CA2467119A1 - Novel flame retarding compounds - Google Patents
Novel flame retarding compounds Download PDFInfo
- Publication number
- CA2467119A1 CA2467119A1 CA002467119A CA2467119A CA2467119A1 CA 2467119 A1 CA2467119 A1 CA 2467119A1 CA 002467119 A CA002467119 A CA 002467119A CA 2467119 A CA2467119 A CA 2467119A CA 2467119 A1 CA2467119 A1 CA 2467119A1
- Authority
- CA
- Canada
- Prior art keywords
- independently
- carbon atoms
- group
- sterically hindered
- flame
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/94—Oxygen atom, e.g. piperidine N-oxide
-
- 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 System
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
-
- 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 System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/59—Hydrogenated pyridine rings
-
- 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 System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65746—Esters of oxyacids of phosphorus the molecule containing more than one cyclic phosphorus atom
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0066—Flame-proofing or flame-retarding additives
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/529—Esters containing heterocyclic rings not representing cyclic esters of phosphoric or phosphorous acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Fireproofing Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Novel flame retarding compounds that comprise at least one sterically hindered nitroxyl, hydroxylamine or hydrocarbyloxyamine moiety and at least one conventional organohalogen or organophosphorus flame retardant moiety, represented by (I) where HA is independently of each other a sterically hindered nitroxyl, sterically hindered hydroxylamine or sterically hindered hydrocarbyloxyamine moiety, L is independently of each other a direct bond or chemical linking group, FRM is independently of each other an organohalogen or an organophosphorus flame reatardant moiety, and x, y and z are each independently greater than or equal to 1, are especially effective towards providing flame retardancy to organic polymer substrates.
Claims (17)
1. A compound of the formula where HA is independently of each other a sterically hindered nitroxyl, sterically hindered hydroxylamine or sterically hindered hydrocarbyloxyamine moiety, L is independently of each other a direct bond or chemical linking group, FRM is independently of each other an organohalogen or an organophosphorus flame reatardant moiety, and x, y and z are each independently greater than or equal to 1.
2. A compound according to claim 1, which compound is represented by formula I, II
or III
where R is hydrogen or methyl, G1 and G2 are independently alkyl of 1 to 4 carbon atoms or are together pentamethylene, x, y and z are each independently greater than or equal to 1, L is independently of each other a direct bond or a divalent hydrocarbylene group or a polyvalent polymeric group, Z1 and Z2 are independently hydrogen or hydrocarbyl, or together form a hydrocarbylene group, or are independently-OR1, -OCOR1, -COOR1, -CONR1R2, -NR1COR2, -COR1, or -NR1R2, R1 and R2 are independently of each other hydrogen or hydrocarbyl, or R1 and together form a hydrocarbylene group, E is oxyl, hydroxyl, alkoxy, cycloalkoxy, aralkoxy, aryloxy, -O-CO-OG, -O-Si(G)3, or -O-CH2-OG where G is selected from the group consisting of hydrogen, an aliphatic, araliphatic and aromatic moiety; or E is -O-T-(OH)b, T is a straight or branched chain alkylene of 1 to 18 carbon atoms, cycloalkylene of 5 to 18 carbon atoms, cycloalkenylene of 5 to 18 carbon atoms, a straight or branched chain alkylene of 1 to 4 carbon atoms substituted by phenyl or by phenyl substituted by one or two alkyl groups of 1 to 4 carbon atoms, b is 1, 2 or 3 with the proviso that b cannot exceed the number of carbon atoms in T, and when b is 2 or 3, each hydroxyl group is attached to a different carbon atoms of T, and FRM is independently of each other an organohalogen or an organophosphorus flame retardant moiety.
or III
where R is hydrogen or methyl, G1 and G2 are independently alkyl of 1 to 4 carbon atoms or are together pentamethylene, x, y and z are each independently greater than or equal to 1, L is independently of each other a direct bond or a divalent hydrocarbylene group or a polyvalent polymeric group, Z1 and Z2 are independently hydrogen or hydrocarbyl, or together form a hydrocarbylene group, or are independently-OR1, -OCOR1, -COOR1, -CONR1R2, -NR1COR2, -COR1, or -NR1R2, R1 and R2 are independently of each other hydrogen or hydrocarbyl, or R1 and together form a hydrocarbylene group, E is oxyl, hydroxyl, alkoxy, cycloalkoxy, aralkoxy, aryloxy, -O-CO-OG, -O-Si(G)3, or -O-CH2-OG where G is selected from the group consisting of hydrogen, an aliphatic, araliphatic and aromatic moiety; or E is -O-T-(OH)b, T is a straight or branched chain alkylene of 1 to 18 carbon atoms, cycloalkylene of 5 to 18 carbon atoms, cycloalkenylene of 5 to 18 carbon atoms, a straight or branched chain alkylene of 1 to 4 carbon atoms substituted by phenyl or by phenyl substituted by one or two alkyl groups of 1 to 4 carbon atoms, b is 1, 2 or 3 with the proviso that b cannot exceed the number of carbon atoms in T, and when b is 2 or 3, each hydroxyl group is attached to a different carbon atoms of T, and FRM is independently of each other an organohalogen or an organophosphorus flame retardant moiety.
3. A compound according to claim 2 in which E is oxyl, hydroxyl, C1-C24alkoxy, C7cycloalkoxy or C7-C9aralkoxy;
L is a direct bond, a divalent group derived from C1-C24alkyl, C2-C24alkenyl, phenyl, naphthyl, biphenyl, C7-C9alkylaryl, or a polyvalent polymeric group; and the flame retardant moiety FRM is selected from the group consisting of alkyl of 1 to 18 carbon atoms substituted by 1 to 37 bromine or chlorine atoms; cycloalkyl of 5 to 12 carbon atoms substituted by 1 to 23 bromine or chlorine atoms; aralkyl of 7 to 15 carbon atoms substituted by 1 to 5 bromine or chlorine atoms; aryl of 6 to 12 carbon atoms substituted by 5 to 9 bromine or chlorine atoms;
wherein T1 and T2 are independently C1-C24alkyl, phenyl, naphthyl, biphenylyl, C24alkoxy, C7-C9aralkoxy or di(C1-C18alkyl)amino; or said alkyl, aryl, alkoxy, aralkoxy or dialkylamino substituted by 1 to 8 halogen atoms;
or FRM is where X is chloro or bromo;
;
where one of the open bonds may be bonded to T1 defined above;
where one of the open bonds may be bonded to T1, defined above;
where one to three of the open bonds may be bonded to T1, defined above;
where one to three of the open bonds may be bonded to T1, defined above;
where one to three of the open bonds may be bonded to T1, defined above;
where one of the open bonds may be bound to alkyl or aryl; or said alkyl or aryl substituted by 1 to 8 halogen atoms;
where one of the open bonds may be bound to alkyl or aryl; or said alkyl or aryl substituted by 1 to 8 halogen atoms;
where X is chlorine or bromine; and where one of the open bonds may be bonded to T1, defined above;
and -(phosphazene flame retardant).
L is a direct bond, a divalent group derived from C1-C24alkyl, C2-C24alkenyl, phenyl, naphthyl, biphenyl, C7-C9alkylaryl, or a polyvalent polymeric group; and the flame retardant moiety FRM is selected from the group consisting of alkyl of 1 to 18 carbon atoms substituted by 1 to 37 bromine or chlorine atoms; cycloalkyl of 5 to 12 carbon atoms substituted by 1 to 23 bromine or chlorine atoms; aralkyl of 7 to 15 carbon atoms substituted by 1 to 5 bromine or chlorine atoms; aryl of 6 to 12 carbon atoms substituted by 5 to 9 bromine or chlorine atoms;
wherein T1 and T2 are independently C1-C24alkyl, phenyl, naphthyl, biphenylyl, C24alkoxy, C7-C9aralkoxy or di(C1-C18alkyl)amino; or said alkyl, aryl, alkoxy, aralkoxy or dialkylamino substituted by 1 to 8 halogen atoms;
or FRM is where X is chloro or bromo;
;
where one of the open bonds may be bonded to T1 defined above;
where one of the open bonds may be bonded to T1, defined above;
where one to three of the open bonds may be bonded to T1, defined above;
where one to three of the open bonds may be bonded to T1, defined above;
where one to three of the open bonds may be bonded to T1, defined above;
where one of the open bonds may be bound to alkyl or aryl; or said alkyl or aryl substituted by 1 to 8 halogen atoms;
where one of the open bonds may be bound to alkyl or aryl; or said alkyl or aryl substituted by 1 to 8 halogen atoms;
where X is chlorine or bromine; and where one of the open bonds may be bonded to T1, defined above;
and -(phosphazene flame retardant).
