CA1162338A - Process for the preparation of nitrogen-containing condensates, and their use - Google Patents
Process for the preparation of nitrogen-containing condensates, and their useInfo
- Publication number
- CA1162338A CA1162338A CA000357446A CA357446A CA1162338A CA 1162338 A CA1162338 A CA 1162338A CA 000357446 A CA000357446 A CA 000357446A CA 357446 A CA357446 A CA 357446A CA 1162338 A CA1162338 A CA 1162338A
- Authority
- CA
- Canada
- Prior art keywords
- weight
- parts
- water
- aqueous solution
- reaction
- 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
- 238000000034 method Methods 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims description 13
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title description 10
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 32
- 229920000962 poly(amidoamine) Polymers 0.000 claims abstract description 29
- 239000007864 aqueous solution Substances 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 239000003960 organic solvent Substances 0.000 claims abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical group C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 12
- 230000014759 maintenance of location Effects 0.000 claims description 8
- 239000008394 flocculating agent Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000000306 component Substances 0.000 claims 1
- 239000012970 tertiary amine catalyst Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000007795 chemical reaction product Substances 0.000 abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 3
- 229920000768 polyamine Polymers 0.000 abstract description 3
- 150000003512 tertiary amines Chemical class 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract 1
- 229920001281 polyalkylene Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 description 41
- 229920005989 resin Polymers 0.000 description 41
- 239000000203 mixture Substances 0.000 description 23
- 239000000243 solution Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
- 229920001223 polyethylene glycol Polymers 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 239000002202 Polyethylene glycol Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 12
- 238000004132 cross linking Methods 0.000 description 12
- 229920000151 polyglycol Polymers 0.000 description 11
- 239000010695 polyglycol Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 229960005419 nitrogen Drugs 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000013543 active substance Substances 0.000 description 9
- 238000009833 condensation Methods 0.000 description 9
- 230000005494 condensation Effects 0.000 description 9
- 150000002170 ethers Chemical class 0.000 description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- 235000019253 formic acid Nutrition 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000001361 adipic acid Substances 0.000 description 6
- 235000011037 adipic acid Nutrition 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 230000001133 acceleration Effects 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- 230000008030 elimination Effects 0.000 description 4
- 238000003379 elimination reaction Methods 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 229940068917 polyethylene glycols Drugs 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229940037003 alum Drugs 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- -1 bis-chlorocarbonic acid ester Chemical class 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000003421 catalytic decomposition reaction Methods 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 description 1
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 1
- ZAXCZCOUDLENMH-UHFFFAOYSA-N 3,3,3-tetramine Chemical compound NCCCNCCCNCCCN ZAXCZCOUDLENMH-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000000332 continued effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229920002681 hypalon Polymers 0.000 description 1
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001521 polyalkylene glycol ether Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/48—Polymers modified by chemical after-treatment
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Separation By Low-Temperature Treatments (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Iron Core Of Rotating Electric Machines (AREA)
