GB2325933A - Flame retardant bis-[2,4-bis(dimethylethyl)phenyl-2,6-dimethylphenyl] aryl diphosphate compounds, method for their production & resin compositions of the same - Google Patents

Flame retardant bis-[2,4-bis(dimethylethyl)phenyl-2,6-dimethylphenyl] aryl diphosphate compounds, method for their production & resin compositions of the same Download PDF

Info

Publication number
GB2325933A
GB2325933A GB9711361A GB9711361A GB2325933A GB 2325933 A GB2325933 A GB 2325933A GB 9711361 A GB9711361 A GB 9711361A GB 9711361 A GB9711361 A GB 9711361A GB 2325933 A GB2325933 A GB 2325933A
Authority
GB
United Kingdom
Prior art keywords
bis
compound
phenyl
dimethylethyl
formula
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.)
Withdrawn
Application number
GB9711361A
Other versions
GB9711361D0 (en
Inventor
Hae Ryong Chung
Min Kyo Cheong
Chang Hyun Kwon
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hanwha General Chemicals Co Ltd
Original Assignee
Samsung General Chemicals Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Samsung General Chemicals Co Ltd filed Critical Samsung General Chemicals Co Ltd
Priority to GB9711361A priority Critical patent/GB2325933A/en
Priority to FR9706812A priority patent/FR2763952A1/en
Priority to DE19723221A priority patent/DE19723221A1/en
Publication of GB9711361D0 publication Critical patent/GB9711361D0/en
Publication of GB2325933A publication Critical patent/GB2325933A/en
Withdrawn legal-status Critical Current

Links

Classifications

    • 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 Table
    • 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
    • C07F9/12—Esters of phosphoric acids with hydroxyaryl 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
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
    • C08K5/523—Esters of phosphoric acids, e.g. of H3PO4 with hydroxyaryl compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Bis [2,4-bis(1,1-dimethylethyl)phenyl-2,6-dimethylphenyl] aryl diphosphate compounds having the following formula 1 are flame retardants imparting heat resistance as well as flame retardance to plastic resins.

