CN101762977A - Thermosensitive CTP thermolabile imaging liquid using luminol compound as additive - Google Patents
Thermosensitive CTP thermolabile imaging liquid using luminol compound as additive Download PDFInfo
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Abstract
The invention discloses thermosensitive CTP thermolabile imaging liquid using a luminol compound as an additive, which belongs to the technical field of the application of optical information recording materials. The components of the imaging liquid are as follows: film-forming resin, dissolving-inhibiting resin, infrared dye, coloring background dye, acid-producing agent, additive and solvent. The additive comprises luminol, isoluninol, ANBPO, ABEI, AMP, AHEI, DPF, DHDHD, and (E)-6-(2,3,4-trihydroxy benzene methylamine)-2,3-dihydro phthalazine-1,4-diketone or (E)-5-(2,3,4-trihydroxy benzene methylamine) -2,3-dihydro phthalazine-1,4-diketone. The additive greatly improves the contrast of the alkali resistances before and after exposure, remarkably increases sensitivity and aging resistance of a thermosensitive CTP panel, and can also improves the development latitude of the thermosensitive CTP panel. In the invention, positive non-preheat thermosensitive CTP panels with high sensitivity, good resolution ratio, and higher pressrun are obtained respectively under conditions of different mask-making technologies.
Description
Technical field
The invention belongs to the applied technical field of optical information recording material, particularly using luminol compound is as the heat-sensitive CTP heat-sensible image-forming liquid of adjuvant.
Background technology
Hydrogen bond is atom X (fluorine, chlorine, oxygen, nitrogen etc.) the covalently bound hydrogen big with electronegativity, and is approaching as the atom Y big with electronegativity (with X identical also can), is media with hydrogen between X and Y, generates X-H ... the key of Y shape, this key is called hydrogen bond.The binding energy of hydrogen bond is 2-8 kilocalorie (Kcal).The hydrogen bond here comprise conventional hydrogen bond x-H-Y (X, Y=F, 0, N, C); Also comprise unconventional hydrogen bond, X-H-p for example, x-H-M, x-H-H, X-H-HY.P refers to p key or delocalization p key, and M refers to the late transition metal atom.Because it is hydrogen bond has stability, directivity and saturability, most important in the design of decision compound character and novel complexes.Weak interactions such as intermolecular ydrogen bonding have the characteristics of dynamic reversible, the stimulation of external environment condition are had the response characteristic of uniqueness.Utilize the interaction of hydrogen bond, relatively simple molecular cell is assembled into the supramolecular aggregation with two dimension or three-dimensional long-range order, this is a new way of functional material novel in design.Hydrogen bond is fully reflected in the without preheating positive thermosensitive CTP version.The image forming composition of without preheating positive thermosensitive CTP version comprises photo-thermal and produces acid source, film-forming resin, adjuvant, photo-thermal conversion material, coloring background dye.These materials form the supramolecular aggregation with two dimension or three-dimensional long-range order under hydrogen bond must act on, have stronger alkali resistance; In CTP plate-making imaging process, to produce acid source at photo-thermal and produce under the effect of acid, the two dimension or the three-dimensional structure of supramolecular aggregation are destroyed, and supramolecular aggregation becomes original molecular structure, thereby can be dissolved in the alkaline-based developer, thereby obtains clearly image.
Summary of the invention
The invention provides the heat-sensitive CTP heat-sensible image-forming liquid of a kind of using luminol compound as adjuvant, the luminol compounds can obviously improve the alkali-resisting contrast in exposure front and back as the use of adjuvant.
Using luminol compound provided by the invention comprises following component as the heat-sensitive CTP heat-sensible image-forming liquid of adjuvant:
1) film-forming resin, 70-90 weight portion, preferred 60-80 weight portion;
2) hinder molten resin, the 3-10 weight portion;
3) Infrared dyes, 1-5 weight portion, preferred 2-3 weight portion;
4) coloring background dye, 2-5 weight portion, preferred 2-3 weight portion;
5) acid agent, the 2-5 weight portion;
6) adjuvant, the 2-5 weight portion;
7) making the solids content of described composition is the solvent of 8-20% weight.
Adjuvant of the present invention is luminol (luminol), different luminol (iso-luminol), ANBPO, ABEI, AMP, AHEI, DPH, DHDHD, (E)-5-(2,3,4-trihydroxy benzene methylene amine)-2,3-dihydro phthalazines-1,4-diketone or (E)-6-(2,3,4-trihydroxy benzene methylene amine)-2,3-dihydro phthalazines-1, the 4-diketone, as shown below:
Gordian technique of the present invention is the application of this new additive agent in photosensitive composition.
Film-forming resin of the present invention is selected linear phenol-aldehyde resin for use, comprises in metacresol-paracresol-formaldehyde resin, metacresol-tert-butyl phenol-phenol-formaldehyde resin, metacresol-urea formaldehyde, orthoresol-formaldehyde resin, phenol-metacresol-formaldehyde resin, phenol one metacresol-paracresol-formaldehyde resin, metacresol-paracresol-formaldehyde resin, phenol-orthoresol one formaldehyde resin, phenol-paracresol-formaldehyde resin, the phenol-tert-butyl group resinox one or more.Film-forming resin is if consumption is too big, and then a little less than the molten ability of the resistance of image forming composition, poor to the resistivity of alkaline developer, membrane left rate is low in the developing process, not only influences picture resolution and dot reproduction, also can reduce the press resistance rate of the forme that is coated with.Otherwise, consumption very little, the consumption that hinders molten resin and other components must increase, but its development capability descends, be easy to produce keep on file, residual dirty phenomenon, also can reduce the resolution and the dot reproduction of image.
The molten resin of resistance of the present invention is active etherate, carboxyl phenolic resin active ester and the etherate of condensation resin of pyrogallol acetone resin or the active etherate of 1,2,3,-thrihydroxy-benzene and divinyl benzene polycondensate.
