DE2410862C3 - Ätherstrukturen enthaltende Dihydroxysulfonate und Verfahren zu deren Herstellung - Google Patents
Ätherstrukturen enthaltende Dihydroxysulfonate und Verfahren zu deren HerstellungInfo
- Publication number
- DE2410862C3 DE2410862C3 DE2410862A DE2410862A DE2410862C3 DE 2410862 C3 DE2410862 C3 DE 2410862C3 DE 2410862 A DE2410862 A DE 2410862A DE 2410862 A DE2410862 A DE 2410862A DE 2410862 C3 DE2410862 C3 DE 2410862C3
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- dihydroxysulfonates
- water
- preparation
- sulfonate
- 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
- 125000001033 ether group Chemical group 0.000 title claims description 5
- 238000000034 method Methods 0.000 title description 8
- 238000002360 preparation method Methods 0.000 title description 4
- 238000006243 chemical reaction Methods 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 229920002635 polyurethane Polymers 0.000 description 10
- 239000004814 polyurethane Substances 0.000 description 10
- 150000002009 diols Chemical class 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 8
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 8
- 239000011734 sodium Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- -1 alkali metal hydrogen sulfites Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 238000007664 blowing Methods 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ZSUFVLYCHJKOMD-UHFFFAOYSA-N 3-hydroxy-2-(hydroxymethyl)propane-1-sulfonic acid Chemical class OCC(CO)CS(O)(=O)=O ZSUFVLYCHJKOMD-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 238000007046 ethoxylation reaction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920003009 polyurethane dispersion Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CUUNWWCQMKJKRR-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol;hexanedioic acid;hexane-1,1-diol Chemical compound OCC(C)(C)CO.CCCCCC(O)O.OC(=O)CCCCC(O)=O CUUNWWCQMKJKRR-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004908 Emulsion polymer Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- FUVHVZKHVSRCKH-UHFFFAOYSA-N ethane-1,2-diol;hexanedioic acid;phthalic acid Chemical compound OCCO.OC(=O)CCCCC(O)=O.OC(=O)C1=CC=CC=C1C(O)=O FUVHVZKHVSRCKH-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- HWVUYETXPFMTHJ-UHFFFAOYSA-N hex-3-ene-1,1-diol Chemical compound CCC=CCC(O)O HWVUYETXPFMTHJ-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides 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
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
- C08G18/0828—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing sulfonate groups or groups forming them
-
- 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
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5072—Polyethers having heteroatoms other than oxygen containing sulfur
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/326—Polymers modified by chemical after-treatment with inorganic compounds containing sulfur
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/42—Polyamides containing atoms other than carbon, hydrogen, oxygen, and nitrogen
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/18—Homopolymers or copolymers of nitriles
- C08L33/20—Homopolymers or copolymers of acrylonitrile
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S260/00—Chemistry of carbon compounds
- Y10S260/15—Antistatic agents not otherwise provided for
- Y10S260/19—Non-high polymeric antistatic agents/n
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
- Polyesters Or Polycarbonates (AREA)
- Polyurethanes Or Polyureas (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2410862A DE2410862C3 (de) | 1974-03-07 | 1974-03-07 | Ätherstrukturen enthaltende Dihydroxysulfonate und Verfahren zu deren Herstellung |
| GB872375A GB1454977A (en) | 1974-03-07 | 1975-03-03 | Diols containing sulphonic acid groups based on dihydroxy alkenes |
| US05/555,228 US4048221A (en) | 1974-03-07 | 1975-03-04 | Diols containing sulphonic acid groups based on dihydroxy alkenes |
| NL7502549A NL7502549A (nl) | 1974-03-07 | 1975-03-04 | Diolen met sulfonzuurgroepen op basis van dihydroxyalkenen. |
| BE154012A BE826303A (fr) | 1974-03-07 | 1975-03-05 | Dihydroxysulfonates contenant des structures d'ethers et leur preparation |
| LU71967A LU71967A1 (enExample) | 1974-03-07 | 1975-03-05 | |
| IT48456/76A IT1032246B (it) | 1974-03-07 | 1975-03-05 | Solfonati contenenti strutture uietere e procedimento per produrli |
| JP50026572A JPS5839154B2 (ja) | 1974-03-07 | 1975-03-06 | ジヒドロキシアルケンオベ−ストスル スルホンサンキガンユウジオ−ルノセイゾウホウホウ |
| DK90875*#A DK90875A (enExample) | 1974-03-07 | 1975-03-06 | |
| IE481/75A IE40740B1 (en) | 1974-03-07 | 1975-03-06 | Diols containing sulphonic acid groups based on dihydroxy alkenes |
| ES435346A ES435346A1 (es) | 1974-03-07 | 1975-03-06 | Procedimiento para la obtencion de dihidroxisulfonatos con-teniendo estructuras eter. |
| FR7507255A FR2263235B1 (enExample) | 1974-03-07 | 1975-03-07 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2410862A DE2410862C3 (de) | 1974-03-07 | 1974-03-07 | Ätherstrukturen enthaltende Dihydroxysulfonate und Verfahren zu deren Herstellung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2410862A1 DE2410862A1 (de) | 1975-09-11 |
| DE2410862B2 DE2410862B2 (de) | 1980-04-17 |
| DE2410862C3 true DE2410862C3 (de) | 1980-12-11 |
Family
ID=5909348
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2410862A Expired DE2410862C3 (de) | 1974-03-07 | 1974-03-07 | Ätherstrukturen enthaltende Dihydroxysulfonate und Verfahren zu deren Herstellung |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4048221A (enExample) |
| JP (1) | JPS5839154B2 (enExample) |
| BE (1) | BE826303A (enExample) |
| DE (1) | DE2410862C3 (enExample) |
| DK (1) | DK90875A (enExample) |
| ES (1) | ES435346A1 (enExample) |
| FR (1) | FR2263235B1 (enExample) |
| GB (1) | GB1454977A (enExample) |
| IE (1) | IE40740B1 (enExample) |
| IT (1) | IT1032246B (enExample) |
| LU (1) | LU71967A1 (enExample) |
| NL (1) | NL7502549A (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2446440C3 (de) * | 1974-09-28 | 1981-04-30 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von wäßrigen Dispersionen von Sulfonatgruppen aufweisenden Polyurethanen |
| US4222957A (en) * | 1978-11-24 | 1980-09-16 | Texaco Development Corp. | Process of purifying ether sulfonates |
| DE3605765A1 (de) * | 1986-02-22 | 1987-08-27 | Ver Glaswerke Gmbh | Transparente deckschicht aus weichelastischem polyurethan fuer transparente glas- oder kunststoffsubstrate |
| DE3633421C1 (de) * | 1986-10-01 | 1987-07-23 | Goldschmidt Ag Th | Hydroxyl- und Sulfonatgruppen aufweisende Polyoxyalkylenether und deren Verwendung zur Herstellung von dispergierbaren Polyurethanen |
| JPS63103361U (enExample) * | 1986-12-26 | 1988-07-05 | ||
| US4774363A (en) * | 1987-10-16 | 1988-09-27 | Gaf Corporation | Metal derivatives of butenediol |
| DE4004883A1 (de) * | 1990-02-16 | 1991-08-22 | Basf Ag | Vinylpolyetheralkohole |
| US5278197A (en) * | 1993-07-06 | 1994-01-11 | Miles Inc. | Soft, flexible polyurethane foam |
| WO2007037466A1 (en) * | 2005-09-29 | 2007-04-05 | Nippon Shokubai Co., Ltd. | Hydrophilized polyalkylene glycol, production method thereof, and application thereof |
| CN108329413B (zh) * | 2017-01-20 | 2019-08-30 | 中国科学院化学研究所 | 一种聚乙烯醇磺酸盐及其合成方法、印刷用亲水版和应用以及印刷版 |
| JP6645525B2 (ja) | 2018-02-23 | 2020-02-14 | 株式会社明電舎 | 試験システムの制御装置 |
| CN114230728A (zh) * | 2021-12-16 | 2022-03-25 | 北京市建筑工程研究院有限责任公司 | 一种聚羧酸减水剂及其制备方法 |
| CN114106262B (zh) * | 2021-12-16 | 2022-11-04 | 北京市建筑工程研究院有限责任公司 | 一种聚羧酸保坍剂及其制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2602054A (en) * | 1950-09-25 | 1952-07-01 | Petrolite Corp | Process for breaking petroleum emulsions |
| US3002903A (en) * | 1958-09-26 | 1961-10-03 | Hanson Van Winkle Munning Co | Electrodeposition of nickel |
| US3041256A (en) * | 1960-07-12 | 1962-06-26 | Hanson Van Winkle Munning Co | Electrodeposition of nickel |
| NL279927A (enExample) * | 1961-06-20 | |||
| US3418239A (en) * | 1965-12-03 | 1968-12-24 | Mobil Oil Corp | Oil well waterflooding method |
| US3860638A (en) * | 1971-05-20 | 1975-01-14 | Inorganic & Metal Treating Che | Bright nickel plating bath addition agents |
-
1974
- 1974-03-07 DE DE2410862A patent/DE2410862C3/de not_active Expired
-
1975
- 1975-03-03 GB GB872375A patent/GB1454977A/en not_active Expired
- 1975-03-04 NL NL7502549A patent/NL7502549A/xx not_active Application Discontinuation
- 1975-03-04 US US05/555,228 patent/US4048221A/en not_active Expired - Lifetime
- 1975-03-05 BE BE154012A patent/BE826303A/xx not_active IP Right Cessation
- 1975-03-05 LU LU71967A patent/LU71967A1/xx unknown
- 1975-03-05 IT IT48456/76A patent/IT1032246B/it active
- 1975-03-06 JP JP50026572A patent/JPS5839154B2/ja not_active Expired
- 1975-03-06 DK DK90875*#A patent/DK90875A/da unknown
- 1975-03-06 IE IE481/75A patent/IE40740B1/xx unknown
- 1975-03-06 ES ES435346A patent/ES435346A1/es not_active Expired
- 1975-03-07 FR FR7507255A patent/FR2263235B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| LU71967A1 (enExample) | 1976-02-04 |
| FR2263235A1 (enExample) | 1975-10-03 |
| BE826303A (fr) | 1975-09-05 |
| JPS5839154B2 (ja) | 1983-08-27 |
| DE2410862B2 (de) | 1980-04-17 |
| IE40740B1 (en) | 1979-08-01 |
| FR2263235B1 (enExample) | 1980-02-22 |
| GB1454977A (en) | 1976-11-10 |
| JPS50121226A (enExample) | 1975-09-23 |
| DK90875A (enExample) | 1975-09-08 |
| IE40740L (en) | 1975-09-07 |
| IT1032246B (it) | 1979-05-30 |
| US4048221A (en) | 1977-09-13 |
| DE2410862A1 (de) | 1975-09-11 |
| ES435346A1 (es) | 1976-12-16 |
| NL7502549A (nl) | 1975-09-09 |
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Legal Events
| Date | Code | Title | Description |
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| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |