US3834929A - Color developer sheet for pressure sensitive recording paper - Google Patents
Color developer sheet for pressure sensitive recording paper Download PDFInfo
- Publication number
- US3834929A US3834929A US00208894A US20889471A US3834929A US 3834929 A US3834929 A US 3834929A US 00208894 A US00208894 A US 00208894A US 20889471 A US20889471 A US 20889471A US 3834929 A US3834929 A US 3834929A
- Authority
- US
- United States
- Prior art keywords
- color
- color developer
- sheet
- phenol
- phenol compound
- 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.)
- Expired - Lifetime
Links
- -1 PHENOL COMPOUND Chemical class 0.000 abstract description 46
- 229910000765 intermetallic Inorganic materials 0.000 abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 150000003839 salts Chemical class 0.000 description 15
- 238000000576 coating method Methods 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000004927 clay Substances 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- 239000011230 binding agent Substances 0.000 description 7
- 230000008034 disappearance Effects 0.000 description 7
- 239000003094 microcapsule Substances 0.000 description 7
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 5
- 229940031826 phenolate Drugs 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 229920000084 Gum arabic Polymers 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000000205 acacia gum Substances 0.000 description 4
- 235000010489 acacia gum Nutrition 0.000 description 4
- 150000002596 lactones Chemical class 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 230000003595 spectral effect Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- LINPIYWFGCPVIE-UHFFFAOYSA-N 2,4,6-trichlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1Cl LINPIYWFGCPVIE-UHFFFAOYSA-N 0.000 description 2
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 2
- 244000171897 Acacia nilotica subsp nilotica Species 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 241000978776 Senegalia senegal Species 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect 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
- 229940093499 ethyl acetate Drugs 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- WALBTDFSFTVXII-UHFFFAOYSA-N 2,3,4,5,6-pentamethylphenol Chemical compound CC1=C(C)C(C)=C(O)C(C)=C1C WALBTDFSFTVXII-UHFFFAOYSA-N 0.000 description 1
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical class OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
- CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical compound OC1=CC=CC=C1C#N CHZCERSEMVWNHL-UHFFFAOYSA-N 0.000 description 1
- ZWTZHHHSRDUVRT-UHFFFAOYSA-N 2-methylsulfonylphenol Chemical compound CS(=O)(=O)C1=CC=CC=C1O ZWTZHHHSRDUVRT-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- ACNUVXZPCIABEX-UHFFFAOYSA-N 3',6'-diaminospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(N)C=C1OC1=CC(N)=CC=C21 ACNUVXZPCIABEX-UHFFFAOYSA-N 0.000 description 1
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 1
- JSUKRBMPOXGCPR-UHFFFAOYSA-N 4-(benzenesulfonyl)phenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=CC=C1 JSUKRBMPOXGCPR-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 1
- QESYLFCJDFCRIT-UHFFFAOYSA-N 4-hydroxybenzene-1,3-dicarbonitrile Chemical compound OC1=CC=C(C#N)C=C1C#N QESYLFCJDFCRIT-UHFFFAOYSA-N 0.000 description 1
- KECCFSZFXLAGJS-UHFFFAOYSA-N 4-methylsulfonylphenol Chemical compound CS(=O)(=O)C1=CC=C(O)C=C1 KECCFSZFXLAGJS-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 1
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- KYPYTERUKNKOLP-UHFFFAOYSA-N Tetrachlorobisphenol A Chemical compound C=1C(Cl)=C(O)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1 KYPYTERUKNKOLP-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- ZKURGBYDCVNWKH-UHFFFAOYSA-N [3,7-bis(dimethylamino)phenothiazin-10-yl]-phenylmethanone Chemical compound C12=CC=C(N(C)C)C=C2SC2=CC(N(C)C)=CC=C2N1C(=O)C1=CC=CC=C1 ZKURGBYDCVNWKH-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000005354 coacervation Methods 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 235000002867 manganese chloride Nutrition 0.000 description 1
- 239000011565 manganese chloride Substances 0.000 description 1
- 229940099607 manganese chloride Drugs 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- PFPDWGGTEJAIIG-UHFFFAOYSA-L sodium nickel(2+) sulfate Chemical compound [Ni+2].S(=O)(=O)([O-])[O-].[Na+] PFPDWGGTEJAIIG-UHFFFAOYSA-L 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/132—Chemical colour-forming components; Additives or binders therefor
- B41M5/155—Colour-developing components, e.g. acidic compounds; Additives or binders therefor; Layers containing such colour-developing components, additives or binders
Definitions
- a color developer sheet for pressure sensitive recording paper comprising a color developer layer containing a metallic compound of a phenol compound, said phenol compound pKa below 8.
- the present invention relates to a color developer sheet for pressure sensitive recording paper. More particularly, the present invention relates to a color developer sheet for pressure sensitive recording paper using a metallic phenol compound which is a metal phenolate and which has not hitherto been used as a color developer.
- Pressure sensitive recording papers utilize the reaction of a colorless organic compound (hereinafter referred to as a color former) and a color developing material (hereinafter referred to as a color developer) capable of reacting with the above color former to form a colored product.
- a color former a colorless organic compound
- a color developing material hereinafter referred to as a color developer
- pressure sensitive recording papers are composed of a sheet (color former sheet) having coated thereon microcapsules containing a solution of color former in an organic solvent and a sheet (color developer sheet) having coated thereon a color developer with a binder, and may include a sheet having coated on one side a color developer and on the other side the microcapsules (such assemblies are hereinafter referred to as pressure sensitive duplicating papers). Sheets are also formed having microcapsules and the color developer on the same side of the support (called single recording paper).
- malchite green lactone benzoyl leucomethylene blue, crystal violet lactone, Rhodamin B lactam, 3-dialkylamino-7-dialkylamino fluoranes, 3-alkyl- 2,2-spiro bi(benzo f Chromene), etc. have been used.
- clays such as acidic clay, attapulgite, kaoline, geolite, pyrophilite, bentonite, haloycite, and phenol compounds such as pcresol, p-phenyl phenol, pentachlorophenol, pentamethylphenol, p,p'-biphenol, 5,5 diethyl-o,o-biphenol, 2,2- rnethylene bis (4-chlorophenol), 4,4-thiodiphenol, etc. as described in the specification of Japanese Pat. 465,300.
- clays such as acidic clay and active clay are usually employed.
- color developer clays have a higher color developing ability than that of other color developers (p-cresol, p-phenylphenol and the like), the color developing ability thereof is lowered when it is exposed to sun-light.
- the colored body on the color developer sheet has the defect that when wet with water the color disappears or is lowered in concentration.
- the color developer sheets using the above described phenol compounds cannot be used as a practical matter since although they have good water proofness as a colored body on the sheet, they are low in color developing ability, which is most important and also is poor in light resistance of the colored body 011 the sheet.
- the present inventors have found that by using a metallic phenol compound as a color developer a color developer sheet which is high in color developing ability, good in water resistance as a colored body and exhibits less lowering of activity can be obtained.
- the object of the present invention is thus to provide a color developer sheet for pressure sensitive duplicating papers which meets the above criteria and does not have the substantial defects of the prior art color developer.
- the metallic compound of phenol used in the present invention is obtained by reacting an alkali metal salt of a phenol compound and a water soluble metallic salt in a solvent.
- the alkali metal salt of the phenol compound and the water soluble metallic salt can be used at any ratio, although the water soluble metallic salt is preferably used in an amount greater than 1 gram equivalent per gram equivalent of the alkali metal salt of the phenolic compound.
- the reaction can be attained by adding an aqueous solution of a water-soluble metal compound to an aqueous solution of alkali metal salt of phenol compound.
- the addition of the compounds may be carried out in reverse order, of course. 7
- reaction condition such as temperature or pressure are of no importance, and the reaction proceeds at normal condition.
- an alkali salt of phenol or its aqueous solution is by reacting the base phenol compound with an alkali metal, a hydroxide or carbonate of the alkali metal in an amount of one gram equivalent or more of the above hydroxide or carbonate per one gram mole of the alkali salt of phenol.
- Other methods may, of course, be used, but the above method is very simple.
- phenols having pKa of below 8 such as 2,4-dichlorophenol, 2,4,6-trichlorophenol, pentachlorophenol, pnitrophenol, p-methylsulfonyl-phenol, methylsulfonyl phenol, 4-phenyl sulfonyl phenol, 4-cyanophenol, 2,4-dicyanophenol, 4- cyano-Z-chlorophenol, 2,4-dichloro-4-cyanophenol, tetrachloro-bis phenol A, 4,4-dihydroxy-3,3'-dichlorodiphenylsulfone, 4,4 dihydroxy 3,3',5,5'- tetrachlorodiphenyl sulfone, etc. are effective.
- the present inventors have tried to synthesize a metallic phenol compound from a phenol compound above 8 in pKa.
- a phenol compound of above 8 in pKa does not make a metallic compound as shown by the infra-red absorption curves and the color developing ability of the product. These are not different from those of the phenol monomer compound itself.
- pKa log (acidity constant).
- water soluble metallic salts used in the present ine as chromium, molybdenum, etc., Group VIIb metals such as manganese, etc., and Group VIII metals such as cobalt, nickel, etc.
- water soluble salts of zinc, nickel, manganese, copper, magnesium, calcium are particularly preferred.
- water soluble metallic salts inorganic salts such as chlorides, sulfates, nitrates, etc. and organic salts such as acetates, oxalates, etc. of the above described metals can be employed.
- At least one metallic phenol compound produced by the reaction of the above described alkaline phenol salt and the above described water soluble metallic salt is coated with a binder onto a support such as paper, synthetic paper etc., in an amount of above 0.1 g./m. desirably 0.2 to 5 g./m.
- the upper limit of the coating amount is primarily determined by reasons of economy and coating workability.
- the binder is not necessarily used (that is, the metallic phenol compound is dissolved for use as an ink), but if it is used, the amount thereof is preferably from about 5 to about 50 parts by weight, preferably parts by weight, based on 100 parts by weight of the metallic phenol compound.
- the amount thereof is preferably from about 5 to about 50 parts by weight, preferably parts by weight, based on 100 parts by weight of the metallic phenol compound.
- water or various organic solvents can be used alone or in any mixing ratio.
- the organic solvents used include methanol, ethanol, butanol, acetone, n-butyl acetate, benzene, toluene, methylene chloride, etc.
- cellulose derivatives such as nitrocellulose, natural or synthetic polymers such as vinyl acetate, vinyl chloride, polyamide, polyacrylic acid, styrenebutadiene copolymer, casein, polyvinyl alcohol, gelatine, gum arabic, etc.
- latexes such as styrene-butadiene latex, butadienemethylmethacrylate latex, etc.
- any polymeric binder used in the prior art can be used for the same purpose in the present invention.
- the color developer sheet using the color developer of the present invention may be used in combination with a color former sheet and there may be arranged thereon a rnicrocapsule layer containing a color former.
- the color developer of the present invention may also be mixed with the microcapsules and coated onto a support, for example, a paper.
- a color developer ink containing the above compound can be printed onto a paper by a printing process.
- the color developer sheet using the color developer of the present invention has the following excellent effects in comparison with the conventional color developer sheet using clays such as acidic clay, etc.
- Clay paper is remarkably lowered in color developing ability when it is allowed to stand in a room and the color developer sheet of the present invention is greatly improved at this point.
- the colored material on the color developer sheet of the present invention is not lowered in concentration even if wet with water.
- sufficient color developing ability and other properties necessary for a color developer sheet for pressure sensitive recording paper are satisfied with a smaller amount of coating than in conventional clay paper. That is, conventional clay paper requires a coating amount of 7 to 10 g./m. while the color developer of the present invention is suffi cient at a coating amount of 0.2-5 g./m.
- a small amount of coating is sufiicient and the physical properties of the coating liquid can be freely varied in a manner impossible with clay coatings.
- the same color developing ability can be obtained with smaller amount of coating.
- a color developer sheet using a metallic phenol compound is remarkably higher in color developing ability and in light fastness of the colored material formed up on the color developer sheet, as compared to a color developer sheet using a phenol compound per se as a color developer.
- the effect of the color developer sheet of the present invention was confirmed with the following color former sheet.
- the microcapsules containing color former were manufactured according to U.S. Pat. 2,800,457, using the following procedure.
- Example 1 0.01 g. equivalent of caustic soda was dissolved in 30 ml. of warm water and 0.01 g. equivalent of phenol compound (see Table 1) was dissolved therein. 0.01 g. equivalent of the below described water soluble metallic salt dissolved in 10 ml. of warm water was then added to this solution with stirring.
- Crystals immediately precipitated out.
- the crystals were filtered and washed with water several times and dried.
- the product obtained by the above method was dissolved or dispersed in 30 ml. of ethanol to obtain a coating liquid.
- This coating liquid was coated onto a 40 g./m. paper by a glass tube at a solid content of 0.5 g./m. and dried to obtain a color developer sheet.
- Comparative Example 1 3 g. of phenol compound per se were dissolved in 30 ml. of ethanol and the resulting ethanol solution was coated on a 40 g./rn. paper by a glass tube at solids content of 0.5 g./m. and dried to obtain a color developer sheet.
- Example 2 0.01 g. equivalent of caustic soda was dissolved in 30 ml. of warm water and 0.01 g. equivalent of phenol compound was dissolved therein. 0.01 g. equivalent of the below described water soluble metallic salt dissolved in 10 ml. of warm water was added to this solution with stirring.
- the colored body produced in accordance with the present invention was not lowered in color concentration even if Test results wetted with water.
- Example 1 The color developer sheet of Example 1 and Com- 'For other color formers the same results were obparative Example 1 were color developed by stocking tained.
- benzylamino-7-diethylamino-fiuorane color formers was for 1 hour, the spectral absorption curve in the 700 to high, and the light fastness of the colored body was high. 400 m wave length region was measured and the con- In addition, the colored body was not lowered in color centration at the maximum absorption (wave length 610 concentration even if wetted with water.
- the ink was diluted with a mixed tm xim m losor tion Concentmmon i n p S nu ht solvent of ethyl acetate and ethanol (1:1) so that the 1 a 1 10 W1 u 100 40 viscosity was about 0.7 poise, and printing was conducted Flesh concentration at maximum absorption by the flexo printing method to give a 3 2 dried To measure the spectral absorption curve a Beckmann film. spectroscope Type DB (manufactured by Toshiba Co.) Thus obtained developer sheet was contacted with a was d color former sheet same as in the former Examples to (2) A color developer sheet coated with a microcapbtam the similar results.
- Dlsappearance 0.119 Disappearance
- the color developer sheet of the present invention was thus formed to be remarkably higher in color developing group consisting of Group Ib, Group Ila, Group IIb, Group IIIa, Group IVa, Group VIb, Group VIII) and Group VIII of the Periodic Table.
- said color former is present in a color former sheet different from said support sheet having coated thereon said color developer layer.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Color Printing (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP45118978A JPS521329B1 (enrdf_load_stackoverflow) | 1970-12-26 | 1970-12-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3834929A true US3834929A (en) | 1974-09-10 |
Family
ID=14749975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00208894A Expired - Lifetime US3834929A (en) | 1970-12-26 | 1971-12-16 | Color developer sheet for pressure sensitive recording paper |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3834929A (enrdf_load_stackoverflow) |
| JP (1) | JPS521329B1 (enrdf_load_stackoverflow) |
| AU (1) | AU465050B2 (enrdf_load_stackoverflow) |
| CA (1) | CA948496A (enrdf_load_stackoverflow) |
| DE (1) | DE2163905A1 (enrdf_load_stackoverflow) |
| ES (1) | ES397920A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1350011A (enrdf_load_stackoverflow) |
| IE (1) | IE36855B1 (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4348234A (en) * | 1979-03-20 | 1982-09-07 | Ciba-Geigy Corporation | Coating compositions for the production of a recording material |
| US4453744A (en) * | 1981-06-15 | 1984-06-12 | Ciba-Geigy Corporation | Pressure-sensitive or heat-sensitive recording material |
| US4536779A (en) * | 1982-12-10 | 1985-08-20 | Ciba-Geigy Corporation | Heat-sensitive recording material |
| US4556687A (en) * | 1984-03-19 | 1985-12-03 | The Standard Register Company | Color developer for pressure-sensitive recording papers |
| US4614757A (en) * | 1984-03-19 | 1986-09-30 | The Standard Register Company | Color developer for pressure-sensitive recording papers |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5457244U (enrdf_load_stackoverflow) * | 1977-09-29 | 1979-04-20 | ||
| GB2032484B (en) * | 1978-10-11 | 1983-01-19 | Mitsui Toatsu Chemicals | Colour-developing sheet for pressure-sensitive recording sheets |
| JPS6025277B2 (ja) * | 1979-06-18 | 1985-06-17 | 三井東圧化学株式会社 | 感熱記録シ−ト |
| CH656580A5 (de) * | 1982-05-17 | 1986-07-15 | Ciba Geigy Ag | Druckempfindliches oder waermeempfindliches aufzeichnungsmaterial. |
-
1970
- 1970-12-26 JP JP45118978A patent/JPS521329B1/ja active Pending
-
1971
- 1971-12-08 AU AU36606/71A patent/AU465050B2/en not_active Expired
- 1971-12-13 ES ES397920A patent/ES397920A1/es not_active Expired
- 1971-12-14 CA CA130,059A patent/CA948496A/en not_active Expired
- 1971-12-16 US US00208894A patent/US3834929A/en not_active Expired - Lifetime
- 1971-12-17 IE IE1606/71A patent/IE36855B1/xx unknown
- 1971-12-22 GB GB5975671A patent/GB1350011A/en not_active Expired
- 1971-12-22 DE DE19712163905 patent/DE2163905A1/de active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4348234A (en) * | 1979-03-20 | 1982-09-07 | Ciba-Geigy Corporation | Coating compositions for the production of a recording material |
| US4453744A (en) * | 1981-06-15 | 1984-06-12 | Ciba-Geigy Corporation | Pressure-sensitive or heat-sensitive recording material |
| US4536779A (en) * | 1982-12-10 | 1985-08-20 | Ciba-Geigy Corporation | Heat-sensitive recording material |
| US4556687A (en) * | 1984-03-19 | 1985-12-03 | The Standard Register Company | Color developer for pressure-sensitive recording papers |
| US4614757A (en) * | 1984-03-19 | 1986-09-30 | The Standard Register Company | Color developer for pressure-sensitive recording papers |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1350011A (en) | 1974-04-18 |
| AU3660671A (en) | 1973-06-14 |
| CA948496A (en) | 1974-06-04 |
| IE36855B1 (en) | 1977-03-16 |
| IE36855L (en) | 1972-06-26 |
| ES397920A1 (es) | 1974-06-16 |
| DE2163905A1 (de) | 1972-07-27 |
| JPS521329B1 (enrdf_load_stackoverflow) | 1977-01-13 |
| AU465050B2 (en) | 1975-09-18 |
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