Infrared dyes in the image forming composition of the present invention is that used benzindole is cyanine dyes, step cyanine dye or λ in the traditional thermal CTP plate
MvThe infrared absorbing dye of=825-840nm (in imaging system) comprises the Japanese chemical drug PS-102 of company, the Japanese Lin Yuan commercial NK-2014 of company or NK-2268, the perhaps like product of other companies.The temperature-sensitive sensitivity is lower very little for the Infrared dyes consumption, and image quality is relatively poor; Consumption is too big, because infrared absorbing dye is a kind of alkali insoluble material, develops difficulty takes place, and increased considerably the cost of plate.
Coloring background dye of the present invention is selected the dyestuff of the background dye or the traditional PS version of thermal CTP plate material for use, comprises in alkaline bright blue, Victoria's ethereal blue, indigo, methyl violet, crystal violet, malachite green, the solvent blue one or more; In addition, also can add some complementary dyestuffs, comprise eosin, dimethyl yellow, sudan black, methyl orange, fluorescein.The addition of background dye in the thin compound of sensitization is generally the 2-5% weight of solid gross mass, preferred 2-3% weight; Complementary dyestuff addition is the 2-5% of coloring background dye.
Acid agent of the present invention is: trisbromomethyl phenyl sulfone or 1-be to methoxy-naphthyl-3, the two trichloromethyl triazines of 5-.
Solvent of the present invention selects for use the CTP version to use or traditional PS version solvent, comprises in ethylene glycol monoethyl ether, dihydroxypropane single-ether, MEK, butyl acetate, dioxane or the tetrahydrofuran one or more.When selecting general infrared absorbing dye for use, the main body solvent should be a MEK, and other solvents can be made secondary solvent.The consumption of solvent in image forming composition decided according to viscosity, the solid content of preparation thermolabile imaging liquid, the solid content of general imaging liquid is 8-20%, so the content of solvent in imaging liquid should be 80-92%, wherein the addition of secondary solvent generally is the 5-20% of main body solvent.
A kind of using luminol compound provided by the invention is as the heat-sensitive CTP heat-sensible image-forming liquid of adjuvant, the luminol compounds can obviously improve the alkali-resisting contrast in exposure front and back as the use of adjuvant, obviously improve sensitivity, the resistance to ag(e)ing of thermosensitive CTP sheet material, also can improve the development tolerance of thermosensitive CTP sheet material.The present invention has obtained sensitivity height, good resolution, the higher positive without preheating thermal CTP plate material of pressrun respectively under different mask-making technology conditions.
Below in conjunction with embodiment, the invention will be further described, rather than limit the scope of the invention.
Embodiment
One, (E)-5-(2,3,4-trihydroxy benzene methylene amine)-2,3-dihydro phthalazines-1,4-diketone synthetic
Embodiment 1:
The luminol that in the four-hole bottle that has stirrer, condenser pipe, constant pressure funnel and thermometer, adds 8.85g, the toluene of 200mL, heating makes its dissolving as far as possible, in reaction bulb, add 2,3 of 7.70g, 4-tri hydroxybenzaldehyde again, in mixed liquor, add the 3mL glacial acetic acid, 105 ~ 110 ℃ of reflux 5h, suction filtration gets a kind of red solid while hot; Above-mentioned red solid is placed 100mL toluene, 60 ℃ of supersound washing 30min, suction filtration while hot, 60 ℃ of vacuum drying 24h of gained red solid, product 14.1g, productive rate 90.1%.
Embodiment 2:
The luminol that in the four-hole bottle that has stirrer, condenser pipe, constant pressure funnel and thermometer, adds 4.5g, the toluene of 120mL, heating makes its dissolving as far as possible, in reaction bulb, add 2,3 of 4.2g, 4-tri hydroxybenzaldehyde again, in mixed liquor, add the 2mL glacial acetic acid, 80 ~ 90 ℃ of reflux 3.5h, suction filtration gets a kind of red solid while hot; Above-mentioned red solid is placed 60mL toluene, 50 ℃ of supersound washing 20min, suction filtration while hot, 50 ℃ of vacuum drying 24h of gained red solid, product.
Embodiment 3:
The luminol that in the four-hole bottle that has stirrer, condenser pipe, constant pressure funnel and thermometer, adds 10.5g, the toluene of 250mL, heating makes its dissolving as far as possible, in reaction bulb, add 2,3 of 10.2g, 4-tri hydroxybenzaldehyde again, in mixed liquor, add the 4.0mL glacial acetic acid, 115 ~ 125 ℃ of reflux 5h, suction filtration gets a kind of red solid while hot; Above-mentioned red solid is placed 135mL toluene, 80 ℃ of supersound washing 40min, suction filtration while hot, 85 ℃ of vacuum drying 24h of gained red solid, product.
Two, (E)-6-(2,3,4-trihydroxy benzene methylene amine)-2,3-dihydro phthalazines-1,4-diketone synthetic
Embodiment 1:
The different luminol that in the four-hole bottle that has stirrer, condenser pipe, constant pressure funnel and thermometer, adds 8.85g (0.05mol), the toluene of 150mL, heating makes its dissolving as far as possible, in reaction bulb, add 2,3 of 7.70g (0.05mol) again, the 4-tri hydroxybenzaldehyde, in mixed liquor, add the 3mL glacial acetic acid, 105 ~ 110 ℃ of reflux 3h, suction filtration gets a kind of red solid while hot.Above-mentioned red solid is placed 100mL toluene, 60 ℃ of supersound washing 30min, suction filtration while hot, 60 ℃ of vacuum drying 24h of gained red solid, product 14.6g, productive rate 93.4%.
Embodiment 2:
The different luminol that in the four-hole bottle that has stirrer, condenser pipe, constant pressure funnel and thermometer, adds 6.0g, the toluene of 120mL, heating makes its dissolving as far as possible, in reaction bulb, add 2,3 of 4.5g, 4-tri hydroxybenzaldehyde again, in mixed liquor, add the 2mL glacial acetic acid, 85 ~ 95 ℃ of reflux 5h, suction filtration gets a kind of red solid while hot; Above-mentioned red solid is placed 70mL toluene, 45 ℃ of supersound washing 40min, suction filtration while hot, 50 ℃ of vacuum drying 24h of gained red solid, product.
