EP0000331A1 - Procédé de teinture de polyamides linéaires dans la masse au moyen de sels de colorants monoazoique chromifères 1:2; les fibres ainsi obtenues - Google Patents

Procédé de teinture de polyamides linéaires dans la masse au moyen de sels de colorants monoazoique chromifères 1:2; les fibres ainsi obtenues Download PDF

Info

Publication number: EP0000331A1
Authority: EP; European Patent Office
Prior art keywords: group; carbon atoms; atoms; groups; alkyl
Prior art date: 1977-06-23
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.): Granted

Application number

EP78100161A

Other languages

German (de)

English (en)

Other versions

EP0000331B1 (fr

Inventor

Paul Dr. Lienhard

Abul Dr. Iqbal

Heinz Dr. Peter

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

Novartis AG

Original Assignee

Ciba Geigy AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-06-23

Filing date

1978-06-15

Publication date

1979-01-24

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=4329489&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0000331(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1978-06-15 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1979-01-24 Publication of EP0000331A1 publication Critical patent/EP0000331A1/fr

1983-12-28 Application granted granted Critical

1983-12-28 Publication of EP0000331B1 publication Critical patent/EP0000331B1/fr

Status Expired legal-status Critical Current

Links

239000004952 Polyamide Substances 0.000 title claims abstract description 18
229920002647 polyamide Polymers 0.000 title claims abstract description 18
238000000034 method Methods 0.000 title claims abstract description 14
150000001844 chromium Chemical class 0.000 title claims abstract description 7
238000004043 dyeing Methods 0.000 title claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 61
239000000975 dye Substances 0.000 claims abstract description 39
150000003839 salts Chemical class 0.000 claims abstract description 28
239000011651 chromium Substances 0.000 claims abstract description 21
239000000987 azo dye Substances 0.000 claims abstract description 14
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 5
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 5
150000001412 amines Chemical class 0.000 claims abstract description 4
NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims abstract description 4
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims abstract 3
125000000217 alkyl group Chemical group 0.000 claims description 26
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
125000005843 halogen group Chemical group 0.000 claims description 17
-1 amine salts Chemical class 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
125000005236 alkanoylamino group Chemical group 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
125000002947 alkylene group Chemical group 0.000 claims description 4
150000001768 cations Chemical class 0.000 claims description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
238000003776 cleavage reaction Methods 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
239000000835 fiber Substances 0.000 claims description 3
230000007017 scission Effects 0.000 claims description 3
125000000542 sulfonic acid group Chemical group 0.000 claims description 3
125000005263 alkylenediamine group Chemical group 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
125000002993 cycloalkylene group Chemical group 0.000 claims description 2
150000004985 diamines Chemical class 0.000 claims description 2
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
239000001257 hydrogen Substances 0.000 claims 3
125000003277 amino group Chemical group 0.000 claims 1
125000004427 diamine group Chemical group 0.000 claims 1
125000004430 oxygen atom Chemical group O* 0.000 claims 1
238000004040 coloring Methods 0.000 abstract description 2
230000008030 elimination Effects 0.000 abstract 1
238000003379 elimination reaction Methods 0.000 abstract 1
235000002639 sodium chloride Nutrition 0.000 description 33
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
NAQMVNRVTILPCV-UHFFFAOYSA-N hexamethylene diamine Natural products NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 21
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 15
235000019253 formic acid Nutrition 0.000 description 15
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
229920002292 Nylon 6 Polymers 0.000 description 10
229910052804 chromium Inorganic materials 0.000 description 10
159000000000 sodium salts Chemical class 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 8
238000009998 heat setting Methods 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000011780 sodium chloride Substances 0.000 description 8
238000009987 spinning Methods 0.000 description 8
TYFGMFQLFGWYBY-UHFFFAOYSA-N 2-amino-5-ethylsulfonylphenol Chemical compound CCS(=O)(=O)C1=CC=C(N)C(O)=C1 TYFGMFQLFGWYBY-UHFFFAOYSA-N 0.000 description 6
YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
239000002657 fibrous material Substances 0.000 description 5
239000000203 mixture Substances 0.000 description 5
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000012065 filter cake Substances 0.000 description 3
230000001376 precipitating effect Effects 0.000 description 3
MRERMGPPCLQIPD-NBVRZTHBSA-N (3beta,5alpha,9alpha,22E,24R)-3,5,9-Trihydroxy-23-methylergosta-7,22-dien-6-one Chemical compound C1C(O)CCC2(C)C(CCC3(C(C(C)/C=C(\C)C(C)C(C)C)CCC33)C)(O)C3=CC(=O)C21O MRERMGPPCLQIPD-NBVRZTHBSA-N 0.000 description 2
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
NFNLMGYLSDEJKS-UHFFFAOYSA-N 3-amino-4-hydroxy-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(O)C(N)=C1 NFNLMGYLSDEJKS-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
0 C*(CC(C)(C1)NC)/C=C/C=C1/[n]1nc(*)c(C)c1O Chemical compound C*(CC(C)(C1)NC)/C=C/C=C1/[n]1nc(*)c(C)c1O 0.000 description 2
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
235000011037 adipic acid Nutrition 0.000 description 2
239000001361 adipic acid Substances 0.000 description 2
150000001447 alkali salts Chemical class 0.000 description 2
229940116224 behenate Drugs 0.000 description 2
UKMSUNONTOPOIO-UHFFFAOYSA-M behenate Chemical compound CCCCCCCCCCCCCCCCCCCCCC([O-])=O UKMSUNONTOPOIO-UHFFFAOYSA-M 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
239000002245 particle Substances 0.000 description 2
DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
RCTGMCJBQGBLKT-PAMTUDGESA-N scarlet red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 description 2
229960005369 scarlet red Drugs 0.000 description 2
239000007787 solid Substances 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
238000009736 wetting Methods 0.000 description 2
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
YAZGIBSHMAGPQR-UHFFFAOYSA-N 2,11-dimethyldodecane-2,11-diamine Chemical compound CC(C)(N)CCCCCCCCC(C)(C)N YAZGIBSHMAGPQR-UHFFFAOYSA-N 0.000 description 1
FZUWIRGHKCUMTH-UHFFFAOYSA-N 2,13-dimethyltetradecane-3,12-diamine Chemical compound CC(C)C(N)CCCCCCCCC(N)C(C)C FZUWIRGHKCUMTH-UHFFFAOYSA-N 0.000 description 1
DAGLNKUWJGMCHW-UHFFFAOYSA-N 2,15-dimethylhexadecane-4,13-diamine Chemical compound CC(C)CC(N)CCCCCCCCC(N)CC(C)C DAGLNKUWJGMCHW-UHFFFAOYSA-N 0.000 description 1
