DE2463036C2 - - Google Patents
Info
- Publication number
- DE2463036C2 DE2463036C2 DE2463036A DE2463036A DE2463036C2 DE 2463036 C2 DE2463036 C2 DE 2463036C2 DE 2463036 A DE2463036 A DE 2463036A DE 2463036 A DE2463036 A DE 2463036A DE 2463036 C2 DE2463036 C2 DE 2463036C2
- Authority
- DE
- Germany
- Prior art keywords
- halogenated
- polyether polyols
- radical
- polyether polyol
- rigid
- 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
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 46
- 229920000570 polyether Polymers 0.000 claims description 46
- 229920005862 polyol Polymers 0.000 claims description 36
- 150000003077 polyols Chemical class 0.000 claims description 36
- 238000004519 manufacturing process Methods 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 229920005830 Polyurethane Foam Polymers 0.000 claims description 17
- 239000011496 polyurethane foam Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 7
- 229920001228 polyisocyanate Polymers 0.000 claims description 7
- 239000005056 polyisocyanate Substances 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 239000004604 Blowing Agent Substances 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000006260 foam Substances 0.000 description 8
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 7
- 150000002009 diols Chemical group 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 3
- 229940029284 trichlorofluoromethane Drugs 0.000 description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- -1 dibromopropyl Chemical group 0.000 description 2
- 239000004088 foaming agent Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical class [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229910000410 antimony oxide Inorganic materials 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- DLDJFQGPPSQZKI-UHFFFAOYSA-N but-2-yne-1,4-diol Chemical compound OCC#CCO DLDJFQGPPSQZKI-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000009970 fire resistant effect Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 229910052742 iron Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- CABDEMAGSHRORS-UHFFFAOYSA-N oxirane;hydrate Chemical compound O.C1CO1 CABDEMAGSHRORS-UHFFFAOYSA-N 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- XHTMGDWCCPGGET-UHFFFAOYSA-N tris(3,3-dichloropropyl) phosphate Chemical class ClC(Cl)CCOP(=O)(OCCC(Cl)Cl)OCCC(Cl)Cl XHTMGDWCCPGGET-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
- C07C43/137—Saturated ethers containing hydroxy or O-metal groups containing halogen
-
- 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
- C08G18/5003—Polyethers having heteroatoms other than oxygen having halogens
- C08G18/5006—Polyethers having heteroatoms other than oxygen having halogens having chlorine and/or bromine atoms
-
- 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
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/6795—Unsaturated polyethers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7338186A FR2249059B1 (en:Method) | 1973-10-24 | 1973-10-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2463036C2 true DE2463036C2 (en:Method) | 1988-06-23 |
Family
ID=9126946
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2445571A Expired DE2445571C3 (de) | 1973-10-24 | 1974-09-24 | Halogenierte Polyäther-polyole und ein Verfahren zu ihrer Herstellung |
| DE2463036A Expired DE2463036C2 (en:Method) | 1973-10-24 | 1974-09-24 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2445571A Expired DE2445571C3 (de) | 1973-10-24 | 1974-09-24 | Halogenierte Polyäther-polyole und ein Verfahren zu ihrer Herstellung |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4020024A (en:Method) |
| JP (2) | JPS5736898B2 (en:Method) |
| AT (1) | AT333516B (en:Method) |
| BE (1) | BE821314A (en:Method) |
| CA (1) | CA1039311A (en:Method) |
| CH (1) | CH593892A5 (en:Method) |
| DE (2) | DE2445571C3 (en:Method) |
| ES (2) | ES430385A1 (en:Method) |
| FR (1) | FR2249059B1 (en:Method) |
| GB (1) | GB1452842A (en:Method) |
| IT (1) | IT1021330B (en:Method) |
| NL (1) | NL179295C (en:Method) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4225453A (en) * | 1978-07-03 | 1980-09-30 | Air Products And Chemicals, Inc. | Stabilization of flame retardant premix for polyurethane |
| US4223068A (en) * | 1978-09-27 | 1980-09-16 | Freeman Chemical Corporation | Rigid polyurethane foam containing polyester residue digestion product and building panel made therefrom |
| US4198685A (en) * | 1978-11-13 | 1980-04-15 | Wang Laboratories, Inc. | Text editing system having flexible repetitive operation capability with keyboard interactive feature |
| US4219624A (en) * | 1978-11-20 | 1980-08-26 | Olin Corporation | Stabilization of amine catalysts in a composition with halogenated polyols for use in polyurethane foam production |
| US4282332A (en) * | 1979-01-31 | 1981-08-04 | Mobay Chemical Corporation | Polyols derived from 4,4,4-trichloro-1,2-epoxybutane and/or epihalohydrin for use in the production of heat sealable foams |
| US4393248A (en) * | 1981-08-20 | 1983-07-12 | Pennwalt Corporation | Flame retarded halogenated polyol |
| JPS5869219A (ja) * | 1981-10-22 | 1983-04-25 | Takeda Chem Ind Ltd | ポリウレタンフオ−ムの製造法 |
| DE3438526A1 (de) * | 1984-10-20 | 1986-04-24 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von fluessigen, bromhaltigen alkoxylierungsprodukten und deren verwendung zur herstellung von flammwidrigen polyurethanen |
| BE1005728A3 (fr) * | 1992-04-07 | 1993-12-28 | Solvay | Mousses de polyurethanes rigides ignifuges, compositions destinees a leur fabrication et procede pour la fabrication des mousses. |
| IL175339A0 (en) * | 2006-05-01 | 2007-07-24 | Bromine Compounds Ltd | Flame retardant composition |
| US10144798B2 (en) | 2015-12-21 | 2018-12-04 | Covestro Llc | Methods for designing polyisocyanurate foam-forming compositions, related polyisocyanurate foam-forming compositions, and foams produced thereby |
| US10968327B2 (en) | 2018-08-27 | 2021-04-06 | Covestro Llc | Methods for formulating polyisocyanurate foam-forming compositions, related polyisocyanurate foam-forming compositions, and foams produced thereby |
| CN114206576A (zh) | 2019-08-19 | 2022-03-18 | 科思创有限公司 | 使用光学和红外成像生产硬质泡沫板的方法、系统和计算机程序产品 |
| WO2021071811A1 (en) | 2019-10-11 | 2021-04-15 | Covestro Llc | Methods, systems and computer program products for production and application of spray foam using optical and infrared imaging |
| CN111171926B (zh) * | 2019-12-31 | 2022-07-12 | 南京尚勤新材料科技有限公司 | 用于金属切削液的氧化石墨烯改性脂肪酸酰胺的合成方法 |
| US20250129200A1 (en) | 2023-10-18 | 2025-04-24 | Covestro Llc | Polyisocyanurate foam-forming compositions, polyisocyanurate foams, insulated assemblies, and methods of making thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3269961A (en) * | 1961-07-13 | 1966-08-30 | Olin Mathieson | Polyurethane foam prepared from a halogen containing polyether |
| BE629996A (en:Method) * | 1962-03-23 | |||
| FR1487457A (fr) * | 1966-05-26 | 1967-07-07 | Naphtachimie Sa | Mousses de polyuréthane |
-
1973
- 1973-10-24 FR FR7338186A patent/FR2249059B1/fr not_active Expired
-
1974
- 1974-08-30 CH CH1186774A patent/CH593892A5/xx not_active IP Right Cessation
- 1974-09-12 IT IT27234/74A patent/IT1021330B/it active
- 1974-09-24 DE DE2445571A patent/DE2445571C3/de not_active Expired
- 1974-09-24 DE DE2463036A patent/DE2463036C2/de not_active Expired
- 1974-09-25 ES ES430385A patent/ES430385A1/es not_active Expired
- 1974-09-25 NL NLAANVRAGE7412655,A patent/NL179295C/xx not_active IP Right Cessation
- 1974-10-21 CA CA211,899A patent/CA1039311A/en not_active Expired
- 1974-10-22 BE BE149738A patent/BE821314A/xx not_active IP Right Cessation
- 1974-10-23 GB GB4586174A patent/GB1452842A/en not_active Expired
- 1974-10-23 US US05/517,396 patent/US4020024A/en not_active Expired - Lifetime
- 1974-10-23 AT AT853174A patent/AT333516B/de not_active IP Right Cessation
- 1974-10-24 JP JP12199874A patent/JPS5736898B2/ja not_active Expired
-
1976
- 1976-06-30 ES ES449377A patent/ES449377A1/es not_active Expired
-
1981
- 1981-06-23 JP JP56096068A patent/JPS5774324A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5070312A (en:Method) | 1975-06-11 |
| ATA853174A (de) | 1976-03-15 |
| IT1021330B (it) | 1978-01-30 |
| DE2445571B2 (de) | 1981-02-26 |
| JPS5774324A (en) | 1982-05-10 |
| FR2249059A1 (en:Method) | 1975-05-23 |
| US4020024A (en) | 1977-04-26 |
| NL179295C (nl) | 1986-08-18 |
| ES430385A1 (es) | 1977-02-16 |
| CH593892A5 (en:Method) | 1977-12-30 |
| DE2445571A1 (de) | 1975-04-30 |
| NL7412655A (nl) | 1975-04-28 |
| ES449377A1 (es) | 1977-08-01 |
| JPS5736898B2 (en:Method) | 1982-08-06 |
| AT333516B (de) | 1976-11-25 |
| DE2445571C3 (de) | 1982-02-25 |
| GB1452842A (en) | 1976-10-20 |
| JPS61851B2 (en:Method) | 1986-01-11 |
| CA1039311A (en) | 1978-09-26 |
| BE821314A (fr) | 1975-04-22 |
| FR2249059B1 (en:Method) | 1976-10-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OI | Miscellaneous see part 1 | ||
| OI | Miscellaneous see part 1 | ||
| 8110 | Request for examination paragraph 44 | ||
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