4. A compound according to claim 1 that comprises a sterically hindered nitroxyl, sterically hindered hydroxylamine or sterically hindered hydrocarbyloxyamine moiety selected from the group consisting of
5. A compound according to claim 2 selected from the group consisting of
6. A flame retardant composition which comprises (A) an organic polymer substrate and (B) an effective flame retarding amount of at least one compound of claim 1.
7. A composition according to claim 6 containing no antimony compounds or antimony compounds in an amount less than about 1% by weight based on the weight of the polymer component (A).
8. A composition according to claim 6 containing no flame-retardant filler or a flame-retardant filler in an amount less than about 3% by weight based on the weight of the polymer component (A).
9. A composition according to claim 6 in which the polymer component (A) is a thermoplastic polymer.
10. A composition according to claim 6 in which the molecular weight of the compound of component (B) is in the range 170 - 10000 g/mol.
11. A composition according to claim 6 in which the compound of component (B) is present from about 0.1 to about 10% by weight based on the weight of the polymer substrate (A).
12. A composition according to claim 6 which comprises as further component a halogenated flame retardant selected from the group consisting of organic aromatic halogenated compounds; organic cycloaliphatic or polycycloaliphatic halogenated compounds; and organic aliphatic halogenated compounds; especially chloroalkyl phosphate esters, polybrominated diphenyl oxide, decabromodiphenyl oxide, tris[3-bromo-2,2-bis(bromomethyl)propyl] phosphate, bis(2,3-dibromopropyl ether) of bisphenol A, brominated epoxy resin, ethylene-bis(tetrabromophthalimide), bis(hexachlorocyclopentadieno)cyclooctane, chlorinated paraffins, 1,2-bis(tribromophenoxy)ethane, tetrabromo-bisphenol A, ethylene bis-(dibromo-norbornanedicarboximide), bis-(hexachlorocyclopentadieno) cyclooctane, tris-(2,3-dibromopropyl)-isocyanurate, and ethylene-bis-tetrabromophthalimide.
13. A composition according to claim 12 in which the the halogenated flame retardant of component is from about 0.5 to about 40% by weight based on the weight of the polymer substrate (A).
14. A composition according to claim 6 comprising a further component selected from the group consisting of pigments, dyes, plasticizers, phenolic antioxidants, thixotropic agents, levelling assistants, basic costabilizers, calcium stearate, zinc stearate, nitrone stabilizers, amine oxide stabilizers, benzofuranone stabilizers, UV absorbers such as those of the 2-(2'-hydroxyphenyl)benzotriazole and 2-(2-hydroxyphenyl)-1,3,5-triazine classes, sterically hindered amines, metal passivators, metal oxides, organophosphorus compounds such as phosphite and phosphonite stabilizers, hydroxylamines, non-halogenated flame retardants, and mixtures thereof.
15. A process for imparting light stability and flame retardancy to an organic polymer substrate, which process comprises adding to said polymer substrate an effective flame retarding amount of at least one compound according to claim 1.
16. A molded polymer article comprising at least one compound according to claim 1.
17. Use of a compound according to claim 1 for imparting light stability and flame retardancy to an organic polymer substrate.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34233101P | 2001-12-21 | 2001-12-21 | |
| US60/342,331 | 2001-12-21 | ||
| US41655602P | 2002-10-07 | 2002-10-07 | |
| US60/416,556 | 2002-10-07 | ||
| PCT/EP2002/014135 WO2003054073A1 (en) | 2001-12-21 | 2002-12-12 | Novel flame retarding compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2467119A1 true CA2467119A1 (en) | 2003-07-03 |
| CA2467119C CA2467119C (en) | 2012-02-07 |
Family
ID=26992954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2467119A Expired - Fee Related CA2467119C (en) | 2001-12-21 | 2002-12-12 | Novel flame retarding compounds |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US6967252B2 (en) |
| EP (1) | EP1461384B1 (en) |
| JP (1) | JP4243761B2 (en) |
| KR (1) | KR101029863B1 (en) |
| CN (1) | CN1302060C (en) |
| AT (1) | ATE439401T1 (en) |
| AU (1) | AU2002358127A1 (en) |
| CA (1) | CA2467119C (en) |
| DE (1) | DE60233349D1 (en) |
| TW (1) | TWI317368B (en) |
| WO (1) | WO2003054073A1 (en) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1423465B1 (en) * | 2001-08-15 | 2009-05-27 | Ciba Holding Inc. | Flame retardant compositions |
| JP4243761B2 (en) * | 2001-12-21 | 2009-03-25 | チバ ホールディング インコーポレーテッド | New flame retardant compounds |
| US7595359B2 (en) * | 2002-06-24 | 2009-09-29 | Ciba Specialty Chemicals Corporation | Cationic alkoxyamines and their use in producing nano particles from natural or synthetic clays |
| IL153812A0 (en) * | 2003-01-06 | 2003-07-31 | Bromine Compounds Ltd | Improved wood-plastic composites |
| DE602004003500T2 (en) * | 2003-07-18 | 2007-10-04 | Ciba Speciality Chemicals Holding Inc. | FLAME-RESISTANT POLYMIC ACID |
| EP1786860B1 (en) * | 2004-09-03 | 2008-03-26 | Ciba Specialty Chemicals Holding Inc. | In-can stabilizers |
| DE102004054804A1 (en) * | 2004-11-12 | 2006-05-18 | Voith Fabrics Patent Gmbh | Paper machine clothing |
| FR2881141B1 (en) * | 2005-01-24 | 2007-02-23 | Rhodia Chimie Sa | FLAME RETARDANT COMPOSITION |
| US7888419B2 (en) * | 2005-09-02 | 2011-02-15 | Naturalnano, Inc. | Polymeric composite including nanoparticle filler |
| US8124678B2 (en) * | 2006-11-27 | 2012-02-28 | Naturalnano, Inc. | Nanocomposite master batch composition and method of manufacture |
| US8648132B2 (en) * | 2007-02-07 | 2014-02-11 | Naturalnano, Inc. | Nanocomposite method of manufacture |
| EP2125732B1 (en) * | 2007-02-21 | 2011-12-28 | Basf Se | Symmetric azo compounds in flame retardant compositions |
| WO2009029310A1 (en) * | 2007-05-23 | 2009-03-05 | Naturalnano Research, Inc. | Fire and flame retardant polymer composites |
| US20110046250A1 (en) * | 2007-07-06 | 2011-02-24 | Stowell Jeffrey K | Flame retardant composition and flexible polyurethane foam prepared therewith |
| JP5718316B2 (en) * | 2009-04-21 | 2015-05-13 | ビーエーエスエフ、パフォーマンス、プロダクツ、エルエルシー | Rotomold process for polyethylene materials |
| DK2475655T3 (en) * | 2009-09-10 | 2018-01-15 | Basf Se | STERICALLY HINDED AMIN STABILIZER |
| CN102712668A (en) * | 2010-01-15 | 2012-10-03 | 巴斯夫欧洲公司 | Phospho-substituted alkoxyamine compounds |
| CN102584689A (en) * | 2012-01-13 | 2012-07-18 | 江苏中邦制药有限公司 | Preparing method of 2-chloro-3-fluoropyridine |
| US9394483B2 (en) | 2012-05-24 | 2016-07-19 | Sabic Global Technologies B.V. | Flame retardant polycarbonate compositions, methods of manufacture thereof and articles comprising the same |
| US9023922B2 (en) | 2012-05-24 | 2015-05-05 | Sabic Global Technologies B.V. | Flame retardant compositions, articles comprising the same and methods of manufacture thereof |
| US9777206B2 (en) * | 2013-12-10 | 2017-10-03 | General Cable Technologies Corporation | Thermally conductive compositions and cables thereof |
| DE102014211276A1 (en) * | 2014-06-12 | 2015-12-17 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Use of hydroxybenzotriazole derivatives and / or hydroxyindazole derivatives as flame retardants for plastics and flame-retardant plastic molding compound |
| EP3589696B1 (en) * | 2017-03-01 | 2021-02-24 | Basf Se | Flame-retardant polyamides with pvp |
| US10723864B2 (en) * | 2017-11-17 | 2020-07-28 | International Business Machines Corporation | Flame retardant ultraviolet light stabilizing molecules |
| KR102599672B1 (en) * | 2020-11-12 | 2023-11-06 | 경기대학교 산학협력단 | Method for producing organophosphorous flame retardant, flame retardant compound prepared thereby, and flame retardant polymer resin composition comprising the same |
| CN113121778B (en) * | 2021-05-06 | 2022-08-05 | 福建师范大学泉港石化研究院 | Polyurethane flame-retardant foam material containing modified graphene and preparation method thereof |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5096950A (en) | 1988-10-19 | 1992-03-17 | Ciba-Geigy Corporation | Polyolefin compositions stabilized with NOR-substituted hindered amines |
| EP0389430B1 (en) * | 1989-03-21 | 1994-10-26 | Ciba-Geigy Ag | N-hydrocarbyloxy hindered amine light stabilizers substituted with phosphorus moieties |
| US5132426A (en) * | 1990-08-23 | 1992-07-21 | Ciba-Geigy Corporation | Substituted 3,7,9-trioxa-1-aza-2,8-diphosphaspiro(4,5)decanes and stabilized compositions |
| US5393812A (en) | 1993-08-31 | 1995-02-28 | Hercules Incorporated | Flame retardant, light stable composition |
| DE59504793D1 (en) | 1994-10-12 | 1999-02-25 | Ciba Geigy Ag | HALS phosphorinanes as stabilizers |
| TW360677B (en) * | 1994-12-22 | 1999-06-11 | Ciba Sc Holding Ag | HALS phosphoramides as stabilisers |
| EP0792911A3 (en) | 1996-02-27 | 1998-01-14 | Fmc Corporation | Flame resistant polyolefin compositions |
| AU735643B2 (en) * | 1997-06-30 | 2001-07-12 | Ciba Specialty Chemicals Holding Inc. | Flame retardant compositions |
| US5844026A (en) | 1997-06-30 | 1998-12-01 | Ciba Specialty Chemicals Corporation | N,N',N''-tris{2,4-bis Hydrocarbyloxy-2,2,6,6-tetra-methylpiperidin-4-yl)alkylamino!-s-triazin-6-yl}-3,3'-ethylenediiminodipropylamines, their isomers and bridged derivatives and polymer compositions stabilized therewith |
| ITMI980366A1 (en) * | 1998-02-25 | 1999-08-25 | Ciba Spec Chem Spa | PREPARATION OF STERICALLY PREVENTED AMINE ETHERS |
| EP1086263A4 (en) | 1998-04-20 | 2007-05-02 | Bba Nonwovens Simpsonville Inc | Nonwoven fabric having both uv stability and flame retardancy and related method for its manufacture |
| TW445276B (en) | 1998-08-13 | 2001-07-11 | Otsuka Chemical Co Ltd | Crosslinked phenoxyphosphazene compounds, process for the preparation thereof, flame retardants, flame-retardant resin compositions, and moldings of flame-retardant resins |
| US6271377B1 (en) | 1999-02-25 | 2001-08-07 | Ciba Specialty Chemicals Corporation | Hydroxy-substituted N-alkoxy hindered amines and compositions stabilized therewith |
| US6946517B2 (en) * | 1999-08-17 | 2005-09-20 | Ciba Specialty Chemicals Corporation | Stabilizer mixtures |
| DE50002160D1 (en) | 1999-11-19 | 2003-06-18 | Ciba Sc Holding Ag | Process for the selective oxidation of alcohols using easily removable nitroxyl radicals |
| US6277254B1 (en) * | 1999-12-16 | 2001-08-21 | Honeywell International Inc. | Ceramic compositions, physical vapor deposition targets and methods of forming ceramic compositions |
| TW541303B (en) * | 2000-03-22 | 2003-07-11 | Ciba Sc Holding Ag | 2,2,6,6 diethyl-dimethyl-1-alkoxy-piperidine compounds and their corresponding 1-oxides |
| TWI273115B (en) * | 2000-12-12 | 2007-02-11 | Ciba Sc Holding Ag | Improved weatherability of flame retardant polyolefin |
| JP4243761B2 (en) * | 2001-12-21 | 2009-03-25 | チバ ホールディング インコーポレーテッド | New flame retardant compounds |
| US7323502B2 (en) * | 2002-03-12 | 2008-01-29 | Ciba Specialty Chemicals Corporation | Flame retardant compositions |
| JP4324940B2 (en) * | 2002-04-17 | 2009-09-02 | チバ ホールディング インコーポレーテッド | Flame retardant polymer composition containing hydroxylamine ester |
| MY139230A (en) * | 2002-10-17 | 2009-08-28 | Ciba Holding Inc | Flame retardant polymeric electrical parts |
| US7138448B2 (en) * | 2002-11-04 | 2006-11-21 | Ciba Specialty Chemicals Corporation | Flame retardant compositions |
| DE102004018845B4 (en) * | 2003-04-25 | 2018-06-21 | Chisso Polypro Fiber Co., Ltd | Flame-resistant fiber and molded fiber part using the flame-resistant fiber |
-
2002
- 2002-12-12 JP JP2003554784A patent/JP4243761B2/en not_active Expired - Fee Related
- 2002-12-12 DE DE60233349T patent/DE60233349D1/en not_active Expired - Lifetime
- 2002-12-12 CN CNB028254937A patent/CN1302060C/en not_active Expired - Fee Related
- 2002-12-12 EP EP02791813A patent/EP1461384B1/en not_active Expired - Lifetime
- 2002-12-12 AU AU2002358127A patent/AU2002358127A1/en not_active Abandoned
- 2002-12-12 WO PCT/EP2002/014135 patent/WO2003054073A1/en active Application Filing
- 2002-12-12 KR KR1020047009031A patent/KR101029863B1/en not_active IP Right Cessation
- 2002-12-12 CA CA2467119A patent/CA2467119C/en not_active Expired - Fee Related
- 2002-12-12 AT AT02791813T patent/ATE439401T1/en not_active IP Right Cessation
- 2002-12-16 US US10/320,155 patent/US6967252B2/en not_active Expired - Fee Related
- 2002-12-19 TW TW091136624A patent/TWI317368B/en not_active IP Right Cessation
-
2005
- 2005-04-12 US US11/104,057 patent/US7531664B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| TWI317368B (en) | 2009-11-21 |
| WO2003054073A1 (en) | 2003-07-03 |
| US7531664B2 (en) | 2009-05-12 |
| US6967252B2 (en) | 2005-11-22 |
| JP2005513229A (en) | 2005-05-12 |
| US20060135659A1 (en) | 2006-06-22 |
| US20030191213A1 (en) | 2003-10-09 |
| TW200302247A (en) | 2003-08-01 |
| AU2002358127A1 (en) | 2003-07-09 |
| EP1461384B1 (en) | 2009-08-12 |
| ATE439401T1 (en) | 2009-08-15 |
| JP4243761B2 (en) | 2009-03-25 |
| CA2467119C (en) | 2012-02-07 |
| CN1606592A (en) | 2005-04-13 |
| KR20040071718A (en) | 2004-08-12 |
| EP1461384A1 (en) | 2004-09-29 |
| KR101029863B1 (en) | 2011-04-18 |
| CN1302060C (en) | 2007-02-28 |
| DE60233349D1 (en) | 2009-09-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2467119A1 (en) | Novel flame retarding compounds | |
| CA2476294A1 (en) | Flame retardant compositions | |
| US8877838B2 (en) | Melamine phenylphosphinate flame retardant compositions | |
| CA2455841A1 (en) | Flame retardant compositions | |
| JP5631392B2 (en) | Phenylphosphonate flame retardant composition | |
| JP5312607B2 (en) | Melamine phenylphosphonate flame retardant composition | |
| AU2008297195B2 (en) | Flame retardant combinations of hydroxyalkyl phosphine oxides with 1,3,5-triazines and epoxides | |
| KR20140097335A (en) | P-n-compounds as flame retardants | |
| JP2014533323A (en) | P-piperazine compounds as flame retardants | |
| EP2550321A1 (en) | Flame retardant compositions of phosphinic acid salts and nitroxyl derivatives | |
| US8771561B2 (en) | Aminoguanidinephenylphosphinate flame retardant compositions | |
| JP5349614B2 (en) | DOPO flame retardant in epoxy resin | |
| WO2013174791A1 (en) | Phosphinyliminophosphoranes as flame retardants | |
| CN102471535B (en) | Derivatives of diphosphines as flame retardants in aromatic and/or heteroaromatic epoxy resins | |
| KR20140020280A (en) | Condensation products of melamine and phenylphosphonic acid and their use as flame retardants | |
| CA2482540A1 (en) | Flame retardant polymer compositions containing hydroxylamine esters | |
| JP2013532749A (en) | Phosphinic hydrazide flame retardant composition | |
| KR20160138037A (en) | Heptaphosphorus-derived compounds as flame retardants | |
| WO2010133570A1 (en) | Guanidine phenylphosphinate flame retardant compositions | |
| NH-II | Melamine phenylphosphinate flame retardant compositions |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20151214 |