DE2265772C2 - Druckempfindliches Aufzeichnungsmaterial - Google Patents
Druckempfindliches AufzeichnungsmaterialInfo
- Publication number
- DE2265772C2 DE2265772C2 DE2265772A DE2265772A DE2265772C2 DE 2265772 C2 DE2265772 C2 DE 2265772C2 DE 2265772 A DE2265772 A DE 2265772A DE 2265772 A DE2265772 A DE 2265772A DE 2265772 C2 DE2265772 C2 DE 2265772C2
- Authority
- DE
- Germany
- Prior art keywords
- tetrachlorophthalide
- sensitive recording
- recording material
- pressure
- ethyl
- 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
Links
- 239000000463 material Substances 0.000 title claims description 23
- NMWKWBPNKPGATC-UHFFFAOYSA-N 4,5,6,7-tetrachloro-2-benzofuran-1(3H)-one Chemical compound ClC1=C(Cl)C(Cl)=C2COC(=O)C2=C1Cl NMWKWBPNKPGATC-UHFFFAOYSA-N 0.000 claims description 20
- 239000012445 acidic reagent Substances 0.000 claims description 3
- 239000003593 chromogenic compound Substances 0.000 claims 1
- -1 phenyl- Chemical group 0.000 description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 239000005995 Aluminium silicate Substances 0.000 description 8
- 235000012211 aluminium silicate Nutrition 0.000 description 8
- 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 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000005562 fading Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- BJMUOUXGBFNLSN-UHFFFAOYSA-N 1,2-dimethylindole Chemical compound C1=CC=C2N(C)C(C)=CC2=C1 BJMUOUXGBFNLSN-UHFFFAOYSA-N 0.000 description 2
- XMOWAIVXKJWQBJ-UHFFFAOYSA-N 1-ethyl-2-methylindole Chemical compound C1=CC=C2N(CC)C(C)=CC2=C1 XMOWAIVXKJWQBJ-UHFFFAOYSA-N 0.000 description 2
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229960000892 attapulgite Drugs 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
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 2
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052625 palygorskite Inorganic materials 0.000 description 2
- 125000003884 phenylalkyl group Chemical group 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 1
- JYILHMMEEBFSKH-UHFFFAOYSA-N 2,3,4,5-tetrachloro-6-[4-(diethylamino)benzoyl]benzoic acid Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O JYILHMMEEBFSKH-UHFFFAOYSA-N 0.000 description 1
- AGCSOGVTICZFOS-UHFFFAOYSA-N 2,3,4,5-tetrachloro-6-[4-(dimethylamino)benzoyl]benzoic acid Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O AGCSOGVTICZFOS-UHFFFAOYSA-N 0.000 description 1
- GHZPDRVHYHFILK-UHFFFAOYSA-N 3-chloro-3h-2-benzofuran-1-one Chemical compound C1=CC=C2C(Cl)OC(=O)C2=C1 GHZPDRVHYHFILK-UHFFFAOYSA-N 0.000 description 1
- RUQDOHJIVIGFFC-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3-[4-(diethylamino)phenyl]-3-(1-ethyl-2-methylindol-3-yl)-2-benzofuran-1-one Chemical compound C1=CC(N(CC)CC)=CC=C1C1(C=2C3=CC=CC=C3N(CC)C=2C)C(C(Cl)=C(Cl)C(Cl)=C2Cl)=C2C(=O)O1 RUQDOHJIVIGFFC-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
- CYYZDBDROVLTJU-UHFFFAOYSA-N 4-n-Butylphenol Chemical group CCCCC1=CC=C(O)C=C1 CYYZDBDROVLTJU-UHFFFAOYSA-N 0.000 description 1
- VOIWCMWMOYUVSF-UHFFFAOYSA-N CCN(CC)C1=CC=C(C(C2=C(C)N(C)C3=CC=CC=C23)(C(C2=C(C(Cl)=C3Cl)Cl)=C3Cl)OC2=O)C=C1 Chemical compound CCN(CC)C1=CC=C(C(C2=C(C)N(C)C3=CC=CC=C23)(C(C2=C(C(Cl)=C3Cl)Cl)=C3Cl)OC2=O)C=C1 VOIWCMWMOYUVSF-UHFFFAOYSA-N 0.000 description 1
- IPAJDLMMTVZVPP-UHFFFAOYSA-N Crystal violet lactone Chemical compound C1=CC(N(C)C)=CC=C1C1(C=2C=CC(=CC=2)N(C)C)C2=CC=C(N(C)C)C=C2C(=O)O1 IPAJDLMMTVZVPP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940060942 methylin Drugs 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- VIACAIAQHPLINF-UHFFFAOYSA-N n-benzyl-n-ethyl-3-methylaniline Chemical compound C=1C=CC(C)=CC=1N(CC)CC1=CC=CC=C1 VIACAIAQHPLINF-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
