CA1039727A - Imidazolines non saturees - Google Patents

Imidazolines non saturees

Info

Publication number: CA1039727A
Authority: CA; Canada
Prior art keywords: hydrogen; imidazoline; monomer; vinyl; process according
Prior art date: 1975-05-08
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

Application number

CA226,547A

Other languages

English (en)

Other versions

CA226547S (fr

Inventor

Michael N. D. O'connor

Hans P. Panzer

Louis J. Baccei

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wyeth Holdings LLC

Original Assignee

American Cyanamid Co

Priority date (The priority date 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 date listed.)

1975-05-08

Filing date

1975-05-08

Publication date

1978-10-03

1975-05-08 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1975-05-08 Priority to CA226,547A priority Critical patent/CA1039727A/fr

1978-10-03 Application granted granted Critical

1978-10-03 Publication of CA1039727A publication Critical patent/CA1039727A/fr

Status Expired legal-status Critical Current

Links

150000002462 imidazolines Chemical class 0.000 title abstract description 13
238000000034 method Methods 0.000 claims abstract description 44
150000001875 compounds Chemical class 0.000 claims abstract description 43
229920001577 copolymer Polymers 0.000 claims abstract description 35
230000008569 process Effects 0.000 claims abstract description 25
239000002253 acid Substances 0.000 claims abstract description 23
239000001257 hydrogen Substances 0.000 claims abstract description 23
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
125000000217 alkyl group Chemical group 0.000 claims abstract description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
125000003118 aryl group Chemical group 0.000 claims abstract description 9
238000002360 preparation method Methods 0.000 claims abstract description 8
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
239000000178 monomer Substances 0.000 claims description 52
-1 pyrimidine compound Chemical class 0.000 claims description 41
239000003054 catalyst Substances 0.000 claims description 23
229920001519 homopolymer Polymers 0.000 claims description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
238000005336 cracking Methods 0.000 claims description 18
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 16
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 16
150000001409 amidines Chemical class 0.000 claims description 14
150000002463 imidates Chemical class 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 14
ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 12
150000002431 hydrogen Chemical group 0.000 claims description 11
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 10
OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical group C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 claims description 9
150000004985 diamines Chemical class 0.000 claims description 9
XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 claims description 8
235000010265 sodium sulphite Nutrition 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
229910001870 ammonium persulfate Inorganic materials 0.000 claims description 6
239000000839 emulsion Substances 0.000 claims description 6
239000011953 free-radical catalyst Substances 0.000 claims description 6
239000012458 free base Substances 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 3
150000003230 pyrimidines Chemical class 0.000 claims description 3
239000004094 surface-active agent Substances 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
125000003435 aroyl group Chemical group 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 2
125000002636 imidazolinyl group Chemical group 0.000 claims 2
125000000714 pyrimidinyl group Chemical group 0.000 claims 1
229920000642 polymer Polymers 0.000 abstract description 75
238000006243 chemical reaction Methods 0.000 abstract description 34
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract description 17
229920002554 vinyl polymer Polymers 0.000 abstract description 15
150000005326 tetrahydropyrimidines Chemical class 0.000 abstract description 10
239000010865 sewage Substances 0.000 abstract description 3
239000000725 suspension Substances 0.000 abstract description 3
239000002921 fermentation waste Substances 0.000 abstract description 2
239000000243 solution Substances 0.000 description 56
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
150000003839 salts Chemical class 0.000 description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
QDSPSYXUNKKWMN-UHFFFAOYSA-N 2-ethenyl-4,5-dihydro-1h-imidazole Chemical compound C=CC1=NCCN1 QDSPSYXUNKKWMN-UHFFFAOYSA-N 0.000 description 22
238000006116 polymerization reaction Methods 0.000 description 19
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
229940117913 acrylamide Drugs 0.000 description 17
150000002825 nitriles Chemical class 0.000 description 16
239000011521 glass Substances 0.000 description 15
239000000047 product Substances 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
238000005481 NMR spectroscopy Methods 0.000 description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
239000000463 material Substances 0.000 description 10
229910052757 nitrogen Inorganic materials 0.000 description 10
239000010802 sludge Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000007787 solid Substances 0.000 description 9
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 8
238000001816 cooling Methods 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
238000001035 drying Methods 0.000 description 7
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 7
ZKECLWNBBZPOFW-UHFFFAOYSA-N 2-ethenyl-4,5-dihydro-1h-imidazol-3-ium;hydrogen sulfate Chemical compound OS(O)(=O)=O.C=CC1=NCCN1 ZKECLWNBBZPOFW-UHFFFAOYSA-N 0.000 description 6
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
239000011324 bead Substances 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
229940012017 ethylenediamine Drugs 0.000 description 6
239000007789 gas Substances 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
HXVJQEGYAYABRY-UHFFFAOYSA-N 1-ethenyl-4,5-dihydroimidazole Chemical compound C=CN1CCN=C1 HXVJQEGYAYABRY-UHFFFAOYSA-N 0.000 description 5
YPBVNVLJBHJIHK-UHFFFAOYSA-N 2-(2-methoxyethyl)-4,5-dihydro-1h-imidazole Chemical compound COCCC1=NCCN1 YPBVNVLJBHJIHK-UHFFFAOYSA-N 0.000 description 5
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
238000003482 Pinner synthesis reaction Methods 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000008367 deionised water Substances 0.000 description 5
229910021641 deionized water Inorganic materials 0.000 description 5
238000001914 filtration Methods 0.000 description 5
125000001841 imino group Chemical group [H]N=* 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000012071 phase Substances 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
229960001866 silicon dioxide Drugs 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
229940037003 alum Drugs 0.000 description 4
239000013078 crystal Substances 0.000 description 4
125000004185 ester group Chemical group 0.000 description 4
239000000499 gel Substances 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
229920002239 polyacrylonitrile Polymers 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
150000003440 styrenes Chemical class 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
239000002699 waste material Substances 0.000 description 4
RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 3
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000002159 abnormal effect Effects 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
239000007900 aqueous suspension Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
239000001110 calcium chloride Substances 0.000 description 3
229910001628 calcium chloride Inorganic materials 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
238000007334 copolymerization reaction Methods 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
229910001873 dinitrogen Inorganic materials 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000000835 fiber Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
230000004048 modification Effects 0.000 description 3
238000012986 modification Methods 0.000 description 3
239000000123 paper Substances 0.000 description 3
150000007519 polyprotic acids Polymers 0.000 description 3
239000000376 reactant Substances 0.000 description 3
230000009467 reduction Effects 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 3
238000005406 washing Methods 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
GRYSXUXXBDSYRT-WOUKDFQISA-N (2r,3r,4r,5r)-2-(hydroxymethyl)-4-methoxy-5-[6-(methylamino)purin-9-yl]oxolan-3-ol Chemical compound C1=NC=2C(NC)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1OC GRYSXUXXBDSYRT-WOUKDFQISA-N 0.000 description 2
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
FWILCLQEYMKQGO-UHFFFAOYSA-N 2-ethenyl-4,5-dihydro-1h-imidazole;hydrochloride Chemical compound Cl.C=CC1=NCCN1 FWILCLQEYMKQGO-UHFFFAOYSA-N 0.000 description 2
OOWFYDWAMOKVSF-UHFFFAOYSA-N 3-methoxypropanenitrile Chemical compound COCCC#N OOWFYDWAMOKVSF-UHFFFAOYSA-N 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
229910001006 Constantan Inorganic materials 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-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
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
125000003368 amide group Chemical group 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000012874 anionic emulsifier Substances 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
230000005587 bubbling Effects 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
125000002091 cationic group Chemical group 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
239000004927 clay Substances 0.000 description 2
229910000365 copper sulfate Inorganic materials 0.000 description 2
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
YVPJCJLMRRTDMQ-UHFFFAOYSA-N ethyl diazoacetate Chemical compound CCOC(=O)C=[N+]=[N-] YVPJCJLMRRTDMQ-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000012433 hydrogen halide Substances 0.000 description 2
229910000039 hydrogen halide Inorganic materials 0.000 description 2
239000005457 ice water Substances 0.000 description 2
230000006872 improvement Effects 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000002655 kraft paper Substances 0.000 description 2
229920002521 macromolecule Polymers 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
230000007246 mechanism Effects 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
229910001120 nichrome Inorganic materials 0.000 description 2
239000003921 oil Substances 0.000 description 2
238000012856 packing Methods 0.000 description 2
229920002401 polyacrylamide Polymers 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
239000002243 precursor Substances 0.000 description 2
YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 2
238000010526 radical polymerization reaction Methods 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
239000010801 sewage sludge Substances 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
229940095064 tartrate Drugs 0.000 description 2
239000006200 vaporizer Substances 0.000 description 2
BTANRVKWQNVYAZ-SCSAIBSYSA-N (2R)-butan-2-ol Chemical compound CC[C@@H](C)O BTANRVKWQNVYAZ-SCSAIBSYSA-N 0.000 description 1
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 description 1
BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
VFRMAHVDXYSEON-UHFFFAOYSA-N 1,1-diiodoethene Chemical compound IC(I)=C VFRMAHVDXYSEON-UHFFFAOYSA-N 0.000 description 1
WVAFEFUPWRPQSY-UHFFFAOYSA-N 1,2,3-tris(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1C=C WVAFEFUPWRPQSY-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
238000011925 1,2-addition Methods 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical class ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
UCVSGJVQGIBHQA-UHFFFAOYSA-N 1-ethenyldibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C=C UCVSGJVQGIBHQA-UHFFFAOYSA-N 0.000 description 1
CRVBQABBEKLFIN-UHFFFAOYSA-N 1-phenylethane-1,2-diamine Chemical compound NCC(N)C1=CC=CC=C1 CRVBQABBEKLFIN-UHFFFAOYSA-N 0.000 description 1
SDPNMKBPWRAPHY-UHFFFAOYSA-N 1-prop-2-enylazepan-2-one Chemical compound C=CCN1CCCCCC1=O SDPNMKBPWRAPHY-UHFFFAOYSA-N 0.000 description 1
IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
SXZSFWHOSHAKMN-UHFFFAOYSA-N 2,3,4,4',5-Pentachlorobiphenyl Chemical compound C1=CC(Cl)=CC=C1C1=CC(Cl)=C(Cl)C(Cl)=C1Cl SXZSFWHOSHAKMN-UHFFFAOYSA-N 0.000 description 1
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Landscapes

Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA226,547A 1975-05-08 1975-05-08 Imidazolines non saturees Expired CA1039727A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA226,547A CA1039727A (fr)	1975-05-08	1975-05-08	Imidazolines non saturees

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA226,547A CA1039727A (fr)	1975-05-08	1975-05-08	Imidazolines non saturees

Publications (1)

Publication Number	Publication Date
CA1039727A true CA1039727A (fr)	1978-10-03

Family

ID=4103036

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA226,547A Expired CA1039727A (fr)	1975-05-08	1975-05-08	Imidazolines non saturees

Country Status (1)

Country	Link
CA (1)	CA1039727A (fr)

1975
- 1975-05-08 CA CA226,547A patent/CA1039727A/fr not_active Expired

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