JPH0365817B2 - - Google Patents
Info
- Publication number
- JPH0365817B2 JPH0365817B2 JP59087157A JP8715784A JPH0365817B2 JP H0365817 B2 JPH0365817 B2 JP H0365817B2 JP 59087157 A JP59087157 A JP 59087157A JP 8715784 A JP8715784 A JP 8715784A JP H0365817 B2 JPH0365817 B2 JP H0365817B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- general formula
- carbon atoms
- integer
- polymerization
- 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
- 238000006116 polymerization reaction Methods 0.000 claims description 39
- 229920001577 copolymer Polymers 0.000 claims description 32
- -1 2-hydroxy-1-methylethyl group Chemical group 0.000 claims description 28
- 229920001400 block copolymer Polymers 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 238000012656 cationic ring opening polymerization Methods 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 16
- 229920005604 random copolymer Polymers 0.000 claims description 11
- 239000004094 surface-active agent Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- BYVSMDBDTBXASR-UHFFFAOYSA-N 5,6-dihydro-4h-oxazine Chemical compound C1CON=CC1 BYVSMDBDTBXASR-UHFFFAOYSA-N 0.000 claims 1
- 150000002466 imines Chemical class 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 150000004893 oxazines Chemical class 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 26
- 239000000178 monomer Substances 0.000 description 22
- 230000000052 comparative effect Effects 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 230000000694 effects Effects 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 230000007423 decrease Effects 0.000 description 9
- 230000000704 physical effect Effects 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000003505 polymerization initiator Substances 0.000 description 6
- GUXJXWKCUUWCLX-UHFFFAOYSA-N 2-methyl-2-oxazoline Chemical compound CC1=NCCO1 GUXJXWKCUUWCLX-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000003708 ampul Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 4
- 230000031709 bromination Effects 0.000 description 4
- 238000005893 bromination reaction Methods 0.000 description 4
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- SWYMJLYPXAXHBJ-UHFFFAOYSA-N 2-(4,5-dihydro-1,3-oxazol-2-yl)propan-1-ol Chemical compound OCC(C)C1=NCCO1 SWYMJLYPXAXHBJ-UHFFFAOYSA-N 0.000 description 3
- VERUITIRUQLVOC-UHFFFAOYSA-N 2-butyl-4,5-dihydro-1,3-oxazole Chemical group CCCCC1=NCCO1 VERUITIRUQLVOC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- LRTZAUAUUUURAF-UHFFFAOYSA-N 2-octyl-4,5-dihydro-1,3-oxazole Chemical compound CCCCCCCCC1=NCCO1 LRTZAUAUUUURAF-UHFFFAOYSA-N 0.000 description 2
- OCSXKMIYKAIBCF-UHFFFAOYSA-N 2-undecyl-4,5-dihydro-1,3-oxazole Chemical compound CCCCCCCCCCCC1=NCCO1 OCSXKMIYKAIBCF-UHFFFAOYSA-N 0.000 description 2
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- PAWVJRPRVYDHLQ-UHFFFAOYSA-N 2-(4,5-dihydro-1,3-oxazol-2-yl)ethanol Chemical compound OCCC1=NCCO1 PAWVJRPRVYDHLQ-UHFFFAOYSA-N 0.000 description 1
- NUNKLRNANFBFIP-UHFFFAOYSA-N 2-decyl-4,5-dihydro-1,3-oxazole Chemical compound CCCCCCCCCCC1=NCCO1 NUNKLRNANFBFIP-UHFFFAOYSA-N 0.000 description 1
- OWWOMMRAJBVMAC-UHFFFAOYSA-N 2-dodecyl-4,5-dihydro-1,3-oxazole Chemical compound CCCCCCCCCCCCC1=NCCO1 OWWOMMRAJBVMAC-UHFFFAOYSA-N 0.000 description 1
- NYEZZYQZRQDLEH-UHFFFAOYSA-N 2-ethyl-4,5-dihydro-1,3-oxazole Chemical compound CCC1=NCCO1 NYEZZYQZRQDLEH-UHFFFAOYSA-N 0.000 description 1
- GIGOAOBKJCQHSF-UHFFFAOYSA-N 2-heptadecyl-4,5-dihydro-1,3-oxazole Chemical compound CCCCCCCCCCCCCCCCCC1=NCCO1 GIGOAOBKJCQHSF-UHFFFAOYSA-N 0.000 description 1
- BWDVBMJUJCPESR-UHFFFAOYSA-N 2-heptyl-4,5-dihydro-1,3-oxazole Chemical compound CCCCCCCC1=NCCO1 BWDVBMJUJCPESR-UHFFFAOYSA-N 0.000 description 1
- XGBNRVRKSGTHJT-UHFFFAOYSA-N 2-hexadecyl-4,5-dihydro-1,3-oxazole Chemical compound CCCCCCCCCCCCCCCCC1=NCCO1 XGBNRVRKSGTHJT-UHFFFAOYSA-N 0.000 description 1
- AADZRTSFCAMLBV-UHFFFAOYSA-N 2-hexyl-4,5-dihydro-1,3-oxazole Chemical compound CCCCCCC1=NCCO1 AADZRTSFCAMLBV-UHFFFAOYSA-N 0.000 description 1
- JBPBWSKDBJRSAU-UHFFFAOYSA-N 2-naphthalen-2-yl-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=C(C=CC=C2)C2=C1 JBPBWSKDBJRSAU-UHFFFAOYSA-N 0.000 description 1
- OQWAVMKUNIQCFD-UHFFFAOYSA-N 2-nonyl-4,5-dihydro-1,3-oxazole Chemical compound CCCCCCCCCC1=NCCO1 OQWAVMKUNIQCFD-UHFFFAOYSA-N 0.000 description 1
- ZWXOPTQPMFPVNA-UHFFFAOYSA-N 2-octadecyl-4,5-dihydro-1,3-oxazole Chemical compound CCCCCCCCCCCCCCCCCCC1=NCCO1 ZWXOPTQPMFPVNA-UHFFFAOYSA-N 0.000 description 1
- BJQFPPVYNUKSCM-UHFFFAOYSA-N 2-pentadecyl-4,5-dihydro-1,3-oxazole Chemical compound CCCCCCCCCCCCCCCC1=NCCO1 BJQFPPVYNUKSCM-UHFFFAOYSA-N 0.000 description 1
- OEENXWLHBPUUFL-UHFFFAOYSA-N 2-pentyl-4,5-dihydro-1,3-oxazole Chemical compound CCCCCC1=NCCO1 OEENXWLHBPUUFL-UHFFFAOYSA-N 0.000 description 1
- ZXTHWIZHGLNEPG-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=C1 ZXTHWIZHGLNEPG-UHFFFAOYSA-N 0.000 description 1
- GXCJLVVUIVSLOQ-UHFFFAOYSA-N 2-propyl-4,5-dihydro-1,3-oxazole Chemical compound CCCC1=NCCO1 GXCJLVVUIVSLOQ-UHFFFAOYSA-N 0.000 description 1
- SDADDJBCSSCSPN-UHFFFAOYSA-N 2-tetradecyl-4,5-dihydro-1,3-oxazole Chemical compound CCCCCCCCCCCCCCC1=NCCO1 SDADDJBCSSCSPN-UHFFFAOYSA-N 0.000 description 1
- AXTWULOROZCMFV-UHFFFAOYSA-N 2-tridecyl-4,5-dihydro-1,3-oxazole Chemical compound CCCCCCCCCCCCCC1=NCCO1 AXTWULOROZCMFV-UHFFFAOYSA-N 0.000 description 1
- VEERNCWDIVHRAJ-UHFFFAOYSA-N 3-(4,5-dihydro-1,3-oxazol-2-yl)propan-1-ol Chemical compound OCCCC1=NCCO1 VEERNCWDIVHRAJ-UHFFFAOYSA-N 0.000 description 1
- APZBIEHZUCEYNW-UHFFFAOYSA-N 4,5-dihydro-1,3-oxazol-2-ylmethanol Chemical compound OCC1=NCCO1 APZBIEHZUCEYNW-UHFFFAOYSA-N 0.000 description 1
- PLUBXMRUUVWRLT-UHFFFAOYSA-N Ethyl methanesulfonate Chemical compound CCOS(C)(=O)=O PLUBXMRUUVWRLT-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 238000012661 block copolymerization Methods 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- LFLBHTZRLVHUQC-UHFFFAOYSA-N butyl methanesulfonate Chemical compound CCCCOS(C)(=O)=O LFLBHTZRLVHUQC-UHFFFAOYSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000010550 living polymerization reaction Methods 0.000 description 1
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- JTTWNTXHFYNETH-UHFFFAOYSA-N propyl 4-methylbenzenesulfonate Chemical compound CCCOS(=O)(=O)C1=CC=C(C)C=C1 JTTWNTXHFYNETH-UHFFFAOYSA-N 0.000 description 1
- DKORSYDQYFVQNS-UHFFFAOYSA-N propyl methanesulfonate Chemical compound CCCOS(C)(=O)=O DKORSYDQYFVQNS-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59087157A JPS60229927A (ja) | 1984-04-27 | 1984-04-27 | 水酸基を有する共重合体、その製法および用途 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59087157A JPS60229927A (ja) | 1984-04-27 | 1984-04-27 | 水酸基を有する共重合体、その製法および用途 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60229927A JPS60229927A (ja) | 1985-11-15 |
| JPH0365817B2 true JPH0365817B2 (https=) | 1991-10-15 |
Family
ID=13907151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59087157A Granted JPS60229927A (ja) | 1984-04-27 | 1984-04-27 | 水酸基を有する共重合体、その製法および用途 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60229927A (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5854331A (en) * | 1997-11-04 | 1998-12-29 | E. I. Du Pont De Nemours And Company | Block copolymers of oxazolines and oxazines as pigment dispersants and their use in ink jet inks |
-
1984
- 1984-04-27 JP JP59087157A patent/JPS60229927A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60229927A (ja) | 1985-11-15 |
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