EP0275280A4 - NOVEL THIOPHOSPHATE ESTER AND POLYURETHANE OR PREPOLYMER FOAM CONTAINING TRI- AND BI- (2,4,6-TRIBROMOPHENOXY) (THIO) PHOSPHATE. - Google Patents
NOVEL THIOPHOSPHATE ESTER AND POLYURETHANE OR PREPOLYMER FOAM CONTAINING TRI- AND BI- (2,4,6-TRIBROMOPHENOXY) (THIO) PHOSPHATE.Info
- Publication number
- EP0275280A4 EP0275280A4 EP19870904666 EP87904666A EP0275280A4 EP 0275280 A4 EP0275280 A4 EP 0275280A4 EP 19870904666 EP19870904666 EP 19870904666 EP 87904666 A EP87904666 A EP 87904666A EP 0275280 A4 EP0275280 A4 EP 0275280A4
- Authority
- EP
- European Patent Office
- Prior art keywords
- prepolymer
- compound
- mixture
- formula
- tribromophenoxy
- 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- Withdrawn
Links
- 229920005830 Polyurethane Foam Polymers 0.000 title claims abstract description 13
- 239000011496 polyurethane foam Substances 0.000 title claims abstract description 13
- -1 thiophosphate ester Chemical class 0.000 title claims abstract description 11
- 229920001730 Moisture cure polyurethane Polymers 0.000 title claims description 5
- 229910019142 PO4 Inorganic materials 0.000 title description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 title description 4
- 239000010452 phosphate Substances 0.000 title description 4
- UYYBTSWSNFBXPF-UHFFFAOYSA-N 1,3,5-tribromo-2-(2,4,6-tribromophenoxy)sulfanyloxybenzene Chemical compound BrC1=C(OSOC2=C(C=C(C=C2Br)Br)Br)C(=CC(=C1)Br)Br UYYBTSWSNFBXPF-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 239000000203 mixture Substances 0.000 claims abstract description 32
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000005864 Sulphur Substances 0.000 claims abstract description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 239000001301 oxygen Substances 0.000 claims abstract description 10
- 239000006260 foam Substances 0.000 claims description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 239000012948 isocyanate Substances 0.000 claims description 12
- 150000002513 isocyanates Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 9
- 150000007530 organic bases Chemical class 0.000 claims description 6
- 229920005862 polyol Polymers 0.000 claims description 6
- 150000003077 polyols Chemical group 0.000 claims description 6
- 230000000979 retarding effect Effects 0.000 claims description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 239000000654 additive Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 239000000779 smoke Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 238000002485 combustion reaction Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000003466 anti-cipated effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
- 150000005691 triesters Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000036647 reaction Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- OWNZHTHZRZVKSQ-UHFFFAOYSA-N tribromo(sulfanylidene)-$l^{5}-phosphane Chemical compound BrP(Br)(Br)=S OWNZHTHZRZVKSQ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 1
- PKLRDZGLQIGNOJ-UHFFFAOYSA-N BrC1=C(C(=CC(=C1)Br)Br)O.[BrH]1C=CC=C1 Chemical compound BrC1=C(C(=CC(=C1)Br)Br)O.[BrH]1C=CC=C1 PKLRDZGLQIGNOJ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- JOCBASBOOFNAJA-UHFFFAOYSA-N N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid Chemical compound OCC(CO)(CO)NCCS(O)(=O)=O JOCBASBOOFNAJA-UHFFFAOYSA-N 0.000 description 1
- WGOGKJYRAWQHLR-UHFFFAOYSA-N P(=S)(O)(O)O.[BrH]1[BrH]CC=C1 Chemical compound P(=S)(O)(O)O.[BrH]1[BrH]CC=C1 WGOGKJYRAWQHLR-UHFFFAOYSA-N 0.000 description 1
- CFDZSJXVBSLSBV-UHFFFAOYSA-N P(=S)(O)(O)O.[BrH]1[BrH][BrH]C=C1 Chemical compound P(=S)(O)(O)O.[BrH]1[BrH][BrH]C=C1 CFDZSJXVBSLSBV-UHFFFAOYSA-N 0.000 description 1
- IUSGATWWECUUDG-UHFFFAOYSA-N P(O)(O)O.[BrH]1[BrH][BrH]C=C1 Chemical compound P(O)(O)O.[BrH]1[BrH][BrH]C=C1 IUSGATWWECUUDG-UHFFFAOYSA-N 0.000 description 1
- 206010063493 Premature ageing Diseases 0.000 description 1
- 208000032038 Premature aging Diseases 0.000 description 1
- 241000022563 Rema Species 0.000 description 1
- 235000017899 Spathodea campanulata Nutrition 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- 150000002013 dioxins Chemical class 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- 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
- 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
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/18—Esters of thiophosphoric 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
- C08K5/5398—Phosphorus bound to sulfur
Definitions
- This invention relates to compounds, processes and products.
- this invention relates to broninated phenol esters and to their use in mixtures with prepolymers in order to improve certain characteristics of materials to be synthesized from such prepolymers.
- An additive of this invention is one compound or a mixture of compounds chosen from a group of brominated phenol esters which ha ve exhibited f ire retardent , surf actant and plasticising properties.
- a method of producing fire retardent polyurethane foam wherein the additive is mixed into either an isocyanate prepolymer or a polyol prepolymer of the polyur ⁇ thane system, and the modified prepolymer thus formed is in turn mixed with polyol prepolymer or isocyanate prepolymer respectively to produce polyurethane foam.
- the present invention provides a polyurethane foam containing a fire retarding amount of a mixture of a compound of formula XI set out in the accompanying drawings and a compound of formula XII set out in the accompanying drawings wherein X 1 and S 2 are oxygen or sulphur and RO- is 2,4,6-tribromophenoxy.
- the present invention also provides a polyurethane foam prepolymer containing a fire retarding amount, with respect to a foam which can be produced, of a mixture of a compound of formula XI set out in the accompanying drawings and a compound of fornula XII set out in the accompanying drawings wherein X 1 and X 2 are oxygen or sulphur and RO- is 2,4,6- tribromophenoxy. Preferably X 1 and X 2 are both oxygen or both sulphur.
- the foam or prepolymer may additionally include a compound of formula V set out in the accompanying drawings.
- the prepolymer may be a polyol or isocyanate. The latter is preferred.
- the prepolymer preferably comprises an organic base.
- That base is preferably selected from triethylamine, ethylene diamine, and triethano 1 amine.
- said compound of formula XI is present in said mixture as from 70 to 80%.
- said compound of formula XII is present in said mixture as from 20 to 30%. by weight.
- said compound of formula XIII is present in said mixture as from 3 to 8% by weight.
- said mixture is present in said prepolymer as from 21 ⁇ 2 to 20 preferably 8 to 10% by weight.
- said organic base is present in said mixture as from 6 to 8% by weight.
- the present invention also provides the compound of formula II set out in the accompanying drawings wherein RO- is 2,4,6 -tribromophenoxy and mixtures containing same.
- the present invention provides in a preferred aspect for use of five brominated phenol esters with compound of formulae I-V set out in the accompanying drawings.
- Compound II which is the preferred component of the additive does not seem to have been previously described.
- Compound IV as a fire retardent does not seem to have been described.
- One previous publication [Benbow & Cullis (1975), Combustion and Flame, v.24, p.217-230] describes the use of Compound III for fire retardation of flexible polyurethane foam. Its use was considered by those authors to be unsatisfactory, primarily because of poor solubility.
- the acidity introduced by either Compound II or I V partly neutralizes amine catalysts in the system resulting in a reduced rate of foaming when polyol and isocyanate are mixed.
- This ef f ect may be at l east in part reduced by addition of an organic base, severa l of which ha ve been tested successful ly.
- a t t empera tur es pr oduced b y a n exoth ermic react ion when isocyanate and polyol prepolymers are mixed, isocyanate is released to recombine immediately with hydroxyl residues to f orm the urethane l inkages.
- the diester (Compound II or I V) is not onl y ful ly solubil ized but also helps to solubilize the triesters, both phosphate (Compound I or III) and phosphite (Compound V), possibly by pi-bonding.
- the f ol lowing example provides a process f or manufacture of the additive.
- the esters were manufactured in acetone solution by esterif ication of bromol (2,4 ,6- tribromophenol) produced in situ from phenol.
- EXAMPLE In a first procedure, phenol in acetone was mixed with bromine (1:5.2 phenol/bromine w/w) to form bromol, then this mixture was mixed with phosphorus tribromide (1.05:1 pheno 1 /b romi de w/w) at a temperature betwen 15°C and 30°C, thus forming a solution of tribromol phosphite.
- the initial phenol concentration in acetone was about 80£ w/w, but this value was not critical and was sometimes varied widely according to the mechanics of mixing. This solution was stored under nitrogen until used.
- phenol in acetone was mixed with thiophosphoryl bromide in bromine solution while controlling the temperature to below 30°C.
- Reactant ratios were 1:5.2:1.05-1.09 (w/w/w phenol/bromine/bromide), this forming a mixed solution of tribromol thiophosphate (70-80% ) with the balance being dibromol thiophosphate.
- This solution was then blended with the phosphite solution from the first process (20:1 w/w phosphate/phosphite) and an amount of organic base (triethylamine) sufficient to neutralize 85-95 ⁇ of residual acidity.
- This mixture was then poured into water whereupon a white flocculated precipitate separated immediately. This precipitate was then dried to reduce water content below 5 i w/w.
- the final mixture then became Compounds I/II/V (approx. 15/5/1).
- Those other characteristics include (1 ) enhanced surfactancy of isocyanate prepolymer which tends to improve cell structure and to reduce or remove the need for silicone, (2) improved adhesion to substrate expected from lowering of silicone addition, (3) reduced need for polymerization catalysts, and (4) anticipated marked suppression of embrittlement and catastrophic failure caused by normal or premature aging.
- Compounds I and II are superior to Compounds III and IV with respect to smoke production, catalysis and solubility, but are inferior with respect to flammability, stability to aerial oxidation and cost.
- Compound V is a fire and smoke suppressant in its own right but in this application it is provided mainly as an antioxidant for mixing with either of the other compounds to confer long term stability. The effects of each ⁇ f these compounds seemed to be proportional to their content.
- Type S Bayer Desmodur 44V20 + Bayertherm 4150 (1:1 v/v)
- Type G Lackfa Lamoltan
- Type K Bayer Desmodur 44V20: Mixture A (100:16 w/w) + Bayertherm 4150 (1,1 v/v),
- fixture B performed similarly.
- Type K is the standard type S a l tered on l y by addition of the additive of this invention.
- the table represents the direct comparison of commercial ly available standard and premium grade foams with the those provided herein.
- Values for type S have been arbitrarily set at 10; optimum performance would be zero. Thus, low values are preferred.
- Both type G and type K behave markedly better than type S. With respect to fire and smoke type K is inferior to type G, but type K is so far superior to type G with respect to structural integrity that its overall performance is significantly better than type G. Type K catches fire and burns at a substantially lower temperature than the other two types.
- Type K fires are far less dramatic than those of type S, but it is anticipated that in widespread use the most significant advance of type K is to be its relatively low potential to produce those gaseous products which are proven potent killers.
- Use of polyhalogenated diaryl ethers such as those used in type G is being voluntarily restricted pending availability of satisfactory alternatives because such compounds are known or suspected precursors of di ⁇ xins.
- Additives ⁇ f the type provided herein have no inherent capacity to produce dioxins at the temperatures anticipated in any combustion possibly sustained by type K foam.
- These inventions provided herein have contributed to significant advances in the applicability of polyurethane f oam to situations currently precluded because of flammability.
- These inventions also provide materials with surfactant and plasticising properties which may be of major, rather than incidental, interest in various applications. The claims form part of the disclosure of this specification.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPH681086 | 1986-07-09 | ||
| AU6810/86 | 1986-07-09 | ||
| AUPI093887 | 1987-03-17 | ||
| AU938/87 | 1987-03-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0275280A1 EP0275280A1 (en) | 1988-07-27 |
| EP0275280A4 true EP0275280A4 (en) | 1988-11-16 |
Family
ID=25643124
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP19870904666 Withdrawn EP0275280A4 (en) | 1986-07-09 | 1987-07-09 | NOVEL THIOPHOSPHATE ESTER AND POLYURETHANE OR PREPOLYMER FOAM CONTAINING TRI- AND BI- (2,4,6-TRIBROMOPHENOXY) (THIO) PHOSPHATE. |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0275280A4 (pt) |
| JP (1) | JPH01500908A (pt) |
| KR (1) | KR880701725A (pt) |
| DK (1) | DK128088D0 (pt) |
| ES (1) | ES2004771A6 (pt) |
| GR (1) | GR871082B (pt) |
| PT (1) | PT85297B (pt) |
| WO (1) | WO1988000199A1 (pt) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2917089A (en) * | 1988-01-04 | 1989-08-01 | Richard John Maerschel | Compounds or mixtures formed by reaction of 2,4,6-tribromophenyl(thio)phosphate esters with boric acid orborates and use as fire retardant |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2857308A (en) * | 1956-11-15 | 1958-10-21 | Monsanto Chemicals | Method of destroying nematodes employing phosphorodithioates |
| US4021406A (en) * | 1973-05-21 | 1977-05-03 | M & T Chemicals Inc. | Flame retardant compositions |
| US4059655A (en) * | 1975-11-24 | 1977-11-22 | Ppg Industries, Inc. | Process for preparing halogenated diaryl hydrogen phosphates |
| DE2809773A1 (de) * | 1977-03-30 | 1978-10-05 | Teijin Ltd | Vollstaendig aromatische polyamidfasern und verfahren zu ihrer herstellung |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1401863A (en) * | 1972-11-02 | 1975-08-06 | Gen Electric | Flame retardant polyester resin compositions |
| US4258169A (en) * | 1980-03-26 | 1981-03-24 | The Upjohn Company | Polyisocyanate compositions containing in-situ formed pyrophosphate mold release agent and process of making |
| DE3127914A1 (de) * | 1981-07-15 | 1983-02-03 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von flammwidrigen polyutheran- und/oder polyisocyanuratgruppen enthaltenden schaumstoffen |
| NL8301569A (nl) * | 1983-05-04 | 1984-12-03 | Gen Electric | Polymeermengsel met vlamwerende eigenschappen, geschikt voor draadmantelextrusie, op basis van polyfenyleenoxyde en elektrisch geleidende draad. |
| US4477600A (en) * | 1983-09-23 | 1984-10-16 | Stauffer Chemical Company | Polyurethane foams having low scorch discoloration |
| JPH0629313B2 (ja) * | 1984-12-07 | 1994-04-20 | 武田薬品工業株式会社 | 難燃性軟質ウレタンフォームの製造法 |
| US4616044A (en) * | 1985-01-25 | 1986-10-07 | Stauffer Chemical Company | Heat laminatable polyether urethane foam |
-
1987
- 1987-07-09 PT PT85297A patent/PT85297B/pt unknown
- 1987-07-09 KR KR1019880700260A patent/KR880701725A/ko not_active Application Discontinuation
- 1987-07-09 JP JP62504329A patent/JPH01500908A/ja active Pending
- 1987-07-09 WO PCT/AU1987/000212 patent/WO1988000199A1/en not_active Application Discontinuation
- 1987-07-09 ES ES8702232A patent/ES2004771A6/es not_active Expired
- 1987-07-09 EP EP19870904666 patent/EP0275280A4/en not_active Withdrawn
- 1987-07-09 GR GR871082A patent/GR871082B/el unknown
-
1988
- 1988-03-09 DK DK128088A patent/DK128088D0/da not_active Application Discontinuation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2857308A (en) * | 1956-11-15 | 1958-10-21 | Monsanto Chemicals | Method of destroying nematodes employing phosphorodithioates |
| US4021406A (en) * | 1973-05-21 | 1977-05-03 | M & T Chemicals Inc. | Flame retardant compositions |
| US4059655A (en) * | 1975-11-24 | 1977-11-22 | Ppg Industries, Inc. | Process for preparing halogenated diaryl hydrogen phosphates |
| DE2809773A1 (de) * | 1977-03-30 | 1978-10-05 | Teijin Ltd | Vollstaendig aromatische polyamidfasern und verfahren zu ihrer herstellung |
Non-Patent Citations (2)
| Title |
|---|
| CHEMICAL ABSTRACTS, vol. 93, no. 26, 29th December 1980, page 96, abstract no. 241255n, Columbus, Ohio, US; A.L. LABUTIN et al.: "Fire-resistant polyurethane sealant", & KAUCH. REZINA 1980, (8), 29-31 * |
| See also references of WO8800199A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0275280A1 (en) | 1988-07-27 |
| JPH01500908A (ja) | 1989-03-30 |
| PT85297B (en) | 1989-10-12 |
| WO1988000199A1 (en) | 1988-01-14 |
| GR871082B (en) | 1987-11-12 |
| KR880701725A (ko) | 1988-11-04 |
| DK128088A (da) | 1988-03-09 |
| PT85297A (en) | 1987-08-01 |
| DK128088D0 (da) | 1988-03-09 |
| ES2004771A6 (es) | 1989-02-01 |
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