NO125591B - - Google Patents
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- Publication number
- NO125591B NO125591B NO2943/69A NO294369A NO125591B NO 125591 B NO125591 B NO 125591B NO 2943/69 A NO2943/69 A NO 2943/69A NO 294369 A NO294369 A NO 294369A NO 125591 B NO125591 B NO 125591B
- Authority
- NO
- Norway
- Prior art keywords
- mol
- diisocyanate
- mixture
- dimethylformamide
- diphenylmethane
- Prior art date
Links
- 239000000203 mixture Substances 0.000 claims description 62
- 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 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 23
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 21
- 229920002635 polyurethane Polymers 0.000 claims description 20
- 239000004814 polyurethane Substances 0.000 claims description 20
- 125000005442 diisocyanate group Chemical group 0.000 claims description 18
- 239000004970 Chain extender Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 150000002009 diols Chemical class 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- -1 aliphatic aminohydroxy compound Chemical class 0.000 claims description 9
- 239000002243 precursor Substances 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 150000004985 diamines Chemical class 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000002429 hydrazines Chemical class 0.000 claims description 4
- 238000003860 storage Methods 0.000 claims description 3
- 230000008569 process Effects 0.000 claims 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 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 237
- 238000003756 stirring Methods 0.000 description 30
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 20
- 238000002156 mixing Methods 0.000 description 17
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 13
- 238000004090 dissolution Methods 0.000 description 9
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 9
- 239000000499 gel Substances 0.000 description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000002649 leather substitute Substances 0.000 description 6
- 238000007792 addition Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 description 2
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 description 1
- 229920001634 Copolyester Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920000921 polyethylene adipate Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000007306 turnover Effects 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
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)
- Synthetic Leather, Interior Materials Or Flexible Sheet Materials (AREA)
- Artificial Filaments (AREA)
- Treatment And Processing Of Natural Fur Or Leather (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681770884 DE1770884C3 (de) | 1968-07-13 | Verfahren zur Herstellung von Polyurethanen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO125591B true NO125591B (xx) | 1972-10-02 |
Family
ID=5700680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2943/69A NO125591B (xx) | 1968-07-13 | 1969-07-14 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3635907A (xx) |
| JP (1) | JPS4825433B1 (xx) |
| AT (1) | AT296609B (xx) |
| BE (1) | BE735368A (xx) |
| CA (1) | CA928446A (xx) |
| CH (1) | CH514644A (xx) |
| DK (1) | DK123172B (xx) |
| ES (1) | ES369457A1 (xx) |
| FI (1) | FI50991C (xx) |
| FR (1) | FR2014588A1 (xx) |
| GB (1) | GB1263937A (xx) |
| LU (1) | LU59043A1 (xx) |
| NL (1) | NL6910606A (xx) |
| NO (1) | NO125591B (xx) |
| SE (1) | SE359849B (xx) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2126932A1 (en) * | 1971-01-28 | 1972-10-13 | Naphtachimie Sa | Polyurethane coatings - for use in making artificial leathers |
| IN141398B (xx) * | 1973-05-16 | 1977-02-26 | Ethicon Inc | |
| DE2409789C3 (de) * | 1974-03-01 | 1981-08-20 | Akzo Gmbh, 5600 Wuppertal | Verfahren zur Herstellung von Polyurethanlösungen sowie deren Anwendung |
| US4083815A (en) * | 1976-03-11 | 1978-04-11 | The Upjohn Company | Polyurethane coating compositions and process of preparation |
| US4326043A (en) * | 1981-01-19 | 1982-04-20 | Basf Wyandotte Corporation | Process for the preparation of polyisocyanurate dispersions modified with halogenated alcohols and compositions prepared therefrom |
| FR2511014B1 (fr) * | 1981-08-10 | 1987-02-06 | Ethicon Inc | Procede de preparation d'une resine de polyurethanne convenant pour le filage electrostatique |
| US4839456A (en) * | 1983-07-12 | 1989-06-13 | Keith Kent | Self-adhesive, drag reducing polymeric coating |
| JPS60104117A (ja) * | 1983-11-11 | 1985-06-08 | Toyota Motor Corp | 導電性改良ポリウレタン |
| DE3407031A1 (de) * | 1984-02-27 | 1985-09-05 | Gurit-Essex, Freienbach | Chemisch haertende zweikomponentenmasse auf der basis von polyurethanen, verfahren zur herstellung einer haertbaren masse auf polyurethanbasis und verwendung von mischungen aus zwei komponenten auf polyurethanbasis |
| GB8416230D0 (en) * | 1984-06-26 | 1984-08-01 | Btr Plc | Polyurethanes |
| US4550153A (en) * | 1984-10-26 | 1985-10-29 | Basf Wyandotte Corporation | Elastomer based on crude diphenylmethane diisocyanate and aniline in the RIM process |
| US5308695A (en) * | 1988-10-18 | 1994-05-03 | Nitto Denko Corporation | Adhesive tapes for medical or sanitary use |
| US5264281A (en) * | 1988-10-18 | 1993-11-23 | Nitto Denko Corporation | Adhesive tapes for medical or sanitary use |
| US5310852A (en) * | 1991-04-26 | 1994-05-10 | Kuraray Co., Ltd. | Elastic polyurethane fiber |
| JP5895312B2 (ja) * | 2011-05-27 | 2016-03-30 | 東レ・オペロンテックス株式会社 | 弾性布帛 |
-
1969
- 1969-06-26 SE SE09095/69A patent/SE359849B/xx unknown
- 1969-06-27 DK DK348569AA patent/DK123172B/da unknown
- 1969-06-30 BE BE735368D patent/BE735368A/xx unknown
- 1969-07-04 CH CH1022969A patent/CH514644A/de not_active IP Right Cessation
- 1969-07-07 LU LU59043D patent/LU59043A1/xx unknown
- 1969-07-09 US US840516A patent/US3635907A/en not_active Expired - Lifetime
- 1969-07-10 GB GB34862/69A patent/GB1263937A/en not_active Expired
- 1969-07-10 FR FR6923585A patent/FR2014588A1/fr not_active Withdrawn
- 1969-07-10 NL NL6910606A patent/NL6910606A/xx unknown
- 1969-07-11 CA CA056854A patent/CA928446A/en not_active Expired
- 1969-07-11 FI FI692072A patent/FI50991C/fi active
- 1969-07-11 AT AT666169A patent/AT296609B/de not_active IP Right Cessation
- 1969-07-12 JP JP44054844A patent/JPS4825433B1/ja active Pending
- 1969-07-12 ES ES369457A patent/ES369457A1/es not_active Expired
- 1969-07-14 NO NO2943/69A patent/NO125591B/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4825433B1 (xx) | 1973-07-28 |
| FI50991C (fi) | 1976-09-10 |
| LU59043A1 (xx) | 1969-11-18 |
| DK123172B (da) | 1972-05-23 |
| SE359849B (xx) | 1973-09-10 |
| DE1770884B2 (de) | 1977-02-03 |
| CA928446A (en) | 1973-06-12 |
| DE1770884A1 (de) | 1972-01-13 |
| FI50991B (xx) | 1976-05-31 |
| FR2014588A1 (xx) | 1970-04-17 |
| CH514644A (de) | 1971-10-31 |
| GB1263937A (en) | 1972-02-16 |
| BE735368A (xx) | 1969-12-01 |
| NL6910606A (xx) | 1970-01-15 |
| AT296609B (de) | 1972-02-25 |
| ES369457A1 (es) | 1971-06-01 |
| US3635907A (en) | 1972-01-18 |
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