CA1217195A - Polymerizable imidazolidinones and polymers thereof useful as nonwoven binders - Google Patents
Polymerizable imidazolidinones and polymers thereof useful as nonwoven bindersInfo
- Publication number
- CA1217195A CA1217195A CA000448724A CA448724A CA1217195A CA 1217195 A CA1217195 A CA 1217195A CA 000448724 A CA000448724 A CA 000448724A CA 448724 A CA448724 A CA 448724A CA 1217195 A CA1217195 A CA 1217195A
- Authority
- CA
- Canada
- Prior art keywords
- hydrogen
- group
- polymer
- methyl
- monomer
- 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
- 229920000642 polymer Polymers 0.000 title claims abstract description 73
- 239000011230 binding agent Substances 0.000 title claims abstract description 20
- 150000008624 imidazolidinones Chemical class 0.000 title abstract description 4
- 239000000178 monomer Substances 0.000 claims abstract description 75
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims abstract description 39
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000000839 emulsion Substances 0.000 claims abstract description 23
- 238000004132 cross linking Methods 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 239000004753 textile Substances 0.000 claims abstract description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims description 103
- 229910052739 hydrogen Inorganic materials 0.000 claims description 103
- 239000000203 mixture Substances 0.000 claims description 58
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 13
- 239000005977 Ethylene Substances 0.000 claims description 13
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 12
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 12
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 33
- 150000002431 hydrogen Chemical class 0.000 claims 26
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 9
- 239000002954 polymerization reaction product Substances 0.000 claims 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 230000002378 acidificating effect Effects 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 17
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract description 3
- 235000005074 zinc chloride Nutrition 0.000 abstract description 2
- 239000011592 zinc chloride Substances 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 31
- 229920000126 latex Polymers 0.000 description 26
- 239000004816 latex Substances 0.000 description 25
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- 239000007787 solid Substances 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000012153 distilled water Substances 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 229940015043 glyoxal Drugs 0.000 description 18
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000004202 carbamide Substances 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 235000019256 formaldehyde Nutrition 0.000 description 8
- 229960004279 formaldehyde Drugs 0.000 description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- 238000013019 agitation Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- -1 isocyanate compound Chemical class 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical class CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 4
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 208000036366 Sensation of pressure Diseases 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 229940031575 hydroxyethyl urea Drugs 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 2
- 229920000847 nonoxynol Polymers 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 238000007039 two-step reaction Methods 0.000 description 2
- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical class ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- FCTDKZOUZXYHNA-UHFFFAOYSA-N 1,4-dioxane-2,2-diol Chemical compound OC1(O)COCCO1 FCTDKZOUZXYHNA-UHFFFAOYSA-N 0.000 description 1
- QTHAGKAIWAFSTK-UHFFFAOYSA-N 1-butyl-3-(2-methylprop-1-enyl)urea Chemical compound CCCCNC(=O)NC=C(C)C QTHAGKAIWAFSTK-UHFFFAOYSA-N 0.000 description 1
- FHMCSBQYULQGHO-UHFFFAOYSA-N 1-butyl-4,5-dihydroxy-3-(2-methylprop-1-enyl)imidazolidin-2-one Chemical compound CCCCN1C(O)C(O)N(C=C(C)C)C1=O FHMCSBQYULQGHO-UHFFFAOYSA-N 0.000 description 1
- DHMUKVXMPOZDFZ-UHFFFAOYSA-N 1-ethenyl-3-ethyl-4,5-dihydroxyimidazolidin-2-one Chemical compound CCN1C(O)C(O)N(C=C)C1=O DHMUKVXMPOZDFZ-UHFFFAOYSA-N 0.000 description 1
- LIOYFPXDFZHOGN-UHFFFAOYSA-N 1-ethenyl-3-ethylurea Chemical compound CCNC(=O)NC=C LIOYFPXDFZHOGN-UHFFFAOYSA-N 0.000 description 1
- BDSPTFQIOAEIII-UHFFFAOYSA-N 2,3,4a,6,7,8a-hexahydro-[1,4]dioxino[2,3-b][1,4]dioxine-2,3,6,7-tetrol Chemical compound O1C(O)C(O)OC2OC(O)C(O)OC21 BDSPTFQIOAEIII-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- UDVMOLFILHAVTD-UHFFFAOYSA-N 2-(4,5-dihydroxy-2-oxoimidazolidin-1-yl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCN1C(O)C(O)NC1=O UDVMOLFILHAVTD-UHFFFAOYSA-N 0.000 description 1
- ITSQZSJBXQCZOY-UHFFFAOYSA-N 2-(methylcarbamoylamino)ethyl 2-methylprop-2-enoate Chemical compound CNC(=O)NCCOC(=O)C(C)=C ITSQZSJBXQCZOY-UHFFFAOYSA-N 0.000 description 1
- PUYYWYBVKOKOPQ-UHFFFAOYSA-N 4,5-dihydroxy-1-[2-(2-hydroxy-1-prop-1-enoxypropoxy)ethyl]imidazolidin-2-one Chemical compound CC=COC(C(C)O)OCCN1C(O)C(O)NC1=O PUYYWYBVKOKOPQ-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- XTCDFSKSJGZXMZ-UHFFFAOYSA-N C(C(=C)C)(=O)OC(CN1C(NC(C1O)O)=O)OCC(C)O Chemical compound C(C(=C)C)(=O)OC(CN1C(NC(C1O)O)=O)OCC(C)O XTCDFSKSJGZXMZ-UHFFFAOYSA-N 0.000 description 1
- PGBQLBGVYPUBIM-UHFFFAOYSA-N C(C(=C)C)(=O)OC(CNC(=O)N)OCC(C)O Chemical compound C(C(=C)C)(=O)OC(CNC(=O)N)OCC(C)O PGBQLBGVYPUBIM-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 1
- 102100038916 Caspase-5 Human genes 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 101100112336 Homo sapiens CASP5 gene Proteins 0.000 description 1
- 101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 101100273286 Mus musculus Casp4 gene Proteins 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229940043379 ammonium hydroxide Drugs 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- RNOOHTVUSNIPCJ-UHFFFAOYSA-N butan-2-yl prop-2-enoate Chemical compound CCC(C)OC(=O)C=C RNOOHTVUSNIPCJ-UHFFFAOYSA-N 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 238000009960 carding Methods 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- RZMWTGFSAMRLQH-UHFFFAOYSA-L disodium;2,2-dihexyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCC RZMWTGFSAMRLQH-UHFFFAOYSA-L 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002706 dry binder Substances 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000675 fabric finishing Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009962 finishing (textile) Methods 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 150000002238 fumaric acids Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940096419 glyoxal trimer Drugs 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- JCYWCSGERIELPG-UHFFFAOYSA-N imes Chemical class CC1=CC(C)=CC(C)=C1N1C=CN(C=2C(=CC(C)=CC=2C)C)[C]1 JCYWCSGERIELPG-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F26/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F26/06—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/40—Two or more oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US47392283A | 1983-03-10 | 1983-03-10 | |
| US473,922 | 1983-03-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1217195A true CA1217195A (en) | 1987-01-27 |
Family
ID=23881556
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000448724A Expired CA1217195A (en) | 1983-03-10 | 1984-03-02 | Polymerizable imidazolidinones and polymers thereof useful as nonwoven binders |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0124713B1 (enExample) |
| JP (2) | JPS59170072A (enExample) |
| AU (1) | AU542695B2 (enExample) |
| CA (1) | CA1217195A (enExample) |
| DE (1) | DE3474019D1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3344912A1 (de) * | 1983-12-13 | 1985-06-20 | Hoechst Ag, 6230 Frankfurt | Vernetzte polymerisate, verfahren zu ihrer herstellung und ihre anwendung |
| DE3504337A1 (de) * | 1985-02-08 | 1986-08-14 | Hoechst Ag, 6230 Frankfurt | Haertbare copolymerisate, verfahren zu ihrer herstellung und ihre verwendung |
| EP0206455B1 (en) * | 1985-04-24 | 1990-07-04 | Texaco Development Corporation | Polymers of ethylenically unsaturated compounds, and lubricating oil containing said polymers as viscosity index improvers |
| FR2655987B1 (fr) * | 1989-12-15 | 1992-03-27 | Norsolor Sa | Procede de preparation de (meth)acrylate d'alkylimidazolidone. |
| DE4010532A1 (de) * | 1990-04-02 | 1991-10-10 | Roehm Gmbh | Verfahren zur herstellung von endstaendig heterocyclus-substituierten acryl- und methacrylsaeurealkylestern |
| DE69726160T2 (de) | 1996-06-24 | 2004-08-26 | Cytec Technology Corp., Wilmington | Neue polymerisierbare acylimidazolidinonmonomere |
| WO1997049687A1 (en) * | 1996-06-24 | 1997-12-31 | Cytec Technology Corp. | Polyfunctional crosslinking acylimidazolidinone derivatives |
| DE19850363A1 (de) | 1998-11-02 | 2000-05-04 | Basf Ag | Polymere für kosmetische Formulierungen |
| US7947766B2 (en) | 2003-06-06 | 2011-05-24 | The Procter & Gamble Company | Crosslinking systems for hydroxyl polymers |
| US6955850B1 (en) | 2004-04-29 | 2005-10-18 | The Procter & Gamble Company | Polymeric structures and method for making same |
| US6977116B2 (en) | 2004-04-29 | 2005-12-20 | The Procter & Gamble Company | Polymeric structures and method for making same |
| WO2007100047A1 (ja) * | 2006-03-02 | 2007-09-07 | Ube Industries, Ltd. | ２－イミダゾリジノン化合物及び４，５－ジアルコキシ－２－イミダゾリジノン化合物の製造方法 |
| US7565721B2 (en) | 2006-03-30 | 2009-07-28 | Ykk Corporation | Non-rotating sandwich button |
| JP6953194B2 (ja) * | 2017-06-09 | 2021-10-27 | キヤノン株式会社 | 重合体 |
-
1984
- 1984-03-02 CA CA000448724A patent/CA1217195A/en not_active Expired
- 1984-03-08 DE DE8484102500T patent/DE3474019D1/de not_active Expired
- 1984-03-08 EP EP84102500A patent/EP0124713B1/en not_active Expired
- 1984-03-09 AU AU25444/84A patent/AU542695B2/en not_active Ceased
- 1984-03-10 JP JP4486084A patent/JPS59170072A/ja active Granted
-
1986
- 1986-12-03 JP JP28687886A patent/JPS62161807A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62161807A (ja) | 1987-07-17 |
| JPS59170072A (ja) | 1984-09-26 |
| AU2544484A (en) | 1984-09-13 |
| EP0124713A2 (en) | 1984-11-14 |
| EP0124713A3 (en) | 1986-05-28 |
| JPH0343288B2 (enExample) | 1991-07-02 |
| EP0124713B1 (en) | 1988-09-14 |
| DE3474019D1 (en) | 1988-10-20 |
| JPS6234757B2 (enExample) | 1987-07-28 |
| AU542695B2 (en) | 1985-03-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1217195A (en) | Polymerizable imidazolidinones and polymers thereof useful as nonwoven binders | |
| US3349121A (en) | Process of reacting together unsaturated amides, formaldehyde, and secondary amines and the products formed thereby | |
| US4577031A (en) | Polymerizable imidazolidinones | |
| US2871223A (en) | Polymers, copolymers, and processes for preparing them | |
| AU639357B2 (en) | Aqueous dispersions of fluorine-containing polymers | |
| US5659011A (en) | Agents having high nitrogen content and high cationic charge based on dicyanimide dicyandiamide or guanidine and inorganic ammonium salts | |
| US3008851A (en) | Novel quaternary ammonium compounds and methods of producing them | |
| US4622374A (en) | Imidazolidinone polymers useful as nonwoven binders | |
| US4596850A (en) | Imidazolidinone polymers useful as nonwoven binders | |
| US5427859A (en) | Fluoroorganic soil-resist agents | |
| US4760152A (en) | Pyrrolidonyl acrylate block polymers | |
| US2734890A (en) | Ureidoalkyl vinyl ethers | |
| JPH0629226B2 (ja) | 自己−及びジオ−ル反応性の架橋性モノマ−類及びそれらから誘導されるポリマ− | |
| JPS62227435A (ja) | 新規界面活性剤 | |
| WO1997049686A1 (en) | Novel polymerizable acyl imidazolidinone monomers | |
| US2651631A (en) | Ethylene imine-acrylyl triazine reaction products | |
| US3146228A (en) | Nu, nu'-ethylene bis[p, p-bis(1-aziridinyl)-nu-methyl phosphinic amide] and homopolymer thereof | |
| US5177263A (en) | N-allyl-N-dialkoxyethyl amide or amine monomers | |
| US2300570A (en) | Method of preparing alkylol cyanamide condensation products | |
| US2800417A (en) | Printing paste and method of printing textiles therewith | |
| US2615888A (en) | Reaction products of nitreles | |
| US3185539A (en) | Process of treating cellulose textiles with certain alkylenebis(n-carboxamides) and products produced therefrom | |
| US2727015A (en) | Polymeric n,n'-alkyleneureidoalkyl acrylamides and process for producing them by aminolysis | |
| US3350363A (en) | Nu-(acylamidoalkyl)-nu'-vinyl-nu, nu'-alkyleneureas, polymers thereof and methods of making them | |
| US3784641A (en) | N,n-bis alkoxymethyl and n,n-dimethylol sulfonamides |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |