CH683692A5 - Flame retardant a halogenated alkyl-aryl ethers for organic polymers. - Google Patents
Flame retardant a halogenated alkyl-aryl ethers for organic polymers. Download PDFInfo
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- CH683692A5 CH683692A5 CH2049/92A CH204992A CH683692A5 CH 683692 A5 CH683692 A5 CH 683692A5 CH 2049/92 A CH2049/92 A CH 2049/92A CH 204992 A CH204992 A CH 204992A CH 683692 A5 CH683692 A5 CH 683692A5
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- CH
- Switzerland
- Prior art keywords
- flame retardant
- component
- formula
- tin
- halogen
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- 239000003063 flame retardant Substances 0.000 title claims description 20
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title claims description 16
- 150000001346 alkyl aryl ethers Chemical class 0.000 title claims description 5
- 229920000620 organic polymer Polymers 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000012141 concentrate Substances 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000011368 organic material Substances 0.000 claims description 4
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 4
- 229910000410 antimony oxide Inorganic materials 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 claims description 3
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- WCRDXYSYPCEIAK-UHFFFAOYSA-N dibutylstannane Chemical group CCCC[SnH2]CCCC WCRDXYSYPCEIAK-UHFFFAOYSA-N 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- CMCOFAYLDYIEBR-UHFFFAOYSA-L 2-[carboxymethylsulfanyl(dioctyl)stannyl]sulfanylacetic acid Chemical compound [O-]C(=O)CS.[O-]C(=O)CS.CCCCCCCC[Sn+2]CCCCCCCC CMCOFAYLDYIEBR-UHFFFAOYSA-L 0.000 claims 1
- 239000004753 textile Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 9
- -1 polypropylene Polymers 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 8
- 239000004743 Polypropylene Substances 0.000 description 7
- 229920001155 polypropylene Polymers 0.000 description 7
- 239000003381 stabilizer Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 3
- 238000009987 spinning Methods 0.000 description 3
- 239000004594 Masterbatch (MB) Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000000779 smoke Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/14—Macromolecular materials
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K3/2279—Oxides; Hydroxides of metals of antimony
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1545—Six-membered 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
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
- C08K5/57—Organo-tin compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Fireproofing Substances (AREA)
- Artificial Filaments (AREA)
Description
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CH 683 692 A5 CH 683 692 A5
Beschreibung description
Die vorliegende Erfindung betrifft Flammschutzmittel für polymere organische Materialien, die mit einem Verarbeitungs-Stabilisator, zum Schutz der Polymeren, kombiniert sind. The present invention relates to flame retardants for polymeric organic materials which are combined with a processing stabilizer to protect the polymers.
Die erfindungsgemässen Flammschutzmittel-Kombinationen enthalten a) einen halogenierten Alkyl-aryläther, worin die Aryigruppe durch Halogen substituiert sein kann und b) a-Tokopherol. The flame retardant combinations according to the invention contain a) a halogenated alkyl aryl ether, in which the aryi group can be substituted by halogen and b) a-tocopherol.
Vorzugsweise enthält die Kombination zusätzlich c) eine Organozinn-Verbindung und/oder ein Antimonoxid, vorzugsweise eine Organozinn-Verbin-dung. The combination preferably additionally comprises c) an organotin compound and / or an antimony oxide, preferably an organotin compound.
Die bevorzugten Alkyl-aryläther entsprechen der Formel I The preferred alkyl aryl ethers correspond to formula I.
R! -(O/-0CH2-CH-CH2Br R! - (O / -0CH2-CH-CH2Br
Br Br
(I), (I),
worin Ri Halogen oder, vorzugsweise, eine Gruppe der Formel (d) wherein Ri is halogen or, preferably, a group of the formula (d)
BrCH2-CH-CH20 -<0>- A - (d), BrCH2-CH-CH20 - <0> - A - (d),
Br Y Br Y
(R2)m2 (R2) m2
FÌ2 Halogen, vorzugsweise Chlor oder Brom, insbesondere Brom, FÌ2 halogen, preferably chlorine or bromine, especially bromine,
mi und m2, unabhängig voneinander 0, 1 oder 2, vorzugsweise 2, mi and m2, independently of one another 0, 1 or 2, preferably 2,
A eine direkte Bindung oder Ci-4-Alkylen oder ein Brückenglied der Formel A is a direct bond or Ci-4-alkylene or a bridge member of the formula
H5C6-CH^ , -0-, -S- oder -S02- H5C6-CH ^, -0-, -S- or -S02-
bedeuten. mean.
a-Tokopherol entspricht der Formel II a-tocopherol corresponds to formula II
CH3 I CH. CH3 I CH.
HO—' HO— '
CH. CH.
CH, CH,
I I.
CH, CH,
CH3 CH3
H,C—• H, C— •
C—(CH2)3—CH—(CHj),—CH—(CH2)3—CH—CH3 C - (CH2) 3 - CH - (CHj), - CH - (CH2) 3 - CH - CH3
(II) (II)
ch3 ch3
CH, CH,
Bevorzugte Organozinn-Verbindungen sind Di-(Ci-i2-alkyl)-Sn-Carboxylate und Di-(Ci-i2-alkyl)-Sn-Mercaptide, insbesondere Dibutyl-Zinnmaleat, Dioctyl-Zinnlaurat und Dibutyl- oder Dioctyl-Zinnthioglyko-lat, der Formeln III, bzw. IV Preferred organotin compounds are di- (Ci-i2-alkyl) -Sn carboxylates and di- (Ci-i2-alkyl) -Sn-mercaptides, especially dibutyl-tin maleate, dioctyl-tin laurate and dibutyl or dioctyl-tin thioglyco-lat , of formulas III and IV
(C8Hi7)2 Sn (SCH2COOC8Hi7)2 (III) (C8Hi7) 2 Sn (SCH2COOC8Hi7) 2 (III)
(C4H9)2 Sn (SCH2COOC8Hi7)2 (IV). (C4H9) 2 Sn (SCH2COOC8Hi7) 2 (IV).
Unter den Antimonoxiden kommen sowohl Sb203 als auch SbaOs in Betracht. Both Sb203 and SbaOs can be considered among the antimony oxides.
Vorzugsweise bedeutet A in Formel d die direkte Bindung, -O- oder Ci-4-Alkylen, insbesondere die A in formula d preferably denotes the direct bond, -O- or Ci-4-alkylene, in particular that
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CH 683 692 A5 CH 683 692 A5
direkte Bindung oder Ci-^-Alkylen. Wenn A Ci_4-Alkyien bedeutet, ist dieses vorzugsweise -CH2CH2-oder, insbesondere, =C(CH3)2. direct bond or Ci - ^ - alkylene. If A is Ci_4-alkyl, this is preferably -CH2CH2-or, in particular, = C (CH3) 2.
Bevorzugte Verbindungen der Formel I entsprechen der Formel I a Preferred compounds of the formula I correspond to the formula I a
BrCH2-CHCH20 -/ Q V BrCH2-CHCH20 - / Q V
A - A -
Br Br
O)- OCH2-CHCH2Br O) - OCH2-CHCH2Br
Br Br
(I a). (I a).
Die Verbindungen der Formel I bis IV sind bekannt. The compounds of the formulas I to IV are known.
Die erfindungsgemässen Flammschutzmittel-Kompositionen zeigen gegenüber den bisher bekannten Flammschutzmitteln eine bessere Wirkung. The flame retardant compositions according to the invention show a better effect than the previously known flame retardants.
Man verwendet im allgemeinen 0,5 bis 9%, vorzugsweise 1 bis 4% Flammschutzmittel, bezogen auf das Gewicht des zu schützenden Polymers. Die erfindungsgemässen Kompositionen können dem Polymer vor, während oder nach der Polymerisation, in fester Form oder in einem Lösungsmittel (20 bis 80 Gewichtsprozent Lösungsmittelanteil) oder in Form eines Wirkstoffkonzentrates (Masterbatch), das 20 bis 80, vorzugsweise 40 bis 70 Gewichtsprozent der erfindungsgemässen Flammschutzmittel-Kombination und 80 bis 20, vorzugsweise 60 bis 30 Gewichtsprozent eines Polymeren enthält, wobei das Polymer mit dem zu schützenden Polymeren identisch sein kann oder zumindest mit diesem verträglich ist. In general, 0.5 to 9%, preferably 1 to 4%, of flame retardant, based on the weight of the polymer to be protected, is used. The compositions according to the invention can be added to the polymer before, during or after the polymerization, in solid form or in a solvent (20 to 80 percent by weight solvent) or in the form of an active ingredient concentrate (masterbatch) containing 20 to 80, preferably 40 to 70 percent by weight of the flame retardants according to the invention Combination and 80 to 20, preferably 60 to 30 percent by weight of a polymer, wherein the polymer may be identical to the polymer to be protected or at least compatible with it.
In den erfindungsgemässen Kompositionen ist das Gewichtsverhältnis der Komponente a) zur Komponente b) im allgemeinen 400:1 bis 5:1, vorzugsweise 200:1 bis 8:1, insbesondere 100:1 bis 10:1. In the compositions according to the invention, the weight ratio of component a) to component b) is generally 400: 1 to 5: 1, preferably 200: 1 to 8: 1, in particular 100: 1 to 10: 1.
Komponente c) kann im Verhältnis zur Summe a) + b) etwa 1:50 bis 1:5, vorzugsweise 1:25 bis 1:6, insbesondere 1:14 bis 1:8 sein. Component c) can be about 1:50 to 1: 5, preferably 1:25 to 1: 6, in particular 1:14 to 1: 8 in relation to the sum a) + b).
Zum flammhemmenden Ausrüsten von organischen Stoffen werden die Verbindungen entsprechend den Komponenten a), b) und c) in die entflammbaren Materialien eingearbeitet oder aufgebracht. Für diese Behandlung geeignet sind vor allem organische polymere Materialien, beispielsweise Polypropylen, Polyäthylen, Polystyrol, ABS, vorzugsweise für Spritzguss und Spinnmassen, zur Herstellung von extrudierten Artikeln, Folien und Spinnmassen. Insbesondere geeignet für die Behandlung mit den erfindungsgemässen Zusammensetzungen sind Polypropylenmassen, die zu Fasern, Folien oder Bändchen verarbeitet werden. For the flame-retardant finishing of organic substances, the compounds corresponding to components a), b) and c) are incorporated or applied in the flammable materials. Organic polymeric materials are particularly suitable for this treatment, for example polypropylene, polyethylene, polystyrene, ABS, preferably for injection molding and spinning masses, for the production of extruded articles, films and spinning masses. Polypropylene compositions which are processed into fibers, films or tapes are particularly suitable for treatment with the compositions according to the invention.
Zur Einarbeitung der flammhemmenden Zusammensetzung in die Polymeren können die verschiedenen bekannten Verfahren angewendet werden. Bevorzugt ist die Verwendung in Polypropylen, vorzugsweise in Polypropylenfasern oder Polypropylenfolien. The various known methods can be used to incorporate the flame-retardant composition into the polymers. Use in polypropylene, preferably in polypropylene fibers or polypropylene films, is preferred.
Die erfindungsgemässe Zusammensetzung hat den Vorteil, dass sie keine oder nur eine geringe Herabsetzung der Filterstandzeit bei Polypropylen-Faserspinnanlagen verursacht. Ferner tritt keine Rauchentwicklung an den Spinndüsen sowie kein Anstieg des Schmelzindexes der Polymerschmelze auf. Überraschenderweise zeigt also die erfindungsgemässe Zusammensetzung einen hohen flammhemmenden Effekt, ohne die verarbeitungsseitigen Eigenschaften wie Filterstandzeit, Schmelzindex oder Rauchentwicklung merkbar zu verschlechtern. The composition according to the invention has the advantage that it causes no or only a slight reduction in the filter service life in polypropylene fiber spinning systems. Furthermore, there is no smoke development at the spinnerets and no increase in the melt index of the polymer melt. Surprisingly, the composition according to the invention thus exhibits a high flame-retardant effect without noticeably deteriorating the properties on the processing side, such as filter service life, melt index or smoke development.
