WO1983000696A1 - Electron beam-curable resin - Google Patents
Electron beam-curable resin Download PDFInfo
- Publication number
- WO1983000696A1 WO1983000696A1 PCT/JP1982/000324 JP8200324W WO8300696A1 WO 1983000696 A1 WO1983000696 A1 WO 1983000696A1 JP 8200324 W JP8200324 W JP 8200324W WO 8300696 A1 WO8300696 A1 WO 8300696A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- resin
- electron beam
- double bond
- molecule
- acid
- Prior art date
Links
Classifications
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B5/00—Recording by magnetisation or demagnetisation of a record carrier; Reproducing by magnetic means; Record carriers therefor
- G11B5/62—Record carriers characterised by the selection of the material
- G11B5/68—Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent
- G11B5/70—Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent on a base layer
- G11B5/702—Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent on a base layer characterised by the bonding agent
- G11B5/7021—Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent on a base layer characterised by the bonding agent containing a polyurethane or a polyisocyanate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/46—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen
- C08G18/4676—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/90—Magnetic feature
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/92—Polyurethane having terminal ethylenic unsaturation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/25—Web or sheet containing structurally defined element or component and including a second component containing structurally defined particles
- Y10T428/256—Heavy metal or aluminum or compound thereof
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31609—Particulate metal or metal compound-containing
Definitions
- the present invention relates to an electron beam curable resin.
- the dispersibility of the magnetic paint is also high.
- the abrasion resistance of the obtained coating film was good, but the solvent resistance was still insufficient.
- the present invention has "" the properties of conventional polyester polyurethane resins, particularly when used as a binder of a magnetic paint for producing a magnetic recording medium such as a magnetic tape.
- the coating film has excellent solvent resistance, abrasion resistance, and mechanical strength. It is intended to provide a curable resin.
- the electron beam-curable resin according to the present invention is an oligopolyester urethane resin in which urethane bonds are present at both ends of a polyester molecular part, or Polyester polyurethane resin in which the molecular chain of the polyester is extended through a urethane bond, wherein the molecular weight of the resin is about 1,000 to 5,000. There is a double bond at each end of the resin molecule, and the carboxylic acid component having a metal sulfonate group in the molecule of the resin is fully capable of reacting with the sulfonic acid component. .0.2 to 30 moles.
- the above-mentioned polyol polyester urethane resin has a molecular weight of about 1,000 to 10,000, and that the above-mentioned polyester poly urethane resin is used.
- the tan resin preferably has a molecular weight of about 10,000 to 50,000 o
- Examples of the carboxylic acid component of the polyester resin used in the present invention include terephthalic acid, isoftanoleic acid, orthophthalic acid, and 1,5-naphthalic acid.
- Aromatic dicarboxylic acids such as carboxylic acid, succinic acid, adipic acid, azelic acid, cenosic acid, and aliphatic diacids such as dodecane carboxylic acid
- Dicarboxylic acids such as sulfonic acid, P-oxybenzoic acid, aromatic carboxylic acids such as P- (2-hydroxyoxy) benzoic acid, trimeric Tritonic acid, tetramelic acid, pyromellitic acid, and the like, and tricarboxylic acid and tetracarboxylic acid.
- Particularly preferred carbons include terephthalanolic acid, isophthalic acid, and ⁇ -phthalic acid.
- OMPI examples thereof include dipic acid and sebacic acid.
- Examples of the polyvalent alcohol component which is another component of the polyester resin used in the present invention include ethylene glycol and fuco alcohol.
- ⁇ ⁇ ⁇ ⁇ 1 1 1, 3- ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ Aliphatic dioles such as 2,2,4-trimethyl-1,5, pentandiol or substituted derivatives thereof, 1,4-cyclohexane Alicyclic polyols such as dimethanol, polyethylene glycols, dipropylene glycols, polyethylene glycols , Polypropylene glycol, Polyethylene glycol, Polyethylene glycol, etc.