Embodiment 3:
The different luminol that in the four-hole bottle that has stirrer, condenser pipe, constant pressure funnel and thermometer, adds 11.0g, the toluene of 250mL, heating makes its dissolving as far as possible, in reaction bulb, add 2,3 of 9.5g, 4-tri hydroxybenzaldehyde again, in mixed liquor, add the 4.0mL glacial acetic acid, 115 ~ 125 ℃ of reflux 7.5h, suction filtration gets a kind of red solid while hot; Above-mentioned red solid is placed 120mL toluene, 80 ℃ of supersound washing 25min, suction filtration while hot, 80 ℃ of vacuum drying 24h of gained red solid, product.
Three, using luminol compound is as the preparation of the heat-sensitive CTP heat-sensible image-forming liquid of adjuvant
Embodiment 1:
Get Japanese NK-2014 infrared absorbing dye 0.3g, alkaline bright blue 0.27g, crystal violet 0.03g, acid agent be 1-to methoxy-naphthyl-3, the two trichloromethyl triazines of 5-, i.e. S-triazine 0.2g is produced in Beijing Normal University's experiment chemical plant, luminol 0.2g, the BX-20 phenolics 8.09g that the RuiShiDa Chemical Engineering Co., Ltd., Benxi City produces, the active etherate 0.9g of condensation resin of pyrogallol acetone resin, ethylene glycol monoethyl ether 113g;
At first infrared absorbing dye NK-2014, alkaline bright blue and crystal violet are dissolved in the ethylene glycol monoethyl ether, after treating thoroughly dissolving, add phenolics and other components again, filter core with 10 μ m, 5 μ m and 0.5 μ m aperture after treating all to dissolve carries out three-stage filtration, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-1.
Embodiment 2:
Get benzindole cyanine dyes 0.1g, alkaline bright blue 0.4g, acid agent is that 1-is to methoxy-naphthyl-3, the two trichloromethyl triazines of 5-, i.e. S-triazine 0.2g, luminol 0.2g are produced in Beijing Normal University's experiment chemical plant, sky, economic and technological development zone, Weihai, Shandong becomes the BTB-225 of chemical company phenolics 4.85g, BTB-15 phenolics 3.24g, carboxyl phenolic resin active ester and etherate 0.8g, MEK 50g;
At first infrared absorbing dye benzindole cyanine dyes, alkaline bright blue are dissolved in the MEK, after treating thoroughly dissolving, add phenolics and other components again, the filter core with 8 μ m, 5 μ m and 0.5 μ m aperture carries out three-stage filtration then, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-2.
Embodiment 3:
Get the Japanese chemical drug PS-102 of company infrared absorbing dye 0.3g, crystal violet 0.3g, acid agent is trisbromomethyl phenyl sulfone 0.2g, different luminol 0.3g, sky, economic and technological development zone, Weihai, Shandong becomes the BTB-26 of chemical company phenolics 8.19g, the active etherate 0.32g of 1,2,3,-thrihydroxy-benzene and divinyl benzene polycondensate, ethylene glycol monoethyl ether 64g, MEK 49g;
At first the infrared absorbing dye Japan chemical drug PS-102 of company, crystal violet are dissolved in ethylene glycol monoethyl ether and the MEK mixed solvent, after treating thoroughly dissolving, add phenolics and other components again, filter core with 10 μ m, 5 μ m and 0.5 μ m aperture after treating all to dissolve carries out three-stage filtration, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-3.
Embodiment 4:
Get Japanese NK-2014 infrared absorbing dye 0.2g, indigo 0.3g, acid agent is that 1-is to methoxy-naphthyl-3, the two trichloromethyl triazines of 5-, i.e. S-triazine 0.2g, different luminol 0.4g are produced in Beijing Normal University's experiment chemical plant, from U.S.'s import 140 resin 7.2g, the active etherate 0.5g of condensation resin of pyrogallol acetone resin, dihydroxypropane single-ether 64g, MEK 49g;
At first with in infrared absorbing dye NK-2014, the indigo mixed solvent that is dissolved in dihydroxypropane single-ether and MEK, after treating thoroughly dissolving, add phenolics and other components again, filter core with 10 μ m, 5 μ m and 0.5 μ m aperture after treating all to dissolve carries out three-stage filtration, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-4.
Embodiment 5:
Get step cyanine dye 0.2g, solvent blue 0.26g, acid agent is that 1-is to methoxy-naphthyl-3, the two trichloromethyl triazines of 5-, i.e. S-triazine 0.3g, luminol 0.2g are produced in Beijing Normal University's experiment chemical plant, RuiShiDa Chemical Engineering Co., Ltd., Benxi City BX-20 phenolics 4.85g, BX-20 phenolics 3.24g, carboxyl phenolic resin active ester and etherate 0.6g, dihydroxypropane single-ether 80g;
At first infrared absorbing dye is gone on foot cyanine dye, solvent blue is dissolved in the dihydroxypropane single-ether, after treating thoroughly dissolving, add phenolics and other components again, the filter core with 9 μ m, 5 μ m and 0.5 μ m aperture after treating all to dissolve carries out three-stage filtration, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-5.
Embodiment 6:
Get benzindole cyanine dyes 0.3g, alkaline bright blue 0.27g, crystal violet 0.03g, acid agent is trisbromomethyl phenyl sulfone 0.5g, ANBPO 0.4g, the BX-20 phenolics 7.5g that the RuiShiDa Chemical Engineering Co., Ltd., Benxi City produces, the active etherate 0.8g of 1,2,3,-thrihydroxy-benzene and divinyl benzene polycondensate, butyl acetate 90g;
At first infrared absorbing dye benzindole cyanine dyes, alkaline bright blue and crystal violet are dissolved in the butyl acetate, after treating thoroughly dissolving, add phenolics and other components again, filter core with 10 μ m, 5 μ m and 0.5 μ m aperture after treating all to dissolve carries out three-stage filtration, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-6.
Embodiment 7:
Get Japanese NK-2014 infrared absorbing dye 0.4g, alkaline bright blue 0.5g, crystal violet 2.5g, acid agent be 1-to methoxy-naphthyl-3, the two trichloromethyl triazines of 5-, be that S-triazine 0.3g is produced in Beijing Normal University experiment chemical plant, ANBPO 0.3g, sky, economic and technological development zone, Weihai, Shandong becomes the BTB-225 of chemical company phenolics 4.85g, BTB-15 phenolics 3.24g, the active etherate 1.0g of condensation resin of pyrogallol acetone resin, dioxane 120g;
At first infrared absorbing dye NK-2014, alkaline bright blue and crystal violet are dissolved in the dioxane, after treating thoroughly dissolving, add phenolics and other components again, filter core with 11 μ m, 5 μ m and 0.5 μ m aperture after treating all to dissolve carries out three-stage filtration, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-7.
Embodiment 8:
Get the Japanese chemical drug PS-102 of company infrared absorbing dye 0.4g, Victoria's ethereal blue 0.27g, indigo 0.03g, acid agent be 1-to methoxy-naphthyl-3, the two trichloromethyl triazines of 5-, i.e. S-triazine 0.4g is produced in Beijing Normal University's experiment chemical plant, ANBPO 0.2g, sky, economic and technological development zone, Weihai, Shandong becomes the BTB-26 of chemical company phenolics 8.0g, carboxyl phenolic resin active ester and etherate 0.9g, tetrahydrofuran 130g;
At first with the infrared absorbing dye Japan chemical drug PS-102 of company, Victoria's ethereal blue and indigo being dissolved in the tetrahydrofuran, after treating thoroughly dissolving, add phenolics and other components again, filter core with 12 μ m, 5 μ m and 0.5 μ m aperture after treating all to dissolve carries out three-stage filtration, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-8.
Embodiment 9:
Get Japanese NK-2014 infrared absorbing dye 0.5g, alkaline bright blue 0.27g, malachite green 0.03g, acid agent be 1-to methoxy-naphthyl-3, the two trichloromethyl triazines of 5-, be that S-triazine 0.5g is produced in Beijing Normal University experiment chemical plant, ABEI 0.4g is from U.S.'s import 140 resin 8.5g, carboxyl phenolic resin active ester and etherate 0.95g, ethylene glycol monoethyl ether 55g, MEK 49g;
At first infrared absorbing dye NK-2014, alkaline bright blue and malachite green are dissolved in ethylene glycol monoethyl ether and the MEK mixed solution, after treating thoroughly dissolving, add phenolics and other components again, filter core with 10 μ m, 4 μ m and 0.5 μ m aperture after treating all to dissolve carries out three-stage filtration, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-9.
Embodiment 10:
Get Japanese NK-2014 infrared absorbing dye 0.2g, alkaline bright blue 0.18g, methyl violet 0.08g, acid agent are that 1-is to methoxy-naphthyl-3, the two trichloromethyl triazines of 5-, be that S-triazine 0.3g, ABEI 0.5g, RuiShiDa Chemical Engineering Co., Ltd., Benxi City BX-20 phenolics 3.0g are produced in Beijing Normal University experiment chemical plant, BX-20 phenolics 5.5g, the active etherate 0.45g of condensation resin of pyrogallol acetone resin, tetrahydrofuran 65g, MEK 45g;
At first infrared absorbing dye NK-2014, alkaline bright blue and methyl violet are dissolved in tetrahydrofuran and the MEK mixed solvent, after treating thoroughly dissolving, add phenolics and other components again, filter core with 10 μ m, 5 μ m and 0.5 μ m aperture after treating all to dissolve carries out three-stage filtration, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-10.
Embodiment 11:
Get the Japanese chemical drug PS-102 of company infrared absorbing dye 0.3g, alkaline bright blue 0.27g, crystal violet 0.03g, acid agent be 1-to methoxy-naphthyl-3, the two trichloromethyl triazines of 5-, be that S-triazine 0.5g is produced in Beijing Normal University experiment chemical plant, ABEI 0.5g, the BX-20 phenolics 8.8g that the RuiShiDa Chemical Engineering Co., Ltd., Benxi City produces, the active etherate 0.55g of 1,2,3,-thrihydroxy-benzene and divinyl benzene polycondensate, ethylene glycol monoethyl ether 30g, butyl acetate 70g;
At first the infrared absorbing dye Japan chemical drug PS-102 of company, alkaline bright blue and crystal violet are dissolved in ethylene glycol monoethyl ether and the butyl acetate mixed solvent, after treating thoroughly dissolving, add phenolics and other components again, filter core with 10 μ m, 6 μ m and 0.5 μ m aperture after treating all to dissolve carries out three-stage filtration, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-11.
Embodiment 12:
Get Japanese NK-2014 infrared absorbing dye 0.3g, Victoria's ethereal blue 0.27g, crystal violet 0.03g, acid agent is trisbromomethyl phenyl sulfone 0.2g, ANBPO 0.2g, and sky, economic and technological development zone, Weihai, Shandong becomes the BTB-225 of chemical company phenolics 2.0g, BTB-15 phenolics 5.5g, the active etherate 0.65g of condensation resin of pyrogallol acetone resin, butyl acetate 20g, dioxane 80g;
At first infrared absorbing dye NK-2014, Victoria's ethereal blue and crystal violet are dissolved in butyl acetate and the dioxane mixed solvent, after treating thoroughly dissolving, add phenolics and other components again, filter core with 10 μ m, 5 μ m and 0.2 μ m aperture after treating all to dissolve carries out three-stage filtration, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-12.