Die erfindungsgemässen Flammschutzmittel können allein oder in Kombination mit anderen Stabilisatoren, z.B. Lichtschutzstabilisatoren und Antioxidantien, z.B. sterisch gehinderten Verbindungen eingesetzt werden. The flame retardants according to the invention can be used alone or in combination with other stabilizers, e.g. Sunscreen stabilizers and antioxidants, e.g. sterically hindered compounds are used.
Beispiele für solche Stabilisatoren sind sterisch gehinderte Phenole oder sterisch gehinderte Amine, Phosphor- oder Schwefel-enthaltende Verbindungen und Gemische dieser bekannten Verbindungen. Examples of such stabilizers are hindered phenols or hindered amines, phosphorus or sulfur-containing compounds and mixtures of these known compounds.
In den folgenden Beispielen bedeuten die Teile Gewichtsteile und die Prozente Gewichtsprozente. Die Temperaturen sind in Celsiusgraden angegeben. In the following examples, parts are parts by weight and percentages are percentages by weight. The temperatures are given in degrees Celsius.
BEISPIEL 1 EXAMPLE 1
43,28 Teile der Verbindung der Formel I a (oben), worin A eine Gruppe der Formel =C(CH3)2 ist, 1,0 Teil der Verbindung der Formel II (oben, = a-Tokopherol) und 4,36 Teile Dibutyl-Sn-maleat werden mit 51,36 Teilen handelsüblichem Polyäthylen (MFl = melt flow index bei 190°/2,16 kp 17 bis 22) gemischt, in einem Kneter oder Extruder homogenisiert und zu einem Wirkstoffkonzentrat (Masterbatch) in Granulatform verarbeitet. 43.28 parts of the compound of the formula I a (top), in which A is a group of the formula = C (CH3) 2, 1.0 part of the compound of the formula II (top, = a-tocopherol) and 4.36 parts Dibutyl-Sn-maleate are mixed with 51.36 parts of commercially available polyethylene (MFl = melt flow index at 190 ° / 2.16 kp 17 to 22), homogenized in a kneader or extruder and processed into an active ingredient concentrate (masterbatch) in granular form.
BEISPIEL 2 EXAMPLE 2
95 Teile eines handelsüblichen Polypropylen in Pulverform (MFl 230°/2,16 kp 4) wird mit 5 Teilen des Wirkstoffkonzentrats gemäss Beispiel 1 gemischt, danach auf einem Walzwerk (Schwabenthan) bei 165 95 parts of a commercially available polypropylene in powder form (MFI 230 ° / 2.16 kp 4) are mixed with 5 parts of the active ingredient concentrate according to Example 1, then on a rolling mill (Schwabenthan) at 165
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CH 683 692 A5 CH 683 692 A5
bis 175° während 5 Minuten homogenisiert. Aus dem erhaltenen Walzfell werden in einer Presse (Bucher-Guyer) in 3 Minuten bei 230° Platten von 1 mm Dicke hergestellt. Mit diesen Platten wurden die folgenden Versuche durchgeführt: homogenized at 175 ° for 5 minutes. The rolled skin obtained is used in a press (Bucher-Guyer) in 3 minutes at 230 ° to produce sheets of 1 mm thickness. The following tests were carried out with these plates:
1. Bestimmung des LOI-Wertes nach ASTM-D 2863, 1. Determination of the LOI value according to ASTM-D 2863,
2. Senkrechttest nach DIN 53 438, 2. Vertical test according to DIN 53 438,
3. Extrusion in einem Extruder (Händle) bei 230° und anschliessender Granulation. Vom Granulat wird der MFI-Wert bei 230°/2,16 kp gemessen. Diese Prozedur wird noch weitere 4 Male mit dem jeweils erhaltenen Granulat durchgeführt und die erhaltenen MFI-Werte gemessen. 3. Extrusion in an extruder (Handel) at 230 ° and subsequent granulation. The MFI value of the granules is measured at 230 ° / 2.16 kp. This procedure is carried out a further 4 times with the granules obtained in each case and the MFI values obtained are measured.
4. Es wird in einem Extrusiometer (Göttfert) bei einem Temperaturgradienten von 185°-240° und einem Durchsatz von 1,2 kg/Stunde extrudiert. Es wird die Zeit gemessen, bis an einem vor der Düse angebrachten Siebpaket (900/16000/900 Maschen/cm2) der Massedruck auf 86 bar angestiegen ist. 4. It is extruded in an extrusiometer (Göttfert) at a temperature gradient of 185 ° -240 ° and a throughput of 1.2 kg / hour. The time is measured until the mass pressure has risen to 86 bar on a sieve packet (900/16000/900 mesh / cm2) fitted in front of the nozzle.
In allen 4 Tests erhält man sehr gute Resultate. In all 4 tests you get very good results.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB919114416A GB9114416D0 (en) | 1991-07-03 | 1991-07-03 | Improvements in or relating to organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH683692A5 true CH683692A5 (en) | 1994-04-29 |
Family
ID=10697785
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH2049/92A CH683692A5 (en) | 1991-07-03 | 1992-06-30 | Flame retardant a halogenated alkyl-aryl ethers for organic polymers. |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPH05202359A (en) |
| CH (1) | CH683692A5 (en) |
| DE (1) | DE4221285C2 (en) |
| FR (1) | FR2678631B1 (en) |
| GB (1) | GB9114416D0 (en) |
| IT (1) | IT1263216B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6690033B1 (en) * | 2019-03-08 | 2020-04-28 | 櫻護謨株式会社 | Two-component flame-retardant polyurea resin raw material for coating film formation and method for forming flame-retardant polyurea resin coating film |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4006118A (en) * | 1971-07-28 | 1977-02-01 | Marubishi Yuka Kogyo Kabushiki Kaisha | Flame-retardant thermoplastic polymer compositions |
| BE899611A (en) * | 1983-05-13 | 1984-11-09 | Sandoz Sa | NEW FLAME RETARDANT COMPOSITIONS. |
-
1991
- 1991-07-03 GB GB919114416A patent/GB9114416D0/en active Pending
-
1992
- 1992-06-29 DE DE4221285A patent/DE4221285C2/en not_active Expired - Fee Related
- 1992-06-30 CH CH2049/92A patent/CH683692A5/en not_active IP Right Cessation
- 1992-06-30 FR FR9208139A patent/FR2678631B1/en not_active Expired - Fee Related
- 1992-07-01 IT ITRM920498A patent/IT1263216B/en active IP Right Grant
- 1992-07-01 JP JP4174462A patent/JPH05202359A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05202359A (en) | 1993-08-10 |
| ITRM920498A1 (en) | 1994-01-01 |
| DE4221285C2 (en) | 2001-12-06 |
| FR2678631B1 (en) | 2002-01-25 |
| GB9114416D0 (en) | 1991-08-21 |
| FR2678631A1 (en) | 1993-01-08 |
| ITRM920498A0 (en) | 1992-07-01 |
| DE4221285A1 (en) | 1993-01-07 |
| IT1263216B (en) | 1996-08-05 |
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| Date | Code | Title | Description |
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| NV | New agent |
Representative=s name: SANDOZ TECHNOLOGIE AG |
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| PUE | Assignment |
Owner name: SANDOZ AG TRANSFER- CLARIANT FINANCE (BVI) LIMITED |
|
| NV | New agent |
Representative=s name: CLARIANT INTERNATIONAL LTD. |
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| PL | Patent ceased |