CH496060A - Verfahren zur Herstellung von urethangruppenhaltigen Farbstoffen - Google Patents

Verfahren zur Herstellung von urethangruppenhaltigen Farbstoffen

Info

Publication number: CH496060A
Authority: CH; Switzerland
Prior art keywords: sep; diisocyanate; blue; acid; red
Prior art date: 1966-11-14

Application number

CH1442767A

Other languages

German (de)

English (en)

Inventor

Konrad Dr Nonn

Original Assignee

Bayer 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.)

1966-11-14

Filing date

1967-10-16

Publication date

1970-09-15

1967-10-16 Application filed by Bayer Ag filed Critical Bayer Ag

1970-09-15 Publication of CH496060A publication Critical patent/CH496060A/de

Links

239000000975 dye Substances 0.000 title claims description 39
238000000034 method Methods 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 6
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims description 6
-1 3-chloro-tolylene Chemical group 0.000 claims description 111
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
125000001424 substituent group Chemical group 0.000 claims description 16
230000008878 coupling Effects 0.000 claims description 15
238000010168 coupling process Methods 0.000 claims description 15
238000005859 coupling reaction Methods 0.000 claims description 15
239000012948 isocyanate Substances 0.000 claims description 15
UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 claims description 14
150000002513 isocyanates Chemical class 0.000 claims description 14
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 12
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 7
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 7
239000000987 azo dye Substances 0.000 claims description 7
239000000049 pigment Substances 0.000 claims description 7
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 7
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 6
239000001000 anthraquinone dye Chemical class 0.000 claims description 5
WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 4
125000000542 sulfonic acid group Chemical group 0.000 claims description 4
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 claims description 2
RHDSDYPMXWSJEC-UHFFFAOYSA-N 5,6-diisocyanato-1,3,5-tri(propan-2-yl)cyclohexa-1,3-diene Chemical compound CC(C)C1=CC(N=C=O)(C(C)C)C(N=C=O)C(C(C)C)=C1 RHDSDYPMXWSJEC-UHFFFAOYSA-N 0.000 claims description 2
238000004043 dyeing Methods 0.000 claims description 2
239000000463 material Substances 0.000 claims description 2
239000000123 paper Substances 0.000 claims description 2
239000004033 plastic Substances 0.000 claims description 2
229920003023 plastic Polymers 0.000 claims description 2
239000004753 textile Substances 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims 3
238000004040 coloring Methods 0.000 claims 1
239000003973 paint Substances 0.000 claims 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 7
239000000203 mixture Substances 0.000 description 7
150000003254 radicals Chemical class 0.000 description 7
MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 6
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 6
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 5
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
150000003931 anilides Chemical class 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
NODVFTSWIAFZKL-UHFFFAOYSA-N 2-(4-nitrophenyl)-1h-pyrazol-5-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1NC(=O)C=C1 NODVFTSWIAFZKL-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
239000001044 red dye Substances 0.000 description 3
RYMMNSVHOKXTNN-UHFFFAOYSA-N 1,3-dichloro-5-methylbenzene Chemical compound CC1=CC(Cl)=CC(Cl)=C1 RYMMNSVHOKXTNN-UHFFFAOYSA-N 0.000 description 2
KTXUOWUHFLBZPW-UHFFFAOYSA-N 1-chloro-3-(3-chlorophenyl)benzene Chemical group ClC1=CC=CC(C=2C=C(Cl)C=CC=2)=C1 KTXUOWUHFLBZPW-UHFFFAOYSA-N 0.000 description 2
