DE1056821B - Verfahren zur Herstellung von vernetzten Polyaetherurethanen - Google Patents
Verfahren zur Herstellung von vernetzten PolyaetherurethanenInfo
- Publication number
- DE1056821B DE1056821B DEI13204A DEI0013204A DE1056821B DE 1056821 B DE1056821 B DE 1056821B DE I13204 A DEI13204 A DE I13204A DE I0013204 A DEI0013204 A DE I0013204A DE 1056821 B DE1056821 B DE 1056821B
- Authority
- DE
- Germany
- Prior art keywords
- groups
- isocyanate groups
- polyether
- parts
- opposite
- 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.)
- Pending
Links
- 229920000570 polyether Polymers 0.000 title claims description 25
- 239000004721 Polyphenylene oxide Substances 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 12
- 150000003673 urethanes Chemical class 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 16
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 14
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 238000000465 moulding Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000003213 activating effect Effects 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 229920001228 polyisocyanate Polymers 0.000 claims 1
- 239000005056 polyisocyanate Substances 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 description 16
- 239000000463 material Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 230000001588 bifunctional effect Effects 0.000 description 5
- 239000003431 cross linking reagent Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000005266 casting Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 238000004898 kneading Methods 0.000 description 3
- 229920000909 polytetrahydrofuran Polymers 0.000 description 3
- -1 water or steam Chemical class 0.000 description 3
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- YHYKLKNNBYLTQY-UHFFFAOYSA-N 1,1-diphenylhydrazine Chemical compound C=1C=CC=CC=1N(N)C1=CC=CC=C1 YHYKLKNNBYLTQY-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- SQMOOVFBFVTTGF-UHFFFAOYSA-N 1-benzyl-1-phenylhydrazine Chemical compound C=1C=CC=CC=1N(N)CC1=CC=CC=C1 SQMOOVFBFVTTGF-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- MWBPRDONLNQCFV-UHFFFAOYSA-N Tri-allate Chemical group CC(C)N(C(C)C)C(=O)SCC(Cl)=C(Cl)Cl MWBPRDONLNQCFV-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000005415 aminobenzoic acids Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- WPJWIROQQFWMMK-UHFFFAOYSA-L beryllium dihydroxide Chemical compound [Be+2].[OH-].[OH-] WPJWIROQQFWMMK-UHFFFAOYSA-L 0.000 description 1
- 229910001865 beryllium hydroxide Inorganic materials 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical class CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- MXHTZQSKTCCMFG-UHFFFAOYSA-N n,n-dibenzyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 MXHTZQSKTCCMFG-UHFFFAOYSA-N 0.000 description 1
- 230000006855 networking Effects 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000003198 secondary alcohol group Chemical group 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 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
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7678—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing condensed aromatic rings
-
- 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
- C08G18/088—Removal of water or carbon dioxide from the reaction mixture or reaction components
- C08G18/0885—Removal of water or carbon dioxide from the reaction mixture or reaction components using additives, e.g. absorbing agents
-
- 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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
-
- 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
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/222—Catalysts containing metal compounds metal compounds not provided for in groups C08G18/225 - C08G18/26