- Oxysides such as alkylene-added adducts of aromatic dials such as propylene-added adducts can be listed. You. In addition, a trio such as Trimethylolorethane, Trimethylolonepropane, Glycerin, Pentaerytritolone, etc. Polyhydric alcohols such as tetraol can also be used, but it is preferable to use these polyhydric alcohols in combination with Geol.
- the dicarboxylic acid having a metal sulfonate base as another component of the copolymerized polyester resin used in the present invention, 2-natrium snorehotelev Tanoleic acid, 2-Cali Sulfones, such as muslim hotelterphthalic acid, 5-sodium muslimosulphoisophthalic acid, 5-calibursulphoisozophthalic acid
- a preferable example is an aromatic dicarboxylic acid containing a metal base.
- the metal sulfonate base it is preferable to use an alkali metal base. Good.
- the content of the sulfonate component containing these sulfonate-metal bases is about 10% of the total strength of the sulfonate component.
- the oligopolyester urethane according to the present invention is obtained by dissolving at least the hydroxyl groups at both ends of the copolymerized polyester resin as described above. It can be obtained by bonding to an isocyanate group of a net compound. Polyester polyurethane can be obtained by further extending the chain of this copolymerized polyester resin with an iso- cyanate compound. Examples of diisocyanate conjugates used include aliphatic diethylene thiocyanate and aliphatic diethylene thiocyanate.
- an acrylic or methacrylic monomer having a hydroxyl group at the molecular terminal and having a double bond is used.
- Such monomers include:
- the ren group is a linear or branched divalent saturated hydrocarbon residue having 1 to 12 carbon atoms.
- the alkylene group may also include a halogen atom, an alkyloxy group having 1 to 4 carbon atoms which may be substituted by 1 to 3 nitrogen atoms, a carbon atom power s 2 It may be substituted by a substituent such as a C 4 -C 4 alkyl group or a C 2 -C 4 alkenylcarbonylcarbonyl group.
- Preferred examples of the compounds represented by the above-mentioned general formula include 2-hydroxyhydrin acetic acid and methacrylic acid. Roxif. Mouth Pinole Estenolle, 2-Hydroxybutyl Ester, 2-Hydroxyoctyl Ester, 2-Hydroxy Dodecinol Este Nore, 2-H Dro xy-3-Kro lopro pinore ester, 2-Hdro xy-3- ⁇ ⁇ ⁇ ⁇ ⁇ -2 Metal crys- talette, 21-hydroxyl-5-acetoxyl pinol estenol, 2-hydroxyl-S-black B Complete set shift.
- Mouth Pisole Estenore 2-Hydroxy-5-Dichloro Acetoxy Pro Pimere Estenore, .2-Hydroxy Exit-3, Tri-Chloro Ase Tokishif. Mouth Pisole Estere, 2-Hydroxy-3-Crotonin eclectic Pro, Pinolester, 2-Hydroxy-3-Ali Loxy And the like.
- the oligopolyester urethane or polyesterpolyurethane isocitnate group Any monomer having an active hydrogen that reacts with and having an acryl-based or methacrylic double bond can be used in the present invention.
- the electron beam curable resin according to the present invention can be produced according to a conventional method.
- lipopolyester urethane resin for example, firstly, the above-mentioned carboxylic acid containing a carboxylic acid and a metal base of sulfonic acid and a polyvalent alcohol are used.
- a copolymerized polyester resin is produced according to a conventional method so as to have an appropriate molecular weight by using a resin. This is reacted with a diisocyanate compound to bind at least the hydroxyl groups at both ends of the copolymerized polyester resin to the isocyanate group.
- oligo-polyester urethane resin can be produced by introducing a methacrylic double bond.
- a copolymerized polyester resin is first produced.
- a diisocyanate compound is reacted with the copolymerized polyester resin, and the copolymerized resin is adjusted to have an appropriate molecular weight via a urethane bond. Chain extend the resin.
- by reacting the above-mentioned acryl-based or methacryl-based monomer it is possible to obtain the polyesterpolyurethane resin of the present invention. Yes o
- the thus prepared electronic thermosetting resin according to the present invention can be used as a binder of a magnetic paint for producing a magnetic recording medium such as a magnetic tape. Since this resin has a very hydrophilic metal sulfonate group in the molecule, a hydrophilic group is present especially on the surface used for the magnetic layer formed by coating on a non-magnetic support. inorganic powder that, for example, r - when used as binders for magnetic ⁇ Ko such Fe 2 0 s, and has a good dispersibility. Therefore, since the magnetic layer obtained by using such a resin as a binder and irradiating with an electron beam to cure it has excellent surface properties, a magnetic recording medium having excellent surface properties can be obtained. It will be.
- the resin according to the present invention has an acryl or metaacryl double bond which can be cleaved by electron beam irradiation to form a crosslinked structure at both ends.
- a crosslinked structure is formed between or within the molecules by electron beam irradiation to form a network structure, and the obtained magnetic layer has abrasion resistance and good durability.
- the electron beam-curable resin according to the present invention has a double bond at both ends of the molecule forming a crosslinked structure by irradiation with an electron beam, so that the coating film has excellent mechanical strength.
- a magnetic recording medium having good solvent resistance can be obtained.
- any element constituting the magnetic recording medium can be used as long as it is a usual one.
- a magnetic powder that can be used r - Fe 2 0 5, ⁇ 3 0 4, r - Fe 2 Os and Fe 3 0 4 iron oxide intermediate oxidation state, Co-containing organic?
- the iron oxide is et to one or more metal elements (especially those obtained by incorporating a transition metal element :), those having a coating layer mainly composed of Co oxide or hydroxide to the oxidation of iron, 'Cr0 2, Cr0 Cr 2 0 the surface reduction treatment of 2 Oxide-based magnetic powders such as those having five layers or metals such as Fe, Co, Ni, etc., or Fe-Co alloys, Fe-Ni alloys, Fe-Co-Ni alloys, Co-Ni-P alloys, Ferromagnetic powder such as Co-Ni-Fe-B alloy, Fe-Ni-Zn alloy, Fe-Mn-Zn alloy; and alloys such as Pe-Co-Ni-P alloy.
- metal elements especially those obtained by incorporating a transition metal element :
- the magnetic paint comprising the electron beam-curable resin and the magnetic powder according to the present invention is used as an antistatic agent such as aluminum oxide, chromium oxide, and silicon oxide as abrasives.
- Carbon As a lubricant such as black, disulfide molybdenum, graphite, silicone oil, olive oil, etc. can be added.
- a binder conventionally used as a binder for a magnetic recording medium may be used in combination, and examples of such a binder include vinyl chloride and vinyl chloride.
- Solvents that can be used in preparing the magnetic paint include, for example, acetate, methylethylketone, methylisobutylketone, cyclohexanone, and the like. Ketones; alcohols such as methanol; esters such as methyl sulphate, ethyl sulphate, butyl sulphate, and ethyl butyrate; ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ And aromatic hydrocarbons such as toluene, xylene and the like; aliphatic hydrocarbons such as hexane and heptane, and mixtures thereof.
- non-magnetic support materials that can be used include, for example, polystyrene such as polyethylene terephthalate, and polyporene such as polypropylene.
- Cellulose derivatives such as refine, cellulosic acetate, phenolic cellulose acetate, polycarbonate, polyvinyl chloride , Polyimide, Metals such as copper and non-magnetic materials such as paper ⁇
- a magnetic paint having the above-mentioned structure on a non-magnetic support by a conventional method and to dry it, and then subject the paint film to a calendar treatment and then irradiating it with an electron beam. After the irradiation, a calendar process can also be performed.
- the electron beams to be irradiated include neutron beams,? "Ionizing radiation such as radiation can be conveniently used, and industrially, electron beams are desirable. ⁇ 10 Mrad is preferred, and about 2-7 Mrad is more preferred. When an electron beam accelerator is used for irradiation, the irradiation energy (acceleration voltage) should be about 10 G KeV ⁇ .
