DE2302439A1 - Harze fuer wasserfeste papiere - Google Patents
Harze fuer wasserfeste papiereInfo
- Publication number
- DE2302439A1 DE2302439A1 DE2302439A DE2302439A DE2302439A1 DE 2302439 A1 DE2302439 A1 DE 2302439A1 DE 2302439 A DE2302439 A DE 2302439A DE 2302439 A DE2302439 A DE 2302439A DE 2302439 A1 DE2302439 A1 DE 2302439A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- carbon atoms
- base
- temperature
- alkyl
- 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.)
- Pending
Links
- 239000011347 resin Substances 0.000 title claims description 120
- 229920005989 resin Polymers 0.000 title claims description 120
- 239000002253 acid Substances 0.000 claims description 98
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 75
- 125000004432 carbon atom Chemical group C* 0.000 claims description 50
- 229920000768 polyamine Polymers 0.000 claims description 48
- 239000004952 Polyamide Substances 0.000 claims description 41
- 229920002647 polyamide Polymers 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- 239000003795 chemical substances by application Substances 0.000 claims description 23
- 150000002148 esters Chemical class 0.000 claims description 21
- 229920006395 saturated elastomer Polymers 0.000 claims description 20
- -1 (aminopropyl) - Chemical class 0.000 claims description 18
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 17
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical group NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 239000004970 Chain extender Substances 0.000 claims description 12
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 12
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 11
- 150000005690 diesters Chemical class 0.000 claims description 11
- 239000004593 Epoxy Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 230000000911 decarboxylating effect Effects 0.000 claims description 10
- 125000001302 tertiary amino group Chemical group 0.000 claims description 10
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- AGYUOJIYYGGHKV-UHFFFAOYSA-N 1,2-bis(2-chloroethoxy)ethane Chemical compound ClCCOCCOCCCl AGYUOJIYYGGHKV-UHFFFAOYSA-N 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 239000011149 active material Substances 0.000 claims description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims description 6
- 238000006735 epoxidation reaction Methods 0.000 claims description 6
- 150000003901 oxalic acid esters Chemical class 0.000 claims description 6
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims description 6
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 5
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 150000003628 tricarboxylic acids Chemical class 0.000 claims description 5
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 claims description 4
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 4
- 229920001131 Pulp (paper) Polymers 0.000 claims description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 4
- 150000005215 alkyl ethers Chemical class 0.000 claims description 4
- 150000001350 alkyl halides Chemical class 0.000 claims description 4
- 239000006227 byproduct Substances 0.000 claims description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 claims description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 4
- QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 claims description 3
- 239000001361 adipic acid Substances 0.000 claims description 3
- 235000011037 adipic acid Nutrition 0.000 claims description 3
- 239000007900 aqueous suspension Substances 0.000 claims description 3
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 claims description 3
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 claims description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 2
