GB1059506A - Improvements in or relating to phosphorus-containing polyether polyols - Google Patents
Improvements in or relating to phosphorus-containing polyether polyolsInfo
- Publication number
- GB1059506A GB1059506A GB248465A GB248465A GB1059506A GB 1059506 A GB1059506 A GB 1059506A GB 248465 A GB248465 A GB 248465A GB 248465 A GB248465 A GB 248465A GB 1059506 A GB1059506 A GB 1059506A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxide
- phosphorus
- epoxypropyl
- monoepoxide
- phosphonate
- 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
- 229910052698 phosphorus Inorganic materials 0.000 title abstract 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title abstract 5
- 239000011574 phosphorus Substances 0.000 title abstract 5
- 229920005862 polyol Polymers 0.000 title abstract 3
- 150000003077 polyols Chemical class 0.000 title abstract 3
- 239000004721 Polyphenylene oxide Substances 0.000 title abstract 2
- 229920000570 polyether Polymers 0.000 title abstract 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 3
- 239000002667 nucleating agent Substances 0.000 abstract 3
- 150000002924 oxiranes Chemical class 0.000 abstract 2
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 abstract 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 abstract 1
- FUKXIMRHLZJUCG-UHFFFAOYSA-N 2-(diethoxyphosphorylmethyl)oxirane Chemical compound CCOP(=O)(OCC)CC1CO1 FUKXIMRHLZJUCG-UHFFFAOYSA-N 0.000 abstract 1
- JFDMLXYWGLECEY-UHFFFAOYSA-N 2-benzyloxirane Chemical compound C=1C=CC=CC=1CC1CO1 JFDMLXYWGLECEY-UHFFFAOYSA-N 0.000 abstract 1
- NPRYHWFMGPYJIY-UHFFFAOYSA-N 2-cyclohexyloxirane Chemical compound C1OC1C1CCCCC1 NPRYHWFMGPYJIY-UHFFFAOYSA-N 0.000 abstract 1
- CXURGFRDGROIKG-UHFFFAOYSA-N 3,3-bis(chloromethyl)oxetane Chemical compound ClCC1(CCl)COC1 CXURGFRDGROIKG-UHFFFAOYSA-N 0.000 abstract 1
- 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 1
- 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 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 abstract 1
- 229930091371 Fructose Natural products 0.000 abstract 1
- 239000005715 Fructose Substances 0.000 abstract 1
- 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 1
- 239000002841 Lewis acid Substances 0.000 abstract 1
- UAWLVELGGDMAIZ-UHFFFAOYSA-N OP(OCC1OC1(C1CCCCC1)C1CCCCC1)=O Chemical compound OP(OCC1OC1(C1CCCCC1)C1CCCCC1)=O UAWLVELGGDMAIZ-UHFFFAOYSA-N 0.000 abstract 1
- 229920005830 Polyurethane Foam Polymers 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
- 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 1
- 229930006000 Sucrose Natural products 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 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 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- YCZMMGTVEHSOTN-UHFFFAOYSA-N cyclododecane-1,5,9-triol Chemical compound OC1CCCC(O)CCCC(O)CCC1 YCZMMGTVEHSOTN-UHFFFAOYSA-N 0.000 abstract 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 abstract 1
- -1 ethyl 2,3-epoxypropyl ethylphosphinate Chemical compound 0.000 abstract 1
- 239000003063 flame retardant Substances 0.000 abstract 1
- 239000008103 glucose Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 abstract 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 125000004437 phosphorous atom Chemical group 0.000 abstract 1
- 239000011496 polyurethane foam Substances 0.000 abstract 1
- 239000000600 sorbitol Substances 0.000 abstract 1
- 239000005720 sucrose Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 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
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- 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
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
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)
- Polyethers (AREA)
Abstract
