DE2017509A1 - Basisch anfärbbare hochmolekulare aromatische Polyamide - Google Patents
Basisch anfärbbare hochmolekulare aromatische PolyamideInfo
- Publication number
- DE2017509A1 DE2017509A1 DE19702017509 DE2017509A DE2017509A1 DE 2017509 A1 DE2017509 A1 DE 2017509A1 DE 19702017509 DE19702017509 DE 19702017509 DE 2017509 A DE2017509 A DE 2017509A DE 2017509 A1 DE2017509 A1 DE 2017509A1
- Authority
- DE
- Germany
- Prior art keywords
- aromatic
- disulfimide
- polyamides
- aromatic polyamides
- group
- 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
- 239000004760 aramid Substances 0.000 title claims description 19
- 229920003235 aromatic polyamide Polymers 0.000 title claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 239000004952 Polyamide Substances 0.000 claims description 24
- 229920002647 polyamide Polymers 0.000 claims description 24
- -1 aromatic carboxylic acid halides Chemical class 0.000 claims description 19
- 150000004985 diamines Chemical class 0.000 claims description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000006068 polycondensation reaction Methods 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000981 basic dye Substances 0.000 claims description 4
- 229910052736 halogen Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 2
- 150000002367 halogens Chemical group 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 150000004984 aromatic diamines Chemical class 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 239000011888 foil Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 44
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
- 229940113088 dimethylacetamide Drugs 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 238000009987 spinning Methods 0.000 description 5
- 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 4
- 239000002253 acid Substances 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000003495 polar organic solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000008033 biological extinction Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VRAKUODIXKIKJN-UHFFFAOYSA-N 1,3-bis(4-aminophenyl)-5,5-dimethylimidazolidine-2,4-dione Chemical compound O=C1C(C)(C)N(C=2C=CC(N)=CC=2)C(=O)N1C1=CC=C(N)C=C1 VRAKUODIXKIKJN-UHFFFAOYSA-N 0.000 description 2
- SDQJTWBNWQABLE-UHFFFAOYSA-N 1h-quinazoline-2,4-dione Chemical compound C1=CC=C2C(=O)NC(=O)NC2=C1 SDQJTWBNWQABLE-UHFFFAOYSA-N 0.000 description 2
- TXTQURPQLVHJRE-UHFFFAOYSA-N 3-nitrobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 TXTQURPQLVHJRE-UHFFFAOYSA-N 0.000 description 2
- ATOCBZNTKIBZIH-UHFFFAOYSA-N 7-amino-3-(4-aminophenyl)-1h-quinazoline-2,4-dione Chemical compound C1=CC(N)=CC=C1N1C(=O)C2=CC=C(N)C=C2NC1=O ATOCBZNTKIBZIH-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 2
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 2
- 125000002228 disulfide group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010409 ironing Methods 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- MGCGMYPNXAFGFA-UHFFFAOYSA-N 2-amino-5-nitrobenzonitrile Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C#N MGCGMYPNXAFGFA-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- 238000012696 Interfacial polycondensation Methods 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229920006017 homo-polyamide Polymers 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000002166 wet spinning Methods 0.000 description 1
Classifications
-
- 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
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/32—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from aromatic diamines and aromatic dicarboxylic acids with both amino and carboxylic groups aromatically bound
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/924—Polyamide fiber
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
- Artificial Filaments (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702017509 DE2017509A1 (de) | 1970-04-13 | 1970-04-13 | Basisch anfärbbare hochmolekulare aromatische Polyamide |
| NL7104697A NL7104697A (enExample) | 1970-04-13 | 1971-04-07 | |
| US132170A US3676525A (en) | 1970-04-13 | 1971-04-07 | High molecular weight aromatic polyamides having an affinity for basic dyes |
| CA109955A CA928891A (en) | 1970-04-13 | 1971-04-08 | High molecular weight aromatic polyamides having an affinity for basic dyes |
