GB1042622A - Phosphate polyisocyanate compositions and fire resistant products made therefrom - Google Patents
Phosphate polyisocyanate compositions and fire resistant products made therefromInfo
- Publication number
- GB1042622A GB1042622A GB1298763A GB1298763A GB1042622A GB 1042622 A GB1042622 A GB 1042622A GB 1298763 A GB1298763 A GB 1298763A GB 1298763 A GB1298763 A GB 1298763A GB 1042622 A GB1042622 A GB 1042622A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxide
- reacted
- propylene oxide
- h3po4
- propylene
- 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
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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/776—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur 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
- C08G18/30—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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
An ester of orthophosphosphoric acid or polyphosphoric acid having two or more functional groups with reactive hydrogen atoms is reacted with an organic polyisocyanate. The orthophosphoric acid is defined as having a strength of up to and including 100% H3PO4 and the polyphosphoric acid as having an acid strength of more than 100% H3PO4. The esters may be prepared by (1) reaction of one of the above acids with a monomeric cyclic compound containing a three-membered heterocyclic ring in which the hetero atom is O, N or S which may be followed by chain extension and neutralization or (2) reaction of P2O5 with a polyol, polyamine or polymercaptan which may be followed by chain extension and neutralization. Monomeric cyclic compounds may be: ethylene oxide, propylene oxide; 1,2-butylene oxide, pentylene oxide, octylene oxide, octadecylene oxide, styrene oxide, phenyl glycidyl ether, butyl glycidyl ether, allyl glycidyl ether, ethylene sulphide, propylene sulphide; 1,2-butylene sulphide; 2,3-butylene sulphide; styrene sulphide, allyl thioglycidyl ether; ethylene imine; propylene imine; epichlorhydrin, epibromohydrin, and glycidol. Polyols, polymercaptans and polyamines may be: sorbitol, trimethylolpropane, pentaerythritol, propylene glycol, polypropylene glycol, ethylene glycol, polyethylene glycol, 1,2-hydroxy butane; 2,3-hydroxybutane, polybutylene glycol; bis-b -dimercaptoethyl ether and N,N,N1,N1 - tetrakis(2 - hydroxypropyl)ethylene diamine. In Example (1) phosphoric acid is reacted with either propylene oxide or epichlorhydrin in molar ratios of monomer: acid of 5:1 to 10:1, or with polypropylene glycol (3:3:1). In Example (2) P2O5 is reacted with propylene oxide and chain extended in a second step with more propylene oxide. In Example (5) propylene oxide is reacted with a pentaerythritol/H3PO4 adduct. In Examples (6) epichlorhydrin and propylene oxide are reacted with H3PO4. (7) Propylene oxide and trimethylol propane are reacted with H3PO4. (13) Propylene oxide is reacted with the adduct of H3PO4 and sorbitol. (14) Propylene oxide and a polyepoxide ("EPON" 828) are reacted with H3PO4. In Example (23) the esters prepared as described above are reacted with an excess of tolylene diisocyanate to given an adduct containing free-NCO groups.ALSO:Polymers, e.g. polyurethanes or polyureas are produced by reacting an organic polyisocyanate with an ester (see Division C2) of orthophosphoric acid or polyphosphoric acid, said ester having two or more functional groups with reactive hydrogen terminals, e.g. hydroxyl, mercapto or amino groups. The orthophosphoric acid is defined as having a strength of up to and including 100% H3PO4 and the polyphosphoric acid as having an acid strength of more than 100% H3PO4. The esters may be prepared by the (1) reaction of one of the above acids with a monomeric cyclic compound containing a three-membered heterocyclic ring in which the hetero atom is O, N or S which may be followed by chain extension and neutralization, or (2) by reaction of P2P5 with a polyol, polymercaptan or polyamine which may be followed by chain extension and neutralization. Monomeric cyclic compounds may be: ethylene oxide, propylene oxide; 1,2-butylene oxide, pentylene oxide, octylene oxide, octadecylene oxide, styrene oxide, phenyl glycidyl ether, butyl glycidyl ether, allyl glycidyl ether, ethylene sulphide, propylene sulphide; 1,2-butylene sulphide; 2,3-butylene sulphide; styrene sulphide, allyl thioglycidyl ether; ethylene imine; propylene imine, epichlorhydrin, epibromohydrin and glycirol. Polyols, polymercaptans and polyamines may be: sorbitol, trimethylolpropane, pentaerythritol, propylene glycol, polypropylene glycol, ethylene glycol, polyethylene glycol; 1,2-hydroxybutane; 2,3-hydroxybutane, polybutylene glycol; bis-b -dimercaptoethyl ether and N,N,N1,N1-tetrakis-(2-hydroxypropyl) ethylene diamine. The phosphoric acid may also be esterified with polyepoxy materials, e.g. epoxidized polybutadiene materials, bisphenol A/epichlor hydrin type, cycloaliphatic type, resorcinol diglycidyl ether type, epoxynovolate type and epoxidized fatty acids. In Example (23) an excess of tolylene diisocyanate is reacted with various esters and orthochlorobenzoyl chloride added to the reaction mixture to obtain a prepolymer. Typical esters used are the reaction products of phosphoric acid with (1) propylene oxide, (2) epichlorhydrin, (3) polypropylene glycol, (4) pentaerythritol followed by propylene oxide, (5) propylene oxide and epichlorhydrin, (6) butylene oxide, (7) sorbitol and propylene oxide, (8) propylene oxide and a polyepoxide ("EPON" 828), (9) trimethylol propane, (10) Styrene oxide, (11) dipropylene glycol. In Example (24) self-extinguishing foams were prepared from the prepolymers obtained as described above by reaction with N,N,N1,N1 tetrakis - (2 - hydroxypropyl) ethylene diamine and a phosphate ester in the presence of diethylethanolamine, triethylene diamine water and silicone surfactant. In Example (26) esters prepared as described above were reacted with a deficiency of diisocyanate to form hydroxy functional adducts which were converted to foams by reaction with prepolymers. In Example (30) a casting was prepared from tolylene diisocyanate and the reaction product of propylene oxide and H3PO4. In Example (31) a prepolymer derived from tolylene diisocyanate and the adduct of epichlorhydrin and H3PO4 was reacted with more of the same adduct to prepare a laminating resin, which was used to coat pieces of cloth.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US18457762A | 1962-04-02 | 1962-04-02 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1042622A true GB1042622A (en) | 1966-09-14 |
Family
ID=22677481
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1298763A Expired GB1042622A (en) | 1962-04-02 | 1963-04-02 | Phosphate polyisocyanate compositions and fire resistant products made therefrom |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB1042622A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0856551A1 (en) * | 1997-01-30 | 1998-08-05 | Air Products And Chemicals, Inc. | Polyphosphoric acid as a stabilizer for polyurethane prepolymers |
US20220267503A1 (en) * | 2017-03-02 | 2022-08-25 | Covestro Deutschland Ag | Reaction mixtures of isocyanates and polyols with extended pot life |
-
1963
- 1963-04-02 GB GB1298763A patent/GB1042622A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0856551A1 (en) * | 1997-01-30 | 1998-08-05 | Air Products And Chemicals, Inc. | Polyphosphoric acid as a stabilizer for polyurethane prepolymers |
US20220267503A1 (en) * | 2017-03-02 | 2022-08-25 | Covestro Deutschland Ag | Reaction mixtures of isocyanates and polyols with extended pot life |
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