KWVPRPSXBZNOHS-UHFFFAOYSA-N 2,4,6-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C(C)=C1 KWVPRPSXBZNOHS-UHFFFAOYSA-N 0.000 description 1
SWFNPENEBHAHEB-UHFFFAOYSA-N 2-amino-4-chlorophenol Chemical compound NC1=CC(Cl)=CC=C1O SWFNPENEBHAHEB-UHFFFAOYSA-N 0.000 description 1
BZUDVELGTZDOIG-UHFFFAOYSA-N 2-ethyl-n,n-bis(2-ethylhexyl)hexan-1-amine Chemical compound CCCCC(CC)CN(CC(CC)CCCC)CC(CC)CCCC BZUDVELGTZDOIG-UHFFFAOYSA-N 0.000 description 1
MAPYCRDUDFPCEB-UHFFFAOYSA-N 2-propan-2-yloxypropan-1-amine Chemical compound CC(C)OC(C)CN MAPYCRDUDFPCEB-UHFFFAOYSA-N 0.000 description 1
CPYIHCJGWGMBAV-UHFFFAOYSA-N 3,14-dimethylhexadecane-4,13-diamine Chemical compound CCC(C)C(N)CCCCCCCCC(N)C(C)CC CPYIHCJGWGMBAV-UHFFFAOYSA-N 0.000 description 1
PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
RXCMFQDTWCCLBL-UHFFFAOYSA-N 4-amino-3-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 RXCMFQDTWCCLBL-UHFFFAOYSA-N 0.000 description 1
235000021357 Behenic acid Nutrition 0.000 description 1
MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical group NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
229920002302 Nylon 6,6 Polymers 0.000 description 1
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
239000004959 Rilsan Substances 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
229940116226 behenic acid Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 1
CBLAIDIBZHTGLV-UHFFFAOYSA-N dodecane-2,11-diamine Chemical compound CC(N)CCCCCCCCC(C)N CBLAIDIBZHTGLV-UHFFFAOYSA-N 0.000 description 1
JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
238000005108 dry cleaning Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
MIHXSBPXSQUTAE-UHFFFAOYSA-N hexadecane-4,13-diamine Chemical compound CCCC(N)CCCCCCCCC(N)CCC MIHXSBPXSQUTAE-UHFFFAOYSA-N 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
238000010309 melting process Methods 0.000 description 1
PWNDYKKNXVKQJO-UHFFFAOYSA-N n',n'-dibutylethane-1,2-diamine Chemical compound CCCCN(CCN)CCCC PWNDYKKNXVKQJO-UHFFFAOYSA-N 0.000 description 1
ODGYWRBCQWKSSH-UHFFFAOYSA-N n'-ethylpropane-1,3-diamine Chemical compound CCNCCCN ODGYWRBCQWKSSH-UHFFFAOYSA-N 0.000 description 1
ALNWQAFPXMGLTJ-UHFFFAOYSA-N n-(7-hydroxynaphthalen-1-yl)acetamide Chemical compound C1=C(O)C=C2C(NC(=O)C)=CC=CC2=C1 ALNWQAFPXMGLTJ-UHFFFAOYSA-N 0.000 description 1
QHCCDDQKNUYGNC-UHFFFAOYSA-N n-ethylbutan-1-amine Chemical compound CCCCNCC QHCCDDQKNUYGNC-UHFFFAOYSA-N 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
KVHGRNNYXUQOHE-UHFFFAOYSA-N octadecane-5,14-diamine Chemical compound CCCCC(N)CCCCCCCCC(N)CCCC KVHGRNNYXUQOHE-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229940100684 pentylamine Drugs 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
238000012667 polymer degradation Methods 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000012216 screening Methods 0.000 description 1
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
201000009032 substance abuse Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
WVYODUPGRLXIBB-UHFFFAOYSA-N tetradecane-3,12-diamine Chemical compound CCC(N)CCCCCCCCC(N)CC WVYODUPGRLXIBB-UHFFFAOYSA-N 0.000 description 1
239000004753 textile Substances 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
- C09B69/04—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds
- C09B69/045—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds of anionic azo dyes
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0091—Complexes with metal-heteroatom-bonds
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/48—Preparation from other complex metal compounds of azo dyes
- C09B45/482—Chromium complexes

