JPS62195720A - Magnetic recording medium - Google Patents
Magnetic recording mediumInfo
- Publication number
- JPS62195720A JPS62195720A JP3767686A JP3767686A JPS62195720A JP S62195720 A JPS62195720 A JP S62195720A JP 3767686 A JP3767686 A JP 3767686A JP 3767686 A JP3767686 A JP 3767686A JP S62195720 A JPS62195720 A JP S62195720A
- Authority
- JP
- Japan
- Prior art keywords
- group
- phosphorus
- formulas
- polyurethane resin
- magnetic
- 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.)
- Pending
Links
- 230000005291 magnetic effect Effects 0.000 title claims description 39
- 229920005749 polyurethane resin Polymers 0.000 claims abstract description 33
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 20
- 239000011230 binding agent Substances 0.000 claims abstract description 15
- 239000011574 phosphorus Substances 0.000 claims abstract description 14
- 125000004437 phosphorous atom Chemical group 0.000 claims abstract description 8
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 6
- 150000001340 alkali metals Chemical group 0.000 claims abstract description 6
- 125000003277 amino group Chemical group 0.000 claims abstract description 5
- 125000002993 cycloalkylene group Chemical group 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000000524 functional group Chemical group 0.000 claims abstract description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 2
- -1 phosphorus compound Chemical group 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 230000005294 ferromagnetic effect Effects 0.000 claims description 5
- 239000000696 magnetic material Substances 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 229920002635 polyurethane Polymers 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000006249 magnetic particle Substances 0.000 abstract description 15
- 150000002148 esters Chemical class 0.000 abstract description 2
- 150000002009 diols Chemical class 0.000 description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- 229920000728 polyester Polymers 0.000 description 15
- 229920005989 resin Polymers 0.000 description 13
- 239000011347 resin Substances 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 11
- 150000003018 phosphorus compounds Chemical class 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 239000003973 paint Substances 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000004970 Chain extender Substances 0.000 description 7
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 230000007423 decrease Effects 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 229920001225 polyester resin Polymers 0.000 description 6
- 239000004645 polyester resin Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 239000005056 polyisocyanate Substances 0.000 description 4
- 229920001228 polyisocyanate Polymers 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- RBNPOMFGQQGHHO-UHFFFAOYSA-N -2,3-Dihydroxypropanoic acid Natural products OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- RBNPOMFGQQGHHO-UWTATZPHSA-N D-glyceric acid Chemical compound OC[C@@H](O)C(O)=O RBNPOMFGQQGHHO-UWTATZPHSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 2
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 1
- KKTUQAYCCLMNOA-UHFFFAOYSA-N 2,3-diaminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1N KKTUQAYCCLMNOA-UHFFFAOYSA-N 0.000 description 1
- SLJZUKLGAWYGIF-UHFFFAOYSA-N 2,5-dihydroxybenzenesulfonic acid;sodium Chemical compound [Na].OC1=CC=C(O)C(S(O)(=O)=O)=C1 SLJZUKLGAWYGIF-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- BXGYBSJAZFGIPX-UHFFFAOYSA-N 2-pyridin-2-ylethanol Chemical compound OCCC1=CC=CC=N1 BXGYBSJAZFGIPX-UHFFFAOYSA-N 0.000 description 1
- YZTJKOLMWJNVFH-UHFFFAOYSA-N 2-sulfobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1S(O)(=O)=O YZTJKOLMWJNVFH-UHFFFAOYSA-N 0.000 description 1
- WMRCTEPOPAZMMN-UHFFFAOYSA-N 2-undecylpropanedioic acid Chemical compound CCCCCCCCCCCC(C(O)=O)C(O)=O WMRCTEPOPAZMMN-UHFFFAOYSA-N 0.000 description 1
- VTSFNCCQCOEPKF-UHFFFAOYSA-N 3-amino-1h-pyridin-2-one Chemical compound NC1=CC=CN=C1O VTSFNCCQCOEPKF-UHFFFAOYSA-N 0.000 description 1
- PECYZEOJVXMISF-UHFFFAOYSA-N 3-aminoalanine Chemical compound [NH3+]CC(N)C([O-])=O PECYZEOJVXMISF-UHFFFAOYSA-N 0.000 description 1
- QLIQIXIBZLTPGQ-UHFFFAOYSA-N 4-(2-hydroxyethoxy)benzoic acid Chemical compound OCCOC1=CC=C(C(O)=O)C=C1 QLIQIXIBZLTPGQ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 229920001747 Cellulose diacetate Polymers 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- XMUZQOKACOLCSS-UHFFFAOYSA-N [2-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=CC=C1CO XMUZQOKACOLCSS-UHFFFAOYSA-N 0.000 description 1
- ZHOWIUGOXBMVRA-UHFFFAOYSA-N [Na].C(C)C1=CC=CC2=CC=CC=C12 Chemical compound [Na].C(C)C1=CC=CC2=CC=CC=C12 ZHOWIUGOXBMVRA-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- UGZICOVULPINFH-UHFFFAOYSA-N acetic acid;butanoic acid Chemical compound CC(O)=O.CCCC(O)=O UGZICOVULPINFH-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000006247 magnetic powder Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- AJCDFVKYMIUXCR-UHFFFAOYSA-N oxobarium;oxo(oxoferriooxy)iron Chemical compound [Ba]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O AJCDFVKYMIUXCR-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- NMLSEBHVDVAYOL-UHFFFAOYSA-N propane-1,1-diol;pyridine Chemical compound CCC(O)O.C1=CC=NC=C1 NMLSEBHVDVAYOL-UHFFFAOYSA-N 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 1
- GGOZGYRTNQBSSA-UHFFFAOYSA-N pyridine-2,3-diol Chemical compound OC1=CC=CN=C1O GGOZGYRTNQBSSA-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- RTVVXRKGQRRXFJ-UHFFFAOYSA-N sodium;2-sulfobutanedioic acid Chemical compound [Na].OC(=O)CC(C(O)=O)S(O)(=O)=O RTVVXRKGQRRXFJ-UHFFFAOYSA-N 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は磁気特性および機械特性の優れた磁気記録媒体
に関するものである。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a magnetic recording medium with excellent magnetic and mechanical properties.
（従来の技術）
汎用的磁気テープは長軸１μｍ以下の針状磁性粒子を適
当な添加剤（分散剤、潤滑剤、帯電防止剤等）と共にバ
インダー溶液中に分散させて磁性塗料を作り、こｔ’ｔ
、ｔポリエチレンテレフタレートフィルムに塗布して作
られる。(Prior art) General-purpose magnetic tape is made by dispersing acicular magnetic particles with a long axis of 1 μm or less in a binder solution together with appropriate additives (dispersants, lubricants, antistatic agents, etc.) to create a magnetic coating. t't
, t made by coating on polyethylene terephthalate film.
磁性記録媒体では磁気記録の高密度化、高再生出力が要
求さｎ、そのためには高保磁力の磁性粒子を高充填、高
配向させることが必要である。高充填、高配向させるに
は、磁性粒子を一次粒子まで分散さ″せなければならな
い。磁性粒子の分散には、バインダーの影響が大きく、
いかに分散効率のよい分散機を用いてもバインダーの分
散能が低いと塗料中に磁性粒子は分散しない。また高保
磁力の磁性粒子が開発されているが、保磁力が大きくな
るにしたがって磁性粒子は分散しにくくなム従来、磁性
塗料のバインダーとしては、塩化ビニル・酢酸ビニル共
重合体、塩化ビニル・酢酸ビ脂、熱硬化ポリウレタン樹
脂、ポリエステル樹脂、アクリロニトリル・ブタジェン
共重合体、ニトロセルロース、セルロースφアセテート
・ブチレート、エポキシ樹脂あるいはアクリル樹脂等が
使用されている。一方、放射線硬化型バインダーとして
は、アクリル系二重結合を有する塩化ビニル・酢酸ビニ
ル共重合体、エポキシ樹脂、ポリエステル樹脂、ポリウ
レタン樹脂、アクリル樹脂等が提案されているが、ビデ
オテープ、電子計算機用テープのような高性能を要求さ
ｎる用途には、特に、磁気特性に２いて十分なものとは
いえないのが現状である。磁気特性の向上のために界面
活性剤を分散剤として使用することが知られているが、
磁性塗膜中に低分子量の界面活性剤が存在することによ
る物性の低下、経時変化を生じる欠点がある。Magnetic recording media are required to have high magnetic recording density and high reproduction output, and for this purpose, it is necessary to highly fill and highly align magnetic particles with high coercive force. To achieve high filling and high orientation, the magnetic particles must be dispersed down to the primary particles.The binder has a large influence on the dispersion of magnetic particles.
No matter how efficient a dispersion machine is used, if the binder has low dispersion ability, magnetic particles will not be dispersed in the paint. In addition, magnetic particles with high coercive force have been developed, but as the coercive force increases, magnetic particles become more difficult to disperse. Conventionally, binders for magnetic paints include vinyl chloride/vinyl acetate copolymer, vinyl chloride/acetic acid copolymer, Bicarbonate resin, thermosetting polyurethane resin, polyester resin, acrylonitrile-butadiene copolymer, nitrocellulose, cellulose φ acetate-butyrate, epoxy resin, acrylic resin, etc. are used. On the other hand, as radiation-curable binders, vinyl chloride/vinyl acetate copolymers with acrylic double bonds, epoxy resins, polyester resins, polyurethane resins, acrylic resins, etc. have been proposed; At present, the magnetic properties are not sufficient especially for applications requiring high performance such as tape. It is known that surfactants are used as dispersants to improve magnetic properties, but
The presence of a low molecular weight surfactant in the magnetic coating has the drawback of deterioration of physical properties and deterioration over time.
磁気テープは優れた磁気特性だけではなく、耐摩耗性、
走行性、可撓性、支持体との接着性等の機械的特性が優
れていなくてはならない。ポリエステル樹脂、ポリウレ
タン樹脂をバインダーとして使用した磁気テープは、特
公昭４４−１７９４７、特公昭４４−１８２２２、特公
昭４５−２４９００、特公昭４４−２８５００、特公昭
４５−２４９０２、特公昭４９−４８１２６、特公昭４
８−８１６１１、特公昭４８−８１６１０．特公昭４２
−１５４８２、特公昭５１−６５２２号公報にみられる
ように、機械的特性が優れ、磁気テープバインダーとし
て有用な素材である。Magnetic tape not only has excellent magnetic properties, but also wear resistance,
It must have excellent mechanical properties such as runnability, flexibility, and adhesion to the support. Magnetic tapes using polyester resins and polyurethane resins as binders are manufactured by Japanese Patent Publication No. 44-17947, Special Publication No. 18222-1970, Special Publication No. 45-24900, Special Publication No. 44-28500, Special Publication No. 45-24902, Special Publication No. 48126-1970, Tokuko Showa 4
8-81611, Special Publication No. 48-81610. Special Public Service (1977)
-15482, and Japanese Patent Publication No. 51-6522, it has excellent mechanical properties and is a useful material as a magnetic tape binder.
（発明が解決しようとする問題点）
ポリエステル樹脂、ポリウレタン樹脂にスルホン酸の金
属塩を導入することによシ磁性粒子の分散性が飛躍的に
向上することは特開昭５４−２８６０８、特開昭５４−
１５７６０８号公報に開示されているが、スルホン酸の
金属塩の効果は、その親水性によるものであり、ホスフ
ィン酸、ホスホン酸等の燐化合物の金属塩も同様な効果
が期待できる。しかしホスフィン酸、ホスホン酸等の燐
化合物の金属塩はポリエステル樹脂、ポリウレタン樹脂
などの製造時に触媒の失活現象が起きたシ、エーテル結
合が生成して得られるポリマーの物性が低下したシ、あ
るいは極性が異なるため均一に反応することなく分離し
てしまったりする。ポリウレタン樹脂などでもホスフィ
ン酸、ホスホン酸等の燐化合物の金属塩は無機性が大き
いため、汎用溶剤中あるいは無溶剤中の反応で、樹脂中
に、この親水基を導入することは不可能であった。(Problems to be Solved by the Invention) It has been reported in JP-A-54-28608 and JP-A-54-28608 that the dispersibility of magnetic particles is dramatically improved by introducing a metal salt of sulfonic acid into polyester resin or polyurethane resin. 1972-
As disclosed in Japanese Patent No. 157608, the effect of metal salts of sulfonic acid is due to its hydrophilicity, and similar effects can be expected from metal salts of phosphorus compounds such as phosphinic acid and phosphonic acid. However, metal salts of phosphorus compounds such as phosphinic acid and phosphonic acid may cause deactivation of the catalyst during the production of polyester resins, polyurethane resins, etc., or the physical properties of the resulting polymer may deteriorate due to the formation of ether bonds. Because they have different polarities, they may separate without reacting uniformly. Even in polyurethane resins, metal salts of phosphorus compounds such as phosphinic acid and phosphonic acid are highly inorganic, so it is impossible to introduce these hydrophilic groups into the resin by reaction in a general-purpose solvent or in the absence of a solvent. Ta.
（問題点を解決するための手段）
本発明者等は、以上のような事情に鑑み、硬化した塗膜
がポリウレタン樹脂の有する機械的特性を保持したまま
、磁性粒子の分散性を向上させることを目的として、鋭
意検討した結果、特定の燐化合物を用いれば、ポリウレ
タン樹脂の安定した製造が可能であジ、目的とする磁性
粒子の分散性の著しい向上が得られることを見出した。(Means for Solving the Problems) In view of the above circumstances, the present inventors have developed an object to improve the dispersibility of magnetic particles while the cured coating film retains the mechanical properties of the polyurethane resin. As a result of extensive research aimed at this purpose, it was discovered that by using a specific phosphorus compound, it is possible to stably produce a polyurethane resin, and the desired dispersibility of magnetic particles can be significantly improved.
すなわち本発明は非磁性支持体に、強磁性粉末を結合剤
中に分散させた磁性材料を塗布した磁気記録媒体におい
て、ポリウレタン樹脂形成性成分として下記式（Ｉ）〜
（％Ｑで示される燐化合物の少なくとも１種−−よび燐
以外の親水性極性基含有化合物を含有する分子量６０，
０００〜５０，０００の燐含有ポリウレタン樹脂を上記
結合剤の成分として使用することを特徴とする磁気記録
媒体である。That is, the present invention provides a magnetic recording medium in which a magnetic material in which ferromagnetic powder is dispersed in a binder is coated on a non-magnetic support, and the following formulas (I) to 1 are used as polyurethane resin forming components.
(Molecular weight 60 containing at least one phosphorus compound represented by %Q and a hydrophilic polar group-containing compound other than phosphorus,
The present invention is a magnetic recording medium characterized in that a phosphorus-containing polyurethane resin having a molecular weight of 000 to 50,000 is used as a component of the binder.
（ｘ、ｙはエステル形成性官能基、Ｒ３は炭素数８〜ｌ
Ｏの８価の炭化水素基、Ｒ２け炭素数１〜１２のアルキ
ル基、シクロアルキル基、アリール基、炭素数１〜１２
のアルコキシ基、シクロアルコキシ基、又はアリールオ
キシ基を示す。アリール基、およびアリールオキシ基は
ハロゲン原子、ヒト四キシ基、−０Ｍ’ （Ｍ’はアル
カリ金属を示す）、またはアミノ基が結合したものでも
良い。Ｒｓ ＊ Ｒ４Ｆｉ、炭素数ｌ〜１２のアルキレ
ン基、シクロアルキレン基、アリーレン基、次式： −
（ＣＨ，−０＆−）、ｐで表わされる基（Ｒ，Ｆｉ炭素
数１−１２のアルキレン基、シクロアルキレン基、アリ
ーレン基を示す。ｍ１４１〜４の任意の数値をとること
ができる。Ｍはアルカリ金属原子、水素、１価の炭化水
素基、又はアミノ基を示す。〕
本発明のポリウレタン樹脂は、分子！５００〜２０．０
００のポリエステルジオール（Ａ）、分子量５００未満
の鎖延長剤（Ｂ）とポリイソシアネート（Ｃ）と必要に
より末端停止剤ＣＤ） を反応させることによって得ら
れる分子量６，０００〜５０，０００のポリウレタン樹
脂である。(x, y are ester-forming functional groups, R3 has 8 to 1 carbon atoms
O octavalent hydrocarbon group, R2 alkyl group having 1 to 12 carbon atoms, cycloalkyl group, aryl group, 1 to 12 carbon atoms
represents an alkoxy group, cycloalkoxy group, or aryloxy group. The aryl group and aryloxy group may have a halogen atom, a human tetraxy group, -0M'(M' represents an alkali metal), or an amino group bonded thereto. Rs * R4Fi, alkylene group having 1 to 12 carbon atoms, cycloalkylene group, arylene group, following formula: -
(CH, -0&-), a group represented by p (R, Fi indicates an alkylene group, cycloalkylene group, or arylene group having 1 to 12 carbon atoms. m can take any numerical value from 1 to 4. M is It represents an alkali metal atom, hydrogen, a monovalent hydrocarbon group, or an amino group.] The polyurethane resin of the present invention has a molecular weight of !500 to 20.0.
00 polyester diol (A), a chain extender (B) with a molecular weight of less than 500, a polyisocyanate (C), and optionally a terminal stopper CD) A polyurethane resin with a molecular weight of 6,000 to 50,000 obtained by reacting It is.
本発明のポリウレタン樹脂はその形成性成分として上記
式（１）〜（ｖ）で示される燐化合物の少なくとも１種
２よび燐原子以外の親水性基を含有する化合物を含有す
る。具体的には上記（Ｉ）〜（ｖ）で示される燐化合物
はポリエステルジオール（Ａ）のカルボン酸成分または
アルコール成分として使用するか、又は鎖延長剤（Ｂ）
として使用する。また燐原子以外の親水性基を含有する
化合物は鎖延長剤（Ｂ）または末端停止剤（Ｄ）として
使用する。The polyurethane resin of the present invention contains at least one kind of phosphorus compounds represented by the above formulas (1) to (v) 2 and a compound containing a hydrophilic group other than a phosphorus atom as its forming component. Specifically, the phosphorus compounds shown in (I) to (v) above are used as the carboxylic acid component or alcohol component of the polyester diol (A), or as a chain extender (B).
Use as. Further, a compound containing a hydrophilic group other than a phosphorus atom is used as a chain extender (B) or a terminal stopper (D).
本発明に２いて使用されるポリエステルジオール（Ａ）
のカルボン酸成分としては、テレフタル酸、イソフタル
酸、オルソフタル酸、１．５−ナフタル酸などの芳香族
ジカルボン酸、Ｐ−オキシ安息香酸、ｐ−（ヒドロキシ
エトキシ）安息香酸などの芳香族オキシカルボン酸、コ
ノ１り酸、アジピン酸、アゼライン酸、セバシン酸、ド
デカンジカルボン酸などの脂肪族ジカルボン酸、フマー
ル酸、マレイン酸、イタコン酸、テトラヒドロフタル酸
、ヘキサヒドロフタル酸等の年始脂肪族２よび脂環族ジ
カルボン酸、トリメリット酸、トリメシン酸、ピロメリ
ット酸などのトリ２よびテトラカルボン酸などを挙げる
ことができる。Polyester diol (A) used in the present invention
The carboxylic acid components include aromatic dicarboxylic acids such as terephthalic acid, isophthalic acid, orthophthalic acid, and 1,5-naphthalic acid; aromatic oxycarboxylic acids such as p-oxybenzoic acid and p-(hydroxyethoxy)benzoic acid; , aliphatic dicarboxylic acids such as conolilic acid, adipic acid, azelaic acid, sebacic acid, and dodecanedicarboxylic acid; Examples include cyclic dicarboxylic acids, tri- and tetracarboxylic acids such as trimellitic acid, trimesic acid, and pyromellitic acid.
またポリエステルジオール（６）のグリコール成分とし
てはエチレングリコール、プロピレングリコール、１．
８−プロパンジオール、１．４−ブタンジオール、１．
５−ベンタンジオール、１．６−ヘキサンジオール、ネ
オペンチルグリコール、ジエチレングリコール、ジプロ
ピレングリコール、２．８．４−トリメチル−１，８−
ベンタンジオール、ｌ、４−シクロヘキサンジメタツー
ル、ビスフェノールＡのエチレンオキサイド付加物２よ
びプロピレンオキサイド付加物、水素化ビスフェノール
Ａのエチレンオキサイド２よびプロピレンオキサイド付
加物、ポリエチレングリコール、ポリプロピレングリコ
ール、ポリテトラメチレングリコールなどがある。また
トリメチロールエタン、トリメチロールプロパン、グリ
セリン、ペンタエリスリトールなどのトリおよびテトラ
オールを併用してもよい。In addition, the glycol components of the polyester diol (6) include ethylene glycol, propylene glycol, 1.
8-propanediol, 1.4-butanediol, 1.
5-bentanediol, 1,6-hexanediol, neopentyl glycol, diethylene glycol, dipropylene glycol, 2.8.4-trimethyl-1,8-
Bentanediol, l,4-cyclohexane dimetatool, ethylene oxide adduct 2 and propylene oxide adduct of bisphenol A, ethylene oxide 2 and propylene oxide adduct of hydrogenated bisphenol A, polyethylene glycol, polypropylene glycol, polytetramethylene glycol and so on. Further, tri- and tetraols such as trimethylolethane, trimethylolpropane, glycerin, and pentaerythritol may be used in combination.
ポリエステルジオールとしては他に６−カプロラクトン
等のラクトン類を開環重合して得られるラクトン系ポリ
エステルジオール類があげられる。Other examples of polyester diols include lactone-based polyester diols obtained by ring-opening polymerization of lactones such as 6-caprolactone.
本発明で使用されるポリイソシアネート０として＃ｉ２
．４−）リレンジイソシアネート、２．６トリレンジイ
ソシアネート、Ｐ−フ二二レンジイソシアネート、ジフ
ェニルメタンジイソシアネート、ｍ−フ二二レンジイソ
シアネート、ヘキサメチレンジイソシアネート、テトラ
メチレンジイソシアネート、８．８′−ジメトキシ−４
′１４−ビフェニレンジイソシアネー）、２．４−ナフ
タレンジイソシアネート、８′Ｉ８−ジメチル−４’、
４−ビフェニレンジイソシアネート、 ４ 、４’−ジ
フェニレンジイソシアネート、４ 、４’−ジイソシア
ネート−ジフェニルエーテル、１ 、５’−ナフタレン
ジインシアネート、Ｐ−キシリレンジイソシアネート、
ｍ−キシ１１レンジイソシアネート、１−８−ジイソシ
アネートメチルシクロヘキサン、１．４−ジイソシアネ
ートメチルシクロヘキサン、４ 、４’−ジイソシアネ
ートジシクロヘキサン、４．４’−ジインシアネートシ
クロヘキシルメタン、イソホロンジイソシアネート等の
シイツクアネート化合物、あるいけ全イソシアネート基
のうち７モルチ以下の２．４−トリレンジインシアネー
トの三量体、ヘキサメチレンジイソシアネートの三−を
体等のトリイソシアネート化合物があげられる。#i2 as polyisocyanate 0 used in the present invention
．． 4-) lylene diisocyanate, 2.6 tolylene diisocyanate, P-phenyl diisocyanate, diphenylmethane diisocyanate, m-phenyl diisocyanate, hexamethylene diisocyanate, tetramethylene diisocyanate, 8.8′-dimethoxy-4
'14-biphenylene diisocyanate), 2,4-naphthalene diisocyanate, 8'I8-dimethyl-4',
4-biphenylene diisocyanate, 4,4'-diphenylene diisocyanate, 4,4'-diisocyanate-diphenyl ether, 1,5'-naphthalene diisocyanate, P-xylylene diisocyanate,
m-xy 11-diisocyanate, 1-8-diisocyanatemethylcyclohexane, 1,4-diisocyanatemethylcyclohexane, 4,4'-diisocyanatedicyclohexane, 4,4'-diincyanatocyclohexylmethane, isophorone diisocyanate, etc. Examples include triisocyanate compounds such as a trimer of 2,4-tolylene diisocyanate and a 3-mer of hexamethylene diisocyanate having 7 moles or less of all isocyanate groups.
本発明で用いる分子！５００未満の鎖延長剤■）は、樹
脂中のウレタン基、あるいはウレア基濃度を調整しポリ
ウレタン樹脂に特有な強靭性上付与する効果があり、具
体的な化合物としては、エチレングリコール、１．８−
プロピレングリコール、１．４−テトラメチレングリコ
ール、１．６−ヘキサ／ジオール、シクロヘキサンジメ
タツール、キシリレングリコール、ジエチレングリコー
ル、トリエチレングリコール、ビスフェノールＡのエチ
レンオキサイド付加物等の直鎖グリコール、プロピレン
グリコール、ネオペンチルグリコール、１．２−ブタン
ジオール、１．８−ブタンジオール、２，２．４−）ジ
メチル−１，３−ベンタンジオール、ビスフェノールＡ
のプロピレンオキサイド付加物等の分岐グリコール、モ
ノエタノールアミン、Ｎ−メチルエタノールアミン等の
アミノアルコール、エチレンジアミン、ヘキサメチレン
ジアミン、インホロンジアミン、ピペラジン等のジアミ
ンあるいけ水等がおばらｎる。Molecules used in the present invention! The chain extender (<500) has the effect of adjusting the urethane group or urea group concentration in the resin and imparting toughness specific to polyurethane resin. Specific compounds include ethylene glycol, 1.8 −
Propylene glycol, 1,4-tetramethylene glycol, 1,6-hex/diol, cyclohexane dimetatool, xylylene glycol, diethylene glycol, triethylene glycol, linear glycols such as ethylene oxide adducts of bisphenol A, propylene glycol, Neopentyl glycol, 1.2-butanediol, 1.8-butanediol, 2,2.4-)dimethyl-1,3-bentanediol, bisphenol A
Branched glycols such as propylene oxide adducts, amino alcohols such as monoethanolamine and N-methylethanolamine, diamines such as ethylenediamine, hexamethylenediamine, inphorondiamine, piperazine, etc.
上記以外の鎖延長剤としては、トリメチロールプロパン
、ジェタノールアミン、トリエタノールアミン、グリセ
リン等三宮能成分を性能が損なわｎない範囲、ポリエス
テルジオール（５）と鎖延長剤の）の合計の５当ｉ％以
下で使用してもよい。Chain extenders other than those listed above may be used within the range that does not impair the performance of the Sannomiya component, such as trimethylolpropane, jetanolamine, triethanolamine, and glycerin, and the sum of 5 equivalents of the polyester diol (5) and the chain extender. It may be used at less than i%.
鎖延長剤の分子量が６００を越えるとポリウレタン樹脂
に特有な強靭性が低下するため好ましくない。If the molecular weight of the chain extender exceeds 600, it is not preferable because the toughness characteristic of polyurethane resins decreases.
本発明のポリウレタン樹脂の形成性成分の１つけ、前記
式（１）〜（ｖ）で示される燐化合物である。これらの
燐化合物の代表例の構造式を以下に示す。One of the forming components of the polyurethane resin of the present invention is a phosphorus compound represented by the above formulas (1) to (v). The structural formulas of representative examples of these phosphorus compounds are shown below.
式（１）の例
式（Ｉｆ）の例
式（Ｉ）の例
ＰＣＣＨｘＣＨ，ＯＨ）、 （１６） Ｐ（
ＣＭ、０Ｍ２０Ｈ）、 （１７）八Ｎａ
！
Ｋ
Ｐ（ＣＨ１ＣＨＩＣＨ２Ｃ％０ＴＩ）ｚ （２４）品
。Example of formula (1) Example of formula (If) Example of formula (I) PCCHxCH,OH), (16) P(
CM, 0M20H), (17) 8Na
! K P (CH1CHICH2C%0TI)z (24) product.
（、Ｎ８
、）Ｎ８
式俄の例
ＯＮａ ＯＩ
ｌｌ０００夏
（
ＩＩ
ＩＩ １１１！１
ｐ（ｃｏ、ｃｏ２ｃｒｔ、ｃｙｒ、ｏＨ）２（４３）Ｃ
Ｈ
ＯＮａ
ＨＯＣＨ，ＣＩ（２０ＣＨ２−Ｐ−ＣＨ２０ＣＲ，ＣＨ
，ＯＨ（４６）ＯＮａ
書
ＨｏｏＣＣｌ（２Ｃ１（ＩＣＨ２０ＣＪ−Ｐ−ＣＨ２０
ＣＨ２ＣＨ２ＣＪＣＯＯＨ（４Ｂ）ＣＨ
ＨＯＣＨ２ＣＨ２０ＣＲ，−Ｐ−ＣＨ，０ＣＩＩ２Ｃ！
１２０１１ （４９）ＩＩ
式（Ｖ）の例
本発明のポリウレタン樹脂形成性成分の１つである燐原
子以外の親水性極性基含有化合物が有すルカリ金属、テ
トラアルキルアンモニウム、テトラアルキルアンモニウ
ムを表わし、Ｒ１−Ｒ３は水＝ １６−
素原子炭素数１〜８のアルキル、アリール、アラルキル
を表わす。）を挙げることができる。(,N8,)N8 Example of formula ONa OI
ll000 summer (II
II 111!1 p(co, co2crt, cyr, oH)2(43)C
H ONa HOCH,CI(20CH2-P-CH20CR,CH
,OH(46)ONa BookHooCCl(2C1(ICH20CJ-P-CH20
CH2CH2CJCOOH (4B) CH HOCH2CH20CR, -P-CH,0CII2C!
12011 (49) II Example of formula (V) represents an alkali metal, tetraalkylammonium, or tetraalkylammonium possessed by a compound containing a hydrophilic polar group other than a phosphorus atom, which is one of the polyurethane resin-forming components of the present invention, R1-R3 represent water = 16- alkyl, aryl, or aralkyl having 1 to 8 carbon atoms. ) can be mentioned.
これらの親水性極性基を含有する具体的な化合物として
は下記の通りである。Specific compounds containing these hydrophilic polar groups are as follows.
（１） −ＣＯＯＭ
前記のポリエステルジオール■の酸成分であるポリカル
ボン酸、グリセリン酸、ジメチロールプｏピオン酸、Ｎ
、Ｎ−ジェタノールグリシン、ヒト四キシエチルオΦシ
安息香酸等のオキシカルボン酸、ジアミノプロピオン酸
、ジアミノ安息香酸等のアミノカルボン酸及びその誘導
体。(1) -COOM Polycarboxylic acid, glyceric acid, dimethylolpropionic acid, N
, N-jetanolglycine, oxycarboxylic acids such as human tetraxyethyloxybenzoic acid, aminocarboxylic acids such as diaminopropionic acid, diaminobenzoic acid, and derivatives thereof.
ヤ
２−ジメチルアミノメチル１．８−プロパツール、２−
メチ♂９４−ジメチルアミノ；ｔ、ａ−プロパンジオー
ル等の含窒素アルコール及びその誘導体。2-dimethylaminomethyl 1,8-propatur, 2-
Methy♂94-dimethylamino; nitrogen-containing alcohols such as t,a-propanediol and derivatives thereof.
Ｒ□
（８）Ｘｃ５
ピシリン酸、ジピコリン酸、アミノピリジン、ジアミノ
ピリジン、ヒドロキシピリジン、ジヒドロキシピリジン
、アミノヒドロキシピリジン、ピリジンジメタツール、
ピリジンプロパンジオール、ピリジンエタノール等のピ
リジン環含有化合物及びその誘導体。R□ (8) Xc5 Picillic acid, dipicolinic acid, aminopyridine, diaminopyridine, hydroxypyridine, dihydroxypyridine, aminohydroxypyridine, pyridine dimetatool,
Pyridine ring-containing compounds and derivatives thereof, such as pyridine propanediol and pyridine ethanol.
（４） −Ｓｏ、 Ｍ
５−ナトリウムスルホイソフタル酸、５−テトラブチル
ホスホニウム、スルホイソフタル酸、ナトリウムスルホ
コハク酸、等のポリカルボン酸及び誘導体、ナトリウム
スルホハイドロキノンーーよびアルキレンオキサイド付
加物、ナトリウムスルホビスフェノールＡ２よびアルキ
レンオキサイド付加物等。(4) -So, M Polycarboxylic acids and derivatives such as 5-sodium sulfoisophthalic acid, 5-tetrabutylphosphonium, sulfoisophthalic acid, sodium sulfosuccinic acid, sodium sulfohydroquinone and alkylene oxide adducts, sodium sulfobisphenol A2 and alkylene oxide adducts, etc.
これら特定の燐化合物は種々の過程を経て反応させるこ
とができる。例えば、ポリエステルポリオール（５）、
ポリアルキレングリコール等の原料樹脂を製造する際に
、その１成分として用いられることができる。特に、ポ
リエステルポリオール（５）を製造する際、上記式（１
）〜（ｖ）で表わされる燐化合物をポリエステルジオー
ル（５）の重合完結前の任意の段階で添加し、反応させ
ることができる。製造時の操業上の点からエステル交換
反応後またはエステル化反応後の段階で添加するのが好
ましい。These specific phosphorus compounds can be reacted through various processes. For example, polyester polyol (5),
It can be used as one component when manufacturing raw material resins such as polyalkylene glycol. In particular, when producing polyester polyol (5), the above formula (1
The phosphorus compounds represented by ) to (v) can be added and reacted at any stage before the completion of polymerization of the polyester diol (5). From the operational point of view during production, it is preferable to add it after the transesterification reaction or after the esterification reaction.
本発明で用いるポリウレタン樹脂の重付加反応は、全成
分を同時に反応させるワンク璽ット法、まずイソシアネ
ート過剰の条件下で長鎖ジオールを反応させ、得らｎる
イソシアネート基末端プレポリマーを鎖延長剤により、
さらに高分子化させるプレポリマー法とがある。本発明
で用いる熱可塑性ポリウレタン樹脂の場合、ワンシロッ
ト法、プレポリマー法のいずれの方法でも製造できる。The polyaddition reaction of the polyurethane resin used in the present invention is carried out by the Wanck method in which all components are reacted simultaneously. First, a long chain diol is reacted under conditions with an excess of isocyanate, and the resulting isocyanate group-terminated prepolymer is chain-extended. By the agent,
Furthermore, there is a prepolymer method in which the polymer is made into a polymer. In the case of the thermoplastic polyurethane resin used in the present invention, it can be produced by either the one-shot method or the prepolymer method.
。.
反応方法は原料を溶融状態で行なう方法、溶液中で溶解
して行なう方法があげられる。Examples of the reaction method include a method in which the raw materials are carried out in a molten state, and a method in which the raw materials are dissolved in a solution.
ブ′
反応触媒としてオクチル酸第−錫、ジプチル錫ジラウレ
ート、トリエチルアミン等を用いてもよい。As a reaction catalyst, stannous octylate, diptyltin dilaurate, triethylamine, etc. may be used.
ポリウレタン樹脂の分子ｆは６，０００〜５０，０００
の範囲にある。分子−Ｅｔ６，０００未満ではポリウレ
タン樹脂の機械的強度が低下し、または５０，０００を
越えると溶液粘度が高くなシすぎ取扱い上困難になるた
め好ましくない。The molecule f of polyurethane resin is 6,000 to 50,000
within the range of If the molecular weight -Et is less than 6,000, the mechanical strength of the polyurethane resin decreases, and if it exceeds 50,000, the solution viscosity becomes too high and it becomes difficult to handle, which is not preferred.
上記一般式（Ｉ）〜式（ト）で示される燐化合物は、樹
脂中に燐原子として２００ＰＰｍ 〜５００００ｐｐｍ
含まれるように使用するのが適当であり、上記範囲より
小さくなれば磁性粒子に対する分散性が低下し、一方、
上記範囲より大きくなれば吸湿性の増大、物理的特性の
低下、非磁性支持体に対する密着性の低下等を生じ、実
用性が少なくなる。The phosphorus compounds represented by the above general formulas (I) to (g) contain 200PPm to 50,000ppm of phosphorus atoms in the resin.
If it is smaller than the above range, the dispersibility for magnetic particles will decrease, and on the other hand,
If it is larger than the above range, there will be an increase in hygroscopicity, a decrease in physical properties, a decrease in adhesion to a non-magnetic support, etc., and the practicality will be reduced.
これら特定の燐化合物以外の親水性極性基を含有する化
合物は、特定の燐化合物と同様にして原料樹脂製造の際
、１成分として反応させることが可節である。特に活性
水素を含有する誘導体を前配鎖延剤０又は、末端停止剤
として、用いることが好ましい。これらの親水性極性基
は燐原子に対し０．０１〜１００（当量比）の範囲にあ
ることが望ましい。さらに好ましくけ０．１〜１０の範
囲である。Compounds containing hydrophilic polar groups other than these specific phosphorus compounds can be reacted as one component during production of the raw resin in the same manner as the specific phosphorus compounds. In particular, it is preferable to use a derivative containing active hydrogen as a pre-chain extension agent or a terminal stopper. It is desirable that these hydrophilic polar groups exist in a range of 0.01 to 100 (equivalent ratio) to the phosphorus atom. More preferably, it is in the range of 0.1 to 10.
親水性極性基が燐原子に対し１０ｏ（当量比）を越える
場合は、基材に対する密着性が低下し好ましくなく ０
．０１に満たない場合は磁気塗料の安定性が極端に損な
わｎ１好ましくない。If the hydrophilic polar group exceeds 10o (equivalent ratio) to the phosphorus atom, the adhesion to the substrate will decrease, which is undesirable.
．． If n1 is less than 01, the stability of the magnetic coating material will be extremely impaired, which is undesirable.
喘ン
本発明に２いては、一般式 （Ｖ）で示される燐化合
物全反応させた樹脂以外に、磁気テープの可撓性の調整
、耐熱性・耐寒性の向上、耐摩耗性の向上等の目的で他
の相溶性のある樹脂を添加するか、本発明の樹脂と反応
して架橋する化合物を混合することが望ましい。In the second aspect of the present invention, in addition to the resin completely reacted with the phosphorus compound represented by the general formula (V), it is possible to adjust the flexibility of the magnetic tape, improve the heat resistance and cold resistance, and improve the abrasion resistance. For this purpose, it is desirable to add another compatible resin or to mix a compound that reacts with and crosslinks the resin of the present invention.
本発明の樹脂と相溶性のある樹脂としては、塩化ビニル
系樹脂、ポリエステル系樹脂、セルロース系樹脂、アク
リル系樹脂、エポキシ樹脂、フェア、熱可塑性ポリウレ
タン樹脂と架橋する化合物としてはポリイソシアネート
化合物、エポキシ樹脂、メラミン樹脂、尿素樹脂等があ
シ、特にこれらの中でポリイソシアネート化合物が特に
望ましい。Resins that are compatible with the resin of the present invention include vinyl chloride resins, polyester resins, cellulose resins, acrylic resins, epoxy resins, fair, and compounds that crosslink with thermoplastic polyurethane resins include polyisocyanate compounds and epoxy resins. Among them, polyisocyanate compounds are particularly desirable.
本発明にシーいて使用される強磁性粒子としてけｒ−Ｆ
ｉｓｈｓ ＋ ｒ−ＦｉｓｈｓとＦｅｍ０ａの混晶、０
ｒｂｓ、コバルトフェライト、コバルト吸着酸化鉄、バ
リウムフェライト、Ｆｅ −Ｏｏ％Ｆｓ −Ｏｏ −Ｎ
ｉ等の強磁性合金粉末などをあげることができる。As the ferromagnetic particles used in the present invention, r-F
ishs + r-Fishs and Fem0a mixed crystal, 0
rbs, cobalt ferrite, cobalt adsorbed iron oxide, barium ferrite, Fe -Oo%Fs -Oo -N
Examples include ferromagnetic alloy powders such as i.
本発明の磁気記録媒体には必要に応じてジブチルフタレ
ート、トリフェニルホスフェートのような可塑剤、ジオ
クチルスルホナトリウムサクシネート、ｔ−プチルフェ
ノールーポリエテレンエーテル、エチルナフタレン−ス
ルホン酸ソーダ、ジラウリルサククネート、ステアリン
酸亜鉛、大豆油レシチン、シリコーンオイルのような潤
滑油や種々の帯電防止剤を添加することもできる。The magnetic recording medium of the present invention may optionally contain plasticizers such as dibutyl phthalate and triphenyl phosphate, dioctyl sulfonodium succinate, t-butylphenol-polyetherene ether, ethylnaphthalene-sodium sulfonate, and dilauryl sulfonate. Lubricating oils and various antistatic agents can also be added, such as nate, zinc stearate, soybean oil lecithin, silicone oil.
強磁性粉末を結合剤中に分散させた磁性材料は一般に溶
剤を使用するが、その溶剤としては、アセトン、メチル
エチルケトン、メチルイソブチルケトン、シクロヘキサ
ノン等のケトン類、メタノールなどのアルコール類、酢
酸メチル、酢酸エチル、酢酸ブチル、酪酸エチルなどの
エステル類、エチレングリコールジメチルエーテル、エ
チレングリコールモノエチルエーテル、ジオキサンなど
のグリコールエーテル類、ベンゼン、トルエン、キシレ
ンなどの芳香族炭化水素類、ヘキサン、へブタンなどの
脂肪族炭化水素類またはこれらの混合物などが使用でき
る。Magnetic materials in which ferromagnetic powder is dispersed in a binder generally use a solvent. Examples of such solvents include ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone, alcohols such as methanol, methyl acetate, and acetic acid. Esters such as ethyl, butyl acetate, and ethyl butyrate, glycol ethers such as ethylene glycol dimethyl ether, ethylene glycol monoethyl ether, and dioxane, aromatic hydrocarbons such as benzene, toluene, and xylene, and aliphatic hydrocarbons such as hexane and hebutane. Hydrocarbons or mixtures thereof can be used.
本発明の磁気記録媒体は上記磁性材料を非磁性支持体上
に塗布する。使用できる非磁性支持体の素材としては、
例えばポリエチレンテレフタレートなどのポリエステル
、ポリプロピレンなどのポリオレフィン、セルロースト
リアセテートやセルロースジアセテートなどのセルロー
ス誘導体、ポリカーボネート、ポリ塩化ビニル、ポリイ
ミド、アルミニウムや銅などの金属、紙などが挙げられ
る。In the magnetic recording medium of the present invention, the magnetic material described above is coated on a non-magnetic support. Materials for non-magnetic supports that can be used include:
Examples include polyesters such as polyethylene terephthalate, polyolefins such as polypropylene, cellulose derivatives such as cellulose triacetate and cellulose diacetate, polycarbonate, polyvinyl chloride, polyimide, metals such as aluminum and copper, and paper.
