US3206274A - Processing of cellulose triacetate - Google Patents
Processing of cellulose triacetate Download PDFInfo
- Publication number
- US3206274A US3206274A US828937A US82893759A US3206274A US 3206274 A US3206274 A US 3206274A US 828937 A US828937 A US 828937A US 82893759 A US82893759 A US 82893759A US 3206274 A US3206274 A US 3206274A
- Authority
- US
- United States
- Prior art keywords
- cellulose
- weight
- treatment
- filamentary material
- aqueous solution
- 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
- 229920002284 Cellulose triacetate Polymers 0.000 title description 3
- 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 title description 3
- 239000000463 material Substances 0.000 claims description 21
- 229920002678 cellulose Polymers 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 239000001913 cellulose Substances 0.000 claims description 9
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 7
- -1 HYDROXYL GROUP Chemical group 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 claims description 6
- 238000010409 ironing Methods 0.000 claims description 4
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 claims description 4
- 239000004744 fabric Substances 0.000 description 13
- 238000004043 dyeing Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OVOUKWFJRHALDD-UHFFFAOYSA-N 2-[2-(2-acetyloxyethoxy)ethoxy]ethyl acetate Chemical compound CC(=O)OCCOCCOCCOC(C)=O OVOUKWFJRHALDD-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- QRYRORQUOLYVBU-VBKZILBWSA-N carnosic acid Chemical compound CC([C@@H]1CC2)(C)CCC[C@]1(C(O)=O)C1=C2C=C(C(C)C)C(O)=C1O QRYRORQUOLYVBU-VBKZILBWSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- LFEINUNSYODISY-UHFFFAOYSA-N (ent-5alpha,6beta)-15,16-Epoxy-3,13(16),14-clerodatrien-18,6-olide Natural products CC1CC(C23C)OC(=O)C3=CCCC2C1(C)CCC=1C=COC=1 LFEINUNSYODISY-UHFFFAOYSA-N 0.000 description 2
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 2
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VOCYGZAHYQXJOF-UHFFFAOYSA-N 1,8-dihydroxy-4-[4-(2-hydroxyethyl)anilino]-5-nitroanthracene-9,10-dione Chemical compound C1=CC(CCO)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=C([N+]([O-])=O)C=CC(O)=C1C2=O VOCYGZAHYQXJOF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- UGZICOVULPINFH-UHFFFAOYSA-N acetic acid;butanoic acid Chemical class CC(O)=O.CCCC(O)=O UGZICOVULPINFH-UHFFFAOYSA-N 0.000 description 1
- AVMNFQHJOOYCAP-UHFFFAOYSA-N acetic acid;propanoic acid Chemical class CC(O)=O.CCC(O)=O AVMNFQHJOOYCAP-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 239000004434 industrial solvent Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
-
- 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
- D06P3/42—Cellulose acetate using dispersed dyestuffs
-
- 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
- D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
-
- 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
- D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
- D06M13/232—Organic carbonates
-
- 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
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/6421—Compounds containing nitrile groups
-
- 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
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/651—Compounds without nitrogen
- D06P1/65106—Oxygen-containing compounds
- D06P1/65125—Compounds containing ester groups
-
- 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
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/667—Organo-phosphorus compounds
Definitions
- the present invention relates to novel processes for improving the properties of highly ester-ified cellulose filamentary materials such as cellulose :tniace-tate.
- filamentary materials of organic acid esters of cellulose having fewer than about 0.29 free hydroxyl groups per anhydroglucose unit are treated with hot dilute aqueous solutions of lower aliphatic acid esters of alkoxy lo-wer alkanols, al'k-oxy alkoxy-lower .allcanols or lower alkylene glycols, of triethyl phosphate, triethylene glycol diacetate, cyclic ethylene carbonate or lactonitrile.
- the solutions are subsequently Washed out and the filamentary materials dried.
- the treated materials dye more rapidly and evenly, have a (higher safe ironing temperature and are stronger after being subjected to heat treatment.
- Organic acid esters of cellulose which can be treated in accordance with the present invention include formates, propionates, bu-tyrates, acetate propionates, acetate butyrates, and the like although cellulose acetate, having an acetyl value of at least about 59% and preferably at least about 61% by weight calculated as acetic acid, is preferred.
- This material is hereinafter referred to as cellulose triacetate and the invention will be further described with reference to this preferred cellulose ester.
- the filamentary material may be in the form of fibers, tows, yarns, webs, fabrics, or the like, alone or blended with other fibers which are not damaged by the treatment.
- the lower fatty acid esters, lower alkyl ethers and lower alkoxy-lower alkyl ethers of hydroxy-lower .alkyl esters of lower fatty acids e.g. ethylene glycol di-acetate, B-ethoxyethyl acetate and butoxyethoxyethyl acetate give the best results from the points of view of degree of improvement, economy, ease and permissible latitude in treatment, rapidity and low useful concentrations.
