CA2517592A1 - Synthesis of high solids resins from amine terminated polyamides - Google Patents
Synthesis of high solids resins from amine terminated polyamides Download PDFInfo
- Publication number
- CA2517592A1 CA2517592A1 CA002517592A CA2517592A CA2517592A1 CA 2517592 A1 CA2517592 A1 CA 2517592A1 CA 002517592 A CA002517592 A CA 002517592A CA 2517592 A CA2517592 A CA 2517592A CA 2517592 A1 CA2517592 A1 CA 2517592A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- ranges
- process according
- amine
- resin
- 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.)
- Abandoned
Links
- 229920005989 resin Polymers 0.000 title claims abstract description 67
- 239000011347 resin Substances 0.000 title claims abstract description 67
- 239000007787 solid Substances 0.000 title claims abstract description 47
- 150000001412 amines Chemical class 0.000 title claims abstract description 40
- 230000015572 biosynthetic process Effects 0.000 title claims description 16
- 238000003786 synthesis reaction Methods 0.000 title claims description 14
- 239000004952 Polyamide Substances 0.000 title claims description 4
- 229920002647 polyamide Polymers 0.000 title claims description 4
- 238000000034 method Methods 0.000 claims abstract description 46
- 229920000642 polymer Polymers 0.000 claims abstract description 44
- 239000002253 acid Substances 0.000 claims abstract description 32
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- 150000002148 esters Chemical class 0.000 claims abstract description 21
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 23
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 14
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 12
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 12
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 12
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- KSSJBGNOJJETTC-UHFFFAOYSA-N COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC Chemical compound COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC KSSJBGNOJJETTC-UHFFFAOYSA-N 0.000 claims description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 9
- 239000001361 adipic acid Substances 0.000 claims description 7
- 235000011037 adipic acid Nutrition 0.000 claims description 7
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
- OTBHHUPVCYLGQO-UHFFFAOYSA-N bis(3-aminopropyl)amine Chemical compound NCCCNCCCN OTBHHUPVCYLGQO-UHFFFAOYSA-N 0.000 claims description 6
- ALOUNLDAKADEEB-UHFFFAOYSA-N dimethyl sebacate Chemical compound COC(=O)CCCCCCCCC(=O)OC ALOUNLDAKADEEB-UHFFFAOYSA-N 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 claims description 6
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 6
- ATHGHQPFGPMSJY-UHFFFAOYSA-N spermidine Chemical compound NCCCCNCCCN ATHGHQPFGPMSJY-UHFFFAOYSA-N 0.000 claims description 6
- PFNFFQXMRSDOHW-UHFFFAOYSA-N spermine Chemical compound NCCCNCCCCNCCCN PFNFFQXMRSDOHW-UHFFFAOYSA-N 0.000 claims description 6
- 229920006122 polyamide resin Polymers 0.000 claims description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- RGCVYEOTYJCNOS-UHFFFAOYSA-N (4-cyano-2-methylphenyl)boronic acid Chemical compound CC1=CC(C#N)=CC=C1B(O)O RGCVYEOTYJCNOS-UHFFFAOYSA-N 0.000 claims description 3
- BZJTUOGZUKFLQT-UHFFFAOYSA-N 1,3,5,7-tetramethylcyclooctane Chemical group CC1CC(C)CC(C)CC(C)C1 BZJTUOGZUKFLQT-UHFFFAOYSA-N 0.000 claims description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 3
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 3
- WYMDDFRYORANCC-UHFFFAOYSA-N 2-[[3-[bis(carboxymethyl)amino]-2-hydroxypropyl]-(carboxymethyl)amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)CN(CC(O)=O)CC(O)=O WYMDDFRYORANCC-UHFFFAOYSA-N 0.000 claims description 3
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 claims description 3
- JSDVLFNPSDTHGJ-UHFFFAOYSA-N 2-phenylpropane-1,3-diamine Chemical compound NCC(CN)C1=CC=CC=C1 JSDVLFNPSDTHGJ-UHFFFAOYSA-N 0.000 claims description 3
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 claims description 3
- LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 claims description 3