| FR7112998A FR2086037B1 (enExample) | 1970-04-13 | 1971-04-13 | |
| BE765649A BE765649A (fr) | 1970-04-13 | 1971-04-13 | Polyamides aromatiques a poids moleculaire eleve ayant de l'affinite pour les colorants basiques |
| GB2466571*A GB1353348A (en) | 1970-04-13 | 1971-04-19 | High molecular weight aromatic polyamides having an affinity for basic dyes |
| US00219819A US3786024A (en) | 1970-04-13 | 1972-01-21 | High molecular weight aromatic polyamides having an affinity for basic dyes |
| US40739474 USRE28314E (en) | 1970-04-13 | 1974-01-15 | Search room |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702017509 DE2017509A1 (de) | 1970-04-13 | 1970-04-13 | Basisch anfärbbare hochmolekulare aromatische Polyamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2017509A1 true DE2017509A1 (de) | 1971-11-04 |
Family
ID=5767882
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702017509 Pending DE2017509A1 (de) | 1970-04-13 | 1970-04-13 | Basisch anfärbbare hochmolekulare aromatische Polyamide |
Country Status (7)
| Country | Link |
|---|---|
| US (3) | US3676525A (enExample) |
| BE (1) | BE765649A (enExample) |
| CA (1) | CA928891A (enExample) |
| DE (1) | DE2017509A1 (enExample) |
| FR (1) | FR2086037B1 (enExample) |
| GB (1) | GB1353348A (enExample) |
| NL (1) | NL7104697A (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2017509A1 (de) * | 1970-04-13 | 1971-11-04 | Bayer Ag | Basisch anfärbbare hochmolekulare aromatische Polyamide |
| FR2198973B1 (enExample) * | 1972-09-13 | 1975-03-14 | Rhone Poulenc Ind | |
| ES462585A1 (es) * | 1976-09-24 | 1978-07-16 | Bauer Ag | Procedimiento para la obtencion de membranas semipermeables. |
| US4412547A (en) | 1981-04-29 | 1983-11-01 | Neurologics, Inc. | Neurological monitoring device |
| ES2183551T3 (es) * | 1998-06-29 | 2003-03-16 | California Inst Of Techn | Tamiz molecular cit-6. |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3063966A (en) * | 1958-02-05 | 1962-11-13 | Du Pont | Process of making wholly aromatic polyamides |
| US2989495A (en) * | 1958-08-13 | 1961-06-20 | Du Pont | Solution of wholly aromatic polyamides in liquid organic amine solvents |
| US3094511A (en) * | 1958-11-17 | 1963-06-18 | Du Pont | Wholly aromatic polyamides |
| DE1250964B (de) * | 1964-06-25 | 1967-09-28 | Farbenfabriken Bayer Aktiengesell schaft Leverkusen | Verfahren zum Herstellen von strukturgekrauselten Faden und Fasern aus Polyamiden |
| GB1143574A (enExample) * | 1965-02-02 | |||
| US3403200A (en) * | 1966-03-30 | 1968-09-24 | Borg Warner | Polyamide and polysulfonamide azo dyes |
| US3514498A (en) * | 1966-11-01 | 1970-05-26 | Toray Industries | Antistatic synthetic resin composition containing a polyether - polyamide block copolymer wherein an ionic functional group is made to coexist |
| DE1720662A1 (de) * | 1967-06-01 | 1971-07-01 | Bayer Ag | Verfahren zur Herstellung basisch anfaerbbarer Polyamide |
| FR2002512A1 (en) * | 1967-08-29 | 1969-10-17 | Bayer Ag | Copolyamides contg a high proportion of acid sulphonate |
| US3519699A (en) * | 1968-01-25 | 1970-07-07 | Allied Chem | Polyamide blends containing dicarboxy diphenyl sulfone groups and pipenidyl groups |
| DE2017509A1 (de) * | 1970-04-13 | 1971-11-04 | Bayer Ag | Basisch anfärbbare hochmolekulare aromatische Polyamide |
-
1970
- 1970-04-13 DE DE19702017509 patent/DE2017509A1/de active Pending
-
1971
- 1971-04-07 NL NL7104697A patent/NL7104697A/xx not_active Application Discontinuation
- 1971-04-07 US US132170A patent/US3676525A/en not_active Expired - Lifetime
- 1971-04-08 CA CA109955A patent/CA928891A/en not_active Expired
- 1971-04-13 BE BE765649A patent/BE765649A/xx unknown
- 1971-04-13 FR FR7112998A patent/FR2086037B1/fr not_active Expired
- 1971-04-19 GB GB2466571*A patent/GB1353348A/en not_active Expired
-
1972
- 1972-01-21 US US00219819A patent/US3786024A/en not_active Expired - Lifetime
-
1974
- 1974-01-15 US US40739474 patent/USRE28314E/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE765649A (fr) | 1971-08-30 |
| US3676525A (en) | 1972-07-11 |
| US3786024A (en) | 1974-01-15 |
| FR2086037A1 (enExample) | 1971-12-31 |
| GB1353348A (en) | 1974-05-15 |
| NL7104697A (enExample) | 1971-10-15 |
| CA928891A (en) | 1973-06-19 |
| USRE28314E (en) | 1975-01-21 |
| FR2086037B1 (enExample) | 1976-02-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |