CA2005249A1 - Revelateur chromogene pour papier a pression - Google Patents

Revelateur chromogene pour papier a pression

Info

Publication number: CA2005249A1
Authority: CA; Canada
Prior art keywords: group; parts; resins; color; acid
Prior art date: 1989-03-17
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.): Abandoned

Application number

CA002005249A

Other languages

English (en)

Inventor

Yukio Saeki

Yukio Tokunaga

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sumitomo Durez Co Ltd

Original Assignee

Sumitomo Durez Co Ltd

Priority date (The priority date 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 date listed.)

1989-03-17

Filing date

1989-12-12

Publication date

1991-06-12

1989-03-17 Priority claimed from JP1063946A external-priority patent/JPH02243384A/ja

1989-12-12 Application filed by Sumitomo Durez Co Ltd filed Critical Sumitomo Durez Co Ltd

1989-12-12 Priority to CA002005249A priority Critical patent/CA2005249A1/fr

1991-06-12 Publication of CA2005249A1 publication Critical patent/CA2005249A1/fr

Status Abandoned legal-status Critical Current

Links

239000007859 condensation product Substances 0.000 claims abstract description 54
229920005989 resin Polymers 0.000 claims abstract description 49
239000011347 resin Substances 0.000 claims abstract description 49
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims abstract description 40
229910052751 metal Inorganic materials 0.000 claims abstract description 28
239000002184 metal Substances 0.000 claims abstract description 28
150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 22
150000003839 salts Chemical class 0.000 claims abstract description 22
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims abstract description 20
229960004889 salicylic acid Drugs 0.000 claims abstract description 20
239000003208 petroleum Substances 0.000 claims abstract description 17
239000003054 catalyst Substances 0.000 claims abstract description 13
150000003505 terpenes Chemical class 0.000 claims abstract description 13
235000007586 terpenes Nutrition 0.000 claims abstract description 13
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims abstract description 12
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
230000002378 acidificating effect Effects 0.000 claims abstract description 6
150000001907 coumarones Chemical class 0.000 claims abstract description 5
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 36
-1 tert-octyl group Chemical group 0.000 claims description 25
239000000203 mixture Substances 0.000 claims description 21
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 18
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 12
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 10
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 10
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 10
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 9
150000003870 salicylic acids Chemical class 0.000 claims description 8
229940078552 o-xylene Drugs 0.000 claims description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 4
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
150000002815 nickel Chemical class 0.000 claims description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
229910052782 aluminium Inorganic materials 0.000 claims description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
229910052718 tin Inorganic materials 0.000 claims description 3
229910052725 zinc Inorganic materials 0.000 claims description 3
239000011701 zinc Substances 0.000 claims description 3
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
229910052759 nickel Inorganic materials 0.000 claims description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 38
238000010186 staining Methods 0.000 abstract description 11
238000005562 fading Methods 0.000 abstract description 10
239000000123 paper Substances 0.000 description 31
230000015572 biosynthetic process Effects 0.000 description 25
238000003786 synthesis reaction Methods 0.000 description 25
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
150000001299 aldehydes Chemical class 0.000 description 15
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
239000002253 acid Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
150000003751 zinc Chemical class 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
239000003921 oil Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
238000005292 vacuum distillation Methods 0.000 description 8
229930040373 Paraformaldehyde Natural products 0.000 description 7
229910021626 Tin(II) chloride Inorganic materials 0.000 description 7
229920002866 paraformaldehyde Polymers 0.000 description 7
238000010992 reflux Methods 0.000 description 7
239000000243 solution Substances 0.000 description 7
239000002775 capsule Substances 0.000 description 6
238000009833 condensation Methods 0.000 description 6
238000000034 method Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
MFSJUURIAOOSJR-UHFFFAOYSA-N 2-hydroxy-5-(2,4,4-trimethylpentan-2-yl)benzoic acid Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(C(O)=O)=C1 MFSJUURIAOOSJR-UHFFFAOYSA-N 0.000 description 5
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
239000004927 clay Substances 0.000 description 5
239000005011 phenolic resin Substances 0.000 description 5
150000002989 phenols Chemical class 0.000 description 5
UIYCTSSRJGECEM-UHFFFAOYSA-N 2-hydroxy-5-nonylbenzoic acid Chemical compound CCCCCCCCCC1=CC=C(O)C(C(O)=O)=C1 UIYCTSSRJGECEM-UHFFFAOYSA-N 0.000 description 4
WJWGOUKTYBNQCE-UHFFFAOYSA-N 5-butan-2-yl-2-hydroxybenzoic acid Chemical compound CCC(C)C1=CC=C(O)C(C(O)=O)=C1 WJWGOUKTYBNQCE-UHFFFAOYSA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000007789 gas Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
239000005995 Aluminium silicate Substances 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
235000012211 aluminium silicate Nutrition 0.000 description 3
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
239000001023 inorganic pigment Substances 0.000 description 3
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000000178 monomer Substances 0.000 description 3
230000001590 oxidative effect Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
230000009257 reactivity Effects 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
ILAVGRQKVQRDSF-UHFFFAOYSA-N 2,5-dimethylbenzaldehyde;5-dodecyl-2-hydroxybenzoic acid Chemical compound CC1=CC=C(C)C(C=O)=C1.CCCCCCCCCCCCC1=CC=C(O)C(C(O)=O)=C1 ILAVGRQKVQRDSF-UHFFFAOYSA-N 0.000 description 2
VGRSGGWEMWFPEQ-UHFFFAOYSA-N 2,6-dimethylbenzaldehyde;2-hydroxy-5-nonylbenzoic acid Chemical compound CC1=CC=CC(C)=C1C=O.CCCCCCCCCC1=CC=C(O)C(C(O)=O)=C1 VGRSGGWEMWFPEQ-UHFFFAOYSA-N 0.000 description 2
ZJWUEJOPKFYFQD-UHFFFAOYSA-N 2-hydroxy-3-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1O ZJWUEJOPKFYFQD-UHFFFAOYSA-N 0.000 description 2
LGERKUYJCZOBTB-UHFFFAOYSA-N 2-hydroxy-5-phenylbenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(C=2C=CC=CC=2)=C1 LGERKUYJCZOBTB-UHFFFAOYSA-N 0.000 description 2
GWPIMQIVMAYPQW-UHFFFAOYSA-N 2-hydroxybenzoic acid;2-methylbenzaldehyde Chemical compound CC1=CC=CC=C1C=O.OC(=O)C1=CC=CC=C1O GWPIMQIVMAYPQW-UHFFFAOYSA-N 0.000 description 2
AFIMKCDXMUVHON-UHFFFAOYSA-N 5-benzyl-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(CC=2C=CC=CC=2)=C1 AFIMKCDXMUVHON-UHFFFAOYSA-N 0.000 description 2
AKRXNODXDXYTQL-UHFFFAOYSA-N 5-dodecyl-2-hydroxybenzoic acid Chemical compound CCCCCCCCCCCCC1=CC=C(O)C(C(O)=O)=C1 AKRXNODXDXYTQL-UHFFFAOYSA-N 0.000 description 2
XAICWTLLSRXZPB-UHFFFAOYSA-N 5-tert-butyl-2-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC=C(O)C(C(O)=O)=C1 XAICWTLLSRXZPB-UHFFFAOYSA-N 0.000 description 2
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
MMPOTNFPDMJTRR-UHFFFAOYSA-N OOOOOOOOOOO Chemical compound OOOOOOOOOOO MMPOTNFPDMJTRR-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
229910021536 Zeolite Inorganic materials 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
235000012538 ammonium bicarbonate Nutrition 0.000 description 2
239000001099 ammonium carbonate Substances 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
238000007334 copolymerization reaction Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
235000019256 formaldehyde Nutrition 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000003094 microcapsule Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 2
239000002245 particle Substances 0.000 description 2
229920001568 phenolic resin Polymers 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
238000010998 test method Methods 0.000 description 2
FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
239000008096 xylene Substances 0.000 description 2
239000010457 zeolite Substances 0.000 description 2
239000011592 zinc chloride Substances 0.000 description 2
235000005074 zinc chloride Nutrition 0.000 description 2
WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 description 1
BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
IIEJGTQVBJHMDL-UHFFFAOYSA-N 2-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-5-[2-oxo-2-[3-(sulfamoylamino)pyrrolidin-1-yl]ethyl]-1,3,4-oxadiazole Chemical group C1CN(CC1NS(=O)(=O)N)C(=O)CC2=NN=C(O2)C3=CN=C(N=C3)NC4CC5=CC=CC=C5C4 IIEJGTQVBJHMDL-UHFFFAOYSA-N 0.000 description 1