Embodiment 13:
Get Japanese NK-2268 infrared absorbing dye 0.3g, alkaline bright blue 0.27g, crystal violet 0.03g, acid agent be 1-to methoxy-naphthyl-3, the two trichloromethyl triazines of 5-, be that S-triazine 0.2g is produced in Beijing Normal University experiment chemical plant, ABEI 0.3g, sky, economic and technological development zone, Weihai, Shandong becomes the BTB-26 of chemical company phenolics 8.19g, carboxyl phenolic resin active ester and etherate 0.75g, ethylene glycol monoethyl ether 40g, MEK 60g;
At first infrared absorbing dye NK-2268, alkaline bright blue and crystal violet are dissolved in ethylene glycol monoethyl ether and the MEK mixed solvent, after treating thoroughly dissolving, add phenolics and other components again, filter core with 10 μ m, 5 μ m and 0.3 μ m aperture after treating all to dissolve carries out three-stage filtration, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-13.
Embodiment 14:
Get step cyanine dye 0.5g, indigo 0.27g, crystal violet 0.03g, acid agent be 1-to methoxy-naphthyl-3, the two trichloromethyl triazines of 5-, i.e. S-triazine 0.2g is produced in Beijing Normal University's experiment chemical plant, (E)-5-(2,3,4-trihydroxy benzene methylene amine)-2,3-dihydro phthalazines-1,4-diketone 0.3g is from U.S.'s import 140 resin 8.19g, the active etherate 0.85g of 1,2,3,-thrihydroxy-benzene and divinyl benzene polycondensate, ethylene glycol monoethyl ether 30g, MEK 50g;
At first infrared absorbing dye is gone on foot cyanine dye, indigo and crystal violet is dissolved in ethylene glycol monoethyl ether and the MEK mixed solvent, after treating thoroughly dissolving, add phenolics and other components again, filter core with 10 μ m, 5 μ m and 0.6 μ m aperture after treating all to dissolve carries out three-stage filtration, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-14.
Embodiment 15:
Get Japanese NK-2014 infrared absorbing dye 0.2g, solvent blue 0.1g, crystal violet 0.3g, acid agent is that 1-is to methoxy-naphthyl-3, the two trichloromethyl triazines of 5-, be that S-triazine 0.3g is produced in Beijing Normal University experiment chemical plant, (E)-5-(2,3,4-trihydroxy benzene methylene amine)-2,3-dihydro phthalazines-1,4-diketone 0.3g, RuiShiDa Chemical Engineering Co., Ltd., Benxi City BX-20 phenolics 4.85g, BX-20 phenolics 3.24g, carboxyl phenolic resin active ester and etherate 0.5g, dihydroxypropane single-ether 20g, dioxane 90g;
At first infrared absorbing dye NK-2014, solvent blue and crystal violet are dissolved in dihydroxypropane single-ether and the dioxane mixed solvent, after treating thoroughly dissolving, add phenolics and other components again, filter core with 10 μ m, 5 μ m and 0.8 μ m aperture after treating all to dissolve carries out three-stage filtration, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-15.
Embodiment 16:
Get benzindole cyanine dyes 0.3g, solvent blue 0.2g, methyl violet 0.2g, acid agent be 1-to methoxy-naphthyl-3, the two trichloromethyl triazines of 5-, be that S-triazine 0.2g is produced in Beijing Normal University experiment chemical plant, ABEI 0.3g, the BX-20 phenolics 7.5g that the RuiShiDa Chemical Engineering Co., Ltd., Benxi City produces, the active etherate 0.9g of condensation resin of pyrogallol acetone resin, ethylene glycol monoethyl ether 55g, tetrahydrofuran 35g;
At first infrared absorbing dye benzindole cyanine dyes, solvent blue and methyl violet are dissolved in ethylene glycol monoethyl ether and the tetrahydrofuran mixed solvent, after treating thoroughly dissolving, add phenolics and other components again, filter core with 10 μ m, 5 μ m and 1.0 μ m apertures after treating all to dissolve carries out three-stage filtration, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-16.
Embodiment 17:
Get Japanese NK-2268 infrared absorbing dye 0.3g, alkaline bright blue 0.1g, crystal violet 0.1g, acid agent is that 1-is to methoxy-naphthyl-3, the two trichloromethyl triazines of 5-, be that S-triazine 0.2g is produced in Beijing Normal University experiment chemical plant, (E)-6-(2,3,4-trihydroxy benzene methylene amine)-2,3-dihydro phthalazines-1,4-diketone 0.2g, sky, economic and technological development zone, Weihai, Shandong becomes the BTB-225 of chemical company phenolics 4.85g, BTB-15 phenolics 3.24g, carboxyl phenolic resin active ester and etherate 0.8g, ethylene glycol monoethyl ether 90g, MEK 20g;
At first infrared absorbing dye NK-2268, alkaline bright blue and crystal violet are dissolved in ethylene glycol monoethyl ether and the MEK mixed solvent, after treating thoroughly dissolving, add phenolics and other components again, filter core with 10 μ m, 5 μ m and 0.5 μ m aperture after treating all to dissolve carries out three-stage filtration, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-17.
Embodiment 18:
Get step cyanine dye 0.5g, alkaline bright blue 0.27g, crystal violet 0.03g, acid agent is trisbromomethyl phenyl sulfone 0.2g, (E)-6-(2,3,4-trihydroxy benzene methylene amine)-2,3-dihydro phthalazines-1,4-diketone 0.4g, sky, economic and technological development zone, Weihai, Shandong becomes the BTB-26 of chemical company phenolics 8.19g, the active etherate 0.75g of condensation resin of pyrogallol acetone resin, ethylene glycol monoethyl ether 100g, MEK 20g;
At first infrared absorbing dye being gone on foot cyanine dye, alkaline bright blue and crystal violet is dissolved in ethylene glycol monoethyl ether and the MEK mixed solvent, after treating thoroughly dissolving, add phenolics and other components again, filter core with 10 μ m, 5 μ m and 0.5 μ m aperture after treating all to dissolve carries out three-stage filtration, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-18.
Embodiment 19:
Get Japanese NK-2014 infrared absorbing dye 0.3g, alkaline bright blue 0.27g, crystal violet 0.03g, acid agent be 1-to methoxy-naphthyl-3, the two trichloromethyl triazines of 5-, i.e. S-triazine 0.2g is produced in Beijing Normal University's experiment chemical plant, (E)-6-(2,3,4-trihydroxy benzene methylene amine)-2,3-dihydro phthalazines-1,4-diketone 0.3g is from U.S.'s import 140 resin 8.19g, carboxyl phenolic resin active ester and etherate 0.8g, ethylene glycol monoethyl ether 60g, MEK 20g;
At first infrared absorbing dye NK-2014, alkaline bright blue and crystal violet are dissolved in ethylene glycol monoethyl ether and the MEK mixed solvent, after treating thoroughly dissolving, add phenolics and other components again, filter core with 10 μ m, 5 μ m and 0.5 μ m aperture after treating all to dissolve carries out three-stage filtration, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-19.
Embodiment 20:
Get Japanese NK-2014 infrared absorbing dye 0.2g, alkaline bright blue 0.18g, crystal violet 0.08g, acid agent is that 1-is to methoxy-naphthyl-3, the two trichloromethyl triazines of 5-, be that S-triazine 0.3g is produced in Beijing Normal University experiment chemical plant, (E)-6-(2,3,4-trihydroxy benzene methylene amine)-2,3-dihydro phthalazines-1,4-diketone 0.3g, RuiShiDa Chemical Engineering Co., Ltd., Benxi City BX-20 phenolics 4.85g, BX-20 phenolics 3.24g, the active etherate 0.6g of condensation resin of pyrogallol acetone resin, ethylene glycol monoethyl ether 20g, MEK 100g;
At first infrared absorbing dye NK-2014, alkaline bright blue and crystal violet are dissolved in ethylene glycol monoethyl ether and the MEK mixed solvent, after treating thoroughly dissolving, add phenolics and other components again, filter core with 10 μ m, 5 μ m and 0.5 μ m aperture after treating all to dissolve carries out three-stage filtration, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-20.
Embodiment 21:
Get Japanese NK-2014 infrared absorbing dye 0.4g, alkaline bright blue 0.15g, crystal violet 0.35g, acid agent be 1-to methoxy-naphthyl-3, the two trichloromethyl triazines of 5-, be that S-triazine 0.5g is produced in Beijing Normal University experiment chemical plant, AHEI 0.4g, the BX-20 phenolics 8.09g that the RuiShiDa Chemical Engineering Co., Ltd., Benxi City produces, carboxyl phenolic resin active ester and etherate 0.9g, ethylene glycol monoethyl ether 30g, MEK 40g;
At first infrared absorbing dye NK-2014, alkaline bright blue and crystal violet are dissolved in ethylene glycol monoethyl ether and the MEK mixed solvent, after treating thoroughly dissolving, add phenolics and other components again, filter core with 10 μ m, 5 μ m and 0.5 μ m aperture after treating all to dissolve carries out three-stage filtration, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-21.
Embodiment 22:
Get Japanese NK-2268 infrared absorbing dye 0.3g, alkaline bright blue 0.05g, crystal violet 0.25g, acid agent is trisbromomethyl phenyl sulfone 0.2g, DPH 0.2g, and sky, economic and technological development zone, Weihai, Shandong becomes the BTB-225 of chemical company phenolics 4.85g, BTB-15 phenolics 3.24g, the active etherate 0.7g of 1,2,3,-thrihydroxy-benzene and divinyl benzene polycondensate, ethylene glycol monoethyl ether 20g, MEK 40g;
At first infrared absorbing dye NK-2268, alkaline bright blue and crystal violet are dissolved in ethylene glycol monoethyl ether and the MEK mixed solvent, after treating thoroughly dissolving, add phenolics and other components again, filter core with 10 μ m, 5 μ m and 0.5 μ m aperture after treating all to dissolve carries out three-stage filtration, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-22.
Embodiment 23:
Get Japanese NK-2268 infrared absorbing dye 0.3g, alkaline bright blue 0.2g, crystal violet 0.3g, 0.01g sudan black, acid agent is that 1-is to methoxy-naphthyl-3, the two trichloromethyl triazines of 5-, i.e. S-triazine 0.2g, DPH 0.3g are produced in Beijing Normal University's experiment chemical plant, sky, economic and technological development zone, Weihai, Shandong becomes the BTB-26 of chemical company phenolics 8.19g, the active etherate 0.8g of condensation resin of pyrogallol acetone resin, ethylene glycol monoethyl ether 80g, MEK 40g;
At first infrared absorbing dye NK-2268, alkaline bright blue, crystal violet, sudan black are dissolved in ethylene glycol monoethyl ether and the MEK mixed solvent, after treating thoroughly dissolving, add phenolics and other components again, filter core with 10 μ m, 5 μ m and 0.5 μ m aperture after treating all to dissolve carries out three-stage filtration, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-23.
Embodiment 24:
Get Japanese NK-2014 infrared absorbing dye 0.3g, alkaline bright blue 0.1g, crystal violet 0.3g, 0.015g eosin, acid agent is that 1-is to methoxy-naphthyl-3, the two trichloromethyl triazines of 5-, i.e. S-triazine 0.2g, DHDHD 0.2g are produced in Beijing Normal University's experiment chemical plant, from U.S.'s import 140 resin 8.19g, the active etherate 0.55g of 1,2,3,-thrihydroxy-benzene and divinyl benzene polycondensate, ethylene glycol monoethyl ether 30g, MEK 90g;
At first infrared absorbing dye NK-2014, alkaline bright blue, crystal violet, eosin are dissolved in ethylene glycol monoethyl ether and the MEK mixed solvent, after treating thoroughly dissolving, add phenolics and other components again, filter core with 10 μ m, 5 μ m and 0.5 μ m aperture after treating all to dissolve carries out three-stage filtration, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-24.
Embodiment 25:
Get Japanese NK-2014 infrared absorbing dye 0.2g, alkaline bright blue 0.18g, crystal violet 0.08g, 0.02g methyl orange, acid agent is trisbromomethyl phenyl sulfone 0.3g, DHDHD 0.3g, RuiShiDa Chemical Engineering Co., Ltd., Benxi City BX-20 phenolics 4.85g, BX-20 phenolics 3.24g, the active etherate 0.9g of 1,2,3,-thrihydroxy-benzene and divinyl benzene polycondensate, ethylene glycol monoethyl ether 64g, MEK 49g;
At first infrared absorbing dye NK-2014, alkaline bright blue, crystal violet, methyl orange are dissolved in ethylene glycol monoethyl ether and the MEK mixed solvent, after treating thoroughly dissolving, add phenolics and other components again, filter core with 10 μ m, 5 μ m and 0.5 μ m aperture after treating all to dissolve carries out three-stage filtration, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-25.
Embodiment 26:
Get Japanese NK-2014 infrared absorbing dye 0.2g, alkaline bright blue 0.18g, crystal violet 0.08g, acid agent are trisbromomethyl phenyl sulfone 0.3g, AMP0.15g, DPH 0.15g, RuiShiDa Chemical Engineering Co., Ltd., Benxi City BX-20 phenolics 4.85g, BX-20 phenolics 3.24g, the active etherate 0.9g of 1,2,3,-thrihydroxy-benzene and divinyl benzene polycondensate, ethylene glycol monoethyl ether 64g, MEK 49g;
At first infrared absorbing dye NK-2014, alkaline bright blue and crystal violet are dissolved in ethylene glycol monoethyl ether and the MEK mixed solvent, after treating thoroughly dissolving, add phenolics and other components again, filter core with 10 μ m, 5 μ m and 0.5 μ m aperture after treating all to dissolve carries out three-stage filtration, makes heat-sensitive CTP heat-sensible image-forming liquid CTP-26.
Four, as a comparison case, select a embodiment as a comparison case 1 among the patent CN03143500.9 of Beijing Normal University application for use
Comparative Examples 1:
Get the BTB-328g that sky, economic and technological development zone, Weihai, Shandong becomes chemical company to produce; the VRR that sky, economic and technological development zone, Weihai, Shandong becomes chemical company to produce hinders molten chaotropic agent 0.3g; this hinders the rosin that molten chaotropic agent has protecting group. resorcinol resin; the BTC-141 that sky, economic and technological development zone, Weihai, Shandong becomes chemical company to produce; be hexakis-methoxy methylated melamine 0.2g; 2; 1; 4-diazo naphthoquinone sulphonyl oxygen phthalimide ester 0.5g; the acid agent 0.4g of embodiment 1; the NK-2268 infrared absorbing dye 0.5g of Japan Lin Yuan company; solvent blue 0.1g; cyclohexanone 90g is with the dissolving of embodiment 1; preparation obtains heat-sensitive CTP heat-sensible image-forming liquid CTP-27 with filter method.
The evaluation and the comparing result of table 1 positive without preheating heat-sensitive CTP plate
| The plate sequence number | Coating weight (g/m 2) | Dissolvent residual rate (%) | Temperature-sensitive sensitivity (mJ/cm 2) | Resolution (dpi) | Dot reproduction (%) |
| ??CTP-1 | ??1.60 | ??≤3 | ??120 | ??250 | ??1-99 |
| ??CTP-2 | ??1.65 | ??≤3 | ??125 | ??250 | ??1-99 |
| ??CTP-3 | ??1.61 | ??≤3 | ??130 | ??250 | ??1-99 |
| ??CTP-4 | ??1.62 | ??≤3 | ??140 | ??250 | ??1-99 |
| ??CTP-5 | ??1.59 | ??≤3 | ??130 | ??250 | ??1-99 |
| ??CTP-6 | ??1.65 | ??≤3 | ??125 | ??250 | ??1-99 |
| ??CTP-7 | ??1.64 | ??≤3 | ??130 | ??250 | ??1-99 |
| ??CTP-8 | ??1.60 | ??≤3 | ??135 | ??250 | ??1-99 |
| ??CTP-9 | ??1.65 | ??≤3 | ??145 | ??250 | ??1-99 |
| ??CTP-10 | ??1.62 | ??≤3 | ??140 | ??250 | ??1-99 |
| ??CTP-11 | ??1.65 | ??≤3 | ??130 | ??250 | ??1-99 |
| ??CTP-12 | ??1.62 | ??≤3 | ??130 | ??250 | ??1-99 |
| ??CTP-13 | ??1.63 | ??≤3 | ??140 | ??250 | ??1-99 |
| ??CTP-14 | ??1.59 | ??≤3 | ??140 | ??250 | ??1-99 |
| ??CTP-15 | ??1.55 | ??≤3 | ??120 | ??250 | ??1-99 |
| ??CTP-16 | ??1.62 | ??≤3 | ??135 | ??250 | ??1-99 |
| ??CTP-17 | ??1.59 | ??≤3 | ??130 | ??250 | ??1-99 |
| ??CTP-18 | ??1.63 | ??≤3 | ??145 | ??250 | ??1-99 |
| ??CTP-19 | ??1.64 | ??≤3 | ??140 | ??250 | ??1-99 |
| ??CTP-20 | ??1.60 | ??≤3 | ??120 | ??250 | ??1-99 |
| ??CTP-21 | ??1.65 | ??≤3 | ??125 | ??250 | ??1-99 |
| The plate sequence number | Coating weight (g/m 2) | Dissolvent residual rate (%) | Temperature-sensitive sensitivity (mJ/cm 2) | Resolution (dpi) | Dot reproduction (%) |
| ??CTP-22 | ??1.61 | ??≤3 | ??130 | ??250 | ??1-99 |
| ??CTP-23 | ??1.62 | ??≤3 | ??140 | ??250 | ??1-99 |
| ??CTP-24 | ??1.59 | ??≤3 | ??130 | ??250 | ??1-99 |
| ??CTP-25 | ??1.58 | ??≤3 | ??130 | ??250 | ??1-99 |
| ??CTP-26 | ??1.65 | ??≤3 | ??120 | ??250 | ??1-99 |
| ??CTP-27 | ??1.90 | ??3.8 | ??175 | ??200 | ??2-98 |
The thermosensitive CTP plate-making testing machine that the temperature-sensitive sensitometry adopts Creo Co., Ltd to provide is measured. and resolving power determination adopts on the all-victorious 800 heat-sensitive plate-making machines and directly measures with designated software.Dot reproduction is density reflectometer ICPlate 2 mensuration with X-rite.Developer solution is Kodak's commerce positive thermosensitive CTP version developer solution.
Conclusion: utilize basic composition of the present invention suitably to adjust, under different mask-making technology conditions, obtained sensitivity height, good resolution, the higher positive without preheating thermal CTP plate material of pressrun respectively.
Claims (10)
1. using luminol compound is characterized in that as the heat-sensitive CTP heat-sensible image-forming liquid of adjuvant, and it comprises following component:
1) film-forming resin of 70-90 weight portion;
2) the molten resin of the resistance of 3-10 weight portion;
3) Infrared dyes of 1-5 weight portion;
4) coloring background dye of 2-5 weight portion;
5) acid agent of 2-5 weight portion;
6) adjuvant of 2-5 weight portion;
7) making the solids content of described composition is the solvent of 8-20% weight.
2. using luminol compound according to claim 1 is as the heat-sensitive CTP heat-sensible image-forming liquid of adjuvant, it is characterized in that described adjuvant is luminol, different luminol, ANBPO, ABEI, AMP, AHEI, DPH, DHDHD, (E)-6-(2,3,4-trihydroxy benzene methylene amine)-2,3-dihydro phthalazines-1,4-diketone or (E)-5-(2,3,4-trihydroxy benzene methylene amine)-2,3-dihydro phthalazines-1, the 4-diketone, structure is as follows:
3. a kind of using luminol compound according to claim 1 is as the heat-sensitive CTP heat-sensible image-forming liquid of adjuvant, it is characterized in that, described film-forming resin is a linear phenol-aldehyde resin, comprises metacresol-paracresol-formaldehyde resin, metacresol-tert-butyl phenol-phenol-formaldehyde resin, metacresol-urea formaldehyde, orthoresol-formaldehyde resin, phenol-metacresol-formaldehyde resin, phenol one metacresol-paracresol-formaldehyde resin, metacresol-paracresol-formaldehyde resin, phenol-orthoresol one formaldehyde resin, phenol-paracresol-formaldehyde resin, or in phenol-tert-butyl group resinox one or more.
4. using luminol compound according to claim 1 is as the heat-sensitive CTP heat-sensible image-forming liquid of adjuvant, it is characterized in that the molten resin of described resistance is active etherate, carboxyl phenolic resin active ester and the etherate of condensation resin of pyrogallol acetone resin or the active etherate of 1,2,3,-thrihydroxy-benzene and divinyl benzene polycondensate.
5. using luminol compound according to claim 1 is characterized in that as the heat-sensitive CTP heat-sensible image-forming liquid of adjuvant described Infrared dyes is that benzindole is cyanine dyes, step cyanine dye or λ in imaging system
MvThe infrared absorbing dye of=825-840nm.
6. using luminol compound according to claim 1 is as the heat-sensitive CTP heat-sensible image-forming liquid of adjuvant, it is characterized in that, described coloring background dye is the dyestuff of the background dye or the traditional PS version of thermal CTP plate material, comprises in alkaline bright blue, Victoria's ethereal blue, indigo, methyl violet, crystal violet, malachite green or the solvent blue one or more.
7. using luminol compound according to claim 1 is characterized in that as the heat-sensitive CTP heat-sensible image-forming liquid of adjuvant, described acid agent be trisbromomethyl phenyl sulfone or 1-to methoxy-naphthyl-3, the two trichloromethyl triazines of 5-.
8. using luminol compound according to claim 1 is as the heat-sensitive CTP heat-sensible image-forming liquid of adjuvant, it is characterized in that, described solvent is used or traditional PS version solvent for the CTP version, comprises in ethylene glycol monoethyl ether, dihydroxypropane single-ether, MEK, butyl acetate, dioxane or the tetrahydrofuran one or more.
9. using luminol compound according to claim 2 is characterized in that described (E)-5-(2,3,4-trihydroxy benzene methylene amine)-2 as the heat-sensitive CTP heat-sensible image-forming liquid of adjuvant, 3-dihydro phthalazines-1, and the synthetic method of 4-diketone is:
The luminol that in the four-hole bottle that has stirrer, condenser pipe, constant pressure funnel and thermometer, adds the 4-12 weight portion, the toluene of 100-300 parts by volume, heating makes its dissolving, in reaction bulb, add 2,3 of 3-11 weight portion, 4-tri hydroxybenzaldehyde again, in mixed liquor, add 1.5-4.5 parts by volume glacial acetic acid, 80-130 ℃ of reflux 2-8h, suction filtration gets a kind of red solid while hot; Above-mentioned red solid is placed 50-150 parts by volume toluene, 30-90 ℃ of supersound washing 15-45min, suction filtration while hot, 30-90 ℃ of vacuum drying 12-36h of gained red solid gets final product;
The pass of described weight portion and parts by volume is g/ml or kg/l.
10. using luminol compound according to claim 2 is characterized in that described (E)-6-(2,3,4-trihydroxy benzene methylene amine)-2 as the heat-sensitive CTP heat-sensible image-forming liquid of adjuvant, 3-dihydro phthalazines-1, and the synthetic method of 4-diketone is:
The different luminol that in the four-hole bottle that has stirrer, condenser pipe, constant pressure funnel and thermometer, adds the 4-12 weight portion, the toluene of 100-300 parts by volume, heating makes its dissolving, in reaction bulb, add 2,3 of 3-11 weight portion, 4-tri hydroxybenzaldehyde again, in mixed liquor, add 1.5-4.5 parts by volume glacial acetic acid, 80-130 ℃ of reflux 2-8h, suction filtration gets a kind of red solid while hot; Above-mentioned red solid is placed 50-150 parts by volume toluene, 30-90 ℃ of supersound washing 15-45min, suction filtration while hot, 30-90 ℃ of vacuum drying 12-36h of gained red solid gets final product;
The pass of described weight portion and parts by volume is g/ml or kg/l.
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