DE389401C - Process for increasing the receptivity of cellulose esters for dyes - Google Patents
Process for increasing the receptivity of cellulose esters for dyesInfo
- Publication number
- DE389401C DE389401C DEB105609D DEB0105609D DE389401C DE 389401 C DE389401 C DE 389401C DE B105609 D DEB105609 D DE B105609D DE B0105609 D DEB0105609 D DE B0105609D DE 389401 C DE389401 C DE 389401C
- Authority
- DE
- Germany
- Prior art keywords
- percent
- dyes
- treated
- solution
- cellulose acetate
- 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
Links
- 239000000975 dye Substances 0.000 title claims description 6
- 229920002678 cellulose Polymers 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 238000007127 saponification reaction Methods 0.000 claims description 5
- 238000010521 absorption reaction Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 238000004043 dyeing Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 13
- 229940081735 acetylcellulose Drugs 0.000 description 13
- 229920002301 cellulose acetate Polymers 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000010446 mirabilite Substances 0.000 description 6
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 6
- DETXZQGDWUJKMO-UHFFFAOYSA-N 2-hydroxymethanesulfonic acid Chemical compound OCS(O)(=O)=O DETXZQGDWUJKMO-UHFFFAOYSA-N 0.000 description 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- 239000008098 formaldehyde solution Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 3
- VUTBELPREDJDDH-UHFFFAOYSA-N 4-amino-5-hydroxymethyl-2-methylpyrimidine Chemical compound CC1=NC=C(CO)C(N)=N1 VUTBELPREDJDDH-UHFFFAOYSA-N 0.000 description 2
- 101100351256 Caenorhabditis elegans ccm-3 gene Proteins 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- CGLDLDBFLNXMGE-MDZDMXLPSA-N 2-[(e)-2-(9,10-dioxoanthracen-2-yl)ethenyl]anthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(/C=C/C=4C=C5C(=O)C6=CC=CC=C6C(C5=CC=4)=O)=CC=C3C(=O)C2=C1 CGLDLDBFLNXMGE-MDZDMXLPSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241000628997 Flos Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 description 1
- 229940017705 formaldehyde sulfoxylate Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 1
- 208000020442 loss of weight Diseases 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- CHHHXKFHOYLYRE-STWYSWDKSA-M potassium sorbate Chemical compound [K+].C\C=C\C=C\C([O-])=O CHHHXKFHOYLYRE-STWYSWDKSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/12—Aldehydes; Ketones
- D06M13/127—Mono-aldehydes, e.g. formaldehyde; Monoketones
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/32—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond
- D06M11/36—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond with oxides, hydroxides or mixed oxides; with salts derived from anions with an amphoteric element-oxygen bond
- D06M11/38—Oxides or hydroxides of elements of Groups 1 or 11 of the Periodic Table
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/40—Cellulose acetate
- D06P3/401—Cellulose acetate using acid dyes
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Description
Verfahren zur Erhöhung der Aufnahmefähigkeit von Celluloseestern für Farbstoffe. Es wurde gefunden, @daß sich die Aufnahmefähigkeit von Celluloseestern für Farbstoffe in vorteilhafter Weise dadurch erhöhen läßt, daß man die Celluloseester mit Verseifungsmitteln, denen in ihnen lösliche Aldehyde oder Oxyaldehyde zugesetzt sind, behandelt. Man erhält auf diese Weise Produkte, die sich leicht und gleichmäßig färben lassen.Process for increasing the absorption capacity of cellulose esters for Dyes. It has been found that the absorption capacity of cellulose esters for dyes can be increased in an advantageous manner that the cellulose ester with saponifying agents to which soluble aldehydes or oxyaldehydes are added are treated. In this way, products are obtained that are easy and even let dye.
Bei der Vorbehandlung mit den aldehydhaltigen Verseifungsmitteln bleiben Form, Festigkeit und Glanz der Faser erhalten, und (ler Gewichtsverlust ist dabei ein so geringer, wie er bisher noch bei keinem der bekannten Verseifungsverfahren erreicht wurde. Die Färbung der Faser kann auch gleichzeitig mit der V erseifung in dem Vorbehandlungsbad ausgeführt werden.Stick to the pretreatment with the aldehyde-containing saponification agents Preserve the shape, strength and shine of the fiber, and there is a loss of weight a lower level than has been seen in any of the known saponification processes was achieved. The coloring of the fiber can also occur simultaneously with the saponification are carried out in the pretreatment bath.
Beispiel i.Example i.
2,5 g Celluloseacetatseide werden in ioo ccm Barythydratlösung von 5 ° Be, welcher 2o ccm 3oprozentiger Formaldehyd zugesetzt sind, etwa io Minuten bei 6o° C behandelt und danach gründlich gespült.2.5 g of cellulose acetate silk are dissolved in 100 ccm of barythydrate solution 5 ° Be, to which 2o ccm of 3% formaldehyde has been added, about 10 minutes Treated at 60 ° C and then rinsed thoroughly.
Das so behandelte Färbegut wird mit 12 Prozent Anthraflavon-GC-Teig unter Zusatz von etwa 3 ccm Natronlauge q.o° Be, i bis 2 g Hydrosulfit conc. B. A. S. F.-Pulver und etwa io g Glaubersalz calc. pro Liter bei etwa 3o bis d.o° C während etwa 2o Minuten ausgefärbt. Die Celluloseacetatseide wirrt sodann in der üblichen Weise bei etwa 8o.°- C geseift und zeigt schöne, grünstichige Gelbfärbung.The dyed material treated in this way is made with 12 percent anthraflavone GC dough with the addition of about 3 cc of sodium hydroxide solution q.o ° Be, 1 to 2 g of hydrosulphite conc. B. A. S. F. powder and about 10 g Glauber's salt calc. per liter at about 3o to d.o ° C Colored for about 20 minutes. The cellulose acetate floss then tangles in the Usually soaped at around 80 ° C and shows a beautiful, greenish yellow color.
Beispiele. Man verfährt in der gleichen Weise wie in Beispiel i unter Ersatz der Formaldehydlösung durch io bis ii g Acetaldehyd.Examples. Proceed in the same way as in example i under Replacement of the formaldehyde solution with 10 to 2 g acetaldehyde.
Die so vorbehandelte Faser gibt beim Ausfärben mit io Prozent Indanthrenblau-GCD-Teig in der Küpe ein gleichmäßiges, leuchtendes Blau.The fiber pretreated in this way gives when dyed with 10 percent indanthrene blue GCD dough an even, bright blue in the vat.
Beispiel 3. Example 3.
2,5 g Celluloseacetatseide werden mit iooccm Strontiumhydroxydlösung von 1,2° Be und 1(2 g Glucose während 3 bis 5 Minuten bei 6o° C behandelt und sodann sorgfältig gespült.2.5 g of cellulose acetate silk are mixed with 10 ounces of strontium hydroxide solution of 1.2 ° Be and 1 (2 g of glucose for 3 to 5 minutes at 6o ° C and then treated rinsed carefully.
Beim Färben der so behandelten Celluloseacetatseide mit. Indantbrenblau-GCD-Teig erhält man ebenfalls schöne, blaue Töne.When dyeing the treated cellulose acetate silk with. Indanthene blue GCD batter you also get beautiful, blue tones.
Beispiel q..Example q ..
Die Vorbehandlung von 2,5g Acetylcelluloseseide geschieht in ioo ccm Wasser, dem o,8 ccm Natronlauge q.0° Be und q. ccm 3oprozentige Formaldehydlösung zugesetzt sind, bei etwa 6o° C während io Minuten.The pretreatment of 2.5 g acetyl cellulose silk is done in 100 ccm Water, the 0.8 ccm sodium hydroxide solution q 0 ° Be and q. ccm 3% formaldehyde solution are added, at about 60 ° C for 10 minutes.
Das gespülte Färbegut zeigt beim Färben mit = Prozent Pyramingelb G extra in der für substantive Farbstoffe üblichen Weise bei etwa 7o bis 8o° C eine vorzügliche Aufnahmefähigkeit für den Farbstoff.The rinsed dyed material shows when dyed with = percent pyramine yellow G extra in the usual manner for substantive dyes at approx 7o up to 80 ° C an excellent absorption capacity for the dye.
Beispiel 5.Example 5.
2,5 g Celluloseacetatseide werden bei 5o bis 6o° C mit einem Bad behandelt, das aus ioo ccm Wasser, o,8 cem Natronlauge 4o° Be und! 4 ccm 3oprozentiger Formaldehydlösung sowie 2' Prozent Pyramingelb G extra und i g Glaubersalz calc. besteht. Nach etwa l/,stündigein Umziehen erhält man eine leuchtend goldgelb gefärbte Celluloseacetatseide. Beispiel 6. 2,5g Celluloseacetatseide «erden bei 50 bis 6o° C etwa io Minuten lang mit einem Bat] aus 7,5 g Glyoxalsulfat und 2,5 ccm Natronlauge 4o° Be in i :2o ccm Wasserbehandelt und danach gründlich gespült.2.5 g of cellulose acetate silk are treated at 5o to 6o ° C with a bath made of 100 ccm of water, 0.8 cem of sodium hydroxide solution 40 ° Be and! 4 ccm 3 percent formaldehyde solution and 2 percent pyramine yellow G extra and ig Glauber's salt calc. consists. After about 1/2 hour of changing, a bright golden yellow colored cellulose acetate silk is obtained. Example 6. Ground 2.5 g of cellulose acetate silk at 50 to 60 ° C. for about 10 minutes with a bath of 7.5 g of glyoxal sulfate and 2.5 cc of sodium hydroxide solution 40 ° Be in 1: 20 cc of water and then rinsed thoroughly.
Eine Ausfärbung mit 1,5 Prozent Oxanvingrün G und io Prozent Glaubersalz bei etwa 70 bis 80° C ergibt ein schönes Grün. Beispiel 7. Man färbt 2,5 g Celluloseacetatseide, welche zuvor mit einer Lösung von 14 g mit Natronlauge neutralisierter Glyoxylsäure von 58 Prozent und 2,5 cctn Natronlauge von 40° B6 in i2o ccm Wasser von 5o bis 6o° C behandelt und dadurch teilweise verseift wurde, mit 1,5 Prozent Oxaminbraun R und io Prozent Glaubersalz bei 7o bis 8o° C aus. Beispiel 8. Man behandelt 2,5 g Celluloseacetatseide während io Minuten in einem 6o° C warmen Bade von ioo ccm Wasser, 2,5 ccm Natronlauge von do° B6 und 2o g Formaldehydbisulfitlösung,hergestellt aus NatriumbisttlfitlösUng von 40° Be -und der äquivalenten Menge Formaldehydlösung von 30 Prozent.Coloring with 1.5 percent Oxanving green G and 10 percent Glauber's salt at around 70 to 80 ° C results in a beautiful green. Example 7. 2.5 g of cellulose acetate silk are dyed, which has previously been treated with a solution of 14 g of 58 percent glyoxylic acid neutralized with sodium hydroxide solution and 2.5 cctn of sodium hydroxide solution at 40 ° B6 in 12o cc of water at 50 to 60 ° C and thereby partially was saponified, with 1.5 percent oxamine brown R and 10 percent Glauber's salt at 7o to 8o ° C. Example 8. 2.5 g of cellulose acetate silk are treated for 10 minutes in a 60 ° C. bath of 100 cc of water, 2.5 cc of sodium hydroxide solution of 10 ° B6 and 20 g of formaldehyde bisulfite solution, prepared from sodium bisulfite solution of 40 ° C. and the equivalent Amount of formaldehyde solution of 30 percent.
Nach gründlichem Spülen wird die vorbehandelte Kunstseide mit 4 Prozent Baumwollechtrot .4 BS unter Zusatz von io Prozent Glaubersalz calc. bei 70 bis 8o° C ausgefärbt.After thorough rinsing, the pretreated rayon is made with 4 percent cotton red .4 BS with the addition of 10 percent Glauber's salt calc. colored at 70 to 80 ° C.
Die Natronlauge und Formaldehydbisulfitlösung können ganz oder teilweise durch Natriumsulfit und Formaldehyd ersetzt werden. Beispiel c).The sodium hydroxide solution and formaldehyde bisulfite solution can be wholly or partially replaced by sodium sulfite and formaldehyde. Example c).
Die Vorbehandlung von 2"5g Celluloseacetatseide wird mit ii g Acetaldehy.dbisulfit-K)sung, hergestellt aus 2,53 g Acetaldehyd und 14,2 g Bisulfitlösung von 40° B6 und 2,5 ccm Natronlauge von 4o° Be in i2o ccm Wasser von 6o° C, während io Minuten vorgenommen.The pretreatment of 2 "5g cellulose acetate silk is with ii g Acetaldehy.dbisulfit-K) solution, made from 2.53 g of acetaldehyde and 14.2 g of bisulfite solution of 40 ° B6 and 2.5 cc sodium hydroxide solution at 40 ° Be in 120 cc water at 60 ° C for 10 minutes.
Eine Ausfärbung auf der so behandelten Seide mit 2 Prozent Indoinblau-BB-Pulver und 5 Prozent Alaun ist erheblich tiefer als eine gleiche Ausfärbung auf der nicht vorbehandelten Ware. Beispiel io. 2,5 g Celluloseacetatseide werden in 2,5 ccm Natronlauge von 4o° Be und 30- Formaldehv<lsulfoxylat (Rongalit C ) in 12o ccm Wasser bei So bis 6o' .C io Minuten lang umgezogen und nach gründlichem Spülen mit 4 Prozent Oxaminblau 3 B ausgefärbt. Beispiel ii. 5 kg Celluloseacetatseide werden in i 5o ccm einer Mischung aus 4o Teilen 3oprozentigem Formaldehyd und 6o Teilen Wasser unter anfänglichem Umziehen einige Zeit, etwa i Stunde, eingelegt und nach dem Auswinden io Minuten lang bei So bis 6o° C mit 15o ccm 2,5prozentiger Kalkmilch behandelt.A coloration on the silk treated in this way with 2 percent indoin blue BB powder and 5 percent alum is considerably deeper than the same coloration on the non-pretreated goods. Example io. 2.5 g of cellulose acetate silk are put into 2.5 cc sodium hydroxide solution of 40 ° Be and 30- formaldehyde sulfoxylate (Rongalit C ) in 12o cc of water at sun to 60 ° C. for 10 minutes and after thorough rinsing with 4 percent oxamine blue 3 B colored. Example ii. 5 kg of cellulose acetate silk are placed in 15o cc of a mixture of 40 parts of 3% formaldehyde and 6o parts of water with initial removal for a while, about an hour, and after being wound for 10 minutes at so to 60 ° C with 15o ccm of 2.5% milk of lime treated.
Nach gründlichem Spülen, Säuern und nochmaligem Spülen wird mit 3 Prozent Oxaminblau 3 B und io Prozent Glaubersalz calc. etwa i Stunde bei 7o bis 75° C ausgefärbt.After thorough rinsing, acidification and repeated rinsing, 3 Percent oxamine blue 3 B and 10 percent Glauber's salt calc. about an hour at 7o to 75 ° C colored.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB105609D DE389401C (en) | 1922-07-11 | 1922-07-11 | Process for increasing the receptivity of cellulose esters for dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB105609D DE389401C (en) | 1922-07-11 | 1922-07-11 | Process for increasing the receptivity of cellulose esters for dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE389401C true DE389401C (en) | 1924-01-31 |
Family
ID=6991377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB105609D Expired DE389401C (en) | 1922-07-11 | 1922-07-11 | Process for increasing the receptivity of cellulose esters for dyes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE389401C (en) |
-
1922
- 1922-07-11 DE DEB105609D patent/DE389401C/en not_active Expired
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