WO1999047597A1 - Synergist for flame retardant nylons - Google Patents
Synergist for flame retardant nylons Download PDFInfo
- Publication number
- WO1999047597A1 WO1999047597A1 PCT/US1999/005902 US9905902W WO9947597A1 WO 1999047597 A1 WO1999047597 A1 WO 1999047597A1 US 9905902 W US9905902 W US 9905902W WO 9947597 A1 WO9947597 A1 WO 9947597A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- polyamide
- flame retardant
- molding
- antimony
- Prior art date
Links
- 239000003063 flame retardant Substances 0.000 title claims abstract description 11
- 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 abstract description 10
- 229920001778 nylon Polymers 0.000 title description 8
- 239000000203 mixture Substances 0.000 claims abstract description 22
- 239000004952 Polyamide Substances 0.000 claims abstract description 19
- 229920002647 polyamide Polymers 0.000 claims abstract description 19
- 238000000465 moulding Methods 0.000 claims abstract description 10
- 239000012760 heat stabilizer Substances 0.000 claims abstract description 7
- 238000002844 melting Methods 0.000 claims abstract description 7
- 230000008018 melting Effects 0.000 claims abstract description 7
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000011256 inorganic filler Substances 0.000 claims abstract description 5
- 229910003475 inorganic filler Inorganic materials 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 10
- 239000011521 glass Substances 0.000 claims description 6
- 239000003365 glass fiber Substances 0.000 claims description 5
- 239000004793 Polystyrene Substances 0.000 claims description 4
- 229920002223 polystyrene Polymers 0.000 claims description 4
- PGGROMGHWHXWJL-UHFFFAOYSA-N 4-(azepane-1-carbonyl)benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C(=O)N1CCCCCC1 PGGROMGHWHXWJL-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000005995 Aluminium silicate Substances 0.000 claims description 2
- 229920000049 Carbon (fiber) Polymers 0.000 claims description 2
- 235000012211 aluminium silicate Nutrition 0.000 claims description 2
- 239000011324 bead Substances 0.000 claims description 2
- 239000004917 carbon fiber Substances 0.000 claims description 2
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 claims description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 2
- 239000010445 mica Substances 0.000 claims description 2
- 229910052618 mica group Inorganic materials 0.000 claims description 2
- 229920006122 polyamide resin Polymers 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- DJZKNOVUNYPPEE-UHFFFAOYSA-N tetradecane-1,4,11,14-tetracarboxamide Chemical compound NC(=O)CCCC(C(N)=O)CCCCCCC(C(N)=O)CCCC(N)=O DJZKNOVUNYPPEE-UHFFFAOYSA-N 0.000 claims description 2
- 239000010456 wollastonite Substances 0.000 claims description 2
- 229910052882 wollastonite Inorganic materials 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 description 6
- 239000004677 Nylon Substances 0.000 description 5
- 229920002302 Nylon 6,6 Polymers 0.000 description 5
- 150000001463 antimony compounds Chemical class 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920002292 Nylon 6 Polymers 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920003182 Surlyn® Polymers 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- -1 hexamethylene dodecamide Chemical compound 0.000 description 2
- 229920006139 poly(hexamethylene adipamide-co-hexamethylene terephthalamide) Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000012744 reinforcing agent Substances 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- MXAOILAHPVJWBS-UHFFFAOYSA-N 10-(azepan-1-yl)-10-oxodecanamide Chemical compound NC(=O)CCCCCCCCC(=O)N1CCCCCC1 MXAOILAHPVJWBS-UHFFFAOYSA-N 0.000 description 1
- FQLAJSQGBDYBAL-UHFFFAOYSA-N 3-(azepane-1-carbonyl)benzamide Chemical compound NC(=O)C1=CC=CC(C(=O)N2CCCCCC2)=C1 FQLAJSQGBDYBAL-UHFFFAOYSA-N 0.000 description 1
- WUIAYLSDSVSPRW-UHFFFAOYSA-N 4-(3-methylpiperidine-1-carbonyl)benzamide Chemical compound C1C(C)CCCN1C(=O)C1=CC=C(C(N)=O)C=C1 WUIAYLSDSVSPRW-UHFFFAOYSA-N 0.000 description 1
- 239000004953 Aliphatic polyamide Substances 0.000 description 1
- 239000004609 Impact Modifier Substances 0.000 description 1
- 239000005035 Surlyn® Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229920003231 aliphatic polyamide Polymers 0.000 description 1
- 229910000410 antimony oxide Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 229960001545 hydrotalcite Drugs 0.000 description 1
- 229910001701 hydrotalcite Inorganic materials 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical class [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- NSBGJRFJIJFMGW-UHFFFAOYSA-N trisodium;stiborate Chemical compound [Na+].[Na+].[Na+].[O-][Sb]([O-])([O-])=O NSBGJRFJIJFMGW-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/38—Boron-containing 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
-
- 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
- C08K5/02—Halogenated hydrocarbons
- C08K5/03—Halogenated hydrocarbons aromatic, e.g. C6H5-CH2-Cl
-
- 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
- C08K3/38—Boron-containing compounds
- C08K2003/387—Borates
Definitions
- the invention relates to polyamide molding compositions having improved flame resistance. More particularly, the invention relates to antimony- free polyamide compositions with superior physical properties. Description of Prior Art
- antimony compounds antimony oxides and sodium antimonate
- Industry has been trying for years to eliminate the toxic heavy metal antimony in flame retardant compositions, but has been unable to develop anything nearly as effective as antimony compounds.
- zinc borate could be used as a direct (equally effective) replacement for antimony compounds in polyamide compositions.
- Another unexpected side benefit of this discovery is a significant improvement in physical properties (i.e. tensile strength and elongation to break) by using the zinc borate as a synergist.
- antimony-free polyamide molding compositions with improved flame resistance comprising, in weight percent, (a) 20 - 77% polyamide, having a melting point of 215 - 340°C,
- the polyamide used in this invention may be 20-77% (all percentages are weight percent unless designated otherwise) of any polyamide that has a melting point of from about 215°C to about 340°C.
- An example of a suitable polyamide is a copolyamide composed of 20-80 mole % of units derived from hexamethylene terephthalamide and 80-20 mole % of units derived from hexamethylene adipamide. This polyamide is referred to hereinafter as 6T/66 copolymer.
- polystyrene resin examples include polyamides composed of 20-80 mole % of units derived from hexamethylene terephthalamide and 80-20 mole % of units derived from hexamethylene sebacamide, hexamethylene dodecamide, hexamethylene isophthalamide, 2-methylpentamethylene terephthalamide, or mixtures thereof.
- Synthetic polyamide includes a polymer which is made by man, and does not include natural fibers such as wools or silks.
- an “aliphatic polyamide” is meant a polymer which has repeat units which include amide groups in the main chain, and in which at least some, preferably at least 50 mole percent, of these amide groups (through the nitrogen atoms and/or carbonyl carbon atoms of the amide groups) are connected to aliphatic carbon atoms.
- Preferred polyamides include nylon-6,6, nylon-6, nylon 6,12, and copolymers of nylon-6,6 and nylon 6.
- Nylon-6,6 and nylon-6, and copolymers thereof, are especially preferred and nylon-6,6 is more preferred.
- copolyamide used in the composition of the present invention. It may be produced easily by ordinary melt polymerization.
- One method to produce the copolymer of this invention is an autoclave one-step polymerization process taught in US Patent No. 5,378,800 which is incorporated by reference herein. That process includes feeding to a reactor an aqueous salt solution of an admixture of desired diacids and diamines, heating the solution under pressure, reducing the pressure, maintaining the reaction mixture at a pressure that is not greater than about atmospheric pressure, and discharging the polyamide from the reactor.
- An alternative process includes preparing a prepolymer and subjecting the prepolymer to solid-phase polymerization or melt-mixing in an extruder to increase the degree of polymerization.
- the prepolymer is prepared by heating at 150°C-320°C an aqueous solution containing 6T salt (a salt formed from hexamethylenediamine and terephthalic acid) and 66 salt (a salt formed from hexamethylenediamine and adipic acid).
- 6T salt a salt formed from hexamethylenediamine and terephthalic acid
- 66 salt a salt formed from hexamethylenediamine and adipic acid
- the composition of the present invention contains 10-60% of an inorganic filler or reinforcing agent that includes, for example, fibrous reinforcement such as glass fiber and carbon fiber, glass beads, talc, kaolin, wollastonite and mica.
- fibrous reinforcement such as glass fiber and carbon fiber
- glass beads Preferable among them is glass fiber.
- Glass fibers suitable for use in the present invention are those generally used as a reinforcing agent for thermoplastics resins and thermosetting resins.
- Preferred glass fiber is in the form of glass rovings, glass chopped strands, and glass yarn made of continuous glass filaments 3-20 micron meters in diameter.
- the resin composition of the present invention contains 10-35% of a flame retardant. It is a flame retardant based on brominated polystyrene and/or brominated poly-phenylene ether containing 50-70%) by weight bromine.
- the polystyrene has a weight-average molecular weight higher than 5000, preferably higher than 20,000, and more preferably higher than 28,000.
- the ether has a molecular weight of at least 6000.
- a preferred flame retardant is brominated polystyrene or polydibromostyrene.
- the present compositions comprise 3-10% zinc borate, but no antimony compounds.
- copolyamide resin of the present invention may have incorporated in it a variety of additives such as an impact modifier, a viscosity modifier, pigment, dye, antioxidant, and heat resistance improver, in such amounts that they do not harm its characteristic properties.
- the copolyamide resins of the present invention may include up to 5% of color concentrate (such as carbon black) as well as up to 1% of lubricant. Drip suppressants may also be present in amounts of up to 5%.
- the flammability rating was conducted using UL Test No. UL-94 dated April 19, 1995.
- Surlyn® is ethylene copolymer ionomer by E. I. DuPont, Wilmington, Delaware
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2000536785A JP2002506905A (en) | 1998-03-18 | 1999-03-18 | Synergists for flame retardant nylon |
CA002322286A CA2322286A1 (en) | 1998-03-18 | 1999-03-18 | Synergist for flame retardant nylons |
EP99912654A EP1068263A1 (en) | 1998-03-18 | 1999-03-18 | Synergist for flame retardant nylons |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US7839298P | 1998-03-18 | 1998-03-18 | |
US60/078,392 | 1998-03-18 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1999047597A1 true WO1999047597A1 (en) | 1999-09-23 |
Family
ID=22143764
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1999/005902 WO1999047597A1 (en) | 1998-03-18 | 1999-03-18 | Synergist for flame retardant nylons |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP1068263A1 (en) |
JP (1) | JP2002506905A (en) |
CA (1) | CA2322286A1 (en) |
WO (1) | WO1999047597A1 (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100406522C (en) * | 2004-01-30 | 2008-07-30 | 三井化学株式会社 | Flame-retardant polyamide composition and its use |
US7816438B2 (en) | 2005-04-08 | 2010-10-19 | Mitsui Chemicals, Inc. | Flame-retardant polyamide composition |
WO2014135624A1 (en) * | 2013-03-07 | 2014-09-12 | Basf Se | Heat conducting thermoplastic moulding compositions comprising a flame retardant |
US20140288220A1 (en) * | 2013-03-25 | 2014-09-25 | E I Du Pont De Nemours And Company | Heat resistant polyamide compositions |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE443734T1 (en) * | 2006-01-26 | 2009-10-15 | Dsm Ip Assets Bv | FLAME RETARDANT POLYAMIDE MOLDING COMPOSITION |
AU2009281930B2 (en) * | 2008-08-15 | 2015-03-12 | Invista Technologies S. Ar. L. | Flame retardant polymer composites, fibers, carpets, and methods of making each |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0055893A2 (en) * | 1980-12-31 | 1982-07-14 | E.I. Du Pont De Nemours And Company | Flame-retardant polyamide compositions |
EP0122699A2 (en) * | 1983-03-17 | 1984-10-24 | Imperial Chemical Industries Plc | Flame retardant polyamide compositions |
EP0410301A1 (en) * | 1989-07-27 | 1991-01-30 | BASF Aktiengesellschaft | Flame resistant thermoplastic mouldings |
-
1999
- 1999-03-18 EP EP99912654A patent/EP1068263A1/en not_active Withdrawn
- 1999-03-18 WO PCT/US1999/005902 patent/WO1999047597A1/en not_active Application Discontinuation
- 1999-03-18 CA CA002322286A patent/CA2322286A1/en not_active Abandoned
- 1999-03-18 JP JP2000536785A patent/JP2002506905A/en active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0055893A2 (en) * | 1980-12-31 | 1982-07-14 | E.I. Du Pont De Nemours And Company | Flame-retardant polyamide compositions |
EP0122699A2 (en) * | 1983-03-17 | 1984-10-24 | Imperial Chemical Industries Plc | Flame retardant polyamide compositions |
EP0410301A1 (en) * | 1989-07-27 | 1991-01-30 | BASF Aktiengesellschaft | Flame resistant thermoplastic mouldings |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100406522C (en) * | 2004-01-30 | 2008-07-30 | 三井化学株式会社 | Flame-retardant polyamide composition and its use |
US7816438B2 (en) | 2005-04-08 | 2010-10-19 | Mitsui Chemicals, Inc. | Flame-retardant polyamide composition |
WO2014135624A1 (en) * | 2013-03-07 | 2014-09-12 | Basf Se | Heat conducting thermoplastic moulding compositions comprising a flame retardant |
US20140288220A1 (en) * | 2013-03-25 | 2014-09-25 | E I Du Pont De Nemours And Company | Heat resistant polyamide compositions |
Also Published As
Publication number | Publication date |
---|---|
CA2322286A1 (en) | 1999-09-23 |
JP2002506905A (en) | 2002-03-05 |
EP1068263A1 (en) | 2001-01-17 |
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