GB2171107A - Photosensitive resin composition - Google Patents
Photosensitive resin composition Download PDFInfo
- Publication number
- GB2171107A GB2171107A GB08603366A GB8603366A GB2171107A GB 2171107 A GB2171107 A GB 2171107A GB 08603366 A GB08603366 A GB 08603366A GB 8603366 A GB8603366 A GB 8603366A GB 2171107 A GB2171107 A GB 2171107A
- Authority
- GB
- United Kingdom
- Prior art keywords
- meth
- acrylate
- group
- composition
- polymer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/12—Polymers provided for in subclasses C08C or C08F
- C08F290/126—Polymers of unsaturated carboxylic acids or derivatives thereof
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
-
- A—HUMAN NECESSITIES
- A63—SPORTS; GAMES; AMUSEMENTS
- A63F—CARD, BOARD, OR ROULETTE GAMES; INDOOR GAMES USING SMALL MOVING PLAYING BODIES; VIDEO GAMES; GAMES NOT OTHERWISE PROVIDED FOR
- A63F9/00—Games not otherwise provided for
- A63F9/24—Electric games; Games using electronic circuits not otherwise provided for
- A63F2009/2448—Output devices
- A63F2009/247—Output devices audible, e.g. using a loudspeaker
- A63F2009/2476—Speech or voice synthesisers, e.g. using a speech chip
Abstract
There is hereby provided a photosensitive resin composition suitable for a relief printing plate having an excellent resistance to a water based ink, whereby water or a water like solvent can be employed as a developing solution, which comprises; (i) a polymer (A) having a molecular weight of 5,000 to 500,000 which contains an amino group and a polymerizable double bond moiety, e.g. a butadiene/ethyl arcrylate/acrylonitrile/dimethylaminoethyl acrylate copolymer, (ii) a monomer (B) having an alpha , beta -ethylenically unsaturated bond and a free acid group which can quaternize the nitrogen atom of the polymer (A), e.g. the half-ester of phthalic acid with 2-hydroxyethyl acrylate, or 2-hydroxyethyl acryloyl phosphate, or 2-acrylamide-2-methylpropane sulphonic acid, (iii) a photopolymerizable unsaturated compound (C), and (iv) a photopolymerization initiator (D). r
Description
SPECIFICATION
Photosensitive resin composition
Field of the invention
The present invention relates to a photosensitive resin composition, more particularly a photosensitive resin composition suitable for a relief printing plate having an excellent resistance to water based and oil based ink, whereby water or an aqueous solvent can be employed as a developing solution.
The photosensitive resin composition ofthe present invention is suitable not only for the relief printing plate, but also for an offset printing plate, a screen and a resist.
Background of the invention
There have been known photosensitive com positions for the relief printing plate comprising various type of base resins such as a liquid unsaturated polyester, polyvinyl alcohol, a water soluble polyamide, an alcohol-soluble polyamide, a styrene copolymer, 1 2-polybutadiene and the I ke. The composition based on the liquid unsaturated polyester is inconvenient for handling ortreating because of its liquid form. In addition, there is a problem that the composition requiresthe use of an alkali solution or a specified air-knife for developing.
The composition based on the polyvinyl alcohol or the water-soluble polyamide has a merit that water can be employed in developing, but it has a demerit which awaterbaseinkcan not be employed in printing because of its poor water-resistance. The composition based on cellulose acetate succinate requires use of an alkali solution and it does not have a a resistance to the aqueous ink. When the base resin isthealcohol-solublepolyamide,an inflammable alcohol hastobeusedfordeveloping,which is a significant defect in environmental safety. The use of the styrene-isoprene-styrene block copolymer as the base resin requires (as a developing solvent) a halogenic organic solvent, which is also a defect in environmental safety for workers.
The object of the present invention provides a photosensitive resin composition especially suitable for a relief printing plate having an excellent resist anceto water based ink, wherebywater or an aqueous solvent can be employed as a developing solution.
Summary of the invention
The present invention provides a photosensitive resin composition which comprises; (i) a polymer (A) having a molecularweight of 5,000 to 50,000 which contains an amino group and a polymerizable double bond moiety, (ii) a monomer (B) having an a,#-ethylenically unsaturated bond a free acid group which can quaternizethe nitrogen atom ofthe polymer (A), (iii) a photopolymerizable unsaturated compound (C), and (iv) a photopolymerization initiator (D).
