DE2259970A1 - Massefaerben von polyestern - Google Patents
Massefaerben von polyesternInfo
- Publication number
- DE2259970A1 DE2259970A1 DE2259970A DE2259970A DE2259970A1 DE 2259970 A1 DE2259970 A1 DE 2259970A1 DE 2259970 A DE2259970 A DE 2259970A DE 2259970 A DE2259970 A DE 2259970A DE 2259970 A1 DE2259970 A1 DE 2259970A1
- Authority
- DE
- Germany
- Prior art keywords
- anthraquinone
- phenylthio
- tetra
- polyester
- red
- 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.)
- Withdrawn
Links
- 229920000728 polyester Polymers 0.000 title claims description 33
- 239000003086 colorant Substances 0.000 title description 4
- 239000000975 dye Substances 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 238000004043 dyeing Methods 0.000 claims description 3
- -1 isutyl Chemical group 0.000 description 23
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 22
- 150000004056 anthraquinones Chemical class 0.000 description 22
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000004040 coloring Methods 0.000 description 5
- 238000009998 heat setting Methods 0.000 description 5
- 229920000139 polyethylene terephthalate Polymers 0.000 description 5
- 239000005020 polyethylene terephthalate Substances 0.000 description 5
- 238000009987 spinning Methods 0.000 description 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- WLEIVDIWTWFRLQ-UHFFFAOYSA-N 1,4,5,8-tetrakis(phenylsulfanyl)anthracene-9,10-dione Chemical compound C1=CC(SC=2C=CC=CC=2)=C2C(=O)C3=C(SC=4C=CC=CC=4)C=CC(SC=4C=CC=CC=4)=C3C(=O)C2=C1SC1=CC=CC=C1 WLEIVDIWTWFRLQ-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- HEEAHTSGNNYQEW-UHFFFAOYSA-N 1,3,5,7-tetrakis(phenylsulfanyl)anthracene-9,10-dione Chemical compound C=1C(SC=2C=CC=CC=2)=C2C(=O)C3=CC(SC=4C=CC=CC=4)=CC(SC=4C=CC=CC=4)=C3C(=O)C2=CC=1SC1=CC=CC=C1 HEEAHTSGNNYQEW-UHFFFAOYSA-N 0.000 description 2
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- XLZXCFHDGWHJOS-UHFFFAOYSA-N 1,4,5-tris(phenylsulfanyl)anthracene-9,10-dione Chemical compound C=12C(=O)C3=C(SC=4C=CC=CC=4)C=CC(SC=4C=CC=CC=4)=C3C(=O)C2=CC=CC=1SC1=CC=CC=C1 XLZXCFHDGWHJOS-UHFFFAOYSA-N 0.000 description 1
- GJCHQJDEYFYWER-UHFFFAOYSA-N 1,8-dihydroxy-4,5-dinitroanthracene-9,10-dione Chemical compound O=C1C2=C([N+]([O-])=O)C=CC(O)=C2C(=O)C2=C1C([N+]([O-])=O)=CC=C2O GJCHQJDEYFYWER-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- FPRGJFFNVANESG-UHFFFAOYSA-N 1-phenylsulfanylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1SC1=CC=CC=C1 FPRGJFFNVANESG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- BTVWZWFKMIUSGS-UHFFFAOYSA-N dimethylethyleneglycol Natural products CC(C)(O)CO BTVWZWFKMIUSGS-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 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 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- WDQHCKFAVZZITG-UHFFFAOYSA-L manganese(2+) phosphoric acid diacetate Chemical compound P(O)(O)(O)=O.C(C)(=O)[O-].[Mn+2].C(C)(=O)[O-] WDQHCKFAVZZITG-UHFFFAOYSA-L 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/375—Thiols containing six-membered aromatic rings
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/02—Hydroxy-anthraquinones; Ethers or esters thereof
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/56—Mercapto-anthraquinones
- C09B1/58—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals
- C09B1/585—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals substituted by aryl radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Coloring (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Artificial Filaments (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2259970A DE2259970A1 (de) | 1972-12-07 | 1972-12-07 | Massefaerben von polyestern |
| IT66010/73A IT1001204B (it) | 1972-12-07 | 1973-12-05 | Colorazione in massa di poliesteri |
| CH1703773A CH584730A5 (enrdf_load_stackoverflow) | 1972-12-07 | 1973-12-05 | |
| JP48135458A JPS5834510B2 (ja) | 1972-12-07 | 1973-12-05 | ポリエステル ノ センシヨクホウホウ |