FDGAEAYZQQCBRN-UHFFFAOYSA-N 3-amino-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1N FDGAEAYZQQCBRN-UHFFFAOYSA-N 0.000 description 2
LYCCVBLUKJRDOF-UHFFFAOYSA-N 3-amino-4-nitrobenzoic acid Chemical compound NC1=CC(C(O)=O)=CC=C1[N+]([O-])=O LYCCVBLUKJRDOF-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
125000004442 acylamino group Chemical class 0.000 description 2
239000003513 alkali Substances 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000004453 alkoxycarbonyl group Chemical class 0.000 description 2
125000004414 alkyl thio group Chemical class 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
125000005110 aryl thio group Chemical class 0.000 description 2
125000004104 aryloxy group Chemical group 0.000 description 2
150000001555 benzenes Chemical class 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
125000004663 dialkyl amino group Chemical class 0.000 description 2
150000008049 diazo compounds Chemical class 0.000 description 2
TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
125000005442 diisocyanate group Chemical group 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
JTVHJWVDFCVGBG-UHFFFAOYSA-N n-(2-methyl-5-nitrophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC([N+]([O-])=O)=CC=C1C JTVHJWVDFCVGBG-UHFFFAOYSA-N 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
239000001054 red pigment Substances 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
125000000547 substituted alkyl group Chemical group 0.000 description 2
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
XKGOGOLMEYUITI-UHFFFAOYSA-N (3-amino-4-chlorophenyl)methanol Chemical compound NC1=CC(CO)=CC=C1Cl XKGOGOLMEYUITI-UHFFFAOYSA-N 0.000 description 1
WPUAJRPNIWMHET-UHFFFAOYSA-N (3-amino-4-methoxyphenyl)methanol Chemical compound COC1=CC=C(CO)C=C1N WPUAJRPNIWMHET-UHFFFAOYSA-N 0.000 description 1
AXKGIPZJYUNAIW-UHFFFAOYSA-N (4-aminophenyl)methanol Chemical compound NC1=CC=C(CO)C=C1 AXKGIPZJYUNAIW-UHFFFAOYSA-N 0.000 description 1
PXRFIHSUMBQIOK-CVBJKYQLSA-L (z)-octadec-9-enoate;tin(2+) Chemical compound [Sn+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O PXRFIHSUMBQIOK-CVBJKYQLSA-L 0.000 description 1
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
VZWWZEJXAIOUFX-UHFFFAOYSA-N 1,3-bis(3-isocyanato-4-methylphenyl)urea Chemical compound C1=C(N=C=O)C(C)=CC=C1NC(=O)NC1=CC=C(C)C(N=C=O)=C1 VZWWZEJXAIOUFX-UHFFFAOYSA-N 0.000 description 1
NONFXPKKKRJFEM-UHFFFAOYSA-N 1,3-dichloro-2,4-diisocyanato-5-methylbenzene Chemical compound CC1=C(N=C=O)C(Cl)=C(N=C=O)C(Cl)=C1 NONFXPKKKRJFEM-UHFFFAOYSA-N 0.000 description 1
QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
GVEDOIATHPCYGS-UHFFFAOYSA-N 1-methyl-3-(3-methylphenyl)benzene Chemical group CC1=CC=CC(C=2C=C(C)C=CC=2)=C1 GVEDOIATHPCYGS-UHFFFAOYSA-N 0.000 description 1
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
AKKHQNDBSBENFW-UHFFFAOYSA-N 2,4-diisocyanato-1-(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(N=C=O)C=C1N=C=O AKKHQNDBSBENFW-UHFFFAOYSA-N 0.000 description 1
SSVDEQPRFIXROF-UHFFFAOYSA-N 2,5-dichloro-5,6-diisocyanatocyclohexa-1,3-diene Chemical compound ClC1(C(C=C(C=C1)Cl)N=C=O)N=C=O SSVDEQPRFIXROF-UHFFFAOYSA-N 0.000 description 1
AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
PNHJHBPPGNNIFS-UHFFFAOYSA-N 2-chloro-1,3-diisocyanato-4-methylbenzene Chemical compound CC1=CC=C(N=C=O)C(Cl)=C1N=C=O PNHJHBPPGNNIFS-UHFFFAOYSA-N 0.000 description 1
MKMDCEXRIPLNGJ-UHFFFAOYSA-N 2-phenyl-1h-pyrazol-5-one Chemical compound N1=C(O)C=CN1C1=CC=CC=C1 MKMDCEXRIPLNGJ-UHFFFAOYSA-N 0.000 description 1
ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
DMGFVJVLVZOSOE-UHFFFAOYSA-N 3-amino-4-chlorobenzoic acid Chemical compound NC1=CC(C(O)=O)=CC=C1Cl DMGFVJVLVZOSOE-UHFFFAOYSA-N 0.000 description 1
ZYZHOAZMRASIMD-UHFFFAOYSA-N 3-amino-n-(2-hydroxyethyl)-4-methoxybenzamide Chemical compound COC1=CC=C(C(=O)NCCO)C=C1N ZYZHOAZMRASIMD-UHFFFAOYSA-N 0.000 description 1
WOTZWRBPQWOVPE-UHFFFAOYSA-N 3-oxo-n-(2,4,5-trichlorophenyl)butanamide Chemical compound CC(=O)CC(=O)NC1=CC(Cl)=C(Cl)C=C1Cl WOTZWRBPQWOVPE-UHFFFAOYSA-N 0.000 description 1
JNFGLYJROFAOQP-UHFFFAOYSA-N 4-amino-3-methoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1N JNFGLYJROFAOQP-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
PCTPXAOHSBZIAQ-UHFFFAOYSA-N CC(CC(NC(C(Cl)=C(C(Cl)=C1Cl)Cl)=C1Cl)=O)=O Chemical compound CC(CC(NC(C(Cl)=C(C(Cl)=C1Cl)Cl)=C1Cl)=O)=O PCTPXAOHSBZIAQ-UHFFFAOYSA-N 0.000 description 1
JVDRDXZIROPCPN-UHFFFAOYSA-N CC(CC(NC1=C(C)C=C(C)C(Cl)=C1)=O)=O Chemical compound CC(CC(NC1=C(C)C=C(C)C(Cl)=C1)=O)=O JVDRDXZIROPCPN-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
OMRDSWJXRLDPBB-UHFFFAOYSA-N N=C=O.N=C=O.C1CCCCC1 Chemical compound N=C=O.N=C=O.C1CCCCC1 OMRDSWJXRLDPBB-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
FIQIEWYXLLEXNR-UHFFFAOYSA-N [O-][N+](=O)S(=O)(=O)[N+]([O-])=O Chemical compound [O-][N+](=O)S(=O)(=O)[N+]([O-])=O FIQIEWYXLLEXNR-UHFFFAOYSA-N 0.000 description 1
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical class CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 description 1
DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
125000005138 alkoxysulfonyl group Chemical class 0.000 description 1
125000003806 alkyl carbonyl amino group Chemical group 0.000 description 1
125000004656 alkyl sulfonylamino group Chemical group 0.000 description 1
125000004658 aryl carbonyl amino group Chemical group 0.000 description 1
125000005161 aryl oxy carbonyl group Chemical class 0.000 description 1
125000005142 aryl oxy sulfonyl group Chemical class 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
125000004657 aryl sulfonyl amino group Chemical group 0.000 description 1
125000000732 arylene group Chemical group 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000005521 carbonamide group Chemical class 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 1
239000012975 dibutyltin dilaurate Substances 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000000976 ink Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
LZKLAOYSENRNKR-LNTINUHCSA-N iron;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LZKLAOYSENRNKR-LNTINUHCSA-N 0.000 description 1
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
HWSZZLVAJGOAAY-UHFFFAOYSA-L lead(II) chloride Chemical compound Cl[Pb]Cl HWSZZLVAJGOAAY-UHFFFAOYSA-L 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000013508 migration Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
YTKNYOWCICFXOW-UHFFFAOYSA-N n-(2,4-dichlorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(Cl)C=C1Cl YTKNYOWCICFXOW-UHFFFAOYSA-N 0.000 description 1
FGVXALCWFWMFBD-UHFFFAOYSA-N n-(2,4-dinitrophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O FGVXALCWFWMFBD-UHFFFAOYSA-N 0.000 description 1
HLMZZYYGOKOOTA-UHFFFAOYSA-N n-(2,5-dichlorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC(Cl)=CC=C1Cl HLMZZYYGOKOOTA-UHFFFAOYSA-N 0.000 description 1
BZKOGFAXBSPQRB-UHFFFAOYSA-N n-(2-chloro-4-nitrophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C([N+]([O-])=O)C=C1Cl BZKOGFAXBSPQRB-UHFFFAOYSA-N 0.000 description 1
BFVHBHKMLIBQNN-UHFFFAOYSA-N n-(2-chlorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1Cl BFVHBHKMLIBQNN-UHFFFAOYSA-N 0.000 description 1
AWRWFTFHIONLAG-UHFFFAOYSA-N n-(2-methoxy-4-nitrophenyl)-3-oxobutanamide Chemical compound COC1=CC([N+]([O-])=O)=CC=C1NC(=O)CC(C)=O AWRWFTFHIONLAG-UHFFFAOYSA-N 0.000 description 1
LUYDCBSYHLMSBP-UHFFFAOYSA-N n-(2-methoxy-5-nitrophenyl)-3-oxobutanamide Chemical compound COC1=CC=C([N+]([O-])=O)C=C1NC(=O)CC(C)=O LUYDCBSYHLMSBP-UHFFFAOYSA-N 0.000 description 1
