GB1030138A - Phosphate products suitable for preparation of fire resistant polyurethane foams - Google Patents
Phosphate products suitable for preparation of fire resistant polyurethane foamsInfo
- Publication number
- GB1030138A GB1030138A GB4444763A GB4444763A GB1030138A GB 1030138 A GB1030138 A GB 1030138A GB 4444763 A GB4444763 A GB 4444763A GB 4444763 A GB4444763 A GB 4444763A GB 1030138 A GB1030138 A GB 1030138A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphate
- hydroxyl groups
- polyol
- acid
- epoxides
- 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
- 229910019142 PO4 Inorganic materials 0.000 title abstract 12
- 239000010452 phosphate Substances 0.000 title abstract 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 title abstract 10
- 229920005830 Polyurethane Foam Polymers 0.000 title abstract 4
- 239000011496 polyurethane foam Substances 0.000 title abstract 4
- 230000009970 fire resistant effect Effects 0.000 title abstract 3
- 238000002360 preparation method Methods 0.000 title abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 13
- 229920005862 polyol Polymers 0.000 abstract 13
- 150000003077 polyols Chemical class 0.000 abstract 13
- 239000000047 product Substances 0.000 abstract 8
- 239000007795 chemical reaction product Substances 0.000 abstract 7
- 239000000203 mixture Substances 0.000 abstract 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 6
- 150000002924 oxiranes Chemical class 0.000 abstract 6
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 abstract 6
- 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 5
- 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 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 5
- 239000000600 sorbitol Substances 0.000 abstract 5
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 abstract 4
- 229930195725 Mannitol Natural products 0.000 abstract 4
- 239000000594 mannitol Substances 0.000 abstract 4
- 235000010355 mannitol Nutrition 0.000 abstract 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 150000001735 carboxylic acids Chemical class 0.000 abstract 3
- 125000005442 diisocyanate group Chemical group 0.000 abstract 3
- 235000011187 glycerol Nutrition 0.000 abstract 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 3
- 229920000570 polyether Polymers 0.000 abstract 3
- 239000004604 Blowing Agent Substances 0.000 abstract 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- 150000001279 adipic acids Chemical class 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 238000004132 cross linking Methods 0.000 abstract 2
- 239000006260 foam Substances 0.000 abstract 2
- 150000002689 maleic acids Chemical class 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 229910000000 metal hydroxide Inorganic materials 0.000 abstract 2
- 150000004692 metal hydroxides Chemical class 0.000 abstract 2
- -1 phosphate ester Chemical class 0.000 abstract 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 abstract 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 2
- 150000003022 phthalic acids Chemical class 0.000 abstract 2
- 229920000728 polyester Polymers 0.000 abstract 2
- 238000003918 potentiometric titration Methods 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- BYEFHDZWRALTEN-UHFFFAOYSA-N 4-ethyl-2,6,7-trioxa-1$l^{5}-phosphabicyclo[2.2.2]octane 1-oxide Chemical compound C1OP2(=O)OCC1(CC)CO2 BYEFHDZWRALTEN-UHFFFAOYSA-N 0.000 abstract 1
- XYZZKVRWGOWVGO-UHFFFAOYSA-N Glycerol-phosphate Chemical compound OP(O)(O)=O.OCC(O)CO XYZZKVRWGOWVGO-UHFFFAOYSA-N 0.000 abstract 1
- 239000004721 Polyphenylene oxide Substances 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- OHRVBDRGLIWLPA-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] dihydrogen phosphate Chemical compound OCC(CO)(CO)COP(O)(O)=O OHRVBDRGLIWLPA-UHFFFAOYSA-N 0.000 abstract 1
- 239000000159 acid neutralizing agent Substances 0.000 abstract 1
- 235000011037 adipic acid Nutrition 0.000 abstract 1
- 239000001361 adipic acid Substances 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 238000005187 foaming Methods 0.000 abstract 1
- 239000004088 foaming agent Substances 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 239000011976 maleic acid Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 239000011343 solid material Substances 0.000 abstract 1
- 239000008247 solid mixture Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
- C08G18/6461—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63 having phosphorus
-
- 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
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
-
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3878—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus
- C08G18/3882—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus having phosphorus bound to oxygen only
- C08G18/3885—Phosphate compounds
-
- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/46—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen
- C08G18/4684—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing phosphorus
-
- 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
-
- 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)
