GB1363870A - Indicator dyes - Google Patents
Indicator dyesInfo
- Publication number
- GB1363870A GB1363870A GB100874A GB100874A GB1363870A GB 1363870 A GB1363870 A GB 1363870A GB 100874 A GB100874 A GB 100874A GB 100874 A GB100874 A GB 100874A GB 1363870 A GB1363870 A GB 1363870A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- prepared
- dry
- naphthalide
- hydroxynaphthyl
- 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
- 239000000975 dye Substances 0.000 title 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- 238000010992 reflux Methods 0.000 abstract 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 abstract 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 4
- 238000001816 cooling Methods 0.000 abstract 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- GWDGEVHBWRIBPF-UHFFFAOYSA-N 1,6-dihydroxynaphthalene-2-carboxylic acid Chemical compound C1=C(O)C=CC2=C(O)C(C(=O)O)=CC=C21 GWDGEVHBWRIBPF-UHFFFAOYSA-N 0.000 abstract 2
- SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical class C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 abstract 2
- HZAMBLFVFWGWSW-UHFFFAOYSA-N 1-hydroxy-6-octadecoxynaphthalene-2-carboxylic acid Chemical compound OC1=C(C(O)=O)C=CC2=CC(OCCCCCCCCCCCCCCCCCC)=CC=C21 HZAMBLFVFWGWSW-UHFFFAOYSA-N 0.000 abstract 2
- WBWRHQJTPUYGFL-UHFFFAOYSA-N 1-hydroxy-n-propylnaphthalene-2-sulfonamide Chemical compound C1=CC=CC2=C(O)C(S(=O)(=O)NCCC)=CC=C21 WBWRHQJTPUYGFL-UHFFFAOYSA-N 0.000 abstract 2
- BGDWGIMWXKYYOG-UHFFFAOYSA-N 1-hydroxynaphthalene-2-carbonyl chloride Chemical compound C1=CC=C2C(O)=C(C(Cl)=O)C=CC2=C1 BGDWGIMWXKYYOG-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 238000001914 filtration Methods 0.000 abstract 2
- 239000007789 gas Substances 0.000 abstract 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 abstract 2
- WSULSMOGMLRGKU-UHFFFAOYSA-N 1-bromooctadecane Chemical compound CCCCCCCCCCCCCCCCCCBr WSULSMOGMLRGKU-UHFFFAOYSA-N 0.000 abstract 1
- UATHVJAINRSNGJ-UHFFFAOYSA-N 1-hydroxy-2-methyl-2h-naphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(O)=O)(O)C(C)C=CC2=C1 UATHVJAINRSNGJ-UHFFFAOYSA-N 0.000 abstract 1
- -1 4 - hydroxynaphthyl Chemical group 0.000 abstract 1
- HLHDIWAOQIRETC-UHFFFAOYSA-N 8-formylnaphthalene-1-carboxylic acid Chemical compound C1=CC(C=O)=C2C(C(=O)O)=CC=CC2=C1 HLHDIWAOQIRETC-UHFFFAOYSA-N 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- 239000002198 insoluble material Substances 0.000 abstract 1
- UVDCQQQGPORSQT-UHFFFAOYSA-N methyl 2-chlorosulfonylnaphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=C(S(Cl)(=O)=O)C=CC2=C1 UVDCQQQGPORSQT-UHFFFAOYSA-N 0.000 abstract 1
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 238000009738 saturating Methods 0.000 abstract 1
- 239000002002 slurry Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C8/00—Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
- G03C8/42—Structural details
- G03C8/44—Integral units, i.e. the image-forming section not being separated from the image-receiving section
- G03C8/48—Integral units, i.e. the image-forming section not being separated from the image-receiving section characterised by substances used for masking the image-forming section
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/06—Hydroxy derivatives of triarylmethanes in which at least one OH group is bound to an aryl nucleus and their ethers or esters
- C09B11/08—Phthaleins; Phenolphthaleins; Fluorescein
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
- C09B11/245—Phthaleins having both OH and amino substituent(s) on aryl ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/26—Triarylmethane dyes in which at least one of the aromatic nuclei is heterocyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Optical Filters (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4378270A | 1970-06-05 | 1970-06-05 | |
| US10339271A | 1971-01-04 | 1971-01-04 | |
| US00103864A US3833615A (en) | 1970-06-05 | 1971-01-04 | Naphthalides and phthalides |
| US00103865A US3833614A (en) | 1970-06-05 | 1971-01-04 | Phthalides and naphthalides |
| US10827771A | 1971-01-21 | 1971-01-21 | |
| US10826071A | 1971-01-21 | 1971-01-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1363870A true GB1363870A (en) | 1974-08-21 |
Family
ID=27556456
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1798971A Expired GB1363864A (en) | 1970-06-05 | 1971-05-28 | Photographic products and development processes |
| GB1799671A Expired GB1363866A (en) | 1970-06-05 | 1971-05-28 | Photographic products and development processes |
| GB100874A Expired GB1363870A (en) | 1970-06-05 | 1971-05-28 | Indicator dyes |
| GB1799471A Expired GB1363865A (en) | 1970-06-05 | 1971-05-28 | Photographic products and diffusion transfer processes |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1798971A Expired GB1363864A (en) | 1970-06-05 | 1971-05-28 | Photographic products and development processes |
| GB1799671A Expired GB1363866A (en) | 1970-06-05 | 1971-05-28 | Photographic products and development processes |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1799471A Expired GB1363865A (en) | 1970-06-05 | 1971-05-28 | Photographic products and diffusion transfer processes |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US3833614A (enExample) |
| AT (1) | AT322979B (enExample) |
| BE (3) | BE768108R (enExample) |
| CA (3) | CA973416A (enExample) |
| CH (1) | CH616008A5 (enExample) |
| DE (3) | DE2165998A1 (enExample) |
| FR (3) | FR2111648B2 (enExample) |
| GB (4) | GB1363864A (enExample) |
| NL (3) | NL169110C (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001290A1 (en) * | 1977-09-23 | 1979-04-04 | Polaroid Corporation | Substituted 2,3-dihydrobenz-(d)-isothiazole-1,1-dioxides and 2,3-dihydronaphtho-(1,8-de)-1,2-thiazine-1,1-dioxides |
| WO1993004403A1 (en) * | 1991-08-20 | 1993-03-04 | Polaroid Corporation | Photographic products and processes |
| US5244771A (en) * | 1991-08-20 | 1993-09-14 | Polaroid Corporation | Photographic products and processes |
| US5294375A (en) * | 1991-08-20 | 1994-03-15 | Polaroid Corporation | Thermochromic materials |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3816123A (en) * | 1971-11-26 | 1974-06-11 | Polaroid Corp | Photographic processes and products employing 8-quinolinol phthaleins as optical filter agents |
| US3976662A (en) * | 1971-11-26 | 1976-08-24 | Polaroid Corporation | 1:1 Adducts of 1-naphthol and (Na)phthalaldehydic acid |
| US4010168A (en) * | 1971-12-02 | 1977-03-01 | Polaroid Corporation | Naphthalide indicator dyes |
| US3923519A (en) * | 1972-01-03 | 1975-12-02 | Polaroid Corp | U.V. light absorbers in supports of integral diffusion transfer film units |
| US4025682A (en) * | 1972-10-24 | 1977-05-24 | Polaroid Corporation | Photographic products |
| US4035391A (en) * | 1974-02-28 | 1977-07-12 | Polaroid Corporation | Phthalide and naphthalide derivatives |
| US4139381A (en) * | 1977-09-23 | 1979-02-13 | Polaroid Corporation | Photographic products and processes employing pH sensitive filter dyes |
| AU523247B2 (en) * | 1977-09-23 | 1982-07-22 | Polaroid Corp. | Sulfam(na)phthalein derivatives |
| US4456674A (en) * | 1982-11-01 | 1984-06-26 | Polaroid Corporation | Color transfer photographic processes and products |
| US4496651A (en) * | 1983-07-25 | 1985-01-29 | Polaroid Corporation | Color transfer photographic processes and products |
| US4615966A (en) * | 1985-07-03 | 1986-10-07 | Polaroid Corporation | Color transfer photographic processes and products with indole phthalein filter dyes |
| US4891298A (en) * | 1988-10-03 | 1990-01-02 | Polaroid Corporation | Photographic products and processes |