Description

BIS\2,SBlS(1,1-DIMETHYLETHYL)PHENYL-2,6- DIMETffYLPIlENYLi ARYL DIPHOSPHATE COMPOUND, A METHOD FOR PRODUCING THE SAME AND RESIN COMPOSITIONS CONTAINING THE SAME This invention relates to a flame retardant, a method for producing them and resin compositions containing them, in particular, to bis [2,4 bis(1,1-dimethylethyl)phenyl-2,6-dimethylphenyl] aryl diphosphate compound having the following formula 1, a novel organic compound for the use of imparting flame retardant and heat resistant plastic resins, a method for producing them and resin compositions containing them as a flame retardant Formula I
Recently, it is generally needed to reduce the inflammability of plastics, rubber, papers, and the like. In particular, various polymers having many excellent properties are widely used in the field of electric and clcctronic appliances, automobiles, airplanes and ships, so that the polymers are necessary to havc flame retardance currently.
In general, organophosphorous compounds are known as good name relarttanLs but have defects of relatively high volatility and low hcat resistance. Particularly, new high-perfonnance plastics such as engineering plastics and super-engineering plastics are processed around 300"C or above and hence flame retardants are required to have high heat resistance.
Aromatic organophosphate compounds were disclosed in USP No. 4,134,876 as flame retardants having high heat resistance and low volatility. But the compounds have colors and a resin including the compound is not suitable for a base material of a final product due to the compounds' colors.
A compound having the following formula 7 was disclosed in USP No. 5,122,558 and EP publication No. 509,506 and a compound having the following formula 8 was disclosed in JP publication No. 96208972. Polymeric resins have a tendency to be degraded by heat depending on the use of final products and in spite of their good flame retardance, the compounds are unsuitable to household electric appliances generating much heat due to their unsatisfactory heat resistance.
Formula 7
Formula 8
In the above formula 8, x is arylene group and RI, R2, R3 and RJ are substituted or unsubstituted alkyl group.
A method for producing aromatic diphosphate oligomer phosphate compound that uses phosphorous oxychloride and dihydroxylic phenol (formula 4) compound or monohydroxylic phenol compound(fonnula 9) as reactants was disclosed in USP No. 2,520,090 and EP EJo. 613,902. But the method described in the USP No. 2,520,09O has problems that residual phosphorous oxychloride must be removed after reaction and by-products such as various oligomers are generated. And the method described in EP No. 613,902 has a problem that reaction intermediates must be purified after reaction between oxychloride and monohydroxylic phenol compound in order to supress fonnation ofthe oligomers, by-products.
Formula 4
Examples of the formula 4 are resorcinol and hydroquinone.
Formula 9
In the above formula 9, R1 is hydrogen atom or alkyl group with carbon number from 1 to 8 and R2 are alkyl group with carbon number from 1 to 8.
A method for producing powders of aromatic diphosphate compounds was disclosed in IJSP No. 5,420,327 and JP No. 2,552,780.
The aromatic diphosphate compounds have a purity of 90% or above by the method reacting phosphorous oxychloride and monohydroxylic phenol compound followed by reacting dihydroxylic phenol compound. It was described that the compounds wcrc superior to the prior non-halogen phosphate flame retardants, such as triphenyl phosphate(TPP) and resorcinol diphospliate(RDP) in flame retardance and heat resistance.
But the compounds have unsatisfactory heat resistance for the use of household electric appliances generating much heat.
In order to solve the problems as described above, an object of this invention is to provide an aromatic diphosphatc compound, flame retardant showing excellent heat resistance by introducing tertiary butyl group.
This invention provides a method for producing the intermediate compound with 90% or above purily that makes it unnecessary to remove phosphorous oxychloride during reaction and reduces the formation of oligomers, by-product by imparting steric hindrance to monohydroxylic phenol compounds. This invention also provides resin compositions containing the compound as a flame retardant One aspect of this invention provides bis t2,4-bis(l,l- dimetylethyl)phenyl-2,6-dimethylphenyl] aryl diphosphate compound having the following formula 1.
Formula 1
The bis [2,4-bis(1,1-dimetylethyl)phenyl-2,6-dimethylphenyl] aryl diphosphate compound is preferably bis [2,4-bis(1,1-dimetylethyl)phenyl- 2,6-dimethylphenyl] resorcinol diphosphate compound having the following formula 2 or bis I2,4-bis(1,1 -dimetylethyl)phenyl-2,6- dimethylphenyl] hydroquinone diphosphate compound having the following formula 3.
Formula 2
Formula 3
And this invention also provides the use of the [2,4-bis(l,l- dimetylethyl)phenyl-2,6-dimethylphenyl] aryl diphosphate compounds as flame retardants.
Another aspect of this invention provides a method for producing bis [2,4-bis(1,1 -dimetylethyl)phenyl-2 ,6-dimethylphcnyl] aryl diphosphate compound comprising the stcps of (a)forming a dichlorophosphate intermediate by reacting phosphorous oxychloride with a compound having the formula 5 in the presence of a catalyst, (b)forming a chlorophosphale inti:rrriediate by reacting the dichlorophosphate intermediate with a compound having the formula 6 in the presence of the catalyst, and (c)fonning the bis [2,4-bis(l -dimetylethyl)-2,6- dimethylphenyl] aryl diphosphate compound by reacting the chlorophosphate intermediate with a compound having the formula 4.
Formula 4
Formula 5
Formula 6
The compound having the formula 4 is preferably a resorcinol compound or a hydroquinone compound. A reaction in the method is shown by the following reaction formula 1.
Reaction formula 1
The Lewis acid catalyst is preferably MgC12 or Air13. This invention imparts heat resistance to the flame retardant by introducing the compound having tertiary butyl group.
In the step of fonning the dichlorophosphate intermediate by reacting phosphorous oxychloride with the compound having the formula S in the presence of the catalyst, the dichlorophosphate intermediate having high purity can be obtained by substituting tertiary butyl group giving stearic hindrance, at the adjacent position to hydroxyl group of the monohydroxylic phenol compound, i. e. at 2(or 6) position of the monohydroxylic phenol compound. In case the monohydroxylic phenol compound has been substituted by tertiary butyl group at 2(or 6) position, it can be more substituted at 3, 4, 5 or 6(or 2) position. But the substitution of tertiary butyl group at 2(or 6) position causes the hydroxyl group of the monohydroxylic phenol compound to have low reactivity, so that it is the most preferable to substitute another tertiary butyl group at 4 position considering the reactivity and a production cost.
The third aspect of this invention provides resin compositions comprising a polymeric resin and a bis [2,4-bis(l,l-dimetylethyl)-2,6- dimethylphenyl] aryl diphosphate compound having the above formula 1 of 0.1-50% by weight of the weight of the polymeric resin. In the resin compositions, thc bis [2,4-bis(l,l -dimetylethyl)-2,6-dimethylphenyl] aryl diphosphate compound is prcfcrably a bis [2,4-bis(l,l-dimetylethyl)-2,6- dimethylphenyl] resorcinol diphosphate compound or a bis [2,4-bis(l,l- dimetylethyl)*2,6-dimetbylphenyl] hydroquinone diphosphate compound.
The polymeric resin is preferably selected from the group consisting of polyvinyl chloride, polyethylene, polypropylene, ABS resin, polystyrene, polymethylmetacrylate, polyamide, polycarbonate, polyurethane, phenol resin, melamine resin, unsaturated polyester and the mixtures thereof.
The most preferably, the polymeric resin comprises 90-10% by weight polycarbonate and 10-90% by weight ABS. The content of the aromatic organic compound having the formula 1 is controlled suitably depending on the use of a resin, and the ordinary content of the compound is 0.1 to 50% by weight of the weight of the resin. The flame retardant can be added to the polymeric resin by ordinary mixing method. If necessary, various additives such as antioxidants and packing agents can be added.
Figure 1 is an Infrared absorption spectrum of [2,4-bis(1,1- dimethyIethyl)phcnyl-2,6-dimethylphenyl] resorcinol diphosphate compound obtained in the Example 1 of this invention.
Figure 2 is an Infrared absorption spectrum of [2,4-bis(1,1- dimethylethyl)phenyl-2,6-dimethylphenyl] hydroquinone diphosphate compound obtained in the Example 2 of this invention.
This invention is further explained in more detail with reference to the following examples which do not limit this invention.
EXAMPLE 1 production of bis [2,4-bis(1,1-dimethylethyl)phenyl-2,6-dimethylphenyl] resorcinol diphosphate compound 268.2g 2,4-bis(l,l -dimethylethyl) phenol, 2.0g magnesium chloride and 1 00g xylene were added in a dried flask equipped with a thermometer, a cooling condenser, and an agitator and then heated.
When the temperature of the reactants rcachcd 1 500C, 1 99.3g phosphorous oxychloride was added through one hour. Hydrogen chloride was captured with water. The reaction was continued in 135"C after the addition of the phosphorous oxychloride. When the generation of HCl gas stopped, the temperature was raised up to 180 OC. Through maturation for 4 hours, 12,4-bis(l, I-dimcthylethyl) phenyl] dichlorophosphate intermediate was obtained. The [2,4-bis(1,l- dimethylethyl) phenyl] dichlorophosphate intermediate was cooled down to 700C. 158.9g xylenol and 2.0g magnesium chloride were added and then the temperature was slowly raised up to 1500C. When the generation of HC1 gas stopped, the temperature was raised up to 180 OC.
through maturation for 4 hours, [2,4-bis(l,l-dimethylethyl) phenyl-2,6dimethylphenyl] chlorophosphate intermediate was obtained. The [2, bis( 1,1 -dimethylethyl) phenyl-2,6-dimethylphenyl] ch lorophosphate intermediate was cooled down to 70 C. 71.6g resorcinol and 3.0g magnesium chloride were added and then the themperature was raised up to 150 C. When the generation of HCl gas stopped, the temperature was raised up to 180 C, the reaction was matured for 4 hours. After the reaction has finishcd, a product was washed with 400g of 5% hydrochloride solution in order to remove the catalyst and impurities, and subsequently was washed with water. The product was dried under a decompressed condition and 534g of a final product of which melting point is 450C was obtained.
The structure of a compound, a final product, was identified with Infrared absorption(IR) spectrum and nuclear magnetic resonance(NMR) spectrum. IR spectrum was carried in a mixed plate form with potassium bromide by using Fouricr transform iriJiared(FT-IR) BRUKER IFS 66.
As shown in the Figure 1, the compound showed C-c stretching absorption bands at 1496cm and 1084cm-1, those of phenyl group, C-H3 deformation absorption bands at 1363cm-1 and 1399cm-1, those of CH3 in tertiary butyl group, a P=O stretching absorption band at 1308cm-1, and a P-O-Ar stretching absorption band at 1130cm-1. H NMR spectrum was camed with a solvent, CHCl3 and with the internal standard of 7.24 CDC13, using BRUKER DRX 400. As a result, 6's were 1.28(18H, s), 1.34(18H, s), 7.01(9H, m), 7.15(3H, m), 7.36(2H, dd), and 7.43(2H, d). Therefore the compound was identified to have the structure as shown in the formula 2.
Production of a resin comEosition 10% by weight bis[2,4-bis(1,1-dimethylethyl)phenyl-2,6- dimethylphenyl] resorcinol diphosphate was added to a 100% by weight resin comprising 90% by weight polycarbonate and 10% by weight ABS and mixed by a mixing machine. The mixture was extruded with twin screw extruder and the extruded material was cooled and cut to be obtained in a pellet form. a test piece was made by injection molding. Flame rctartance, discoloration, heat deformation temperature, Izod impact strength, and pulling strength were measured on the test piece and results of the measurement were shown in table 1.
EXAMPLE 2 production of bis[2,4-bis(1,1-dimethylethyl)phenyl-2,6-dimethylphenyl] hydroquinone diphosphate compound In the example I, the substantially same process was carried out except that resorcinol was replaced by hydroquinone. 530g of Bis [2,4bis(l,1-dimethylethyl)phenyl-2,6-dimethylphenyl] hydroquinone diphosphate having 49 C melting point was obtained. As a result of IR spectrum, the compound showed C=C stretching absorption bands at 1496cm and 1085cm~, those of phenyl group, CH3 deformation absorption band at 1363cm-1 and 1399cm-1, those of CH3 in tertiary butyl, P=O stretching absorption band at 1307cm-1, and P-Ar stretching absorption band at 1158cm-1 as shown in the Figure 2. As a result of lH NMR spectrum, 6's were I .29(18H, s), 1.34(18H, s), 7.01(9H, m), 7.14(3H, m), 7.37(2H, dd), and 7.44(2H, d). Therefore the compound was identified to have the structure as shown in the formula 3.
Production of a resin composition In the example 1, the substantially same process was carried out except that [2,4-bis(1,1-dimethylethyl)phenyl-2,6-dimethylphenyl] rcsorcinol diphosphate was replaced by [2,4-bis(1,1-dimethylethyl)phenyl- 2,6-dimethylphenyl] hydroquinone diphosphate. The result was shown in table 1.
COMPARATIVE EXAMPLE 1 In the production of the resin composition of example 1, the substantially same process was carried out except that bis[2,4-bis(l ,l - dimethylethyl)phenyl-2,6-dimethylphenyl 1 resorcinol diphosphate was rep laced by triphenyl phosphate(Junsei GR-grade reagent). The result was shown in table 1.
COMPARATIVE E?CAMPLt 2 In the production of the resin composition of example 2, the substantially same process was carried out except that bis[2,4-bis(l,1- dimethylethyl)phenyl-2,6-dimethylphenyl] hydroquinone diphosphate was replaced by tetrakis(2,6-dimethylphenyl) resorcinol diphosphate. The result was shown in table 1.
Test methods 1. flame retardanee flame retardance of the test pieces was evaluated by "inflammability test of plastic materials for machinery parts" in a test method of UL(Underwrites Laboratories Incoporaiion > 94. The test piece was 1 .6mm in thickness.
2. discoloration discoloration of the test pieces was evaluated by visual test.
3. Vicat softening temperature Vicar softening temperature of the test pieces was measured under a load of 1 kgf in compliance with ASTM D-1525.
4. Izod impact strength Izod impact strength was measured in compliance with ASTM D-256.
5. pulling strength pulling strength was measured in compliance with ASTM D-638.
Table 1
example 1 example 2 comparative comparative example 1 example 2 flamc rciardance Vo V0 V1 ~ VE
discoloration not not discolored a little discolored discolored discolored Vicatsoftening 128 131 106 118 temperature( C) Izodimpact 61 60 50 51 strength (lcg-cmicm) pulling strength 610 620 550 590 (kg/cm2) As shown in the table 1, the resin compositions using bis [2,4bis(1,1-dimetylethyl)phenyl-2,6-dimethylphenyl] resorcinol diphosphate compound or bis [2,4-bis(1,1-dimetylethyl)phenyl-2,6-dimethylphenyl] hydroquinone diphosphate compound produced by the method described in this invention as flame retardant arc less discolored and have higher Vicat softening temperature, impact strength and pulling strength than the resin composition using tripheyl phosphate or tetrakis[2,6-dimethylphenyl] resorcinol diphosphate.
Therefore, the aromatic diphosphate compounds described in this invention have excellent heat resistance as well as flame retardance enough to be used for flame retardants of plastic resins.

