JP2006522208A - アミン末端ポリアミドからの高固形分樹脂の合成 - Google Patents
アミン末端ポリアミドからの高固形分樹脂の合成 Download PDFInfo
- Publication number
- JP2006522208A JP2006522208A JP2006509308A JP2006509308A JP2006522208A JP 2006522208 A JP2006522208 A JP 2006522208A JP 2006509308 A JP2006509308 A JP 2006509308A JP 2006509308 A JP2006509308 A JP 2006509308A JP 2006522208 A JP2006522208 A JP 2006522208A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- amine
- resin
- dimethyl
- intermediate polymer
- 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.)
- Withdrawn
Links
- 239000011347 resin Substances 0.000 title claims abstract description 63
- 229920005989 resin Polymers 0.000 title claims abstract description 63
- 239000007787 solid Substances 0.000 title claims abstract description 45
- 239000004952 Polyamide Substances 0.000 title claims description 3
- 229920002647 polyamide Polymers 0.000 title claims description 3
- 230000015572 biosynthetic process Effects 0.000 title description 10
- 238000003786 synthesis reaction Methods 0.000 title description 9
- 238000000034 method Methods 0.000 claims abstract description 44
- 229920000642 polymer Polymers 0.000 claims abstract description 44
- 150000001412 amines Chemical class 0.000 claims abstract description 37
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- 239000002253 acid Substances 0.000 claims abstract description 29
- 150000002148 esters Chemical class 0.000 claims abstract description 21
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 7
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical group NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 35
- 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 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 12
- 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 11
- 239000001361 adipic acid Substances 0.000 claims description 10
- 235000011037 adipic acid Nutrition 0.000 claims description 10
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 9
- 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
- 238000004519 manufacturing process Methods 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
- 230000000379 polymerizing effect Effects 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 5
- 229920006122 polyamide resin Polymers 0.000 claims description 5
- 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
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 3
- XKYCMGFYLXPPMS-UHFFFAOYSA-N 1-phenylpentane-2,4-diamine Chemical compound CC(N)CC(N)CC1=CC=CC=C1 XKYCMGFYLXPPMS-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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- BELZJFWUNQWBES-UHFFFAOYSA-N caldopentamine Chemical compound NCCCNCCCNCCCNCCCN BELZJFWUNQWBES-UHFFFAOYSA-N 0.000 claims description 3
- 239000001913 cellulose Substances 0.000 claims description 3
- 229920002678 cellulose Polymers 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
- 239000003623 enhancer Substances 0.000 claims description 3
- 239000001530 fumaric acid Substances 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
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- 239000000463 material Substances 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
- 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
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 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
- 150000007513 acids Chemical class 0.000 abstract description 5
- 230000002708 enhancing effect Effects 0.000 abstract description 3
- 238000009826 distribution Methods 0.000 description 9
- 229920000768 polyamine Polymers 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 238000011156 evaluation Methods 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
- 229920001577 copolymer Polymers 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
- 238000011179 visual inspection Methods 0.000 description 2
- 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 1
- 238000004458 analytical method Methods 0.000 description 1
- -1 and the like Substances 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-O azetidin-1-ium Chemical compound C1C[NH2+]C1 HONIICLYMWZJFZ-UHFFFAOYSA-O 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 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
- 238000007598 dipping method Methods 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
- 239000011121 hardwood Substances 0.000 description 1
- 230000007774 longterm Effects 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
