DE2611600C2 - Spirodipyrane und deren Verwendung - Google Patents
Spirodipyrane und deren VerwendungInfo
- Publication number
- DE2611600C2 DE2611600C2 DE2611600A DE2611600A DE2611600C2 DE 2611600 C2 DE2611600 C2 DE 2611600C2 DE 2611600 A DE2611600 A DE 2611600A DE 2611600 A DE2611600 A DE 2611600A DE 2611600 C2 DE2611600 C2 DE 2611600C2
- Authority
- DE
- Germany
- Prior art keywords
- formula
- phenyl
- green
- parts
- compounds
- 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
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 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 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 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 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 150000002780 morpholines Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000002378 acidificating effect Effects 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 description 7
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- KURCTZNCAHYQOV-UHFFFAOYSA-N 4-(dimethylamino)-2-hydroxybenzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C(O)=C1 KURCTZNCAHYQOV-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- -1 N-substituted p-aminosalicylaldehydes Chemical class 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- XFVZSRRZZNLWBW-UHFFFAOYSA-N 4-(Diethylamino)salicylaldehyde Chemical compound CCN(CC)C1=CC=C(C=O)C(O)=C1 XFVZSRRZZNLWBW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 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 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- SKIKINWJMLIFFY-UHFFFAOYSA-N 4-(dibenzylamino)-2-hydroxybenzaldehyde Chemical compound C1=C(C=O)C(O)=CC(N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=C1 SKIKINWJMLIFFY-UHFFFAOYSA-N 0.000 description 2
- YTDCDFCXYVCDHJ-UHFFFAOYSA-N 4-nonylcyclohexan-1-one Chemical compound CCCCCCCCCC1CCC(=O)CC1 YTDCDFCXYVCDHJ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- JPBGLQJDCUZXEF-UHFFFAOYSA-N chromenylium Chemical class [O+]1=CC=CC2=CC=CC=C21 JPBGLQJDCUZXEF-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- YKFKEYKJGVSEIX-UHFFFAOYSA-N cyclohexanone, 4-(1,1-dimethylethyl)- Chemical compound CC(C)(C)C1CCC(=O)CC1 YKFKEYKJGVSEIX-UHFFFAOYSA-N 0.000 description 2
- RAJPIHSBBBWXKQ-UHFFFAOYSA-N dimethyl-(2-methyl-3-phenylchromen-7-ylidene)azanium Chemical class CC1=[O+]C2=CC(N(C)C)=CC=C2C=C1C1=CC=CC=C1 RAJPIHSBBBWXKQ-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000003094 microcapsule Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JQCVPZXMGXKNOD-UHFFFAOYSA-N 1,2-dibenzylbenzene Chemical class C=1C=CC=C(CC=2C=CC=CC=2)C=1CC1=CC=CC=C1 JQCVPZXMGXKNOD-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- JGWOEGYSIHGQPF-UHFFFAOYSA-N 2-morpholin-4-yloxybenzaldehyde Chemical compound O=CC1=CC=CC=C1ON1CCOCC1 JGWOEGYSIHGQPF-UHFFFAOYSA-N 0.000 description 1
- KWKVXXLKBRCPLR-UHFFFAOYSA-N 4-dodecylcyclohexan-1-one Chemical compound CCCCCCCCCCCCC1CCC(=O)CC1 KWKVXXLKBRCPLR-UHFFFAOYSA-N 0.000 description 1
- QWHCPRHASHNSDA-UHFFFAOYSA-N 4-heptylcyclohexan-1-one Chemical compound CCCCCCCC1CCC(=O)CC1 QWHCPRHASHNSDA-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229960000892 attapulgite Drugs 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
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001789 chalcones Chemical class 0.000 description 1
- 235000005513 chalcones Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- CLDTXTVNZMTCPF-UHFFFAOYSA-N dibenzyl-(2-methyl-3-phenylchromen-7-ylidene)azanium Chemical class CC1=[O+]C=2C=C(N(CC=3C=CC=CC=3)CC=3C=CC=CC=3)C=CC=2C=C1C1=CC=CC=C1 CLDTXTVNZMTCPF-UHFFFAOYSA-N 0.000 description 1
- XNYYRGPKZNBVES-UHFFFAOYSA-N diethyl-(2-methyl-3-phenylchromen-7-ylidene)azanium Chemical class CC1=[O+]C2=CC(N(CC)CC)=CC=C2C=C1C1=CC=CC=C1 XNYYRGPKZNBVES-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- FRVCGRDGKAINSV-UHFFFAOYSA-L iron(2+);octadecanoate Chemical compound [Fe+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O FRVCGRDGKAINSV-UHFFFAOYSA-L 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 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 1
- 238000002372 labelling Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004309 pyranyl group Chemical class O1C(C=CC=C1)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
-
- 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
- B41M5/136—Organic colour formers, e.g. leuco dyes
