GB1040452A - Polyurethane foams - Google Patents
Polyurethane foamsInfo
- Publication number
- GB1040452A GB1040452A GB1257663A GB1257663A GB1040452A GB 1040452 A GB1040452 A GB 1040452A GB 1257663 A GB1257663 A GB 1257663A GB 1257663 A GB1257663 A GB 1257663A GB 1040452 A GB1040452 A GB 1040452A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxide
- polyhydric polyalkylene
- polyhydric
- unsaturated monomers
- ethers
- 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 abstract 2
- 239000011496 polyurethane foam Substances 0.000 title abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 7
- 229920001281 polyalkylene Polymers 0.000 abstract 6
- 150000002170 ethers Chemical class 0.000 abstract 4
- 239000000178 monomer Substances 0.000 abstract 4
- -1 ethylene, propylene Chemical group 0.000 abstract 3
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 abstract 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 abstract 2
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 abstract 1
- QMMOXUPEWRXHJS-HYXAFXHYSA-N (z)-pent-2-ene Chemical compound CC\C=C/C QMMOXUPEWRXHJS-HYXAFXHYSA-N 0.000 abstract 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 abstract 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 abstract 1
- FZIIBDOXPQOKBP-UHFFFAOYSA-N 2-methyloxetane Chemical compound CC1CCO1 FZIIBDOXPQOKBP-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical class C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- 239000004604 Blowing Agent Substances 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
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 239000004721 Polyphenylene oxide Substances 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 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
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000001414 amino alcohols Chemical class 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- 239000012975 dibutyltin dilaurate Substances 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000001033 ether group Chemical group 0.000 abstract 1
- 229920000578 graft copolymer Polymers 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 239000003999 initiator Substances 0.000 abstract 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 abstract 1
- 125000005395 methacrylic acid group Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 abstract 1
- 229920000570 polyether Polymers 0.000 abstract 1
- 229920001228 polyisocyanate Polymers 0.000 abstract 1
- 239000005056 polyisocyanate Substances 0.000 abstract 1
- 229920001451 polypropylene glycol Polymers 0.000 abstract 1
- 229920001296 polysiloxane Polymers 0.000 abstract 1
- 239000004814 polyurethane Substances 0.000 abstract 1
- 229920002635 polyurethane Polymers 0.000 abstract 1
- 230000005855 radiation Effects 0.000 abstract 1
- 150000005846 sugar alcohols Polymers 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 abstract 1
- 229920001567 vinyl ester resin Polymers 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 229920002554 vinyl polymer Chemical class 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
- C08G18/63—Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers
- C08G18/632—Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers onto polyethers
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
Polyurethane foams are prepared by reacting an organic polyisocyanate in the presence of a blowing agent, with a polyhydric polyalkylene ether prepared by effecting polymerization of one or more ethylenically unsaturated monomers in situ in a polyhydric polyalkylene ether. The polyhydric polyalkylene ether may be substantially linear and have a M.W. of 400-5000 and a hydroxyl content of 0.5-15%. Suitable ethers may have graft polymers and/or mixtures of ethylenically unsaturated monomers dissolved in or bonded to the ether. Unsaturated monomers may be: aromatic vinyl compounds, e.g. styrene, olefines, e.g. ethylene, propylene, 1-butylene, 2-hexene, 1,4-hexadiene, 1,3-butadiene, 3-pentene, vinyl esters, e.g. vinyl acetate or propionate, vinyl chloride, vinylidene chloride, arcyclic and methacrylic acids, acrylonitrile, polyvinyl compounds, e.g. triallyl cyanurate and glycol dimethyl acrylate. Suitable polyhydric polyalkylene ethers are those obtained by condensation of ethylene oxide, propylene oxide, 1,2- and 1,3-butylene oxide, styrene oxide, epichlorohydrin and tetrahydro furan. These alkylene oxides may be condensed with polyhydric alcohols and amines. The monomer is preferably used in amount 1-60% by weight and the polymerization is preferably effected in the absence of oxygen with an initiator, e.g. organic oxide or azo compound, or redox systems, e.g. benzoyl peroxide-diethyl toluidine and ferrous-ferric iron systems, or high energy radiation. The polyhydric polyalkylene ethers containing the polymerizate may be used in admixture with other compounds containing active hydrogen atoms, e.g. linear or branched polyesters and polyesteramides, unmodified polyhydric polyalkylene ethers and reaction products of amino alcohols, diamines, hydroxyamines with alkylene oxides or carboxylic acids. In a typical Example (1) vinyl chloride was polymerized in the presence of linear polypropylene glycol of M.W. 2000 and benzoyl peroxide and the thus modified polyether reacted with tolylene diisocyanate in the presence of triethylene diamine, dibutyltin dilaurate, polysiloxane and water to form a foamed polyurethane.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF36419A DE1152536B (en) | 1962-03-30 | 1962-03-30 | Process for the production of foams containing urethane groups |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1040452A true GB1040452A (en) | 1966-08-24 |
Family
ID=7096432
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1257663A Expired GB1040452A (en) | 1962-03-30 | 1963-03-29 | Polyurethane foams |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1152536B (en) |
| GB (1) | GB1040452A (en) |
Cited By (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4018851A (en) * | 1975-03-12 | 1977-04-19 | Loctite Corporation | Curable poly(alkylene) ether polyol-based grafted resins having improved properties |
| US4111865A (en) * | 1974-11-13 | 1978-09-05 | Union Carbide Corporation | Polymer/polyols and polyurethane forms and elastomers therefrom |
| US4272619A (en) | 1979-04-18 | 1981-06-09 | Bayer Aktiengesellschaft | Process for the production of modified polyether polyols and their use in processes for the production of polyurethane plastics |
| FR2473047A1 (en) * | 1980-01-08 | 1981-07-10 | Alcudia Sa | PROCESS FOR THE PREPARATION OF POLYMER POLYOL ETHERS |
| US4323657A (en) | 1979-04-04 | 1982-04-06 | Bayer Aktiengesellschaft | Dispersions of high melting polyesters in polyhydroxyl compounds, a process for their preparation and their use in the production of polyurethanes |
| US4342840A (en) | 1979-12-25 | 1982-08-03 | Asahi Glass Company, Ltd. | Process for producing polymer polyol |
| US4412014A (en) * | 1980-01-21 | 1983-10-25 | The Celotex Corporation | Extraction of polyoxyalkylene surfactants for phenolic foam stabilization |
| US4438018A (en) | 1980-01-21 | 1984-03-20 | The Celotex Corporation | Metal catalyzed preparation of polyoxyalkylene surfactants for phenolic foam stabilization |
| US4469653A (en) * | 1981-07-04 | 1984-09-04 | Basf Aktiengesellschaft | Process for the preparation of molded parts of polyurethane or polyurethane-polyurea employing monocyclic amidines |
| US4485194A (en) * | 1980-01-21 | 1984-11-27 | The Celotex Corporation | Extraction of polyoxyalkylene surfactants for phenolic foam stabilization |
| US4518719A (en) * | 1980-01-21 | 1985-05-21 | The Celotex Corporation | Metal catalyzed preparation of polyoxyalkylene surfactants for phenolic foam stabilization |
| US4520140A (en) * | 1981-07-10 | 1985-05-28 | The Celotex Corporation | Polyoxyalkylene/unsaturated diester reaction product for cellular foam stabilization |
| US4522877A (en) * | 1980-01-21 | 1985-06-11 | The Celotex Corporation | Extraction of polyoxyalkylene surfactants for phenolic foam stabilization |
| US4529745A (en) * | 1983-05-02 | 1985-07-16 | Jim Walter Resources, Inc. | Unsaturated polyoxyalkylene adduct/fumarate diester reaction product for cellular foam stabilization |
| US4546034A (en) * | 1980-01-21 | 1985-10-08 | The Celotex Corporation | Metal catalyzed preparation of polyoxyalkylene surfactants for phenolic foam stabilization |
| US4555442A (en) * | 1981-07-10 | 1985-11-26 | The Celotex Corporation | Polyoxyalkylene/unsaturated diester reaction product for cellular foam stabilization |
| US4563499A (en) * | 1980-01-21 | 1986-01-07 | The Celotex Corporation | Extraction of polyoxyalkylene surfactants for phenolic foam stabilization |
| US4572919A (en) * | 1983-05-02 | 1986-02-25 | Jim Walter Resources, Inc. | Unsaturated polyoxyalkylene adduct/fumarate diester reaction product for cellular foam stabilization |
| US4698371A (en) * | 1984-02-10 | 1987-10-06 | Basf Aktiengesellschaft | Process for the preparation of optionally cellular polyurethane-polyurea molded parts using urethane group- and isocyanurate group-containing 2,4- and/or 2,6-toluene diisocyanates |
| US4729850A (en) * | 1981-07-10 | 1988-03-08 | The Celotex Corporation | Polyoxyalkylene/unsaturated diester reaction product for cellular foam stabilization |
| US5173530A (en) * | 1987-05-15 | 1992-12-22 | Montedipe S.P.A. | Stable dispersions of polyols containing polyvinylchloride |
| US5294445A (en) * | 1991-08-21 | 1994-03-15 | Bayer Aktiengesellschaft | Pesticidal shaped articles |
| US5578653A (en) * | 1994-11-10 | 1996-11-26 | Basf Schwarzheide | Preparation of cellular polyurethanes |
| EP0755968A2 (en) | 1995-07-25 | 1997-01-29 | Basf Aktiengesellschaft | Process for producing hard foam on basis of isocyanate |
| EP0757068A1 (en) | 1995-08-03 | 1997-02-05 | BASF Aktiengesellschaft | Flame retardant rigid foams based on isocyanate |
| US6773756B2 (en) | 2002-03-20 | 2004-08-10 | Bayer Polymers Llc | Process to manufacture three dimensionally shaped substrate for sound abatement |
| DE102007061883A1 (en) | 2007-12-20 | 2009-06-25 | Bayer Materialscience Ag | Viscoelastic polyurethane foam |
| WO2012007419A1 (en) | 2010-07-13 | 2012-01-19 | Bayer Materialscience Ag | Process for preparing polyurethane prepolymers containing isocyanate groups |
| WO2012007418A1 (en) | 2010-07-13 | 2012-01-19 | Bayer Materialscience Ag | Lightly modified prepolymers and uses thereof |
| EP2492297A1 (en) | 2011-02-23 | 2012-08-29 | Basf Se | Polyester polyols on the basis of aromatic dicarbon acids and polyurethane rigid foams obtained therefrom |
| DE102011050220A1 (en) | 2011-05-09 | 2012-11-15 | Bayer Materialscience Aktiengesellschaft | New isocyanate-terminated prepolymer obtained by reacting an isocyanate composition comprising monomeric and polymeric diphenylmethane diisocyanate with a polyester ether polyol, useful to prepare polyurethane/polyisocyanurate polymer |
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Families Citing this family (87)
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|---|---|---|---|---|
| US3422165A (en) * | 1964-12-08 | 1969-01-14 | Union Carbide Corp | Isocyanate and isothiocyanate compositions and polyurethanes thereof |
| CA1022300A (en) | 1971-08-30 | 1977-12-06 | Union Carbide Corporation | Polymer/polyols and process for production thereof |
| US4282331A (en) | 1973-11-20 | 1981-08-04 | Union Carbide Corporation | Polyurethane foam prepared from a copolymer/polyol composition |
| CA1123536A (en) * | 1976-12-20 | 1982-05-11 | Russell Van Cleve | Polymer/polyols via non-aqueous dispersion stabilizers |
| ES504557A0 (en) * | 1981-08-05 | 1982-06-01 | Alcudia Sa | PROCEDURE FOR OBTAINING VINYL COPOLYMERS WITHIN A POLYHYDROXYLIC COMPOUND |
| US4594366A (en) * | 1983-06-29 | 1986-06-10 | Union Carbide Corporation | Connected branched polyols and polyurethanes based thereon |
| ES8604286A1 (en) * | 1985-07-12 | 1986-01-16 | Alcudia Sa | Polymer/polyol dispersions |
| US5830944A (en) * | 1994-03-31 | 1998-11-03 | Basf Aktiengesellschaft | Preparation of polymeric polyesterols |
| DE4431963A1 (en) | 1994-09-08 | 1996-03-14 | Bayer Ag | Process for the preparation of elastic moldings |
| US5554662A (en) * | 1995-03-10 | 1996-09-10 | Bayer Adtiengesellschaft | Low viscosity polymer polyols a process for their production as well as the manufacture of polyurethane from materials |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL237647A (en) * | 1958-04-03 | |||
| GB930397A (en) * | 1960-06-09 | 1900-01-01 |
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