- the concentration of treating agent may vary from as low as about 1 to 50%, by weight.
- the temperature of treatment may vary' from about 50 to 150 C.
- the time of treatment may last up to about 3 hours although it preferably is complete in about 1 hour or less, e.g. about 6 seconds at 150 C.
- the time and temperature vary inversely with each other and with concentration. It is an advantage of the invention that even if the concentration, time and temperature are all simultaneously at relatively high values the filamentary materials will not be damaged, ie, the process is not sensitive to variations within the broad ranges although in the interest of economy obviously it will be desired to employ the shortest possible :times and the lowest possible concentrations and temperatures.
- the concentration will vary with the temperature and time and with the identity of the treating agents.
- the preferred concentration is 1 to 25%; for ethylene glycol diacetate 2 to 16%; for ibutoxyethoxyethyl acetate 1 to 6%; for triethyl phosphate to 25%; for triethylene glycol diacetate 5 to 10%; for ethylene carbonate 1 to for lactonitrile 1 to 25%.
- the treatment may be effected by immersion of the filamentary material in the treating solution for the requisite time, by travel of the filamentary material through a treatment bath and then out of the bath with the distance and speed correlated to give the desired treatment time,
- the treatment may be effected simu' taneou-sly with the dyeing as by adding a dyestutf to the solution or it may .be effected subsequent to dyeing but preferably it is effected prior to dyeing and is followed by washing out of the treating solution prior to dyeing.
- This permits large amounts of the filamentary material to be treated in a single treatment apparatus, with obvious economies, even if portions of the filamentary materials are intended to be dyed different colors. Also the dilute treating solution recovered by washing is uncolored and can easily be concentrated and re-used.
- the filamentary material is given a heat treatment such as being contacted for about 10 to 60 seconds with hot air at about 200 to 235 C. in a tenter frame or a hot flue, by 3 to 30 seconds of contact with metal surfaces such as hot cans at about 200 to 235 C., or the like.
- the sequence is preferably pretreatment, followed by dyeing, followed by heat treatment.
- filamentary materials which have been pretreated in accordance with the present invention are stronger than materials identical except for omission of the pretreatment, whether or not dyeing has taken place.
- Example I (a) A portion of fabric woven of cellulose acetate staple fiber yarn having an .acetyl value of 61.5% calculated as acetic acid is immersed in 55 times its weight of a 5% solution of fi-ethoxyethyl acetate .at C. and after 300 seconds is rinsed in hot water, rinsed in cold water and dried. 1
- Example 11 The fabric of Example I can be pretreated by immersion in 55 times its weight of a 10% aqueous solution of triethyl phosphate for 300 seconds at about 95 C. After rinsing with water and drying, the fabric can be heat treated as in Example I. If desired, the fabric can be dyed prior to heat treatment.
- Example III Repeating Example II with the substitution of a 10% aqueous solution of triethylene glycol diacetate for the triethyl phosphate produces approximately the same improvements.
- Example IV The process of Example II is repeated except for use of a 10% aqueous solution of ethylene carbonate for the pretreatment.
- Example V A 10% aqueous solution of lactonitrile can be used as the pretre-at ing agent in the process of Example II.
- the process which comprises immersing a filamentary material comprising a lower alkanoic acid ester of cellulose having fewer than about 0.29 free hydroxyl group per .anhydrogl'ucose unit .in an aqueous solution of about 1 to 15% by weight concentration of ethylene carbo-nate for a duration ranging from a time at least suflicient to increase the safe-ironing temperature up to about 1 hour at about 50 to 150 C., the ethylene carbonate being present in about 1 to 50% of the weight of the cellulose ester.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE635262D BE635262A (en, 2012) | 1959-07-23 | ||
US828937A US3206274A (en) | 1959-07-23 | 1959-07-23 | Processing of cellulose triacetate |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US828937A US3206274A (en) | 1959-07-23 | 1959-07-23 | Processing of cellulose triacetate |
Publications (1)
Publication Number | Publication Date |
---|---|
US3206274A true US3206274A (en) | 1965-09-14 |
Family
ID=25253122
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US828937A Expired - Lifetime US3206274A (en) | 1959-07-23 | 1959-07-23 | Processing of cellulose triacetate |
Country Status (2)
Country | Link |
---|---|
US (1) | US3206274A (en, 2012) |
