DE1282933B - Faerben von Polystyrol oder Polymethylmethacrylat - Google Patents
Faerben von Polystyrol oder PolymethylmethacrylatInfo
- Publication number
- DE1282933B DE1282933B DE1965A0050238 DEA0050238A DE1282933B DE 1282933 B DE1282933 B DE 1282933B DE 1965A0050238 DE1965A0050238 DE 1965A0050238 DE A0050238 A DEA0050238 A DE A0050238A DE 1282933 B DE1282933 B DE 1282933B
- Authority
- DE
- Germany
- Prior art keywords
- anthraquinone
- color
- polystyrene
- phenylthio
- bis
- 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.)
- Pending
Links
- 239000004793 Polystyrene Substances 0.000 title claims description 16
- 238000004040 coloring Methods 0.000 title description 8
- 229920003229 poly(methyl methacrylate) Polymers 0.000 title description 7
- 239000004926 polymethyl methacrylate Substances 0.000 title description 7
- 229920005553 polystyrene-acrylate Polymers 0.000 title description 4
- 229920002223 polystyrene Polymers 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 25
- 239000000203 mixture Substances 0.000 description 10
- FPRGJFFNVANESG-UHFFFAOYSA-N 1-phenylsulfanylanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1SC1=CC=CC=C1 FPRGJFFNVANESG-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000008188 pellet Substances 0.000 description 8
- 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 6
- 238000001125 extrusion Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- CNRPDCKHCGUKDK-UHFFFAOYSA-N 1,8-bis(phenylsulfanyl)anthracene-9,10-dione Chemical compound C=12C(=O)C3=C(SC=4C=CC=CC=4)C=CC=C3C(=O)C2=CC=CC=1SC1=CC=CC=C1 CNRPDCKHCGUKDK-UHFFFAOYSA-N 0.000 description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 238000000748 compression moulding Methods 0.000 description 4
- 238000009987 spinning Methods 0.000 description 4
- JGDLEVAYNWLIKN-UHFFFAOYSA-N 1,5-bis(phenylsulfanyl)anthracene-9,10-dione Chemical compound C=12C(=O)C3=CC=CC(SC=4C=CC=CC=4)=C3C(=O)C2=CC=CC=1SC1=CC=CC=C1 JGDLEVAYNWLIKN-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000004056 anthraquinones Chemical group 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- -1 substituted-phenylthioanthraquinones Chemical class 0.000 description 3
- QPQKUYVSJWQSDY-UHFFFAOYSA-N 4-phenyldiazenylaniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC=C1 QPQKUYVSJWQSDY-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- BNJMRELGMDUDDB-UHFFFAOYSA-N $l^{1}-sulfanylbenzene Chemical compound [S]C1=CC=CC=C1 BNJMRELGMDUDDB-UHFFFAOYSA-N 0.000 description 1
- NGJUNOTUSVFYLD-UHFFFAOYSA-N 1-(methylamino)-4-phenyl-10-sulfanylideneanthracen-9-one Chemical compound CNC1=CC=C(C=2C(C3=CC=CC=C3C(C12)=O)=S)C1=CC=CC=C1 NGJUNOTUSVFYLD-UHFFFAOYSA-N 0.000 description 1
- NWOHUVDXWOLMTA-UHFFFAOYSA-N 4-phenyl-10-sulfanylideneanthracen-9-one Chemical compound O=C1C2=CC=CC=C2C(=S)C2=C1C=CC=C2C1=CC=CC=C1 NWOHUVDXWOLMTA-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 101000952234 Homo sapiens Sphingolipid delta(4)-desaturase DES1 Proteins 0.000 description 1
- 102100037416 Sphingolipid delta(4)-desaturase DES1 Human genes 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000011363 dried mixture Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 235000013980 iron oxide Nutrition 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 230000000485 pigmenting effect Effects 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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
- C08K5/372—Sulfides, e.g. R-(S)x-R'
- C08K5/3725—Sulfides, e.g. R-(S)x-R' containing nitrogen
-
- 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)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39637664A | 1964-09-14 | 1964-09-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1282933B true DE1282933B (de) | 1968-11-14 |
Family
ID=23566956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1965A0050238 Pending DE1282933B (de) | 1964-09-14 | 1965-09-14 | Faerben von Polystyrol oder Polymethylmethacrylat |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS497059B1 (fr) |
| BE (1) | BE669563A (fr) |
| CH (1) | CH496763A (fr) |
| DE (1) | DE1282933B (fr) |
| GB (1) | GB1105568A (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2255033A1 (de) * | 1971-11-15 | 1973-05-24 | Wedco | Kunstharzmasse, verfahren zu ihrer herstellung und ihre verwendung |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4964460U (fr) * | 1972-09-27 | 1974-06-05 | ||
| JPS51140769U (fr) * | 1975-05-02 | 1976-11-12 | ||
| 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 |
| US4446047A (en) * | 1981-02-25 | 1984-05-01 | Imperial Chemical Industries Plc | Pleochroic anthraquinone dyes |
| DE3276868D1 (de) * | 1981-02-25 | 1987-09-03 | Ici Plc | Pleochroic anthraquinone dyes |
| GB2093475B (en) * | 1981-02-25 | 1985-10-09 | Secr Defence | Liquid crystal materials containing pleochroic dithioanthraquinone dyes |
| JP2004067933A (ja) | 2002-08-08 | 2004-03-04 | Dystar Japan Ltd | 高耐光堅牢度を有する黄色系分散染料混合物 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH374964A (de) * | 1961-08-21 | 1964-03-31 | Acna | Verfahren zum Färben von Textilfasern aus Polyolefin mit Anthrachinonfarbstoffen |
-
0
- BE BE669563D patent/BE669563A/xx unknown
-
1965
- 1965-09-09 GB GB3857865A patent/GB1105568A/en not_active Expired
- 1965-09-14 JP JP5589465A patent/JPS497059B1/ja active Pending
- 1965-09-14 DE DE1965A0050238 patent/DE1282933B/de active Pending
- 1965-09-14 CH CH1273965A patent/CH496763A/de unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH374964A (de) * | 1961-08-21 | 1964-03-31 | Acna | Verfahren zum Färben von Textilfasern aus Polyolefin mit Anthrachinonfarbstoffen |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2255033A1 (de) * | 1971-11-15 | 1973-05-24 | Wedco | Kunstharzmasse, verfahren zu ihrer herstellung und ihre verwendung |
Also Published As
| Publication number | Publication date |
|---|---|
| BE669563A (fr) | |
| CH496763A (de) | 1970-09-30 |
| JPS497059B1 (fr) | 1974-02-18 |
| GB1105568A (en) | 1968-03-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0061426B1 (fr) | Procédé de coloration des matières organiques à poids moléculaire élevés et des pigments polycycliques | |
| DE2705656C3 (de) | Pfropfcopolymerisate und Verfahren zu ihrer Herstellung | |
| DE4011162A1 (de) | Thermoplastische formmasse | |
| DE112006000033B4 (de) | Thermoplastische Harzzusammensetzung | |
| DE1570771B2 (de) | Verfahren zur Herstellung einer stabilen Dispersion aus einem synthetischem Polymer in einer organischen Flüssigkeit Ausscheidung aus: 1224504 | |
| DE1620942C3 (de) | Verfahren zur Herstellung von Perlpolymerisaten | |
| DE2716207B2 (de) | Schlagfeste Styrolpolymere | |
| DE1282933B (de) | Faerben von Polystyrol oder Polymethylmethacrylat | |
| DE1669824B2 (de) | Verfahren zum herstellen eines pigmentierten polymerisates | |
| DE2826268C3 (de) | Verfahren zum Färben von thermoplastischen Harzen | |
| DE69901365T2 (de) | Kontinuierliches Verfahren zur Herstellung von Farbstoffzusammensetzungen auf Basis von Polymeren | |
| US3316205A (en) | Colored plastic compositions and colors therefor | |
| DE1569613A1 (de) | Verfahren zur Herstellung eines Phthaloperinons | |
| US3312655A (en) | Coloring of thermoplastic resins | |
| DE1241605B (de) | Rotpigmentierung von Polymeren und plastischen Naturstoffen | |
| DE1960199B2 (de) | Wärmehärtbares Gemisch auf Basis eines ungesättigten GlycMylesterharzes | |
| DE932986C (de) | Verfahren zur Herstellung modifizierter vinylaromatischer Harze | |
| DE2044168C3 (de) | Kolloide Gemische | |
| DE69017813T2 (de) | Methinverbindung. | |
| US3441536A (en) | Synthetic resin compositions containing alpha - phenylthioanthraquinones as colorants | |
| CH623069A5 (en) | Process for pigmenting high molecular-weight organic material | |
| DE2037123C3 (de) | Massefarben von Kunststoffen | |
| CH573959A5 (en) | 4,4'-Diamino-1,1'-dianthrimide used for dyeing plastics in the melt - giving fast blue-green shades esp. with poly-esters | |
| DE2219068A1 (de) | Organische Pigmente und Verfahren zu ihrer Herstellung | |
| US3388094A (en) | Colored plastic compositions and colors therefor |