- DRUKNYVQGHETPO-UHFFFAOYSA-N Nonanedioic acid dimethyl ester Natural products COC(=O)CCCCCCCC(=O)OC DRUKNYVQGHETPO-UHFFFAOYSA-N 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 3
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- ZWWQRMFIZFPUAA-UHFFFAOYSA-N dimethyl 2-methylidenebutanedioate Chemical compound COC(=O)CC(=C)C(=O)OC ZWWQRMFIZFPUAA-UHFFFAOYSA-N 0.000 claims description 3
- XTDYIOOONNVFMA-UHFFFAOYSA-N dimethyl pentanedioate Chemical compound COC(=O)CCCC(=O)OC XTDYIOOONNVFMA-UHFFFAOYSA-N 0.000 claims description 3
- 229940014772 dimethyl sebacate Drugs 0.000 claims description 3
- 239000001530 fumaric acid Substances 0.000 claims description 3
- 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 claims description 3
- 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 claims description 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- 150000004986 phenylenediamines Chemical class 0.000 claims description 3
- 229940063673 spermidine Drugs 0.000 claims description 3
- 229940063675 spermine Drugs 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 2
- 239000011976 maleic acid Substances 0.000 claims 2
- 150000005690 diesters Chemical class 0.000 claims 1
- QYMFNZIUDRQRSA-UHFFFAOYSA-N dimethyl butanedioate;dimethyl hexanedioate;dimethyl pentanedioate Chemical compound COC(=O)CCC(=O)OC.COC(=O)CCCC(=O)OC.COC(=O)CCCCC(=O)OC QYMFNZIUDRQRSA-UHFFFAOYSA-N 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000009826 distribution Methods 0.000 description 9
- 229920000768 polyamine Polymers 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 6
- 238000003860 storage Methods 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- IFDLXKQSUOWIBO-UHFFFAOYSA-N 1,3-dichloropropan-1-ol Chemical compound OC(Cl)CCCl IFDLXKQSUOWIBO-UHFFFAOYSA-N 0.000 description 3
- ZXCYIJGIGSDJQQ-UHFFFAOYSA-N 2,3-dichloropropan-1-ol Chemical compound OCC(Cl)CCl ZXCYIJGIGSDJQQ-UHFFFAOYSA-N 0.000 description 3
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-O azetidin-1-ium Chemical compound C1C[NH2+]C1 HONIICLYMWZJFZ-UHFFFAOYSA-O 0.000 description 1
- 125000002091 cationic group Chemical group 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
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004674 formic acids Chemical class 0.000 description 1
- 239000011121 hardwood Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002924 oxiranes Chemical group 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000011122 softwood Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 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
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/028—Polyamidoamines
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/54—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen
- D21H17/55—Polyamides; Polyaminoamides; Polyester-amides
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/146—Crêping adhesives
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/18—Reinforcing agents
- D21H21/20—Wet strength agents
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polyamides (AREA)
- Paper (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/404,940 US6908983B2 (en) | 2003-04-01 | 2003-04-01 | Synthesis of high solids resins from amine terminated polyamides |
| US10/404,940 | 2003-04-01 | ||
| PCT/US2004/009205 WO2004092248A1 (en) | 2003-04-01 | 2004-03-24 | Synthesis of high solids resins from amine terminated polyamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2517592A1 true CA2517592A1 (en) | 2004-10-28 |
Family
ID=33097003
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002517592A Abandoned CA2517592A1 (en) | 2003-04-01 | 2004-03-24 | Synthesis of high solids resins from amine terminated polyamides |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6908983B2 (https=) |
| EP (1) | EP1611185A1 (https=) |
| JP (1) | JP2006522208A (https=) |
| KR (1) | KR20050114697A (https=) |
| CN (1) | CN1771279A (https=) |
| AU (1) | AU2004230842A1 (https=) |
| BR (1) | BRPI0408995A (https=) |
| CA (1) | CA2517592A1 (https=) |
| MX (1) | MXPA05009826A (https=) |
| WO (1) | WO2004092248A1 (https=) |
| ZA (1) | ZA200508857B (https=) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1858955A1 (en) * | 2005-02-23 | 2007-11-28 | E.I. Dupont De Nemours And Company | Processes using alpha, omega-difunctional aldaramides as monomers and crosslinkers |
| WO2008024444A2 (en) * | 2006-08-24 | 2008-02-28 | Hercules Incorporated | Adhesive composition of low molecular weight polyaminopolyamide-epichlorohydrin (pae) resin and protein |
| CN101636431B (zh) * | 2007-01-19 | 2013-02-06 | 赫尔克里士公司 | 由胺端基聚酰胺胺制成的起皱粘合剂 |
| US20080292886A1 (en) * | 2007-03-23 | 2008-11-27 | Hercules Inc. | Adhesive formulations containing urea additives, methods of forming plywood therewith, and plywood products made thereby |
| US20080257507A1 (en) * | 2007-04-17 | 2008-10-23 | Campbell Clayton J | Acidified polyamidoamine adhesives, method of manufacture, and use for creping and ply bond applications |
| CA2701918C (en) * | 2007-10-09 | 2014-08-05 | Hercules Incorporated | Crosslinkercontaining adhesive compositions |
| MX2011004475A (es) | 2008-11-18 | 2011-05-31 | Hercules Inc | Poli (aminoamidas) hidrofobicamente modificadas. |
| US8444812B2 (en) * | 2008-11-18 | 2013-05-21 | Nalco Company | Creping adhesives with improved film properties |
| ES2530624T3 (es) | 2010-02-04 | 2015-03-04 | Solenis Technologies Cayman Lp | Composiciones de adhesivo |
| WO2011136263A1 (ja) * | 2010-04-30 | 2011-11-03 | 宇部興産株式会社 | ポリアミド樹脂 |
| WO2011154331A1 (en) * | 2010-06-10 | 2011-12-15 | F. Hoffmann-La Roche Ag | Polymers for delivery of nucleic acids |
| EP2395041A1 (en) * | 2010-06-10 | 2011-12-14 | F. Hoffmann-La Roche AG | Polymers for delivery of nucleic acids |
| US20120247697A1 (en) | 2011-03-29 | 2012-10-04 | Kemira Oyj | Polyamine Polyamidoamine Epihaloohydrin Compositions and Processes for Preparing and Using the Same |
| PT2761083T (pt) | 2011-09-30 | 2017-08-24 | Kemira Oyj | Papel e métodos para produzir papel |
| JP2013095792A (ja) * | 2011-10-28 | 2013-05-20 | Ube Industries Ltd | 充填材含有ポリアミド樹脂組成物 |
| JP2013095803A (ja) * | 2011-10-28 | 2013-05-20 | Ube Industries Ltd | ポリアミド樹脂組成物及びそれを成形して得た耐熱性成形体 |
| JP2013095793A (ja) * | 2011-10-28 | 2013-05-20 | Ube Industries Ltd | ポリアミド樹脂組成物 |
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| WO2013061650A1 (ja) * | 2011-10-28 | 2013-05-02 | 宇部興産株式会社 | ポリアミド樹脂組成物 |
| US9777434B2 (en) * | 2011-12-22 | 2017-10-03 | Kemira Dyj | Compositions and methods of making paper products |
| US9982395B2 (en) | 2012-07-19 | 2018-05-29 | Ecolab Usa Inc. | High efficiency wet strength resins from new cross-linkers |
| ES3037037T3 (en) | 2012-07-19 | 2025-09-26 | Ecolab Usa Inc | High efficiency wet strength resins from new cross-linkers |
| CN103966902B (zh) * | 2013-02-05 | 2016-08-10 | 星光Pmc株式会社 | 湿润纸力增强剂和内添该湿润纸力增强剂的纸 |
| EP3180474B1 (en) | 2014-08-13 | 2019-01-02 | Solenis Technologies, L.P. | Process to improve performance of wet-strength resins through base activation |
| WO2020181092A1 (en) * | 2019-03-05 | 2020-09-10 | Kemira Oyj | Compositions and methods comprising wet strengthening resins |
| KR20230116829A (ko) | 2020-12-04 | 2023-08-04 | 에이지씨 케미컬스 아메리카스 인코포레이티드 | 처리된 물품, 처리된 물품을 제조하는 방법, 및 처리된 물품을 제조하는 데 이용하기 위한 분산액 |
| EP4262498A4 (en) | 2020-12-17 | 2024-04-24 | First Quality Tissue, LLC | Wet laid disposable absorent structures with high wet strenght and method of making the same |
| CN112961287B (zh) * | 2021-04-15 | 2022-03-08 | 九洲生物技术（苏州）有限公司 | 一种聚酯嵌段pae低有机氯湿强剂的制备方法及应用 |
| US11976421B2 (en) | 2022-06-16 | 2024-05-07 | First Quality Tissue, Llc | Wet laid disposable absorbent structures with high wet strength and method of making the same |
| US11952721B2 (en) | 2022-06-16 | 2024-04-09 | First Quality Tissue, Llc | Wet laid disposable absorbent structures with high wet strength and method of making the same |
| WO2023244871A1 (en) | 2022-06-16 | 2023-12-21 | First Quality Tissue, Llc | Wet laid paper and paperboard products with high wet strength and method of making the same |
| WO2023245090A1 (en) | 2022-06-16 | 2023-12-21 | First Quality Tissue, Llc | Wet laid paper and paperboard products with high wet strength and method of making the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL110447C (https=) * | 1957-09-05 | |||
| US2926154A (en) * | 1957-09-05 | 1960-02-23 | Hercules Powder Co Ltd | Cationic thermosetting polyamide-epichlorohydrin resins and process of making same |
| US3332901A (en) * | 1966-06-16 | 1967-07-25 | Hercules Inc | Cationic water-soluble polyamide-epichlorohydrin resins and method of preparing same |
| BE787371A (fr) | 1971-08-12 | 1973-02-09 | Hercules Inc | Perfectionnements aux resines solubles dans l'eau utilisables pour fabriquer du papier crepe, et aux procedes pour leur production |
| US4515657A (en) * | 1983-04-27 | 1985-05-07 | Hercules Incorporated | Wet Strength resins |
| US4487884A (en) * | 1983-04-27 | 1984-12-11 | Hercules Incorporated | Aqueous solution of cationic thermosetting resin from N-bis(aminopropyl)methylamine/oxalic acid |
| JP2969636B2 (ja) | 1988-12-23 | 1999-11-02 | 住友化学工業株式会社 | 陽イオン性熱硬化性樹脂水溶液の製造方法 |
| US4970250A (en) * | 1989-09-25 | 1990-11-13 | Borden, Inc. | Epoxidized polyamide wet strength resin containing lecithin |
| US5278255A (en) * | 1990-08-17 | 1994-01-11 | The Dow Chemical Company | Unsaturated polyaminopolymer, derivatives thereof and processes for making |
| US5373087A (en) * | 1990-08-17 | 1994-12-13 | The Dow Chemical Company | Unsaturated polyaminopolymers, derivatives thereof and processes for making them |
| CA2058009C (en) * | 1990-12-31 | 1998-08-18 | William W. Maslanka | Synthesis of high solids-content wet-strength resin |
| US5786429A (en) * | 1996-04-18 | 1998-07-28 | Hercules Incorporated | Highly branched polyamidoamines and their preparation |
| US6222006B1 (en) * | 1997-08-13 | 2001-04-24 | Fort James Corporation | Wet strength thermosetting resin formulations and polyaminamide polymers suitable for use in the manufacture of paper products |
| US6103861A (en) * | 1997-12-19 | 2000-08-15 | Hercules Incorporated | Strength resins for paper and repulpable wet and dry strength paper made therewith |
| US6171440B1 (en) * | 1997-12-31 | 2001-01-09 | Hercules Incorporated | Process for repulping wet strength paper having cationic thermosetting resin |
| ATE357470T1 (de) | 1999-06-11 | 2007-04-15 | Hercules Inc | Verfahren zur herstellung von polyamin- epihalohydrin harzen mit reduziertem verunreinigungsgehalt |
| US6352613B1 (en) * | 2000-03-14 | 2002-03-05 | Hercules Incorporated | Resin compositions having high solids contents |
| US6667384B2 (en) * | 2001-12-27 | 2003-12-23 | Hercules Incorporated | Methyl acrylate-diamine based polyamide resins and processes for producing the same |
-
2003
- 2003-04-01 US US10/404,940 patent/US6908983B2/en not_active Expired - Lifetime
-
2004
- 2004-03-24 KR KR1020057018010A patent/KR20050114697A/ko not_active Withdrawn
- 2004-03-24 WO PCT/US2004/009205 patent/WO2004092248A1/en not_active Ceased
- 2004-03-24 AU AU2004230842A patent/AU2004230842A1/en not_active Abandoned
- 2004-03-24 CN CNA2004800093212A patent/CN1771279A/zh active Pending
- 2004-03-24 JP JP2006509308A patent/JP2006522208A/ja not_active Withdrawn
- 2004-03-24 BR BRPI0408995-2A patent/BRPI0408995A/pt not_active IP Right Cessation
- 2004-03-24 CA CA002517592A patent/CA2517592A1/en not_active Abandoned
- 2004-03-24 EP EP04758964A patent/EP1611185A1/en not_active Withdrawn
- 2004-03-24 MX MXPA05009826A patent/MXPA05009826A/es active IP Right Grant
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2005
- 2005-11-01 ZA ZA200508857A patent/ZA200508857B/en unknown
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|---|---|
| MXPA05009826A (es) | 2005-12-05 |
| ZA200508857B (en) | 2006-11-29 |
| EP1611185A1 (en) | 2006-01-04 |
| KR20050114697A (ko) | 2005-12-06 |
| CN1771279A (zh) | 2006-05-10 |
| US6908983B2 (en) | 2005-06-21 |
| AU2004230842A1 (en) | 2004-10-28 |
| BRPI0408995A (pt) | 2006-03-28 |
| US20040198947A1 (en) | 2004-10-07 |
| WO2004092248A1 (en) | 2004-10-28 |
| JP2006522208A (ja) | 2006-09-28 |
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| EEER | Examination request | ||
| FZDE | Discontinued |