Claims (16)

1. A bis [2,4-bis(1,1-dimethylethyl) phenyl-216Aimethylphenyl) aryl diphosphate compound having the following formula 1: Formula 1
2. The compound according to claim 1, wherein said bis [2,4bis( 1,1-dimethylethyl)phenyl-2,6-dimethylphenyl] aryl diphosphate compound is a bis [2,4-bis(1,1-dimethylethyl)phenyI-2,6-dimethylphenyl resorcinol diphosphate compound having the following formula 2: Formula 2
3. Thc compound according to claim 1, wherein said bis [2,4 bis(1,1-dimethylethyl)phenyl-2,6-dimethylphenyl] aryl diphosphate compound is a bis [2,4-bis(1,1 -dimethylethyl)pheny1-2, 6-dimethylphenyl] hydroquinone diphosphate compound having the following formula 3: Formula 3
4. The use of the bis [2,4-bis(1, dimetylethyl)phenyl-2,6- dimethylphenyl] aryl diphosphate compound according to any one of claim 1 to 3 as a flame retardant.
5 A method for producing a bis [2,4-bis(1,1-dimethylethyl)phenyl-2,6- dimethylphenyll aryl diphosphate compound comprising the steps of: (a) forming a dichlorophospbate intermediate by reacting phosphorous oxychloride with a compound having the formula 5 in the prcscnce of a catalyst; (b)forming a chlorophosphate intermediate by reacting said dichlorophosphate intermediate with a compound having the formula 6 in the presence of a catalyst; and (c)forming the bis [2,4-bis (1, -dimethylethyl)phenyl-2,6-dimethylphenyiJ aryl diphosphate compound by reacting said chlorophosphate intermediate with a compound having the formula 4.
Formula 4
Formula 5
Formula 6
6. The method according to claim 4, wherein said compound having the formula 4 is a resorcinol compound.
7. The method according to claim 4, wherein said compound having the formula 4 is a hydroquinone compound.
8. A resin composition comprising: a polymeric resin of 100 parts by weight;and a bis [2,4-bis (1, 1-dimethylethyl)phenyl-2,6-dimethylphenyl] aryl diphosphate compound having thc above formula 1 of 0.1-50 parts by weight of the weight of the polymeric resin.
9. The resin composition according to claim 8, wherein the bis [2,4-bis(1,1-dimethylethyl)phenyl-2,6-dimethylphenyl] aryl diphosphate compound is a bis (2,4-bis(1,1-dimethyiethy1)pheny12,6-dimethyIphenyl] resorcinol diphosphate compound.
10. The resin composition according to claim 8, wherein the bis [2,4-bis (1,1 -dimethylethyl)phenyl- 2, 6-dimethyiphenyl] aryl diphosphate compound is a bis (2,4-bis (1,1 -dimethylethyl)phenyl-2,6-dimethyiphenyl] hydroquinone diphosphate compound.
11. The resin composition according to claim 8, wherein said polymeric resin is selected from the group consisting of polyvinyl chloride, polyethylene, polypropylene, ABS resin, polystyrene, polyamide, polymethyl metacrylate, polycarbonate, polyurethane, phenol resin, melamine resin, unsaturated polyester and the mixtures thereof.
12. The resin composition according to claim 8, wherein said polymeric resin comprises 90-10% by weight polycarbonate and 10-90% by weight ABS resin.
13. A flame retardant comprising a bis [2,4-bis (1, 1-dimethylethyl) phenyl-2,6dimethylphenyl] aryl diphosphate compound as claimed in any one of the claims 1 to 3.
14. A compound substantially as herein described with reference to formulae 1, 2 or 3 of the accompanying description.
15. A method for producing a compound substantially as hereinbefore described.
16. A resin composition substantially as hereinbefore described.
GB9711361A 1997-06-02 1997-06-02 Flame retardant bis-[2,4-bis(dimethylethyl)phenyl-2,6-dimethylphenyl] aryl diphosphate compounds, method for their production & resin compositions of the same Withdrawn GB2325933A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
GB9711361A GB2325933A (en) 1997-06-02 1997-06-02 Flame retardant bis-[2,4-bis(dimethylethyl)phenyl-2,6-dimethylphenyl] aryl diphosphate compounds, method for their production & resin compositions of the same
FR9706812A FR2763952A1 (en) 1997-06-02 1997-06-03 New bis-2,4-bis-1,1-di:methyl-ethyl-phenyl-2,6-di:methylphenyl aryl di:phosphate(s)
DE19723221A DE19723221A1 (en) 1997-06-02 1997-06-03 BisÝ2,4-bis(1,1-dimethylethyl)phenyl-2,6-dimethylphenyl¨ aryl diphosphate compound

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB9711361A GB2325933A (en) 1997-06-02 1997-06-02 Flame retardant bis-[2,4-bis(dimethylethyl)phenyl-2,6-dimethylphenyl] aryl diphosphate compounds, method for their production & resin compositions of the same
FR9706812A FR2763952A1 (en) 1997-06-02 1997-06-03 New bis-2,4-bis-1,1-di:methyl-ethyl-phenyl-2,6-di:methylphenyl aryl di:phosphate(s)
DE19723221A DE19723221A1 (en) 1997-06-02 1997-06-03 BisÝ2,4-bis(1,1-dimethylethyl)phenyl-2,6-dimethylphenyl¨ aryl diphosphate compound

Publications (2)

Publication Number Publication Date
GB9711361D0 GB9711361D0 (en) 1997-07-30
GB2325933A true GB2325933A (en) 1998-12-09

Family

ID=27217438

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9711361A Withdrawn GB2325933A (en) 1997-06-02 1997-06-02 Flame retardant bis-[2,4-bis(dimethylethyl)phenyl-2,6-dimethylphenyl] aryl diphosphate compounds, method for their production & resin compositions of the same

Country Status (3)

Country Link
DE (1) DE19723221A1 (en)
FR (1) FR2763952A1 (en)
GB (1) GB2325933A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2468814A1 (en) 2010-12-22 2012-06-27 Cheil Industries Inc. Novel Phosphorus Compound, Method of Preparing the Same and Flame Retardant Thermoplastic Resin Composition Including the Same
WO2016197915A1 (en) * 2015-06-08 2016-12-15 金发科技股份有限公司 Polycarbonate composition and preparation method therefor

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008027536A1 (en) * 2006-08-31 2008-03-06 Supresta Llc Oligomeric bis-phosphate flame retardants and compositions containing the same
WO2010104689A1 (en) * 2009-03-09 2010-09-16 Icl-Ip America Inc. Flame retarded polyolefin composition

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5420327A (en) * 1992-09-14 1995-05-30 Akzo Nobel N.V. Process for forming hydrocarbyl bisphosphate compound