- 239000002994 raw material Substances 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
- 239000000126 substance Substances 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 (2)
| 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 |
| PCT/US2004/009205 WO2004092248A1 (en) | 2003-04-01 | 2004-03-24 | Synthesis of high solids resins from amine terminated polyamides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006522208A true JP2006522208A (ja) | 2006-09-28 |
| JP2006522208A5 JP2006522208A5 (https=) | 2007-05-17 |
Family
ID=33097003
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006509308A Withdrawn JP2006522208A (ja) | 2003-04-01 | 2004-03-24 | アミン末端ポリアミドからの高固形分樹脂の合成 |
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=) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010516911A (ja) * | 2007-01-19 | 2010-05-20 | ハーキュリーズ・インコーポレーテッド | アミン末端を有するポリアミドアミンから生成したクレーピング用接着剤 |
| WO2011136263A1 (ja) * | 2010-04-30 | 2011-11-03 | 宇部興産株式会社 | ポリアミド樹脂 |
| 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 |
| JP2013095793A (ja) * | 2011-10-28 | 2013-05-20 | Ube Industries Ltd | ポリアミド樹脂組成物 |
| 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 |
| JP2013095778A (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成形体 |
| WO2014123119A1 (ja) * | 2013-02-05 | 2014-08-14 | 星光Pmc株式会社 | 湿潤紙力向上剤及び湿潤紙力向上剤内添紙 |
Families Citing this family (24)
| 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 |
| MY150700A (en) * | 2006-08-24 | 2014-02-28 | Hercules Inc | Adhesive composition of low molecular weight polyaminopolyamide-epichlorohydrin (pae) resin and protein |
| 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 |
| WO2008131071A1 (en) * | 2007-04-17 | 2008-10-30 | Kemira Chemicals Inc. | Acidified polyamidoamine adhesives, method of manufacture, and use for creping and ply bond applications |
| US8147968B2 (en) * | 2007-10-09 | 2012-04-03 | Hercules Incorportated | Diluents for crosslinker-containing adhesive compositions |
| US8444812B2 (en) * | 2008-11-18 | 2013-05-21 | Nalco Company | Creping adhesives with improved film properties |
| US8506757B2 (en) | 2008-11-18 | 2013-08-13 | Hercules Incorporated | Hydrophobically modified poly(aminoamides) |
| ES2530624T3 (es) * | 2010-02-04 | 2015-03-04 | Solenis Technologies Cayman Lp | Composiciones de adhesivo |
| WO2011154331A1 (en) * | 2010-06-10 | 2011-12-15 | F. Hoffmann-La Roche Ag | Polymers for delivery of nucleic acids |
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-
2003
- 2003-04-01 US US10/404,940 patent/US6908983B2/en not_active Expired - Lifetime
-
2004
- 2004-03-24 WO PCT/US2004/009205 patent/WO2004092248A1/en not_active Ceased
- 2004-03-24 EP EP04758964A patent/EP1611185A1/en not_active Withdrawn
- 2004-03-24 JP JP2006509308A patent/JP2006522208A/ja not_active Withdrawn
- 2004-03-24 KR KR1020057018010A patent/KR20050114697A/ko not_active Withdrawn
- 2004-03-24 AU AU2004230842A patent/AU2004230842A1/en not_active Abandoned
- 2004-03-24 CN CNA2004800093212A patent/CN1771279A/zh active Pending
- 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 MX MXPA05009826A patent/MXPA05009826A/es active IP Right Grant
-
2005
- 2005-11-01 ZA ZA200508857A patent/ZA200508857B/en unknown
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010516911A (ja) * | 2007-01-19 | 2010-05-20 | ハーキュリーズ・インコーポレーテッド | アミン末端を有するポリアミドアミンから生成したクレーピング用接着剤 |
| WO2011136263A1 (ja) * | 2010-04-30 | 2011-11-03 | 宇部興産株式会社 | ポリアミド樹脂 |
| US8975364B2 (en) | 2010-04-30 | 2015-03-10 | Ube Industries, Ltd. | Polyamide resin |
| JP5796573B2 (ja) * | 2010-04-30 | 2015-10-21 | 宇部興産株式会社 | ポリアミド樹脂 |
| 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 |
| JP2013095793A (ja) * | 2011-10-28 | 2013-05-20 | Ube Industries Ltd | ポリアミド樹脂組成物 |
| 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 |
| JP2013095778A (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成形体 |
| WO2014123119A1 (ja) * | 2013-02-05 | 2014-08-14 | 星光Pmc株式会社 | 湿潤紙力向上剤及び湿潤紙力向上剤内添紙 |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200508857B (en) | 2006-11-29 |
| CN1771279A (zh) | 2006-05-10 |
| BRPI0408995A (pt) | 2006-03-28 |
| CA2517592A1 (en) | 2004-10-28 |
| EP1611185A1 (en) | 2006-01-04 |
| AU2004230842A1 (en) | 2004-10-28 |
| MXPA05009826A (es) | 2005-12-05 |
| KR20050114697A (ko) | 2005-12-06 |
| US20040198947A1 (en) | 2004-10-07 |
| WO2004092248A1 (en) | 2004-10-28 |
| US6908983B2 (en) | 2005-06-21 |
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