Phosphorus-containing polyether polyols are prepared by reacting a monoepoxide which contains a vic-epoxy-alkyl radical directly attached to a phosphorus atom with a compound containing three or more hydroxy groups (nucleating agent). A mixture of the above epoxide with a monoepoxide which does not contain phosphorus may be reacted with the nucleating agent. Catalysts may be used in the reaction, e.g. tertiary amines, Lewis acids, or alkali metal hydroxides. The polyols are useful in the preparation of flame-retardant polyurethane foams. Examples of nucleating agents are glycerol, pentaerythritol, sorbitol, 1,5,9-trihydroxy cyclododecane, glucose, fructose, or sucrose. Typical monoepoxides containing phosphorus are ethyl 2,3-epoxypropyl ethylphosphinate, diphenyl - 9,10 - epoxyoctadecyl-phosphine oxide, dicyclohexyl-2,3-epoxypropyl phosphonate, and diethyl - 2,3 - epoxypropyl -phosphonate. Monoepoxides that do not contain phosphorus are oxiranes, e.g. ethylene oxide, propylene oxide, epichloro-and epibromohydrin, 1-butene oxide, cyclohexylethylene oxide, styrene oxide, and benzylethylene oxide, and oxetans, e.g. trimethylene oxide and 3,3-di (chloromethyl) oxetan.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB248565A GB1059507A (en) | 1965-01-20 | 1965-01-20 | Improvements in or relating to polyurethanes |
| GB248465A GB1059506A (en) | 1965-01-20 | 1965-01-20 | Improvements in or relating to phosphorus-containing polyether polyols |
| FR46259A FR1464430A (en) | 1965-01-20 | 1966-01-18 | Improvements with polyether polyols and polyurethanes derived from these polyether polyols |
| BE675309D BE675309A (en) | 1965-01-20 | 1966-01-19 | |
| NL6600681A NL6600681A (en) | 1965-01-20 | 1966-01-19 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB248565A GB1059507A (en) | 1965-01-20 | 1965-01-20 | Improvements in or relating to polyurethanes |
| GB248465A GB1059506A (en) | 1965-01-20 | 1965-01-20 | Improvements in or relating to phosphorus-containing polyether polyols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1059506A true GB1059506A (en) | 1967-02-22 |
Family
ID=26237544
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB248565A Expired GB1059507A (en) | 1965-01-20 | 1965-01-20 | Improvements in or relating to polyurethanes |
| GB248465A Expired GB1059506A (en) | 1965-01-20 | 1965-01-20 | Improvements in or relating to phosphorus-containing polyether polyols |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB248565A Expired GB1059507A (en) | 1965-01-20 | 1965-01-20 | Improvements in or relating to polyurethanes |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE675309A (en) |
| FR (1) | FR1464430A (en) |
| GB (2) | GB1059507A (en) |
| NL (1) | NL6600681A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005118678A1 (en) * | 2004-06-03 | 2005-12-15 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of polyether polyols |
| 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) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8974591B2 (en) | 2010-03-16 | 2015-03-10 | Fpinnovations | Heat-resistant structural wood adhesive compositions involving pMDI, polyol and aromatic polyols |
| HUE051636T2 (en) * | 2013-04-16 | 2021-03-01 | Basf Se | Phosphorous containing flame retardants |
-
1965
- 1965-01-20 GB GB248565A patent/GB1059507A/en not_active Expired
- 1965-01-20 GB GB248465A patent/GB1059506A/en not_active Expired
-
1966
- 1966-01-18 FR FR46259A patent/FR1464430A/en not_active Expired
- 1966-01-19 NL NL6600681A patent/NL6600681A/xx unknown
- 1966-01-19 BE BE675309D patent/BE675309A/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005118678A1 (en) * | 2004-06-03 | 2005-12-15 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of polyether polyols |
| US7300993B2 (en) | 2004-06-03 | 2007-11-27 | Shell Oil Company | Process for the preparation of polyether polyols |
| CN100509914C (en) * | 2004-06-03 | 2009-07-08 | 国际壳牌研究有限公司 | Process for the preparation of polyether polyols |
| 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) |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6600681A (en) | 1966-07-21 |
| BE675309A (en) | 1966-07-19 |
| FR1464430A (en) | 1966-12-30 |
| GB1059507A (en) | 1967-02-22 |
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