DE2414470C3 - - Google Patents
Info
- Publication number
- DE2414470C3 DE2414470C3 DE19742414470 DE2414470A DE2414470C3 DE 2414470 C3 DE2414470 C3 DE 2414470C3 DE 19742414470 DE19742414470 DE 19742414470 DE 2414470 A DE2414470 A DE 2414470A DE 2414470 C3 DE2414470 C3 DE 2414470C3
- Authority
- DE
- Germany
- Prior art keywords
- water
- acid
- bisulfite
- solution
- blocked
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- LSNNMFCWUKXFEE-UHFFFAOYSA-M bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 10
- 229920001228 Polyisocyanate Polymers 0.000 claims description 8
- 239000005056 polyisocyanate Substances 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 6
- 239000004753 textile Substances 0.000 claims description 6
- 239000010985 leather Substances 0.000 claims description 5
- 239000000123 paper Substances 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000000243 solution Substances 0.000 description 18
- 239000007864 aqueous solution Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N P-Toluenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 239000002981 blocking agent Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N Hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 210000002268 Wool Anatomy 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- -1 their use Chemical compound 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-Propanediol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- BNNMDMGPZUOOOE-UHFFFAOYSA-N 4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.CC1=CC=C(S(O)(=O)=O)C=C1 BNNMDMGPZUOOOE-UHFFFAOYSA-N 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N Chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 2
- 229920001451 Polypropylene glycol Polymers 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atoms Chemical group C* 0.000 description 2
- 229940106681 chloroacetic acid Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 229960001367 tartaric acid Drugs 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- YMOKTQJGQCFJHR-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;formic acid Chemical compound OC=O.OC(=O)C(O)C(O)C(O)=O YMOKTQJGQCFJHR-UHFFFAOYSA-N 0.000 description 1
- AUHUWFIYJDRPJX-UHFFFAOYSA-N 4-hexylbenzenesulfonic acid Chemical compound CCCCCCC1=CC=C(S(O)(=O)=O)C=C1 AUHUWFIYJDRPJX-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N Benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- KDPAWGWELVVRCH-UHFFFAOYSA-N Bromoacetic acid Chemical compound OC(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-N 0.000 description 1
- 102000011782 Keratins Human genes 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229940099427 Potassium Bisulfite Drugs 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M Potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- WRUAHXANJKHFIL-UHFFFAOYSA-N benzene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(S(O)(=O)=O)=C1 WRUAHXANJKHFIL-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 230000000903 blocking Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940013688 formic acid Drugs 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 1
- 230000002209 hydrophobic Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 150000002989 phenols Chemical class 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
- 150000003112 potassium compounds Chemical class 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229940001607 sodium bisulfite Drugs 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742414470 DE2414470B2 (de) | 1974-03-26 | 1974-03-26 | Waessrige loesung eines bisulfitblockierten polyisocyanatvorpolymeren |
| CA222,540A CA1053824A (en) | 1974-03-26 | 1975-03-19 | Stabilized aqueous solution of a bisulphite blocked polyisocyanate |
| GB1138975A GB1453816A (en) | 1974-03-26 | 1975-03-19 | Aqueous solution of a bisulphite blocked polyisocyanate |
| US05/561,399 US3984365A (en) | 1974-03-26 | 1975-03-24 | Stabilized aqueous solution of a bisulphite blocked polyisocyanate |
| JP50035658A JPS5239720B2 (US20100056889A1-20100304-C00004.png) | 1974-03-26 | 1975-03-26 | |