- Example 1 Poly and gopolyester urethane resins containing double bonds and metal sulfonate bases
- Comparative Example 1 contains double bond but contains metal sulfonate base A3) Dimethyl terephthalate resin in a reaction vessel equipped with thermometer, stirrer and partial reflux condenser. 2 parts, dimethinolate isophthalate 119, 2 parts, ethylene glycol 1,48.2 parts, natural alcohol glycol 204, 5.4 parts and catalyst Then, 0.025 parts of zinc acetate and 0.0005 parts of sodium acetate were charged, and an ester exchange reaction was performed at 180 C to 220 for 3 hours. Next, 570.2 parts of sebacic acid was added, and a copolymerized polyester resin was synthesized in the same manner as in Example 1.
- the 0H group concentration of the copolymerized polyester resin obtained in this manner was 4 milliliters.
- the ratio of the carboxylic acid component of this resin is 20 moles of dimethyl terephthalate, 20 moles of dimethyl isopropylate, and ⁇ ⁇ ⁇ 0 moles of cynosuccinate.
- the copolymer resin obtained in Example 1 which did not undergo a double bond introduction reaction was used.
- concentration of 0 group in this resin was 42 millimoles ⁇ .
- the ratio of the carboxylic acid component of this resin is as follows: dimethyl 20 terephthalate ⁇ , 15 mol of dimethyl isopropyl isophthalate, and 5-sodium sulfoisophtalate. 5 mol of stream and 0 mol of senocin, and its glycol components, ethylene glycol and neopentyl glycol. the ratio between Lumpur were, respectively, 5 0 molar ⁇ 0
- the copolymerized polyester resin obtained in Comparative Example 1 was used without performing the reaction of introducing a double bond.
- the ratio of the carbon component of this resin is 20 moles of dimethyl terephthalate, 20 moles of dimethyl alcohol isoftanoleate and about 0 moles of sebacic acid.
- the ratio of the glycol components, ethylene glycol and neopentyl glycol, was 50 mol, respectively.
- the composition was as follows as a result of analyzing this copolymerized polyester resin by nuclear magnetic resonance (NMR) analysis and the like.
- Polyester polyurethane resin having a ratio of 1: 1, 30C) was obtained.
- Comparative Example 4 Polyester Polyurethane Resin Containing a Double Bond but Not a Metal Sulfonate Base-Anti-thermometer, Stirrer and Partial Reflux Cooler
- 19.2 parts of terephthalodimethyl, 119,2 parts of dimethinole isophthalate, 18.2 parts of ethylene glycol, and Neo 0.24 parts of pentyl glycol and 0.025 parts of zinc acetate and 0.05 parts of sodium nitrate as catalysts were charged.
- the ester exchange reaction was carried out at 2220 ° C. for 5 hours.
- 0.27 parts of sebacic acid S was added, and a copolymer polyester resin was synthesized in the same manner as in Example 2.
- the 0 H group concentration of the copolymerized polyester resin thus obtained was 4 millimoles Z ⁇ .
- the ratio of the carbonyl component of this resin is 20 moles of dimethyl ethanol terephthalate, 20 moles of dimethyl ethyl isophthalate and cenosuccinic acid.
- Each of the resins of Examples 1 and 2 and Comparative Example 1 and 4 was dried at 90 and 25 mm3 ⁇ 4f for 5 days to form a film of about 100 ⁇ , and then irradiated with 5 Mrad of electron beam at an acceleration voltage of 20 GKeV. A cured film was used. From this hardened film, a sliver having a width of 0.025 cm and a length of 1 ⁇ was cut out and measured with a universal pulling tester. The resin of Comparative Example 2 was measured in the same manner without irradiation with an electron beam. Table 2 shows the results. '
- Example 2 Using the resins of Example 2 and Comparative Examples 2, 5 and 4, the films of these resins vacuum-dried at 0 ° C. were cut into 1 cm squares, and methyl ethyl ketone, toluene and During cyclohexanone
- Example 2 and Comparative Example 4 were cured by irradiation with 200 KeV electron beam, and the resins of Comparative Examples 2 and 5 were not irradiated with electron beam. Table 3 shows the results.
- the tensile properties differed depending on the presence or absence of the metal sulfonate when irradiated with an electron beam. It is recognized that the tensile properties are significantly improved as compared with the resin.
- magnetic tapes were produced as follows.
- the magnetizable layer was formed on the polyethylene film by the same method using the respective resins of Example 2 and Comparative Examples 1, 2, 5, and 4. Was formed. .
- the magnetic layer was rubbed with gauze containing methyl ethyl ketone, and the number of rubs until the layer disappeared was expressed.
- Table 4 shows the test results for each tape.
- Examples 1 and 2 which contain a metal sulfonate and were cured by an electron beam, were also much different from Comparative Example 5 in Rs, Young's modulus ⁇ , solvent resistance, and powder dropout. It exceeds. Further, in comparison with Comparative Examples 1 and 4, no significant change was observed in the dispersibility and the orientation, but a considerable difference was observed in the powder fall.
- Comparative Example 2 is far inferior in durability in comparison with Examples 1 and 2 cured by an electron beam. The same tendency applies to Comparative Examples 1, 5 and 4. Industrial applicability
- the oligo-polyester urethane resin or the poly-ester poly urethane which is the electron beam-curable resin containing the metal sulfonate base according to the present invention.
- the resin has excellent dispersibility, tensile properties, and solvent resistance, and contains metal sulfonate base, and is superior to polyester resin which does not cause cross-linking reaction by electron beam.
- the magnetic tape is particularly excellent in solvent resistance and durability.
- the radiation curable resin can be applied to magnetic recording media, it can also be used in any field as a binder to form a coating film that requires properties such as solvent resistance and mechanical strength. Can be.
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19823248985 DE3248985T1 (de) | 1981-08-19 | 1982-08-19 | Durch elektronenstrahlung haertbares harz |
NL8220284A NL8220284A (nl) | 1981-08-19 | 1982-08-19 | Door elektronenstraling hardbare hars. |
GB8310314A GB2114587B (en) | 1981-08-19 | 1982-08-19 | Electron beam-curable resin |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP56/129741 | 1981-08-19 | ||
JP56129741A JPS5832617A (ja) | 1981-08-19 | 1981-08-19 | 電子線硬化性樹脂 |
JP56/129742810819 | 1981-08-19 | ||
JP56129742A JPS5832618A (ja) | 1981-08-19 | 1981-08-19 | 電子線硬化性樹脂 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1983000696A1 true WO1983000696A1 (en) | 1983-03-03 |
Family
ID=26465033
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP1982/000324 WO1983000696A1 (en) | 1981-08-19 | 1982-08-19 | Electron beam-curable resin |
Country Status (5)
Country | Link |
---|---|
US (1) | US4503198A (ja) |
EP (1) | EP0085722A4 (ja) |
GB (1) | GB2114587B (ja) |
NL (1) | NL8220284A (ja) |
WO (1) | WO1983000696A1 (ja) |
Families Citing this family (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5864627A (ja) * | 1981-10-15 | 1983-04-18 | Sony Corp | 磁気記録媒体 |
US4634633A (en) * | 1983-12-15 | 1987-01-06 | Sony Corporation | Magnetic recording medium |
US4558149A (en) * | 1983-12-16 | 1985-12-10 | Minnesota Mining And Manufacturing Company | Sulfonate-containing photopolymer systems |
US4746717A (en) * | 1983-12-16 | 1988-05-24 | Minnesota Mining And Manufacturing Company | Isocyanate-terminated sulfocompounds |
CA1238446A (en) * | 1984-08-09 | 1988-06-21 | Union Carbide Corporation | Flexible, self-crosslinking binders |
EP0189987B1 (en) * | 1985-01-25 | 1992-04-29 | Imperial Chemical Industries Plc | Polymerisable urethane compositions |
US4673705A (en) * | 1985-04-05 | 1987-06-16 | Desoto, Inc. | Radiation-curable coatings containing reactive pigment dispersants |
US4666784A (en) * | 1985-07-26 | 1987-05-19 | Toyo Boseki Kabushiki Kaisha | Magnetic recording medium |
US4638017A (en) * | 1985-12-09 | 1987-01-20 | Minnesota Mining And Manufacturing Company | Hydrophilic polyurethane/polyurea sponge |
US4738992A (en) * | 1985-12-09 | 1988-04-19 | Minnesota Mining And Manufacturing Company | Hydrophilic polyurethane/polyurea sponge |
NL8600421A (nl) * | 1986-02-20 | 1987-09-16 | Pd Magnetics Bv | Magnetisch registratie-element. |
JPS63108020A (ja) * | 1986-06-12 | 1988-05-12 | Toyobo Co Ltd | 放射線硬化型樹脂 |
US4855384A (en) * | 1987-01-22 | 1989-08-08 | Minnesota Mining And Manufacturing Company | Sulfonate-containing photopolymer systems |
US5017664A (en) * | 1987-06-03 | 1991-05-21 | Wisconsin Alumni Research Foundation | Biocompatible polyurethane devices wherein polyurethane is modified with lower alkyl sulfonate and lower alkyl carboxylate |
US4880883A (en) * | 1987-06-03 | 1989-11-14 | Wisconsin Alumni Research Foundation | Biocompatible polyurethanes modified with lower alkyl sulfonate and lower alkyl carboxylate |
DE69030981T2 (de) * | 1989-03-30 | 1997-10-23 | Toyo Boseki | Strahlungshärtbares Harz und dieses enthaltende Zusammensetzung |
GB2235927B (en) * | 1989-09-14 | 1992-10-21 | Asahi Chemical Ind | A sulfonic acid group-containing polyurethane and a photosensitive resin composition containing the same |
JPH072827B2 (ja) * | 1989-12-28 | 1995-01-18 | 日本ペイント株式会社 | 高分子組成物、それを乳化剤として用いた水性分散体および水性塗料組成物 |
DE4203546A1 (de) * | 1992-02-07 | 1993-08-12 | Basf Ag | Strahlungshaertbare, waessrige polyurethandispersionen |
US5427835A (en) * | 1992-06-04 | 1995-06-27 | Minnesota Mining And Manufacturing Company | Sulfopolymer/vanadium oxide antistatic compositions |
US5203884A (en) * | 1992-06-04 | 1993-04-20 | Minnesota Mining And Manufacturing Company | Abrasive article having vanadium oxide incorporated therein |
US5637368A (en) * | 1992-06-04 | 1997-06-10 | Minnesota Mining And Manufacturing Company | Adhesive tape having antistatic properties |
US5498685A (en) * | 1993-04-27 | 1996-03-12 | Minnesota Mining And Manufacturing Company | Carboxylic-acid functional polyurethane polymers and their use in magnetic recording media |
US5371166A (en) * | 1993-12-22 | 1994-12-06 | The B. F. Goodrich Company | Polyurethane composition for use as a dispersing binder |
US5449525A (en) * | 1995-01-19 | 1995-09-12 | Minnesota Mining And Manufacturing Company | Method for coating a magnetic recording medium and apparatus |
US6488993B2 (en) | 1997-07-02 | 2002-12-03 | William V Madigan | Process for applying a coating to sheet metal |
CA2365144A1 (en) * | 1999-03-19 | 2000-09-28 | Nippon Kayaku Kabushiki Kaisha | Urethane oligomer, resin compositions thereof, and cured article thereof |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5077433A (ja) * | 1973-11-13 | 1975-06-24 | ||
JPS5538693A (en) * | 1978-09-13 | 1980-03-18 | Toyo Tire & Rubber Co Ltd | Magnetic recording medium |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3509234A (en) * | 1965-08-13 | 1970-04-28 | Ford Motor Co | Radiation curable paint binders containing vinyl monomers and a hydroxylated polymer reacted with a polyisocyanate and an hydroxyl alkyl acrylate |
US3677920A (en) * | 1968-07-06 | 1972-07-18 | Asahi Chemical Ind | Photopolymerizable diisocyanate modified unsaturated polyester containing acrylic monomers |
US3641199A (en) * | 1969-07-07 | 1972-02-08 | Rohm & Haas | Urethane elastomer with active hydrogen containing monoethylenical unsaturated monomer |
FR2290460A1 (fr) * | 1974-11-05 | 1976-06-04 | Rhone Poulenc Ind | Procede de fabrication de polyurethannes hydrosolubles |
US4073828A (en) * | 1976-04-12 | 1978-02-14 | Ici Americas Inc. | Ethylenically unsaturated monomer solutions containing urylated linear polyester/polyurethane resins |
US4072770A (en) * | 1976-05-11 | 1978-02-07 | Scm Corporation | U.V. curable poly(ester-urethane) polyacrylate polymers and wet look coatings therefrom |
US4112017A (en) * | 1976-07-23 | 1978-09-05 | Lord Corporation | Radiation curable coating compositions |
DE2936039A1 (de) * | 1979-09-06 | 1981-04-02 | Bayer Ag, 5090 Leverkusen | Wasserdispergierbare, durch strahlen vernetzbare bindemittel aus urethanacrylaten, ein verfahren zu ihrer herstellung sowie die verwendung dieser bindemittel in waessriger dispersion auf dem anstrich-, druckfarben- und textilsektor |
-
1982
- 1982-08-19 NL NL8220284A patent/NL8220284A/nl not_active Application Discontinuation
- 1982-08-19 WO PCT/JP1982/000324 patent/WO1983000696A1/ja not_active Application Discontinuation
- 1982-08-19 GB GB8310314A patent/GB2114587B/en not_active Expired
- 1982-08-19 EP EP19820902465 patent/EP0085722A4/en not_active Ceased
- 1982-08-19 US US06/492,023 patent/US4503198A/en not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5077433A (ja) * | 1973-11-13 | 1975-06-24 | ||
JPS5538693A (en) * | 1978-09-13 | 1980-03-18 | Toyo Tire & Rubber Co Ltd | Magnetic recording medium |
Also Published As
Publication number | Publication date |
---|---|
GB8310314D0 (en) | 1983-05-18 |
EP0085722A4 (en) | 1983-12-23 |
GB2114587B (en) | 1984-11-07 |
GB2114587A (en) | 1983-08-24 |
NL8220284A (nl) | 1983-07-01 |
US4503198A (en) | 1985-03-05 |
EP0085722A1 (en) | 1983-08-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO1983000696A1 (en) | Electron beam-curable resin | |
EP0249222B1 (en) | Radiation curable resin | |
JPS6346884B2 (ja) | ||
JP2006302471A (ja) | 磁気記録媒体 | |
JPH0326209B2 (ja) | ||
JPH0366728B2 (ja) | ||
JPH01159824A (ja) | 磁気記録媒体 | |
JPH055850B2 (ja) | ||
JPH045684B2 (ja) | ||
JPS5832618A (ja) | 電子線硬化性樹脂 | |
JPH055849B2 (ja) | ||
JP3873258B2 (ja) | 非ハロゲン化燐含有フェノキシ樹脂 | |
JP3873253B2 (ja) | 燐含有フェノキシ樹脂 | |
JP2008192239A (ja) | 磁気記録媒体 | |
JP3496353B2 (ja) | 磁気記録媒体 | |
JPH055851B2 (ja) | ||
JPS6065017A (ja) | 電子線硬化性樹脂 | |
JPS6065018A (ja) | ポリイソシアネ−ト化合物 | |
JPH0416852B2 (ja) | ||
JPS6065019A (ja) | ポリイソシアネ−ト化合物 | |
JPH048856B2 (ja) | ||
JPS5979427A (ja) | 磁気記録媒体 | |
JPS63105070A (ja) | 放射線硬化性塗料 | |
JPS63189416A (ja) | 放射線硬化性塗料 | |
JPS5835728A (ja) | 磁気記録媒体 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Designated state(s): DE GB NL US |
|
AL | Designated countries for regional patents |
Designated state(s): FR |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1982902465 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: 1982902465 Country of ref document: EP |
|
RET | De translation (de og part 6b) |
Ref document number: 3248985 Country of ref document: DE Date of ref document: 19831020 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 3248985 Country of ref document: DE |
|
WWR | Wipo information: refused in national office |
Ref document number: 1982902465 Country of ref document: EP |
|
WWW | Wipo information: withdrawn in national office |
Ref document number: 1982902465 Country of ref document: EP |