- C07D307/885—3,3-Diphenylphthalides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Color Printing (AREA)
- Indole Compounds (AREA)
- Furan Compounds (AREA)
- Photoreceptors In Electrophotography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13795271A | 1971-04-27 | 1971-04-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2265772A1 DE2265772A1 (enExample) | 1982-09-16 |
| DE2265772C2 true DE2265772C2 (de) | 1983-09-22 |
Family
ID=22479769
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2265772A Expired DE2265772C2 (de) | 1971-04-27 | 1972-04-19 | Druckempfindliches Aufzeichnungsmaterial |
| DE2218895A Expired DE2218895C2 (de) | 1971-04-27 | 1972-04-19 | Chromogene Tetrachlorphthalide |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2218895A Expired DE2218895C2 (de) | 1971-04-27 | 1972-04-19 | Chromogene Tetrachlorphthalide |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3736337A (enExample) |
| JP (6) | JPS5525996B1 (enExample) |
| AU (1) | AU459132B2 (enExample) |
| BE (1) | BE782653A (enExample) |
| CA (1) | CA984847A (enExample) |
| CH (1) | CH606276A5 (enExample) |
| DE (2) | DE2265772C2 (enExample) |
| ES (1) | ES402057A1 (enExample) |
| FR (1) | FR2136694A5 (enExample) |
| GB (1) | GB1349503A (enExample) |
| IT (1) | IT954848B (enExample) |
| ZA (1) | ZA722506B (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4102893A (en) * | 1971-11-26 | 1978-07-25 | Ciba-Geigy Ag | Process for the manufacture of color formers of indoles and anhydrides of aromatic or heteroaromatic, vicinal dicarboxylic acids, new color formers of these classes of substance and their use |
| US4186134A (en) * | 1973-05-21 | 1980-01-29 | Ciba-Geigy Corporation | 3-Indolyl-3-phenyl-phthalides |
| GB1460751A (en) * | 1973-05-21 | 1977-01-06 | Ciba Geigy Ag | 3-indolyl-3-phenyl-phthalide compounds their manufacture and their use |
| GB1460151A (en) * | 1973-05-21 | 1976-12-31 | Ciba Geigy | Nitrophthalides their mahufacture and their use in recording systems- |
| GB1467898A (en) * | 1974-04-09 | 1977-03-23 | Ciba Geigy Ag | Heterocyclic substituted lactone compounds their manufacture and use |
| US4016174A (en) * | 1975-04-10 | 1977-04-05 | Ncr Corporation | Benzoindole phthalides |
| US4020056A (en) * | 1975-04-10 | 1977-04-26 | Ncr Corporation | Di-vinyl phthalides color formers |
| US4026883A (en) * | 1975-04-10 | 1977-05-31 | Ncr Corporation | Derivatives of dianhydrides as vinyl color formers |
| CH594511A5 (enExample) * | 1976-01-16 | 1978-01-13 | Ciba Geigy Ag | |
| US4189171A (en) * | 1977-03-01 | 1980-02-19 | Sterling Drug Inc. | Marking systems containing 3-aryl-3-heterylphthalides and 3,3-bis(heteryl)phthalides |
| JPS553804A (en) * | 1978-06-23 | 1980-01-11 | Denpatsu Furaiatsushiyu Kk | Manufacture of granular active substance |
| US4275206A (en) * | 1979-03-05 | 1981-06-23 | Appleton Papers Inc. | Lactone compounds containing an indolizine radical |
| JPS6085986A (ja) * | 1983-10-18 | 1985-05-15 | Yamada Kagaku Kogyo Kk | 発色性記録材料 |
| JPS6216914A (ja) * | 1985-07-12 | 1987-01-26 | Seiko Giken Kk | 粉粒体輸送装置による粉粒体の移送方法 |
| DE3775598D1 (de) * | 1986-04-15 | 1992-02-13 | Yamada Chem Co | Divinylverbindungen und unter verwendung dieser verbindungen hergestelltes chromogenes aufzeichnungsmaterial. |
| EP0242170B1 (en) * | 1986-04-16 | 1991-09-18 | Yamada Chemical Co., Ltd. | Divinyl compounds and chromogenic recording-material prepared by use thereof |
| JPS6367179A (ja) * | 1986-09-08 | 1988-03-25 | Fuji Photo Film Co Ltd | 記録シ−ト |
| JPS6367180A (ja) * | 1986-09-09 | 1988-03-25 | Fuji Photo Film Co Ltd | 記録シ−ト |