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2901304B2 (en) * 1990-02-13 1999-06-07 大八化学工業株式会社 PVC resin film
JP2552780B2 (en) * 1991-04-16 1996-11-13 大八化学工業株式会社 Method and application for producing aromatic diphosphate
TW280824B (en) * 1993-09-09 1996-07-11 Ciba Geigy Ag
JPH08208972A (en) * 1994-11-10 1996-08-13 Toray Ind Inc Thermoplastic resin composition

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5420327A (en) * 1992-09-14 1995-05-30 Akzo Nobel N.V. Process for forming hydrocarbyl bisphosphate compound

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2468814A1 (en) 2010-12-22 2012-06-27 Cheil Industries Inc. Novel Phosphorus Compound, Method of Preparing the Same and Flame Retardant Thermoplastic Resin Composition Including the Same
US8410203B2 (en) 2010-12-22 2013-04-02 Cheil Industries Inc. Phosphorus compound, method of preparing the same and flame retardant thermoplastic resin composition including the same
WO2016197915A1 (en) * 2015-06-08 2016-12-15 金发科技股份有限公司 Polycarbonate composition and preparation method therefor

Also Published As

Publication number Publication date
GB9711361D0 (en) 1997-07-30
DE19723221A1 (en) 1998-12-10
FR2763952A1 (en) 1998-12-04

Similar Documents

Publication Publication Date Title
JP2552780B2 (en) Method and application for producing aromatic diphosphate
US6528559B1 (en) Crosslinked phenoxyphosphazene compounds, process for the preparation thereof, flame retardants, flame-retardant resin compositions, and moldings of flame-retardant resins
US6596893B2 (en) Crosslinked phenoxyphosphazene compounds, flame retardants, flame-retardant resin compositions, and moldings of flame-retardant resins
DE69918721T2 (en) POWDERY FLAMMABLE HEMMER
EP1797055A2 (en) Phosphate ester flame retradants from resorcinol-ketone reaction products
GB2325933A (en) Flame retardant bis-[2,4-bis(dimethylethyl)phenyl-2,6-dimethylphenyl] aryl diphosphate compounds, method for their production & resin compositions of the same
EP2468814A1 (en) Novel Phosphorus Compound, Method of Preparing the Same and Flame Retardant Thermoplastic Resin Composition Including the Same
US4274998A (en) Diester of 3,5,3',5'-tetrabromo-bisphenol A with halogenated aromatic carboxylic acid
KR20090073474A (en) Novel phophoric flame retardandt, method for preparing the same and flameproof thermoplastic resin composition containing the same
EP0617042A1 (en) Organic phosphorus compounds and flame-retarded resin compositions containing the same
US4567218A (en) Halogenated bisphenol A ether flame retardant for ABS polymers
KR100426301B1 (en) Flame-retarded thermosetting resin composition
JP2911285B2 (en) Flame retardant thermoplastic resin composition
KR19980085530A (en) Bis [2,4-bis (1,1-dimethylethyl) phenyl-2,6-dimethylphenyl] aryl diphosphate compound, its preparation method and resin composition containing the same
KR19980075742A (en) Tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] aryl phosphate compound
KR19980085531A (en) Tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] aryl diphosphate compound, a process for producing the same, and a resin composition containing the same
JP2911335B2 (en) Flame retardant thermoplastic resin composition
JP3026377B2 (en) Organophosphorus compound and flame-retardant heat-stable resin composition containing the same
JPH0528743B2 (en)
US4602111A (en) Polybromo tertiary amine
JPH06321974A (en) Organophosphorus compound and flame-retardant composition containing the compound
KR19980076753A (en) Bis [2,4-bis (1,1-dimethylethyl) phenyl-2,6-dimethylphenyl] aryl diphosphate compound and preparation method thereof
US6414060B1 (en) Flame retardant polycarbonate-ABS polymer compositions
KR100490839B1 (en) Styrene based thermoplastic resin composition having superior fireproof properties
JP3736584B2 (en) Flame retardant, method for producing the flame retardant, and flame retardant thermoplastic resin composition containing the flame retardant

Legal Events

Date Code Title Description
WAP Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1)