US3687603A - Simultaneous dyeing of wool and cotton fibrous material with condensation product of formaldehyde and mixture of sulfones and hydroxybenzenesulfonic acids - Google Patents
Simultaneous dyeing of wool and cotton fibrous material with condensation product of formaldehyde and mixture of sulfones and hydroxybenzenesulfonic acids Download PDFInfo
- Publication number
- US3687603A US3687603A US773326A US3687603DA US3687603A US 3687603 A US3687603 A US 3687603A US 773326 A US773326 A US 773326A US 3687603D A US3687603D A US 3687603DA US 3687603 A US3687603 A US 3687603A
- Authority
- US
- United States
- Prior art keywords
- wool
- formaldehyde
- mixture
- fibrous material
- dyeing
- 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
- 210000002268 wool Anatomy 0.000 title abstract description 31
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title abstract description 21
- 238000004043 dyeing Methods 0.000 title abstract description 18
- 239000007859 condensation product Substances 0.000 title abstract description 14
- 239000000203 mixture Substances 0.000 title abstract description 11
- 239000002657 fibrous material Substances 0.000 title abstract description 9
- 150000003457 sulfones Chemical class 0.000 title abstract description 6
- 229920000742 Cotton Polymers 0.000 title description 11
- IULJSGIJJZZUMF-UHFFFAOYSA-N 2-hydroxybenzenesulfonic acid Chemical class OC1=CC=CC=C1S(O)(=O)=O IULJSGIJJZZUMF-UHFFFAOYSA-N 0.000 title description 2
- 239000002253 acid Substances 0.000 abstract description 18
- 238000000034 method Methods 0.000 abstract description 17
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 abstract description 14
- 239000000975 dye Substances 0.000 abstract description 13
- 239000003795 chemical substances by application Substances 0.000 abstract description 10
- 150000007513 acids Chemical class 0.000 abstract description 8
- 239000000835 fiber Substances 0.000 abstract description 8
- 239000004312 hexamethylene tetramine Substances 0.000 abstract description 7
- 235000010299 hexamethylene tetramine Nutrition 0.000 abstract description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical group OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 4
- 230000008021 deposition Effects 0.000 abstract description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 125000001174 sulfone group Chemical group 0.000 description 6
- 229920000297 Rayon Polymers 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- -1 monocyclic hydroxybenzenesulfonic acids Chemical class 0.000 description 4
- 239000002964 rayon Substances 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 239000000987 azo dye Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 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 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- YCOXCINCKKAZMJ-UHFFFAOYSA-N 4-hydroxy-3-methylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=CC=C1O YCOXCINCKKAZMJ-UHFFFAOYSA-N 0.000 description 1
- FEPBITJSIHRMRT-UHFFFAOYSA-N 4-hydroxybenzenesulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1 FEPBITJSIHRMRT-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- MVIOINXPSFUJEN-UHFFFAOYSA-N benzenesulfonic acid;hydrate Chemical compound O.OS(=O)(=O)C1=CC=CC=C1 MVIOINXPSFUJEN-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- 150000003739 xylenols Chemical class 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
- 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
- D06P1/52—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 synthetic macromolecular substances
- D06P1/56—Condensation products or precondensation products prepared with aldehydes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- 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
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
- D06P3/8219—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and amide 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
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/12—Reserving parts of the material before dyeing or printing ; Locally decreasing dye affinity by chemical means
-
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/14—Wool
-
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/14—Wool
- D06P3/16—Wool using acid dyes
-
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/14—Wool
- D06P3/20—Wool using mordant dyes using metallisable dyes
-
- 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
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/62—Natural or regenerated cellulose using direct dyes
-
- 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
- Y10S8/916—Natural fiber dyeing
- Y10S8/917—Wool or silk
-
- 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
- Y10S8/916—Natural fiber dyeing
- Y10S8/918—Cellulose textile
Definitions
- wool can be advantageously dyed with wool dyes and cellulosic fibres with substantive cotton dyes in one and the same bath, when dyeing is performed in baths that contain in addition to the dyestuffs fibreafiinic wool resisting agents and hexamethylenetetramine and which are of acid reaction at least at the start of the dyeing operation.
- the wool resisting agent in the bath is a condensation product of formaldehyde and a mixture of (a) a sulphone containing two monocyclic benzene residues bound to the SO groups and further substituted by hydroxyl groups and (b) a monocyclic hydroxybenzenesulphonic acid.