- 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)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention comprises a product useful in the preparation of fire-resistant polyurethane foams having the residue of a polyol containing from 3 to 7 carbon atoms and 3 to 7 hydroxyl groups in chemical combination with phosphate groups, the phosphate content of the product being from 33-80 mole per cent of which 55-98% is present as the dibasic phosphate and the remainder as the monobasic phosphate, as determined by potentiometric titration; the product having an acid number of from 200-800 and a hydroxyl number of from 200-1200. The term "polyol" is meant to include polyethers and polyesters which contain free hydroxyl groups as well as alcohols in which the hydroxyl groups are neither etherified or esterified. The product is prepared by reacting a polyol having from three to seven carbon atoms and from three to seven hydroxyl groups with phosphorus pentoxide. The solid materials are fused together in a mole ratio of phosphorus pentoxide to polyol of between 0.25:1-2:1. It is preferred to carry out the process by adding a solid mixture of the phosphorus pentoxide and polyol to a molten portion of the polyol. The acid functions of the product must be neutralized prior to foaming by reacting with materials such as epoxides, amines and metal hydroxides. Then these products may be further reacted with epoxides or with a carboxylic acid and then with an organic diisocyanate in the presence of a blowing agent and a cross-linking catalyst to form a foam (see Division C3). Polyols which may be used as starting materials include sorbitol, mannitol, pentaerythritol, trimethylol propane, glycerine, a -methyl glucoside and mixtures of these: polyols having esterified hydroxyl groups include reaction products of the foregoing list with carboxylic acids such as maleic, adipic and phthalic acids; and polyols having etherified hydroxyl groups include reaction products of the foregoing list of unsubstituted polyols with epoxides such as propylene oxide, ethylene oxide and butylene oxide. Examples are given for the production of phosphate ester mixtures from sorbitol, pentaerythritol, mannitol, trimethylol propane, glycerine, a -methyl glucoside and a reaction product of sorbitol and propylene oxide and for the oxypropylation of the products by treatment with propylene oxide.ALSO:A fire-resistant polyurethane foam comprises the reaction product of (a) an organic diisocyanate, (b) a foaming agent and (c) the neutral reaction product of an acid neutralizing agent with a composition which comprises the residue of a polyol containing from 3 to 7 carbon atoms and 3 to 7 hydroxyl groups in chemical combination with phosphate groups, the phosphate content of the composition being from 33-80 mole per cent of which 55-98% is present as the dibasic phosphate and the remainder as mono-basic phosphate, as determined by potentiometric titration; the composition having an acid number of from 200-800 and a hydroxyl number of from 200-1200 (see Division C2). The term "polyol" is defined as including polyethers and polyesters which contain free hydroxyl groups as well as alcohols in which the hydroxyl groups are neither etherified nor esterified. Suitable polyols include sorbitol, mannitol, pentaerythritol, trimethylol propane, glycerine, a -methyl glucoside and mixtures of these; those having esterified hydroxy groups such as the reaction products of the foregoing list with such carboxylic acids as maleic, adipic and phthalic acids; and those having etherified hydroxy groups such as the reaction products of the foregoing list with epoxides such as propylene oxide, ethylene oxide and butylene oxide. The compositions of the invention may be neutralized by treatment with e.g. epoxides, amines and metal hydroxides. These products may then be further reacted with epoxides such as propylene oxide, ethylene oxide and butylene oxide, or carboxylic acids such as adipic acid, maleic acid and phthalic acid, and they are then reacted with an organic diisocyanate in the presence of a blowing agent and a cross-linking catalyst to form a foam. Examples are given for the production of polyurethane foams from toluene diisocyanate and oxypropylated derivatives of sorbitol phosphate, trimethylol propane phosphate, a -methyl glucoside phosphate, mannitol phosphate, glycerine phosphate, pentaerythritol phosphate and sorbitol polyether phosphate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23887562A | 1962-11-19 | 1962-11-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1030138A true GB1030138A (en) | 1966-05-18 |
Family
ID=22899688
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4444763A Expired GB1030138A (en) | 1962-11-19 | 1963-11-11 | Phosphate products suitable for preparation of fire resistant polyurethane foams |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE640049A (en) |
| DE (1) | DE1468293A1 (en) |
| GB (1) | GB1030138A (en) |
| NL (1) | NL300692A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111004379A (en) * | 2019-12-02 | 2020-04-14 | 浙江理工大学桐乡研究院有限公司 | Preparation method of flame-retardant polyol with high phosphorus content and multiple functionality degrees |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018046586A1 (en) * | 2016-09-09 | 2018-03-15 | Covestro Deutschland Ag | Porous materials based on polyurethane/polyisocyanurate and production and use thereof |
-
0
- BE BE640049D patent/BE640049A/xx unknown
- NL NL300692D patent/NL300692A/xx unknown
-
1963
- 1963-11-11 GB GB4444763A patent/GB1030138A/en not_active Expired
- 1963-11-18 DE DE19631468293 patent/DE1468293A1/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111004379A (en) * | 2019-12-02 | 2020-04-14 | 浙江理工大学桐乡研究院有限公司 | Preparation method of flame-retardant polyol with high phosphorus content and multiple functionality degrees |
Also Published As
| Publication number | Publication date |
|---|---|
| BE640049A (en) | |
| DE1468293A1 (en) | 1968-12-19 |
| NL300692A (en) |
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