- JDRMYOQETPMYQX-UHFFFAOYSA-M 4-methoxy-4-oxobutanoate Chemical compound COC(=O)CCC([O-])=O JDRMYOQETPMYQX-UHFFFAOYSA-M 0.000 claims description 2
- QCFYJCYNJLBDRT-UHFFFAOYSA-N Bis(2-chloro-1-methylethyl)ether Chemical compound ClCC(C)OC(C)CCl QCFYJCYNJLBDRT-UHFFFAOYSA-N 0.000 claims description 2
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 claims description 2
- JDRMYOQETPMYQX-UHFFFAOYSA-N butanedioic acid monomethyl ester Natural products COC(=O)CCC(O)=O JDRMYOQETPMYQX-UHFFFAOYSA-N 0.000 claims description 2
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical group BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 claims description 2
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 claims description 2
- XTDYIOOONNVFMA-UHFFFAOYSA-N dimethyl pentanedioate Chemical compound COC(=O)CCCC(=O)OC XTDYIOOONNVFMA-UHFFFAOYSA-N 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 229940014800 succinic anhydride Drugs 0.000 claims description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 2
- 235000011090 malic acid Nutrition 0.000 claims 2
- 229940099690 malic acid Drugs 0.000 claims 2
- 239000001630 malic acid Substances 0.000 claims 2
- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 claims 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims 1
- UOBSVARXACCLLH-UHFFFAOYSA-N monomethyl adipate Chemical compound COC(=O)CCCCC(O)=O UOBSVARXACCLLH-UHFFFAOYSA-N 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 239000000123 paper Substances 0.000 description 51
- 238000006243 chemical reaction Methods 0.000 description 38
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 34
- 150000007513 acids Chemical class 0.000 description 31
- 230000015572 biosynthetic process Effects 0.000 description 20
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 13
- 235000019441 ethanol Nutrition 0.000 description 11
- 150000002500 ions Chemical class 0.000 description 11
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- 230000032683 aging Effects 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000003786 synthesis reaction Methods 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
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 150000001261 hydroxy acids Chemical class 0.000 description 3
- 210000003734 kidney Anatomy 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 239000010893 paper waste Substances 0.000 description 3
- 229920001281 polyalkylene Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 229960001124 trientine Drugs 0.000 description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- OIFAHDAXIUURLN-UHFFFAOYSA-N 2-(fluoromethyl)oxirane Chemical compound FCC1CO1 OIFAHDAXIUURLN-UHFFFAOYSA-N 0.000 description 1
- AGIBHMPYXXPGAX-UHFFFAOYSA-N 2-(iodomethyl)oxirane Chemical compound ICC1CO1 AGIBHMPYXXPGAX-UHFFFAOYSA-N 0.000 description 1
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 1
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- TUGYYYCKWFHYSY-UHFFFAOYSA-N 2-bromo-3-ethyloxirane Chemical compound CCC1OC1Br TUGYYYCKWFHYSY-UHFFFAOYSA-N 0.000 description 1
- DVDZAXAAZHLRQH-UHFFFAOYSA-N 2-butyl-3-chlorooxirane Chemical compound CCCCC1OC1Cl DVDZAXAAZHLRQH-UHFFFAOYSA-N 0.000 description 1
- MUKMSDKKSSBIAD-UHFFFAOYSA-N 2-hept-3-enylpropanedioic acid Chemical compound CCCC=CCCC(C(O)=O)C(O)=O MUKMSDKKSSBIAD-UHFFFAOYSA-N 0.000 description 1
- JDTUPLBMGDDPJS-UHFFFAOYSA-N 2-methoxy-2-phenylethanol Chemical compound COC(CO)C1=CC=CC=C1 JDTUPLBMGDDPJS-UHFFFAOYSA-N 0.000 description 1
- WMRCTEPOPAZMMN-UHFFFAOYSA-N 2-undecylpropanedioic acid Chemical compound CCCCCCCCCCCC(C(O)=O)C(O)=O WMRCTEPOPAZMMN-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 241000282979 Alces alces Species 0.000 description 1
- 241001471112 Artocarpus tamaran Species 0.000 description 1
- RHXPAKJZPMGZQK-UHFFFAOYSA-N C(C=C/C(=O)O)(=O)O.C1(CCC(=O)O1)=O Chemical compound C(C=C/C(=O)O)(=O)O.C1(CCC(=O)O1)=O RHXPAKJZPMGZQK-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical class CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- NLNWWWDKCLQVNS-UHFFFAOYSA-N N-hexyl-6-iminohexan-1-amine Chemical group N=CCCCCCNCCCCCC NLNWWWDKCLQVNS-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
- 229940067597 azelate Drugs 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 229920005565 cyclic polymer Polymers 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- ZVRONEHXTIBGIQ-UHFFFAOYSA-N didecyl octanedioate Chemical compound CCCCCCCCCCOC(=O)CCCCCCC(=O)OCCCCCCCCCC ZVRONEHXTIBGIQ-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- KLEPMTZPTNHHOW-UHFFFAOYSA-N ethane-1,2-diamine;octanedioic acid Chemical compound NCCN.OC(=O)CCCCCCC(O)=O KLEPMTZPTNHHOW-UHFFFAOYSA-N 0.000 description 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 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- DPUXQWOMYBMHRN-UHFFFAOYSA-N hexa-2,3-diene Chemical compound CCC=C=CC DPUXQWOMYBMHRN-UHFFFAOYSA-N 0.000 description 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NRVRMANRRKBYEK-UHFFFAOYSA-N methane;dihydroiodide Chemical compound C.I.I NRVRMANRRKBYEK-UHFFFAOYSA-N 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- UWBHMRBRLOJJAA-UHFFFAOYSA-N oxaluric acid Chemical compound NC(=O)NC(=O)C(O)=O UWBHMRBRLOJJAA-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 235000021395 porridge Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 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
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
- C08G73/0213—Preparatory process
- C08G73/022—Preparatory process from polyamines and epihalohydrins
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polyamides (AREA)
- Paper (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Control Of Fluid Pressure (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30472972A | 1972-11-08 | 1972-11-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2302439A1 true DE2302439A1 (de) | 1974-05-22 |
Family
ID=23177729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2302439A Pending DE2302439A1 (de) | 1972-11-08 | 1973-01-18 | Harze fuer wasserfeste papiere |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3793279A (en, 2012) |
| JP (1) | JPS5133824B2 (en, 2012) |
| AR (1) | AR199282A1 (en, 2012) |
| AT (1) | AT339050B (en, 2012) |
| BE (1) | BE801376A (en, 2012) |
| BR (1) | BR7300858D0 (en, 2012) |
| CA (1) | CA1011012A (en, 2012) |
| CH (2) | CH575973A5 (en, 2012) |
| DD (2) | DD106658A5 (en, 2012) |
| DE (1) | DE2302439A1 (en, 2012) |
| ES (1) | ES411997A1 (en, 2012) |
| FR (1) | FR2205551B1 (en, 2012) |
| GB (1) | GB1417015A (en, 2012) |
| IL (1) | IL41069A (en, 2012) |
| IN (1) | IN138899B (en, 2012) |
| IT (1) | IT974897B (en, 2012) |
| NL (1) | NL154531B (en, 2012) |
| NO (1) | NO131758C (en, 2012) |
| SE (1) | SE401190B (en, 2012) |
| TR (1) | TR17777A (en, 2012) |
| ZA (1) | ZA728820B (en, 2012) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4128398A (en) * | 1974-03-18 | 1978-12-05 | Diamond Shamrock Corporation | Processing aid for use in worsted and woolen processes |
| JPS53104044U (en, 2012) * | 1977-01-26 | 1978-08-22 | ||
| US4708772A (en) * | 1983-04-27 | 1987-11-24 | Hercules Incorporated | Paper products containing wet strength resins |
| US4515657A (en) * | 1983-04-27 | 1985-05-07 | Hercules Incorporated | Wet Strength resins |
| NZ204281A (en) * | 1983-04-27 | 1985-08-30 | Hercules Inc | Preparation of solutions of epihalohydrin-modified polyaminopolyamide resin |
| US4487884A (en) * | 1983-04-27 | 1984-12-11 | Hercules Incorporated | Aqueous solution of cationic thermosetting resin from N-bis(aminopropyl)methylamine/oxalic acid |
| US4605709A (en) * | 1983-04-27 | 1986-08-12 | Hercules Incorporated | Wet strength resin from methylbis(aminopropyl)amine, oxalic acid ester, saturated aliphatic diester and epihalohydrin |
| US4501862A (en) * | 1983-05-23 | 1985-02-26 | Hercules Incorporated | Wet strength resin from aminopolyamide-polyureylene |
| US4689374A (en) * | 1983-06-09 | 1987-08-25 | W. R. Grace & Co. | Water soluble polyamidoaminepolyamine having weight average molecular weight of at least 5×105 |
| GB2141130B (en) * | 1983-06-09 | 1986-11-12 | Grace W R & Co | Polyamidoaminepolyamines |
| US4537657A (en) * | 1983-08-26 | 1985-08-27 | Hercules Incorporated | Wet strength resins |
| GB8613652D0 (en) * | 1986-06-05 | 1986-07-09 | Grace W R Ab | Compositions for sizing paper |
| US4722964A (en) * | 1986-06-20 | 1988-02-02 | Borden, Inc. | Epoxidized polyalkyleneamine-amide wet strength resin |
| JPH0291300A (ja) * | 1988-09-26 | 1990-03-30 | Sanyo Scott Kk | 湿潤強度に優れ且つ水に分散可能な家庭用薄葉紙の製造方法 |
| US5034097A (en) * | 1989-09-25 | 1991-07-23 | Borden, Inc. | Epoxidized polyamide wet strength resins containing lecithin |
| US4970250A (en) * | 1989-09-25 | 1990-11-13 | Borden, Inc. | Epoxidized polyamide wet strength resin containing lecithin |
| US5786429A (en) * | 1996-04-18 | 1998-07-28 | Hercules Incorporated | Highly branched polyamidoamines and their preparation |
| US6398911B1 (en) | 2000-01-21 | 2002-06-04 | Kimberly-Clark Worldwide, Inc. | Modified polysaccharides containing polysiloxane moieties |
| US6896769B2 (en) | 1999-01-25 | 2005-05-24 | Kimberly-Clark Worldwide, Inc. | Modified condensation polymers containing azetidinium groups in conjunction with amphiphilic hydrocarbon moieties |
| US6517678B1 (en) | 2000-01-20 | 2003-02-11 | Kimberly-Clark Worldwide, Inc. | Modified polysaccharides containing amphiphillic hydrocarbon moieties |
| US6596126B1 (en) | 1999-01-25 | 2003-07-22 | Kimberly-Clark Worldwide, Inc. | Modified polysaccharides containing aliphatic hydrocarbon moieties |
| US6465602B2 (en) | 2000-01-20 | 2002-10-15 | Kimberly-Clark Worldwide, Inc. | Modified condensation polymers having azetidinium groups and containing polysiloxane moieties |
| US7306698B2 (en) * | 2001-03-20 | 2007-12-11 | Biopulping International | Method for producing pulp |
| US7758934B2 (en) * | 2007-07-13 | 2010-07-20 | Georgia-Pacific Consumer Products Lp | Dual mode ink jet paper |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1543136A (fr) * | 1966-11-03 | 1968-10-18 | Basf Ag | Nouveaux polycondensats solubles à l'eau et réticulables, et procédé pour leur préparation |
-
1972
- 1972-11-08 US US00304729A patent/US3793279A/en not_active Expired - Lifetime
- 1972-12-12 IL IL41069A patent/IL41069A/en unknown
- 1972-12-13 GB GB5750172A patent/GB1417015A/en not_active Expired
- 1972-12-13 ZA ZA728820A patent/ZA728820B/xx unknown
- 1972-12-29 JP JP734539A patent/JPS5133824B2/ja not_active Expired
- 1972-12-29 IT IT55234/72A patent/IT974897B/it active
- 1972-12-31 AR AR245612A patent/AR199282A1/es active
-
1973
- 1973-01-05 SE SE7300153A patent/SE401190B/xx unknown
- 1973-01-09 CA CA160,874A patent/CA1011012A/en not_active Expired
- 1973-01-15 AT AT28973A patent/AT339050B/de not_active IP Right Cessation
- 1973-01-15 IN IN117/CAL/73A patent/IN138899B/en unknown
- 1973-01-18 NO NO211/73A patent/NO131758C/no unknown
- 1973-01-18 DE DE2302439A patent/DE2302439A1/de active Pending
- 1973-01-19 NL NL737300823A patent/NL154531B/xx unknown
- 1973-02-05 BR BR73858A patent/BR7300858D0/pt unknown
- 1973-02-05 DD DD168702A patent/DD106658A5/xx unknown
- 1973-02-05 DD DD176594*A patent/DD114843A5/xx unknown
- 1973-02-23 ES ES411997A patent/ES411997A1/es not_active Expired
- 1973-04-10 FR FR7312807A patent/FR2205551B1/fr not_active Expired
- 1973-04-16 CH CH546173A patent/CH575973A5/xx not_active IP Right Cessation
- 1973-04-16 CH CH353976A patent/CH583820A5/xx not_active IP Right Cessation
- 1973-06-25 BE BE132662A patent/BE801376A/xx unknown
- 1973-10-16 TR TR17777A patent/TR17777A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO131758B (en, 2012) | 1975-04-14 |
| IL41069A (en) | 1976-01-30 |
| AU5014072A (en) | 1974-06-13 |
| FR2205551B1 (en, 2012) | 1976-09-10 |
| CH583820A5 (en, 2012) | 1977-01-14 |
| FR2205551A1 (en, 2012) | 1974-05-31 |
| AR199282A1 (es) | 1974-08-23 |
| NL154531B (nl) | 1977-09-15 |
| GB1417015A (en) | 1975-12-10 |
| DD114843A5 (en, 2012) | 1975-08-20 |
| ATA28973A (de) | 1977-01-15 |
| SE401190B (sv) | 1978-04-24 |
| JPS4981454A (en, 2012) | 1974-08-06 |
| US3793279A (en) | 1974-02-19 |
| DD106658A5 (en, 2012) | 1974-06-20 |
| NO131758C (en, 2012) | 1975-07-23 |
| BR7300858D0 (pt) | 1974-09-05 |
| IL41069A0 (en) | 1973-02-28 |
| IT974897B (it) | 1974-07-10 |
| IN138899B (en, 2012) | 1976-04-10 |
| AT339050B (de) | 1977-09-26 |
| ZA728820B (en) | 1974-02-27 |
| JPS5133824B2 (en, 2012) | 1976-09-22 |
| TR17777A (tr) | 1976-09-01 |
| CH575973A5 (en, 2012) | 1976-05-31 |
| NL7300823A (en, 2012) | 1974-05-10 |
| CA1011012A (en) | 1977-05-24 |
| BE801376A (fr) | 1973-12-26 |
| ES411997A1 (es) | 1976-06-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2302439A1 (de) | Harze fuer wasserfeste papiere | |
| DE1645536C3 (de) | Verfahren zur Herstellung von wasserlöslichen, hitzehärtbaren Polymeren | |
| EP0002474B1 (de) | Amidgruppenhaltige Polyamine und ihre Verwendung bei der Papierherstellung | |
| DE69929307T3 (de) | Kreppklebemittel und verfahren zum kreppen von papier | |
| DE2938588C3 (de) | Verfahren zur Herstellung einer wäßrigen Lösung eines wärmehärtbaren Harzes und deren Verwendung | |
| DE3032288C2 (en, 2012) | ||
| DE1177824B (de) | Verfahren zur Herstellung von wasserloeslichen Kondensaten auf Basis von Polyamiden und Epichlorhydrin | |
| DE69400997T2 (de) | Zusammensetzung für die Herstellung von nassverfestigtem Papier | |
| DE60201933T2 (de) | Harze verwendbar als Nassfestigkeitsmittel und Krepphilfsmittel, ihre Herstellung und ihre Verwendung | |
| DE3708854C2 (de) | Masseleimungsmittel für die Papierherstellung | |
| DE2928878C2 (de) | Wäßrige Lösung eines wärmehärt- oder -fixierbaren Harzes, Verfahren zu ihrer Herstellung und ihre Verwendung in einer Papierstreichmasse | |
| DE19728789A1 (de) | Naßfestmittel mit niedrigem DCP-Gehalt | |
| DE19517047C2 (de) | Verfahren zur Herstellung vernetzter Kationpolymere und ihre Verwendung zur Papierbehandlung | |
| US3992251A (en) | Process of making wet strength paper containing mono primary polyamine and organic dihalide modified, epoxidized polyamide | |
| DE2604036A1 (de) | Pfropfcopolymeres, verfahren zu seiner herstellung und seine verwendung | |
| EP0540943B1 (de) | Verfahren zur Herstellung von Polykondensaten | |
| DE2353430C2 (de) | Verfahren zur Herstellung von kationischen Polyaminopolyamiden und deren Verwendung als Papiererzeugungshilfsmittel | |
| DE69926509T2 (de) | Tertiäre amine polyamidoamin - epihalohydrin- polymere | |
| EP0002475B1 (de) | Amidgruppenhaltige Polyamine, ihre Herstellung, ihre Verwendung bei der Papierherstellung und Hilfsmittel, die diese Polyamine enthalten | |
| EP0158247B1 (de) | Papierhilfsmittel | |
| DE2949870A1 (de) | Kondensationsprodukte zur erhoehung der nassfestigkeit von papier | |
| DE1495195A1 (de) | Kondensationsprodukte | |
| DE1771243C3 (de) | Verfahren zum Leimen von Papiererzeugnissen in der Masse und durch Oberflächenbehandlung | |
| DE2026449C3 (de) | Verfahren zur Herstellung von wasserlöslichen stickstoffhaltigen Polykondensaten | |
| EP0201761B1 (de) | Verwendung von basischen Amiden zur Erhöhung der Parasität von Papier oder papierähnlichen Materialien |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |