JPH0363574B2 - - Google Patents
Info
- Publication number
- JPH0363574B2 JPH0363574B2 JP59184694A JP18469484A JPH0363574B2 JP H0363574 B2 JPH0363574 B2 JP H0363574B2 JP 59184694 A JP59184694 A JP 59184694A JP 18469484 A JP18469484 A JP 18469484A JP H0363574 B2 JPH0363574 B2 JP H0363574B2
- Authority
- JP
- Japan
- Prior art keywords
- polyamine
- glycidyl ether
- polyoxyethylene
- modified
- formula
- 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 - Lifetime
Links
- 229920000768 polyamine Polymers 0.000 claims description 60
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- -1 alkylene imine Chemical class 0.000 description 47
- 125000000217 alkyl group Chemical group 0.000 description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- 125000002947 alkylene group Chemical group 0.000 description 6
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 6
- 229920002873 Polyethylenimine Polymers 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 238000007720 emulsion polymerization reaction Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 150000003333 secondary alcohols Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- GQWWGRUJOCIUKI-UHFFFAOYSA-N 2-[3-(2-methyl-1-oxopyrrolo[1,2-a]pyrazin-3-yl)propyl]guanidine Chemical compound O=C1N(C)C(CCCN=C(N)N)=CN2C=CC=C21 GQWWGRUJOCIUKI-UHFFFAOYSA-N 0.000 description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000001165 hydrophobic group Chemical group 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 239000012261 resinous substance Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- IIJVPBUAAGXRDV-UHFFFAOYSA-N 2-(1-phenyldecoxymethyl)oxirane Chemical compound C(C1CO1)OC(C1=CC=CC=C1)CCCCCCCCC IIJVPBUAAGXRDV-UHFFFAOYSA-N 0.000 description 1
- COXNXNKFEOSOFZ-UHFFFAOYSA-N 2-(1-phenylnonadecoxymethyl)oxirane Chemical compound C=1C=CC=CC=1C(CCCCCCCCCCCCCCCCCC)OCC1CO1 COXNXNKFEOSOFZ-UHFFFAOYSA-N 0.000 description 1
- FYEHDUSTWVFLKO-UHFFFAOYSA-N 2-(1-phenyltridecoxymethyl)oxirane Chemical compound C(C1CO1)OC(C1=CC=CC=C1)CCCCCCCCCCCC FYEHDUSTWVFLKO-UHFFFAOYSA-N 0.000 description 1
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 description 1
- XNJDQHLXEBQMDE-UHFFFAOYSA-N 2-(cyclohexyloxymethyl)oxirane Chemical compound C1OC1COC1CCCCC1 XNJDQHLXEBQMDE-UHFFFAOYSA-N 0.000 description 1
- VMSIYTPWZLSMOH-UHFFFAOYSA-N 2-(dodecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCOCC1CO1 VMSIYTPWZLSMOH-UHFFFAOYSA-N 0.000 description 1
- KEKXMAURKVLACV-UHFFFAOYSA-N 2-(nonoxymethyl)oxirane Chemical class CCCCCCCCCOCC1CO1 KEKXMAURKVLACV-UHFFFAOYSA-N 0.000 description 1
- ZXJBWUAALADCRI-UHFFFAOYSA-N 2-(octadecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCCCCCCCOCC1CO1 ZXJBWUAALADCRI-UHFFFAOYSA-N 0.000 description 1
- HRWYHCYGVIJOEC-UHFFFAOYSA-N 2-(octoxymethyl)oxirane Chemical compound CCCCCCCCOCC1CO1 HRWYHCYGVIJOEC-UHFFFAOYSA-N 0.000 description 1
- QNYBOILAKBSWFG-UHFFFAOYSA-N 2-(phenylmethoxymethyl)oxirane Chemical compound C1OC1COCC1=CC=CC=C1 QNYBOILAKBSWFG-UHFFFAOYSA-N 0.000 description 1
- OZDGMOYKSFPLSE-UHFFFAOYSA-N 2-Methylaziridine Chemical compound CC1CN1 OZDGMOYKSFPLSE-UHFFFAOYSA-N 0.000 description 1
- HWJMBUCQUAIDDF-UHFFFAOYSA-N 2-[(1-nonylcyclopentyl)oxymethyl]oxirane Chemical class C(C1CO1)OC1(CCCC1)CCCCCCCCC HWJMBUCQUAIDDF-UHFFFAOYSA-N 0.000 description 1
- VJUAZEOWGBYSLU-UHFFFAOYSA-N 2-[(1-octylcyclohexyl)oxymethyl]oxirane Chemical compound C1OC1COC1(CCCCCCCC)CCCCC1 VJUAZEOWGBYSLU-UHFFFAOYSA-N 0.000 description 1
- IQSSBBYUPFLYKK-UHFFFAOYSA-N 2-[(1-octylcyclopentyl)oxymethyl]oxirane Chemical compound C(C1CO1)OC1(CCCC1)CCCCCCCC IQSSBBYUPFLYKK-UHFFFAOYSA-N 0.000 description 1
- IGDUBEZMULCNAF-UHFFFAOYSA-N 2-[(2-dodecylphenoxy)methyl]oxirane Chemical compound CCCCCCCCCCCCC1=CC=CC=C1OCC1OC1 IGDUBEZMULCNAF-UHFFFAOYSA-N 0.000 description 1
- CCYKKRHICFHBTR-UHFFFAOYSA-N 2-[(2-octadecylphenoxy)methyl]oxirane Chemical compound CCCCCCCCCCCCCCCCCCC1=CC=CC=C1OCC1OC1 CCYKKRHICFHBTR-UHFFFAOYSA-N 0.000 description 1
- MVGLGWVANWQXLJ-UHFFFAOYSA-N 2-[(2-octylphenoxy)methyl]oxirane Chemical compound CCCCCCCCC1=CC=CC=C1OCC1OC1 MVGLGWVANWQXLJ-UHFFFAOYSA-N 0.000 description 1
- SJLODCMGBPCIHA-UHFFFAOYSA-N 2-[1-cyclohexyl-1-[1-cyclohexyl-1-(oxiran-2-yl)decoxy]decyl]oxirane Chemical compound C1OC1C(C1CCCCC1)(CCCCCCCCC)OC(CCCCCCCCC)(C1CCCCC1)C1CO1 SJLODCMGBPCIHA-UHFFFAOYSA-N 0.000 description 1
- PKPUAGMYZSLGRH-UHFFFAOYSA-N 2-[1-cyclohexyl-1-[1-cyclohexyl-1-(oxiran-2-yl)nonadecoxy]nonadecyl]oxirane Chemical compound C(CCCCCCCCCCCCCCCCC)C(C1CO1)(C1CCCCC1)OC(C1CO1)(CCCCCCCCCCCCCCCCCC)C1CCCCC1 PKPUAGMYZSLGRH-UHFFFAOYSA-N 0.000 description 1
- YWANOKMBEFRAJV-UHFFFAOYSA-N 2-[1-cyclohexyl-1-[1-cyclohexyl-1-(oxiran-2-yl)tridecoxy]tridecyl]oxirane Chemical compound C(CCCCCCCCCCC)C(C1CO1)(C1CCCCC1)OC(C1CO1)(CCCCCCCCCCCC)C1CCCCC1 YWANOKMBEFRAJV-UHFFFAOYSA-N 0.000 description 1
- GNVLEDJRZZWPNZ-UHFFFAOYSA-N 2-[1-cyclopentyl-1-[1-cyclopentyl-1-(oxiran-2-yl)nonadecoxy]nonadecyl]oxirane Chemical compound C(CCCCCCCCCCCCCCCCC)C(C1CO1)(C1CCCC1)OC(C1CO1)(CCCCCCCCCCCCCCCCCC)C1CCCC1 GNVLEDJRZZWPNZ-UHFFFAOYSA-N 0.000 description 1
- NGCACSQHGAHCPN-UHFFFAOYSA-N 2-[1-cyclopentyl-1-[1-cyclopentyl-1-(oxiran-2-yl)tridecoxy]tridecyl]oxirane Chemical compound C(CCCCCCCCCCC)C(C1CO1)(C1CCCC1)OC(C1CO1)(CCCCCCCCCCCC)C1CCCC1 NGCACSQHGAHCPN-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 150000003938 benzyl alcohols Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- ZPIRTVJRHUMMOI-UHFFFAOYSA-N octoxybenzene Chemical group CCCCCCCCOC1=CC=CC=C1 ZPIRTVJRHUMMOI-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Landscapes
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Paper (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Polyethers (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59184694A JPS6164324A (ja) | 1984-09-05 | 1984-09-05 | 変性したポリアミン |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59184694A JPS6164324A (ja) | 1984-09-05 | 1984-09-05 | 変性したポリアミン |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6164324A JPS6164324A (ja) | 1986-04-02 |
| JPH0363574B2 true JPH0363574B2 (zh) | 1991-10-01 |
Family
ID=16157738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59184694A Granted JPS6164324A (ja) | 1984-09-05 | 1984-09-05 | 変性したポリアミン |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6164324A (zh) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4240110A1 (de) * | 1992-11-28 | 1994-06-01 | Basf Ag | Kondensationsprodukte von Polyalkylenpolyaminen, Verfahren zu ihrer Herstellung und ihre Verwendung bei der Herstellung von Papier |
| DE10112555A1 (de) * | 2001-03-15 | 2002-10-02 | Vantico Gmbh & Co Kg | Addukte aus Polyalkylenglykolmonoglycidylethern und Aminverbindungen |
| JP4549135B2 (ja) * | 2003-09-24 | 2010-09-22 | 株式会社日本触媒 | ポリアルキレンイミンアルキレンオキシド共重合体 |
| EP1518882A1 (en) * | 2003-09-24 | 2005-03-30 | Nippon Shokubai Co., Ltd. | Polyalkyleneimine alkylene oxide copolymer |
| JP4891553B2 (ja) * | 2005-03-04 | 2012-03-07 | 株式会社日本触媒 | 末端変性ポリアルキレンイミンアルキレンオキシド共重合体 |
| JP4824973B2 (ja) * | 2005-08-26 | 2011-11-30 | Ｄｉｃ株式会社 | エポキシ主鎖とアルキレンイミン側鎖とを有する共重合体からなる顔料分散剤 |
| JP2009161762A (ja) * | 2009-02-13 | 2009-07-23 | Nippon Shokubai Co Ltd | 変性アルキレンイミン系重合体 |
| JP5660905B2 (ja) * | 2011-01-20 | 2015-01-28 | 株式会社日本触媒 | ポリアルキレンアミンアルキレンオキシド共重合体 |
| JP2017160128A (ja) * | 2016-03-07 | 2017-09-14 | 株式会社日本触媒 | ポリアルキレンイミン誘導体からなる化粧料用基材 |
-
1984
- 1984-09-05 JP JP59184694A patent/JPS6164324A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6164324A (ja) | 1986-04-02 |
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