| BE138575A BE808292A (fr) | 1972-12-07 | 1973-12-06 | Teinture de polyesters dans leur masse |
| GB5657173A GB1402704A (en) | 1972-12-07 | 1973-12-06 | Mass dyeing of polyesters |
| FR7343824A FR2209808B1 (enrdf_load_stackoverflow) | 1972-12-07 | 1973-12-07 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2259970A DE2259970A1 (de) | 1972-12-07 | 1972-12-07 | Massefaerben von polyestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2259970A1 true DE2259970A1 (de) | 1974-06-12 |
Family
ID=5863820
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2259970A Withdrawn DE2259970A1 (de) | 1972-12-07 | 1972-12-07 | Massefaerben von polyestern |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5834510B2 (enrdf_load_stackoverflow) |
| BE (1) | BE808292A (enrdf_load_stackoverflow) |
| CH (1) | CH584730A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2259970A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2209808B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1402704A (enrdf_load_stackoverflow) |
| IT (1) | IT1001204B (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0074523A1 (de) * | 1981-09-05 | 1983-03-23 | Bayer Ag | Flüssigkristallines Material enthaltend Anthrachinonfarbstoffe sowie neue Anthrachinonfarbstoffe |
| DE3314467A1 (de) * | 1982-07-17 | 1984-01-19 | Bayer Ag, 5090 Leverkusen | Dichroitisches material, enthaltend anthrachinonfarbstoffe und neue anthrachinonfarbstoffe |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3276868D1 (de) * | 1981-02-25 | 1987-09-03 | Ici Plc | Pleochroic anthraquinone dyes |
| GB2094822B (en) * | 1981-02-25 | 1986-03-05 | Ici Plc | Anthraquinone dyes |
| US4464282A (en) * | 1981-02-25 | 1984-08-07 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britian And Northern Ireland | Organic materials |
| GB2093475B (en) * | 1981-02-25 | 1985-10-09 | Secr Defence | Liquid crystal materials containing pleochroic dithioanthraquinone dyes |
| US4446047A (en) * | 1981-02-25 | 1984-05-01 | Imperial Chemical Industries Plc | Pleochroic anthraquinone dyes |
| JPS5927956A (ja) * | 1982-07-17 | 1984-02-14 | バイエル・アクチエンゲゼルシヤフト | アントラキノン染料を含む二色性物質及び新規なアントラキノン染料 |
| US7160335B2 (en) | 2002-03-22 | 2007-01-09 | Ciba Specialty Chemicals Corporation | Anthraquinone dyes |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1487044A (fr) * | 1965-07-19 | 1967-06-30 | Ici Ltd | Procédé de coloration dans la masse de polyesters linéaires synthétiques |
| BE755026A (fr) * | 1969-08-20 | 1971-02-01 | Bayer Ag | Procede de teinture en continu de matieres fibreuses synthetiques |
-
1972
- 1972-12-07 DE DE2259970A patent/DE2259970A1/de not_active Withdrawn
-
1973
- 1973-12-05 CH CH1703773A patent/CH584730A5/xx not_active IP Right Cessation
- 1973-12-05 JP JP48135458A patent/JPS5834510B2/ja not_active Expired
- 1973-12-05 IT IT66010/73A patent/IT1001204B/it active
- 1973-12-06 BE BE138575A patent/BE808292A/xx unknown
- 1973-12-06 GB GB5657173A patent/GB1402704A/en not_active Expired
- 1973-12-07 FR FR7343824A patent/FR2209808B1/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0074523A1 (de) * | 1981-09-05 | 1983-03-23 | Bayer Ag | Flüssigkristallines Material enthaltend Anthrachinonfarbstoffe sowie neue Anthrachinonfarbstoffe |
| DE3314467A1 (de) * | 1982-07-17 | 1984-01-19 | Bayer Ag, 5090 Leverkusen | Dichroitisches material, enthaltend anthrachinonfarbstoffe und neue anthrachinonfarbstoffe |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1402704A (en) | 1975-08-13 |
| JPS5834510B2 (ja) | 1983-07-27 |
| FR2209808A1 (enrdf_load_stackoverflow) | 1974-07-05 |
| FR2209808B1 (enrdf_load_stackoverflow) | 1977-08-12 |
| JPS4986683A (enrdf_load_stackoverflow) | 1974-08-20 |
| CH584730A5 (enrdf_load_stackoverflow) | 1977-02-15 |
| BE808292A (fr) | 1974-06-06 |
| IT1001204B (it) | 1976-04-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8130 | Withdrawal |