磁性材料を非磁性支持体上に常法に従って塗布し乾燥さ
せた後、その塗膜を必要によりカレンダー処理してから
熱処理する。熱処理後にカレンダー処理することもでき
る。約１−１０Ｍｒａｄがよく、特に約２〜８Ｍｒａｄ
であることが好ましい。After a magnetic material is coated on a non-magnetic support according to a conventional method and dried, the coating film is calendered if necessary and then heat-treated. Calendar treatment can also be performed after heat treatment. About 1-10 Mrad is good, especially about 2-8 Mrad.
It is preferable that
（作 用）
本発明では燐化合物−−よびその他の親水性極性基を含
有する化合物を反応させたポリウレタン樹脂を結合剤の
少なくとも一成分として用いることにより、得られる熱
硬化した塗膜がポリウレタン樹脂の有する機械的特性を
保持したま＼、磁性粒子の分散性を向上させることがで
き、分散性に起因する特性、たとえば、磁性粒子の充填
性、配向性、磁性層の平滑性が優れ、粉落ちの少ない耐
久性の良いものとなる。(Function) In the present invention, by using a polyurethane resin reacted with a phosphorus compound and other hydrophilic polar group-containing compounds as at least one component of the binder, the resulting thermoset coating film is made of polyurethane resin. The dispersibility of the magnetic particles can be improved while maintaining the mechanical properties possessed by the powder, and the properties resulting from the dispersibility, such as the packing properties of the magnetic particles, the orientation, and the smoothness of the magnetic layer, are excellent, making it possible to improve the dispersibility of the magnetic particles. It is highly durable and does not easily fall off.
（実 施 例）
以下、本発明を実施例によって具体的に訝明する。実施
例中、単に部とあるのは重量部を示す。(Examples) Hereinafter, the present invention will be specifically explained using examples. In the examples, parts simply indicate parts by weight.
ポリエステルジオールの製造例１゜
７゛
温度計、攪拌機を具備したオートクレーブ中に、ジメチ
ルテレフタレート４８５部、ジメチルイソフタレート４
８５部、エチレングリコール４０９部、ネオペンチルグ
リコール４５８部およびテトラブトキシチタネート０．
６８部を仕込み、１５０〜２８０℃で１２０分間加熱し
エステル交換を行い、次いで前記燐化合物（１Ｂ）５０
．１部を仕込み、２２０〜２８０℃で更に１時間反応を
行った。次いで反応系１に８０分間で２５０℃まで昇温
し、系の圧力を徐々に減じ４５分後に１０ ｍｍＨｆと
し、この条件で更に６０分間反応を続けた。得られたポ
リエステルジオールＡの分子量は２５００、燐含有率は
１，６００ｐｐｍであった。Production example of polyester diol 1゜7゛In an autoclave equipped with a thermometer and a stirrer, 485 parts of dimethyl terephthalate and 4 parts of dimethyl isophthalate were added.
85 parts, 409 parts of ethylene glycol, 458 parts of neopentyl glycol, and 0.85 parts of tetrabutoxy titanate.
68 parts of the phosphorus compound (1B) were charged, heated at 150 to 280°C for 120 minutes to perform transesterification, and then 50 parts of the phosphorus compound (1B)
．． 1 part was charged, and the reaction was further carried out at 220 to 280°C for 1 hour. Next, the temperature of reaction system 1 was raised to 250° C. over 80 minutes, and the pressure of the system was gradually reduced to 10 mmHf after 45 minutes, and the reaction was continued under these conditions for an additional 60 minutes. The obtained polyester diol A had a molecular weight of 2,500 and a phosphorus content of 1,600 ppm.
同様の製造方法により得られたポリエステルジオールＢ
−Ｅ４第１表に示した。樹脂組成はＮＭＲよシ分析した
。第１表中のポリエステルジオールＥけ重合中に粘度の
上昇が見られなかった。Polyester diol B obtained by a similar manufacturing method
-E4 Shown in Table 1. The resin composition was analyzed by NMR. No increase in viscosity was observed during polymerization of polyester diol E in Table 1.
ポリエステルジオールＥの構成単位は原料仕込み時の酸
成分及びグリコール成分のモル比を表わす。The structural unit of polyester diol E represents the molar ratio of the acid component and glycol component at the time of charging the raw materials.
第１表
イ列
ポリウレタン樹脂の合成化
温度計、攪拌機、還流式冷却器を具備した反応容器中に
、トルエン１４７部、メチルエチルケトン１４７部、前
記ポリエステルジオールＡ１００部、グリセリン酸５．
７部、２よびゲル化防止剤としてＰ−）ルエンスルホン
酸し０１部を仕込み、溶解後、４・４′−ジフェニルメ
タンジイソシアネート２１部およびジプチル錫ジラウレ
ー） ０．０５部を仕込み、７０〜８０℃で１０時間反
応させた。Synthesis of Polyurethane Resin (Table 1) In a reaction vessel equipped with a thermometer, a stirrer, and a reflux condenser, 147 parts of toluene, 147 parts of methyl ethyl ketone, 100 parts of the polyester diol A, and 5.0 parts of glyceric acid were placed.
After dissolving, 7 parts of 4,4'-diphenylmethane diisocyanate and 0.05 part of dibutyltin dilaurate were added, and the mixture was heated at 70 to 80°C. The mixture was allowed to react for 10 hours.
得られたポリウレタン樹脂溶液は固型分濃度８０チ、溶
液粘度５０ボンズ（２５℃）、ポリウレタン樹脂Ａの分
子１ｆｉ２１，０００であった。同様の製造方法により
得らｎたポリウレタン樹脂Ｂ〜Ｉを第２表に示した。The obtained polyurethane resin solution had a solid content concentration of 80 inches, a solution viscosity of 50 bonds (at 25° C.), and a polyurethane resin A molecule of 1fi of 21,000. Polyurethane resins B to I obtained by the same manufacturing method are shown in Table 2.
実施例１〜５、比較例１．２．８
下記の配合割合の組成物をボールミルに入れて４８時間
分散してから、イソシアネート化合物、コロネー） ２
０８０（日本ポリウレタン工業■製）を硬化剤として５
部加え、更に１時間混合して磁性塗料を得た。これを厚
み１２μのポリエチレンテレフタレートフィルム上に、
乾燥後の厚みが５μになるように、２．０００ガラスの
磁場全印加しつつ塗布した。５０℃、２日間放置後１イ
ンチ巾にスリットし、磁気テープを得た。Examples 1 to 5, Comparative Example 1.2.8 A composition having the following blending ratio was placed in a ball mill, dispersed for 48 hours, and then mixed with an isocyanate compound (Coronet) 2
5 using 080 (manufactured by Nippon Polyurethane Industries) as a curing agent.
1 part was added and further mixed for 1 hour to obtain a magnetic paint. This was placed on a 12μ thick polyethylene terephthalate film.
The coating was applied while applying a full magnetic field of 2.000 glass so that the thickness after drying was 5 μm. After being left at 50° C. for 2 days, it was slit into 1 inch width to obtain a magnetic tape.
ポリウレタン樹脂入溶液 １００部（固型分
８０％、ＭＥＫ／）ルエン＝ｌ／１溶液）コバルト被着
γ−ｙｅｘｏｓ １２０部オリーブ油
１部シクロヘキサノン
５０部トルエン
１００部ＭＥＫ
５０部得られた磁性塗料２よびテープの各物性を第８
表に示す。Polyurethane resin solution 100 parts (solid content 80%, MEK/Luene = l/1 solution) Cobalt coated γ-yexos 120 parts Olive oil
1 part cyclohexanone
50 parts toluene
100 copies MEK
The physical properties of the magnetic paint 2 and tape obtained in 50 parts were
Shown in the table.
烏♂ゝ−
第８表
（来）： 試験管に磁性塗料ｋｌＯｔＭの高さになる
ように入れ、室温で２４ｈｒｓに放置した後、分離した
磁性塗料の液面の高さを測定した。烏♂ゝ Table 8 (Next): The magnetic paint was placed in a test tube at a height of klOtM, and after being left at room temperature for 24 hours, the height of the liquid level of the separated magnetic paint was measured.
（未来）： 磁化可能層の表面の目視判定（舶昧）
： メチルエチルケトン含浸ガーゼを用い塗膜をこす
る。(Future): Visual determination of the surface of the magnetizable layer (unclear)
: Rub the paint film using gauze impregnated with methyl ethyl ketone.
（基材が露出するのに要したこすり回数）第８表から明
らかなように、ポリウレタン樹脂Ａ−Ｄｉ用いた磁気記
録媒体はＢｒ／８ｍ、密着性、平滑性および耐溶剤性に
２いて優れるばかりでなく磁性塗料の安定性に優れる。(Number of rubbings required to expose the base material) As is clear from Table 8, the magnetic recording medium using the polyurethane resin A-Di has an excellent Br/8m, adhesion, smoothness, and solvent resistance. Not only that, but it also has excellent stability for magnetic paints.
（発明の効果）
従来、ポリウレタン樹脂中にホスフィン酸２よびホスホ
ン酸等の燐化合物の金属塩基を導入することが困難であ
ったのに対し、容易にこれらの親水基を導入することが
できるばかシか、磁性粉の分散性および磁性塗料の安定
性に有効であシ、かつ基本骨格を形成するベース樹脂の
特性を少しもそこなっていない。(Effect of the invention) Conventionally, it was difficult to introduce metal bases of phosphorous compounds such as phosphinic acid 2 and phosphonic acid into polyurethane resins, but now it is possible to easily introduce these hydrophilic groups. However, it is effective in improving the dispersibility of magnetic powder and the stability of magnetic paint, and does not impair the properties of the base resin forming the basic skeleton in the slightest.
Claims (1)
材料を塗布した磁気記録媒体において、ポリウレタン樹
脂形成性成分として下記式（ I ）〜（Ｖ）で示される
燐化合物の少なくとも１種および燐原子以外の親水性極
性基含有化合物を含有する分子量６，０００〜５０，０
００の燐含有ポリウレタン樹脂を上記結合剤の成分とし
て使用することを特徴とする磁気記録媒体。 ▲数式、化学式、表等があります▼（ I ）▲数式、化
学式、表等があります▼（II）▲数式、化学式、表等が
あります▼（III） ▲数式、化学式、表等があります▼（IV）▲数式、化学
式、表等があります▼（Ｖ） 〔Ｘ、Ｙはエステル形成性官能基、Ｒ＿１は炭素数３〜
１０の３価の炭化水素基、Ｒ＿２は炭素数１〜１２のア
ルキル基、シクロアルキル基、アリール基、炭素数１〜
１２のアルコキシ基、シクロアルコキシ基、又はアリー
ルオキシ基を示す。アリール基およびアリールオキシ基
はハロゲン原子、ヒドロキシル基、−ＯＭ′（Ｍ′はア
ルカリ金属を示す）またはアミノ基が結合したものでも
良い。Ｒ＿３、Ｒ＿４は、炭素数１〜１２のアルキレン
基、シクロアルキレン基、アリーレン基、次式：−（Ｃ
Ｈ＿２−ＯＲ＿５）＿ｍ−で表される基（Ｒ＿５は炭素
数１〜１２のアルキレン基、シクロアルキレン基、アリ
ーレン基を示す。ｍは１〜４の任意の数値をとることが
できる。）、Ｍはアルカリ金属原子、水素、１価の炭化
水素基、又はアミノ基を示す。〕[Claims] In a magnetic recording medium in which a magnetic material in which ferromagnetic powder is dispersed in a binder is coated on a non-magnetic support, the polyurethane resin-forming component is represented by the following formulas (I) to (V). Molecular weight 6,000 to 50,0 containing at least one phosphorus compound and a hydrophilic polar group-containing compound other than a phosphorus atom
A magnetic recording medium characterized in that a phosphorus-containing polyurethane resin of No. 00 is used as a component of the binder. ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (I) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (II) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (III) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ( IV) ▲Mathematical formulas, chemical formulas, tables, etc.▼(V) [X, Y are ester-forming functional groups, R_1 has 3 to 3 carbon atoms
10 trivalent hydrocarbon groups, R_2 is an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group, an aryl group, and 1 to 12 carbon atoms.
12 shows an alkoxy group, a cycloalkoxy group, or an aryloxy group. The aryl group and aryloxy group may have a halogen atom, a hydroxyl group, -OM'(M' represents an alkali metal) or an amino group bonded thereto. R_3 and R_4 are an alkylene group having 1 to 12 carbon atoms, a cycloalkylene group, an arylene group, and the following formula: -(C
H_2-OR_5)_m- (R_5 represents an alkylene group, cycloalkylene group, or arylene group having 1 to 12 carbon atoms. m can take any numerical value from 1 to 4.), M represents an alkali metal atom, hydrogen, a monovalent hydrocarbon group, or an amino group. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3767686A JPS62195720A (en) | 1986-02-21 | 1986-02-21 | Magnetic recording medium |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3767686A JPS62195720A (en) | 1986-02-21 | 1986-02-21 | Magnetic recording medium |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62195720A true JPS62195720A (en) | 1987-08-28 |
Family
ID=12504221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3767686A Pending JPS62195720A (en) | 1986-02-21 | 1986-02-21 | Magnetic recording medium |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62195720A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5443913A (en) * | 1992-10-16 | 1995-08-22 | Tdk Corporation | Magnetic recording medium |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS595423A (en) * | 1982-07-01 | 1984-01-12 | Sony Corp | Magnetic recording medium |
| JPS59154634A (en) * | 1983-02-23 | 1984-09-03 | Toyobo Co Ltd | Magnetic recording medium |
-
1986
- 1986-02-21 JP JP3767686A patent/JPS62195720A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS595423A (en) * | 1982-07-01 | 1984-01-12 | Sony Corp | Magnetic recording medium |
| JPS59154634A (en) * | 1983-02-23 | 1984-09-03 | Toyobo Co Ltd | Magnetic recording medium |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5443913A (en) * | 1992-10-16 | 1995-08-22 | Tdk Corporation | Magnetic recording medium |
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