- B41M5/15—Spiro-pyrans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Color Printing (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2611600A DE2611600C2 (de) | 1976-03-19 | 1976-03-19 | Spirodipyrane und deren Verwendung |
| US05/773,337 US4110348A (en) | 1976-03-19 | 1977-03-01 | 7,7'-Diamino derivatives of 2,2'-spirodibenzopyranes |
| CH328177A CH625523A5 (enExample) | 1976-03-19 | 1977-03-16 | |
| FR7707966A FR2344559A1 (fr) | 1976-03-19 | 1977-03-17 | Spirobipyrannes. precurseurs de colorant pour procedes de reproduction |
| GB11541/77A GB1569472A (en) | 1976-03-19 | 1977-03-18 | Spirodipyran dye intermediates for copying processes |
| US05/894,095 US4316027A (en) | 1976-03-19 | 1978-04-06 | 7,7'-Diamino derivatives of 2,2'-spirodibenzopyranes |
| US06/229,651 US4345073A (en) | 1976-03-19 | 1981-01-29 | 7,7'-Diamino derivatives of 2,2'-spirodibenzopyranes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2611600A DE2611600C2 (de) | 1976-03-19 | 1976-03-19 | Spirodipyrane und deren Verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2611600A1 DE2611600A1 (de) | 1977-09-22 |
| DE2611600C2 true DE2611600C2 (de) | 1986-12-18 |
Family
ID=5972868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2611600A Expired DE2611600C2 (de) | 1976-03-19 | 1976-03-19 | Spirodipyrane und deren Verwendung |
Country Status (5)
| Country | Link |
|---|---|
| US (3) | US4110348A (enExample) |
| CH (1) | CH625523A5 (enExample) |
| DE (1) | DE2611600C2 (enExample) |
| FR (1) | FR2344559A1 (enExample) |
| GB (1) | GB1569472A (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2611600C2 (de) * | 1976-03-19 | 1986-12-18 | Basf Ag, 6700 Ludwigshafen | Spirodipyrane und deren Verwendung |
| DE2737207A1 (de) * | 1977-08-18 | 1979-03-01 | Basf Ag | Farbbildner fuer kopierverfahren |
| DE2847690A1 (de) * | 1978-11-03 | 1980-05-22 | Basf Ag | Farbbildner fuer kopierverfahren |
| US4342696A (en) * | 1980-10-08 | 1982-08-03 | Armstrong World Industries, Inc. | 7-Dimethylamino-3-substituted-2,2'-spirobi[2H-1-benzopyrans] |
| US4348508A (en) * | 1981-06-25 | 1982-09-07 | Armstrong World Industries, Inc. | 3-Substituted-7-alkoxy-2,2'-Spirobi[2H-1-benzopyrans] |
| US4382134A (en) * | 1981-10-22 | 1983-05-03 | Armstrong World Industries, Inc. | 3-Substituted-7-alkoxy-spiro(2H-1-benzopyran-2,3'-(3H)-naphtho(2,1-B)pyrans) |
| US4384094A (en) * | 1981-10-22 | 1983-05-17 | Armstrong World Industries, Inc. | 3-Substituted-7-dialkylamino-spiro(2H-1-benzopyran-2,3'-(3H)-naphtha(2,1-b)pyrans) |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL252815A (enExample) * | 1959-06-19 | |||
| NL125655C (enExample) * | 1959-07-15 | |||
| JPS4833712B1 (enExample) * | 1969-05-26 | 1973-10-16 | ||
| GB1359472A (en) * | 1970-09-01 | 1974-07-10 | Agfa Gevaert | Photographic recording and reproduction of information |
| DD109871A5 (enExample) * | 1972-07-01 | 1974-11-20 | ||
| DE2323803C3 (de) * | 1973-05-11 | 1983-12-01 | Basf Ag, 6700 Ludwigshafen | Spirodipyrane und deren Verwendung als Farbbildner für Kopierverfahren |
| DE2430568C3 (de) * | 1974-06-26 | 1979-02-08 | Basf Ag, 6700 Ludwigshafen | Spirodipyrane und deren Verwendung als Farbbildner für druckempfindliche Aufzeichnungsmaterialien |
| DE2611600C2 (de) * | 1976-03-19 | 1986-12-18 | Basf Ag, 6700 Ludwigshafen | Spirodipyrane und deren Verwendung |
| DE2737207A1 (de) * | 1977-08-18 | 1979-03-01 | Basf Ag | Farbbildner fuer kopierverfahren |
-
1976
- 1976-03-19 DE DE2611600A patent/DE2611600C2/de not_active Expired
-
1977
- 1977-03-01 US US05/773,337 patent/US4110348A/en not_active Expired - Lifetime
- 1977-03-16 CH CH328177A patent/CH625523A5/de not_active IP Right Cessation
- 1977-03-17 FR FR7707966A patent/FR2344559A1/fr active Granted
- 1977-03-18 GB GB11541/77A patent/GB1569472A/en not_active Expired
-
1978
- 1978-04-06 US US05/894,095 patent/US4316027A/en not_active Expired - Lifetime
-
1981
- 1981-01-29 US US06/229,651 patent/US4345073A/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| Zur Einsicht für jedermann ist bereitzuhalten: 1 Versuchsbericht, eingeg. am 15.02.84 |
Also Published As
| Publication number | Publication date |
|---|---|
| US4110348A (en) | 1978-08-29 |
| GB1569472A (en) | 1980-06-18 |
| FR2344559B1 (enExample) | 1982-06-04 |
| US4316027A (en) | 1982-02-16 |
| DE2611600A1 (de) | 1977-09-22 |
| FR2344559A1 (fr) | 1977-10-14 |
| US4345073A (en) | 1982-08-17 |
| CH625523A5 (enExample) | 1981-09-30 |
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| 8110 | Request for examination paragraph 44 | ||
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