GB1083939A - Production of self-extinguishing polyurethanes - Google Patents
Production of self-extinguishing polyurethanesInfo
- Publication number
- GB1083939A GB1083939A GB5468665A GB5468665A GB1083939A GB 1083939 A GB1083939 A GB 1083939A GB 5468665 A GB5468665 A GB 5468665A GB 5468665 A GB5468665 A GB 5468665A GB 1083939 A GB1083939 A GB 1083939A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bis
- prepared
- bromomethyl
- epichlorohydrin
- hydroxyalkyl
- 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
- 239000004814 polyurethane Substances 0.000 title abstract 2
- 229920002635 polyurethane Polymers 0.000 title abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- -1 phosphinic acid ester Chemical class 0.000 abstract 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- 239000011574 phosphorus Substances 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- CVMBZULCJCBJFZ-UHFFFAOYSA-N 3-bromo-2-(bromomethyl)-2-methylpropan-1-ol Chemical compound OCC(C)(CBr)CBr CVMBZULCJCBJFZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004604 Blowing Agent Substances 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 abstract 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000005997 bromomethyl group Chemical group 0.000 abstract 1
- 239000001273 butane Substances 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 239000012467 final product Substances 0.000 abstract 1
- OTGHWLKHGCENJV-UHFFFAOYSA-N glycidic acid Chemical compound OC(=O)C1CO1 OTGHWLKHGCENJV-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000000465 moulding Methods 0.000 abstract 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 abstract 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 1
- 229920005906 polyester polyol Polymers 0.000 abstract 1
- 239000005056 polyisocyanate Substances 0.000 abstract 1
- 229920001228 polyisocyanate Polymers 0.000 abstract 1
- 239000001294 propane Substances 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
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5075—Polyethers having heteroatoms other than oxygen having phosphorus
- C08G18/5078—Polyethers having heteroatoms other than oxygen having phosphorus having phosphorus bound to carbon and/or to hydrogen
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3211—Esters of acyclic saturated acids which can have 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
- 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
- C08G18/3802—Low-molecular-weight compounds having heteroatoms other than oxygen having halogens
- C08G18/3804—Polyhydroxy compounds
- C08G18/3806—Polyhydroxy compounds having chlorine and/or bromine atoms
- C08G18/381—Polyhydroxy compounds having chlorine and/or bromine atoms having bromine atoms
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
A self-extinguishing polyurethane product is prepared by curing a mixture of polyether-, or polyester-polyol, an organic polyisocyanate, a curing catalyst, sufficient of a saturated aliphatic ether containing a free OH group and a quaternary carbon atom carrying a bromomethyl group to give 0.1-25% by weight of bromine in the product, and sufficient aliphatic ether of a bis-(hydroxyalkyl) phosphinic acid ester containing free OH groups to give 0.1-6% by weight of phosphorus in the final product. The moulding mass may also include a blowing agent. Suitable bromine compounds can be prepared by reacting at least 1.2 mols. of a compound such as pentaerythritol-, mono-, dior tri-bromhydrin; 1,1-dimethylol-1-bromomethyl-, or 1-methylol-1,1-bis-(bromomethyl)-ethane, propane or butane; or the mono-, di- or tri-bromohydrin of 1,1,1-trimethylol isopropanol with 1 mol. of ethylene oxide; 1,2-propylene oxide; styrene oxide; epichlorohydrin; epibromhydrin; glycidol; or the methyl or ethyl ester of glycidic acid. Suitable phosphorus-containing compounds can be prepared by etherifying bis-(hydroxyalkyl) phosphinic acids, forming the alkali metal salts, and esterifying them by boiling with epichlorohydrin.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC0034741 | 1964-12-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1083939A true GB1083939A (en) | 1967-09-20 |
Family
ID=7021470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5468665A Expired GB1083939A (en) | 1964-12-24 | 1965-12-23 | Production of self-extinguishing polyurethanes |
Country Status (2)
| Country | Link |
|---|---|
| GB (1) | GB1083939A (en) |
| NL (1) | NL6516834A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3686358A (en) * | 1971-04-12 | 1972-08-22 | James L Bertram | Glycidyl ethers of haloneopentyl glycols |
| US10208187B2 (en) | 2017-07-24 | 2019-02-19 | Icl-Ip America Inc. | Reactive flame retardants for flexible polyurethane foams |
| US10597511B2 (en) | 2017-09-21 | 2020-03-24 | Icl-Ip America Inc. | Reactive flame retardant blends for flexible polyurethane foam |
| WO2020193087A1 (en) * | 2019-03-25 | 2020-10-01 | Huntsman International Llc | Polyether polyol |
-
1965
- 1965-12-23 GB GB5468665A patent/GB1083939A/en not_active Expired
- 1965-12-23 NL NL6516834A patent/NL6516834A/xx unknown
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3686358A (en) * | 1971-04-12 | 1972-08-22 | James L Bertram | Glycidyl ethers of haloneopentyl glycols |
| US10208187B2 (en) | 2017-07-24 | 2019-02-19 | Icl-Ip America Inc. | Reactive flame retardants for flexible polyurethane foams |
| US10899911B2 (en) | 2017-07-24 | 2021-01-26 | Icl-Ip America Inc. | Reactive flame retardants for flexible polyurethane foams |
| US11352479B2 (en) | 2017-07-24 | 2022-06-07 | Icl-Ip America Inc. | Rigid polyurethane foam containing reactive flame retardant |
| US10597511B2 (en) | 2017-09-21 | 2020-03-24 | Icl-Ip America Inc. | Reactive flame retardant blends for flexible polyurethane foam |
| WO2020193087A1 (en) * | 2019-03-25 | 2020-10-01 | Huntsman International Llc | Polyether polyol |
| CN113661198A (en) * | 2019-03-25 | 2021-11-16 | 亨茨曼国际有限公司 | Polyether polyols |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6516834A (en) | 1966-06-27 |
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