DE1288789B - Coloring additive to plastics - Google Patents
Coloring additive to plasticsInfo
- Publication number
- DE1288789B DE1288789B DE1964C0034615 DEC0034615A DE1288789B DE 1288789 B DE1288789 B DE 1288789B DE 1964C0034615 DE1964C0034615 DE 1964C0034615 DE C0034615 A DEC0034615 A DE C0034615A DE 1288789 B DE1288789 B DE 1288789B
- Authority
- DE
- Germany
- Prior art keywords
- metal complexes
- plastics
- weight
- cobalt
- coloring additive
- 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
- 239000004033 plastic Substances 0.000 title claims description 10
- 229920003023 plastic Polymers 0.000 title claims description 10
- 238000004040 coloring Methods 0.000 title claims description 4
- 239000000654 additive Substances 0.000 title claims description 3
- 230000000996 additive effect Effects 0.000 title claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 17
- 239000002184 metal Substances 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 14
- 150000007513 acids Chemical class 0.000 claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- 239000003973 paint Substances 0.000 claims description 4
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 239000004922 lacquer Substances 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052797 bismuth Inorganic materials 0.000 claims description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N alpha-isobutyric acid Natural products CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000004700 cobalt complex Chemical class 0.000 description 1
- RUQPYJQHSQKFIP-UHFFFAOYSA-H cobalt(3+);tricarbonate Chemical compound [Co+3].[Co+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O RUQPYJQHSQKFIP-UHFFFAOYSA-H 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- -1 isobutyric acid nitrile Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
-
- 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
- C08K5/0091—Complexes with metal-heteroatom-bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
Description
Gegenstand des Patentes 1 242 857 ist die Verwendung von Metallkomplexen der Diorganodithiophosphinsäuren der allgemeinen Formel als farbender Zusatz zu Kunststoffen oder Lacken, wobei R1 und R2 für gleiche oder verschiedene aliphatische Kohlenwasserstoffreste mit 1 bis 12 C-Atomen, Me für Chrom, Wismut, Nickel, Antimon, Cobalt und n für 2 oder 3 stehen und die Menge der Metallkomplexe 0,05 bis 50,0 Gewichtsprozent, bezogen auf die Kunststoff- oder Lackmenge, beträgt.The subject of patent 1,242,857 is the use of metal complexes of diorganodithiophosphinic acids of the general formula As a coloring additive to plastics or paints, where R1 and R2 stand for identical or different aliphatic hydrocarbon radicals with 1 to 12 carbon atoms, Me stands for chromium, bismuth, nickel, antimony, cobalt and n stands for 2 or 3 and the amount of metal complexes is 0 .05 to 50.0 percent by weight, based on the amount of plastic or paint.
Es wurde nun gefunden, daß man an Stelle der Metallkomplexe der Diorganodithiophosphinsäuren die Metallkomplexe der Diorganodiphosphinsäuren der entsprechenden allgemeinen Formel verwenden kann.It has now been found that the metal complexes of the diorganodiphosphinic acids of the corresponding general formula can be used instead of the metal complexes of the diorganodithiophosphinic acids can use.
Zu der hier nicht beanspruchten Herstellung der Metallkomplexe werden die Carbonate, Hydroxide oder Oxide der Metalle in einem inerten Lösungsmittel, wie beispielsweise Benzol, mit Diorganophosphinsäure bei erhöhter Temperatur umgesetzt. Die Carbonate, Hydroxide oder Oxide und die Diorganophosphinsäure werden hierzu in etwa äquivalenten Verhältnissen eingesetzt. Nach Filtration und Einengen des Reaktionsgemisches fällt der angestrebte Metallkomplex beim Abkühlen auf Raumtemperatur aus. Der von der Mutterlauge abgetrennte Metallkomplex kann aus Isopropanol umkristallisiert werden. For the production of the metal complexes not claimed here the carbonates, hydroxides or oxides of the metals in an inert solvent, such as benzene, reacted with diorganophosphinic acid at elevated temperature. The carbonates, hydroxides or oxides and the diorganophosphinic acid are used for this used in approximately equivalent proportions. After filtration and concentration of the In the reaction mixture, the desired metal complex falls on cooling to room temperature the end. The metal complex separated from the mother liquor can be recrystallized from isopropanol will.
In Kunststoffe können die Metallkomplexe der Diorganodiphosphinsäure einzeln oder im Gemisch nach bekannten Verfahren eingebracht werden. The metal complexes of diorganodiphosphinic acid can be used in plastics be introduced individually or in a mixture according to known methods.
Einige der erfindungsgemäß verwendbaren Metallkomplexe der Diorganodiphosphinsäuren vermindern die Wirkung von Polymerisationskatalysatoren. In solchen Fällen lassen sich jedoch andere Katalysatoren durch einfache Vorversuche ermitteln, auf deren Wirksamkeit die Metallkomplexe keinen Einfluß haben. Some of the metal complexes of the diorganodiphosphinic acids which can be used according to the invention reduce the effect of polymerization catalysts. In such cases leave However, other catalysts can be determined by simple preliminary tests on their Effectiveness the metal complexes have no influence.
Die Metallkomplexe der Diorganodiphosphinsäuren können in thermoplastische Kunststoffe aber auch während deren Verarbeitung bei erhöhter Temperatur eingearbeitet werden. The metal complexes of the diorganodiphosphinic acids can be converted into thermoplastic Plastics are also incorporated during processing at elevated temperatures will.
Sowohl in den Kunststoffen als auch in den verstrichenen und getrockneten Lacken zeichnen sich die Metallkomplexe durch hohe Farbintensität und -brillanz aus, so daß im allgemeinen eine ausreichende Färbung bewirkt wird, wenn diese 0,05 bis 1,0 Gewichtsprozent der Metallkomplexe enthalten. Both in the plastics and in the coated and dried ones Lacquers, the metal complexes are characterized by high color intensity and brilliance so that, in general, sufficient coloring is effected when this is 0.05 contain up to 1.0 percent by weight of the metal complexes.
Da sich die Metallkomplexe als lösliche Farbstoffe leicht einarbeiten lassen und bereits in geringen Mengen einen vorzüglichen Farbeffekt geben, sind sie als Farbstoffe für transparent gefärbte Kunststoffe oder Lacke hervorragend geeignet. Die damit gefärbten Kunststoffe oder Lacke zeichnen sich durch hohe Lichtechtheit aus, da die Metallkomplexe nicht nur thermisch sehr beständig sind, sondern auch gegen Bestrahlung mit ultravioletten Strahlen. Since the metal complexes are easily incorporated as soluble dyes and give an excellent color effect even in small quantities they are excellent as dyes for transparently colored plastics or paints suitable. The plastics or lacquers colored with it are characterized by high lightfastness because the metal complexes are not only very thermally stable, but also against exposure to ultraviolet rays.
Die Metallkomplexe haben keine Tendenz auszublühen oder auszuschwitzen.The metal complexes have no tendency to bloom or exude.
Beispiel a) Herstellung des Cobalt(l 1)-komplexes der Dipropyldiphosphinsäure 1,2 Gewichtsteile Cobalt(lI)-carbonat werden mit 3 Gewichtsteilen Dipropyldiphosphinsäure in 70 Gewichtsteilen Benzol 3 Stunden lang unter Rückflußkühlung zum Sieden erhitzt. Nach Filtration wird die erhaltene tiefblaue Lösung eingeengt und auf Raumtemperatur abgekühlt. Dabei fallen in 87oiger Ausbeute tiefblaue Kristalle des Cobalt (ll)-komplexes der Dipropyldiphosphinsäure an, die durch Umkristallisieren aus Isopropanol gereinigt werden. b) Herstellung eines gefärbten Kunststoffs In 100 Gewichtsteilen monomeren Methylmethacrylats werden 0, 1 Gewichtsteile des Cobalt(II)-komplexes der Dipropyldiphosphinsäure [~ (c3HkP (o) o] sco gelöst. Nach Zusatz von 0,1 Gewichtsteilen N,N'-Azo-bis-(isobuttersäurenitril) wird diese Lösung unter Formgebung bei einer Temperatur von 60 bis 120"C polymerisiert und ausgehärtet. Erhalten werden klar durchsichtige blaue Formteile, die während oder nach einer 500 Stunden andauernden Bestrahlung mit UV-Licht ihre Farbe nicht ändern. Bei über 3 Monate gelagerten Formteilen tritt kein Ausblühen oder Ausschwitzen des als Farbkomponente in dem Formteil enthaltenen Cobaltkomplexes der Dipropyldiphosphinsäure auf. Example a) Preparation of the cobalt (l 1) complex of dipropyldiphosphinic acid 1.2 parts by weight of cobalt (III) carbonate are mixed with 3 parts by weight of dipropyldiphosphinic acid heated to boiling under reflux for 3 hours in 70 parts by weight of benzene. After filtration, the deep blue solution obtained is concentrated and brought to room temperature cooled down. Deep blue crystals of the cobalt (II) complex fall in 87o yield of dipropyldiphosphinic acid, which is purified by recrystallization from isopropanol will. b) Production of a colored plastic in 100 parts by weight of monomer Methyl methacrylate becomes 0.1 part by weight of the cobalt (II) complex of dipropyldiphosphinic acid [~ (c3HkP (o) o] sco dissolved. After the addition of 0.1 part by weight of N, N'-azo-bis- (isobutyric acid nitrile) this solution is polymerized with shaping at a temperature of 60 to 120.degree and hardened. Clear, transparent blue moldings are obtained, which during or after 500 hours of exposure to UV light, they lose their color change. If molded parts have been stored for more than 3 months, there is no blooming or exudation of the cobalt complex of dipropyldiphosphinic acid contained as a color component in the molded part on.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1964C0034615 DE1288789B (en) | 1964-12-11 | 1964-12-11 | Coloring additive to plastics |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1964C0034615 DE1288789B (en) | 1964-12-11 | 1964-12-11 | Coloring additive to plastics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1288789B true DE1288789B (en) | 1969-02-06 |
Family
ID=7021411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1964C0034615 Pending DE1288789B (en) | 1964-12-11 | 1964-12-11 | Coloring additive to plastics |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1288789B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2920080A1 (en) * | 1979-05-18 | 1980-11-20 | Inst Chimii Baschkirskowo Fili | Coloured polymer prepn. - by polymerising monomer in presence of sulphoxide phosphine oxide tri:butyl phosphate, di:isoamyl phosphonate etc. |
-
1964
- 1964-12-11 DE DE1964C0034615 patent/DE1288789B/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2920080A1 (en) * | 1979-05-18 | 1980-11-20 | Inst Chimii Baschkirskowo Fili | Coloured polymer prepn. - by polymerising monomer in presence of sulphoxide phosphine oxide tri:butyl phosphate, di:isoamyl phosphonate etc. |
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