| EP0787764B1 (en) * | 1996-02-03 | 2003-04-09 | Mitsubishi Gas Chemical Company, Inc. | Oxygen-absorbing resin composition and packing material, multi-layered packing material, package and packing method using the same |
| CN1212814C (zh) * | 1996-07-02 | 2005-08-03 | 日本巴伊欧尼克斯股份有限公司 | 片状发热体及其制造方法 |
| EP0964046B1 (en) | 1998-06-03 | 2003-07-30 | Mitsubishi Gas Chemical Company, Inc. | Oxygen absorbing composition, oxygen absorbing resin and preserving method |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3491112A (en) * | 1967-01-30 | 1970-01-20 | Ncr Co | 3-(phenyl)-3-(heterocyclic-substituted)-phthalides |
| JPS4833208A (enExample) * | 1971-09-03 | 1973-05-08 | ||
| JPS5127251B2 (enExample) * | 1972-06-02 | 1976-08-11 | ||
| JPS4916727A (enExample) * | 1972-06-03 | 1974-02-14 |
-
1971
- 1971-04-27 US US00137952A patent/US3736337A/en not_active Expired - Lifetime
-
1972
- 1972-03-06 CA CA136,362A patent/CA984847A/en not_active Expired
- 1972-04-13 ZA ZA722506A patent/ZA722506B/xx unknown
- 1972-04-17 AU AU41212/72A patent/AU459132B2/en not_active Expired
- 1972-04-18 GB GB1782072A patent/GB1349503A/en not_active Expired
- 1972-04-19 DE DE2265772A patent/DE2265772C2/de not_active Expired
- 1972-04-19 DE DE2218895A patent/DE2218895C2/de not_active Expired
- 1972-04-19 IT IT23420/72A patent/IT954848B/it active
- 1972-04-25 JP JP4098072A patent/JPS5525996B1/ja active Pending
- 1972-04-25 ES ES0402057A patent/ES402057A1/es not_active Expired
- 1972-04-26 FR FR7214770A patent/FR2136694A5/fr not_active Expired
- 1972-04-26 CH CH616172A patent/CH606276A5/xx not_active IP Right Cessation
- 1972-04-26 BE BE782653A patent/BE782653A/xx not_active IP Right Cessation
-
1979
- 1979-11-09 JP JP54145313A patent/JPS5945516B2/ja not_active Expired
- 1979-11-09 JP JP54145312A patent/JPS5948756B2/ja not_active Expired
- 1979-11-09 JP JP14531479A patent/JPS5633982A/ja active Pending
- 1979-11-09 JP JP14531179A patent/JPS5633979A/ja active Pending
- 1979-11-09 JP JP54145310A patent/JPS5829239B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU459132B2 (en) | 1975-02-26 |
| JPS5633980A (en) | 1981-04-04 |
| FR2136694A5 (enExample) | 1972-12-22 |
| BE782653A (fr) | 1972-08-16 |
| JPS5633981A (en) | 1981-04-04 |
| IT954848B (it) | 1973-09-15 |
| JPS5945516B2 (ja) | 1984-11-07 |
| ZA722506B (en) | 1973-01-31 |
| CH606276A5 (enExample) | 1978-10-31 |
| US3736337A (en) | 1973-05-29 |
| JPS5633978A (en) | 1981-04-04 |
| GB1349503A (en) | 1974-04-03 |
| DE2218895A1 (de) | 1972-11-09 |
| JPS5633982A (en) | 1981-04-04 |
| JPS5633979A (en) | 1981-04-04 |
| DE2265772A1 (enExample) | 1982-09-16 |
| ES402057A1 (es) | 1975-03-16 |
| JPS5948756B2 (ja) | 1984-11-28 |
| DE2218895C2 (de) | 1983-12-08 |
| JPS5525996B1 (enExample) | 1980-07-10 |
| AU4121272A (en) | 1973-10-25 |
| CA984847A (en) | 1976-03-02 |
| JPS5829239B2 (ja) | 1983-06-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| Q172 | Divided out of (supplement): |
Ref country code: DE Ref document number: 2218895 |
|
| 8110 | Request for examination paragraph 44 | ||
| 8181 | Inventor (new situation) |
Free format text: FARBER, SHELDON, APPLETON, WIS., US |
|
| AC | Divided out of |
Ref country code: DE Ref document number: 2218895 Format of ref document f/p: P |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: APPLETON PAPERS INC., APPLETON, WIS., US |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: WEICKMANN, H., DIPL.-ING. FINCKE, K., DIPL.-PHYS. DR. WEICKMANN, F., DIPL.-ING. HUBER, B., DIPL.-CHEM. LISKA, H., DIPL.-ING. DR.-ING. PRECHTEL, J., DIPL.-PHYS. DR.RER.NAT., PAT.-ANW., 8000 MUENCHEN |