| AU79518/75A AU483031B2 (en) | 1974-03-26 | 1975-03-26 | Aqueous solution ofa bisulphite blocked polyisocyanate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742414470 DE2414470B2 (de) | 1974-03-26 | 1974-03-26 | Waessrige loesung eines bisulfitblockierten polyisocyanatvorpolymeren |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2414470A1 DE2414470A1 (de) | 1975-10-23 |
| DE2414470B2 DE2414470B2 (de) | 1977-01-13 |
| DE2414470C3 true DE2414470C3 (US20100056889A1-20100304-C00004.png) | 1977-09-01 |
Family
ID=5911186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742414470 Granted DE2414470B2 (de) | 1974-03-26 | 1974-03-26 | Waessrige loesung eines bisulfitblockierten polyisocyanatvorpolymeren |
Country Status (5)
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA757452B (en) * | 1974-12-04 | 1976-11-24 | Commw Scient Ind Res Org | Stable concentrated polymer mixtures for the treatment of textile materials |
| US4144268A (en) * | 1976-02-11 | 1979-03-13 | Commonwealth Scientific And Industrial Research Organization | Preparation of bisulphite adducts of biruet-polyisocyanates |
| JPS5414926U (US20100056889A1-20100304-C00004.png) * | 1977-07-05 | 1979-01-31 | ||
| JPS5478633U (US20100056889A1-20100304-C00004.png) * | 1977-11-12 | 1979-06-04 | ||
| JPS5482726U (US20100056889A1-20100304-C00004.png) * | 1977-11-25 | 1979-06-12 | ||
| JPS5486541U (US20100056889A1-20100304-C00004.png) * | 1977-11-30 | 1979-06-19 | ||
| DE2837083A1 (de) * | 1978-08-24 | 1980-03-06 | Bayer Ag | Verfahren zur filzfreiausruestung von textilgut aus keratinhaltigen fasern |
| JPS5548716U (US20100056889A1-20100304-C00004.png) * | 1978-09-27 | 1980-03-31 | ||
| JPS5856580B2 (ja) * | 1980-04-25 | 1983-12-15 | 第一工業製薬株式会社 | 熱反応性ポリウレタンエマルジヨンの製造方法 |
| US4395444A (en) * | 1981-09-25 | 1983-07-26 | Ppg Industries, Inc. | Thermosetting cationic acrylic latex compositions containing blocked isocyanates |
| US4722969A (en) * | 1986-09-18 | 1988-02-02 | W. R. Grace & Co. | Storage stable, low temperature, solventless, curable urethane composition |
| DE3705687A1 (de) * | 1987-02-23 | 1988-09-01 | Boehringer Mannheim Gmbh | Polyurethanmodifizierte enzyme |
| JPS6414376A (en) * | 1988-03-29 | 1989-01-18 | Dai Ichi Kogyo Seiyaku Co Ltd | Method for improving abrasion strength of seat belt or sling belt |
| US5284918A (en) * | 1991-05-01 | 1994-02-08 | W. R. Grace & Co.-Conn. | One package polyurethane/thermoplast plastisol composition |
| TR200102760T2 (tr) * | 1999-03-29 | 2001-12-21 | Bayer Aktiengesellschaft | Tekstil muamele bileşimleri, hazırlanış ve kullanımları |
| DE19919816A1 (de) * | 1999-04-30 | 2000-11-02 | Rotta Gmbh | Wässrige Zusammensetzung zur Filzfreiausrüstung von Wolle |
| EP2540753A1 (de) * | 2011-06-29 | 2013-01-02 | LANXESS Deutschland GmbH | Zusammensetzung auf Basis Carbamoylsulfonatgruppen-haltiger Verbindungen |
| EP2726522A1 (de) | 2011-06-29 | 2014-05-07 | LANXESS Deutschland GmbH | Zusammensetzung auf basis carbamoylsulfonatgruppen-haltiger verbindungen |
| US9617402B2 (en) * | 2011-10-28 | 2017-04-11 | Basf Se | Process for preparing polyisocyanates which are flocculation-stable in solvents from (cyclo)aliphatic diisocyanates |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2746988A (en) * | 1956-05-22 | Isdcyanate-bisulefete al | ||
| BE501972A (US20100056889A1-20100304-C00004.png) * | 1950-03-21 | 1900-01-01 | ||
| US3491067A (en) * | 1967-07-12 | 1970-01-20 | Diamond Shamrock Corp | Alkylolated polyurethane resins derived from hydroxy ethyl carbamate and their use |
| BE795575A (fr) * | 1972-02-18 | 1973-06-18 | Commw Scient Ind Res Org | Procede de traitement de matieres keratiniques |
-
1974
- 1974-03-26 DE DE19742414470 patent/DE2414470B2/de active Granted
-
1975
- 1975-03-19 GB GB1138975A patent/GB1453816A/en not_active Expired
- 1975-03-19 CA CA222,540A patent/CA1053824A/en not_active Expired
- 1975-03-24 US US05/561,399 patent/US3984365A/en not_active Expired - Lifetime
- 1975-03-26 JP JP50035658A patent/JPS5239720B2/ja not_active Expired
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