US3188164A - Polypropylene fibers dyed with 4-nitroacridone dyes - Google Patents
Polypropylene fibers dyed with 4-nitroacridone dyes Download PDFInfo
- Publication number
- US3188164A US3188164A US253040A US25304063A US3188164A US 3188164 A US3188164 A US 3188164A US 253040 A US253040 A US 253040A US 25304063 A US25304063 A US 25304063A US 3188164 A US3188164 A US 3188164A
- Authority
- US
- United States
- Prior art keywords
- hours
- nitroacridone
- break
- dyes
- dyed
- 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.)
- Expired - Lifetime
Links
- 239000000835 fiber Substances 0.000 title claims description 23
- -1 Polypropylene Polymers 0.000 title claims description 18
- 239000004743 Polypropylene Substances 0.000 title claims description 15
- 229920001155 polypropylene Polymers 0.000 title claims description 15
- MMGYSMZGRLZCAS-UHFFFAOYSA-N 4-nitro-10h-acridin-9-one Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C([N+](=O)[O-])=CC=C2 MMGYSMZGRLZCAS-UHFFFAOYSA-N 0.000 title claims description 5
- 239000000975 dye Substances 0.000 title description 15
- 150000001875 compounds Chemical class 0.000 claims description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 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 2
- 125000000129 anionic group Chemical group 0.000 description 2
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- FJNZOTVFXOADDQ-UHFFFAOYSA-N 1-nitro-10h-acridin-9-one Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] FJNZOTVFXOADDQ-UHFFFAOYSA-N 0.000 description 1
- ICFOIFBVAYOSBR-UHFFFAOYSA-N 2-methoxy-4-nitro-10h-acridin-9-one Chemical compound C1=CC=C2C(=O)C3=CC(OC)=CC([N+]([O-])=O)=C3NC2=C1 ICFOIFBVAYOSBR-UHFFFAOYSA-N 0.000 description 1
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 description 1
- 101001018064 Homo sapiens Lysosomal-trafficking regulator Proteins 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 102100033472 Lysosomal-trafficking regulator Human genes 0.000 description 1
- 235000010703 Modiola caroliniana Nutrition 0.000 description 1
- 244000038561 Modiola caroliniana Species 0.000 description 1
- 241000539618 Salma Species 0.000 description 1
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000243 solution 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
-
- 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
- Y10S8/908—Anionic emulsifiers for dyeing
-
- 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
- Y10S8/908—Anionic emulsifiers for dyeing
- Y10S8/912—Arylene sulfonate-formaldehyde condensate or alkyl aryl sulfonate
-
- 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
- Y10S8/913—Amphoteric emulsifiers for dyeing
- Y10S8/914—Amino carboxylic acids
-
- 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
- Y10S8/928—Polyolefin fiber
Definitions
- This invention relates to polypropylene fibers dyed Marasperse N is a ligno sulfonate. with 4-nitroarcridone dyes.
- Cyclopon AF is sodium N-acyl-N- methyhtaurate. It has been found that 4-nitroacridone and some of Sulframin AB is sodium alkyl-benzene-sulfonate. its derivatives act as disperse dyes for polypropylene What is claimed is: fibers when applied by more or less conventional means. 15 1.
- Polypropylene fiber dyed with a 4-nitroacridone dye The dyes display much better lightfastness when dyed selected from the group consisting of on polypropylene fibers than do the commercially avail- (a) a compound having the formula able dyes recommended by the fiber manufacturers,
- a dyebath was i made up having about 40 times the Weight of the fiber.
- the dyebath was simply Water containing 1% (based NE on fiber weight) of an anionic wetting agent such as N01 sulfl'amm AB and 1/2% (based on fiber Weight) of the wherein R is selected from the group consisting of iiged Tlheflfloth vlgastecrlltertedbat 501066 tecrnpferatuge 221x21 H, C1, and Br two of the RS being H,
- 6 ye a was ea 6 a a on or a on c a com ound havn th formula hours.
- the goods were then p I g e soaped 30 minutes at 70 C. in an aqueous solution of 40 about 2% sodium carbonate (based on fiber weight) and about 1% (based on fiber weight) of a suitable dispersing agent such as Sulframin AB.
- a suitable dispersing agent such as Sulframin AB
- Another set of dyeings was made using a similar pro- I cedure but with 2% dyestuff instead of /a%.
- 7-methyl-4-nitmaoririnna dn Very slight break at 40 hours; slight break at 60 hours; another slight break at 80 hours.
- 5-methylthio-4-nitroaeridone do Very slight break at 20 hours; slight break at 40 hours; another slight break at 60 hours.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
3,188,164 POLYPROPYLENE FIBERS DYED WITH 4-NITROACRIDONE DYES Joseph W. Dehn, Jr., Great Neck, and Harold J. Kuhefuss,
United States Patent,
. Patented June 8, 1965 "ice The test pieces were all examined at 20-hour intervals up to 80 hours. Changes were noted, at least until a distinct break occurred. Lightfastness tests were made in the conventional way on the Fade-O-Meter.
Brooklyn, N.Y and John J. Maituer, Hazlet, N .J., and The preparation of the dimethoxy-4-nitroacridone dyes Auth9ny Salma, New York, to t i described in application Serial No. 152,670, filed No g g figg 'p New York, -i a corporahon vember 15, 1961. The preparation of 5-1nethy1thio-4- nitroacridone (S-methyhnercapto-4-nitroacridone) is de- Drawing Filed 1963 253040 scribed in application Serial No. 237,394, filed November 6 Claims. (Cl. 8-55) I 10 13 1962 This invention relates to polypropylene fibers dyed Marasperse N is a ligno sulfonate. with 4-nitroarcridone dyes. Cyclopon AF is sodium N-acyl-N- methyhtaurate. It has been found that 4-nitroacridone and some of Sulframin AB is sodium alkyl-benzene-sulfonate. its derivatives act as disperse dyes for polypropylene What is claimed is: fibers when applied by more or less conventional means. 15 1. Polypropylene fiber dyed with a 4-nitroacridone dye The dyes display much better lightfastness when dyed selected from the group consisting of on polypropylene fibers than do the commercially avail- (a) a compound having the formula able dyes recommended by the fiber manufacturers,
The detailed procedure that followsillustrates a specific embodiment of this invention.
EXAMPLE A mixture of 3.00 g. of the dye, 1.00 g. of Marasperse N, and 1.00 g. of Cyclopon AF was combined with water 1 and ground with a hand muller to disperse the dye. After h R 1 d f h f H the material was oven dried, it was ground to a powder W erem Se ecte group conslstmg o with mortar and pestle and used to make up the dyebath. and CHHO at leastfme R bemg A convenient weight of polypropylene fiber in the form 09) a compound havmg the formula of cloth was scoured minutes at 70 C. in an aqueous 0 R solution of 1% (based on fiber weight) of an anionic 30 I wetting agent such as Sulframin AB and 0.25% (based R- .R on fiber weight) of sodium carbonate, A dyebath was i made up having about 40 times the Weight of the fiber. The dyebath was simply Water containing 1% (based NE on fiber weight) of an anionic wetting agent such as N01 sulfl'amm AB and 1/2% (based on fiber Weight) of the wherein R is selected from the group consisting of iiged Tlheflfloth vlgastecrlltertedbat 501066 tecrnpferatuge 221x21 H, C1, and Br two of the RS being H,
6 ye a was ea 6 a a on or a on c a com ound havn th formula hours. To remove surface dye, the goods were then p I g e soaped 30 minutes at 70 C. in an aqueous solution of 40 about 2% sodium carbonate (based on fiber weight) and about 1% (based on fiber weight) of a suitable dispersing agent such as Sulframin AB. The goods were then rinsed and dried.
Another set of dyeings was made using a similar pro- I cedure but with 2% dyestuff instead of /a%.
The table below gives specific examples, showing the wheleln one R 15 H and the other R 15 a dyestuff used, its color on polypropylene fiber, and the 7-II1ethY1-4-I1itI0aefid0ne, and lightfastness. (e) 5-methylthio-4-nitroacridone.
Dyed polypropylene fiber Dyestuii Color Light iastness 4-nitroaeridone -1 Yellow No break at 80 hours. 2-methoxy-4-nitroacridone Noticeable break at 80 hours. 5-meth0xy-4-nitrnar-ridnne d N oticeable break at 40 hours. 7-methoxy-4-nih'oacridone No break at 80 hours. 2, fi-dimethoxyt-nitroacridone Orange Vefiy slight break at 40 hours; slight break at 80 OUIS. 2, 7-dhnethoxy-4-rutroacridone Mauve Very slight break at 20 hours; slight break at 40 hours; no additional break at hours; slight break at hours. 5, 7-djmethoxy-4-nitroasridone Pink Slight break st 80 hours. 5, 8-dimethoxy-4-nitroacridone do Distinct break at 20 hours. 6,7-(or 7, 8-)-dirnethoxy-4-nitroacridone do V ry slight break at 40 hours; slight break at 80 ours. l-chloro-t-nitroacridone Orange Very slight break at 20 hours; slight break at 40 hours; distinct break at 60 hours. 2Oh10r0-4-nitroacririnna '.dn Slihght break at 40 hours; noticeable break at 80 OUTS. 2-bromo-4-nitrnar-ridnna rlo Slight break at 40 hours; another slight break at 60 hours; another slight break at 80 hours. 7-bromo-4-nltroacridone Yellow Slight break st 60 hours; noticeable break at 80 OUTS. 7-methyl-4-nitmaoririnna dn Very slight break at 40 hours; slight break at 60 hours; another slight break at 80 hours. 5-methylthio-4-nitroaeridone do Very slight break at 20 hours; slight break at 40 hours; another slight break at 60 hours.
