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)
- Separation By Low-Temperature Treatments (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Iron Core Of Rotating Electric Machines (AREA)
- Glass Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (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 (enExample) |
| EP (1) | EP0025515B1 (enExample) |
| JP (1) | JPS5634730A (enExample) |
| AT (1) | ATE4062T1 (enExample) |
| AU (1) | AU6182880A (enExample) |
| CA (1) | CA1162338A (enExample) |
| DE (2) | DE2934854A1 (enExample) |
| ES (1) | ES8104340A1 (enExample) |
| FI (1) | FI66015C (enExample) |
| NO (1) | NO152374C (enExample) |
| ZA (1) | ZA805326B (enExample) |
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 |
| DE3686547T2 (de) * | 1985-10-28 | 1993-03-25 | Sumitomo Chemical Co | Herstellung von harnstoff-polyaminharzen fuer papierbekleidungszusammensetzungen. |
| 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 |
| AU6093500A (en) | 1999-07-16 | 2001-02-05 | Procter & Gamble Company, The | Laundry detergent compositions comprising zwitterionic polyamines and mid-chain branched surfactants |
| US6677289B1 (en) * | 1999-07-16 | 2004-01-13 | The Procter & Gamble Company | Laundry detergent compositions comprising polyamines and mid-chain branched surfactants |
| US6696401B1 (en) * | 1999-11-09 | 2004-02-24 | The Procter & Gamble Company | Laundry detergent compositions comprising zwitterionic polyamines |
| AU2002352016A1 (en) | 2001-11-21 | 2003-06-10 | Basf Aktiengesellschaft | Crosslinked polyamine coating on superabsorbent hydrogels |
| WO2004020563A1 (en) * | 2002-08-30 | 2004-03-11 | The Procter & Gamble Company | Detergent compositions comprising hydrophobically modified polyamines |
| CN1681913A (zh) * | 2002-09-12 | 2005-10-12 | 宝洁公司 | 聚合物体系及包含同样物质的清洁组合物 |
| MXPA06007022A (es) * | 2003-12-19 | 2006-08-31 | Procter & Gamble | Etoxilatos de poliamina hidrofobica. |
| DE102004005010A1 (de) | 2004-01-30 | 2005-08-18 | Basf Ag | Polymer für die Behandlung von Oberflächen |
| EP1945746B1 (en) | 2005-11-09 | 2010-02-10 | Ecolab Inc. | Composition with surface modifying properties |
| 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 |
| US8569464B2 (en) | 2006-12-21 | 2013-10-29 | Emd Millipore Corporation | Purification of proteins |
| WO2008079280A1 (en) * | 2006-12-21 | 2008-07-03 | 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 |
| ES2373007T3 (es) | 2007-12-18 | 2012-01-30 | Basf Se | Poliamidas termoplásticas con poliéter aminas. |
| US8999702B2 (en) * | 2008-06-11 | 2015-04-07 | Emd Millipore Corporation | Stirred tank bioreactor |
| DE102008058246A1 (de) | 2008-11-19 | 2010-05-20 | Basf Se | Hochmolekulare Polyamide |
| WO2010074953A1 (en) | 2008-12-16 | 2010-07-01 | Millipore Corporation | Stirred tank reactor and method |
| CN102245706B (zh) | 2008-12-16 | 2015-01-21 | 巴斯夫欧洲公司 | 抗热老化聚酰胺 |
| DE102010062538A1 (de) | 2009-12-17 | 2011-06-22 | Basf Se, 67063 | Verfahren zur Herstellung geschweisster Formkörper aus Polyamid-6.10 |
| KR101551295B1 (ko) | 2010-05-17 | 2015-09-08 | 이엠디 밀리포어 코포레이션 | 생체분자 정제용 자극 반응성 중합체 |
| BR112013012693A2 (pt) | 2010-11-23 | 2016-09-06 | Basf Se | "processo para produzir misturas de polímero" |
| US9296896B2 (en) | 2010-11-23 | 2016-03-29 | Basf Se | Polyamides with nanoparticles on the surface |
| KR20140042772A (ko) | 2011-01-18 | 2014-04-07 | 바스프 에스이 | 열가소성 몰딩 조성물 |
| US9486981B2 (en) | 2011-09-13 | 2016-11-08 | Basf Se | Use of polyethyleneimines in the preparation of polyamides |
| EP2570448A1 (de) | 2011-09-13 | 2013-03-20 | Basf Se | Verwendung von Polyethyleniminen in der Herstellung von Polyamiden |
| CN103958609B (zh) | 2011-11-25 | 2017-11-10 | 巴斯夫欧洲公司 | 可吹塑的聚酰胺化合物 |
| ES2655563T3 (es) | 2013-08-21 | 2018-02-20 | Basf Se | Procedimiento para la producción de una pieza de plástico compuesto (CK) |
| JP6236532B2 (ja) | 2013-08-21 | 2017-11-22 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 向上した熱老化耐性を有する複合プラスチック部品 |
| JP6169280B2 (ja) | 2013-08-21 | 2017-07-26 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 部材に含まれるプラスチック構成部分間の付着が改善された複合プラスチック部材 |
| US9540596B2 (en) | 2013-08-26 | 2017-01-10 | The Procter & Gamble Company | Compositions comprising alkoxylated polyamines having low melting points |
| JP6916289B2 (ja) * | 2017-08-24 | 2021-08-11 | 株式会社日本触媒 | エチレンイミン重合体溶液およびその製造方法 |
| CN115335456B (zh) | 2020-03-25 | 2024-10-29 | 巴斯夫欧洲公司 | 耐热老化聚酰胺模塑组合物 |
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 AU AU61828/80A patent/AU6182880A/en not_active Abandoned
- 1980-08-28 ZA ZA00805326A patent/ZA805326B/xx unknown
- 1980-08-28 JP JP11785880A patent/JPS5634730A/ja active Granted
- 1980-08-28 ES ES494567A patent/ES8104340A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5634730A (en) | 1981-04-07 |
| US4371674A (en) | 1983-02-01 |
| FI802619A7 (fi) | 1981-03-01 |
| NO152374B (no) | 1985-06-10 |
| AU6182880A (en) | 1981-03-05 |
| ATE4062T1 (de) | 1983-07-15 |
| DE2934854A1 (de) | 1981-09-10 |
| DE3064043D1 (en) | 1983-08-11 |
| ZA805326B (en) | 1981-10-28 |
| NO802543L (no) | 1981-03-02 |
| FI66015B (fi) | 1984-04-30 |
| ES494567A0 (es) | 1981-04-01 |
| FI66015C (fi) | 1984-08-10 |
| ES8104340A1 (es) | 1981-04-01 |
| EP0025515A1 (de) | 1981-03-25 |
| NO152374C (no) | 1985-09-18 |
| EP0025515B1 (de) | 1983-07-06 |
| JPS6351177B2 (enExample) | 1988-10-13 |
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