CA1337448C - Process for the preparation of polyurea elastomers containing urethane groups - Google Patents
Process for the preparation of polyurea elastomers containing urethane groupsInfo
- Publication number
- CA1337448C CA1337448C CA000607379A CA607379A CA1337448C CA 1337448 C CA1337448 C CA 1337448C CA 000607379 A CA000607379 A CA 000607379A CA 607379 A CA607379 A CA 607379A CA 1337448 C CA1337448 C CA 1337448C
- Authority
- CA
- Canada
- Prior art keywords
- component
- process according
- isocyanate
- polyisocyanate
- polyol
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 48
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 229920001971 elastomer Polymers 0.000 title claims abstract description 12
- 239000000806 elastomer Substances 0.000 title claims abstract description 12
- 229920002396 Polyurea Polymers 0.000 title claims abstract description 11
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 44
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 43
- 239000012948 isocyanate Substances 0.000 claims abstract description 42
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 42
- 229920005862 polyol Polymers 0.000 claims abstract description 37
- 150000003077 polyols Chemical class 0.000 claims abstract description 37
- 239000000203 mixture Substances 0.000 claims abstract description 36
- 150000004985 diamines Chemical class 0.000 claims abstract description 30
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 18
- 229920000570 polyether Polymers 0.000 claims abstract description 18
- 238000000465 moulding Methods 0.000 claims abstract description 16
- 238000010107 reaction injection moulding Methods 0.000 claims abstract description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
- 239000000654 additive Substances 0.000 claims abstract description 11
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000003277 amino group Chemical group 0.000 claims abstract description 9
- 150000004984 aromatic diamines Chemical class 0.000 claims abstract description 9
- 229920005906 polyester polyol Polymers 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 230000001413 cellular effect Effects 0.000 claims abstract description 4
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 6
- RQEOBXYYEPMCPJ-UHFFFAOYSA-N 4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N RQEOBXYYEPMCPJ-UHFFFAOYSA-N 0.000 claims description 5
- 238000007385 chemical modification Methods 0.000 claims description 3
- 239000012766 organic filler Substances 0.000 claims description 3
- 239000011256 inorganic filler Substances 0.000 claims 1
- 229910003475 inorganic filler Inorganic materials 0.000 claims 1
- 239000004814 polyurethane Substances 0.000 abstract description 3
- 229920002635 polyurethane Polymers 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-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
- 239000000047 product Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000003750 conditioning effect Effects 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- 239000006082 mold release agent Substances 0.000 description 4
- 239000004604 Blowing Agent Substances 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- -1 for example Chemical class 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000007046 ethoxylation reaction Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 2
- 239000012764 mineral filler Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
- UCUPHRPMBXOFAU-UHFFFAOYSA-N 2,4,6-tri(propan-2-yl)benzene-1,3-diamine Chemical compound CC(C)C1=CC(C(C)C)=C(N)C(C(C)C)=C1N UCUPHRPMBXOFAU-UHFFFAOYSA-N 0.000 description 1
- JGYUBHGXADMAQU-UHFFFAOYSA-N 2,4,6-triethylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(CC)=C1N JGYUBHGXADMAQU-UHFFFAOYSA-N 0.000 description 1