3 4 2. Polypropylene fiber dyed with a dye having the 4. Polypropylene fiber dyed with a dye having the formula formula i f 1? 15 I R 5 l) R \I/\ I I R N09 N02 wherein R is selected from the group consisting of H and 10 wherein R is H and the other R is CH O. CH O, at least one R being H. '5. Polypropylene fiber dyed with 7-methyl-4-nitro- 3. Polypropylene fiber dyed With a dye having the acridone. formula 6. Polypropylene fiber dyed with 5-methylthio-4- O R 15 nitroacridone. u R References Cited by the Examiner 1 UNITED STATES PATENTS 2,005,303 6/35 Spiegler et al. 260279 X NH 20 3,054,793 9/62 Howard et a1. 260 279 X N01 3,074,950 1/63 Deusche et al. 260-279 wherein R is selected from the group consisting of H, Cl, and Br, two of the Rs being H. NORMAN G. TORCHIN, Primary Examiner.
Claims (1)
1. POLYPROPYLENE FIBER DYED WITH A 4-NITROACRIDONE DYE SELECTED FROM THE GROUP CONSISTING OF (A) A COMPOUND HAVING THE FORMULA
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US253040A US3188164A (en) | 1963-01-22 | 1963-01-22 | Polypropylene fibers dyed with 4-nitroacridone dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US253040A US3188164A (en) | 1963-01-22 | 1963-01-22 | Polypropylene fibers dyed with 4-nitroacridone dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3188164A true US3188164A (en) | 1965-06-08 |
Family
ID=22958580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US253040A Expired - Lifetime US3188164A (en) | 1963-01-22 | 1963-01-22 | Polypropylene fibers dyed with 4-nitroacridone dyes |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3188164A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3541099A (en) * | 1966-01-21 | 1970-11-17 | Geigy Ag J R | Nitro-acridone dyestuffs |
| DE1569775B1 (en) * | 1966-01-21 | 1970-11-19 | Geigy Ag J R | Process for the production of nitro dyes of the acridone series |
| US3624255A (en) * | 1966-01-21 | 1971-11-30 | Ciba Geigy Ag | Nitro-acridone thioethers |
| US3624087A (en) * | 1967-07-17 | 1971-11-30 | Lilly Co Eli | Synthesis of acronycine and related compounds |
| US3681360A (en) * | 1971-04-09 | 1972-08-01 | Hoffmann La Roche | Antiviral substituted acridanones |
| US3975150A (en) * | 1973-08-24 | 1976-08-17 | Bayer Aktiengesellschaft | Transfer printing process |
| US5593459A (en) * | 1994-10-24 | 1997-01-14 | Gamblin; Rodger L. | Surfactant enhanced dyeing |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2005303A (en) * | 1935-06-18 | Dyeing of cellulose derivatives | ||
| US3054793A (en) * | 1956-06-15 | 1962-09-18 | Ici Ltd | New water soluble nitro dyestuffs containing a mono- or di-halogeno-1:3:5-triazinyl-(2)-amino group |
| US3074950A (en) * | 1959-08-22 | 1963-01-22 | Basf Ag | Process for producing a modification of gamma 7,14-dioxo-5,7,12,14-tetrahydroquinolino-(2,3-b) acridine |
-
1963
- 1963-01-22 US US253040A patent/US3188164A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2005303A (en) * | 1935-06-18 | Dyeing of cellulose derivatives | ||
| US3054793A (en) * | 1956-06-15 | 1962-09-18 | Ici Ltd | New water soluble nitro dyestuffs containing a mono- or di-halogeno-1:3:5-triazinyl-(2)-amino group |
| US3074950A (en) * | 1959-08-22 | 1963-01-22 | Basf Ag | Process for producing a modification of gamma 7,14-dioxo-5,7,12,14-tetrahydroquinolino-(2,3-b) acridine |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3541099A (en) * | 1966-01-21 | 1970-11-17 | Geigy Ag J R | Nitro-acridone dyestuffs |
| DE1569775B1 (en) * | 1966-01-21 | 1970-11-19 | Geigy Ag J R | Process for the production of nitro dyes of the acridone series |
| US3624255A (en) * | 1966-01-21 | 1971-11-30 | Ciba Geigy Ag | Nitro-acridone thioethers |
| US3624087A (en) * | 1967-07-17 | 1971-11-30 | Lilly Co Eli | Synthesis of acronycine and related compounds |
| US3681360A (en) * | 1971-04-09 | 1972-08-01 | Hoffmann La Roche | Antiviral substituted acridanones |
| US3975150A (en) * | 1973-08-24 | 1976-08-17 | Bayer Aktiengesellschaft | Transfer printing process |
| US5593459A (en) * | 1994-10-24 | 1997-01-14 | Gamblin; Rodger L. | Surfactant enhanced dyeing |
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