and characters cannot be read.

sample Sample A Sample B Sample C Sample D Sample E ink Example 1 Example 3 Example 1 Comparative Example 1 Example 1 Comparative Example 2 Comparative Example 3 Example 2 Comparative Example 3 Comparative Example 2 Color bleeding ○ X △ △ X

In the ink composition according to the present invention, by applying a cyclic diether compound or a cyclic dithiolane compound, the ink has excellent long-term storage stability with sufficient solubility by two oxygen atoms or sulfur atoms and at the same time an oxygen atom or a sulfur atom inside the ring Therefore, the reaction stability is also improved by contributing to improving the interaction of the colorant with the aromatic ring rather than the reactivity with the heater surface. In addition, since the structure is similar to the cellulose constituting the paper to improve the miscibility with the surface of the media, it is possible to uniformly maintain the mobility due to the capillary phenomenon of the ink to adjust the dot size of the ink and to maintain the same feathering.

Claims (5)

water; coloring agent; And An inkjet ink composition comprising a cyclic diether compound of Formula 1 or a cyclic dithiolane compound: <Formula 1>

In the above formula, X is O or S atom, R ₁ , R ₂ , R ₃ and R ₄ are each independently H, OH, NH ₂ , NO ₂ , carboxylic acid, sulfuric acid or phosphoric acid or salts thereof, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted eggs. Kenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy group, cycloalkyl having 3 to 8 carbon atoms, cycloalkenyl, cycloalkynyl group, heterocyclic hydrocarbon group having 4 to 10 carbon atoms, or aromatic aromatic having 5 to 10 carbon atoms A hydrocarbon group, It is an integer of 2 <= n <= 6 and 0 <= m <= 4. The composition of claim 1, wherein the compound of Formula 1 is included in an amount of 1 to 1000 parts by weight based on 100 parts by weight of the colorant. The composition of claim 1, wherein the compound of Formula 1 is any one of the following compounds :

An ink cartridge comprising the ink composition according to any one of claims 1 to 3. An inkjet recording apparatus comprising the ink cartridge according to claim 4.