- Glass Compositions (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792934854 DE2934854A1 (de) | 1979-08-29 | 1979-08-29 | Verfahren zur herstellung von stickstoffhaltigen kondensationsprodukten und deren verwendung |
| DEP2934854.7 | 1979-08-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1162338A true CA1162338A (en) | 1984-02-14 |
Family
ID=6079538
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000357446A Expired CA1162338A (en) | 1979-08-29 | 1980-07-31 | Process for the preparation of nitrogen-containing condensates, and their use |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4371674A (cg-RX-API-DMAC10.html) |
| EP (1) | EP0025515B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JPS5634730A (cg-RX-API-DMAC10.html) |
| AT (1) | ATE4062T1 (cg-RX-API-DMAC10.html) |
| AU (1) | AU6182880A (cg-RX-API-DMAC10.html) |
| CA (1) | CA1162338A (cg-RX-API-DMAC10.html) |
| DE (2) | DE2934854A1 (cg-RX-API-DMAC10.html) |
| ES (1) | ES8104340A1 (cg-RX-API-DMAC10.html) |
| FI (1) | FI66015C (cg-RX-API-DMAC10.html) |
| NO (1) | NO152374C (cg-RX-API-DMAC10.html) |
| ZA (1) | ZA805326B (cg-RX-API-DMAC10.html) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3111713A1 (de) * | 1981-03-25 | 1982-10-07 | Basf Ag, 6700 Ludwigshafen | Wasserloesliche benzylierte polyamidoamine |
| DE3413566A1 (de) * | 1984-04-11 | 1985-10-24 | Bayer Ag, 5090 Leverkusen | Polyetheramine |
| EP0220960B1 (en) * | 1985-10-28 | 1992-08-26 | Sumitomo Chemical Company, Limited | Production of urea-polyamine resins for paper coating compositions |
| US5773507A (en) * | 1995-08-25 | 1998-06-30 | Henkel Corporation | Anti-static composition and process for making same |
| US6042691A (en) * | 1998-12-08 | 2000-03-28 | Plasmine Technology, Inc. | Cationic dispersions of fortified and modified rosins for use as paper sizing agents |
| US6677289B1 (en) * | 1999-07-16 | 2004-01-13 | The Procter & Gamble Company | Laundry detergent compositions comprising polyamines and mid-chain branched surfactants |
| EP1196524B1 (en) | 1999-07-16 | 2006-12-20 | The Procter & Gamble Company | Laundry detergent compositions comprising zwitterionic polyamines and mid-chain branched surfactants |
| US6696401B1 (en) * | 1999-11-09 | 2004-02-24 | The Procter & Gamble Company | Laundry detergent compositions comprising zwitterionic polyamines |
| WO2003043670A1 (en) | 2001-11-21 | 2003-05-30 | Basf Aktiengesellschaft | Crosslinked polyamine coating on superabsorbent hydrogels |
| AU2003268193A1 (en) * | 2002-08-30 | 2004-03-19 | The Procter And Gamble Company | Detergent compositions comprising hydrophobically modified polyamines |
| CA2494131C (en) * | 2002-09-12 | 2013-03-19 | The Procter & Gamble Company | Polymer systems and cleaning compositions comprising same |
| EP1699848A1 (en) * | 2003-12-19 | 2006-09-13 | The Procter and Gamble Company | Hydrophobic polyamine ethoxylates |
| DE102004005010A1 (de) | 2004-01-30 | 2005-08-18 | Basf Ag | Polymer für die Behandlung von Oberflächen |
| ES2337914T3 (es) | 2005-11-09 | 2010-04-30 | Ecolab Inc. | Composicion con propiedades de modificacion de superficie. |
| BRPI0712962B1 (pt) | 2006-06-20 | 2018-04-03 | Reckitt Benckiser Llc | Blocos de tratamento sólidos aperfeiçoados para utensílios sanitários |
| FR2902799B1 (fr) | 2006-06-27 | 2012-10-26 | Millipore Corp | Procede et unite de preparation d'un echantillon pour l'analyse microbiologique d'un liquide |
| WO2008079280A1 (en) * | 2006-12-21 | 2008-07-03 | Millipore Corporation | Purification of proteins |
| US8569464B2 (en) | 2006-12-21 | 2013-10-29 | Emd Millipore Corporation | Purification of proteins |
| US8362217B2 (en) | 2006-12-21 | 2013-01-29 | Emd Millipore Corporation | Purification of proteins |
| EP2014723A1 (de) | 2007-07-11 | 2009-01-14 | Basf Se | Verfahren zur Herstellung von Korkformkörpern |
| MY150256A (en) | 2007-12-18 | 2013-12-31 | Basf Se | Thermoplastic polyamides having polyether amines |
| WO2009151514A1 (en) * | 2008-06-11 | 2009-12-17 | Millipore Corporation | Stirred tank bioreactor |
| DE102008058246A1 (de) | 2008-11-19 | 2010-05-20 | Basf Se | Hochmolekulare Polyamide |
| KR101662343B1 (ko) | 2008-12-16 | 2016-10-04 | 바스프 에스이 | 열 노화 내성 폴리아미드 |
| DK2370561T3 (da) | 2008-12-16 | 2019-10-21 | Emd Millipore Corp | Omrøringstankreaktor og fremgangsmåde |
| DE102010062538A1 (de) | 2009-12-17 | 2011-06-22 | Basf Se, 67063 | Verfahren zur Herstellung geschweisster Formkörper aus Polyamid-6.10 |
| EP3597671B1 (en) | 2010-05-17 | 2022-09-21 | EMD Millipore Corporation | Stimulus responsive polymers for the purification of biomolecules |
| US9296896B2 (en) | 2010-11-23 | 2016-03-29 | Basf Se | Polyamides with nanoparticles on the surface |
| ES2525443T3 (es) | 2010-11-23 | 2014-12-23 | Basf Se | Poliamidas con partículas de tamaño nanométrico sobre la superficie |
| CN103443204A (zh) | 2011-01-18 | 2013-12-11 | 巴斯夫欧洲公司 | 热塑性模塑组合物 |
| EP2570448A1 (de) | 2011-09-13 | 2013-03-20 | Basf Se | Verwendung von Polyethyleniminen in der Herstellung von Polyamiden |
| US9486981B2 (en) | 2011-09-13 | 2016-11-08 | Basf Se | Use of polyethyleneimines in the preparation of polyamides |
| EP2782964B1 (de) | 2011-11-25 | 2018-04-11 | Basf Se | Blasformbare polyamidformmassen |
| US10583595B2 (en) | 2013-08-21 | 2020-03-10 | Basf Se | Method for producing a composite plastic part (CK) |
| EP3036275B1 (de) | 2013-08-21 | 2018-03-07 | Basf Se | Compositkunststoffteil mit verbesserter adhäsion zwischen den enthaltenen kunststoffkomponenten |
| KR102224391B1 (ko) | 2013-08-21 | 2021-03-08 | 바스프 에스이 | 열적 노화에 대한 개선된 저항을 갖는 플라스틱 복합 부품 |
| PL3039109T3 (pl) | 2013-08-26 | 2018-01-31 | Procter & Gamble | Kompozycje zawierające alkoksylowane poliaminy o niskiej temperaturze topnienia |
| US11332616B2 (en) * | 2017-08-24 | 2022-05-17 | Nippon Shokubai Co., Ltd. | Ethyleneimine polymer solution and method for producing same |
| WO2021191209A1 (en) | 2020-03-25 | 2021-09-30 | Basf Se | Heat-aging resistant polyamide molding compositions |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1135645A (en) * | 1965-03-24 | 1968-12-04 | Prec Processes Textiles Ltd | Modified water-soluble polyamides and substrates treated therewith |
| US3442975A (en) * | 1967-01-11 | 1969-05-06 | Allied Chem | Polyimine/polycarbonamide graft polymers |
| DE1802435C3 (de) * | 1968-10-11 | 1979-01-18 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von vernetzten Harzen auf der Basis von basischen Polyamidoaminen und deren Verwendung als Entwässerungs-, Retentions- und Flockungsmittel bei der Papierherstellung |
| US4277581A (en) * | 1973-11-30 | 1981-07-07 | L'oreal | Polyamino-polyamide crosslinked with crosslinking agent |
| DE2434816C3 (de) * | 1974-07-19 | 1981-01-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von stickstoffhaltigen Kondensationsprodukten und deren Verwendung als Retentionsmittel, Flockungsmittel und Entwässerungsbeschleuniger bei der Papierherstellung |
| US4144123A (en) * | 1974-07-19 | 1979-03-13 | Basf Aktiengesellschaft | Incorporating a crosslinked polyamidoamine condensation product into paper-making pulp |
| GB1508511A (en) | 1975-06-05 | 1978-04-26 | Gaf Corp | Polyoxyethylene glycol dihalides |
| DE2756431C2 (de) * | 1977-12-17 | 1985-05-15 | Bayer Ag, 5090 Leverkusen | Amidgruppenhaltige Polyamine |
-
1979
- 1979-08-29 DE DE19792934854 patent/DE2934854A1/de not_active Withdrawn
-
1980
- 1980-07-30 US US06/173,479 patent/US4371674A/en not_active Expired - Lifetime
- 1980-07-31 CA CA000357446A patent/CA1162338A/en not_active Expired
- 1980-08-14 AT AT80104825T patent/ATE4062T1/de not_active IP Right Cessation
- 1980-08-14 EP EP80104825A patent/EP0025515B1/de not_active Expired
- 1980-08-14 DE DE8080104825T patent/DE3064043D1/de not_active Expired
- 1980-08-19 FI FI802619A patent/FI66015C/fi not_active IP Right Cessation
- 1980-08-28 NO NO802543A patent/NO152374C/no unknown
- 1980-08-28 JP JP11785880A patent/JPS5634730A/ja active Granted
- 1980-08-28 ES ES494567A patent/ES8104340A1/es not_active Expired
- 1980-08-28 AU AU61828/80A patent/AU6182880A/en not_active Abandoned
- 1980-08-28 ZA ZA00805326A patent/ZA805326B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0025515A1 (de) | 1981-03-25 |
| ATE4062T1 (de) | 1983-07-15 |
| DE2934854A1 (de) | 1981-09-10 |
| AU6182880A (en) | 1981-03-05 |
| US4371674A (en) | 1983-02-01 |
| ES494567A0 (es) | 1981-04-01 |
| ZA805326B (en) | 1981-10-28 |
| NO152374C (no) | 1985-09-18 |
| FI802619A7 (fi) | 1981-03-01 |
| ES8104340A1 (es) | 1981-04-01 |
| FI66015B (fi) | 1984-04-30 |
| FI66015C (fi) | 1984-08-10 |
| EP0025515B1 (de) | 1983-07-06 |
| NO802543L (no) | 1981-03-02 |
| DE3064043D1 (en) | 1983-08-11 |
| JPS6351177B2 (cg-RX-API-DMAC10.html) | 1988-10-13 |
| NO152374B (no) | 1985-06-10 |
| JPS5634730A (en) | 1981-04-07 |
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| MKEX | Expiry |