Detailed description of the present invention:
In the composition of the present invention, the polymer (A) isquaternized bythemonomer(B)to become water-soluble or water-dispersible. This composition is formed into a sheet which is adhered onto a suitable substrate, such as steel, aluminum or plastics.
The photosensitive layer is exposed to an ultraviolet lightthrough a negative film to copolymerize the polymer (A), the monomer (B) and the photopolymerizable unsaturated compound (C), which exposed part becomes water-insoluble. On the other hand, the unexposed partwhich has not been copolymerized can be dissolved and removed easily with water to complete the development of the relief plate.
Accordingly, the polymer (A) of the present invention contains the amino group atom in such an amount that the polymer becomes water-soluble or water-dispersible when the polymer is quaternized by the monomer (B). Also, the polymer (A) has the polymerizable double-bond moiety in such an amountthat it can be copolymerized with the photopolymerizable unsaturated compound (C) to form a water-insoluble polymer, and, in addition, the polymer (A) has sufficient molecularweightto form a water-insoluble material. The double-bond moiety is not necesarily present in the polymer (A) in such an amountthatthe double-bond forms all of waterinsoluble materials. This insolubilization is mainly accomplished bythe monomer (B) andthe photo- polymerizable unsaturated compound (C).
The polymer (A) used in the present invention can be prepared by copolymerizing the following components:
(a) 3 to 50 mole %, preferably 10 to 30 mole % of an a,#-ethylenically unsaturated monomer having an amino group,
(b) 5to 95 mole %, preferably 20to 60 mole % of polymerizable unsaturated monomer, and
(c) O to 90 mole %, preferably 20 to 60 mole % of a conjugated diene monomer.
Preferably, the weight average molecularweight of the polymer (A) is within the range of 5,000 to 500,000, more preferably 10,000 to 250,000.
The a,p-ethylenically unsaturated monomer (a) having the amino group used in the polymer (A) preferably has the following formula:
wherein R1 represents a hydrogen atom ora methyl group, (CH2)n represents an ethylene,trimethylene, butylene moiety, and R4 represents a hydrogen atom, an alkyl group having 1 to4carbon atoms, an hydroxyalkyl group having 1 to 4 carbon atoms, or an alkoxyalkyl having 1 to 4 carbon atoms. Preferred examples are dimethylaminoethyl, (meth)acrylate, diethylaminoethyl (meth)acrylate, dimethylaminoethyl (meth)acrylamide, dimethylaminopropyl (meth)acrylamide and the like.
Examples of the polymerizable unsaturated monomers (b) used in the polymer (A) are styrene, a-methylstyrene, vinyltoluene, acrylonitrile, vinyl chloride, vinylidene chloride, a (meth)acrylic acid ester, (meth)acryl amide, dicyclopentenyl (meth)acrylate, dicyclopentenoxyethyl (meth )acrylate, dicyclopentenoxypropyl (meth)acrylate, a (meth)acrylic ester of diethylene glycol dicyclopentenyl monoetherand a mixture thereof. Examples of the (meth)acrylic esters are methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrvlate, 2-ethylhexyl (meth)acrylate and the like.
The resultant composition was calender-molded on a steel plate of 0.18mm in thickness, providing total thickness of about 0.5mm at about 80 C.
A negative film was contacted to the photosensitive plate undervacuum on the composition side. Then the composition was exposed with a chemical lamp of distanceof6cmforoneminutefollowed by removing the negative film and washing with a nylon brush inwaterat40Cfor2minutestoobtaina relief image faithful to the negative film having the ShoreAhardnessof95~.
When this was tried in printing over a kraftpaper with a Stacktypeflexographic press by using the water based ink, the sharp image was maintained for morethan2hoursat50 m/min. In addition,when a 2.5 cm x 5.0 cm sample of this plate was dipped for 2 hours at400C in the water solution containing 1 wt%
of Na2CO3 and 5 wt% of butyl cellosolve, the surface
of the sample was swelled 6.4% ofthe thickness of
the sample. It showed thatthe composition has
excellent water-resistance.
Comparative Example 1
The photosensitive resin composition was pre
paredfromthefollowing ingredients;
Ingredients Parts by weight Water-soluble polyamide resin 3) 80
Tetraethyleneglycol 10
Acrylamide 6
N,N'-methylene bisacrylamide 2
Benzoin isobutyl ether 2.5
2,6-di-t-butylcatechol 0.4
p-methoxyphenol 0.1
3) The water-soluble polyamide resin having hyd
rogen atoms at a-position ofthe poly -capramide substituted for dimethylamino group in the amount of 52 mole %.
The above ingredients were mixed at roomtemper- ature by a press kneader, and then the mixture was
extruded to a rod shape with an extruder. The
extruded stock was calender-molded on a color
galvanized plate of 0.3mm thickness to obtain a
photosensitive composition sheet having thetotal
thickness of 0.96mm.
The composition sheet was made up as generally
described in Example 1 to obtain a releaf image of 0.66mm thickness faithful to the negativefilm having ShoreA hardness of960. When a 2.5 cm x5.0 cm sampleofthisplatewasdippedfor2hoursat400Cin the solution containing 1 wt% ofNa2CO3and5wt% of butyl cellosolve, the surface of the sample was
swelled more than 20% of the thickness of the
sample.
Example 2
The photosensitive resin composition was prepared by mixingthefollowing ingredients;
Ingredients Parts by weight
Copolymer resin of Example 1 50 2-hydroxyethyl acryloyl phosphate 4.8
Phenoxyethyl acrylate 23.9
1,6-hexandiol acrylate 23.9
2,2-dimethoxy-2-phenyl acetophenone 2.16
2,6-di-t-butylcatechol 0.24
The resultant composition was calender-molded on a steel panel of 0.18mm inthickness,providing total thickness of about 0.5m m at about 800C.
The resultant resin composition was exposed as generally described in Example 1 followed by washing with the nylon brush in water at 40 C for 50 seconds to obtain a releaf image faithful to the negative film having Shore A hardness of 84 . When a 2.5cm x5.0 sample ofthis plate was dipped for 2 hours at 40 C in the water solution containing 1 wt% of Na2CO3 and 5 wt% of butyl cellosolve, the surface ofthe sample was swelled 7.9% of the thickness of the sample. In addition when printing was conducted atthe speed of 150 mimic on the kraft paperwith the press described in Example 1 by using the relief plate obtained in the above method, the sharp image was maintained for more than 2 hours.
Example 3
The photosensitive resin composition was prepared by mixing thefollowing ingredients; Ingredients Parts by weight Copolymer resin of Example 1 50
2-acrylamide-2-methylpropane- 4.8
sulfonic acid
U rethane compound of 2-hydroxyethyl 23.9
acrylate and butylisocyanate
1,6-hexandiol acrylate 23.9
2,2-dimethoxy-2-phenyl acetophenone 2.16
2,6-di-t-butylcatechol 0.24
The resultant composition was calender-molded on a steel panel of 0.18mm in thickness, providing total thickness of about 1.9mm at about 800C.
The resultant resin composition was exposed as generally described in Example 1 followed by washing with the nylon brush inwaterat40 Cfor 1 minutes to obtain a releaf image faithful to the negative film having the Shore A hardness of 76 .
When a 2.5 cm x 5.0 cm sample of this plate was dipper for 2 hours at 40 C in the water solution 1 wt% of Na2CO3 and 5 wt% of butyl cellosolve, the surface ofthe sample was swelled 9.6% of the thickness of the sample. In addition when printing was conducted for 1 hour as generally described in Example 2, the sharp image was maintained.
Claims (10)
1. A photosensitive resin composition which comprises;
(i) a polymer (A) having a molecularweight of 5,000 to 500,000 which contains an amino group and a polymerizable double bond moiety,
(ii) a monomer (B) having an a,p-ethylenically unsaturated bond and afreeacidgroupwhich can quaternizethenitrogen atom of the polymer (A),
(iii) a photopolymerizable unsaturated com pound (C), and (iv) a photopolymerization initiator (D).
2. The composition of claim 1 in which the
polymer (A) is prepared by copolymerizing the
following components:
(a) 5 to 95 mole % of an x,P-ethylenically unsaturated monomer having an amino group,
(b) 5 to 95 mole % of a polymerizable unsaturated
monomer, and
(c) Oto90mole% ofaconjugateddiene monomer.
3. The composition of claim 2 in which the a,(3-ethylenically unsaturated monomer (a) having the amine group is a (meth)acrylate or (meth)acrylamide having the amino group.
4. The composition of claim 2 in which the polymerizable unsaturated monomer (b) is a (meth)acrylateora (meth)acrylamide.
5. The composition of claim 1 in which the monomer (B) having an os,ss-ethylenically unsaturated bond is selected from the group consisting of monomers having the following formulas:
wherein R1 represents a hydrogen atom ora methyl group, R2 represents (CH2)n wherein n is an integer of
one to 6, and R3 represents an alkylene group having
1 to 6 carbon atoms or a phenylene group.
6. The composition of claim 1 inwhichthe
photopolymerizable compound (C) is a compound
having a ethylene bond in the terminal.
7. The composition of claim 1 in which the photopolymerization initiator is a benzoin ether, acetophenon, benzophenone and a ketal derivative.
8. A photosensitive resin composition which containins;
(i) a polymer (A) 30to 90% by weigh (ii) amonomer(B) 1 to 60% by weigh (iii) a photopolymerizable 5to70% byweight
unsaturated compound (C)
(iv) a photopolymerization 0.01 to20% by weight
initiator (D)
9. A photo-polymer printing plate developable with water, comprising a support and a coating thereon ofthewater-developable photo-sensitive composition of any one of claims 1 to 8.
Examples ofthe conjugated diene monomers (C) are conjugated diene hydrocarbons such as butadiene, isoprene, dimethylbutadiene, choloroprene and the like.
The monomer (B) having the o:,(3-ethylenically unsaturated bond contains a free acid group which can quaternize the polymer (A) to make itself water-soluble and a polymerizable unsaturated bond which can be photopolymerized along with the photopolymerizable unsaturated compound (C)to make itself water-insoluble.
Examples of the free acid groups are a carboxylic acid group, a phosphoric acid group, a sulfonic acid group and the like. Preferred monomers have the following formulas:
wherein R1 represents a hydrogen atom or a methyl group, R2 represents (CH2)n wherein n is an integer of 1 to 6, and R3 represents an alkylene group having 1 to 6 carbon atoms or a phenylene group.
Examples of the o:,#-ethylenically unsaturated monomers (B) containing the carboxylic acid group are (meth)acrylic acid, maleic acid, fumaric acid, citraconic acid and the like. Examples of the monomers (B) containing the sulfonic acid group are 2 acrylamido - 2 - methylpropane - sulphonic acid and the like. Also examples of the monomers (B) containing the phosphoric acid group are 2-hydroxyethyl acryloyl phosphate, 2-hydroxypropyl acryloyl phos phate,2 - hydroxy - ss - chloropropyl acryloyl phosphate and the like. Above monomers can be used individually or can be mixed up.
The photopolymerizable unsaturated compound (C) ofthe present invention may be of conventional types which are non-gaseous ethylenically unsaturated compound that preferably contain at least one ethylene group in the terminal and also can be dissolved with the above polymer (A). Examples of the compounds (C) are unsaturated carboxylic esters such as ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acry late, 1 ,4-butanediol di(meth)acrylate, 1 ,6-hexanediol di(meth)acrylate, 1 ,4-cyclohexanediol di(meth)acrylatel, propylenediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, pentaerythritol tetra(meth)acrylate; unsaturated amides such as N.N'-methylene bisacrylamide, N,N'-ethylene bisacrylamide, N,N'hexamethylenebisacrylamide, N,N'-xylylenebisacrylamide, N-('3-hydrnxyethyl)methaycrylamide, N,N' bis((3-hydroxyethyl)acrylamide; urethanized (meth)acrylates derived from 2-hydroxyethyl (meth)acrylate and an isocyanate compound; monoor di-(meth)acrylates of diepoxy polyethers modified by aromatic polyhydric alcohols such as bisphenol, a noboraccompound and the like; a mixturethereof.
Preferably the compounds having poor hydrophilic nature are employed.
Examples of the photopolymerization initiators (D) are benzoin ethers such as benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin butyl ether; benzophenones such as benzophenone, o-benzoylmethyl benzoate and the like; xanthones such as xanthone, thioxanthone, 2-chlorothioxan- thone, 2-isopropylthioxanthone and the like; acetophenones such as acetophenone, trichloroace tophenone,2,2-diethoxyacetophenone,2,2- dimethoxyacetophenone 2,2 - dimethoxy - 2 - phenyl acetophenone and the like; benzyl - 2 - ethyl anthraquinone; methylbenzoyl formate; 2 - hydroxy- 2 - methyl - propiophenone; 2 - hydroxy - 4 - isopropyl - 2 - methlpropiophenone; 1 -hydroxycyciohexyl phenyl ketone; and a mixture thereof.
The photosensitive resin composition ofthe present invention contains: (i) 30 to 90%, preferably 40 to 80% by weight of the above polymer (A); (ii) sufficient amount of o:,'3-ethylenically unsaturated monomer (B) having an acid group to quater nize 20 to 250 mole % ofthe amino group in the polymer (A), generally 1 to 60% by weight; (iii) 5to70%, preferably 10 to 55% by weight of the photopolymerizable unsaturated compound (C); and (iv) 0.01 to 20%, preferably 0.05 to 10% byweightof the photopolymerization initiator (D);
The present composition may optionally contain a polymerization inhibitor such as hydroquinone, p methoxyphenol, 2,6 - di -t - butylcatechol, benzoquinone, naphthoquinone, 2,6 - diphenyl - p benzoquinone, phenothiazine, and the like; a dye such as eosine Y, rose bengal, malachite green,
methylene blue and the like; and a plasticizer such as
a dialkyl phthalate, a dialkyl fumarate, a dialkyl
sebacate, a dialkyl itaconate, an alkyl phosphate, (poly)ethylene glycol, a (poly)ethylene glycol ester, a
(poly)ethylene glycol ether.
The photosensitive resin composition ofthe present invention is molded to an uniform sheet of 0.01 to
1 0.00mum by a molding method such as an extrusion molding, a calender molding and the like and the sheet is bonded to a substrate through an adhesive layer. The photosensitive layer is exposed with ultraviolet while the composition is polymerized on the part of the exposure to obtain a polymerized latent image which is insoluble in water, an alkali solution, and an organic solvent. The unexposed part is removed with waterto form a relief printing plate which has an excellent resistance to an aqueous ink.
The photosensitive resin composition ofthe present invention is essentially water-soluble, butthe
plate obtained from the composition is easily
polymerized to make itself water-insol u ble. Therefore, an ultraviolet is exposed through a negative film to the plate and washed with waterto obtain the plate for printing having the imagefaithful to thefilm.
Accordingly, development can be conducted with water, and the plate is water-insoluble so that print
can be conducted with a water based ink. The
photosensitive resin composition ofthe present
invention is suitable not onlyforthe relief printing
plate, but also for an offset printing plate, a screen
and a resist.
The present invention are illustrated bythefollow
ing examples, which are not to be construed as
limiting the invention to their details. All parts and percentages inthe examples are byweightunless otherwise specified.
EXAMPLE
Example 7
The photosensitive resin composition was prepared by mixing the following ingredients;
Ingredients Parts by weight Copolymerresin ') 40
VISCOAT-2,000 2) 14
Hydroxypropyl acrylate 17
1,6-hexandiol diacrylate 16.6
2,2-dimethoxy-2-phenyl acetophenone 2.16
2,6-di-t-butylcatechol 0.24 7'The copolymer resin (MW=1 00,000) prepared from 15 parts of butadiene, 20 parts of ethyl acrylate, 25 parts of acrilonitrile, and 40 parts of dimethylaminoethyl acrylate.
2) The half-ester of 2-hydroxyethyl acrylate with phtalic acid, which is commercially available from OSAKAYUKI KAGAKU Co. LTD.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70064985A | 1985-02-12 | 1985-02-12 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8603366D0 GB8603366D0 (en) | 1986-03-19 |
| GB2171107A true GB2171107A (en) | 1986-08-20 |
| GB2171107B GB2171107B (en) | 1989-08-02 |
Family
ID=24814355
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8603366A Expired GB2171107B (en) | 1985-02-12 | 1986-02-11 | Photosensitive resin composition |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPH06100828B2 (en) |
| AU (1) | AU582628B2 (en) |
| CA (1) | CA1271870A (en) |
| DE (1) | DE3604402C2 (en) |
| GB (1) | GB2171107B (en) |
| NZ (1) | NZ215095A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0337403A2 (en) * | 1988-04-15 | 1989-10-18 | Tokyo Ohka Kogyo Co., Ltd. | Photopolymerizable compositions |
| US5102773A (en) * | 1988-11-03 | 1992-04-07 | Basf Aktiengesellschaft | Photosensitive recording material comprising carboxyl-containing polymeric binder having ethylenically unsaturated side groups and β-amino alcohols |
| US5143819A (en) * | 1991-01-25 | 1992-09-01 | W. R. Grace & Co.-Conn. | Aqueous developing, photocurable composition, photosensitive articles having layers made therefrom and method of improving those articles |
| EP0564918A2 (en) * | 1992-04-04 | 1993-10-13 | Hoechst Aktiengesellschaft | Light-curable elastomeric mixture and recording material for flexographic printing plates obtained therefrom |
| US5344747A (en) * | 1988-04-15 | 1994-09-06 | Tokyo Ohka Kogyo Co., Ltd. | Photopolymerizable compositions |
| EP0624474A2 (en) * | 1993-05-12 | 1994-11-17 | Seiko Epson Corporation | Printing heads for use in ink jet printing and method for producing the same |
| US5922510A (en) * | 1988-04-15 | 1999-07-13 | Tokyo Ohka Kogyo Co., Ltd. | Photopolymerizable compositions |
| US8232043B2 (en) | 2005-11-18 | 2012-07-31 | Agfa Graphics Nv | Method of making a lithographic printing plate |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2639728B2 (en) * | 1989-04-27 | 1997-08-13 | 富士写真フイルム株式会社 | Photosensitive lithographic printing plate |
| US5736298A (en) * | 1992-10-02 | 1998-04-07 | Japan Synthetic Rubber Co., Ltd. | Water developable photosensitive resin composition |
| WO1994023341A1 (en) * | 1993-03-31 | 1994-10-13 | Toyo Ink Manufacturing Co., Ltd. | Reactive microgel, photosensitive resin composition containing the same, and flexographic plate material |
| JP3011864B2 (en) * | 1994-12-09 | 2000-02-21 | 日本ペイント株式会社 | Water developable photosensitive resin composition |
| JP2000305267A (en) | 1999-04-22 | 2000-11-02 | Jsr Corp | Photosensitive resin composition |
| JP5206434B2 (en) * | 2009-01-14 | 2013-06-12 | 星光Ｐｍｃ株式会社 | Photosensitive resin composition for letterpress production |
| CN116199822B (en) * | 2023-04-24 | 2023-08-15 | 有研工程技术研究院有限公司 | Carboxyl-containing gold resinate and negative-tone photo-etching organic gold slurry and preparation method thereof |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5190603A (en) | 1975-01-31 | 1976-08-09 | HIKARIKAYOGATAKANKOSEIJUSHISOSEIBUTSU | |
| JPS5310648A (en) * | 1976-07-19 | 1978-01-31 | Japan Synthetic Rubber Co Ltd | Photosensitive resin compositions |
| GB1599281A (en) * | 1977-01-10 | 1981-09-30 | Ici Ltd | Photopolymerisable composition |
| DE3215513C3 (en) * | 1981-04-27 | 1994-07-14 | Hitachi Chemical Co Ltd | Photosensitive resin composition |
| JPS57190045A (en) * | 1981-05-19 | 1982-11-22 | Toyobo Co Ltd | Photosensitive resin composition |
| JPS57192461A (en) * | 1981-05-22 | 1982-11-26 | Toyobo Co Ltd | Photosensitive resin composition |