-
- 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
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/225—Catalysts containing metal compounds of alkali or alkaline earth metals
-
- 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
- C08G18/4825—Polyethers containing two 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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB318202X | 1952-04-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1056821B true DE1056821B (de) | 1959-05-06 |
Family
ID=10328893
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI13204A Pending DE1056821B (de) | 1952-04-10 | 1953-04-10 | Verfahren zur Herstellung von vernetzten Polyaetherurethanen |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE519014A (en, 2012) |
| CH (5) | CH341645A (en, 2012) |
| DE (1) | DE1056821B (en, 2012) |
| FR (1) | FR1074451A (en, 2012) |
| GB (1) | GB733624A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1177818B (de) * | 1961-06-29 | 1964-09-10 | Du Pont | Verfahren zur Herstellung von Polyurethanelastomeren |
Families Citing this family (74)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2917488A (en) * | 1959-12-15 | X x x x x | ||
| US2929803A (en) * | 1955-01-31 | 1960-03-22 | Du Pont | Elastic copolyureas from secondary diamines and process for making the same |
| US2929802A (en) * | 1955-01-31 | 1960-03-22 | Du Pont | Elastic filaments of linear copolyurethanes |
| US2929804A (en) * | 1955-01-31 | 1960-03-22 | Du Pont | Elastic filaments of linear segmented polymers |
| US2929801A (en) * | 1955-01-31 | 1960-03-22 | Du Pont | Elastic amide/urethane/ether copolymers and process for making the same |
| US2843568A (en) * | 1955-01-31 | 1958-07-15 | Du Pont | Polymeric polyether-polyurethanes |
| DE1069379B (de) * | 1955-03-24 | 1959-11-19 | E. I. du Pont de Nemours and Company, Wilmington, 1DeI. (V. St. A.) | Verfahren zur Herstellung homogener Kunststoffe auf Grundlage Urethangrup'pen und gegebenenfalls auch Thioärhergruppen aufweisender Polyglykoläther |
| DE1104174B (de) * | 1955-08-04 | 1961-04-06 | Du Pont | Verfahren zur Herstellung eines Urethangruppen aufweisenden Elastomeren |
| US2948707A (en) * | 1955-09-14 | 1960-08-09 | Du Pont | Isocyanate-based polymers containing at least two different types of polymeric segments |
| US2961428A (en) * | 1955-10-24 | 1960-11-22 | Bayer Ag | Polyacetal-polyisocyanate polymers |
| DE1059656B (de) * | 1955-11-21 | 1959-06-18 | Us Rubber Co | Herstellung von offenporigen Schaumstoffen |
| DE1161007B (de) * | 1955-12-29 | 1964-01-09 | E. I. du Pont de Nemours & Company, Wilmington, Del. (V. St. A.) | Herstellung von Kunstharzfolien oder -Fäden |
| US2901467A (en) * | 1956-04-20 | 1959-08-25 | Du Pont | Polyurethane coating compositions |
| US2899411A (en) * | 1956-07-30 | 1959-08-11 | Polyurethane elastomers from hy- | |
| US3042631A (en) * | 1956-08-03 | 1962-07-03 | Simoniz Co | Polyurethane prepolymer and expanded product prepared therefrom |
| BE560394A (en, 2012) * | 1956-09-18 | |||
| DE1029559B (de) * | 1956-11-16 | 1958-05-08 | Bayer Ag | Verfahren zur Herstellung hochmolekularer vernetzter Kunststoffe unter Formgebung |
| BE562462A (en, 2012) * | 1956-11-20 | |||
| US3036997A (en) * | 1956-11-21 | 1962-05-29 | Du Pont | Diene-modified polymers and elastomers thereform |
| US2983693A (en) * | 1956-12-20 | 1961-05-09 | Du Pont | Isocyanate terminated polyurethane adhesive composition |
| US2881065A (en) * | 1957-02-18 | 1959-04-07 | Mobay Chemical Corp | Polishing instrument |
| US3287330A (en) * | 1958-02-06 | 1966-11-22 | Du Pont | Polyether polymers having unsaturated side chains |
| BE566580A (en, 2012) * | 1957-04-08 | |||
| US2980651A (en) * | 1957-04-29 | 1961-04-18 | Du Pont | Polyureylenes |
| US2830038A (en) * | 1957-05-07 | 1958-04-08 | Du Pont | Poly (polyalkylene ether urethane) polymers containing terminal epoxide groups |
| US3004840A (en) * | 1957-10-17 | 1961-10-17 | Dow Chemical Co | Solid composite propellants containing polyalkylene oxides |
| US3074911A (en) * | 1957-12-05 | 1963-01-22 | Du Pont | Polyurethane resin coating composition containing carbamyl chloride stabilizer |
| US3009901A (en) * | 1958-01-09 | 1961-11-21 | Du Pont | Reaction products of phenolic diamines with isocyanate terminated polyethers |
| US2964422A (en) * | 1958-02-28 | 1960-12-13 | Johnson & Johnson | Pressure sensitive adhesive sheet and method of manufacture |
| US2956031A (en) * | 1958-04-04 | 1960-10-11 | Allied Chem | Highly cross-linked non-flammable polyurethane compositions and preparation of same |
| US2953533A (en) * | 1958-04-04 | 1960-09-20 | Allied Chem | Highly cross-linked non flammable polyurethane foams and preparation of same |
| BE580827A (en, 2012) * | 1958-08-18 | |||
| US3004939A (en) * | 1958-08-19 | 1961-10-17 | Us Rubber Co | Method of making polyurethane rubber articles |
| US3098658A (en) * | 1958-11-12 | 1963-07-23 | Goodrich Co B F | Golf ball having a polyetherurethane core |
| US3148173A (en) * | 1959-01-26 | 1964-09-08 | Wyandotte Chemicals Corp | Polyurethane-ureas containing urealinked nu-(2-hydroxypropyl) alkylene diamines |
| GB880665A (en) * | 1959-01-26 | 1961-10-25 | Wyandotte Chemicals Corp | Polyurethane-ureas containing urea-linked piperazine compounds |
| US3049513A (en) * | 1959-03-26 | 1962-08-14 | Wyandotte Chemicals Corp | Ordered isocyanate-terminated polyether-based urethane compositions |
| US3033825A (en) * | 1959-03-26 | 1962-05-08 | Goodrich Co B F | Stable polyurethane rubbers |
| BE590114A (en, 2012) * | 1959-04-25 | |||
| US3054778A (en) * | 1959-10-19 | 1962-09-18 | Dow Chemical Co | Acetic anhydride modified polyurethane |
| US3147974A (en) * | 1959-11-12 | 1964-09-08 | American Mach & Foundry | Synthetic bowling pins |
| GB965220A (en) * | 1960-04-05 | 1964-07-29 | Dunlop Rubber Co | Improvements in and relating to polyurethanes |
| DE1160651B (de) * | 1960-04-14 | 1964-01-02 | Henschel Werke Ag | Schublehre zur Bestimmung des Durchmessers und Versatzes von Werkstuecken, insbesondere Rohren und Wellen |
| US3201136A (en) * | 1960-07-06 | 1965-08-17 | Minnesota Mining & Mfg | Pipe joint of cast in place polyurethane |
| US3192187A (en) * | 1961-01-17 | 1965-06-29 | Air Prod & Chem | Preparation of stretchable polyurethane castings using a cocatalyst system of an epoxy alkane and a bicyclic amine |
| US3165566A (en) * | 1961-06-29 | 1965-01-12 | Goodrich Co B F | One step polyamine curing for polyurethane threads |
| US3359217A (en) * | 1961-07-21 | 1967-12-19 | Atlas Chem Ind | Rigid urethane foam compositions prepared utilizing an acid catalyzed sorbitol-propylene oxide condensation product |
| BE624887A (en, 2012) * | 1961-11-16 | |||
| US3267078A (en) * | 1963-12-16 | 1966-08-16 | Wyandotte Chemicals Corp | Polyether urethane coating composition cured with a di-imine |
| CA673674A (en) * | 1965-02-24 | 1963-11-05 | Wismer Marco | Glass-resin laminates |
| US3475803A (en) * | 1965-08-27 | 1969-11-04 | Edward D Hill | Roller for applying paint,ink and the like |
| JP2502132B2 (ja) * | 1988-09-30 | 1996-05-29 | 三菱重工業株式会社 | 形状記憶ポリウレタンエラストマ―成形体 |
| DE4308791A1 (de) * | 1993-03-18 | 1994-09-22 | Bayer Ag | Verfahren zur thermoplastischen Verarbeitung von Polyurethanen |
| US6803495B2 (en) | 2000-06-28 | 2004-10-12 | World Properties, Inc. | Polyurethane foam composition and method of manufacture thereof |
| US6635688B2 (en) | 2000-06-28 | 2003-10-21 | World Properties, Inc. | Composite polyurethane foams and method of manufacture thereof |
| AU2001271571A1 (en) | 2000-06-28 | 2002-01-08 | World Properties Inc. | Tough, fire resistant polyurethane foam and method of manufacture thereof |
| WO2002007960A1 (en) | 2000-07-26 | 2002-01-31 | World Properties, Inc. | Compressible foam tapes and methods of manufacture thereof |
| WO2002051902A1 (en) | 2000-12-27 | 2002-07-04 | World Properties Inc. | Polyurethane foams and method of manafacture thereof |
| US6653361B2 (en) | 2000-12-29 | 2003-11-25 | World Properties, Inc. | Flame retardant polyurethane composition and method of manufacture thereof |
| US6780516B2 (en) | 2002-01-31 | 2004-08-24 | General Electric Company | Anti-fog coating composition, process, and article |
| US6852823B2 (en) * | 2002-08-09 | 2005-02-08 | E. I. Du Pont De Nemours And Company | Polyurethane and polyurethane-urea elastomers from polytrimethylene ether glycol |
| US7338983B2 (en) | 2004-02-10 | 2008-03-04 | World Properties, Inc. | Low density polyurethane foam, method of producing, and articles comprising the same |
| DE102006030391A1 (de) * | 2006-07-01 | 2008-01-10 | Bayer Materialscience Ag | Geschäumte und massive Polyurethanelastomere auf Basis von 1,5-Naphthalindiisocyanat, Verfahren zu ihrer Herstellung und ihre Verwendung |
| KR101352235B1 (ko) | 2009-05-27 | 2014-01-15 | 로저스코포레이션 | 연마 패드, 이를 위한 폴리우레탄층, 및 규소 웨이퍼의 연마 방법 |
| US9629283B2 (en) | 2014-06-05 | 2017-04-18 | Rogers Corporation | Compressible thermally conductive articles |
| TW201634514A (zh) | 2015-02-05 | 2016-10-01 | 羅傑斯公司 | 發泡體產物及其製備方法 |
| WO2018048831A1 (en) | 2016-09-07 | 2018-03-15 | Rogers Corporation | Compressible thermally conductive articles |
| JP2019530789A (ja) | 2016-10-17 | 2019-10-24 | ロジャーズ コーポレーション | ポリウレタン及び組成物並びにそれらから形成される部材の硬化を遅延させる為の方法 |
| WO2018093987A1 (en) | 2016-11-16 | 2018-05-24 | Rogers Corporation | Method for the manufacture of thermally conductive composite materials and articles comprising the same |
| US20190077661A1 (en) | 2017-09-14 | 2019-03-14 | Rogers Corporation | Boron nitride foam, methods of manufacture thereof, and articles containing the boron nitride foam |
| US20210292463A1 (en) * | 2020-03-18 | 2021-09-23 | Northwestern University | Dynamic polyurethane networks with post-recycling retention of cross-linking densities and mechanical properties |
| CN111393467A (zh) * | 2020-04-26 | 2020-07-10 | 扬州天启新材料股份有限公司 | 基于化学键合的有机硅增韧异氰酸酯树脂的制备方法 |
| CN113621121B (zh) * | 2021-07-15 | 2022-08-23 | 中联重科股份有限公司 | 聚氨酯组合物和聚氨酯材料的制备方法及应用 |
| WO2024228939A1 (en) | 2023-05-03 | 2024-11-07 | Rogers Corporation | Thermal management sheet, method of manufacture, and articles using the same |
-
0
- BE BE519014D patent/BE519014A/xx unknown
-
1952
- 1952-04-10 GB GB9207/52A patent/GB733624A/en not_active Expired
-
1953
- 1953-04-09 CH CH341645D patent/CH341645A/de unknown
- 1953-04-09 CH CH346024D patent/CH346024A/de unknown
- 1953-04-09 CH CH341310D patent/CH341310A/de unknown
- 1953-04-09 CH CH318202D patent/CH318202A/de unknown
- 1953-04-09 CH CH342750D patent/CH342750A/de unknown
- 1953-04-10 FR FR1074451D patent/FR1074451A/fr not_active Expired
- 1953-04-10 DE DEI13204A patent/DE1056821B/de active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1177818B (de) * | 1961-06-29 | 1964-09-10 | Du Pont | Verfahren zur Herstellung von Polyurethanelastomeren |
Also Published As
| Publication number | Publication date |
|---|---|
| GB733624A (en) | 1955-07-13 |
| BE519014A (en, 2012) | |
| FR1074451A (fr) | 1954-10-06 |
| CH341310A (de) | 1959-09-30 |
| CH342750A (de) | 1959-11-30 |
| CH318202A (de) | 1956-12-31 |
| CH341645A (de) | 1959-10-15 |
| CH346024A (de) | 1960-04-30 |
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