- ZVDSMYGTJDFNHN-UHFFFAOYSA-N 2,4,6-trimethylbenzene-1,3-diamine Chemical group CC1=CC(C)=C(N)C(C)=C1N ZVDSMYGTJDFNHN-UHFFFAOYSA-N 0.000 description 1
- HGXVKAPCSIXGAK-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine;4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N.CCC1=CC(C)=C(N)C(CC)=C1N HGXVKAPCSIXGAK-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- LNWBFIVSTXCJJG-UHFFFAOYSA-N [diisocyanato(phenyl)methyl]benzene Chemical class C=1C=CC=CC=1C(N=C=O)(N=C=O)C1=CC=CC=C1 LNWBFIVSTXCJJG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 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
- C08G18/70—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
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C45/00—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor
-
- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
-
- 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
- C08G18/4829—Polyethers containing at least three hydroxy groups
-
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
-
- 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
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0008—Foam properties flexible
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0033—Foam properties having integral skins
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0041—Foam properties having specified density
- C08G2110/0066—≥ 150kg/m3
-
- 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
- C08G2120/00—Compositions for reaction injection moulding processes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Mechanical Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
- Injection Moulding Of Plastics Or The Like (AREA)
- Casting Or Compression Moulding Of Plastics Or The Like (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3827595.3 | 1988-08-13 | ||
| DE3827595A DE3827595A1 (de) | 1988-08-13 | 1988-08-13 | Verfahren zur herstellung von urethangruppen ausweisenden polyharnstoff-elastomeren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1337448C true CA1337448C (en) | 1995-10-24 |
Family
ID=6360842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000607379A Expired - Fee Related CA1337448C (en) | 1988-08-13 | 1989-08-02 | Process for the preparation of polyurea elastomers containing urethane groups |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0355000B2 (enrdf_load_stackoverflow) |
| JP (1) | JPH07103211B2 (enrdf_load_stackoverflow) |
| KR (1) | KR970010624B1 (enrdf_load_stackoverflow) |
| CA (1) | CA1337448C (enrdf_load_stackoverflow) |
| DE (2) | DE3827595A1 (enrdf_load_stackoverflow) |
| ES (1) | ES2031321T5 (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7393491B2 (en) | 2000-09-11 | 2008-07-01 | Dow Global Technologies Inc. | Method for preparing a tire support |
| US9315622B2 (en) | 2011-07-18 | 2016-04-19 | Covestro Deutschland Ag | Process for the production of polyether carbonate polyols |
| US9512258B2 (en) | 2012-06-06 | 2016-12-06 | Covestro Deutschland Ag | Process for the production of viscoelastic polyurethane foam |
| US9701804B2 (en) | 2010-11-22 | 2017-07-11 | Covestro Deutschland Ag | Method for producing flexible polyurethane foams |
| US10106641B2 (en) | 2013-11-27 | 2018-10-23 | Covestro Deutschland Ag | Mixtures of polyether carbonate polyols and polyether polyols for producing polyurethane soft foams |
| US10563032B2 (en) | 2014-11-18 | 2020-02-18 | Covestro Deutschland Ag | Method for producing flame retardant polyurethane foams using halogen-free flame retardants |
| US11130842B2 (en) | 2011-06-01 | 2021-09-28 | Covestro Deutschland Ag | Process for the preparation of polyether polyols |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3914718A1 (de) * | 1989-05-04 | 1990-11-08 | Bayer Ag | Verfahren zur herstellung von urethangruppen aufweisenden polyharnstoff-elastomeren |
