JPH0363575B2 - - Google Patents
Info
- Publication number
- JPH0363575B2 JPH0363575B2 JP59184695A JP18469584A JPH0363575B2 JP H0363575 B2 JPH0363575 B2 JP H0363575B2 JP 59184695 A JP59184695 A JP 59184695A JP 18469584 A JP18469584 A JP 18469584A JP H0363575 B2 JPH0363575 B2 JP H0363575B2
- Authority
- JP
- Japan
- Prior art keywords
- glycidyl ether
- polyamine
- polyoxyethylene
- modified
- derivative
- 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
- 229920000768 polyamine Polymers 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 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 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- -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 8
- 229920002873 Polyethylenimine Polymers 0.000 description 8
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000004952 Polyamide Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 229920002647 polyamide Polymers 0.000 description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000007720 emulsion polymerization reaction Methods 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 125000001165 hydrophobic group Chemical group 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000004711 α-olefin Substances 0.000 description 3
- MWEMVOWDVQAKHC-UHFFFAOYSA-N 2-(cyclopentyloxymethyl)oxirane Chemical compound C1OC1COC1CCCC1 MWEMVOWDVQAKHC-UHFFFAOYSA-N 0.000 description 2
- HRWYHCYGVIJOEC-UHFFFAOYSA-N 2-(octoxymethyl)oxirane Chemical compound CCCCCCCCOCC1CO1 HRWYHCYGVIJOEC-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 239000007864 aqueous solution 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
- 239000011248 coating agent Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 229920001281 polyalkylene Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 238000004513 sizing Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 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
- AGPVFQKEHYIQGC-UHFFFAOYSA-N 2-(1-phenylnonoxymethyl)oxirane Chemical compound C(C1CO1)OC(C1=CC=CC=C1)CCCCCCCC AGPVFQKEHYIQGC-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
- AGIBHMPYXXPGAX-UHFFFAOYSA-N 2-(iodomethyl)oxirane Chemical compound ICC1CO1 AGIBHMPYXXPGAX-UHFFFAOYSA-N 0.000 description 1
- ZXJBWUAALADCRI-UHFFFAOYSA-N 2-(octadecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCCCCCCCOCC1CO1 ZXJBWUAALADCRI-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
- WUQOLMATUPNUKZ-UHFFFAOYSA-N 2-[(1-dodecylcyclohexyl)oxymethyl]oxirane Chemical compound C1OC1COC1(CCCCCCCCCCCC)CCCCC1 WUQOLMATUPNUKZ-UHFFFAOYSA-N 0.000 description 1
- JGIGDELHKVBSTQ-UHFFFAOYSA-N 2-[(1-dodecylcyclopentyl)oxymethyl]oxirane Chemical compound C(C1CO1)OC1(CCCC1)CCCCCCCCCCCC JGIGDELHKVBSTQ-UHFFFAOYSA-N 0.000 description 1
- KMXIHGNAQLGVKG-UHFFFAOYSA-N 2-[(1-nonylcyclohexyl)oxymethyl]oxirane Chemical compound C(C1CO1)OC1(CCCCC1)CCCCCCCCC KMXIHGNAQLGVKG-UHFFFAOYSA-N 0.000 description 1
- HWJMBUCQUAIDDF-UHFFFAOYSA-N 2-[(1-nonylcyclopentyl)oxymethyl]oxirane Chemical compound C(C1CO1)OC1(CCCC1)CCCCCCCCC HWJMBUCQUAIDDF-UHFFFAOYSA-N 0.000 description 1
- MTAYETAOBPRYRF-UHFFFAOYSA-N 2-[(1-octadecylcyclohexyl)oxymethyl]oxirane Chemical compound C1OC1COC1(CCCCCCCCCCCCCCCCCC)CCCCC1 MTAYETAOBPRYRF-UHFFFAOYSA-N 0.000 description 1
- SLMASIHLCDJSSR-UHFFFAOYSA-N 2-[(1-octadecylcyclopentyl)oxymethyl]oxirane Chemical compound C1OC1COC1(CCCCCCCCCCCCCCCCCC)CCCC1 SLMASIHLCDJSSR-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
- IGDUBEZMULCNAF-UHFFFAOYSA-N 2-[(2-dodecylphenoxy)methyl]oxirane Chemical compound CCCCCCCCCCCCC1=CC=CC=C1OCC1OC1 IGDUBEZMULCNAF-UHFFFAOYSA-N 0.000 description 1
- WNISWKAEAPQCJQ-UHFFFAOYSA-N 2-[(2-nonylphenoxy)methyl]oxirane Chemical compound CCCCCCCCCC1=CC=CC=C1OCC1OC1 WNISWKAEAPQCJQ-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
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-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
- 239000005977 Ethylene Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 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
- 239000004202 carbamide Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000004132 cross linking 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
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 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
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- ZPIRTVJRHUMMOI-UHFFFAOYSA-N octoxybenzene Chemical group CCCCCCCCOC1=CC=CC=C1 ZPIRTVJRHUMMOI-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012261 resinous substance Substances 0.000 description 1
- 239000000243 solution Substances 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Landscapes
- Paper (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Polyethers (AREA)
- 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59184695A JPS6164325A (ja) | 1984-09-05 | 1984-09-05 | 変性ポリアミン |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59184695A JPS6164325A (ja) | 1984-09-05 | 1984-09-05 | 変性ポリアミン |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6164325A JPS6164325A (ja) | 1986-04-02 |
| JPH0363575B2 true JPH0363575B2 (enrdf_load_stackoverflow) | 1991-10-01 |
Family
ID=16157756
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59184695A Granted JPS6164325A (ja) | 1984-09-05 | 1984-09-05 | 変性ポリアミン |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6164325A (enrdf_load_stackoverflow) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3871322B2 (ja) * | 2002-07-11 | 2007-01-24 | ハイモ株式会社 | 水溶性重合体分散液の使用方法 |
| 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 |
| 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 |
| JP5738139B2 (ja) * | 2011-09-15 | 2015-06-17 | 株式会社日本触媒 | ポリアミン系重合体およびその製造方法 |
| WO2016039425A1 (ja) * | 2014-09-10 | 2016-03-17 | 株式会社日本触媒 | ポリアルキレンイミン誘導体を含む抗菌剤 |
-
1984
- 1984-09-05 JP JP59184695A patent/JPS6164325A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6164325A (ja) | 1986-04-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5670612A (en) | Polyamine/epoxy-containing polyoxyethylene/hydrophobic epoxy adduct curing agent | |
| US5344856A (en) | Water-emulsifiable epoxy resin composition | |
| US6136894A (en) | Aqueous epoxy resin system with curing agent from reacting acid-terminated polyalkylene glycol with epoxy-amine adduct | |
| EP1060205B1 (en) | Water dispersible curing agents for epoxy resin | |
| KR960017719A (ko) | 자체-유화 에폭시 경화제 | |
| JPS61166874A (ja) | 接着剤用又は塗料用組成物 | |
| TW513456B (en) | Aqueous dispersions of epoxy resins | |
| JPS6311362B2 (enrdf_load_stackoverflow) | ||
| KR960022650A (ko) | 아미드- 함유 자체- 유화 에폭시 경화제 | |
| US3417140A (en) | Amido-amine compositions | |
| US4056510A (en) | Amine-modified polyethers | |
| KR100568095B1 (ko) | 에폭시 수지의 수성 분산액 및 이의 제조방법 | |
| EP0491550B1 (en) | Water-emulsifiable epoxy resin composition | |
| JPH0363575B2 (enrdf_load_stackoverflow) | ||
| WO1996003452A1 (en) | Curing agents for aqueous epoxy resins | |
| JPH0363574B2 (enrdf_load_stackoverflow) | ||
| JPH0214095B2 (enrdf_load_stackoverflow) | ||
| US5084531A (en) | Epoxy resins containing epoxidized polybutenes | |
| EP0362787A2 (en) | Modified amino curing agents for epoxy resins | |
| EP0511620B1 (en) | Aqueous emulsions of epoxyphenolic resins | |
| JPH10139861A (ja) | 水性エポキシド樹脂組成物 | |
| JPH0229703B2 (enrdf_load_stackoverflow) | ||
| JPH1046008A (ja) | エポキシ樹脂エマルジョン組成物 |