Definitions

alkali salts of the 1: 2 metal complexes of monoazo dyes can be used for the mass coloring of synthetic polyamides (see e.g. GB-PS 1 021 737 and 1 264 191 and FR-PS 1 547 128).
the colored bodies isolated as alkali salts often stubbornly hold back water or absorb water again after storage after sharp drying, which can lead to polymer degradation or corrosion in the spinning system during the spinning process.
the dyes to be used are advantageously of sulfonic acid groups and free, i.e. not bound complex carboxyl groups free.
Examples of monoamines are methylamine, trimethylamine, ethylamine, diethylamine, triethylamine, propylamine, isopropylamine, 2-isopropoxy-n-propylamine, n-butylamine, isobutylamine, ethyl-n-butylamine, tri- (n-butyl) amine, pentylamine , n-hexylamine, tri- (2-ethylhexyl) amine, cyclohexylamine, N-methylcyclohexylamine, dicyclohexylamine, benzylamine, aniline, m-chloroaniline, mesitylamine, o-anisidine, N-ethylaniline, p-toluidine, octylamine, n-decylamine , ⁇ -aminoundecanoic acid, n-dodecylamine or stearyl
diamines such as N, N-dibutylethylenediamine, N- ⁇ -hydroxyethyl-ethylenediamine, p-phenylenediamine and N-ethylpropylenediamine, but in particular symmetrically constructed alkylenediamines having 2 to 18 carbon atoms, for example ethylene, propylene, tetramethylene, pentamethylene, Hexamethylene diamine, 1,12-diaminododecane, 2,11-diaminododecane, 3,12-diaminotetradecane, 2,11-diamino-2,11-dimethyldodecane, 4,13-diamino-3,14-dimethyl-hexadecane, 4,13-diamino-hexadecane, 3,12-diamino-2,13-dimethyl-tetradecane, 5,14-diamino-octadecane, 4,13-d
An example of a triamine is diethylene triamine and an example of a heterocyclic amine is piperazine.
Suitable linear polyamides for the present process are the polyamides, such as those obtained from -C -caprolactam ("Perlon", nylon 6), from ⁇ -aminoundecanoic acid (“Rilsan”), from hexamethylenediamine and adipic acid (“nylon” 6,6 ) or can be produced from analogous starting materials.
Mixed polyamides for example composed of E-caprolactam and hexamethylene diamine and adipic acid, are also suitable.
the dyes are mixed in solid or liquid form or as a solution with the polyamide by known processes and the mixture obtained is optionally dried.
the polyamides to be colored are preferably breaded with the dry dye powder in the form of powders, granules or chips, i.e. mechanically mixed in such a way that the surface of these particles is coated with a layer of the dye.
the dye is advantageously in finely divided form.
preparations which, in addition to the dye, contain a carrier, preferably a Ca or Mg salt of a higher fatty acid, for example stearic or behenic acid.
the polyamide particles containing the dye or the dye preparation are melted and spun by known methods or otherwise, for example to give films or other molded parts, for example injection molded articles.
the dye or dye preparation can also be introduced into the molten polyamide in solid or liquid form and then spun or deformed.
Uniformly colored objects are obtained which are distinguished by a high light, wet, rubbing and heat setting fastness.
the dyes are evenly and finely distributed in the colored material. Although their solubilities in organic solvents such as chlorinated hydrocarbons, lower ketones, esters and alcohols are not high, they are often in dissolved form in polyamide.
the colored objects expediently contain 0.01 to 3% of dye.
the filter cake is washed successively with 600 ml of a 1% formic acid solution and 600 ml of water.
the product dried in vacuo (110-115 ° C) weighs 87.8 g. It has a color salt content of 97.1%, contains only 0.25% NaCl and 1% water.
a 90 ° C warm solution of 1.18 g (0.01 mol) of hexamethylenediamine in 50 ml of H 2 0 and 1.1 g (0.024 mol) of formic acid is added to a 90 ° C suspension of 16.87 g (0.02 mol) of l : 2-Chromium complex sodium salt from the azo dye 2-amino-5-ethylsulfonyl-phenol ⁇ 1-phenyl-3-methyl-5-pyrazolone added dropwise in 200 ml of water.
the dropping funnel is rinsed out with about 20 ml of water and the reaction mixture is left to react at 90-95 ° C. for a further hour with stirring.
the precipitated dye is filtered off, washed successively with 150 ml of a 1% formic acid solution and 150 ml of water and finally dried at 110-115 ° C. 17.2 g of color salt are obtained. It contains only 0.057% NaCl and 1.4% H 2 0.
the separated product is filtered off, washed with 300 ml of water and dried in a vacuum oven at 110-115 ° C.
the butanolic filtrate is shaken twice with 100 ml of water and then connected send completely evaporated in a rotating flask. In this way, a further smaller amount of product is obtained, which is also dried under vacuum at 110-115 ° C.
the total yield of color salt is 20.9 g. It contains ⁇ 0.1% table salt.
Example 1 60 g of the dye obtained in Example 1 and 60 g of Mg behenate are worked in a kneader at 120-130 ° C. for 1/4 hour. After reaching a homogeneous mixture, the cooled, brittle product is ground. A dye preparation containing 50% color salt is obtained.

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Coloring (AREA)
Compositions Of Macromolecular Compounds (AREA)
Artificial Filaments (AREA)

EP78100161A 1977-06-23 1978-06-15 Procédé de teinture de polyamides linéaires dans la masse au moyen de sels de colorants monoazoique chromifères 1:2; les fibres ainsi obtenues Expired EP0000331B1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH7722/77		1977-06-23
CH772277		1977-06-23

Publications (2)

Publication Number	Publication Date
EP0000331A1 true EP0000331A1 (fr)	1979-01-24
EP0000331B1 EP0000331B1 (fr)	1983-12-28

Family

ID=4329489

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP78100161A Expired EP0000331B1 (fr)	1977-06-23	1978-06-15	Procédé de teinture de polyamides linéaires dans la masse au moyen de sels de colorants monoazoique chromifères 1:2; les fibres ainsi obtenues

Country Status (8)

Country	Link
US (1)	US4263197A (fr)
EP (1)	EP0000331B1 (fr)
JP (1)	JPS5413557A (fr)
CA (1)	CA1103385A (fr)
CS (1)	CS194848B2 (fr)
DE (1)	DE2862357D1 (fr)
PL (1)	PL106520B1 (fr)
SU (1)	SU735173A3 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2633631A1 (fr) *	1988-06-30	1990-01-05	Sandoz Sa	Sels de colorants pour la teinture dans la masse des polyamides synthetiques
US5965716A (en) *	1989-10-03	1999-10-12	Clariant Finance (Bvi) Limited	Dyestuff salts containing a cationic group derived from a sterically hindered amine

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3017070A1 (de) *	1980-05-03	1981-11-05	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung salzarmer wasserloeslicher farbstoffe
US5942438A (en)	1997-11-07	1999-08-24	Johnson & Johnson Medical, Inc.	Chemical indicator for oxidation-type sterilization processes using bleachable dyes
WO2001058997A1 (fr) *	2000-02-11	2001-08-16	E.I. Dupont De Nemours And Company	Compositions de resines thermoplastiques destinees au soudage par laser et articles formes a partir de ces compositions
US7686993B2 (en) *	2003-03-18	2010-03-30	Ciba Specialty Chemicals Corporation	Colored polymeric articles having high melt temperatures
US7294730B2 (en) *	2005-11-30	2007-11-13	Xerox Corporation	Colorant compounds
JP2015063631A (ja) *	2013-09-26	2015-04-09	日本化薬株式会社	アゾ化合物
JP7408915B2 (ja) *	2019-01-31	2024-01-09	セイコーエプソン株式会社	インクジェット捺染インク組成物及び記録方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2814614A (en) *	1953-04-02	1957-11-26	Ciba Ltd	New conversion products of azo dyestuffs containing metal compounds in complex union
DE1110786B (de) *	1958-06-12	1961-07-13	Geigy Ag J R	Verfahren zur Herstellung von acetonloeslichen Umwandlungsprodukten metallisierter Azofarbstoffe
GB1021737A (en) *	1963-05-08	1966-03-09	Ici Ltd	Process for the coloration of polyamides
DE1226727B (de) *	1960-08-09	1966-10-13	Basf Ag	Verfahren zur Herstellung von Ammoniumsalzen sulfonsaeuregruppenhaltiger Metallkomplexfarbstoffe
FR2032291A7 (fr) *	1968-12-12	1970-11-27	Siemens Ag
GB1264191A (fr) *	1968-02-02	1972-02-16
CH524011A (de) *	1966-12-29	1972-06-15	Basf Ag	Verfahren zum Färben von Granulaten oder Pulvern aus synthetischen Polyamiden

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee
NL129233C (fr) *	1965-01-15
CH280069A4 (fr) *	1969-02-25	1972-01-31
FR2212398B1 (fr) *	1972-12-28	1976-06-04	Ugine Kuhlmann
FR2219964B1 (fr) *	1973-03-02	1978-03-03	Ugine Kuhlmann
CH616953A5 (fr) *	1975-08-27	1980-04-30	Sandoz Ag

1978
- 1978-06-15 DE DE7878100161T patent/DE2862357D1/de not_active Expired
- 1978-06-15 EP EP78100161A patent/EP0000331B1/fr not_active Expired
- 1978-06-20 CS CS784060A patent/CS194848B2/cs unknown
- 1978-06-21 CA CA305,943A patent/CA1103385A/fr not_active Expired
- 1978-06-23 PL PL1978207862A patent/PL106520B1/pl unknown
- 1978-06-23 SU SU782628098A patent/SU735173A3/ru active
- 1978-06-23 JP JP7635778A patent/JPS5413557A/ja active Granted
1979
- 1979-09-27 US US06/079,292 patent/US4263197A/en not_active Expired - Lifetime

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2814614A (en) *	1953-04-02	1957-11-26	Ciba Ltd	New conversion products of azo dyestuffs containing metal compounds in complex union
DE1110786B (de) *	1958-06-12	1961-07-13	Geigy Ag J R	Verfahren zur Herstellung von acetonloeslichen Umwandlungsprodukten metallisierter Azofarbstoffe
DE1226727B (de) *	1960-08-09	1966-10-13	Basf Ag	Verfahren zur Herstellung von Ammoniumsalzen sulfonsaeuregruppenhaltiger Metallkomplexfarbstoffe
DE1260652B (de) *	1960-08-09	1968-02-08	Basf Ag	Verfahren zur Herstellung von Ammoniumsalzen von Metallkomplexfarbstoffen
GB1021737A (en) *	1963-05-08	1966-03-09	Ici Ltd	Process for the coloration of polyamides
CH524011A (de) *	1966-12-29	1972-06-15	Basf Ag	Verfahren zum Färben von Granulaten oder Pulvern aus synthetischen Polyamiden
GB1264191A (fr) *	1968-02-02	1972-02-16
FR2032291A7 (fr) *	1968-12-12	1970-11-27	Siemens Ag

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Vol. 83, Nr. 10, September 8, 1975, Seiten 117-118, Colum bus, Ohio USA, "Abstract" 81192c & JP-A-50 010 323 (HODOGAYA CHEMICAL). *
CHEMICAL ABSTRACTS, Vol. 83, Nr. 24, Dezember 15, 1975, Seite 80 Columbus, Ohio USA, "Abstract" 194775p & JP-A-49 086 501 (HODOGAYA CHEMICAL). *
CHEMICAL ABSTRACTS, Vol. 83, Nr. 8, August 25, 1975, Seite 213, Columbus, Ohi o, USA, "Abstract" 62021e & JP-A-49 101 506 (HODOGAYA CHEMICAL) *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2633631A1 (fr) *	1988-06-30	1990-01-05	Sandoz Sa	Sels de colorants pour la teinture dans la masse des polyamides synthetiques
BE1004045A3 (fr) *	1988-06-30	1992-09-15	Sandoz Sa	Sels de colorants pour la teinture dans la masse des polyamides synthetiques.
US5316553A (en) *	1988-06-30	1994-05-31	Sandoz Ltd.	Dyestuffs for the dyeing of synthetic polyamides
US5965716A (en) *	1989-10-03	1999-10-12	Clariant Finance (Bvi) Limited	Dyestuff salts containing a cationic group derived from a sterically hindered amine

Also Published As

Publication number	Publication date
US4263197A (en)	1981-04-21
EP0000331B1 (fr)	1983-12-28
CA1103385A (fr)	1981-06-16
JPS6252079B2 (fr)	1987-11-04
PL207862A1 (pl)	1979-02-26
DE2862357D1 (en)	1984-02-02
CS194848B2 (en)	1979-12-31
PL106520B1 (pl)	1979-12-31
JPS5413557A (en)	1979-02-01
SU735173A3 (ru)	1980-05-15

Legal Events

Date	Code	Title	Description
1978-11-28	PUAI	Public reference made under article 153(3) epc to a published international application that has entered the european phase	Free format text: ORIGINAL CODE: 0009012
1979-01-24	AK	Designated contracting states	Designated state(s): CH DE FR GB NL
1979-07-11	17P	Request for examination filed
1983-10-29	GRAA	(expected) grant	Free format text: ORIGINAL CODE: 0009210
1983-12-28	AK	Designated contracting states	Designated state(s): CH DE FR GB NL
1984-02-02	REF	Corresponds to:	Ref document number: 2862357 Country of ref document: DE Date of ref document: 19840202
1984-04-06	ET	Fr: translation filed
1984-10-25	PLBE	No opposition filed within time limit	Free format text: ORIGINAL CODE: 0009261
1984-10-25	STAA	Information on the status of an ep patent application or granted ep patent	Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT
1984-12-27	26N	No opposition filed
1987-06-30	PGFP	Annual fee paid to national office [announced via postgrant information from national office to epo]	Ref country code: NL Payment date: 19870630 Year of fee payment: 10
1989-01-01	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: NL Effective date: 19890101
1989-02-16	NLV4	Nl: lapsed or anulled due to non-payment of the annual fee
1989-04-14	PGFP	Annual fee paid to national office [announced via postgrant information from national office to epo]	Ref country code: FR Payment date: 19890414 Year of fee payment: 12
1989-06-20	PGFP	Annual fee paid to national office [announced via postgrant information from national office to epo]	Ref country code: CH Payment date: 19890620 Year of fee payment: 12
1990-05-29	PGFP	Annual fee paid to national office [announced via postgrant information from national office to epo]	Ref country code: GB Payment date: 19900529 Year of fee payment: 13
1990-06-30	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: CH Effective date: 19900630
1991-02-28	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: FR Effective date: 19910228
1991-02-28	REG	Reference to a national code	Ref country code: CH Ref legal event code: PL
1991-04-26	REG	Reference to a national code	Ref country code: FR Ref legal event code: ST
1991-06-15	PG25	Lapsed in a contracting state [announced via postgrant information from national office to epo]	Ref country code: GB Effective date: 19910615
1992-02-12	GBPC	Gb: european patent ceased through non-payment of renewal fee
1997-04-16	PGFP	Annual fee paid to national office [announced via postgrant information from national office to epo]	Ref country code: DE Payment date: 19970416 Year of fee payment: 20
2000-11-22	GBPC	Gb: european patent ceased through non-payment of renewal fee

Publication	Publication Date	Title
DE69007385T2 (de)	1994-10-13	Anthrachinon-Copolyester Farbstoffkonzentrate.
DE3920029C2 (de)	1999-05-20	Farbstoffe zum Färben von Kunststoffen
DE2409435C2 (de)	1982-09-23	Verfahren zum Färben von synthetischen Polyamiden in der Masse und Verwendung der gefärbten Masse
EP0273866B1 (fr)	1992-12-16	Compositions de matières à base du pigment rouge C.I. 177
EP0000331B1 (fr)	1983-12-28	Procédé de teinture de polyamides linéaires dans la masse au moyen de sels de colorants monoazoique chromifères 1:2; les fibres ainsi obtenues
DE1917278B2 (de)	1974-06-27	Monoazofarbstoffe, Verfahren zu deren Herstellung und Farbstoffzubereitungen
EP0603132B1 (fr)	1999-05-12	Cristaux mixtes de dicétopyrrolopyrroles sulfonés
DE2302481B2 (de)	1975-01-02	Disazopigment, Verfahren zu seiner Herstellung und seiner Verwendung
DE2546038C2 (fr)	1988-02-18
EP0635539B1 (fr)	1997-12-29	Polyamide coloré dans sa masse à l'aide de pigments de dicétopyrrolopyrole
EP0183651B1 (fr)	1990-05-23	Complexes de métaux, procédé pour leur préparation et leur utilisation
DE69720475T2 (de)	2003-10-30	1:2 eisenkomplex-azofarbstoffe
DE3932912A1 (de)	1991-04-11	Sterisch gehinderte aminogruppen enthaltende synthetische polyamide
EP0138749B1 (fr)	1989-08-23	Procédé de teinture des polyamides synthétiques dans la masse
EP0038548A2 (fr)	1981-10-28	Procédé de conditionnement de pigments organiques
EP0278913A2 (fr)	1988-08-17	Compositions de matière à base de pigments de complexes métalliques ainsi que de composés
DE2504787C2 (de)	1983-06-23	Chromkomplexfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung
DE2441924C3 (de)	1978-06-01	Disazopigmentfarbstoffe
DE1278639B (de)	1968-09-26	Verfahren zur Herstellung von wasserunloeslichen Anthrachinonfarbstoffen
EP0238443A2 (fr)	1987-09-23	Composés dicyanobenzanthroniques
CH627771A5 (de)	1982-01-29	Neue stabile modifikation eines isoindolinonpigmentes.
DE2444883A1 (de)	1975-04-03	Pigmentkomplexe und verfahren zu ihrer herstellung
DE2641043C3 (de)	1982-05-13	Massefärben von Polyamiden
DE2444904A1 (de)	1975-04-03	Metallkomplexe
DE3109351A1 (de)	1982-09-23	Verfahren zur spinnfaerbung von linearen synthetischen polyamiden, sowie verfahren zur herstellung von lithiumsalzen von metallkomplexfarbstoffen