CN102566277A - Cationic polymerization imaging composition for high-sensitive photopolymerization plate - Google Patents
Cationic polymerization imaging composition for high-sensitive photopolymerization plate Download PDFInfo
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- CN102566277A CN102566277A CN2010105979320A CN201010597932A CN102566277A CN 102566277 A CN102566277 A CN 102566277A CN 2010105979320 A CN2010105979320 A CN 2010105979320A CN 201010597932 A CN201010597932 A CN 201010597932A CN 102566277 A CN102566277 A CN 102566277A
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- cationic polymerization
- image forming
- forming composition
- high sensitivity
- formaldehyde resin
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Abstract
The invention discloses a cationic polymerization imaging photosensitive composition for a photosensitive layer of a negative image high-sensitive photopolymerization plate for lithographic printing and belongs to the technical field of optical information recording materials. The cationic polymerization imaging composition contains a photosensitive monomer with silicon vinyl ether, film-forming resin, cationic photoinitiator, coloring background dye, and solvent. As the cationic polymerization imaging composition with the cationic polymerization photosensitive monomer is free of radical polymerization, the protection of a protective layer is not required; and as the photosensitive layer of the negative image high-sensitive photopolymerization plate, which has high sensitivity and pressrun, and good resolution factor, can be made by using the cationic polymerization imaging composition, a negative image violet laser CTP plate can be made.
Description
Technical field
The invention belongs to optical information recording material technology field, particularly lithography is with the cationic polymerization imaging photosensitive composition of negative high sensitivity photopolymerization plate photosensitive layer.
Background technology
In recent years, in vogue rely on digital technology organic electronicization ground is handled with calculating, storage and output graph text information, and that CTP technology (CTP technology) wherein gets most of the attention just is a kind of.The CTP technology is with the high light of directionality such as laser, scans according to digital image information, thereby does not directly make the technology of galley through the slabstone lithographic film.CTP (computer to plate) plate generally is divided into three kinds on silver salt type, photo-polymerization type, thermal imaging type (temperature-sensitive).Release use so far from the purple laser diode of Drupa2000, purple laser c TP technology develops rapidly, and the purple Wavelength of Laser of diode has reached ultraviolet region 350nm, and power is near 1w.Purple laser c TP has that luminous point is little, resolution is high; Volume is little, realize high speed easily; Can be under bright yellow safety lamp, near the operation of bright chamber; Exposure performance is highly stable reliable; Purple laser diode volume is little, the life-span is long, the degree of modularity is high, easy-maintaining is changed; Advantages such as laser imaging system low price.It is few to compare purple laser c TP thermal value with thermosensitive CTP, the flexible phenomenon of forme that few generation causes because of temperature variation, and do not need temperature-fall period to improve plate-making speed.
The purple laser c TP plate of putting down in writing in Japan and the American-European patent documentation at present all belongs to photo-polymerization type plate (JP2007171754A, WO2007077207 A
2Kodark).Photopolymerization layer is mainly become to be grouped into for these four kinds by polymerization single polymerization monomer, polymerisable film-forming resin, sensitizing coloring matter and radical polymerization initiator, takes the circumstances into consideration to add other compositions such as sensitizer, polymerization inhibitor, colorant altogether in addition.The inhibition that adopts the free radical polymerization system to be vulnerable to oxygen disturbs, so on light sensitive layer, also will be coated with layer protective layer again.The coating of protective seam has not only increased operation steps but also improved cost.
Summary of the invention
Based on above prior art, the present invention provides a kind of cationic polymerization image forming composition that is used for high sensitivity photopolymerization plate, and this image forming composition contains cationic polymerization sensitization monomer, and free radical polymerization does not take place, and need not the protection of protective seam.
Cationic polymerization image forming composition of the present invention consists of: the sensitization monomer of the siliceous vinyl ether of 10-30 weight portion, or 15-25 weight portion; The film-forming resin of 60-90 weight portion, or 70-80 weight portion, and be siliceous vinyl ether the sensitization monomer weight 2-4 doubly; 0.2-5 the cation light initiator of weight portion; 0.1-2 the coloring background dye of weight portion, or 0.5-1.5 weight portion; Solvent is 1.5-9 a times of above-mentioned solid gross mass.
Described film-forming resin is a linear phenolic resin; Be specially weight-average molecular weight at the poly(4-hydroxystyrene) of 5000-20000, gather o-hydroxy ethene or their modified product, perhaps weight-average molecular weight one or more in phenol-formaldehyde resin between 3-10 of 3000-8000, the dispersion of distribution, phenol-paracresol-formaldehyde resin, metacresol-formaldehyde resin, orthoresol-formaldehyde resin, phenol-metacresol-formaldehyde resin, phenol-orthoresol-formaldehyde resin, phenol-tert-butyl group resinox, phenol-metacresol-paracresol-formaldehyde resin, metacresol-paracresol-formaldehyde resin, metacresol-tert-butyl group resinox.Film-forming resin is if consumption is too big, and then the resistance of image forming composition is dissolved a little less than the ability, and poor to the resistivity of alkaline developer, membrane left rate is low in the developing process, not only influences image resolution ratio and dot reproduction property, also can reduce the press resistance rate of the forme that is coated with; And the film-forming resin consumption too conference make the image forming composition viscosity too big, be unfavorable for the coating.Otherwise, the film-forming resin consumption very little, though sensitivity might improve, its development capability descends, be easy to produce keep on file, residual dirty phenomenon, also can reduce image resolution ratio and dot reproduction property.Therefore select alkali solubility height and the bigger linear phenolic resin of molecular weight for use.
Described solvent is the glycol ether-ether, comprises ethylene glycol ether acetate, 1-Methoxy-2-propyl acetate, glycol methyl ether acetate; No cyclic ester comprises ethyl lactate, butyl acetate, pentyl acetate, ethyl pyruvate; Cyclic ester comprises gamma-butyrolacton; Ketone comprises acetone, butanone, cyclohexanone, methyl isobutyl ketone, 2-heptanone; Tetrahydrofuran; These solvents use separately or several kinds of mixing are used.These solvents are enough to dissolve each component and have suitable rate of drying and even, smooth coating is provided after evaporation.
Described cation light initiator is an acid agent; Be specially sulfosalt, salt compounded of iodine, triazines material, sulfonates compounds, p-toluenesulfonic acid analog derivative, sulfone class diazomethane class; Be specially PAG201, PAG202, sulfosalt 445,3, the two trichloromethyl-1-of 5-are to first chlorostyrene base triazine.
Described coloring background dye is the background dye of traditional PS version usefulness, is specially in solvent blue, alkaline gorgeous orchid, Victoria's ethereal blue, indigo, methyl violet, crystal violet, the malachite green one or more.
Said cationic polymerization image forming composition also comprises radical initiator, comprises Irgacure784 and ITX, and to improve polymerization efficiency, the consumption of radical initiator is the 8-12% of cation light initiator.
The sensitization monomer of said siliceous vinyl ether is one or more compositions of the compound of the structural unit shown in the following formula:
R in the formula
1, R
3Be CH
3Or Ar (Ar is phenyl, Bian Ji or 1-naphthyl), and have at least one to be methyl; R
4, R
5Be H or CH
3R
2, R
6Be CH
3Or vinyl ether alkoxy; N is the integer of 0-7, or is 0-3.
Described vinyl ether alkoxy is the structural unit shown in the following formula:
M is the integer of 2-6 in the formula.
The sensitization monomer of described siliceous vinyl ether is specially one or more among A-1 to A-35, B-1 to B-35, C-1 to C-35, the D-1 to D-35.
A-1 to A-35:
B-1 to B-35:
C-1 to C-35:
D-1 to D-35:
Said cationic polymerization image forming composition also comprises auxiliary dyestuff, comprises in sudan black, methyl orange, eosin, dimethyl yellow, the fluorescein one or more, and the addition of auxiliary dyestuff is the 20-80% of coloring background dye weight.
Beneficial effect of the present invention: the cationic polymerization image forming composition that contains cationic polymerization sensitization monomer provided by the invention, because free radical polymerization does not take place, so this photosensitive composition need not the protection of protective seam; Use said composition can obtain sensitivity height, good resolution, negative high sensitivity photopolymerization version photosensitive layer that pressrun is high, and then make the purple laser c TP of negative plate.
Below in conjunction with embodiment, the present invention is done further description, rather than limit scope of the present invention.
Embodiment
Preparation embodiment 1:
Monomer A-13,
is the synthetic method of 1-phenyl-1-ethyleneoxy butoxy dimethylsilane:
Get there-necked flask; Under nitrogen environment, 1-phenyl dimethylchlorosilane 8.5mL (0.0522mol) is added in the 200mL tetrahydrofuran; Triethylamine 16mL (0.1148mol), magnetic agitation, ice-water bath; Again 4-hydroxybutyl vinyl ether 13.5mL (0.1096mol) is dissolved in the 80mL tetrahydrofuran, dropwise slowly adds; Remove ice-water bath after dropwising, returned to stirring at room 2 hours; Filter, revolve and steam solvent, thick product is used the 50mL n-hexane extraction, refilters, and filtrating concentrates down at 70 ℃, and the product after concentrating extracts lower boiling impurity with the oil pump decompression, and obtaining colourless transparent liquid is clean product, and yield is 79%.
Preparation embodiment 2:
Monomer
promptly 1,1-diphenyl-7-ethyleneoxy ethoxy seven methyl tetrasiloxanes) synthetic:
With 1; 1-diphenyl-7-chlorine seven methyl tetrasiloxanes replace the 1-phenyl dimethylchlorosilane among the preparation embodiment 1; Spent glycol mono vinyl ether 10mL (0.1096mol) replaces the 4-hydroxybutyl vinyl ether among the preparation embodiment 1, and all the other reagent and consumption are identical with preparation embodiment 1 with preparation.
Embodiment 1:
Get BTB-26 metacresol-formaldehyde resin (M that east, Taixing Industrial Co., Ltd. produces
W=4000, M
n=1500) 35g adds that oneself is synthetic
Sensitization monomer 15g, mixed type triaryl hexafluoro-antimonic acid sulfosalt PAG201 (Changzhou Tronly New Electronic Materials Co., Ltd. provides) 0.5g, the gorgeous blue 0.1g of alkalescence, acetone 300g; At first with resin dissolves in acetone, stir and to make it thoroughly add other components again after the dissolving, the filter core with 10 μ m, 5 μ m, 0.5 μ m aperture filters successively then, obtains being used for the cationic polymerization image forming composition PCL-1 of high sensitivity photopolymerization plate.
With the 1%NaOH WS as developer solution.
Embodiment 2:
Get BTB-26 metacresol-formaldehyde resin (M that east, Taixing Industrial Co., Ltd. produces
W=4000, M
n=1500) 65g adds that oneself is synthetic
Sensitization monomer 20g, mixed type triaryl hexafluoro-antimonic acid sulfosalt PAG201 (Changzhou Tronly New Electronic Materials Co., Ltd. provides) 0.5g, the gorgeous blue 0.1g of alkalescence, acetone 300g; At first with resin dissolves in acetone, stir and to make it thoroughly add other components again after the dissolving, heat 30 ℃ and make its thorough dissolving; Filter core with 10 μ m, 5 μ m, 0.5 μ m aperture filters successively then, obtains being used for the cationic polymerization image forming composition PCL-2 of high sensitivity photopolymerization plate.
With the 1%NaOH WS as developer solution.
Embodiment 3:
Get BTB-26 metacresol-formaldehyde resin (M that east, Taixing Industrial Co., Ltd. produces
W=4000, M
n=1500) 65g, adding preparation embodiment 1 gained
Sensitization monomer 20g, 3, the two trichloromethyl-1-of 5-are to first chlorostyrene base triazine (the S-triazine that Inst. of Applied chemistry, Beijing Normal Univ. produces) 0.5g, the gorgeous blue 0.1g of alkalescence, acetone 300g; At first with resin dissolves in acetone, stir and to make it thoroughly add other components again after the dissolving; Heat 40 ℃ and make its thorough dissolving; Filter core with 10 μ m, 5 μ m, 0.5 μ m aperture filters successively then, obtains being used for the cationic polymerization image forming composition PCL-3 of high sensitivity photopolymerization plate.
With the 1%NaOH WS as developer solution.
Embodiment 4:
Get BTB-26 metacresol-formaldehyde resin (M that east, Taixing Industrial Co., Ltd. produces
W=4000, M
n=1500) 65g adds that oneself is synthetic
Sensitization monomer 20g, sulfosalt 445 (Beijing English power chemical industry provides) 0.5g, the gorgeous blue 0.1g of alkalescence, acetone 300g; At first with resin dissolves in acetone, stir and to make it thoroughly add other components again after the dissolving, heat 35 ℃ and make its thorough dissolving; Filter core with 10 μ m, 5 μ m, 0.5 μ m aperture filters successively then, obtains being used for the cationic polymerization image forming composition PCL-4 of high sensitivity photopolymerization plate.
With the 1%NaOH WS as developer solution.
Embodiment 5:
Get BTB-26 metacresol-formaldehyde resin (M that east, Taixing Industrial Co., Ltd. produces
W=4000, M
n=1500) 65g adds that oneself is synthetic
Sensitization monomer 20g, mixed type triaryl hexafluoro-antimonic acid sulfosalt PAG201 (Changzhou Tronly New Electronic Materials Co., Ltd. provides) 0.5g, the gorgeous blue 0.1g of alkalescence, acetone 300g; At first with resin dissolves in acetone, stir and to make it thoroughly add other components again after the dissolving, heat 32 ℃ and make its thorough dissolving; Filter core with 10 μ m, 5 μ m, 0.5 μ m aperture filters successively then, obtains being used for the cationic polymerization image forming composition PCL-5 of high sensitivity photopolymerization plate.
With the 1%NaOH WS as developer solution.
Embodiment 6:
Get BTB-26 metacresol-formaldehyde resin (M that east, Taixing Industrial Co., Ltd. produces
W=4000, M
n=1500) 65g, adding preparation embodiment 2 gained
Sensitization monomer 20g, mixed type triaryl hexafluoro-antimonic acid sulfosalt PAG201 (Changzhou Tronly New Electronic Materials Co., Ltd. provides) 0.5g, the gorgeous blue 0.1g of alkalescence, acetone 300g.At first with resin dissolves in acetone, stir and to make it thoroughly add other components again after the dissolving, heat 38 ℃ and make its thorough dissolving; Filter core with 10 μ m, 5 μ m, 0.5 μ m aperture filters successively then, obtains being used for the cationic polymerization image forming composition PCL-6 of high sensitivity photopolymerization plate.
With the 1%NaOH WS as developer solution.
Performance test
The cationic polymerization image forming composition PCL-1-6 that obtaining among the embodiment 1-6 is used for high sensitivity photopolymerization plate is spin-coated on the PS aluminum substrate of anticipating and satisfy following condition with hydro-extractor:
Aluminum plate foundation size: 1030mm * 800mm
Aluminum plate foundation thickness: 0.28-0.3mm
Grains specification: Ra=0.5-0.6 μ m
Rh＝0.3-0.35μm
Anode oxide film weight: 3-3.5g/m
2
Control the rotating speed of centrifugal coating machine, making the coating weight (in solid content) that is coated on the aluminum substrate is 1.8-2.2g/m
2, behind preliminarily dried on the centrifugal coating machine, transfer in 50 ℃ the blast drier dry 3 minutes, purple laser c TP master PPS1-PPS6.The result lists in the table 1.
The evaluation and the comparing result of the purple laser c TP of table 1 negative version
Conclusion: the photosensitive composition that utilizes the present invention to obtain has obtained sensitivity height, good resolution, the higher purple laser c TP of the photo-polymerization type plate of pressrun respectively under different mask-making technology conditions.
Claims (10)
1. a cationic polymerization image forming composition that is used for high sensitivity photopolymerization plate is characterized in that this image forming composition consists of: the sensitization monomer of the siliceous vinyl ether of 10-30 weight portion, or 15-25 weight portion; The film-forming resin of 60-90 weight portion, or 70-80 weight portion, and be siliceous vinyl ether the sensitization monomer weight 2-4 doubly; 0.2-5 the cation light initiator of weight portion; 0.1-2 the coloring background dye of weight portion, or 0.5-1.5 weight portion; Solvent is 1.5-9 a times of above-mentioned solid gross mass.
2. a kind of cationic polymerization image forming composition that is used for high sensitivity photopolymerization plate according to claim 1; It is characterized in that; Described film-forming resin is a linear phenolic resin; Be specially weight-average molecular weight at the poly(4-hydroxystyrene) of 5000-20000, gather o-hydroxy ethene or their modified product, perhaps weight-average molecular weight one or more in phenol-formaldehyde resin between 3-10 of 3000-8000, the dispersion of distribution, phenol-paracresol-formaldehyde resin, metacresol-formaldehyde resin, orthoresol-formaldehyde resin, phenol-metacresol-formaldehyde resin, phenol-orthoresol-formaldehyde resin, phenol-tert-butyl group resinox, phenol-metacresol-paracresol-formaldehyde resin, metacresol-paracresol-formaldehyde resin, metacresol-tert-butyl group resinox.
3. a kind of cationic polymerization image forming composition that is used for high sensitivity photopolymerization plate according to claim 2 is characterized in that described solvent is the glycol ether-ether, comprises ethylene glycol ether acetate, 1-Methoxy-2-propyl acetate, glycol methyl ether acetate; No cyclic ester comprises ethyl lactate, butyl acetate, pentyl acetate, ethyl pyruvate; Cyclic ester comprises gamma-butyrolacton; Ketone comprises acetone, butanone, cyclohexanone, methyl isobutyl ketone, 2-heptanone; Tetrahydrofuran; These solvents use separately or several kinds of mixing are used.
4. a kind of cationic polymerization image forming composition that is used for high sensitivity photopolymerization plate according to claim 3; It is characterized in that; Described cation light initiator is an acid agent; Be specially sulfosalt, salt compounded of iodine, triazines material, sulfonates compounds, p-toluenesulfonic acid analog derivative, sulfone class diazomethane class, be specially PAG201, PAG202, sulfosalt 445,3, the two trichloromethyl-1-of 5-are to first chlorostyrene base triazine; Described coloring background dye is the background dye of traditional PS version usefulness, is specially in solvent blue, alkaline gorgeous orchid, Victoria's ethereal blue, indigo, methyl violet, crystal violet, the malachite green one or more.
5. a kind of cationic polymerization image forming composition that is used for high sensitivity photopolymerization plate according to claim 4; It is characterized in that; This image forming composition also comprises radical initiator, comprises Irgacure784 and ITX, and the consumption of radical initiator is the 8-12% of cation light initiator.
6. according to claim 4 or 5 described a kind of cationic polymerization image forming compositions that are used for high sensitivity photopolymerization plate, it is characterized in that the sensitization monomer of siliceous vinyl ether is one or more compositions of the compound of the structural unit shown in the following formula:
R in the formula
1, R
3Be CH
3Or Ar (Ar is phenyl, Bian Ji or 1-naphthyl), and have at least one to be methyl; R
4, R
5Be H or CH
3R
2, R
6Be CH
3Or vinyl ether alkoxy; N is the integer of 0-7, or is 0-3.
7. a kind of cationic polymerization image forming composition that is used for high sensitivity photopolymerization plate according to claim 6 is characterized in that described vinyl ether alkoxy is the structural unit shown in the following formula:
M is the integer of 2-6 in the formula.
8. according to claim 4 or 5 described a kind of cationic polymerization image forming compositions that are used for high sensitivity photopolymerization plate; It is characterized in that the sensitization monomer of described siliceous vinyl ether is one or more among A-1 to A-35, B-1 to B-35, C-1 to C-35, the D-1 to D-35;
A-1 to A-35:
B-1 to B-35:
C-1 to C-35:
9. a kind of cationic polymerization image forming composition that is used for high sensitivity photopolymerization plate according to claim 7; It is characterized in that; This image forming composition also comprises auxiliary dyestuff; Comprise in sudan black, methyl orange, eosin, dimethyl yellow, the fluorescein one or more, the addition of auxiliary dyestuff is the 20-80% of coloring background dye weight.
10. a kind of cationic polymerization image forming composition that is used for high sensitivity photopolymerization plate according to claim 8; It is characterized in that; This image forming composition also comprises auxiliary dyestuff; Comprise in sudan black, methyl orange, eosin, dimethyl yellow, the fluorescein one or more, the addition of auxiliary dyestuff is the 20-80% of coloring background dye weight.
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| CN103809378A (en) * | 2014-01-26 | 2014-05-21 | 京东方科技集团股份有限公司 | Negative photoresist as well as preparation method and application method thereof |
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| JP2019011296A (en) * | 2017-06-30 | 2019-01-24 | 協立化学産業株式会社 | Novel polymerizable compound and flexible resin composition |
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| CN103809378A (en) * | 2014-01-26 | 2014-05-21 | 京东方科技集团股份有限公司 | Negative photoresist as well as preparation method and application method thereof |
| CN103941544A (en) * | 2014-01-26 | 2014-07-23 | 京东方科技集团股份有限公司 | Photoresist, and preparation method and application method thereof |
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| US9588426B2 (en) | 2014-01-26 | 2017-03-07 | Boe Technology Group Co., Ltd. | Negative photoresist and methods of preparing and using the same |
| JP2019011296A (en) * | 2017-06-30 | 2019-01-24 | 協立化学産業株式会社 | Novel polymerizable compound and flexible resin composition |
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