CA1096991A - Flame-retardant moulding compositions of thermoplastic material - Google Patents
Flame-retardant moulding compositions of thermoplastic materialInfo
- Publication number
- CA1096991A CA1096991A CA277,964A CA277964A CA1096991A CA 1096991 A CA1096991 A CA 1096991A CA 277964 A CA277964 A CA 277964A CA 1096991 A CA1096991 A CA 1096991A
- Authority
- CA
- Canada
- Prior art keywords
- phosphorus
- moulding compositions
- aluminum hydroxide
- particles
- red phosphorus
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/10—Encapsulated ingredients
-
- 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
- C08K9/00—Use of pretreated ingredients
- C08K9/02—Ingredients treated with inorganic substances
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)
- Fireproofing Substances (AREA)
Abstract
FLAME-RETARDANT MOULDING COMPOSITIONS OF
THERMOPLASTIC MATERIAL
ABSTRACT OF THE DISCLOSURE
Flame-retardant moulding compositions of thermo-plastic material homogeneously blended with about 1 to 10 weight % of red phosphorus particles with a size of at most about 100 microns are improved. To this end, the individual phosphorus particles are covered super-ficially with about 2 to 30 weight % of a protective aluminum hydroxide layer, based on the quantity of red phosphorus.
THERMOPLASTIC MATERIAL
ABSTRACT OF THE DISCLOSURE
Flame-retardant moulding compositions of thermo-plastic material homogeneously blended with about 1 to 10 weight % of red phosphorus particles with a size of at most about 100 microns are improved. To this end, the individual phosphorus particles are covered super-ficially with about 2 to 30 weight % of a protective aluminum hydroxide layer, based on the quantity of red phosphorus.
Description
99:~
Y`he present invention relates to flame-retardant moulding com-positions of thermoplastic material, the moulding compositions containing as a flame-retarding agent special grade pulverulent red phosphorus consist-ing of particles with a si~e of at most about 100 microns.
It has been described that thermoplastic material can be render-ed flame-retardant by incorporating a certain quantity of pulverulent red phosphorus therewith. German Patent Specification "Auslegeschrift"
1 769 712, for example, describes a process for making self-extinguishing thermoplastic moulding compositions, which are based on a copolymer of acrylonitrile/butadiene/styrene, wherein the aqueous copolymer latex of styrene and acrylonitrile is admixed with pulverulent red phosphorus, the resulting material is admixed, with agitation, with an aqueous graft polymer latex of butadiene/acrylonitrile/styrene, and the graft polymer is precipi-tated and separated in known manner.
A disadvantage encountered with the process just described resides in the fact that red phosphorus is liable to undergo a disproportionation reaction in a moist atmosphere with the resultant evolution of hydrogen phosphide, which is injurious to the health of the operating personnel.
A further process for making flame-retardant plastics material has been described in German Patent Specification "Offenlegungsschrift"
Y`he present invention relates to flame-retardant moulding com-positions of thermoplastic material, the moulding compositions containing as a flame-retarding agent special grade pulverulent red phosphorus consist-ing of particles with a si~e of at most about 100 microns.
It has been described that thermoplastic material can be render-ed flame-retardant by incorporating a certain quantity of pulverulent red phosphorus therewith. German Patent Specification "Auslegeschrift"
1 769 712, for example, describes a process for making self-extinguishing thermoplastic moulding compositions, which are based on a copolymer of acrylonitrile/butadiene/styrene, wherein the aqueous copolymer latex of styrene and acrylonitrile is admixed with pulverulent red phosphorus, the resulting material is admixed, with agitation, with an aqueous graft polymer latex of butadiene/acrylonitrile/styrene, and the graft polymer is precipi-tated and separated in known manner.
A disadvantage encountered with the process just described resides in the fact that red phosphorus is liable to undergo a disproportionation reaction in a moist atmosphere with the resultant evolution of hydrogen phosphide, which is injurious to the health of the operating personnel.