- wool is dyed simultaneously with cellulosic fibrous material.
- Suitable cellulosic fibrous materials are regenerated cellulose, such as rayon or spun rayon, as well as native cellulose such as linen or especially cotton. These fibrous materials may be in different stages of their processing, for example loose or mixed yarns or in form of fabrics. They may be present in intimate mixtures, for example in mixed weaves, or the individual types of fibre may form large fibre combinations; this is the case, for example, in fabrics in which warp and weft consist of different types of material, or in carpets in which the pile and the backing are made from different materials. So-called half-wool is specially preferred; it consists of wool and cotton, and this mixture may be intimate or brought about only during the doubling or weaving operation.
- the wool share is dyed with wool dyes which may belong to a variety of types, especially to the group of acid azo dyes or of the acid anthraquinone dyestufis.
- the monoazo dyes are specially suitable.
- Advantageous results have been obtained with chromium or cobalt complexes of monoazo dyes that contain more than ice one molecule of dyestnff for every atom of metal bound in complex union, and in which at least one dyestuif molecule is free from sulphonic acid groups and from carboxyl groups not participating in the complex formation.
- the heavy metal atom may be bound with two different or two identical dyestuif molecules.
- the complexforming group of the dyestuffs may be, for example, an orthcrhydroxy-ortho'-aminoazo grouping, an ortho-hydroxy-ortho'-carboxyazo grouping or preferably an ortho, ortho-dihydroxyazo grouping.
- an orthcrhydroxy-ortho'-aminoazo grouping an ortho-hydroxy-ortho'-carboxyazo grouping or preferably an ortho, ortho-dihydroxyazo grouping.
- the cellulose fibres are dyed with substantive cotton dyestuffs which advantageously have as such little affinity for the wool fibre. Otherwise, these dyestuffs may belong to a variety of types.
- azo dyes especially disazo and polyazo dyes, which may contain metal bound in complex union, preferably copper, or azoxy dyestuffs or sulphonated copper phthalocyanines.
- the condensation products to be used in the present process are prepared from mixtures of sulphones and sulphonic acids of the kind referred to above.
- mixtures are used in which the molecular ratio of (a) sulphone to (b) sulphonic acid is from 40:60 to :15.
- Both the sulphones and sulphonic acids suitable as relevant starting materials are known. From among the sulphones the dihydroxydiphenylsulphones of the formula Ha l- 0.
- R and R independently of each other, represent hydrogen atoms or methyl or sulphonic acid groups.
- R and R independently of each other, represent hydrogen atoms or methyl or sulphonic acid groups.
- Suitable monocyclic hydroxybenzenesulphonic acids are, for example, phenolsulphonic acid such as 1-hydroxybenzene-4-sulphonic acid and cresolsulphonic acids sozn drox'ybenzene, such as phenol, p-cresol or a xylenol, with Manufacturing instruction concentrated sulphuric acid; then water is added and the alkaline reaction is adjusted by addition of the requisite A miXtl-lffi f 317 gof Y Y- ll p .quantity of alkali metal hydroxide, and without intery p and 150-5 E- y yy mediate separation the condensation with formaldehyde 5 slllphonic acid in 100 f Wat is endered alkaline i f d, with 463 g. of 30% aqueous sodium hydroxide solution.
- the necessary acid reac- P 'f" 9 is reacted with form tion is advantageously adjusted by the addition of acetic aldehyde m the Indicated manner acid to the dyebath. Since hexamethylenetetramine con- Example tinuously gives off ammonia during dyeing, the pH value of the dyebath, and incidentally also of the wool, rises in course of time. However, with the quantities of acetic acid conventionally used in dyeing from acid baths it is quite possible to conduct the dyeing process so that even when dyeing takes a relatively long time the pH value never rises substantially above 7 so that it is possible to positively prevent any damage to the wool fibre caused by excess alkalinity.
- condensation products prevent the substantive cotton dyestuffs from depositing on the wool.
- dyeing half-wool it is endeavoured to achieve as even a tinctorial strength as possible for the two fibres; this is considerably facilitated in dyeing by the present process since the two fibres are (1) OH G A preparation is manufactured by mixing 1 part of the condensation product A with 2 parts of hexamethylenetetrarnine.