BE (1) | BE635262A (en, 2012) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3513493A (en) * | 1965-08-11 | 1970-05-26 | Ugine Kuhlmann | Process for the coloring of materials based on cellulose acetate employing,as carrier,cyanoalkylation products |
Citations (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2202804A (en) * | 1937-08-14 | 1940-05-28 | Commercial Solvents Corp | Cellulose acetate composition |
US2259515A (en) * | 1939-04-22 | 1941-10-21 | Celanese Corp | Dyeing cellulose derivative materials |
US2362182A (en) * | 1941-12-20 | 1944-11-07 | Bell Telephone Labor Inc | Manufacture of cellulose acetate solutions |
GB609945A (en) * | 1946-06-06 | 1948-10-08 | Thomas Vickerstaff | Dyeing of highly polymeric linear esters |
US2643175A (en) * | 1950-12-05 | 1953-06-23 | Celanese Corp | Treatment with alcoholic solution to complete coupling of azo dyes in cellulose acetate textile material |
US2646339A (en) * | 1950-12-27 | 1953-07-21 | Celanese Corp | Dyeing of cellulose derivative textile materials |
GB776346A (en) * | 1953-11-25 | 1957-06-05 | British Celanese | Improvements relating to the treatment of textile materials comprising fibres of cellulose triacetate |
US2824035A (en) * | 1954-01-12 | 1958-02-18 | British Celanese | Process of making stiffened composite fabrics |
GB795821A (en) * | 1955-05-10 | 1958-05-28 | British Celanese | Improvements in the finishing of cellulose ester textile fabrics |
US2901312A (en) * | 1955-05-07 | 1959-08-25 | British Rayon Res Ass | Process utilizing fluidized beds in the dyeing of fabrics, yarns and the like |
US2901311A (en) * | 1955-03-04 | 1959-08-25 | Hoechst Ag | Process for the printing of fibrous textile material made of polyester fibres |
US2923593A (en) * | 1955-07-05 | 1960-02-02 | British Celanese | Diethylene glycol diacetate as an assistant in the dyeing of cellulose triacetate |
US2954269A (en) * | 1957-02-20 | 1960-09-27 | Celanese Corp | Process for the production of patterned tone-on-tone effects on a thermoplastic material |
US2982597A (en) * | 1954-12-02 | 1961-05-02 | Celanese Corp | Textile treating |
US3069219A (en) * | 1955-07-08 | 1962-12-18 | British Celanese | Colouring cellulose triacetate textile materials |
US3132919A (en) * | 1956-03-29 | 1964-05-12 | British Celanese | Increasing safe ironing temperatures of cellulsoe triacetate fibers with swelling agents boiling above 190deg. c. |
-
0
- BE BE635262D patent/BE635262A/xx unknown
-
1959
- 1959-07-23 US US828937A patent/US3206274A/en not_active Expired - Lifetime
Patent Citations (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2202804A (en) * | 1937-08-14 | 1940-05-28 | Commercial Solvents Corp | Cellulose acetate composition |
US2259515A (en) * | 1939-04-22 | 1941-10-21 | Celanese Corp | Dyeing cellulose derivative materials |
US2362182A (en) * | 1941-12-20 | 1944-11-07 | Bell Telephone Labor Inc | Manufacture of cellulose acetate solutions |
GB609945A (en) * | 1946-06-06 | 1948-10-08 | Thomas Vickerstaff | Dyeing of highly polymeric linear esters |
US2643175A (en) * | 1950-12-05 | 1953-06-23 | Celanese Corp | Treatment with alcoholic solution to complete coupling of azo dyes in cellulose acetate textile material |
US2646339A (en) * | 1950-12-27 | 1953-07-21 | Celanese Corp | Dyeing of cellulose derivative textile materials |
GB776346A (en) * | 1953-11-25 | 1957-06-05 | British Celanese | Improvements relating to the treatment of textile materials comprising fibres of cellulose triacetate |
US2824035A (en) * | 1954-01-12 | 1958-02-18 | British Celanese | Process of making stiffened composite fabrics |
US2982597A (en) * | 1954-12-02 | 1961-05-02 | Celanese Corp | Textile treating |
US2901311A (en) * | 1955-03-04 | 1959-08-25 | Hoechst Ag | Process for the printing of fibrous textile material made of polyester fibres |
US2901312A (en) * | 1955-05-07 | 1959-08-25 | British Rayon Res Ass | Process utilizing fluidized beds in the dyeing of fabrics, yarns and the like |
GB795821A (en) * | 1955-05-10 | 1958-05-28 | British Celanese | Improvements in the finishing of cellulose ester textile fabrics |
US2923593A (en) * | 1955-07-05 | 1960-02-02 | British Celanese | Diethylene glycol diacetate as an assistant in the dyeing of cellulose triacetate |
US3069219A (en) * | 1955-07-08 | 1962-12-18 | British Celanese | Colouring cellulose triacetate textile materials |
US3132919A (en) * | 1956-03-29 | 1964-05-12 | British Celanese | Increasing safe ironing temperatures of cellulsoe triacetate fibers with swelling agents boiling above 190deg. c. |
US2954269A (en) * | 1957-02-20 | 1960-09-27 | Celanese Corp | Process for the production of patterned tone-on-tone effects on a thermoplastic material |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3513493A (en) * | 1965-08-11 | 1970-05-26 | Ugine Kuhlmann | Process for the coloring of materials based on cellulose acetate employing,as carrier,cyanoalkylation products |
Also Published As
Publication number | Publication date |
---|---|
BE635262A (en, 2012) |
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