GB1029465A - Phosphorus containing polyether polyols - Google Patents
Phosphorus containing polyether polyolsInfo
- Publication number
- GB1029465A GB1029465A GB2747364A GB2747364A GB1029465A GB 1029465 A GB1029465 A GB 1029465A GB 2747364 A GB2747364 A GB 2747364A GB 2747364 A GB2747364 A GB 2747364A GB 1029465 A GB1029465 A GB 1029465A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amount
- polyol
- oxide
- phosphorus
- h3po4
- 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
- 150000003077 polyols Chemical class 0.000 title abstract 12
- 229920005862 polyol Polymers 0.000 title abstract 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title abstract 5
- 239000004721 Polyphenylene oxide Substances 0.000 title abstract 5
- 229910052698 phosphorus Inorganic materials 0.000 title abstract 5
- 239000011574 phosphorus Substances 0.000 title abstract 5
- 229920000570 polyether Polymers 0.000 title abstract 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 6
- 125000002947 alkylene group Chemical group 0.000 abstract 6
- 239000007795 chemical reaction product Substances 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 4
- 235000011007 phosphoric acid Nutrition 0.000 abstract 4
- 229920005830 Polyurethane Foam Polymers 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 229920001228 polyisocyanate Polymers 0.000 abstract 3
- 239000005056 polyisocyanate Substances 0.000 abstract 3
- 239000004814 polyurethane Substances 0.000 abstract 3
- 229920002635 polyurethane Polymers 0.000 abstract 3
- 239000011496 polyurethane foam Substances 0.000 abstract 3
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 abstract 2
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 abstract 2
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 abstract 2
- 239000004604 Blowing Agent Substances 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 abstract 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 abstract 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 abstract 2
- 229930006000 Sucrose Natural products 0.000 abstract 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 abstract 2
- 150000001720 carbohydrates Chemical class 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000008121 dextrose Substances 0.000 abstract 2
- 230000032050 esterification Effects 0.000 abstract 2
- 238000005886 esterification reaction Methods 0.000 abstract 2
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N ethyl trimethyl methane Natural products CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 abstract 2
- 229920000137 polyphosphoric acid Polymers 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- 239000000600 sorbitol Substances 0.000 abstract 2
- 239000005720 sucrose Substances 0.000 abstract 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 abstract 2
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical class O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 abstract 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- OCHSQTXMLDMRGK-UHFFFAOYSA-N 1,5-dichloro-2,4-diisocyanatobenzene Chemical class ClC1=CC(Cl)=C(N=C=O)C=C1N=C=O OCHSQTXMLDMRGK-UHFFFAOYSA-N 0.000 abstract 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 1
- -1 pentaethritol Chemical compound 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 abstract 1
- 229940029284 trichlorofluoromethane Drugs 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H11/00—Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
- C07H11/04—Phosphates; Phosphites; Polyphosphates
-
- 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
-
- 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
- C07F9/098—Esters of polyphosphoric acids or anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- C07H15/08—Polyoxyalkylene derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5075—Polyethers having heteroatoms other than oxygen having phosphorus
- C08G18/5081—Polyethers having heteroatoms other than oxygen having phosphorus having phosphorus bound to oxygen only
- C08G18/5084—Phosphate compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
A phosphorus-containing polyether polyol comprises the reaction product of (a) the product formed by the esterification of (1) polyphosphoric acid containing 3 to 13% P2O5 in excess of the amount which provides 100% H3PO4 with (2) a polyol which is a polyhydroxyalkane containing from 3 to 6 hydroxyl groups, a carbohydrate containing from 5 to 8 hydroxyl groups or a mixture thereof, the polyol moiety being present in an amount of from 2 to 4 moles for each mole of P2O5 in excess of the amount which provides 100% H3PO4 and (b) an alkylene oxide containing from 2 to 4 carbon atoms, the alkylene oxide being present in an amount sufficient to neutralize all phosphoric acid groups, but less than the amount which lowers the hydroxyl number of the reaction product below 200. Suitable polyols are glycerol, trimethylolethane, trimethylolpropane, 1,2,6-hexanetriol, pentaerythritol, sorbitol, sucrose or dextrose and suitable alkylene oxides are 1,2-propylene oxide, epichlorohydrin and 1,2-butene oxide. A preferred class of polyisocyanates are chlorinated aromatic diisocyanates which contain at least 25% chlorine especially chlorinated m-phenylene diisocyanates, a 39% chlorine containing blend of which may be obtained by blending equal amounts of tetrachloro-, trichloro-, and dichloro-m-phenylene diisocyanates. The polyurethanes are generally prepared by forming a prepolymer containing free isocyanate groups which are then reacted with additional polyol. Examples are given for the production of polyurethane foams using trichlorofluoromethane and blowing agent. Water and other fluorinated hydrocarbons may also be used as blowing agents.ALSO:Polyurethanes and polyurethane foams may be prepared by reacting an aromatic polyisocyanate with a phosphorus-containing polyether polyol comprising the reaction product of (a) the product formed by the esterification of (1) polyphosphoric acid containing 3 to 13% P2O5 in excess of the amount which provides 100% H3PO4 with (2) a polyol which is a poly-hydroxyalkane containing from 3 to 6 hydroxyl groups, a carbohydrate containing from 5 to 8 hydroxyl groups or a mixture thereof, the polyol moiety being present in an amount of from 2 to 4 moles for each mole of P2O5 in excess of the amount which provides 100% H3PO4 and (b) an alkylene oxide containing from 2 to 4 carbon atoms, the alkylene oxide being present in an amount sufficient to neutralize all phosphoric acid groups, but less than the amount which lowers the hydroxy number of the reaction product below 200. Suitable polyols are glycerol, trimethylolethane, trimethylpropane, 1,2,6-hexanetriol, pentaethritol, sorbitol, sucrose or dextrose and suitable alkylene oxides are ethylene oxide, ethylene oxide, 1,2-propylene oxide, epichlorohydrin and 1,2-butene oxide. In the examples, a solvent such as dioxane or a previously prepared phosphorus containing polyether polyol is used. The phosphorus-containing polyether polyols may be reacted with polyisocyanates and impart flame-proofing properties to the polyurethanes and polyurethane foams thereby produced (see Division C3).
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US232594A US3251828A (en) | 1962-10-23 | 1962-10-23 | Polyphosphoric acid esters of polyether polyols |
| GB2747364A GB1029465A (en) | 1964-07-03 | 1964-07-03 | Phosphorus containing polyether polyols |
| FR982832A FR1410280A (en) | 1964-07-03 | 1964-07-23 | Inflammation-retardant compositions based on polyether polyols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2747364A GB1029465A (en) | 1964-07-03 | 1964-07-03 | Phosphorus containing polyether polyols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1029465A true GB1029465A (en) | 1966-05-11 |
Family
ID=10260165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2747364A Expired GB1029465A (en) | 1962-10-23 | 1964-07-03 | Phosphorus containing polyether polyols |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1029465A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2385586A1 (en) * | 2010-12-29 | 2012-07-27 | Universidad Castilla-La Mancha | Polyol phosphate and process of obtaining (Machine-translation by Google Translate, not legally binding) |
| CN104829825A (en) * | 2015-05-26 | 2015-08-12 | 济南大学 | Preparation method and application of phosphorus cycle flame-retardant polyhydric alcohols |
| CN104829823A (en) * | 2015-05-26 | 2015-08-12 | 济南大学 | Preparation method and application of flame-retardant polyol |
-
1964
- 1964-07-03 GB GB2747364A patent/GB1029465A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2385586A1 (en) * | 2010-12-29 | 2012-07-27 | Universidad Castilla-La Mancha | Polyol phosphate and process of obtaining (Machine-translation by Google Translate, not legally binding) |
| CN104829825A (en) * | 2015-05-26 | 2015-08-12 | 济南大学 | Preparation method and application of phosphorus cycle flame-retardant polyhydric alcohols |
| CN104829823A (en) * | 2015-05-26 | 2015-08-12 | 济南大学 | Preparation method and application of flame-retardant polyol |
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