KYYRTDXOHQYZPO-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC=CC=C1NC(=O)CC(C)=O KYYRTDXOHQYZPO-UHFFFAOYSA-N 0.000 description 1
TVZIWRMELPWPPR-UHFFFAOYSA-N n-(2-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C TVZIWRMELPWPPR-UHFFFAOYSA-N 0.000 description 1
ZBRNSHANCDLJAA-UHFFFAOYSA-N n-(2-nitrophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1[N+]([O-])=O ZBRNSHANCDLJAA-UHFFFAOYSA-N 0.000 description 1
NBLAONBKZUTBFR-UHFFFAOYSA-N n-(3-chloro-2-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC(Cl)=C1C NBLAONBKZUTBFR-UHFFFAOYSA-N 0.000 description 1
MTPKMGABYQNMMG-UHFFFAOYSA-N n-(3-chlorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC(Cl)=C1 MTPKMGABYQNMMG-UHFFFAOYSA-N 0.000 description 1
KQAQKCOLRNMYFK-UHFFFAOYSA-N n-(3-nitrophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC([N+]([O-])=O)=C1 KQAQKCOLRNMYFK-UHFFFAOYSA-N 0.000 description 1
MOUVJGIRLPZEES-UHFFFAOYSA-N n-(4-chloro-2,5-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(NC(=O)CC(C)=O)=C(OC)C=C1Cl MOUVJGIRLPZEES-UHFFFAOYSA-N 0.000 description 1
ODFRAIZRJMUPCP-UHFFFAOYSA-N n-(4-chloro-2-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(Cl)C=C1C ODFRAIZRJMUPCP-UHFFFAOYSA-N 0.000 description 1
KLMIREBDPKVUQJ-UHFFFAOYSA-N n-(4-chloro-2-nitrophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(Cl)C=C1[N+]([O-])=O KLMIREBDPKVUQJ-UHFFFAOYSA-N 0.000 description 1
WWROGCAUSKGAMX-UHFFFAOYSA-N n-(4-ethoxyphenyl)-3-oxobutanamide Chemical compound CCOC1=CC=C(NC(=O)CC(C)=O)C=C1 WWROGCAUSKGAMX-UHFFFAOYSA-N 0.000 description 1
QBHQQQKWEKZEHK-UHFFFAOYSA-N n-(4-methoxy-2-nitrophenyl)-3-oxobutanamide Chemical compound COC1=CC=C(NC(=O)CC(C)=O)C([N+]([O-])=O)=C1 QBHQQQKWEKZEHK-UHFFFAOYSA-N 0.000 description 1
ZZSDMAAHJFGGSU-UHFFFAOYSA-N n-(4-methyl-2-nitrophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(C)C=C1[N+]([O-])=O ZZSDMAAHJFGGSU-UHFFFAOYSA-N 0.000 description 1
MJGLMEMIYDUEHA-UHFFFAOYSA-N n-(4-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(C)C=C1 MJGLMEMIYDUEHA-UHFFFAOYSA-N 0.000 description 1
KCXJQNDNGLRYBN-UHFFFAOYSA-N n-(4-nitrophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C([N+]([O-])=O)C=C1 KCXJQNDNGLRYBN-UHFFFAOYSA-N 0.000 description 1
SGUFPRJAMBWKAZ-UHFFFAOYSA-N n-(5-chloro-2-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC(Cl)=CC=C1C SGUFPRJAMBWKAZ-UHFFFAOYSA-N 0.000 description 1
125000004957 naphthylene group Chemical group 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
150000004707 phenolate Chemical class 0.000 description 1
239000005056 polyisocyanate Substances 0.000 description 1
229920001228 polyisocyanate Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000005156 substituted alkylene group Chemical group 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
DIORMHZUUKOISG-UHFFFAOYSA-N sulfoformic acid Chemical compound OC(=O)S(O)(=O)=O DIORMHZUUKOISG-UHFFFAOYSA-N 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
125000005628 tolylene group Chemical group 0.000 description 1
PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical group C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000001043 yellow dye Substances 0.000 description 1
239000001052 yellow pigment Substances 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/2409—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position not provided for in one of the sub groups C09B5/26 - C09B5/62
- C09B5/2436—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position not provided for in one of the sub groups C09B5/26 - C09B5/62 only nitrogen-containing hetero rings
- C09B5/2445—Phtaloyl isoindoles
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/18—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group
- C09B43/26—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group with polyfunctional acylating agents
- C09B43/266—Di-or polyisocyanates

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heat Sensitive Colour Forming Recording (AREA)
Polyurethanes Or Polyureas (AREA)

CH1442767A 1966-11-14 1967-10-16 Verfahren zur Herstellung von urethangruppenhaltigen Farbstoffen CH496060A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF0050668		1966-11-14

Publications (1)

Publication Number	Publication Date
CH496060A true CH496060A (de)	1970-09-15

Family

ID=7103983

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1442767A CH496060A (de)	1966-11-14	1967-10-16	Verfahren zur Herstellung von urethangruppenhaltigen Farbstoffen

Country Status (6)

Country	Link
BE (1)	BE706420A (da)
CH (1)	CH496060A (da)
DE (1)	DE1644180A1 (da)
DK (1)	DK120766B (da)
GB (1)	GB1141654A (da)
NL (1)	NL6715442A (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN108148176B (zh) *	2018-01-09	2020-12-29	安徽艾佩科电子材料有限公司	一种用于电阻型存储材料的聚氨酯

1966
- 1966-11-14 DE DE19661644180 patent/DE1644180A1/de active Pending
1967
- 1967-10-16 CH CH1442767A patent/CH496060A/de not_active IP Right Cessation
- 1967-10-31 GB GB4942067A patent/GB1141654A/en not_active Expired
- 1967-11-13 BE BE706420D patent/BE706420A/xx unknown
- 1967-11-13 DK DK564867A patent/DK120766B/da unknown
- 1967-11-14 NL NL6715442A patent/NL6715442A/xx unknown

Also Published As

Publication number	Publication date
DE1644180A1 (de)	1971-10-07
DK120766B (da)	1971-07-12
NL6715442A (da)	1968-05-15
BE706420A (da)	1968-03-18
GB1141654A (en)	1969-01-29

Legal Events

Date	Code	Title	Description
1980-06-30	PL	Patent ceased

Publication	Publication Date	Title
DE1768892A1 (de)	1972-04-27	Verfahren zur Herstellung von Disazopigmenten
DE1544460C3 (de)	1975-09-25	Bis-(acetoacetyl)-arylendiamiddisazopigmente
DE1297259B (de)	1969-06-12	Verfahren zur Herstellung von Farbstoffen
DE2062717A1 (en)	1972-06-29	Azo dyes - from 2,6-diaminopyridine derivatives
DE2901121C2 (da)	1989-10-05
DE2441524A1 (de)	1975-03-13	Azofarbstoffe, ihre herstellung und verwendung
DE2236250A1 (de)	1973-02-08	Neue diazo-pigmente, deren herstellung und verwendung
CH625819A5 (da)	1981-10-15
DE943901C (de)	1956-06-01	Verfahren zur Herstellung neuer Carbonsaeureamidderivate von Azofarbstoffen
DE2457687A1 (de)	1976-06-16	Neue azofarbstoffe
CH496060A (de)	1970-09-15	Verfahren zur Herstellung von urethangruppenhaltigen Farbstoffen
DE1719069A1 (de)	1971-08-12	Neue Disazofarbstoffpigmente und Verfahren zu deren Herstellung
CH519007A (de)	1972-02-15	Verfahren zur Herstellung neuer wasserunlöslicher Azoverbindungen
DE2544568C3 (de)	1979-02-08	Sulfonsäuregruppenfreie Azofarbstoffe, Verfahren zu ihrer Herstellung und deren Verwendung als Pigmente in Lacken, Druckfarben oder Kunststoffen
DE4409902A1 (de)	1995-09-28	Isoindolinazopigmente
DE2531776A1 (de)	1977-02-03	Azopigmente mit einem phthalazonrest
EP0064952B1 (de)	1985-07-24	Neue Monoazopigmente
AT221680B (de)	1962-06-12	Verfahren zur Herstellung von neuen, zur Wollfärbung geeigneten Azofarbstoffen
DE2138014A1 (de)	1973-02-08	Disazofarbstoffe
DE2001916C (de)	1973-03-15	Wasserunlösliche Monoazofarbstoffe und ihre Verwendung
DE1644205C3 (de)	1975-10-30	Wasserunlösliche Monoazofarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung
DE2059677A1 (de)	1972-06-08	Azopigmente der ss-Hydroxynaphthoesaeurereihe
CH499595A (de)	1970-11-30	Verfahren zur Herstellung von sulfonsäuregruppenfreien Monoazofarbstoffen
DE2003540A1 (de)	1970-08-27	Orange bis violette kationische Azofarbstoffe
DE2218645A1 (de)	1973-10-25	Trisazofarbstoffe