DE69832382T2 - Vernetzte reaktionsprodukte von alkoxylierten alkoholen und alkylenglycolen - Google Patents
Vernetzte reaktionsprodukte von alkoxylierten alkoholen und alkylenglycolen Download PDFInfo
- Publication number
- DE69832382T2 DE69832382T2 DE69832382T DE69832382T DE69832382T2 DE 69832382 T2 DE69832382 T2 DE 69832382T2 DE 69832382 T DE69832382 T DE 69832382T DE 69832382 T DE69832382 T DE 69832382T DE 69832382 T2 DE69832382 T2 DE 69832382T2
- Authority
- DE
- Germany
- Prior art keywords
- range
- group
- component
- iii
- product
- 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 - Fee Related
Links
- 239000007795 chemical reaction product Substances 0.000 title claims description 12
- 150000001298 alcohols Chemical class 0.000 title description 2
- 150000002334 glycols Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- -1 ethyleneoxy, 1,2-propyleneoxy Chemical group 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 239000003973 paint Substances 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 239000006184 cosolvent Substances 0.000 claims description 8
- 229920000126 latex Polymers 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 7
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 7
- 239000004816 latex Substances 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 230000008719 thickening Effects 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 239000006185 dispersion Substances 0.000 claims description 3
- 125000003700 epoxy group Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000005292 vacuum distillation Methods 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 238000010533 azeotropic distillation Methods 0.000 claims 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 239000002562 thickening agent Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229920002594 Polyethylene Glycol 8000 Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- COBPKKZHLDDMTB-UHFFFAOYSA-N 2-[2-(2-butoxyethoxy)ethoxy]ethanol Chemical compound CCCCOCCOCCOCCO COBPKKZHLDDMTB-UHFFFAOYSA-N 0.000 description 3
- 239000004908 Emulsion polymer Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- CFXQEHVMCRXUSD-UHFFFAOYSA-N 1,2,3-Trichloropropane Chemical compound ClCC(Cl)CCl CFXQEHVMCRXUSD-UHFFFAOYSA-N 0.000 description 2
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000007046 ethoxylation reaction Methods 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 229920001515 polyalkylene glycol Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 229940087291 tridecyl alcohol Drugs 0.000 description 2
- 239000004034 viscosity adjusting agent Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- PIQHRAXKAGNHCM-UHFFFAOYSA-N 1,2,4-trichlorobutane Chemical compound ClCCC(Cl)CCl PIQHRAXKAGNHCM-UHFFFAOYSA-N 0.000 description 1
- ZBWULYMJRMOQSX-UHFFFAOYSA-N 1,3,6-trichlorohexane Chemical compound ClCCCC(Cl)CCCl ZBWULYMJRMOQSX-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 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
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 238000009991 scouring Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D19/00—Degasification of liquids
- B01D19/02—Foam dispersion or prevention
- B01D19/04—Foam dispersion or prevention by addition of chemical substances
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D19/00—Degasification of liquids
- B01D19/02—Foam dispersion or prevention
- B01D19/04—Foam dispersion or prevention by addition of chemical substances
- B01D19/0404—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance
- B01D19/0431—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance containing 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
- 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
- C08G65/04—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 only
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
- C08G65/24—Epihalohydrins
-
- 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
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/337—Polymers modified by chemical after-treatment with organic compounds containing other elements
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Toxicology (AREA)
- Dispersion Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Paints Or Removers (AREA)
- Polyethers (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4933897P | 1997-06-10 | 1997-06-10 | |
| US49338P | 1997-06-10 | ||
| US911795 | 1997-08-15 | ||
| US08/911,795 US5877245A (en) | 1997-06-10 | 1997-08-15 | Cross-linked reaction products of alkoxylated alcohols and alkylene glycols |
| PCT/US1998/011393 WO1998056851A1 (en) | 1997-06-10 | 1998-06-10 | Cross-linked reaction products of alkoxylated alcohols and alkylene glycols |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69832382D1 DE69832382D1 (de) | 2005-12-22 |
| DE69832382T2 true DE69832382T2 (de) | 2006-06-08 |
Family
ID=26727083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69832382T Expired - Fee Related DE69832382T2 (de) | 1997-06-10 | 1998-06-10 | Vernetzte reaktionsprodukte von alkoxylierten alkoholen und alkylenglycolen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5877245A (enExample) |
| EP (1) | EP0988339B1 (enExample) |
| JP (1) | JP2002503285A (enExample) |
| AU (1) | AU743732B2 (enExample) |
| DE (1) | DE69832382T2 (enExample) |
| ES (1) | ES2251086T3 (enExample) |
| WO (1) | WO1998056851A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6110977A (en) * | 1997-01-14 | 2000-08-29 | Henkel Corporation | Alkyl polyglycoside compositions having reduced viscosity and inhibited crystallization |
| US6387962B1 (en) * | 1997-06-10 | 2002-05-14 | Cognis Corporation | Defoamers for aqueous systems |
| US6172123B1 (en) | 1999-07-30 | 2001-01-09 | Henkel Corporation | Demulsifiers for separating oil and water mixtures |
| US6465605B2 (en) * | 2000-02-16 | 2002-10-15 | Cognis Corporation | Branched polymeric surfactant reaction products, methods for their preparation, and uses therefor |
| US6512016B2 (en) | 2000-08-17 | 2003-01-28 | Cognis Corporation | Compositions for defoaming aqueous compositions |
| US6540942B2 (en) | 2000-11-09 | 2003-04-01 | Cognis Corporation | Nonaqueous compositions and additives therefor |
| US6572691B2 (en) * | 2001-10-01 | 2003-06-03 | Cognis Corporation | Ink compositions and methods of use therefor |
| US7247606B2 (en) * | 2001-11-05 | 2007-07-24 | Cognis Corporation | Branched reaction products |
| JP3910530B2 (ja) * | 2002-12-16 | 2007-04-25 | 花王株式会社 | 汚れ放出剤 |
| US20040237841A1 (en) * | 2003-01-29 | 2004-12-02 | Brown David W. | Nonaqueous spray applied compositions and methods for applying them |
| US7169858B2 (en) * | 2003-02-27 | 2007-01-30 | Cognis Corporation | Polyfluorinated compounds useful as surfactants, foam control agents and/or rheology modifiers |
| US7803864B2 (en) | 2006-01-05 | 2010-09-28 | Rohm And Haas Company | Associative thickener compositions and methods of use |
| US8119717B2 (en) * | 2006-11-21 | 2012-02-21 | Basf Corporation | Coating composition having a low volatile organic compound content |
| US20080161535A1 (en) * | 2006-12-21 | 2008-07-03 | Wiggins Michael S | Thickening and wetting agents |
| US8431639B2 (en) * | 2007-11-08 | 2013-04-30 | Basf Corporation | Wetting additive and composition including the same |
| EP2247357A1 (en) * | 2008-02-27 | 2010-11-10 | Cognis IP Management GmbH | Defoaming coalescents |
| US20120082629A1 (en) * | 2010-09-01 | 2012-04-05 | Basf Se | Associative Thickeners For Aqueous Preparations |
| US10982046B2 (en) * | 2014-07-10 | 2021-04-20 | Basf Se | Reaction products and use of same in defoamer compositions and methods for defoaming |
| PL3636691T3 (pl) | 2015-10-07 | 2021-09-27 | Elementis Specialties, Inc. | Środek zwilżający i przeciwpieniący |
| JP7655109B2 (ja) | 2021-06-18 | 2025-04-02 | Agc株式会社 | ポリオキシアルキレングリシジルエーテルの製造方法 |
| CN115850687A (zh) * | 2022-12-12 | 2023-03-28 | 江苏扬农锦湖化工有限公司 | 一种聚乙二醇二缩水甘油醚的制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL66998C (enExample) * | 1946-08-31 | |||
| US3770684A (en) * | 1970-06-25 | 1973-11-06 | Troy Chemical Corp | Latex compositions containing bodying agents |
| US4079028A (en) * | 1975-10-03 | 1978-03-14 | Rohm And Haas Company | Polyurethane thickeners in latex compositions |
| US4426485A (en) * | 1982-06-14 | 1984-01-17 | Union Carbide Corporation | Polymers with hydrophobe bunches |
| US4855403A (en) * | 1983-02-22 | 1989-08-08 | Union Carbide Corporation | Connected branch copolymers, methods for their production, and copying materials including same |
| DE4040466C2 (de) * | 1990-12-18 | 1995-03-09 | Basf Ag | Hochmolekulare Polyetherpolyole |
| EP0703940B1 (en) * | 1993-05-27 | 2001-11-07 | Cognis Corporation | Polymeric thickeners for aqueous compositions |
| WO1997021743A1 (en) * | 1995-12-08 | 1997-06-19 | Henkel Corporation | Polymeric thickeners for aqueous compositions |
| US5916935A (en) * | 1996-08-27 | 1999-06-29 | Henkel Corporation | Polymeric thickeners for aqueous compositions |
-
1997
- 1997-08-15 US US08/911,795 patent/US5877245A/en not_active Expired - Lifetime
-
1998
- 1998-06-10 ES ES98928870T patent/ES2251086T3/es not_active Expired - Lifetime
- 1998-06-10 JP JP50280499A patent/JP2002503285A/ja not_active Ceased
- 1998-06-10 WO PCT/US1998/011393 patent/WO1998056851A1/en not_active Ceased
- 1998-06-10 DE DE69832382T patent/DE69832382T2/de not_active Expired - Fee Related
- 1998-06-10 AU AU80566/98A patent/AU743732B2/en not_active Ceased
- 1998-06-10 EP EP98928870A patent/EP0988339B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU8056698A (en) | 1998-12-30 |
| WO1998056851A1 (en) | 1998-12-17 |
| DE69832382D1 (de) | 2005-12-22 |
| EP0988339A1 (en) | 2000-03-29 |
| US5877245A (en) | 1999-03-02 |
| JP2002503285A (ja) | 2002-01-29 |
| AU743732B2 (en) | 2002-01-31 |
| ES2251086T3 (es) | 2006-04-16 |
| EP0988339A4 (en) | 2001-04-11 |
| EP0988339B1 (en) | 2005-11-16 |
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