| US4440850A (en) * | 1981-07-23 | 1984-04-03 | Ciba-Geigy Corporation | Photopolymerisation process with two exposures of a single layer |
| JPS5868740A (en) * | 1981-10-21 | 1983-04-23 | Japan Synthetic Rubber Co Ltd | Photoresist laminate of heat resistant film |
| JPS58102230A (en) | 1981-12-15 | 1983-06-17 | Hitachi Chem Co Ltd | Photosensitive resin compositon |
| CA1203107A (en) * | 1982-08-31 | 1986-04-15 | Uniroyal, Inc. | Photosensitive elastomeric polymer composition for flexographic printing plates, processable in semi- aqueous basic solution or solvent |
| JPS6051833A (en) * | 1983-07-01 | 1985-03-23 | Toray Ind Inc | Photosensitive resin composition |
| JPS61128243A (en) * | 1984-11-28 | 1986-06-16 | Asahi Chem Ind Co Ltd | Photosensitive resin composition |
-
1986
- 1986-02-11 AU AU53377/86A patent/AU582628B2/en not_active Ceased
- 1986-02-11 GB GB8603366A patent/GB2171107B/en not_active Expired
- 1986-02-11 NZ NZ21509586A patent/NZ215095A/en unknown
- 1986-02-12 DE DE19863604402 patent/DE3604402C2/en not_active Expired - Fee Related
- 1986-02-12 CA CA000501675A patent/CA1271870A/en not_active Expired
- 1986-02-12 JP JP61029835A patent/JPH06100828B2/en not_active Expired - Lifetime
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5344747A (en) * | 1988-04-15 | 1994-09-06 | Tokyo Ohka Kogyo Co., Ltd. | Photopolymerizable compositions |
| EP0337403A3 (en) * | 1988-04-15 | 1990-01-31 | Tokyo Ohka Kogyo Co., Ltd. | Photopolymerizable compositions |
| US5147759A (en) * | 1988-04-15 | 1992-09-15 | Tokyo Ohka Kogyo Co., Ltd. | Photopolymerizable compositions |
| US5922510A (en) * | 1988-04-15 | 1999-07-13 | Tokyo Ohka Kogyo Co., Ltd. | Photopolymerizable compositions |
| EP0337403A2 (en) * | 1988-04-15 | 1989-10-18 | Tokyo Ohka Kogyo Co., Ltd. | Photopolymerizable compositions |
| US5102773A (en) * | 1988-11-03 | 1992-04-07 | Basf Aktiengesellschaft | Photosensitive recording material comprising carboxyl-containing polymeric binder having ethylenically unsaturated side groups and β-amino alcohols |
| US5143819A (en) * | 1991-01-25 | 1992-09-01 | W. R. Grace & Co.-Conn. | Aqueous developing, photocurable composition, photosensitive articles having layers made therefrom and method of improving those articles |
| EP0564918A3 (en) * | 1992-04-04 | 1994-05-18 | Hoechst Ag | Light-curable elastomeric mixture and recording material for flexographic printing plates obtained therefrom |
| EP0564918A2 (en) * | 1992-04-04 | 1993-10-13 | Hoechst Aktiengesellschaft | Light-curable elastomeric mixture and recording material for flexographic printing plates obtained therefrom |
| US6017678A (en) * | 1992-04-04 | 2000-01-25 | Agfa-Gevaert N.V. | Photocurable elastomeric mixture and recording material obtained therefrom for the production of relief printing plates |
| EP0624474A2 (en) * | 1993-05-12 | 1994-11-17 | Seiko Epson Corporation | Printing heads for use in ink jet printing and method for producing the same |
| EP0624474A3 (en) * | 1993-05-12 | 1995-11-08 | Seiko Epson Corp | Printing heads for use in ink jet printing and method for producing the same. |
| US8232043B2 (en) | 2005-11-18 | 2012-07-31 | Agfa Graphics Nv | Method of making a lithographic printing plate |
Also Published As
| Publication number | Publication date |
|---|---|
| NZ215095A (en) | 1989-04-26 |
| CA1271870A (en) | 1990-07-17 |
| DE3604402A1 (en) | 1986-08-28 |
| JPH06100828B2 (en) | 1994-12-12 |
| AU5337786A (en) | 1986-08-21 |
| GB2171107B (en) | 1989-08-02 |
| JPS61246742A (en) | 1986-11-04 |
| AU582628B2 (en) | 1989-04-06 |
| GB8603366D0 (en) | 1986-03-19 |
| DE3604402C2 (en) | 1994-12-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 732E | Amendments to the register in respect of changes of name or changes affecting rights (sect. 32/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19980211 |