SE456912B - Vattenloesliga polyamidoaminpolyamin och foerfarande foer framstaellning av en cellulosafiberbaserad arkprodukt - Google Patents
Vattenloesliga polyamidoaminpolyamin och foerfarande foer framstaellning av en cellulosafiberbaserad arkproduktInfo
- Publication number
- SE456912B SE456912B SE8403075A SE8403075A SE456912B SE 456912 B SE456912 B SE 456912B SE 8403075 A SE8403075 A SE 8403075A SE 8403075 A SE8403075 A SE 8403075A SE 456912 B SE456912 B SE 456912B
- Authority
- SE
- Sweden
- Prior art keywords
- polyamine
- product
- polyamidoamine
- molecular weight
- reaction
- Prior art date
Links
- 229920000768 polyamine Polymers 0.000 title claims description 129
- 238000000034 method Methods 0.000 title claims description 12
- 239000000835 fiber Substances 0.000 title claims description 8
- 239000000047 product Substances 0.000 claims description 112
- 229920000962 poly(amidoamine) Polymers 0.000 claims description 99
- 239000000463 material Substances 0.000 claims description 48
- 238000007056 transamidation reaction Methods 0.000 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 150000001412 amines Chemical class 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 25
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 23
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 15
- 125000001931 aliphatic group Chemical group 0.000 claims description 14
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 14
- -1 aliphatic saturated dicarboxylic acid Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 9
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- 125000001302 tertiary amino group Chemical group 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 239000007859 condensation product Substances 0.000 claims description 5
- 239000000945 filler Substances 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 239000000049 pigment Substances 0.000 claims description 4
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002002 slurry Substances 0.000 claims 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 1
- NHWGPUVJQFTOQX-UHFFFAOYSA-N ethyl-[2-[2-[ethyl(dimethyl)azaniumyl]ethyl-methylamino]ethyl]-dimethylazanium Chemical compound CC[N+](C)(C)CCN(C)CC[N+](C)(C)CC NHWGPUVJQFTOQX-UHFFFAOYSA-N 0.000 claims 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims 1
- 230000014759 maintenance of location Effects 0.000 description 32
- 239000000123 paper Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 125000003368 amide group Chemical group 0.000 description 9
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- 238000005227 gel permeation chromatography Methods 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 229920002873 Polyethylenimine Polymers 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 239000004952 Polyamide Substances 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000003776 cleavage reaction Methods 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229920002647 polyamide Polymers 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 230000007017 scission Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 4
- 235000011037 adipic acid Nutrition 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000005891 transamination reaction Methods 0.000 description 3
- 229960001124 trientine Drugs 0.000 description 3
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000013051 drainage agent Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000005188 flotation Methods 0.000 description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000013383 initial experiment Methods 0.000 description 2
- 150000003951 lactams Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012434 nucleophilic reagent Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 2
- 238000012958 reprocessing Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011122 softwood Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- JEQDSBVHLKBEIZ-REOHCLBHSA-N (2s)-2-chloropropanoyl chloride Chemical compound C[C@H](Cl)C(Cl)=O JEQDSBVHLKBEIZ-REOHCLBHSA-N 0.000 description 1
- HFBHOAHFRNLZGN-LURJTMIESA-N (2s)-2-formamido-4-methylpentanoic acid Chemical compound CC(C)C[C@@H](C(O)=O)NC=O HFBHOAHFRNLZGN-LURJTMIESA-N 0.000 description 1
- 125000006557 (C2-C5) alkylene group Chemical group 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- YHRUOJUYPBUZOS-UHFFFAOYSA-N 1,3-dichloropropane Chemical compound ClCCCCl YHRUOJUYPBUZOS-UHFFFAOYSA-N 0.000 description 1
- OVISMSJCKCDOPU-UHFFFAOYSA-N 1,6-dichlorohexane Chemical compound ClCCCCCCCl OVISMSJCKCDOPU-UHFFFAOYSA-N 0.000 description 1
- FYBFGAFWCBMEDG-UHFFFAOYSA-N 1-[3,5-di(prop-2-enoyl)-1,3,5-triazinan-1-yl]prop-2-en-1-one Chemical compound C=CC(=O)N1CN(C(=O)C=C)CN(C(=O)C=C)C1 FYBFGAFWCBMEDG-UHFFFAOYSA-N 0.000 description 1
- XAZDZMUGHYYPQM-UHFFFAOYSA-N 1-chloro-3-(3-chloro-2-hydroxypropoxy)propan-2-ol Chemical class ClCC(O)COCC(O)CCl XAZDZMUGHYYPQM-UHFFFAOYSA-N 0.000 description 1
- PVBMXMKIKMJQRK-UHFFFAOYSA-N 1-chloro-4-(4-chlorobutoxy)butane Chemical compound ClCCCCOCCCCCl PVBMXMKIKMJQRK-UHFFFAOYSA-N 0.000 description 1
- MSSMDWAXCNWOGU-UHFFFAOYSA-N 2-(dichloromethyl)-3-methyloxirane Chemical compound CC1OC1C(Cl)Cl MSSMDWAXCNWOGU-UHFFFAOYSA-N 0.000 description 1
- SVDDJQGVOFZBNX-UHFFFAOYSA-N 2-chloroethyl carbonochloridate Chemical compound ClCCOC(Cl)=O SVDDJQGVOFZBNX-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 1
- KRPRVQWGKLEFKN-UHFFFAOYSA-N 3-(3-aminopropoxy)propan-1-amine Chemical compound NCCCOCCCN KRPRVQWGKLEFKN-UHFFFAOYSA-N 0.000 description 1
- QPIOXOJERGNNMX-UHFFFAOYSA-N 3-(3-aminopropylsulfanyl)propan-1-amine Chemical compound NCCCSCCCN QPIOXOJERGNNMX-UHFFFAOYSA-N 0.000 description 1
- FRXLFVNGTPQFEJ-UHFFFAOYSA-N 3-bromopropanoyl bromide Chemical compound BrCCC(Br)=O FRXLFVNGTPQFEJ-UHFFFAOYSA-N 0.000 description 1
- LFEAJBLOEPTINE-UHFFFAOYSA-N 4-(chloromethyl)-1,3-dioxolan-2-one Chemical compound ClCC1COC(=O)O1 LFEAJBLOEPTINE-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- UQXNEWQGGVUVQA-UHFFFAOYSA-N 8-aminooctanoic acid Chemical compound NCCCCCCCC(O)=O UQXNEWQGGVUVQA-UHFFFAOYSA-N 0.000 description 1
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- ZFIVKAOQEXOYFY-UHFFFAOYSA-N Diepoxybutane Chemical compound C1OC1C1OC1 ZFIVKAOQEXOYFY-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 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
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- MHTONRWSEQKWDM-UHFFFAOYSA-N N'-[[3-[(3-aminopropylamino)methyl]phenyl]methyl]propane-1,3-diamine Chemical compound NCCCNCC1=CC(=CC=C1)CNCCCN MHTONRWSEQKWDM-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
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- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
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- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
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- 238000007098 aminolysis reaction Methods 0.000 description 1
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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- BELZJFWUNQWBES-UHFFFAOYSA-N caldopentamine Chemical compound NCCCNCCCNCCCNCCCN BELZJFWUNQWBES-UHFFFAOYSA-N 0.000 description 1
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- 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
- AQGNVWRYTKPRMR-UHFFFAOYSA-N n'-[2-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCNCCN AQGNVWRYTKPRMR-UHFFFAOYSA-N 0.000 description 1
- DYUCNAMTUNGLAB-UHFFFAOYSA-N n,n'-bis(2-aminoethyl)hexane-1,6-diamine Chemical compound NCCNCCCCCCNCCN DYUCNAMTUNGLAB-UHFFFAOYSA-N 0.000 description 1
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920000333 poly(propyleneimine) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000867 polyelectrolyte Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003330 sebacic acids Chemical class 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910001388 sodium aluminate Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 1
- 229960003986 tuaminoheptane Drugs 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/54—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen
- D21H17/55—Polyamides; Polyaminoamides; Polyester-amides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/48—Polymers modified by chemical after-treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
- Paper (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50255183A | 1983-06-09 | 1983-06-09 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8403075D0 SE8403075D0 (sv) | 1984-06-07 |
| SE8403075L SE8403075L (sv) | 1984-12-10 |
| SE456912B true SE456912B (sv) | 1988-11-14 |
Family
ID=23998324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8403075A SE456912B (sv) | 1983-06-09 | 1984-06-07 | Vattenloesliga polyamidoaminpolyamin och foerfarande foer framstaellning av en cellulosafiberbaserad arkprodukt |
Country Status (12)
| Country | Link |
|---|---|
| JP (2) | JPH0610264B2 (it) |
| AT (1) | AT385276B (it) |
| BE (1) | BE899880A (it) |
| BR (1) | BR8402805A (it) |
| CH (1) | CH663792A5 (it) |
| DE (1) | DE3421557A1 (it) |
| FR (1) | FR2547303B1 (it) |
| GB (1) | GB2141130B (it) |
| IT (1) | IT1180183B (it) |
| NL (1) | NL8401825A (it) |
| NO (1) | NO161378C (it) |
| SE (1) | SE456912B (it) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62104725A (ja) * | 1985-10-31 | 1987-05-15 | Meiki Co Ltd | 真空引きベント式射出成形機 |
| JPS62124923A (ja) * | 1985-11-26 | 1987-06-06 | Kishimoto Sangyo Kk | 改良されたベント式射出成形機 |
| US5223097A (en) * | 1986-01-09 | 1993-06-29 | W. R. Grace Ab | Method for controlling pitch on a paper-making machine |
| US5626720A (en) * | 1986-01-09 | 1997-05-06 | W.R. Grace & Co.-Conn. | Method for controlling pitch on a papermaking machine |
| US4722964A (en) * | 1986-06-20 | 1988-02-02 | Borden, Inc. | Epoxidized polyalkyleneamine-amide wet strength resin |
| DE3721057C2 (de) * | 1987-06-26 | 1996-08-22 | Bayer Ag | Wasserlösliche, basische Polykondensate, Verfahren zu ihrer Herstellung, diese enthaltende Retentionsmittel und ihre Verwendung zur Herstellung von Papier |
| GB2254345B (en) * | 1991-03-28 | 1995-06-14 | Grace W R & Co | Creping aid |
| TW334493B (en) * | 1996-05-14 | 1998-06-21 | Sugatsune Kogyo | Damper for opening or closing a door |
| PL2121806T3 (pl) * | 2007-01-19 | 2015-08-31 | Solenis Tech Cayman Lp | Sposób wytwarzania środków adhezyjnych do krepowania wytworzonych z poliamidoamin zakończonych grupą aminową |
| US20120247697A1 (en) * | 2011-03-29 | 2012-10-04 | Kemira Oyj | Polyamine Polyamidoamine Epihaloohydrin Compositions and Processes for Preparing and Using the Same |
| WO2013046060A1 (en) | 2011-09-30 | 2013-04-04 | Kemira Oyj | Paper and methods of making paper |
| US9777434B2 (en) | 2011-12-22 | 2017-10-03 | Kemira Dyj | Compositions and methods of making paper products |
| WO2013179139A1 (en) * | 2012-05-30 | 2013-12-05 | Kemira Oyj | Compositions and methods of making paper products |
| CA2886043A1 (en) * | 2012-09-26 | 2014-04-03 | Kemira Oyj | Absorbent materials, products including absorbent materials, compositions, and methods of making absorbent materials |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1771043C3 (de) * | 1968-03-27 | 1979-05-23 | Bayer Ag, 5090 Leverkusen | Selbstvernetzende wasserlösliche Produkte und deren Verwendung als Naßfestmittel für Papier |
| DE1802435C3 (de) * | 1968-10-11 | 1979-01-18 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von vernetzten Harzen auf der Basis von basischen Polyamidoaminen und deren Verwendung als Entwässerungs-, Retentions- und Flockungsmittel bei der Papierherstellung |
| US3793279A (en) * | 1972-11-08 | 1974-02-19 | Diamond Shamrock Corp | Mono primary polyamine and organic dihalide modified,epoxidized polyamide for paper wet strength resin |
| DE2736651A1 (de) * | 1977-08-13 | 1979-02-15 | Wolff Walsrode Ag | Hilfsmittel zur verbesserung der retention, entwaesserung und aufbereitung, insbesondere bei der papierherstellung |
| DE2756469A1 (de) * | 1977-12-17 | 1979-06-21 | Bayer Ag | Amidgruppenhaltige polyamine |
| DE2756431C2 (de) * | 1977-12-17 | 1985-05-15 | Bayer Ag, 5090 Leverkusen | Amidgruppenhaltige Polyamine |
| DE2949870A1 (de) * | 1979-12-12 | 1981-06-19 | Hoechst Ag, 6230 Frankfurt | Kondensationsprodukte zur erhoehung der nassfestigkeit von papier |
| JPS6046130B2 (ja) * | 1981-03-30 | 1985-10-14 | 星光化学工業株式会社 | 製紙用添加剤の製造法 |
| DE3135830A1 (de) * | 1981-09-10 | 1983-03-24 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von wasserloeslichen, stickstoffhaltigen kondensationsprodukten und deren verwendung bei der papierherstellung |
| JPS60150894A (ja) * | 1984-01-20 | 1985-08-08 | Nishihara Environ Sanit Res Corp | バツチ式活性汚泥処理装置 |
| JPH03199546A (ja) * | 1989-12-27 | 1991-08-30 | Meiwa Kk | 電波シールドパネル構造体 |
| JP3008839U (ja) * | 1994-06-01 | 1995-03-20 | 株式会社エポック社 | バーコードサッカーゲーム機 |
-
1984
- 1984-06-05 GB GB08414268A patent/GB2141130B/en not_active Expired
- 1984-06-07 SE SE8403075A patent/SE456912B/sv not_active IP Right Cessation
- 1984-06-07 DE DE19843421557 patent/DE3421557A1/de not_active Withdrawn
- 1984-06-08 JP JP59116769A patent/JPH0610264B2/ja not_active Expired - Lifetime
- 1984-06-08 FR FR8409043A patent/FR2547303B1/fr not_active Expired
- 1984-06-08 IT IT21332/84A patent/IT1180183B/it active
- 1984-06-08 NL NL8401825A patent/NL8401825A/nl not_active Application Discontinuation
- 1984-06-08 NO NO842328A patent/NO161378C/no unknown
- 1984-06-08 BE BE0/213114A patent/BE899880A/fr not_active IP Right Cessation
- 1984-06-08 BR BR8402805A patent/BR8402805A/pt unknown
- 1984-06-08 CH CH2816/84A patent/CH663792A5/de not_active IP Right Cessation
- 1984-06-12 AT AT0191984A patent/AT385276B/de active
-
1993
- 1993-08-02 JP JP5208150A patent/JPH0713357B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0610264B2 (ja) | 1994-02-09 |
| NO161378C (no) | 1989-08-09 |
| CH663792A5 (de) | 1988-01-15 |
| ATA191984A (de) | 1987-08-15 |
| NO842328L (no) | 1984-12-10 |
| AT385276B (de) | 1988-03-10 |
| GB2141130A (en) | 1984-12-12 |
| NL8401825A (nl) | 1985-01-02 |
| GB8414268D0 (en) | 1984-07-11 |
| JPH06240597A (ja) | 1994-08-30 |
| NO161378B (no) | 1989-05-02 |
| SE8403075D0 (sv) | 1984-06-07 |
| DE3421557A1 (de) | 1985-01-10 |
| FR2547303A1 (fr) | 1984-12-14 |
| JPS6018528A (ja) | 1985-01-30 |
| GB2141130B (en) | 1986-11-12 |
| SE8403075L (sv) | 1984-12-10 |
| IT8421332A0 (it) | 1984-06-08 |
| FR2547303B1 (fr) | 1988-03-18 |
| JPH0713357B2 (ja) | 1995-02-15 |
| IT1180183B (it) | 1987-09-23 |
| BR8402805A (pt) | 1985-05-21 |
| BE899880A (fr) | 1984-12-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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