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GB2211850A - Flame retardant polymer composition - Google Patents

Flame retardant polymer composition Download PDF

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Publication number
GB2211850A
GB2211850A GB8725573A GB8725573A GB2211850A GB 2211850 A GB2211850 A GB 2211850A GB 8725573 A GB8725573 A GB 8725573A GB 8725573 A GB8725573 A GB 8725573A GB 2211850 A GB2211850 A GB 2211850A
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Prior art keywords
carbon atoms
group
metal
composition
carbons
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GB8725573D0 (en
Inventor
James Gainer
Brian George Clubley
Richard John Dellar
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Novartis AG
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Ciba Geigy AG
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Priority to GB8725573A priority Critical patent/GB2211850A/en
Publication of GB8725573D0 publication Critical patent/GB8725573D0/en
Publication of GB2211850A publication Critical patent/GB2211850A/en
Withdrawn legal-status Critical Current

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    • 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
    • C08K5/59—Arsenic- or antimony-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
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
    • 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
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
    • C08K5/5333—Esters of phosphonic acids
    • 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
    • C08K5/55—Boron-containing compounds

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  • 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

Halogen free polymer compositions comprise as flame retardant a metal or metalloid salt of a phosphonic acid of formula <IMAGE> in which R is straight or branched chain alkyl having 1 to 18 carbons, cycloalkyl having 5 or 6 carbons, alkenyl having 2 to 6 carbons, aryl having 6 to 10 carbons, aralkyl having 7 to 11 carbons, aralkenyl having 8 to 12 carbons, or monocyclic or fused bicyclic O, N or S heterocyclic, R being optionally substituted by one or more halogen, hydroxyl, amino, alkoxy, carboxy or carbalkoxy; and R<1> is hydrogen, straight or branched chain alkyl having 1 to 8 carbons, aryl having 6 to 10 carbons or aralkyl having 7 to 11 carbons, R<1> being optionally substituted by one or more halogen, hydroxyl, amino, alkoxy, carboxy or carbalkoxy; and wherein the metal or metalloid is selected from Groups IIA, IIB, IIIA, IVA, IVB, VA and VIII of the Periodic Table (Fisher Scientific Company 1968) provlded that when the metal is an alkaline earth metal and R is alkyl or aryl, R is substituted by one of the above substituents and further provided that when R is alkyl with 1 to 3 carbon atoms it is substituted by amino, alkoxy, carboxy or carbalkoxy.

Description

Flame Retardant Polymer Composition The present invention relates to flame retardant polymer compositions.
Polymers, particularly halogen-free polymers, are commonly made more flame retardant by incorporating therein a phosphoruscontaining compound, a halogen-containing compound or a mixture thereof. Some polymers are processed at high temperatures of, for example, 250"C or higher, and many known flame retardants are not suitable under these conditions because they are too volatile, or not sufficiently thermally stable.
We have now found a class of compounds which are thermally stable at high temperatures and which can be used as flame retardants in a wide range of plastics. The compounds also do not give unwanted plasticising properties to rigid polymers.
Accordingly the present invention provides a composition comprising a halogen-free polymer and a flame retardant amount of a metal or metalloid salt of a phosphonic acid of the general formula I
in which R is a straight or branched chain alkyl group having 1 to 18 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aralkyl group having 7 to 11 carbon atoms, an aralkenyl group having 8 to 12 carbon atoms, or a monocyclic or fused bicyclic heterocyclic group having one or more of 0, N and S as hetero atoms, R being unsubstituted or substituted by one or more halogen, hydroxyl, amino, alkoxy, carboxy or carbalkoxy groups or combinations of these groups ;; lnd R1 is hydrogen, a straight or branched chain alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms or an aralkyl group having 7 to ii carbon atoms, R1 being unsubstituted or substituted by one or more halogen, hydroxyl, amino, alkoxy, carboxy or carbalkoxy groups; and wherein the metal or metalloid is selected from Groups IIA, IIB, IIIA, IVA, IVB, VA and VIII of the Periodic Chart of Elements (Fisher Scientific Company 1968) provided that when the metal is an alkaline earth metal and R is an alkyl or aryl group, R is substituted by one of the groups, listed above, and further provided that when R is an alkyl group with 1 to 3 carbon atoms it is substituted by an amino, alkoxy, carboxy or carbalkoxy group.
When R is an alkyl group it preferably has 4 to 12 carbon atoms and may be, for example, butyl, pentyl, octyl, decyl or dodecyl.
When R is a cycloalkyl group it may be a cyclopentyl or cyclohexyl group.
When R is an alkenyl group it may be a vinyl, propenyl, butenyl, pentenyl or hexenyl group.
When R is an aryl group, it may be a phenyl or naphthyl group.
When R is an aralkyl group it may be a benzyl, phenyl ethyl or naphthylmethyl group.
When R is a heterocyclic or heteroalkyl group it may be, for example, a furan, thiophene, pyrrole, pyrazole, pyrazolone, imidazole, imidazolone, triazole, oxazole, isoxazole, pyridine, pyridone, pyrimidine, pyrimidinone, pyridazine, pyridazinone, triazine, benzimidazole, benzimidazolone, benzothiazole or benzoxazole group.
When R1 is an alkyl group it may be a methyl, ethyl, butyl, pentyl, hexyl or octyl group.
The metal or metalloid may be, for example, magnesium, calcium, barium, zinc, boron, aluminium, tin, antimony, iron, cobalt, nickel or titanium.
Preferably the metal is magnesium or aluminium, most preferably aluminium.
The salt may be a simple ionic compound formed between anions of the phosphonic acid and cations of the metal or metalloid.
Where R' is H and the metal or metalloid has a valency greater than one, the salt may have a polymeric structure as represented by the general formula (II)
where R is as defined above, M is the metal or metalloid, n has a value one less than the valency of M and m is from 2 to 100 and where each group
is attached to M atoms only.
Non limiting Examples of phosphonic acid salts of the present invention are given below.
The phosphonic acid salts are either known, or can be readily prepared by known methods. The phosphonic acid or its sodium salt-may be reacted with the metal carbonate or oxide, e.g.
The sodium salt of the phosphonic acid or partial ester may also be reacted in aqueous solution with a water-soluble metal salt, e.g.
Other processes include reacting an ester of the phosphonic acid with a metal halide or metal alkoxide, e.g.
The amount of phosphonic acid salt added to the polymer as a flame retardant may be varied over a wide range. Usually from 0.1 to 100 parts are used per 100 parts by weight of polymer.
Preferably there are used 0.5 to 30 parts and, most preferably, from 2 to 20 parts by weight per 100 parts by weight of polymer.
The optimum amount used depends on the nature of the polymer and the actual salt used and may be readily determined by simple experiment. However, because the salts are generally effective at low levels of addition they produce less unwanted effects in the polymer than other known flame retardant additives.
The salts may be used in various physical forms depending on the polymer used and the desired properties. For instance the salts may be ground to a finely divided form to enable better dispersion throughout the polymer. Also, mixtures of different salts may be used if desired.
The phosphonic acid salts may be used in various polymers.
Examples of polymers which may be rendered flame retardant are: 1. Polyphenylene oxides and sulfides, and blends of these polymers with polyamides, polyesters such as polybutylene terephthalate, polystyrene graft and copolymers such as high impact polystyrene, EPDM copolymers with rubbers.
2. Polyurethanes which are derived from polyethers, polyesters or polybutadiene with terminal hydroxyl groups on the one side and aliphatic or aromatic polyisocyanates on the other side including polyisocyanurates, as well as precursors thereof.
3. Polyamides and copolyamides which are derived from diamines and dicarboxylic acids and/or from aminocarboxylic acids or the corresponding lactams, such as polyamide 4, polyamide 6, polyamide 6/6, polyamide 6/10, polyamide 11, polyamide 12, poly-2,4,4-trimethylhexamethylene terephthalamide or poly-m-phenylene isophthalamide, as well as copolymers thereof with polyethers, such as for instance, with polyethylene glycol, polypropylene glycol or polytetramethylene glycols.
4. Polyesters which are derived from dicarboxylic acids and dialcohols and/or from hydroxycarboxylic acids or the corresponding lactones, such as polyethylene terephthalate, polybutylene terephthalate, poly-1,4-dimethylol-cyclohexane terephthalate and polyhydroxybenzoates as well as block-copolyether-esters derived from polyethers having hydroxyl end groups.
5. Unsaturated polyester resins which are derived from copolyesters of saturated and unsaturated dicarboxylic acids ith polyhydric alcohols and vinyl compounds as crosslinking agents, and also halogen-containing modifications thereof of low inflammability.
6. Polystyrene.
7. Graft copolymers of styrene, such as, for example, styrene on polybutadiene, styrene and acrylonitrile on polybutadiene, styrene and alkyl acrylates or methacrylates on polybutadiene, styrene and acrylonitrile on ethylene/propylene/diene terpolymers, styrene and acrylonitrile on polyacrylates or polymethacrylates, styrene and acrylonitrile on acrylate/ butadiene copolymers, as well as mixtures thereof with random copolymers of styrene or s(-methylstyrene with dienes or acrylic derivatives, for instance the copolymer mixtures known as ABS-, MBS-, ASA- or AES-copolymers.
8. Cross-linked epoxide resins which are derived from polyepoxides, for example, from bis-glycidyl ethers or from cycloaliphatic diepoxides.
9. Polycarbonates and blends thereof with other polymers such as ABS.
The compositions of the invention may also contain other conventional ingredients, such as heat stabilisers, light stabilisers, ultra-violet light absorbers, anti-oxidants, anti-static agents, preservatives, adhesion promotors, fillers, pigments, lubricants, blowing agents, fungicides, plasticisers, processing aids, other fire-retardant additives and smoke suppressants.
Other fire retardant additives which may be used with the phosphonic acid salts include phosphorus containing esters and salts such as triaryl phosphates, alkyl aryl phosphates and ammonium polyphosphate, halogen, especially bromine and chlorine containing compounds such as haloalkyl phosphate and phosphonate esters, antimony oxide, hydrated alumina, bismuth oxide, molybdenum oxide, or mixtures of these compounds with zinc and/or magnesium oxide, hydroxide or salts.
The invention is illustrated by the following Examples.
-Example 1 13.4g (0.1 mole) anhydrous aluminium chloride are added in portions to 49.2g (0.3 mol) diethylvinylphosphonate maintaining the reaction temperature below 40"C using ice-water bath cooling.
On completion of addition, reaction mixture is warmed to 50"C for 2 hours, cooled to 250C and diluted with acetone (100 millilitres). The solid product is collected, washed with acetone and dried to constant weight. There are obtained 35.6g of product having melting point > 250 C and has elemental analysis: C; 31.65%, H; 5.36%, Al; 6.51%, P; 21.48%. Calculated for C12H24A10gP3: C; 33.33%, H; 5.56%, Al; 6.25%, P; 21.53%.
Example 2 Using the procedure described in Example 1, reaction of 13.4g (0.1 mole) anhydrous aluminium chloride with 67.2g (0.3 mole) triethylphosphono acetate gives 50.0g of product having melting point > 250 C and has elemental analysis: C; 34.86%, H; 5.91%, Al; 4.25%, P; 14.65%. Calculated for C18H36Al015P3: C; 35.29%, H; 5.88%, Al; 4.41%, P; 15.20%.
Example 3 Using the procedure described in Example 1, reaction of 82.5g (0.33 mole) triethylphosphonocrotonate with 13.4g (0.1 mole) anhydrous aluminium chloride gives 48.0g of product having melting point > 250 C and has elemental analysis C; 41.15%, H;6.16%, Al; 3.76%, P; 13.26%. Calculated for C24H42A1O15P3: C; 41.74%, H; 6.09%, Al; 3.91%, P; 13.48%.
Example 4 Using the procedure described in Example 1, reaction of 55.8g (0.3 mole) dimethylphenylphosphonate with 13.4g (0.1 mole) anhydrous aluminium chloride gives 44.5g of product having melting point > 250 C and has elemental analysis: C; 45.24%, H; 4.48%, Al; 5.16%, P; 16.82%. Calculated for C21H24A10gP3.H20 C; 45.16%, H; 4.66%, Al; 4.83%, P; 16.66%.
Example 5 A solution of 12.6g (0.15 mole) magnesium carbonate in 100 millilitres of water is added dropwise to a solution of 56.4g (0.3 mole) 0(2-hydroxyphenyl)methylphosphonic acid in 100 millilitres of H20 at 25"C. After completion of addition, the reaction mixture is slowly warmed to reflux temperature and heated for a further period of 6 hours. The reaction mixture is cooled, filtered and the solid product is washed with acetone and dried to constant weight. There are obtained 53.3g of product having melting point 180-185"C and has elemental analysis: C; 40.57%, H; 4.55%, P; 14.77%. Calculated for C14H18M40gP2: C; 40.35%, H; 4.32%, P; 14.89%.
Example 6 Using the procedure described in Example 1, reaction of 13.4g (0.1 mole) anhydrous aluminium chloride with 62.4g (0.3 mole) diethylpentylphosphonate gives 35.2g of product having melting point > 250 C.
Example 7 Using the procedure described in Example 1, reaction of 11.1g (0.083 mole) anhydrous aluminium chloride with 62.5g (0.25 mole) diethyloctylphosphonate gives 38.3g of product having melting point > 200 C.
Example 8 Using the procedure described in Example 1, reaction of 33.4g (0.25 mole) anhydrous aluminium chloride with 171.0g (0.75 mole) diethylbenzylphosphonate gives 106.2g of product having melting point > 250 C and has elemental analysis: C; 48.39%, H; 5.89%, Al; 4.38%, P; 14.65%. Calculated for C27H36AlOgP3.ZH2O: C; 49.09%, H; 6.06%, Al; 4.09%, P; 14.09%.
Examples 9 to 16 Compositions are made up by melt compounding at a temperature of 230 C 100 parts by weight of the plastics based on polystyrene and polyphenylene oxide, sold under the Trade Name Noryl 731, and 12 parts by weight of the salt indicated in Table 1.
The Oxygen Index (OI) is measured according to BS.2782:part l:method 141A:1983 and the flammability tested according to the "Test for Flammability of Plastics Materials - UL 94", February 1, 1984. The results are shown in Table 1.
Table 1
Example I Salt from Example I OI % I UL 94 l - None 22.3 HB I 9 1 1 1 24.2 I VE 1 1 10 | 1 2 I 23.1 1 VE 1 I 11 1 3 1 27.6 I VE 1 12 1 4 1 26.1 I VE 1 1 13 1 5 1 22.8 I VE 1 1 14 1 6 1 24.7 1 VE 1 1 15 i 7 1 24.8 I VE 1 I 1 16 1 8 1 27.4 I VE 1 I These results show the flame retardant effect of the salts by virtue of an increase in OI and a higher rating in the UL 94 test, where VEO is the highest rating followed by VEl, then VE2 and finally HB (complete burning of sample).

Claims (8)

Claims
1. A composition comprising a halogen-free polymer and a flame retardant amount of a metal or metalloid salt of a phosphonic acid of the general formula I:
in which R is a straight or branched chain alkyl group having 1 to 18 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aralkyl group having 7 to 11 carbon atoms, an aralkenyl group having 8 to 12 carbon atoms,or a monocyclic or fused bicyclic heterocyclic group having one or more of O, N and S as hetero atoms, R being unsubstituted or substituted by one or more halogen, hydroxyl, amino, alkoxy, carboxy or carbalkoxy groups or combinations of these groups; and R1 is hydrogen, a straight or branched chain alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms or an aralkyl group having 7 to 11 carbon atoms, R1 being unsubstituted or substituted by one or more halogen, hydroxyl, amino, alkoxy, carboxy or carbalkoxy groups; and wherein the metal or metalloid is selected from Groups IIA, IIB, IIIA, IVA, IVB, VA and VIII of the Periodic Chart of Elements (Fisher Scientific Company 1968) provided that when the metal is an alkaline earth metal and R is an alkyl or aryl group, R is substituted by one of the groups, listed above, and further provided that when R is an alkyl group with 1 to 3 carbon atoms it is substituted by an amino, alkoxy, carboxy or carbalkoxy group.
2. A composition. as claimed in Claim 1 in which R represents C4-C12 alkyl.
3. A composition as claimed in claim 1 in which the metal or metalloid is magnesium, calcium, barium, zinc, boron, aluminium, tin, antimony, iron, cobalt, nickel or titanium.
4. A composition as claimed in claim 1 in which the metal is aluminium.
5. A composition as claimed in claim 1 in which the amount of salt is from 0.1 to 100 parts per 100 parts by weight of polymer.
6. A composition as claimed in claim 5 in which the amount of salt is from 0.5 to 30 parts per 100 parts by weight of polymer.
7. A composition as claimed in claim 6 in which the amount of salt is from 2 to 20 parts per 100 parts by weight of polymer.
8. A composition as claims in claim 1 in which the polymer is a polyphenylene oxide or sulphide, or a blend of such a polymer with another polymer, a polyurethane or polyisocyanurate, a polyamide, a polyester or unsaturated polyester resin, polystyrene, a graft copolymer or terpolymer of styrene with one or more other monomers, or a cross-linked epoxide resin.
GB8725573A 1987-10-31 1987-10-31 Flame retardant polymer composition Withdrawn GB2211850A (en)