KWIPUXXIFQQMKN-UHFFFAOYSA-N 2-azaniumyl-3-(4-cyanophenyl)propanoate Chemical compound OC(=O)C(N)CC1=CC=C(C#N)C=C1 KWIPUXXIFQQMKN-UHFFFAOYSA-N 0.000 description 1
PQLFCHDUACQEPJ-UHFFFAOYSA-N 2-hydroxy-3-(2,4,4-trimethylpentan-2-yl)benzoic acid Chemical compound CC(C)(C)CC(C)(C)C1=CC=CC(C(O)=O)=C1O PQLFCHDUACQEPJ-UHFFFAOYSA-N 0.000 description 1
ZIHNKVLRTWFXPA-UHFFFAOYSA-N 2-hydroxy-3-nonylbenzoic acid Chemical compound CCCCCCCCCC1=CC=CC(C(O)=O)=C1O ZIHNKVLRTWFXPA-UHFFFAOYSA-N 0.000 description 1
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
YUVVASYGZFERRP-UHFFFAOYSA-N 3-benzyl-2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(CC=2C=CC=CC=2)=C1O YUVVASYGZFERRP-UHFFFAOYSA-N 0.000 description 1
RVFNONSGQDLXJW-UHFFFAOYSA-N 3-butan-2-yl-2-hydroxybenzoic acid Chemical compound CCC(C)C1=CC=CC(C(O)=O)=C1O RVFNONSGQDLXJW-UHFFFAOYSA-N 0.000 description 1
SIFDSJCMINUPDM-UHFFFAOYSA-N 3-dodecyl-2-hydroxybenzoic acid Chemical compound CCCCCCCCCCCCC1=CC=CC(C(O)=O)=C1O SIFDSJCMINUPDM-UHFFFAOYSA-N 0.000 description 1
ZAAMQANODYDRDF-UHFFFAOYSA-N 3-tert-butyl-2-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC=CC(C(O)=O)=C1O ZAAMQANODYDRDF-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
MOMKYJPSVWEWPM-UHFFFAOYSA-N 4-(chloromethyl)-2-(4-methylphenyl)-1,3-thiazole Chemical compound C1=CC(C)=CC=C1C1=NC(CCl)=CS1 MOMKYJPSVWEWPM-UHFFFAOYSA-N 0.000 description 1
RVBSIDRJMOSQOR-UHFFFAOYSA-N 5-benzyl-2-hydroxybenzoic acid;2-ethylbenzaldehyde Chemical compound CCC1=CC=CC=C1C=O.C1=C(O)C(C(=O)O)=CC(CC=2C=CC=CC=2)=C1 RVBSIDRJMOSQOR-UHFFFAOYSA-N 0.000 description 1
ZJKLKPARWUFLAP-UHFFFAOYSA-N 5-tert-butyl-2-hydroxybenzoic acid;2,4,6-trimethylbenzaldehyde Chemical compound CC1=CC(C)=C(C=O)C(C)=C1.CC(C)(C)C1=CC=C(O)C(C(O)=O)=C1 ZJKLKPARWUFLAP-UHFFFAOYSA-N 0.000 description 1
VWGJTOFZUOIWLK-UHFFFAOYSA-N C(C1=CC=CC=C1)C=O.C1(=CC=CC=C1)C1=CC=C(C(C(=O)O)=C1)O Chemical compound C(C1=CC=CC=C1)C=O.C1(=CC=CC=C1)C1=CC=C(C(C(=O)O)=C1)O VWGJTOFZUOIWLK-UHFFFAOYSA-N 0.000 description 1
QDBXHHLVSVIZBW-UHFFFAOYSA-N C1(=C(C(=CC=C1)C=O)C)C.C(C=1C(O)=CC=CC1)(=O)O Chemical compound C1(=C(C(=CC=C1)C=O)C)C.C(C=1C(O)=CC=CC1)(=O)O QDBXHHLVSVIZBW-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
238000007065 Kolbe-Schmitt synthesis reaction Methods 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
241000779819 Syncarpia glomulifera Species 0.000 description 1
239000006096 absorbing agent Substances 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229940090948 ammonium benzoate Drugs 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000006254 arylation reaction Methods 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
VHNFAQLOVBWGGB-UHFFFAOYSA-N benzhydrylbenzene;3h-2-benzofuran-1-one Chemical class C1=CC=C2C(=O)OCC2=C1.C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 VHNFAQLOVBWGGB-UHFFFAOYSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
230000021523 carboxylation Effects 0.000 description 1
238000006473 carboxylation reaction Methods 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000002131 composite material Substances 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000011888 foil Substances 0.000 description 1
UMGLBLXWFVODRF-UHFFFAOYSA-N formaldehyde;4-phenylphenol Chemical compound O=C.C1=CC(O)=CC=C1C1=CC=CC=C1 UMGLBLXWFVODRF-UHFFFAOYSA-N 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000007654 immersion Methods 0.000 description 1
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
150000002475 indoles Chemical class 0.000 description 1
239000004816 latex Substances 0.000 description 1
229920000126 latex Polymers 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
LAIZPRYFQUWUBN-UHFFFAOYSA-L nickel chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Ni+2] LAIZPRYFQUWUBN-UHFFFAOYSA-L 0.000 description 1
229920003986 novolac Polymers 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
229940044654 phenolsulfonic acid Drugs 0.000 description 1
150000002990 phenothiazines Chemical class 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
239000001739 pinus spp. Substances 0.000 description 1
239000002985 plastic film Substances 0.000 description 1
229920006255 plastic film Polymers 0.000 description 1
150000003097 polyterpenes Chemical class 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000003825 pressing Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000009877 rendering Methods 0.000 description 1
235000019983 sodium metaphosphate Nutrition 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000004961 triphenylmethanes Chemical class 0.000 description 1
229940036248 turpentine Drugs 0.000 description 1
HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1

Landscapes

Color Printing (AREA)

CA002005249A 1989-03-17 1989-12-12 Revelateur chromogene pour papier a pression Abandoned CA2005249A1 (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA002005249A CA2005249A1 (fr)	1989-03-17	1989-12-12	Revelateur chromogene pour papier a pression

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP1063946A JPH02243384A (ja)	1989-03-17	1989-03-17	感圧記録紙用顕色剤
CA002005249A CA2005249A1 (fr)	1989-03-17	1989-12-12	Revelateur chromogene pour papier a pression

Publications (1)

Publication Number	Publication Date
CA2005249A1 true CA2005249A1 (fr)	1991-06-12

Family

ID=25673829

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002005249A Abandoned CA2005249A1 (fr)	1989-03-17	1989-12-12	Revelateur chromogene pour papier a pression

Country Status (1)

Country	Link
CA (1)	CA2005249A1 (fr)

1989
- 1989-12-12 CA CA002005249A patent/CA2005249A1/fr not_active Abandoned

Legal Events

Date	Code	Title	Description
1993-06-13	FZDE	Discontinued

Publication	Publication Date	Title
US4173684A (en)	1979-11-06	Production of novel metal modified novolak resins and their use in pressure sensitive papers
US4025490A (en)	1977-05-24	Method of producing metal modified phenol-aldehyde novolak resins
US4612254A (en)	1986-09-16	Aromatic carboxylic acid and metal-modified phenolic resins and methods of preparation
US4226962A (en)	1980-10-07	Production of novel metal modified novolak resins and their use in pressure sensitive papers
US4400492A (en)	1983-08-23	Color-developer for pressure-sensitive recording sheets
US4216299A (en)	1980-08-05	Color developer for pressure-sensitive copying paper
US4952648A (en)	1990-08-28	Production process of multivalent metal-modified salicylic acid/styrene resin, color-developing agent using the resin and suited for use in pressure-sensitive copying paper sheet and pressure-sensitive copying paper unit employing the agent
CA1336031C (fr)	1995-06-20	Revelateur de couleurs pour feuilles auto-adhesives et feuilles enduites de ce revelateur
CA1102123A (fr)	1981-06-02	Traduction non-disponible
US4379897A (en)	1983-04-12	Color-developer for pressure-sensitive sheets
US5034370A (en)	1991-07-23	Color developer for pressure-sensitive recording paper
EP0233450B1 (fr)	1992-03-11	Copolymères linéaires d'acide salicylique et leurs sels métalliques, procédé de préparation de ceux-ci, révélateurs de couleur à base de copolymères métalliques et feuilles revêtue d'une telle couche
CA2005249A1 (fr)	1991-06-12	Revelateur chromogene pour papier a pression
US4604436A (en)	1986-08-05	Process for metal modified phenolic novolac resin
US4920185A (en)	1990-04-24	Color developer for pressure-sensitive recording paper and production thereof using a phenol-xylene-formaldehyde resin
US4920186A (en)	1990-04-24	Color developer for pressure sensitive recording paper and production thereof using phenol-mesitylene-formaldehyde resin
EP0338808B1 (fr)	1995-08-23	Résine alkyl salicylate pour papier de copiage sans carbone et son utilisation pour former des images
GB2073226A (en)	1981-10-14	Color-developer for pressure- sensitive recording sheets
JPH0518715B2 (fr)	1993-03-12
JPS6138038B2 (fr)	1986-08-27
GB1564850A (en)	1980-04-16	Producing metal modified phenol-aldehyde novolak resins
JPH0230583A (ja)	1990-01-31	感圧記録紙用顕色剤
JPS63115782A (ja)	1988-05-20	感圧複写紙用顕色シ−ト
JPH0698826B2 (ja)	1994-12-07	感圧複写紙用顕色シ−ト
JPH02255375A (ja)	1990-10-16	感圧記録体用顕色剤、顕色剤の水性分散液およびその製造法