GB918868A - Polyurethane foams - Google Patents
Polyurethane foamsInfo
- Publication number
- GB918868A GB918868A GB2786660A GB2786660A GB918868A GB 918868 A GB918868 A GB 918868A GB 2786660 A GB2786660 A GB 2786660A GB 2786660 A GB2786660 A GB 2786660A GB 918868 A GB918868 A GB 918868A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphorus
- polyether
- reaction mixture
- acids
- hydroxyl
- 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
- 229920005830 Polyurethane Foam Polymers 0.000 title 1
- 239000011496 polyurethane foam Substances 0.000 title 1
- 239000004721 Polyphenylene oxide Substances 0.000 abstract 8
- 238000000034 method Methods 0.000 abstract 8
- 229920000728 polyester Polymers 0.000 abstract 8
- 229920000570 polyether Polymers 0.000 abstract 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 6
- 239000011541 reaction mixture Substances 0.000 abstract 6
- 229910052698 phosphorus Inorganic materials 0.000 abstract 5
- 239000011574 phosphorus Substances 0.000 abstract 5
- -1 phosphorus compound Chemical class 0.000 abstract 5
- 150000003018 phosphorus compounds Chemical class 0.000 abstract 5
- 229910019142 PO4 Inorganic materials 0.000 abstract 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 230000032050 esterification Effects 0.000 abstract 4
- 238000005886 esterification reaction Methods 0.000 abstract 4
- 150000002170 ethers Chemical class 0.000 abstract 4
- 239000006260 foam Substances 0.000 abstract 4
- 235000021317 phosphate Nutrition 0.000 abstract 4
- 229920001281 polyalkylene Polymers 0.000 abstract 4
- 229920001228 polyisocyanate Polymers 0.000 abstract 4
- 239000005056 polyisocyanate Substances 0.000 abstract 4
- 239000004814 polyurethane Substances 0.000 abstract 4
- 229920002635 polyurethane Polymers 0.000 abstract 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 abstract 4
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 abstract 2
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 abstract 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 abstract 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 abstract 2
- 239000005642 Oleic acid Substances 0.000 abstract 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 2
- 239000007983 Tris buffer Substances 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 235000011037 adipic acid Nutrition 0.000 abstract 2
- 150000001279 adipic acids Chemical class 0.000 abstract 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 2
- 230000001413 cellular effect Effects 0.000 abstract 2
- 239000007795 chemical reaction product Substances 0.000 abstract 2
- 239000008199 coating composition Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 abstract 2
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 abstract 2
- 238000005187 foaming Methods 0.000 abstract 2
- 150000005826 halohydrocarbons Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 2
- 239000010452 phosphate Substances 0.000 abstract 2
- 150000008301 phosphite esters Chemical class 0.000 abstract 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 abstract 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 2
- 150000003022 phthalic acids Chemical class 0.000 abstract 2
- 239000004033 plastic Substances 0.000 abstract 2
- 229920003023 plastic Polymers 0.000 abstract 2
- 229920001451 polypropylene glycol Polymers 0.000 abstract 2
- 229920001296 polysiloxane Polymers 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 239000008096 xylene Substances 0.000 abstract 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 abstract 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical class NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 abstract 1
- 150000003017 phosphorus Chemical class 0.000 abstract 1
- 229920006295 polythiol Polymers 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
- C08G18/5081—Polyethers having heteroatoms other than oxygen having phosphorus having phosphorus bound to oxygen only
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)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Abstract
