PL51207B1

PL51207B1 -

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Info

Publication number: PL51207B1
Authority: PL; Poland
Prior art keywords: parts; formula; chs; dyes; acid
Prior art date: 1964-02-13

Application number

PL103721A

Other languages

English (en)

Polish (pl)

Inventor

Curt Muller dr

Original Assignee

Sandoz A G

Filing date

1964-02-13

Publication date

1966-02-25

1964-02-13 Application filed by Sandoz A G filed Critical Sandoz A G

1966-02-25 Publication of PL51207B1 publication Critical patent/PL51207B1/pl

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239000000975 dye Substances 0.000 claims description 34
239000000460 chlorine Substances 0.000 claims description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
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 description 3
238000000034 method Methods 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
125000000547 substituted alkyl group Chemical group 0.000 claims description 2
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 14
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 14
239000000243 solution Substances 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
150000001989 diazonium salts Chemical class 0.000 description 8
238000004043 dyeing Methods 0.000 description 8
239000012954 diazonium Substances 0.000 description 7
239000002270 dispersing agent Substances 0.000 description 7
235000010288 sodium nitrite Nutrition 0.000 description 7
229960000583 acetic acid Drugs 0.000 description 6
229920000728 polyester Polymers 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 5
239000002253 acid Substances 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
239000000155 melt Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
230000008878 coupling Effects 0.000 description 4
238000010168 coupling process Methods 0.000 description 4
238000005859 coupling reaction Methods 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
239000000835 fiber Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
XVYNBLCPQVDRCH-UHFFFAOYSA-N 2-amino-3-chloro-5-nitrobenzonitrile Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1C#N XVYNBLCPQVDRCH-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
238000006193 diazotization reaction Methods 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
239000005020 polyethylene terephthalate Substances 0.000 description 3
229920002994 synthetic fiber Polymers 0.000 description 3
239000012209 synthetic fiber Substances 0.000 description 3
-1 threads or plates Substances 0.000 description 3
MUHLVSZIVTURCZ-UHFFFAOYSA-N 2-amino-3-bromo-5-nitrobenzonitrile Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C=C1C#N MUHLVSZIVTURCZ-UHFFFAOYSA-N 0.000 description 2
229920004934 Dacron® Polymers 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000000129 anionic group Chemical group 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
239000001045 blue dye Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000003086 colorant Substances 0.000 description 2
239000004744 fabric Substances 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
238000009998 heat setting Methods 0.000 description 2
FPUKYOSOAAPHTN-UHFFFAOYSA-N n-[3-(diethylamino)phenyl]acetamide Chemical compound CCN(CC)C1=CC=CC(NC(C)=O)=C1 FPUKYOSOAAPHTN-UHFFFAOYSA-N 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000001044 red dye Substances 0.000 description 2
PNGBYKXZVCIZRN-UHFFFAOYSA-M sodium;hexadecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCCCCCS([O-])(=O)=O PNGBYKXZVCIZRN-UHFFFAOYSA-M 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000000859 sublimation Methods 0.000 description 2
230000008022 sublimation Effects 0.000 description 2
210000004243 sweat Anatomy 0.000 description 2
LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
229920001747 Cellulose diacetate Polymers 0.000 description 1
229920002284 Cellulose triacetate Polymers 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
241001366278 Leptotes marina Species 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
229920004933 Terylene® Polymers 0.000 description 1
NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
FWFYSCVKOMFJPL-UHFFFAOYSA-N [Na].C1=CC=C2C(C(C=3C4=CC=CC=C4C=CC=3)S(=O)(=O)O)=CC=CC2=C1 Chemical compound [Na].C1=CC=C2C(C(C=3C4=CC=CC=C4C=CC=3)S(=O)(=O)O)=CC=CC2=C1 FWFYSCVKOMFJPL-UHFFFAOYSA-N 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000001785 acacia senegal l. willd gum Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
OFZCIYFFPZCNJE-UHFFFAOYSA-N carisoprodol Chemical compound NC(=O)OCC(C)(CCC)COC(=O)NC(C)C OFZCIYFFPZCNJE-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000011109 contamination Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000005108 dry cleaning Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000000945 filler Substances 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
239000003517 fume Substances 0.000 description 1
230000004927 fusion Effects 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
238000000227 grinding Methods 0.000 description 1
159000000011 group IA salts Chemical class 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
235000019960 monoglycerides of fatty acid Nutrition 0.000 description 1
WEAJAFRCXNDNBY-UHFFFAOYSA-N n-[3-(diethylamino)phenyl]propanamide Chemical compound CCN(CC)C1=CC=CC(NC(=O)CC)=C1 WEAJAFRCXNDNBY-UHFFFAOYSA-N 0.000 description 1
MHGIJXSAUHOIDU-UHFFFAOYSA-N n-[3-(dimethylamino)phenyl]acetamide Chemical compound CN(C)C1=CC=CC(NC(C)=O)=C1 MHGIJXSAUHOIDU-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002826 nitrites Chemical class 0.000 description 1
230000001473 noxious effect Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
235000019422 polyvinyl alcohol Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000002000 scavenging effect Effects 0.000 description 1
239000000344 soap Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000007921 spray Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
239000001043 yellow dye Substances 0.000 description 1

PL103721A 1964-02-13 PL51207B1 (cs)