DE1694842B2 - Stabilisierung von Lösungen von Polyurethan-Polyharnstoffpolymeren - Google Patents
Stabilisierung von Lösungen von Polyurethan-PolyharnstoffpolymerenInfo
- Publication number
- DE1694842B2 DE1694842B2 DE1694842A DE1694842A DE1694842B2 DE 1694842 B2 DE1694842 B2 DE 1694842B2 DE 1694842 A DE1694842 A DE 1694842A DE 1694842 A DE1694842 A DE 1694842A DE 1694842 B2 DE1694842 B2 DE 1694842B2
- Authority
- DE
- Germany
- Prior art keywords
- betaine
- solutions
- dimethylformamide
- polyurethane
- linear
- 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.)
- Granted
Links
- 229920000642 polymer Polymers 0.000 title claims description 12
- 229920002396 Polyurea Polymers 0.000 title description 4
- 230000006641 stabilisation Effects 0.000 title description 2
- 238000011105 stabilization Methods 0.000 title description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 37
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 13
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical class C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 13
- 229920000728 polyester Polymers 0.000 claims description 7
- 125000005442 diisocyanate group Chemical group 0.000 claims description 5
- 229920000570 polyether Polymers 0.000 claims description 5
- YKXUOESQDCXGIW-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;2-(trimethylazaniumyl)acetate Chemical compound C[N+](C)(C)CC(O)=O.OC(=O)CC(O)(C(O)=O)CC([O-])=O YKXUOESQDCXGIW-UHFFFAOYSA-N 0.000 claims description 4
- 229960002609 betaine citrate Drugs 0.000 claims description 4
- 150000004985 diamines Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- GFEOHZQDQDLTSZ-RXSVEWSESA-N carboxymethyl(trimethyl)azanium;(2r)-2-[(1s)-1,2-dihydroxyethyl]-3-hydroxy-5-oxo-2h-furan-4-olate Chemical compound C[N+](C)(C)CC(O)=O.OC[C@H](O)[C@H]1OC(=O)C([O-])=C1O GFEOHZQDQDLTSZ-RXSVEWSESA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 2
- 108090000623 proteins and genes Proteins 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 4
- -1 cyclic dicarboxylic acids Chemical class 0.000 claims 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- XKXPBJBODVHDAW-UHFFFAOYSA-N 4-(4-amino-2-chlorophenyl)-3-chloroaniline Chemical compound ClC1=CC(N)=CC=C1C1=CC=C(N)C=C1Cl XKXPBJBODVHDAW-UHFFFAOYSA-N 0.000 claims 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims 1
- BWLKKFSDKDJGDZ-UHFFFAOYSA-N [isocyanato(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(N=C=O)C1=CC=CC=C1 BWLKKFSDKDJGDZ-UHFFFAOYSA-N 0.000 claims 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000007334 copolymerization reaction Methods 0.000 claims 1
- 239000007822 coupling agent Substances 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 claims 1
- 150000001991 dicarboxylic acids Chemical class 0.000 claims 1
- 150000002009 diols Chemical class 0.000 claims 1
- 239000000835 fiber Substances 0.000 claims 1
- 239000000499 gel Substances 0.000 claims 1
- 150000002429 hydrazines Chemical class 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 238000006068 polycondensation reaction Methods 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims 1
- 229960001860 salicylate Drugs 0.000 claims 1
- 238000004513 sizing Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N xylylenediamine group Chemical group C=1(C(=CC=CC1)CN)CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 238000001879 gelation Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 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 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 229960003237 betaine Drugs 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 2
- CFXSFDXXYYHZFU-UHFFFAOYSA-N 2-hydroxybenzoic acid;2-(trimethylazaniumyl)acetate Chemical compound C[N+](C)(C)CC(O)=O.OC(=O)C1=CC=CC=C1[O-] CFXSFDXXYYHZFU-UHFFFAOYSA-N 0.000 description 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
- 241000282320 Panthera leo Species 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
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940041488 betaine salicylate Drugs 0.000 description 1
- 238000012412 chemical coupling Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000006855 networking Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/19—Quaternary ammonium compounds
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)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR44501A FR1469203A (fr) | 1965-12-31 | 1965-12-31 | Stabilisation de solutions de polymères polyuréthannes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1694842A1 DE1694842A1 (de) | 1970-10-29 |
| DE1694842B2 true DE1694842B2 (de) | 1974-02-21 |
| DE1694842C3 DE1694842C3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-10-17 |
Family
ID=8597475
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1694842A Granted DE1694842B2 (de) | 1965-12-31 | 1966-12-31 | Stabilisierung von Lösungen von Polyurethan-Polyharnstoffpolymeren |
Country Status (6)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3880784A (en) * | 1973-12-21 | 1975-04-29 | Bayer Ag | Solutions of diisocyanate polyaddition products which contain free semiacetals and which are stable in storage |
| US3987223A (en) * | 1972-12-23 | 1976-10-19 | Bayer Aktiengesellschaft | Method of dressing leather |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3005793A (en) * | 1961-10-24 | Olefin polymer and a betaine com- | ||
| BE574488A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1958-01-09 |
-
1965
- 1965-12-31 FR FR44501A patent/FR1469203A/fr not_active Expired
-
1966
- 1966-12-19 US US602594A patent/US3484404A/en not_active Expired - Lifetime
- 1966-12-23 NL NL6618132A patent/NL6618132A/xx unknown
- 1966-12-30 GB GB58417/66A patent/GB1099751A/en not_active Expired
- 1966-12-30 BE BE692052D patent/BE692052A/xx unknown
- 1966-12-31 DE DE1694842A patent/DE1694842B2/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US3484404A (en) | 1969-12-16 |
| BE692052A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-06-30 |
| FR1469203A (fr) | 1967-02-10 |
| DE1694842C3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-10-17 |
| GB1099751A (en) | 1968-01-17 |
| DE1694842A1 (de) | 1970-10-29 |
| NL6618132A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-07-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |