WO1993014864A1 - Ionic dispersing agent which can be used in aqueous dispersions - Google Patents

Ionic dispersing agent which can be used in aqueous dispersions Download PDF

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Publication number
WO1993014864A1
WO1993014864A1 PCT/NL1993/000028 NL9300028W WO9314864A1 WO 1993014864 A1 WO1993014864 A1 WO 1993014864A1 NL 9300028 W NL9300028 W NL 9300028W WO 9314864 A1 WO9314864 A1 WO 9314864A1
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Prior art keywords
dispersing agent
fatty acid
polymer
acid derivative
oligomer
Prior art date
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PCT/NL1993/000028
Other languages
French (fr)
Inventor
Jacobus Antonius Loontjens
Franciscus Johannes Marie Derks
Original Assignee
Dsm N.V.
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Publication date
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Publication of WO1993014864A1 publication Critical patent/WO1993014864A1/en

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
    • C08K5/23—Azo-compounds
    • C08K5/235—Diazo and polyazo compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/43—Compounds containing sulfur bound to nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/5399—Phosphorus bound to nitrogen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/02—Emulsion paints including aerosols
    • C09D5/024—Emulsion paints including aerosols characterised by the additives
    • C09D5/027—Dispersing agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/14—Derivatives of phosphoric acid
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/16—Amines or polyamines

Definitions

  • the invention relates to an ionic dispersing agent which can used in aqueous dispersions that comprises a hydrophobic part and a hydrophilic part.
  • dispersing agents are used to obtain stable aqueous resin dispersions, such as, for example, alkyd dispersions, acrylate dispersions and polyurethane dispersions. If a coating based on such a dispersion is applied to a substrate, the (external) durability of the coating is not optimum as a result of the presence of the known dispersing agents. In particular, the resistance to water is adversely affected by the presence o the dispersing agent.
  • the object of the invention is to provide dispersing agents which do not cause this disadvantage and which result in dispersions and coatings having all the desired properties.
  • the invention is characterised in that the hydrophobic part is a tail which can be a fatty acid derivative, a polymer or an oligomer and the hydrophilic part comprises a terminal diazo group with at least one aci derivative group coupled thereto.
  • the dispersing agent can decompose under the influence of, for example, daylight.
  • the ionic acid derivative group is able to detach from the hydrophobic section. As a result of this, the durability of the coating increases.
  • the system obtained is stable to heat. It can be stored in the dark at room temperature for a considerable period, for example several months.
  • Compounds suitable as the hydrophobic basis for the dispersing agent are fatty acid derivatives, oligomers and polymers having a molecular weight (M n ) of between 100 and 5000.
  • Examples of such compounds are vinyl ether polymers, polyesters, polypropylene glycol, polytetra- hydrofuran, acrylate resins, unsaturated polyesters and fatty acid derivatives.
  • Vinyl ether polymers, polytetrahydrofuran, fatty acid derivatives and polyesters are preferably used.
  • suitable polyesters are alkyd resins.
  • the hydrofobic tail is a fatty acid derivative.
  • Fatty acid derivatives can e.g. be chosen from the derivatives of fatty acids with 5-25 carbon atoms, preferably with more than 10 carbon atoms.
  • usefull fatty acids are the saturated fatty acids such as for example caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid and arachidic acid.
  • the fatty acid may have one or more ethylenical unsaturations, and these may have an advantageous effect on the curing of the coating.
  • usefull unsaturated fatty acids are palmitoleic acid, oleic acid, ricinolic acid, linoleic acid, linolenic acid, eleostearic acid and licanic acid.
  • the carboxylic acid group of the fatty acid may be replaced by a sulphonic acid group.
  • the hydrofobic tail is a polyvinyl ether obtained by living cationic polymerization (LCP) because of the possibility of quantitative end-capping.
  • LCP living cationic polymerization
  • chain length and chain polarity can be chosen at will, while the molecular weight distribution is very narrow (D ⁇ 1,1).
  • LCP is for instance described in M. Sawamoto, T. Higashimura, Polymer Bull. ⁇ JL 117-22 (1987).
  • the oligomer or polymer which contains at least one terminal diazo group, has good compatibility with the resin to be dispersed.
  • Another advantage of the dispersing agent according to the invention is that radicals are released on decomposition of the dispersing agent in light, as a result of which crosslinking of the resin is promoted, especially in the case of alkyd resins.
  • aromatic diazo compounds such as, for example, aryldiazosulphonates, are used.
  • Diazo compounds have been used in the past as a coating in printing processes. Decomposition of the diazo groups containing compound under the influence of light can help to change the solubility and the water affinity of the compound to facilitate the printing process.
  • US-A-3,174,860 for example a hydrophilic polyme for use in printing processes is described that has diazo sulphonate side groups. After exposure to light the diazo group decomposes and the polymer becomes completely oleophilic.
  • the polymer in US-A-3,174,860 is not constitute of a hydrophobic and a hydrophilic part, but consists of a polymer that is first completely hydrophilic and then completely hydrofobic. The diazo groups are evenly distributed along the polymer chain. This polymer is not a dispersant and cannot be used as a dispersant.
  • US-A-3,168,401 light sensitive diazo sulphonate of cyclic amines are described for use in printing plates.
  • US-A-3,168,401 does not describe a dispersing agent comprising a hydrophobic part and a hydrophilic part.
  • EP-A-339,393 aryl diazo sulphonates are described that are polymerizable and can decompose under light exposure, thereby modifying their solubility.
  • the diazo groups are randomly divided over the polymer chain and therefore the polymer does not form a dispersion agent.
  • the dispersing agents used are compounds according to formula (I) :
  • R 1 H, OR 2 , Cl, Br or I
  • R 2 (C ⁇ -Cg )-alkyl
  • X -S0 3 or -P0 3
  • M an alkali metal, alkaline earth metal, quaternary ammonium ion or H
  • the invention is further directed to a process for dispersing resin in an aqueous medium, whereby an ionic dispersing agent as described hereabove is used. This is particularly advantageous in a continuous process.
  • the dispersing agent is used in aqueous dispersion such as, for example, alkyl dispersions, aerylate dispersions and polyurethane dispersions.
  • the dispersing agent according to the invention ca be added during or before the preparation of the dispersion
  • the dispersing agent can, for example, be added during emulsification of the monomers.
  • the preparatio of the known dispersions via emulsion polymerisation can be carried out in the presence of the catalysts and chain- regulating agents customary for this reaction.
  • the dispersing agent according to the invention ca be added in amounts of between 0.01 and 10% by weight (with respect to the amount of dispersion) . Preferably, this amount is between 0.1 and 5% by weight.
  • the dispersing agent according to the invention ca also be combined with the known emulsifiers.
  • the aqueous dispersions can contain conventional co-solvents in amounts of up to, for example, 30% by weight with respect to the amount of water.
  • the dispersions obtained can be used in coating compositions and adhesive compositions.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dispersion Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Paints Or Removers (AREA)

Abstract

The invention relates to an ionic dispersing agent which can be used in aqueous dispersions. The dispersing agent is an oblong molecular structure chosen from the group consisting of fatty acid derivatives, polymers or oligomers. The dispersing agent is based on a polymer or an oligomer having a molecular weight (Mn) of between 100 and 5000. The dispersions which are obtained using the dispersing agent are used in coating compositions.

Description

IONIC DISPERSING AGENT WHICH CAN BE USED IN
AQUEOUS DISPERSIONS
The invention relates to an ionic dispersing agent which can used in aqueous dispersions that comprises a hydrophobic part and a hydrophilic part.
It is known that dispersing agents are used to obtain stable aqueous resin dispersions, such as, for example, alkyd dispersions, acrylate dispersions and polyurethane dispersions. If a coating based on such a dispersion is applied to a substrate, the (external) durability of the coating is not optimum as a result of the presence of the known dispersing agents. In particular, the resistance to water is adversely affected by the presence o the dispersing agent. The object of the invention is to provide dispersing agents which do not cause this disadvantage and which result in dispersions and coatings having all the desired properties.
The invention is characterised in that the hydrophobic part is a tail which can be a fatty acid derivative, a polymer or an oligomer and the hydrophilic part comprises a terminal diazo group with at least one aci derivative group coupled thereto.
The dispersing agent can decompose under the influence of, for example, daylight. The ionic acid derivative group is able to detach from the hydrophobic section. As a result of this, the durability of the coating increases.
The system obtained is stable to heat. It can be stored in the dark at room temperature for a considerable period, for example several months.
An ionic dispersant of a disappearing type is described in EP-A-371.640, but in that publication the dispersant contains an oxamic acid group and not a diazo group and it decomposes upon heating.
Compounds suitable as the hydrophobic basis for the dispersing agent are fatty acid derivatives, oligomers and polymers having a molecular weight (Mn ) of between 100 and 5000.
Examples of such compounds are vinyl ether polymers, polyesters, polypropylene glycol, polytetra- hydrofuran, acrylate resins, unsaturated polyesters and fatty acid derivatives. Vinyl ether polymers, polytetrahydrofuran, fatty acid derivatives and polyesters are preferably used. Examples of suitable polyesters are alkyd resins. Preferably the hydrofobic tail is a fatty acid derivative. Fatty acid derivatives can e.g. be chosen from the derivatives of fatty acids with 5-25 carbon atoms, preferably with more than 10 carbon atoms.
Examples of usefull fatty acids are the saturated fatty acids such as for example caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid and arachidic acid. The fatty acid may have one or more ethylenical unsaturations, and these may have an advantageous effect on the curing of the coating. Examples of usefull unsaturated fatty acids are palmitoleic acid, oleic acid, ricinolic acid, linoleic acid, linolenic acid, eleostearic acid and licanic acid. In an alternative the carboxylic acid group of the fatty acid may be replaced by a sulphonic acid group. In a second preference, the hydrofobic tail is a polyvinyl ether obtained by living cationic polymerization (LCP) because of the possibility of quantitative end-capping. In addition, chain length and chain polarity can be chosen at will, while the molecular weight distribution is very narrow (D < 1,1). LCP is for instance described in M. Sawamoto, T. Higashimura, Polymer Bull. ^JL 117-22 (1987).
What is achieved by the use of these oligomers and polymers is that the oligomer or polymer, which contains at least one terminal diazo group, has good compatibility with the resin to be dispersed. Another advantage of the dispersing agent according to the invention is that radicals are released on decomposition of the dispersing agent in light, as a result of which crosslinking of the resin is promoted, especially in the case of alkyd resins. Preferably, aromatic diazo compounds such as, for example, aryldiazosulphonates, are used.
Diazo compounds have been used in the past as a coating in printing processes. Decomposition of the diazo groups containing compound under the influence of light can help to change the solubility and the water affinity of the compound to facilitate the printing process.
In US-A-3,174,860 for example a hydrophilic polyme for use in printing processes is described that has diazo sulphonate side groups. After exposure to light the diazo group decomposes and the polymer becomes completely oleophilic. The polymer in US-A-3,174,860 is not constitute of a hydrophobic and a hydrophilic part, but consists of a polymer that is first completely hydrophilic and then completely hydrofobic. The diazo groups are evenly distributed along the polymer chain. This polymer is not a dispersant and cannot be used as a dispersant.
In US-A-3,168,401 light sensitive diazo sulphonate of cyclic amines are described for use in printing plates. US-A-3,168,401 does not describe a dispersing agent comprising a hydrophobic part and a hydrophilic part.
In US-A-4,299,907 very specific, light sensitive, high molecular weight diazo polymers are described for use in lithographic printing plates. The diazo groups are evenl distributed along the polymer chain. The polymers are not dispersing agents and do not comprise a hydrophobic part an a hydrophilic part.
In US-A-3,849,392 co-condensates of a diazo compound and second compound are described, that can be use in the preparation of printing plates and the like. The condensate comprises the diazo compound and the second compound evenly distributed along the chain, and therefore does not form a dispersion agent with a hydrophobic and a hydrophilic part.
In EP-A-339,393 aryl diazo sulphonates are described that are polymerizable and can decompose under light exposure, thereby modifying their solubility. The diazo groups are randomly divided over the polymer chain and therefore the polymer does not form a dispersion agent.
Preferably, the dispersing agents used are compounds according to formula (I) :
Figure imgf000006_0001
where R1 = H, OR2, Cl, Br or I where R2 = (C^-Cg )-alkyl X = -S03 or -P03 , M = an alkali metal, alkaline earth metal, quaternary ammonium ion or H, P = polymer, oligomer or a fatty acid derivative q = 1 or 2.
According to a further preferred embodiment of the invention:
R1 = H or OR2 where R2 = CH3 X = -S03 M = Na P = polyvinyl ether, polytetrahydrofuran, polyester or fatty acid derivative q = 1. The invention is further directed to a process for dispersing resin in an aqueous medium, whereby an ionic dispersing agent as described hereabove is used. This is particularly advantageous in a continuous process.
The dispersing agent is used in aqueous dispersion such as, for example, alkyl dispersions, aerylate dispersions and polyurethane dispersions. The dispersing agent according to the invention ca be added during or before the preparation of the dispersion When preparing acrylate dispersions, via emulsion polymerisation, the dispersing agent can, for example, be added during emulsification of the monomers. The preparatio of the known dispersions via emulsion polymerisation can be carried out in the presence of the catalysts and chain- regulating agents customary for this reaction.
The dispersing agent according to the invention ca be added in amounts of between 0.01 and 10% by weight (with respect to the amount of dispersion) . Preferably, this amount is between 0.1 and 5% by weight.
The dispersing agent according to the invention ca also be combined with the known emulsifiers.
The aqueous dispersions can contain conventional co-solvents in amounts of up to, for example, 30% by weight with respect to the amount of water.
The dispersions obtained can be used in coating compositions and adhesive compositions.
The invention will be illustated by the following examples, without being limited thereto.
Example I
Synthesis of 4-phenyldiazosulphonate-sodium salt
0.1 mol 4-aminophenol was dissolved in 135 ml 6% hydrochloric acid and cooled to -5°C. Then 0.1 mol of NaN02 dissolved in 50 ml of ice-cooled water, was added dropwise to this solution. After the addition was completed, the solution was stirred for 30 min at room temperature. Then the diazonium salt solution was added to an ice-cooled solution of 0.2 mol of sodium sulphite in 150 ml water. At 0°C a yellow precipitate was formed and filtered off.
Example II
Synthesis of 4-phenoldiazosulphonate-tetrabutylammonium salt
0.1 mol of 4-phenoldiazosulphonate-sodium salt obtained in example I was dissolved in water and 0.1 mol tetrabutylammoniumbromide was added. A yellow precipitate was formed and filtered off.
Example III
Coupling of a living poly inylether with a diazosulphonate Under nitrogen, 0.1 mol ethylvin lether was dissolved in 50 ml dry CH2C12 and cooled to -40°C. 10 ml 1 N HC1 in ether was slowly added to form the initiator. Then 0.1 ml 1 N ZnCl2 in ether was added to start the living polymerization. After about 20 in the monomer was almost consumed and the reaction was terminated with a mixture of 0.1 mol 4-phenoldiazosulphonate-tetrabutylammonium salt according to example II and 0.02 mol triethylamine in CH2C12. After a few minutes the mixture was washed with water to remove the excess of diazonium salt. The dispersant was isolated by evaporation of the solvent. NMR analysis showed that the diazosulphonate was coupled to the polyvinylether via an acetal bond. The dispersant appeared to be very unstable since the next day the NMR showed no acetal anymore and the yellow solution had become black.
Example IV
Coupling of a fatty acid chloride with a diazosulphonate
Under nitrogen, 0.1 mol palmitoyl chloride was dissolved in 50 ml dry aceton. Then 0.1 mol 4-phenoldiazosulphonate-sodium salt obtained in example I and 0.1 mol triethylamine was added and the reaction mixture was stirred for one week at room temperature. The dispersant was isolated by evaporation of the solvent. Example V
Photolysis and thermolysis of the dispersant The photolysis of the dispersant was followed with
NMR. After 5 days of exposure to day light, a solution of the dispersant in CDC13 showed no diazosulphonate anymore and a precipitate was formed.
Also a stable emulsion of H20 and toluene made with this dispersant was exposed to light. After 1 night of irradiation in a suntester the emulsion was separated in th original H20 and toluene layer. Upon irradiation the ionic headgroup is released and the dispersing capacity of the dispersant had disappeared. Thermogravimetric analysis showed that the dispersant is thermally stable up to 160°C.

Claims

C L A I M S
1. Ionic dispersing agent which can be used in aqueous dispersions that comprises a hydrophobic part and a hydrophilic part, characterised in that the hydrophobic part is a tail which can be a fatty acid derivative, a polymer or an oligomer and the hydrophilic part comprises a terminal diazo group with at least one acid derivative group coupled thereto.
2. Dispersing agent according to Claim 1, characterised in that the dispersing agent is based on a fatty acid derivate, an oligomer or a polymer having a molecular weight (Mn ) of between 100 and 5000.
3. Dispersing agent according to either of Claims 1 and 2 , characterised in that the dispersing agent is a compound according to formula (I)
P
Figure imgf000010_0001
N=N-XM_
where R1 = H, OR2 , Cl, Br or I where R2 = (C1-C6 )-alkyl, X = -S03 or -P03 ,
M = an alkali metal, alkaline earth metal, quaternary ammonium ion or H,
P = fatty acid derivative, polymer or oligomer and q = 1 or 2.
4. Dispersing agent according to Claim 3, characterised in that:
R1 = H or OR2 where R2 » CH3 X = -S03 M = Na P = polyvinyl ether, polytetrahydrofuran, polyester or fatty acid derivative q = 1.
5. Dispersion obtained using a dispersing agent according to one of Claims 1-4.
6. Coating or adhesive composition based on a dispersion according to Claim 5.
7. Process for dispersin resin in an aqueous medium, characterized in that an ionic dispersing agent according to any one of claims 1-4 is used.
8. Ionic dispersing agent, dispersion and coating as essentially described in the disclosure and/or the examples.
PCT/NL1993/000028 1992-02-03 1993-01-28 Ionic dispersing agent which can be used in aqueous dispersions WO1993014864A1 (en)

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NL9200186A NL9200186A (en) 1992-02-03 1992-02-03 IONOGENIC DISPENSER APPLICABLE IN AQUEOUS DISPERSIONS.
NL9200186 1992-02-03

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000031590A1 (en) * 1998-11-21 2000-06-02 Basf Aktiengesellschaft Aqueous dispersions with ionic dispersants
CN106565532A (en) * 2016-11-01 2017-04-19 帕潘纳(北京)科技有限公司 Synthetic method of substituted phenyl diazene compound and application of synthetic method
CN106831481A (en) * 2016-11-01 2017-06-13 帕潘纳(北京)科技有限公司 A kind of synthetic method of substituted phenylhydrazines and its salt
KR20200050000A (en) * 2018-10-30 2020-05-11 삼성디스플레이 주식회사 Light emitting element dispersant, Light emitting element ink comprising the same and method of manufacturing display device

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3168401A (en) * 1954-06-18 1965-02-02 Azoplate Corp Light sensitive diazo sulfonate material and preparation of printing plates therewith
US3174860A (en) * 1959-02-26 1965-03-23 Azoplate Corp Light sensitive polymeric diazonium and azidoacrylamido reproduction material and process of making plates therewith
US3373021A (en) * 1964-01-29 1968-03-12 Harris Intertype Corp Presensitized positive working lithographic plate
US3849392A (en) * 1969-05-20 1974-11-19 Kalle Ag Process for the production of polycondensation products of aromatic diazonium compounds
US4299907A (en) * 1978-08-10 1981-11-10 Polychrome Corporation Storage stable photosensitive diazo lithographic printing plates
EP0233072A2 (en) * 1986-02-12 1987-08-19 E.I. du Pont de Nemours and Company Improvements in or relating to radiation sensitive material
EP0330406A2 (en) * 1988-02-22 1989-08-30 Japan Synthetic Rubber Co., Ltd. Radiation-sensitive resin composition
EP0371640A1 (en) * 1988-11-11 1990-06-06 Nippon Paint Co., Ltd. A compound containing an oxamic acid group, a process for producing the compound, and a resin composition containing the compound

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3168401A (en) * 1954-06-18 1965-02-02 Azoplate Corp Light sensitive diazo sulfonate material and preparation of printing plates therewith
US3174860A (en) * 1959-02-26 1965-03-23 Azoplate Corp Light sensitive polymeric diazonium and azidoacrylamido reproduction material and process of making plates therewith
US3373021A (en) * 1964-01-29 1968-03-12 Harris Intertype Corp Presensitized positive working lithographic plate
US3849392A (en) * 1969-05-20 1974-11-19 Kalle Ag Process for the production of polycondensation products of aromatic diazonium compounds
US4299907A (en) * 1978-08-10 1981-11-10 Polychrome Corporation Storage stable photosensitive diazo lithographic printing plates
EP0233072A2 (en) * 1986-02-12 1987-08-19 E.I. du Pont de Nemours and Company Improvements in or relating to radiation sensitive material
EP0330406A2 (en) * 1988-02-22 1989-08-30 Japan Synthetic Rubber Co., Ltd. Radiation-sensitive resin composition
EP0371640A1 (en) * 1988-11-11 1990-06-06 Nippon Paint Co., Ltd. A compound containing an oxamic acid group, a process for producing the compound, and a resin composition containing the compound

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000031590A1 (en) * 1998-11-21 2000-06-02 Basf Aktiengesellschaft Aqueous dispersions with ionic dispersants
CN106565532A (en) * 2016-11-01 2017-04-19 帕潘纳(北京)科技有限公司 Synthetic method of substituted phenyl diazene compound and application of synthetic method
CN106831481A (en) * 2016-11-01 2017-06-13 帕潘纳(北京)科技有限公司 A kind of synthetic method of substituted phenylhydrazines and its salt
CN106831481B (en) * 2016-11-01 2018-05-25 帕潘纳(北京)科技有限公司 A kind of synthetic method of substituted phenylhydrazines and its salt
KR20200050000A (en) * 2018-10-30 2020-05-11 삼성디스플레이 주식회사 Light emitting element dispersant, Light emitting element ink comprising the same and method of manufacturing display device
CN112997325A (en) * 2018-10-30 2021-06-18 三星显示有限公司 Light-emitting element dispersant, light-emitting element ink including the same, and method for manufacturing display device
EP3876293A4 (en) * 2018-10-30 2022-11-09 Samsung Display Co., Ltd. Light-emitting element dispersing agent, light-emitting element ink comprising same, and method for producing display device
CN112997325B (en) * 2018-10-30 2024-05-07 三星显示有限公司 Light emitting element dispersant, light emitting element ink including the same, and method for manufacturing display device
KR102666905B1 (en) * 2018-10-30 2024-05-17 삼성디스플레이 주식회사 Light emitting element dispersant, Light emitting element ink comprising the same and method of manufacturing display device

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