A process for the production of polyurethane plastics comprises reacting an organic polyisocyanate and a phosphorus compound of the formula P[O(RO)nH]3 or O=P[O(RO)nH]3 or <FORM:0918868/IV(a)/1> wherein R is an alkylene radical and n is an integer between 2 and 35. The phosphorus compounds can be prepared by alkoxylation of phosphoric or phosphorus acids or esterification of the acids with polyhydric polyalkylene ethers. Hydroxyl-containing polyesters or polythioethers may be mixed with the polyalkylene ethers for esterification with the phosphorus compounds. Cellular products can be obtained by using the phosphates or phosphites as the active hydrogen-containing compounds in a process similar to that of Specification 769,680. Foaming can also be effected by including halohydrocarbons in the reaction mixture. The phosphorus compounds may be mixed with a hydroxyl group-containing polyester or polyether before conversion to the foam. Non-porous polyurethanes can be obtained by substituting the phosphate or phosphite esters for the hydroxyl polyesters in the process described in Specification 700,608. Tri(chlorethyl) phosphate can be included in the reaction mixture to impart flame resistance. Coating compositions are obtained by mixing the phosphorus-containing polyether with a polyisocyanate in a solvent such as diethylene glycol diethyl ether, benzene, toluene or xylene. In examples (1) propylene oxide is reacted with phosphoric acid and phosphorus pentoxide to give a polyether as an oil of OH number 400. This is converted to a foam by reaction with permethylated aminoethyl piperazine, water, a modified polysiloxane and toluylene diisocyanate; (3) a polyester from phthalic and adipic acids, oleic acid and trimethylol propane and (4) a trimethylol propane/propylene oxide reaction product is included in the reaction mixture in a similar process; (9) a tris(hydroxyalkylene polyether) phosphite from phosphorus trichloride and polypropylene glycol is similarly reacted. Specification 804,369 also is referred to.ALSO:A process for the production of polyurethane plastics comprises reacting an organic polyisocyanate and a phosphorus compound of the formula P[O (RO)nH]3 or O = P[O (RO)nH]3 or <FORM:0918868/V/1> wherein R is an alkylene radical and n is an integer between 2 and 35. The phosphorus compounds can be prepared by alkoxylation of phosphoric or phosphorous acids or esterification of the acids with polyhydric polyalkylene ethers. Hydroxyl-containing polyesters or polythio-ethers may be mixed with the polyalkylene ethers for esterification with the phosphorus compounds. Cellular products can be obtained by using the phosphates or phosphites as the active hydrogen-containing compounds in a process similar to that of Specification 769,680. Foaming can also be effected by including halohydro-carbons in the reaction mixture. The phosphorus compound may be mixed with a hydroxyl group-containing polyester or polyether before conversion of the foam. Non porous polyurethanes can be obtained by substituting the phosphate or phosphite esters for the hydroxyl polyesters in the process described in Specification 700,608. Tri (chlorethyl) phosphate can be included in the reaction mixture to impart flame resistance. Coating compositions are obtained by mixing the phosphorus containing polyether with a polyisocyanate in a solvent such as diethylene glycol diethyl ether, benzene, toluene or xylene. In examples (1) propylene oxide is reacted with phosphoric acid and phosphorus pentoxide to give a polyether as an oil of OH number 400. This is converted to a foam by reaction with permethylated aminoethyl piperzaine, water, a modified polysiloxane and toluylene diisocyanate; (3) a polyester from phthalic and adipic acids, oleic acid and trimethylol propane, and (4) a trimethylol propane/propylene oxide reaction product is included in the reaction mixture in a similar process; (9) a tris (hydroxy alkylene polyether) phosphite from phosphorus trichloride and polypropylene glycol is similarly reacted. Specification 804,369 also is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF29159A DE1106489B (en) | 1959-08-11 | 1959-08-11 | Process for the production of optionally foamed plastics containing phosphorus atoms and urethane groups |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB918868A true GB918868A (en) | 1963-02-20 |
Family
ID=7093188
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2786660A Expired GB918868A (en) | 1959-08-11 | 1960-08-11 | Polyurethane foams |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE593966A (en) |
| DE (1) | DE1106489B (en) |
| GB (1) | GB918868A (en) |
| NL (2) | NL254779A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4234693A (en) * | 1975-06-24 | 1980-11-18 | Imperial Chemical Industries Limited | Process for making polyurea foams utilizing imidazole catalysts |
| US6552159B1 (en) * | 1991-03-15 | 2003-04-22 | Dao-Ichi Kogyo Seiyaku Co., Ltd. | Cladding resin composition |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1094489A (en) * | 1959-04-20 | 1967-12-13 | Mobil Oil Corp | Urethane polymers and process for making same |
| NL258684A (en) | 1959-12-04 | |||
| DE1138219B (en) | 1960-04-12 | 1962-10-18 | Bayer Ag | Process for the production of non-combustible or hardly inflammable, optionally foamed plastics containing phosphorus atoms and urethane groups |
| DE1143021B (en) | 1961-03-29 | 1963-01-31 | Bayer Ag | Process for the production of flame-retardant plastics containing phosphorus atoms and urethane groups |
| US3142650A (en) * | 1961-05-15 | 1964-07-28 | Union Carbide Corp | Polyurethanes from tris-polypropylene glycol phosphites |
| NL279175A (en) * | 1961-06-01 | 1900-01-01 | ||
| DE1208885B (en) * | 1961-07-11 | 1966-01-13 | Hooker Chemical Corp | Process for the production of fire-resistant polyurethane foams containing phosphorus atoms |
| DE1236184B (en) * | 1961-08-07 | 1967-03-09 | Pure Chem Ltd | Process for the production of optionally foamed polyurethanes |
| NL282903A (en) * | 1961-09-05 | |||
| BE623822A (en) * | 1961-10-26 | |||
| GB1013461A (en) * | 1961-11-23 | 1965-12-15 | Albright & Wilson Mfg Ltd | Novel phosphonitrilic compounds and preparation of polyurethanes therefrom |
| US3278464A (en) * | 1961-12-08 | 1966-10-11 | Hooker Chemical Corp | Phosphonated polymers |
| NL295929A (en) * | 1962-07-30 | 1900-01-01 | ||
| US3218272A (en) * | 1962-09-05 | 1965-11-16 | Fmc Corp | Flame-retardant polyurethane foams |
| BE641196A (en) * | 1963-02-07 | 1900-01-01 | ||
| GB1027057A (en) * | 1963-07-29 | 1966-04-20 | Allied Chem | Improvements in and relating to the manufacture of rigid polyurethane foams |
| DE1206580B (en) * | 1964-02-15 | 1965-12-09 | Bayer Ag | Process for the production of flame-retardant foams containing urethane groups |
| DE1206152B (en) * | 1964-03-04 | 1965-12-02 | Bayer Ag | Process for the production of flame-retardant foams containing urethane groups |
| US3220961A (en) * | 1964-05-28 | 1965-11-30 | Weston Chemical Corp | Phosphate and thiophosphate urethanes |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE13961C (en) * | H. MEICHS-NER in Schwarzenberg (Sachsen) | Device for raising and lowering the tops of coaches | ||
| BE576917A (en) * | 1958-03-22 |
-
0
- NL NL126032D patent/NL126032C/xx active
- NL NL254779D patent/NL254779A/xx unknown
- BE BE593966D patent/BE593966A/xx unknown
-
1959
- 1959-08-11 DE DEF29159A patent/DE1106489B/en active Pending
-
1960
- 1960-08-11 GB GB2786660A patent/GB918868A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4234693A (en) * | 1975-06-24 | 1980-11-18 | Imperial Chemical Industries Limited | Process for making polyurea foams utilizing imidazole catalysts |
| US6552159B1 (en) * | 1991-03-15 | 2003-04-22 | Dao-Ichi Kogyo Seiyaku Co., Ltd. | Cladding resin composition |
Also Published As
| Publication number | Publication date |
|---|---|
| BE593966A (en) | |
| NL254779A (en) | |
| DE1106489B (en) | 1961-05-10 |
| NL126032C (en) |
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