GB1073564A - Polyethers containing phosphorus and alcoholic hydroxy groups and their production - Google Patents
Polyethers containing phosphorus and alcoholic hydroxy groups and their productionInfo
- Publication number
- GB1073564A GB1073564A GB5284865A GB5284865A GB1073564A GB 1073564 A GB1073564 A GB 1073564A GB 5284865 A GB5284865 A GB 5284865A GB 5284865 A GB5284865 A GB 5284865A GB 1073564 A GB1073564 A GB 1073564A
- Authority
- GB
- United Kingdom
- Prior art keywords
- epoxy compound
- phosphorus
- reacted
- phosphinic acid
- production
- 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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title abstract 3
- 229910052698 phosphorus Inorganic materials 0.000 title abstract 3
- 239000011574 phosphorus Substances 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 230000001476 alcoholic effect Effects 0.000 title 1
- 229920000570 polyether Polymers 0.000 title 1
- 239000004593 Epoxy Substances 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 abstract 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 abstract 3
- 239000000047 product Substances 0.000 abstract 3
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 abstract 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 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
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- -1 aliphatic aldehyde Chemical class 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 1
- 229920002866 paraformaldehyde Polymers 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C08G18/48—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)]
-
- 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)]
- C07F9/301—Acyclic saturated 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fireproofing Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention comprises a process for the production of hydroxy-containing ether derivatives of bis (hydroxyalkyl) phosphinic acid in which (i) white phosphorus is reacted with an alkali metal hydroxide, water, and an aliphatic aldehyde in the presence of a liquid saturated aliphatic alcohol; (ii) the more volatile components are distilled off; and (iii) the product, primarily a salt of bis (hydroxyalkyl) phosphinic acid, is reacted with at least one epoxy compound at 50 DEG to 160 DEG C., the quantity of the epoxy compound being such as to provide at least 3 mol. per g-atom of phosphorus in the phosphinic acid. The invention also comprises the product prepared according to step (iii) of the process above using epichloro- or epibromo-hydrin, styrene, propylene or ethylene oxide, or glycidol, as the epoxy compound, and having an hydroxyl number of 60 to 400 and an acid number of 2 to 6, and containing 3 to 12% of phosphorus. When an epoxy compound other than epichlorohydrin is used, the resulting product may be subsequently reacted with epichlorohydrin. Suitable epoxy compounds are those listed above, while suitable aldehydes are e.g. formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, and their low molecular weight polymers or condensation products e.g. paraformaldehyde, trioxan, and aldol.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC34742A DE1232578B (en) | 1964-12-24 | 1964-12-24 | Process for the preparation of alcoholic hydroxyl groups and phosphorus containing polyethers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1073564A true GB1073564A (en) | 1967-06-28 |
Family
ID=7021472
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5284865A Expired GB1073564A (en) | 1964-12-24 | 1965-12-13 | Polyethers containing phosphorus and alcoholic hydroxy groups and their production |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1232578B (en) |
| FR (1) | FR1461298A (en) |
| GB (1) | GB1073564A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2190812A1 (en) * | 1972-06-27 | 1974-02-01 | Dow Chemical Co | Halogenated epoxides - plasticizers for pvc and fire retardants for polyesters |
-
1964
- 1964-12-24 DE DEC34742A patent/DE1232578B/en active Pending
-
1965
- 1965-12-13 GB GB5284865A patent/GB1073564A/en not_active Expired
- 1965-12-24 FR FR43661A patent/FR1461298A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1232578B (en) | 1967-01-19 |
| FR1461298A (en) | 1966-12-10 |
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