| DE4115037A1 (de) * | 1991-05-08 | 1992-11-12 | Bayer Ag | Verfahren zur herstellung von urethangruppen aufweisenden polyharnstoff-elastomeren |
| GB9125918D0 (en) * | 1991-12-05 | 1992-02-05 | Ici Plc | Reaction system for preparing polyurethane/polyurea |
| WO1994000504A1 (en) * | 1992-06-26 | 1994-01-06 | Minnesota Mining And Manufacturing Company | Polyurethane/polyurea elastomers |
| DE19618392A1 (de) * | 1996-05-08 | 1997-11-13 | Basf Ag | Verfahren zur Herstellung von elastischen Polyurethan-Formkörpern mit kompakter Oberfläche und zelligem Kern |
| DE19713566C2 (de) * | 1997-04-02 | 1999-11-18 | Daimler Chrysler Ag | Verfahren zum Herstellen eines Formwerkzeugs, Vorrichtung zum Schäumen von Formschaumteilen sowie Verfahren zum Herstellen eines Formwerkzeugs |
| DE59911365D1 (de) * | 1998-11-27 | 2005-02-03 | Bayer Materialscience Ag | Verfahren zur Herstellung von faserverstärkten Polyurethanharnstoff-Elastomeren |
| KR20020097407A (ko) * | 2001-06-20 | 2002-12-31 | 이대훈 | 급결용 폴리우레탄 앵커 조성물 |
| KR20020097408A (ko) * | 2001-06-20 | 2002-12-31 | 송림기업 주식회사 | 충진용 발포성의 폴리우레탄 앵커조성물 |
| DE102008030763A1 (de) | 2008-06-28 | 2009-12-31 | Bayer Materialscience Ag | Verfahren zur Erniedrigung von Emissionen eines Polyurethanschaumstoffes |
| DE102009005609B3 (de) * | 2009-01-21 | 2010-07-01 | Bayer Materialscience Ag | Werkzeug und Verfahren zur Herstellung von Mehrschicht-Kunststoffformteilen |
| DE102009047846A1 (de) | 2009-09-30 | 2011-03-31 | Bayer Materialscience Ag | Verfahren zur Erniedrigung von Emissionen eines Polyurethanschaumstoffes |
| CN101892014A (zh) * | 2010-08-24 | 2010-11-24 | 青岛沙木国际贸易有限公司 | 一种用于喷砂处理的弹性磨料 |
| US20130237624A1 (en) | 2010-11-22 | 2013-09-12 | Bayer Intellectual Property Gmbh | Method for producing flexible polyurethane foams |
| EP2465890A1 (de) | 2010-12-17 | 2012-06-20 | Bayer MaterialScience AG | Verfahren zur Herstellung von Polyethercarbonatpolyolen mit primären Hydroxyl-Endgruppen und daraus hergestellte Polyurethanpolymere |
| BR112013024740A2 (pt) | 2011-03-28 | 2016-12-27 | Bayer Ip Gmbh | processo para a produção de materiais de espumas flexíveis de poliuretanos |
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| MX2015005824A (es) | 2012-11-09 | 2015-09-24 | Bayer Materialscience Ag | Procedimiento para la produccion de polietercarbonatopolioles. |
| US20180237577A1 (en) | 2015-02-27 | 2018-08-23 | Covestro Deutschland Ag | Use of polyether carbonate polyols for producing polyurethane foams with stable colour |
| WO2017085201A1 (de) | 2015-11-19 | 2017-05-26 | Covestro Deutschland Ag | Polyurethanschaumstoffe basierend auf polyethercarbonatpolyolen |
| EP3178858A1 (de) | 2015-12-09 | 2017-06-14 | Covestro Deutschland AG | Polyurethanschaumstoffe basierend auf polyethercarbonatpolyolen |
| SG11201804635PA (en) | 2015-12-09 | 2018-07-30 | Covestro Deutschland Ag | Polyurethane foams based on polyethercarbonate polyols |
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| EP3536727A1 (de) | 2018-03-07 | 2019-09-11 | Covestro Deutschland AG | Polyurethanschaumstoffe basierend auf polyethercarbonatpolyolen |
| EP3543268A1 (de) | 2018-03-22 | 2019-09-25 | Covestro Deutschland AG | Verfahren zur herstellung von polyurethanweichschaumstoffen |
| US20210002412A1 (en) | 2018-03-22 | 2021-01-07 | Covestro Intellectual Property Gmbh & Co. Kg | Method for producing polyurethane soft foams with high bulk density |
| EP3549969A1 (de) | 2018-04-06 | 2019-10-09 | Covestro Deutschland AG | Polyurethanschaumstoffe basierend auf polyethercarbonatpolyolen |
| EP3594255A1 (de) | 2018-07-09 | 2020-01-15 | Covestro Deutschland AG | Verfahren zur herstellung von viskoelastischen polyurethanschaumstoffen |
| CN110669199A (zh) * | 2019-10-24 | 2020-01-10 | 山东一诺威聚氨酯股份有限公司 | 高频筛用聚氨酯弹性体及其制备方法 |
| EP3838964A1 (de) | 2019-12-18 | 2021-06-23 | Covestro Deutschland AG | Polyurethanschaumstoffe basierend auf polyethercarbonatpolyolen |
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| EP4101873A1 (de) | 2021-06-11 | 2022-12-14 | Covestro Deutschland AG | Einsatz von bismut-katalysatoren zur verringerung von cyclischem propylencarbonat bei der herstellung von weichschaumstoffen basierend auf polyethercarbonatpolyolen |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1240654B (de) * | 1965-05-14 | 1967-05-18 | Bayer Ag | Verfahren zur Herstellung vernetzter Kunststoffe nach dem Isocyanat-Polyadditions-Verfahren |
| DE2622951B2 (de) * | 1976-05-21 | 1979-09-06 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von elastischen Fonnkörpern |
| US4374210A (en) * | 1981-09-18 | 1983-02-15 | The Upjohn Company | Polyurea-polyurethane from a mixture of a polyol, an aromatic diamine, and an isocyanate-terminated prepolymer |
| DE3433979A1 (de) * | 1984-09-15 | 1986-03-27 | Bayer Ag, 5090 Leverkusen | Verwendung von sterisch gehinderten aromatischen diaminen bei der herstellung von polyurethanschaumstoffen |
| DE3610729A1 (de) * | 1986-03-29 | 1987-10-01 | Bayer Ag | Verfahren zur herstellung von thixotropen bindemitteln, die nach diesem verfahren erhaeltlichen bindemittel und ihre verwendung zur herstellung von beschichtungs- und abdichtungsmitteln |
-
1988
- 1988-08-13 DE DE3827595A patent/DE3827595A1/de active Granted
-
1989
- 1989-07-29 ES ES89114063T patent/ES2031321T5/es not_active Expired - Lifetime
- 1989-07-29 DE DE8989114063T patent/DE58901470D1/de not_active Expired - Lifetime
- 1989-07-29 EP EP89114063A patent/EP0355000B2/de not_active Expired - Lifetime
- 1989-08-02 CA CA000607379A patent/CA1337448C/en not_active Expired - Fee Related
- 1989-08-09 JP JP1206581A patent/JPH07103211B2/ja not_active Expired - Lifetime
- 1989-08-11 KR KR1019890011429A patent/KR970010624B1/ko not_active Expired - Fee Related
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7393491B2 (en) | 2000-09-11 | 2008-07-01 | Dow Global Technologies Inc. | Method for preparing a tire support |
| US9701804B2 (en) | 2010-11-22 | 2017-07-11 | Covestro Deutschland Ag | Method for producing flexible polyurethane foams |
| US11130842B2 (en) | 2011-06-01 | 2021-09-28 | Covestro Deutschland Ag | Process for the preparation of polyether polyols |
| US9315622B2 (en) | 2011-07-18 | 2016-04-19 | Covestro Deutschland Ag | Process for the production of polyether carbonate polyols |
| US9512258B2 (en) | 2012-06-06 | 2016-12-06 | Covestro Deutschland Ag | Process for the production of viscoelastic polyurethane foam |
| US10106641B2 (en) | 2013-11-27 | 2018-10-23 | Covestro Deutschland Ag | Mixtures of polyether carbonate polyols and polyether polyols for producing polyurethane soft foams |
| US10563032B2 (en) | 2014-11-18 | 2020-02-18 | Covestro Deutschland Ag | Method for producing flame retardant polyurethane foams using halogen-free flame retardants |
| US11192991B2 (en) | 2014-11-18 | 2021-12-07 | Covestro Deutschland Ag | Method for producing flame retardant polyurethane foams using halogen-free flame retardants |
Also Published As
| Publication number | Publication date |
|---|---|
| KR900003230A (ko) | 1992-03-26 |
| ES2031321T3 (es) | 1992-12-01 |
| EP0355000A1 (de) | 1990-02-21 |
| DE3827595A1 (de) | 1990-02-22 |
| DE3827595C2 (enrdf_load_stackoverflow) | 1990-10-18 |
| JPH07103211B2 (ja) | 1995-11-08 |
| ES2031321T5 (es) | 1995-08-16 |
| JPH0288616A (ja) | 1990-03-28 |
| EP0355000B2 (de) | 1995-01-25 |
| KR970010624B1 (ko) | 1997-06-28 |
| DE58901470D1 (de) | 1992-06-25 |
| EP0355000B1 (de) | 1992-05-20 |
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