A further process for making flame-retardant plastics material has been described in German Patent Specification "Offenlegungsschrift"
2 408 488, wherein attempts are made to avoid the disadvantageous pheno-~ menon described above with the use of red phosphorus as a flame-retarding - agent by admixing~ prior to extrusion, the blend of pulverulent plastics material and red phosphorus with one or more addends which are selected from melamine, polyacrylonitrile, amidosulfonic acid, ammonium hydrogen sulfate, and similar materials.
In accordance with the present invention, we have unexpectedly found that thermoplastic materials which are processed on an extruder and stored in a moist atmosphere are substantially not liable to evolve hydrogen phosphide in all those cases in which they are used in admixture with ... .. ..
~l~91~99~L
pulverulent red phosphorus, whose particles are covered superficially with an aluminum hydroxide layer. In other words, aluminum hydroxide enables red phosphorus to be stabilized to an unexpected extent.
` The present invention provides more specifically flame-retardant moulding compositions of thermoplastic material homogeneously blended with about 1 to 10 weight % of red phosphorus particles with a size of at most ; about 1~0 microns, wherein the individual phosphorus particles are covered superficially with about 1 to 30 weight % of a protective aluminum hydro-xide layer, based on the quantity of red phosphorus.
. .
A preferred feature of the present invention provides for the phosphorus particles to be covered superficially with 1 to 15 weight % of aluminum hydroxide, based on the quantity of red phosphorus.
The term "thermoplastic materials" as used herein is intended to mean plastics material, such as a polyurethane, polyamide, polyformal-; dehyde, polyethylene terephthalate, polybutylene terephthalate, epoxy resin, styrene/acrylonitrile copolymer, polyvinyl chloride, or polyolefin.
The protective layer of aluminum hydroxide may preferably be - applied to the phosphorus particles by precipitating the aluminum hydroxide ; from an aqueous aluminum salt solution having pulverulent red phosphorus suspended therein. The red phosphorus so treated is dried and may then be incorporated into plastics material, for example by preparing a blend of pulverulent plastics material and red phosphorus and processing the blend on an extruder.
As will more clearly result from the following Examples, consider-ably less hydrogen phosphide is liable to be evolved by thermoplastic ma- ;
terial which has been treated with red phosphorus of which the individual particles are superficially coated with aluminum hydroxide. This is highly desirable and a result of the fact that the individual phosphorus particles are completely embedded in aluminum hydroxide. No such desirable effect is produced in all those cases in which a mechanically prepared blend of pulverulent red phosphorus and crystalline aluminum hydroxide is incor-porated with a thermoplastic material.
The following Examples illustrate the invention which is, how-ever, not limited thereto.
EXAMPLE 1 ~Invention) ~i Three phosphorus specimens A), B), and C) treated with Al(OH)3 ;~ were made as follows:
A) 100 g of fine pulverulent red phosphorus consisting of particles with a size of 10 to 100 microns was suspended in about 400 cc of water, the suspension was admixed with 200 cc of a 20 % sodium hydroxide solution, and the whole was heated for about 2 hours to 100C with agitation and while passing 10 l/h of nitrogen therethrough. Next, the phosphorus was filtered and water-washed until free from alkali.
The moist phosphorus filter cake was placed in a stirring vessel, suspended in 500 cc of water, the resulting suspension was admixed with 33 g of aluminum sulfate (A12~S04)3 . 18 H20) and heated to 60C. Next, a pH-value of 7 was established by means of a 5 % sodium hydroxide solution.
After a postreaction period of 1 hour, the phosphorus was filtered, water-washed and dried at 80C in a stream of nitrogen.
B) Specimen B) was prepared in the same manner as specimen A), but with the use of 65.5 g of aluminum sulfate (A12(S04)3 . 18 H20).
C) Specimen C) was prepared in the same manner as specimen A), but with the use of 196.5 g of aluminum sulfate (A12(SO4)3 . 18 H2O).
Preparation of polyethylene test sheets containing specimens A), B), and C), respectively.
450 g of low pressure polyethylene with a melt index (i5) of 10.8 and a density of 0.951 g/cc was extruded in each particular case with the use of 50 g of one of the specimens A), B) and C), and the extruded material was compressed in a steam-heated hydraulic press at 180C and under a pressure of 50 kg/cm into test sheets 2 mm thick. Next, the ~ '~. J~
'~
~L~3!969~
test sheets were sewn into test tapes of 100 cm2.
Testing tapes for quantity of hydrogen phosphide evolved.
Three tapes which contained phosphorus specimens A), B) and C), respectively, were stored for 6 days in separate glass vessels at 50C and 100 % of relative atmospheric moisture. The quantity of hydrogen phosphide evolved was passed together with 10 l/h of air through a small test tube ~a product of Drager company, Lubeck, type hydrogen phosphide 50/a) and identified by metering the colored indicating layer.
The results obtained are indicated in the Table hereinafter.
EXAMPLE 2 (Comparative Example) Preparation of four phosphorus specimens D) - G).
D) 100 g of fine pulverulent red phosphorus consisting of particles with a size of 10 to 100 microns was suspended in about 400 cc of water, the suspension was admixed with 200 cc of a 20 % sodium hydroxide solution, and the whole was heated for about 2 hours to 100C with agitation and while passing 10 l/h of nitrogen therethrough. Nextl the phosphorus was filtered and water-washed until free from alkali.
The moist phosphorus filter cake was placed in a stirring vessel, suspended in 500 cc of water, the resulting suspension was admixed with 10 g of fine particulate, crystalline aluminum hydroxide and heated to ~0C. After a postreaction period of 1 hour, the phosphorus was filtered, water-washed and dried at 80C in a stream of nitrogen.
E) 100 g of fine pulverulent red phosphorus was placed in a stirr-ing vessel, suspended in about 500 cc of water, the resulting suspension was admixed with 10 g of fine particulate, crystalline aluminum hydroxide and heated to 60 C.
F) 100 g of fine pulverulent red phosphorus was intimately blended with 10 g of fine particulate, crystalline aluminum hydroxide.
G) 100 g of fine pulverulent red phosphorus was intimately blended with 20 g of fine particulate, crystalline aluminum hydroxide.
X
;~
6~
The polyethylene test sheets containing specimens D) - G), re-spectively, were prepared, and the quantity of hydrogen phosphide evolved : by the test tapes D) - G) was determined, in the manner described in Example 1. ~he results obtained are indicated in the following Table.
~.
~0~69~9~
~ T A B 1, E
:
Test tape containing Quantity o~ hydrogen phosphide specimen e~ol~ed m surf2ce . day A ~.57 C 2.~
: D 8.24 E 10.49 ~ . ..., . __ F 20~22 G 19.46 _ The Table shows ~learly that the test tapes con-; tain~ng the phosphorus specimens A) - C) of the prese~t invention are ~ubstantially less liable in moist atmo-sphere to evolve h~drogen phosphid~ than the test tapes containin~ the ~omparative phosphorus specimens D~ - G).
b '.
- ,. . . ~
In accordance with the present invention, we have unexpectedly found that thermoplastic materials which are processed on an extruder and stored in a moist atmosphere are substantially not liable to evolve hydrogen phosphide in all those cases in which they are used in admixture with ... .. ..
~l~91~99~L
pulverulent red phosphorus, whose particles are covered superficially with an aluminum hydroxide layer. In other words, aluminum hydroxide enables red phosphorus to be stabilized to an unexpected extent.
` The present invention provides more specifically flame-retardant moulding compositions of thermoplastic material homogeneously blended with about 1 to 10 weight % of red phosphorus particles with a size of at most ; about 1~0 microns, wherein the individual phosphorus particles are covered superficially with about 1 to 30 weight % of a protective aluminum hydro-xide layer, based on the quantity of red phosphorus.
. .
A preferred feature of the present invention provides for the phosphorus particles to be covered superficially with 1 to 15 weight % of aluminum hydroxide, based on the quantity of red phosphorus.
The term "thermoplastic materials" as used herein is intended to mean plastics material, such as a polyurethane, polyamide, polyformal-; dehyde, polyethylene terephthalate, polybutylene terephthalate, epoxy resin, styrene/acrylonitrile copolymer, polyvinyl chloride, or polyolefin.
The protective layer of aluminum hydroxide may preferably be - applied to the phosphorus particles by precipitating the aluminum hydroxide ; from an aqueous aluminum salt solution having pulverulent red phosphorus suspended therein. The red phosphorus so treated is dried and may then be incorporated into plastics material, for example by preparing a blend of pulverulent plastics material and red phosphorus and processing the blend on an extruder.
As will more clearly result from the following Examples, consider-ably less hydrogen phosphide is liable to be evolved by thermoplastic ma- ;
terial which has been treated with red phosphorus of which the individual particles are superficially coated with aluminum hydroxide. This is highly desirable and a result of the fact that the individual phosphorus particles are completely embedded in aluminum hydroxide. No such desirable effect is produced in all those cases in which a mechanically prepared blend of pulverulent red phosphorus and crystalline aluminum hydroxide is incor-porated with a thermoplastic material.
The following Examples illustrate the invention which is, how-ever, not limited thereto.
EXAMPLE 1 ~Invention) ~i Three phosphorus specimens A), B), and C) treated with Al(OH)3 ;~ were made as follows:
A) 100 g of fine pulverulent red phosphorus consisting of particles with a size of 10 to 100 microns was suspended in about 400 cc of water, the suspension was admixed with 200 cc of a 20 % sodium hydroxide solution, and the whole was heated for about 2 hours to 100C with agitation and while passing 10 l/h of nitrogen therethrough. Next, the phosphorus was filtered and water-washed until free from alkali.
The moist phosphorus filter cake was placed in a stirring vessel, suspended in 500 cc of water, the resulting suspension was admixed with 33 g of aluminum sulfate (A12~S04)3 . 18 H20) and heated to 60C. Next, a pH-value of 7 was established by means of a 5 % sodium hydroxide solution.
After a postreaction period of 1 hour, the phosphorus was filtered, water-washed and dried at 80C in a stream of nitrogen.
B) Specimen B) was prepared in the same manner as specimen A), but with the use of 65.5 g of aluminum sulfate (A12(S04)3 . 18 H20).
C) Specimen C) was prepared in the same manner as specimen A), but with the use of 196.5 g of aluminum sulfate (A12(SO4)3 . 18 H2O).
Preparation of polyethylene test sheets containing specimens A), B), and C), respectively.
450 g of low pressure polyethylene with a melt index (i5) of 10.8 and a density of 0.951 g/cc was extruded in each particular case with the use of 50 g of one of the specimens A), B) and C), and the extruded material was compressed in a steam-heated hydraulic press at 180C and under a pressure of 50 kg/cm into test sheets 2 mm thick. Next, the ~ '~. J~
'~
~L~3!969~
test sheets were sewn into test tapes of 100 cm2.
Testing tapes for quantity of hydrogen phosphide evolved.
Three tapes which contained phosphorus specimens A), B) and C), respectively, were stored for 6 days in separate glass vessels at 50C and 100 % of relative atmospheric moisture. The quantity of hydrogen phosphide evolved was passed together with 10 l/h of air through a small test tube ~a product of Drager company, Lubeck, type hydrogen phosphide 50/a) and identified by metering the colored indicating layer.
The results obtained are indicated in the Table hereinafter.
EXAMPLE 2 (Comparative Example) Preparation of four phosphorus specimens D) - G).
D) 100 g of fine pulverulent red phosphorus consisting of particles with a size of 10 to 100 microns was suspended in about 400 cc of water, the suspension was admixed with 200 cc of a 20 % sodium hydroxide solution, and the whole was heated for about 2 hours to 100C with agitation and while passing 10 l/h of nitrogen therethrough. Nextl the phosphorus was filtered and water-washed until free from alkali.
The moist phosphorus filter cake was placed in a stirring vessel, suspended in 500 cc of water, the resulting suspension was admixed with 10 g of fine particulate, crystalline aluminum hydroxide and heated to ~0C. After a postreaction period of 1 hour, the phosphorus was filtered, water-washed and dried at 80C in a stream of nitrogen.
E) 100 g of fine pulverulent red phosphorus was placed in a stirr-ing vessel, suspended in about 500 cc of water, the resulting suspension was admixed with 10 g of fine particulate, crystalline aluminum hydroxide and heated to 60 C.
F) 100 g of fine pulverulent red phosphorus was intimately blended with 10 g of fine particulate, crystalline aluminum hydroxide.
G) 100 g of fine pulverulent red phosphorus was intimately blended with 20 g of fine particulate, crystalline aluminum hydroxide.
X
;~
6~
The polyethylene test sheets containing specimens D) - G), re-spectively, were prepared, and the quantity of hydrogen phosphide evolved : by the test tapes D) - G) was determined, in the manner described in Example 1. ~he results obtained are indicated in the following Table.
~.
~0~69~9~
~ T A B 1, E
:
Test tape containing Quantity o~ hydrogen phosphide specimen e~ol~ed m surf2ce . day A ~.57 C 2.~
: D 8.24 E 10.49 ~ . ..., . __ F 20~22 G 19.46 _ The Table shows ~learly that the test tapes con-; tain~ng the phosphorus specimens A) - C) of the prese~t invention are ~ubstantially less liable in moist atmo-sphere to evolve h~drogen phosphid~ than the test tapes containin~ the ~omparative phosphorus specimens D~ - G).
b '.
- ,. . . ~
Claims (4)
- THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
l. Improved flame-retardant moulding compositions of thermoplastic material homogeneously blended with about 1 to 10 weight % of red phospho-rus particles with a size of at most about 100 microns, wherein the individual phosphorus particles are covered superficially with about 1 to 30 weight % of a protective aluminum hydroxide layer, based on the quan-tity of red phosphorus. - 2. Moulding compositions as claimed in claim 1, wherein the phosphorus particles are covered superficially with 1 to 15 weight % of aluminum hydroxide, based on the quantity of red phosphorus.
- 3. Moulding compositions as claimed in claim 1, wherein the thermo-plastic material is a polyurethane, polyamide, polyformaldehyde, poly-ethylene terephthalate, polybutylene terephthalate, styrene/acrylonitrile copolymer, polyvinyl chloride or polyolefin.
- 4. Moulding compositions as claimed in claim l, wherein the aluminum hydroxide is a precipitate on the surface of the individual phosphorus particles.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2623112.9 | 1976-05-22 | ||
| DE2623112A DE2623112C2 (en) | 1976-05-22 | 1976-05-22 | Flame-retardant molding compounds made from thermoplastics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1096991A true CA1096991A (en) | 1981-03-03 |
Family
ID=5978804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA277,964A Expired CA1096991A (en) | 1976-05-22 | 1977-05-09 | Flame-retardant moulding compositions of thermoplastic material |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS52142751A (en) |
| AT (1) | AT351270B (en) |
| BE (1) | BE854858A (en) |
| CA (1) | CA1096991A (en) |
| CH (1) | CH626107A5 (en) |
| DE (1) | DE2623112C2 (en) |
| FR (1) | FR2352024A1 (en) |
| GB (1) | GB1536525A (en) |
| NL (1) | NL7705594A (en) |
| SE (1) | SE418861B (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2314221A1 (en) * | 1975-06-10 | 1977-01-07 | Rhone Poulenc Ind | COMPOSITIONS INTENDED FOR THE FLAME PROTECTION OF PLASTICS |
| FR2344615A1 (en) * | 1976-03-19 | 1977-10-14 | Rhone Poulenc Ind | COMPOSITIONS INTENDED FOR THE FLAME PROTECTION OF PLASTICS |
| DE2811951A1 (en) * | 1978-03-18 | 1979-09-27 | Hoechst Ag | FLAME RETARDANT POLYSTRICAL FOAM AND METHOD FOR MANUFACTURING IT |
| JPS5998123A (en) * | 1982-11-26 | 1984-06-06 | Sanyurejin Kk | Flame-retardant epoxy resin composition |
| JPS59170176A (en) * | 1983-03-17 | 1984-09-26 | Nippon Chem Ind Co Ltd:The | Red phosphorus based flame retardant composition |
| JPS61130370A (en) * | 1984-11-29 | 1986-06-18 | Nippon Chem Ind Co Ltd:The | Flame-retardant resin composition |
| IT1200424B (en) * | 1985-03-19 | 1989-01-18 | Saffa Spa | RED PHOSPHORUS STABILIZED FOR USE AS A FLAME RETARDANT, ESPECIALLY FOR POLYMER-BASED COMPOSITIONS |
| JPS63110254A (en) * | 1986-10-27 | 1988-05-14 | Rin Kagaku Kogyo Kk | Flame-retardant resin composition |
| GB8703160D0 (en) * | 1987-02-11 | 1987-03-18 | Bip Chemicals Ltd | Polyamide compositions |
| JPS644632A (en) * | 1987-06-26 | 1989-01-09 | Phosphorus Chem Ind | Fire-retardant resin composition |
| CN101142271B (en) | 2005-02-18 | 2012-02-22 | 泰科电子有限公司 | Heat-recoverable article and composition therefor |
| EP4174124A1 (en) * | 2021-10-29 | 2023-05-03 | SHPP Global Technologies B.V. | Encapsulation of flame retardant agents by atomic layer deposition for improved flame retardant formulations |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1965635B2 (en) * | 1969-12-31 | 1971-06-16 | Badische Anilin & Soda Fabrik AG, 6700 Ludwigshafen | PRODUCTION OF THERMOPLASTIC PLASTICS WITH RED PHOSPHORUS FLAME RETARDANT |
| US3847861A (en) * | 1971-09-14 | 1974-11-12 | Allied Chem | Polyethylene terephthalate |
| DE2308104A1 (en) * | 1973-02-19 | 1974-08-22 | Hoechst Ag | MOLDING COMPOUNDS MADE FROM THERMOPLASTIC PLASTICS |
| DE2408488A1 (en) * | 1974-02-22 | 1975-08-28 | Hoechst Ag | GRANULATES MADE FROM RED PHOSPHORUS AND A BINDING AGENT FOR FLAME RETARDANT FINISHING OF PLASTICS |
| FR2314216A1 (en) * | 1975-06-10 | 1977-01-07 | Rhone Poulenc Ind | FIRE-PROOF COMPOSITIONS OF PLASTICS |
-
1976
- 1976-05-22 DE DE2623112A patent/DE2623112C2/en not_active Expired
-
1977
- 1977-05-03 CH CH553877A patent/CH626107A5/en not_active IP Right Cessation
- 1977-05-03 GB GB18443/77A patent/GB1536525A/en not_active Expired
- 1977-05-09 CA CA277,964A patent/CA1096991A/en not_active Expired
- 1977-05-17 SE SE7705804A patent/SE418861B/en unknown
- 1977-05-20 AT AT363577A patent/AT351270B/en not_active IP Right Cessation
- 1977-05-20 BE BE177758A patent/BE854858A/en not_active IP Right Cessation
- 1977-05-20 FR FR7715547A patent/FR2352024A1/en active Granted
- 1977-05-20 NL NL7705594A patent/NL7705594A/en not_active Application Discontinuation
- 1977-05-23 JP JP5972977A patent/JPS52142751A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ATA363577A (en) | 1978-12-15 |
| BE854858A (en) | 1977-11-21 |
| CH626107A5 (en) | 1981-10-30 |
| JPS52142751A (en) | 1977-11-28 |
| AT351270B (en) | 1979-07-10 |
| SE418861B (en) | 1981-06-29 |
| DE2623112C2 (en) | 1984-08-23 |
| SE7705804L (en) | 1977-11-23 |
| DE2623112A1 (en) | 1977-12-01 |
| FR2352024B1 (en) | 1984-03-02 |
| FR2352024A1 (en) | 1977-12-16 |
| NL7705594A (en) | 1977-11-24 |
| GB1536525A (en) | 1978-12-20 |
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| MKEX | Expiry |