CA1109182A - Flame retardant composition of poly-phenylene ether, styrene resin and cyclic phosphate - Google Patents
Flame retardant composition of poly-phenylene ether, styrene resin and cyclic phosphateInfo
- Publication number
- CA1109182A CA1109182A CA310,441A CA310441A CA1109182A CA 1109182 A CA1109182 A CA 1109182A CA 310441 A CA310441 A CA 310441A CA 1109182 A CA1109182 A CA 1109182A
- Authority
- CA
- Canada
- Prior art keywords
- composition
- carbon atoms
- parts
- styrene resin
- 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.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/04—Homopolymers or copolymers of styrene
- C08L25/06—Polystyrene
-
- 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
- C08K5/527—Cyclic esters
Abstract
ABSTRACT OF THE DISCLOSURE
Flame retardant compositions comprising a polyphenylene ether resin, a styrene resin and a cyclic phosphate have excellent appearance and physical properties after molding. Especially useful is diphenyl penta-erythritol diphosphate.
Flame retardant compositions comprising a polyphenylene ether resin, a styrene resin and a cyclic phosphate have excellent appearance and physical properties after molding. Especially useful is diphenyl penta-erythritol diphosphate.
Description
z 8 C~l 2557 A
-~ ~omposotions comprising a polyphenylene ether resin and a styrene resin ~re well known as useful engineering thermoplastics, for molding, extrusion and the like. They are described in U.S. Patent 3,383,435 -dated May 14, 1968 - Cizek.
Such compositions are normally flammable, particularly if high proportions of styrene resin are present, and aromatic phosphate compounds, e.g., triphenyl phosphate are used to retard or eliminate flammability.
U.S. Patent No. 3,639,506 - dated February 1, 1972 - Haaf, discloses that triphenyl phosphate has a tendency to reduce physical properties and describes the use of combinations of aromatic phosphates and aromatic halogen compounds to flame retard the composition, without markedly lowering resistance to distortion by heat.
Pentaerythritol esters of phosphoric acid have been reported in Wahl et al, U.S. Patent No. 3,090,799 -dated May 21, 1963 - Wahl et al, to be generally superior as plasticizers and as flame retardants for synthetic resins. However, it is disclosed that from 5 to 40 parts of the said phosphate per 100 parts of the resin is the proper amount to use, and all of the working examples appear to fall in the range of 5 to 43 parts of the said cyclic phosphate per 100 parts of the combination, by weight.
It has now been discovered that cyclic phosphate compounds by themselves are effective non-plasticizing flame retardant additives for the compositions of polyphenylene ethers and styrene resins, at an unexpectedly lower concentration. Moreover, such cyclic phosphate materials are just as effective in flame retardance in this system as triphenyl phosphate and provide compositions - 1 - ~
~ C~l ~557 with substantially the same impact resistance as the polymer composition itself.
According to this invention there are provided flame retardant compositions comprising (a) a normally flammable composition comprising a polyphenylene ether resin and a styrene resin, and (b) an effective, flame-retardant amount of a compound of the formula 11 / \ / \ ~
R _ O _P C P - O - R
/ \
wherein R is alkyl of from 1 to 18 carbon atoms, aryl or alkaryl.
Preferred compositions are those in which the polyphenylene ether resin is of the formula Rl 20 wherein the oxygen ether atom of one unit is connected to the benzene nucleaus of the next adjoining unit, n is a positive integer equal to at least 50; and R , is a monovalent substituent selected from hydrogen, halogen, hydrocarbon radicals free of a tertiary alpha carbon atom, halohydrocarbon radicals having at least two carbon atoms between the halogen atom and the phenyl nucleus and being free of a tertiary alpha carbon atom, hydrocarbonoxy radicals being free of a tertiary alpha carbon atom, or halohydrocarbonoxy radicals having at least two carbon atoms between the halogen atom and the phenyl nucleus and being free of a tertiary alpha carbon atom. Especially preferred resins are those in which R is alkyl of from 1 ?~ 2 8 C~l 2557 to 6 carbon atoms, especially methyl.
Special mention is made of compositions wherein each Rl is alkyl of from 1 to 6 carbon atoms. The component (a) can be made by those skilled in the art following the teachings of the above-mentioned Cize'c patent, and the other references mentioned therein. These materials are also commercially available, e.g., from the General Electric Co., Pittsfield, Mass.
Preferred compositions also include those in which the styrene resin has at least 25 percent by weight units derived from a compound of the formula:
R C = CH2 ~~ (~)P
~ .
wherein R is hydrogen, alkyl of from 1 to 6 carbon atoms or halogen; Z is vinyl, halogen, or lower alkyl, and p is 0 or a whole number equal to the number of replaceable hydrogen atoms in the benzene nucleus. Preferred such styrene resins will be those in which p is 0 and R is hydrogen. Typical styrene resins include, by way of example, homopolymers such as polystyrene and polychlorostyrene, the modified polystyrenes such as rubber modified polystyrenes (high impact polystyrenes), and the styrene containing copolymers, such as the styrene-acrylonitrile copolymers (SAN), styrene-butadiene copolymers, styrene/
ethylene -propylene-butadiene terpolymers (EPDM), styrene maleic anhydride copolymers (SMA), styrene-acrylonitrile-alpha-alkyl styrene copolymers, styrene-acrylonitrile-butadene terpolymers (ABS), poly-alpha-methyl styrene, copolymers of ethyl-vinyl benzene and divinyl benzene, and ~ Z 8 C~l 2557 the like.
The flame retardant cyclic phosphates will include compounds wherein R is straight or branched-chain alkyl of from about 1 to about 18 carbon atoms, e.g., methyl, ethyl, propyl, i-propyl, _-decyl, hexadecyl, octadecyl, and the like; aryl, e.g., phenyl, naphthyl, and the like, or alkaryl, e.g., benzyl phenethyl, and the like, containing up to about 18 carbon atoms. Preferably, in the cyclic phosphate, R will be methyl, decyl and, expecially preferably phenyl.
The cyclic phosphates can be made by those skilled in the art, e.g., by following the procedure hereinafter, or in the above-mentioned Wahl et al patent, U.S.
3,090,799 - dated May 21, 1963.
The manner of adding the flame retardant component (b) to the composition (a) is not critical. Preferably, however, such component is added as part of a blend premix, the latter being passed through an extruder with extrusion temperature being maintained between about 450 and 640F
depending on the composition. The strands emerging from the extruder may be cooled, chopped into pellets, chopped into pellets and molded to a desired shape.
The concentration of the flame retardant additive (b) can vary, but is dependent to a large extent on the concentration of the styrene resin and the particular styrene resin used. Lower concentrations of styrene resin or less flammable styrene resins require a lower concentration of flame retardant. Moreover, cyclic phosphates which higher contents of phosphorous can be used in lower amounts. In general, however, amounts of from about 1 to about 10 parts by weight of component (b) can be used. However, to secure the major advantages, only : . :
~ fl ~ll 2557 from about 2 to about 4.5 parts per lO0 parts by wcight of (a) and (b) combines will be used in compositions Eor molding -- as contrasted to film-casting.
Conventional additives, e.g., reinforcements, pigments, stabilizers, lubricants, and the like can also be included in conventional amounts.
The following examples illustrate the present invention. In each report, flame retardant properties are determined following procedures established by the Underwriters' Laboratory Bulletin, No.94. To meet a V-l rating, bars measuring 2-1/2" x 1/2" x 1/8" thick are twice ignited for 10 seconds each time. The compositions shall:
A. Not have any specimens which burn with flaming combustion for more than 30 seconds after each application of the test flame.
B. Not have a total flaming combustion time exceeding 250 seconds for the lO flame applications for each set of 5 specimens.
C. Not have any specimens which burn with flaming or glowing combustion up to the holding clamp.
D. Not have any specimens which drip flaming particles that ignite the dry absorbent surgical cotton located 12 inches (305 mm) below the test specimen.
E. Not have any specimens with glowing combustion which persists beyond 60 seconds after the second removal of the test flame.
EX~MPLES 1 - 3 .
Compositions comprising polyphenylene ether resin, polystyrene resin and a cyclic phosphate of the formula ~ 2 8 C~l 2557 O O - CH2 / 2 \ ~
R ~O P C P ~O R
\ _ / \ /
are preblended, extruded at 530F and chopped into molding granules. The granules are injection molded at 500F
tcylinder) and 180F (mold) in a 3 oz. Newbury injection molding maching.
Physical properties and burn test results for these and for comparison examples are set forth in the Table:
TABLE. - Compositions Comprising Polyphenylene ~ Ether, Styrene Resin And Cyclic Phosphate Example 1 lA* lB*
Com~ition (pts.per hundred wt.) Poly(2,6-dimethyl-1,4-phenylene) ethera 35 35 35 Polystyrene resinb 65 65 65 Cyclic phosphate R = C H c 4.5 __ __ Triphenyl phosphated -- 7 --PROPERTIES
Heat distortion temp. at 266 psi, F. 233 197 230 Izod impact, ft.-lbs./in.notch 4.0 4.7 3.6 Gardner impact, in.-lbs. 130 170 110 Melt viscosity at 1500 sec. 1 1520 1270 1550 Uh 94 Rating V-l V-l Burns * Control a PPO, General Electric Co.
f~l b FG 834 rubber modified polystyrene, Foster Grant Co.
c See procedure below.
d Conventional, plasticizing flame retarding agent ~ 2 ~ ~'ll 2~57 PROCEDURE
Pentaerythritol, 136 g., is introduced into 500 cc. of phosphorus oxychloride and heated on a steam bath. The pentaerythritol is completely dissolved over 30-45 minutes, with evolution of hydrogen chloride, the pentaerythritol ester of phosphorochloridic acid crystallizing out~ The bulk of the phosphorus oxychloride is evaporated in a vacuum and the crystals are washed with methylene chloride. The ester, 300 g., and 220 g. of phenol are heated under reflux in 2 liters of methylene chloride after adding 100 cc. of triethylamine. The methylene chloride is distilled off, the residue is extracted with a mixture of water and methylene chloride. The amine salt is transferred to the aqueous phase and the phosphoric acid ester product transfers to the methylene chloride phase.
The methylene chloride solution is separated, the solvent is evaporated off, and the residue comprises the product of the formula.
l~ /~ \ / 2 \ j!
6 5 C P _ OC6H5 \ O _ CH2 2 If the procedure is repeated, substituting for phenol, respectively, p-cresol, absolute ethanol, and octadecyl alcohol, correspondingly substituted pentaerythritol esters will be obtained.
These can be employed in combination with polyphenylene ether and styrene resins as set forth in the Example and efficiently flame retarded compositions according to this invention will be obtained.
Many ~ariations will suggest themselves to those skilled in this art in the li~ht of the above-detailed ~ C~l ~557 description. All such obvious variations are within the full intended scope of the invention as defined by the appended claims.
-~ ~omposotions comprising a polyphenylene ether resin and a styrene resin ~re well known as useful engineering thermoplastics, for molding, extrusion and the like. They are described in U.S. Patent 3,383,435 -dated May 14, 1968 - Cizek.
Such compositions are normally flammable, particularly if high proportions of styrene resin are present, and aromatic phosphate compounds, e.g., triphenyl phosphate are used to retard or eliminate flammability.
U.S. Patent No. 3,639,506 - dated February 1, 1972 - Haaf, discloses that triphenyl phosphate has a tendency to reduce physical properties and describes the use of combinations of aromatic phosphates and aromatic halogen compounds to flame retard the composition, without markedly lowering resistance to distortion by heat.
Pentaerythritol esters of phosphoric acid have been reported in Wahl et al, U.S. Patent No. 3,090,799 -dated May 21, 1963 - Wahl et al, to be generally superior as plasticizers and as flame retardants for synthetic resins. However, it is disclosed that from 5 to 40 parts of the said phosphate per 100 parts of the resin is the proper amount to use, and all of the working examples appear to fall in the range of 5 to 43 parts of the said cyclic phosphate per 100 parts of the combination, by weight.
It has now been discovered that cyclic phosphate compounds by themselves are effective non-plasticizing flame retardant additives for the compositions of polyphenylene ethers and styrene resins, at an unexpectedly lower concentration. Moreover, such cyclic phosphate materials are just as effective in flame retardance in this system as triphenyl phosphate and provide compositions - 1 - ~
~ C~l ~557 with substantially the same impact resistance as the polymer composition itself.
According to this invention there are provided flame retardant compositions comprising (a) a normally flammable composition comprising a polyphenylene ether resin and a styrene resin, and (b) an effective, flame-retardant amount of a compound of the formula 11 / \ / \ ~
R _ O _P C P - O - R
/ \
wherein R is alkyl of from 1 to 18 carbon atoms, aryl or alkaryl.
Preferred compositions are those in which the polyphenylene ether resin is of the formula Rl 20 wherein the oxygen ether atom of one unit is connected to the benzene nucleaus of the next adjoining unit, n is a positive integer equal to at least 50; and R , is a monovalent substituent selected from hydrogen, halogen, hydrocarbon radicals free of a tertiary alpha carbon atom, halohydrocarbon radicals having at least two carbon atoms between the halogen atom and the phenyl nucleus and being free of a tertiary alpha carbon atom, hydrocarbonoxy radicals being free of a tertiary alpha carbon atom, or halohydrocarbonoxy radicals having at least two carbon atoms between the halogen atom and the phenyl nucleus and being free of a tertiary alpha carbon atom. Especially preferred resins are those in which R is alkyl of from 1 ?~ 2 8 C~l 2557 to 6 carbon atoms, especially methyl.
Special mention is made of compositions wherein each Rl is alkyl of from 1 to 6 carbon atoms. The component (a) can be made by those skilled in the art following the teachings of the above-mentioned Cize'c patent, and the other references mentioned therein. These materials are also commercially available, e.g., from the General Electric Co., Pittsfield, Mass.
Preferred compositions also include those in which the styrene resin has at least 25 percent by weight units derived from a compound of the formula:
R C = CH2 ~~ (~)P
~ .
wherein R is hydrogen, alkyl of from 1 to 6 carbon atoms or halogen; Z is vinyl, halogen, or lower alkyl, and p is 0 or a whole number equal to the number of replaceable hydrogen atoms in the benzene nucleus. Preferred such styrene resins will be those in which p is 0 and R is hydrogen. Typical styrene resins include, by way of example, homopolymers such as polystyrene and polychlorostyrene, the modified polystyrenes such as rubber modified polystyrenes (high impact polystyrenes), and the styrene containing copolymers, such as the styrene-acrylonitrile copolymers (SAN), styrene-butadiene copolymers, styrene/
ethylene -propylene-butadiene terpolymers (EPDM), styrene maleic anhydride copolymers (SMA), styrene-acrylonitrile-alpha-alkyl styrene copolymers, styrene-acrylonitrile-butadene terpolymers (ABS), poly-alpha-methyl styrene, copolymers of ethyl-vinyl benzene and divinyl benzene, and ~ Z 8 C~l 2557 the like.
The flame retardant cyclic phosphates will include compounds wherein R is straight or branched-chain alkyl of from about 1 to about 18 carbon atoms, e.g., methyl, ethyl, propyl, i-propyl, _-decyl, hexadecyl, octadecyl, and the like; aryl, e.g., phenyl, naphthyl, and the like, or alkaryl, e.g., benzyl phenethyl, and the like, containing up to about 18 carbon atoms. Preferably, in the cyclic phosphate, R will be methyl, decyl and, expecially preferably phenyl.
The cyclic phosphates can be made by those skilled in the art, e.g., by following the procedure hereinafter, or in the above-mentioned Wahl et al patent, U.S.
3,090,799 - dated May 21, 1963.
The manner of adding the flame retardant component (b) to the composition (a) is not critical. Preferably, however, such component is added as part of a blend premix, the latter being passed through an extruder with extrusion temperature being maintained between about 450 and 640F
depending on the composition. The strands emerging from the extruder may be cooled, chopped into pellets, chopped into pellets and molded to a desired shape.
The concentration of the flame retardant additive (b) can vary, but is dependent to a large extent on the concentration of the styrene resin and the particular styrene resin used. Lower concentrations of styrene resin or less flammable styrene resins require a lower concentration of flame retardant. Moreover, cyclic phosphates which higher contents of phosphorous can be used in lower amounts. In general, however, amounts of from about 1 to about 10 parts by weight of component (b) can be used. However, to secure the major advantages, only : . :
~ fl ~ll 2557 from about 2 to about 4.5 parts per lO0 parts by wcight of (a) and (b) combines will be used in compositions Eor molding -- as contrasted to film-casting.
Conventional additives, e.g., reinforcements, pigments, stabilizers, lubricants, and the like can also be included in conventional amounts.
The following examples illustrate the present invention. In each report, flame retardant properties are determined following procedures established by the Underwriters' Laboratory Bulletin, No.94. To meet a V-l rating, bars measuring 2-1/2" x 1/2" x 1/8" thick are twice ignited for 10 seconds each time. The compositions shall:
A. Not have any specimens which burn with flaming combustion for more than 30 seconds after each application of the test flame.
B. Not have a total flaming combustion time exceeding 250 seconds for the lO flame applications for each set of 5 specimens.
C. Not have any specimens which burn with flaming or glowing combustion up to the holding clamp.
D. Not have any specimens which drip flaming particles that ignite the dry absorbent surgical cotton located 12 inches (305 mm) below the test specimen.
E. Not have any specimens with glowing combustion which persists beyond 60 seconds after the second removal of the test flame.
EX~MPLES 1 - 3 .
Compositions comprising polyphenylene ether resin, polystyrene resin and a cyclic phosphate of the formula ~ 2 8 C~l 2557 O O - CH2 / 2 \ ~
R ~O P C P ~O R
\ _ / \ /
are preblended, extruded at 530F and chopped into molding granules. The granules are injection molded at 500F
tcylinder) and 180F (mold) in a 3 oz. Newbury injection molding maching.
Physical properties and burn test results for these and for comparison examples are set forth in the Table:
TABLE. - Compositions Comprising Polyphenylene ~ Ether, Styrene Resin And Cyclic Phosphate Example 1 lA* lB*
Com~ition (pts.per hundred wt.) Poly(2,6-dimethyl-1,4-phenylene) ethera 35 35 35 Polystyrene resinb 65 65 65 Cyclic phosphate R = C H c 4.5 __ __ Triphenyl phosphated -- 7 --PROPERTIES
Heat distortion temp. at 266 psi, F. 233 197 230 Izod impact, ft.-lbs./in.notch 4.0 4.7 3.6 Gardner impact, in.-lbs. 130 170 110 Melt viscosity at 1500 sec. 1 1520 1270 1550 Uh 94 Rating V-l V-l Burns * Control a PPO, General Electric Co.
f~l b FG 834 rubber modified polystyrene, Foster Grant Co.
c See procedure below.
d Conventional, plasticizing flame retarding agent ~ 2 ~ ~'ll 2~57 PROCEDURE
Pentaerythritol, 136 g., is introduced into 500 cc. of phosphorus oxychloride and heated on a steam bath. The pentaerythritol is completely dissolved over 30-45 minutes, with evolution of hydrogen chloride, the pentaerythritol ester of phosphorochloridic acid crystallizing out~ The bulk of the phosphorus oxychloride is evaporated in a vacuum and the crystals are washed with methylene chloride. The ester, 300 g., and 220 g. of phenol are heated under reflux in 2 liters of methylene chloride after adding 100 cc. of triethylamine. The methylene chloride is distilled off, the residue is extracted with a mixture of water and methylene chloride. The amine salt is transferred to the aqueous phase and the phosphoric acid ester product transfers to the methylene chloride phase.
The methylene chloride solution is separated, the solvent is evaporated off, and the residue comprises the product of the formula.
l~ /~ \ / 2 \ j!
6 5 C P _ OC6H5 \ O _ CH2 2 If the procedure is repeated, substituting for phenol, respectively, p-cresol, absolute ethanol, and octadecyl alcohol, correspondingly substituted pentaerythritol esters will be obtained.
These can be employed in combination with polyphenylene ether and styrene resins as set forth in the Example and efficiently flame retarded compositions according to this invention will be obtained.
Many ~ariations will suggest themselves to those skilled in this art in the li~ht of the above-detailed ~ C~l ~557 description. All such obvious variations are within the full intended scope of the invention as defined by the appended claims.
Claims (20)
1. A flame retardant composition comprising (a) a normally flammable composition comprising a polyphenylene ether resin and a styrene resin, and (b) an effective, flame-retardant amount of a compound of the formula wherein R is alkyl of from 1 to 18 carbon atoms, aryl or alkaryl.
2. A composition as defined in Claim 1 wherein said polyphenylene ether resin is of the formula wherein the oxygen ether atom of one unit is connected to the benzene nucleus of the next adjoining unit, n is a positive integer equal to at least 50; and R1, independently, is a monovalent substituent selected from hydrogen, halogen, hydrocarbon radicals free of a tertiary alpha carbon atom, halohydrocarbon radicals having at least two carbon atoms between the halogen atom and the phenyl nucleus and being free of a tertiary alpha carbon atom, hydrocarbonoxy radicals being free of a tertiary alpha carbon atom, or halohydrocarbonoxy radicals having at least two carbon atoms between the halogen atom and the phenyl nucleus and being free of a tertiary alpha carbon atom.
3. A composition as defined in claim 2 wherein each R1 is alkyl of from 1 to 6 carbon atoms.
4. A composition as defined in claim 3 wherein each R1 is methyl.
5. A composition as defined in claim 1 wherein the styrene resin comprises from 20 to 80 parts by weight per 100 parts by weight of component (a).
6. A composition as defined in claim 1 wherein said styrene resin has at least 25 percent by weight units derived from a compound of the formula:
wherein R2 is hydrogen, alkyl of from 1 to 6 carbon atoms or halogen; Z is vinyl, halogen, or lower alkyl, and p is 0 or a whole number equal to the number of replaceable hydrogen atoms in the benzene nucleus.
wherein R2 is hydrogen, alkyl of from 1 to 6 carbon atoms or halogen; Z is vinyl, halogen, or lower alkyl, and p is 0 or a whole number equal to the number of replaceable hydrogen atoms in the benzene nucleus.
7. A composition as defined in claim 6 wherein p is 0 and R2 is hydrogen.
8. A composition as defined in claim 1 wherein, in component (b), R is phenyl.
9. A composition as defined in claim 1 wherein the amount of component (b) is from 1 to 10 parts by weight per 100 parts by weight of (a) and (b) combined.
10. A process for decreasing the self-extinguishing time of a normally flammable composition comprising a polyphenylene ether resin and a styrene resin, said process comprising adding to said composition an effective flame-retardant amount of a flame-retardant of the formula wherein R is alkyl of from 1 to 18 carbon atoms, aryl or alkaryl.
11. A process as defined in claim 10 wherein said polyphenylene ether resin is of the formula wherein the oxygen ether atom of one unit is connected to the benzene nucleus of the next adjoining unit, n is a positive integer equal to at least 50; and R1, independently, is a monovalent substituent selected from hydrogen, halogen, hydrocarbon radicals free of a tertiary alpha carbon atom, halohydrocarbon radicals having at least two carbon atoms between the halogen atom and the phenyl nucleus and being free of a tertiary alpha carbon atom, hydrocarbonoxy radicals being free of a tertiary alpha carbon atom, or halohydrocarbonoxy radicals having at least two carbon atoms between the halogen atom and the phenyl nucleus and being free of a tertiary alpha carbon atom.
12. A process as defined in claim 11 wherein each is alkyl of from 1 to 6 carbon atoms.
13. A process as defined in claim 12 wherein each is methyl.
14. A process as defined in claim 10 wherein the styrene resin comprises from 20 to 80 parts by weight per 100 parts by weight of polyphenylene ether resin and styrene resin.
15. A process as defined in claim 10 wherein said styrene resin has at least 25 percent by weight units derived from a compound of the formula wherein R2 is hydrogen, alkyl of from 1 to 6 carbon atoms or halogen; Z is vinyl, halogen, or lower alkyl, and p is 0 or a whole number equal to the number of replaceable hydrogen atoms in the benzene nucleus.
16. A process as defined in claim 15 wherein p is 0 and R2 is hydrogen.
17. A process as defined in claim 10 wherein, in the flame-retardant, R is phenyl.
18. A process as defined in claim 10 wherein the amount of flame-retardant is from 1 to 10 parts by weight per 100 parts by weight of polyphenylene ether resin, styrene resin, and flame-retardant combined.
19. A process for decreasing the self-extinguishing time of a normally flammable composition comprising a polyphenylene ether resin and a styrene resin, said process comprising adding to said composition from 2 to 4.5 parts by weight per 100 parts by weight of polyphenylene ether resin, styrene resin, and flame-retardant combined, of a flame-retardant of the formula wherein R is alkyl of from 1 to 18 carbon atoms, aryl or alkaryl.
20. A flame retardant composition comprising (a) a normally flammable composition comprising a polyphenylene ether resin and a styrene resin, and (b) from 2 to 4.5 parts by weight per 100 parts of (a) and (b) combined of a compound of the formula wherein R is alkyl of from 1 to 18 carbon atoms, aryl or alkaryl.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US830,833 | 1977-09-06 | ||
| US05/830,833 US4154775A (en) | 1977-09-06 | 1977-09-06 | Flame retardant composition of polyphenylene ether, styrene resin and cyclic phosphate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1109182A true CA1109182A (en) | 1981-09-15 |
Family
ID=25257779
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA310,441A Expired CA1109182A (en) | 1977-09-06 | 1978-08-31 | Flame retardant composition of poly-phenylene ether, styrene resin and cyclic phosphate |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US4154775A (en) |
| CA (1) | CA1109182A (en) |
Families Citing this family (131)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4198492A (en) * | 1977-09-27 | 1980-04-15 | Asahi-Dow Limited | Flame-retardant polyphenylene ether resin composition |
| DE3105946A1 (en) | 1981-02-18 | 1982-08-19 | Basf Ag, 6700 Ludwigshafen | SELF-EXTINGUISHING THERMOPLASTIC MOLDS |
| CA1185726A (en) * | 1981-05-15 | 1985-04-16 | Gim F. Lee, Jr. | Impact strength improved polyphenylene ether resin compositions |
| US4357433A (en) * | 1981-06-12 | 1982-11-02 | Fmc Corporation | Flame retardant polyphenylene ether resin compositions |
| US4446265A (en) * | 1982-02-01 | 1984-05-01 | Fmc Corporation | Flame retardant polyphenylene ether-styrene thermoplastic resin compositions |
| US4485262A (en) * | 1982-05-26 | 1984-11-27 | Fmc Corporation | s-Butyl bis(3-hydroxypropyl) phosphine oxide |
| US4503178A (en) * | 1984-04-26 | 1985-03-05 | Fmc Corporation | Cyclic phosphine oxides and their use as flame retardants in styrene modified polyphenylene ether resins |
| US4588764A (en) * | 1984-08-16 | 1986-05-13 | General Electric Company | Compositions of polyphenylene ether resin and diphosphites |
| US4711931A (en) * | 1985-02-28 | 1987-12-08 | Fmc Corporation | Flame retarded polycarbonate polymers |
| US4623687A (en) | 1985-03-01 | 1986-11-18 | Fmc Corporation | Bicyclic phosphine oxides and their use as flame retardants in styrene modified polyphenylene ether resins |
| US4613699A (en) * | 1985-03-01 | 1986-09-23 | Fmc Corporation | Phosphine oxides and their use as flame retardants in styrene modified polyphenylene ether resins |
| US4710530A (en) * | 1986-05-01 | 1987-12-01 | Fmc Corporation | Flame retardant polyphenylene ether molding compositions |
| DE19618741A1 (en) * | 1996-05-09 | 1997-11-13 | Basf Ag | Flame-retardant thermoplastic molding compounds with improved processing behavior |
| US6784234B2 (en) * | 1998-10-07 | 2004-08-31 | General Electric Company | High performance plastic pallets |
| US6258879B1 (en) | 1999-04-02 | 2001-07-10 | General Electric Company | Polyphenylene ether resin concentrates containing organic phosphates |
| JP2001214024A (en) * | 2000-02-04 | 2001-08-07 | Teijin Chem Ltd | Flame retardant styrene-based resin composition |
| WO2001074937A1 (en) * | 2000-03-30 | 2001-10-11 | General Electric Company | Transparent, flame retardant poly(arylene ether) blends |
| US20030124474A1 (en) * | 2000-06-07 | 2003-07-03 | David Elliott | Self extinguishing candles and method of making same |
| US20040209968A1 (en) * | 2001-05-07 | 2004-10-21 | Jos Bastiaens | Flame retardant expandable poly(arylene ether)/polystyrene compositions and preparation thereof |
| CN1266206C (en) * | 2001-09-27 | 2006-07-26 | Lg化学株式会社 | Styrenic thermoplastic resin composition |
| US7799855B2 (en) * | 2001-11-12 | 2010-09-21 | Sabic Innovative Plastics Ip B.V. | Flame retardant thermoplastic polycarbonate compositions, use and method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1155901B (en) * | 1959-11-17 | 1963-10-17 | Agfa Ag | Softeners for cellulose derivatives |
| GB1125620A (en) * | 1965-01-06 | 1968-08-28 | Gen Electric | Improvements in polymeric blends |
| US3639506A (en) * | 1969-05-21 | 1972-02-01 | Gen Electric | Flame retardant composition of polyphenylene ether styrene resin aromatic phosphate and aromatic halogen compound |
| US3883613A (en) * | 1972-12-04 | 1975-05-13 | Gen Electric | Flame retardant composition of polyphenylene ether, styrene resin and trimesityl phosphate and process for the preparation thereof |
-
1977
- 1977-09-06 US US05/830,833 patent/US4154775A/en not_active Expired - Lifetime
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1978
- 1978-08-31 CA CA310,441A patent/CA1109182A/en not_active Expired
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| US4154775A (en) | 1979-05-15 |
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