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GB2211850A true GB2211850A (en) 1989-07-12

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2665171A1 (en) * 1990-07-30 1992-01-31 Rhone Poulenc Chimie Polyamide-based compositions making it possible to obtain moulded articles which have good flame resistance
US5102932A (en) * 1990-04-03 1992-04-07 Ciba-Geigy Corporation Flame retardants for polymers
WO2004046235A1 (en) * 2002-11-21 2004-06-03 Ciba Specialty Chemicals Holding Inc. Flame retardant composition comprising a phosphonic acid metal salt and a nitrogen-containing compound
CN100338125C (en) * 2002-11-21 2007-09-19 西巴特殊化学品控股有限公司 Flame retardant composition comprising a phosphonic acid metal salt and a nitrogen-containing compound
US8889773B2 (en) 2010-06-24 2014-11-18 Icl-Ip America Inc. Metal phosphonate flame retardant and method producing thereof
JP2016500687A (en) * 2012-10-18 2016-01-14 ダウ グローバル テクノロジーズ エルエルシー Phosphorus-containing carboxylic acid aluminum salt flame retardant

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1081825A (en) * 1961-04-14 1967-09-06 Geigy Ag J R Metal derivatives of dialkylhydroxyphenylalkylphosphonic acids and phosphonic acid half-esters
GB1325496A (en) * 1969-08-29 1973-08-01 Ciba Geigy Ag Stabilization of organic materials
GB1473909A (en) * 1973-09-13 1977-05-18 Ciba Geigy Ag Metal complexes of alpha-aminophosphonic acid half-esters and of alpha-aminophosphinic acids
GB2048278A (en) * 1979-04-20 1980-12-10 Wiggins Teape Group Ltd Photographic Bass Papers
GB1601884A (en) * 1977-03-10 1981-11-04 Baker Ag Processes for the production of a flameproofing insulating layer
EP0064039A1 (en) * 1981-04-16 1982-11-03 Neste Oy Use of an ethylene polymer composition for the production of film

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1081825A (en) * 1961-04-14 1967-09-06 Geigy Ag J R Metal derivatives of dialkylhydroxyphenylalkylphosphonic acids and phosphonic acid half-esters
GB1325496A (en) * 1969-08-29 1973-08-01 Ciba Geigy Ag Stabilization of organic materials
GB1473909A (en) * 1973-09-13 1977-05-18 Ciba Geigy Ag Metal complexes of alpha-aminophosphonic acid half-esters and of alpha-aminophosphinic acids
GB1601884A (en) * 1977-03-10 1981-11-04 Baker Ag Processes for the production of a flameproofing insulating layer
GB2048278A (en) * 1979-04-20 1980-12-10 Wiggins Teape Group Ltd Photographic Bass Papers
EP0064039A1 (en) * 1981-04-16 1982-11-03 Neste Oy Use of an ethylene polymer composition for the production of film

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5102932A (en) * 1990-04-03 1992-04-07 Ciba-Geigy Corporation Flame retardants for polymers
FR2665171A1 (en) * 1990-07-30 1992-01-31 Rhone Poulenc Chimie Polyamide-based compositions making it possible to obtain moulded articles which have good flame resistance
WO2004046235A1 (en) * 2002-11-21 2004-06-03 Ciba Specialty Chemicals Holding Inc. Flame retardant composition comprising a phosphonic acid metal salt and a nitrogen-containing compound
CN100338125C (en) * 2002-11-21 2007-09-19 西巴特殊化学品控股有限公司 Flame retardant composition comprising a phosphonic acid metal salt and a nitrogen-containing compound
US8889773B2 (en) 2010-06-24 2014-11-18 Icl-Ip America Inc. Metal phosphonate flame retardant and method producing thereof
JP2016500687A (en) * 2012-10-18 2016-01-14 ダウ グローバル テクノロジーズ エルエルシー Phosphorus-containing carboxylic acid aluminum salt flame retardant

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