| US4886733A (en) * | 1988-10-03 | 1989-12-12 | Polaroid Corporation | Photographic products and processes |
| US5384411A (en) * | 1991-06-20 | 1995-01-24 | Hewlett-Packard Company | Immobilization of PH-sensitive dyes to solid supports |
| US6541177B1 (en) | 2001-04-16 | 2003-04-01 | Polaroid Corporatiion | Diffusion transfer photographic film unit |
| SG11201607444VA (en) * | 2014-03-13 | 2016-10-28 | Mitsubishi Gas Chemical Co | Compound, resin, material for forming underlayer film for lithography, underlayer film for lithography, pattern forming method, and method for purifying the compound or resin |
| SG11201607443XA (en) | 2014-03-13 | 2016-10-28 | Mitsubishi Gas Chemical Co | Resist composition and method for forming resist pattern |
| KR102643950B1 (ko) | 2015-03-30 | 2024-03-07 | 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 | 화합물, 수지, 및 이들의 정제방법, 리소그래피용 하층막 형성재료, 하층막 형성용 조성물, 및 하층막, 그리고, 레지스트패턴 형성방법, 및 회로패턴 형성방법 |
| WO2016158458A1 (ja) | 2015-03-30 | 2016-10-06 | 三菱瓦斯化学株式会社 | レジスト基材、レジスト組成物及びレジストパターン形成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3491112A (en) * | 1967-01-30 | 1970-01-20 | Ncr Co | 3-(phenyl)-3-(heterocyclic-substituted)-phthalides |
| US3509174A (en) * | 1967-01-30 | 1970-04-28 | Ncr Co | 3-(indol-3-yl)-phthalides |
-
1971
- 1971-01-04 US US00103865A patent/US3833614A/en not_active Expired - Lifetime
- 1971-01-04 US US00103864A patent/US3833615A/en not_active Expired - Lifetime
- 1971-01-04 US US103392A patent/US3702245A/en not_active Expired - Lifetime
- 1971-05-28 GB GB1798971A patent/GB1363864A/en not_active Expired
- 1971-05-28 GB GB1799671A patent/GB1363866A/en not_active Expired
- 1971-05-28 GB GB100874A patent/GB1363870A/en not_active Expired
- 1971-05-28 GB GB1799471A patent/GB1363865A/en not_active Expired
- 1971-06-03 CH CH806471A patent/CH616008A5/de not_active IP Right Cessation
- 1971-06-04 BE BE768108A patent/BE768108R/fr active
- 1971-06-04 CA CA114,885A patent/CA973416A/en not_active Expired
- 1971-06-04 DE DE19712165998 patent/DE2165998A1/de active Granted
- 1971-06-04 FR FR717120370A patent/FR2111648B2/fr not_active Expired
- 1971-06-04 BE BE768107A patent/BE768107A/fr not_active IP Right Cessation
- 1971-06-04 BE BE768109A patent/BE768109A/fr not_active IP Right Cessation
- 1971-06-04 FR FR717120372A patent/FR2094079B1/fr not_active Expired
- 1971-06-04 CA CA114,884A patent/CA953731A/en not_active Expired
- 1971-06-04 AT AT488471A patent/AT322979B/de not_active IP Right Cessation
- 1971-06-04 DE DE19712127818 patent/DE2127818A1/de not_active Withdrawn
- 1971-06-04 FR FR717120371A patent/FR2094078B1/fr not_active Expired
- 1971-06-04 CA CA114,883A patent/CA953730A/en not_active Expired
- 1971-06-04 DE DE2166141A patent/DE2166141C3/de not_active Expired
- 1971-06-07 NL NLAANVRAGE7107765,A patent/NL169110C/xx not_active IP Right Cessation
- 1971-06-07 NL NLAANVRAGE7107766,A patent/NL169111C/xx not_active IP Right Cessation
- 1971-06-07 NL NLAANVRAGE7107767,A patent/NL168958C/xx not_active IP Right Cessation
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001290A1 (en) * | 1977-09-23 | 1979-04-04 | Polaroid Corporation | Substituted 2,3-dihydrobenz-(d)-isothiazole-1,1-dioxides and 2,3-dihydronaphtho-(1,8-de)-1,2-thiazine-1,1-dioxides |
| WO1993004403A1 (en) * | 1991-08-20 | 1993-03-04 | Polaroid Corporation | Photographic products and processes |
| US5244771A (en) * | 1991-08-20 | 1993-09-14 | Polaroid Corporation | Photographic products and processes |
| US5294375A (en) * | 1991-08-20 | 1994-03-15 | Polaroid Corporation | Thermochromic materials |
| US6103912A (en) * | 1991-08-20 | 2000-08-15 | Polaroid Corporation | Photographic products and processes |
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE20 | Patent expired after termination of 20 years |