- half-wool warp: viscose spun rayon; weft: pure wool boucle yarn
- warp viscose spun rayon
- weft pure wool boucle yarn
- the present process has the advantage that, even when relatively small quantities of a readily accessible agent (b) dyestufl of the formula H033 C Ha 1103s NH Ho OCH:
- the above- (b), the wool dyes shown in column I in combination with mentioned quantities of these substances may be admixed the appropriate substantive dyestuffs in column II of the to form stable preparations ready for use and suitable for following table may be used in the indicated manner for the performance of the present process.
- the two constituents of the preparation may Instruction and in the example are by weight. be added at the same ratio singly to the dyebath.
- sulfones (a) are of the formula in which R; and R independently of each other, represent a member selected from the group consisting of hydrogen atoms, methyl and sulfonic acid groups.
- condensation products of the indicated kind contain (a) 4,4- dihydroxy 3 methyl-diphenylsulfonic-(1,1) and (b) 1-hydroxy-2-methylbenzene-4-sulfonic acid.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1562367A CH481263A (de) | 1967-11-08 | 1967-11-08 | Verfahren zum gleichzeitigen Färben von Wolle und cellulosehaltigem Textilfasermaterial und zur Durchführung des Verfahrens geeignete Präparate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3687603A true US3687603A (en) | 1972-08-29 |
Family
ID=4410608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US773326A Expired - Lifetime US3687603A (en) | 1967-11-08 | 1968-11-04 | Simultaneous dyeing of wool and cotton fibrous material with condensation product of formaldehyde and mixture of sulfones and hydroxybenzenesulfonic acids |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3687603A (enExample) |
| BE (1) | BE723501A (enExample) |
| CH (1) | CH481263A (enExample) |
| ES (1) | ES359966A1 (enExample) |
| FR (1) | FR1591243A (enExample) |
| GB (1) | GB1226165A (enExample) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USB314489I5 (enExample) * | 1971-12-21 | 1975-01-28 | Ciba Geigy Ag | |
| US3870682A (en) * | 1970-10-29 | 1975-03-11 | Minnesota Mining & Mfg | Aldehyde condensation products of fluoraliphatic phenols |
| US3872056A (en) * | 1974-01-14 | 1975-03-18 | Ewald Daubach | Manufacture of phenol/formaldehyde resins |
| US3931083A (en) * | 1973-02-06 | 1976-01-06 | Showa Denko Kabushiki Kaisha | Water-reducing admixtures for ceramic pastes |
| US4218366A (en) * | 1974-02-21 | 1980-08-19 | Dainippon Pharmaceutical Co., Ltd. | Condensation product of 4,4'-dihydroxydiphenyl sulfone, 4,4'-dihydroxydiphenylsulfone sulfonic acid and a lower aldehyde and method of preparation |
| US4800118A (en) * | 1987-11-04 | 1989-01-24 | West Point Pepperell | Compositions and methods for imparting stain resistance to textile articles |
-
1967
- 1967-11-08 CH CH1562367A patent/CH481263A/de not_active IP Right Cessation
-
1968
- 1968-11-04 US US773326A patent/US3687603A/en not_active Expired - Lifetime
- 1968-11-04 FR FR1591243D patent/FR1591243A/fr not_active Expired
- 1968-11-06 GB GB1226165D patent/GB1226165A/en not_active Expired
- 1968-11-07 ES ES359966A patent/ES359966A1/es not_active Expired
- 1968-11-07 BE BE723501D patent/BE723501A/xx unknown
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3870682A (en) * | 1970-10-29 | 1975-03-11 | Minnesota Mining & Mfg | Aldehyde condensation products of fluoraliphatic phenols |
| USB314489I5 (enExample) * | 1971-12-21 | 1975-01-28 | Ciba Geigy Ag | |
| US3925016A (en) * | 1971-12-21 | 1975-12-09 | Ciba Geigy Ag | Polyarcrylonitrile basic dyeing process with anionic assistant |
| US3931083A (en) * | 1973-02-06 | 1976-01-06 | Showa Denko Kabushiki Kaisha | Water-reducing admixtures for ceramic pastes |
| US3872056A (en) * | 1974-01-14 | 1975-03-18 | Ewald Daubach | Manufacture of phenol/formaldehyde resins |
| US4218366A (en) * | 1974-02-21 | 1980-08-19 | Dainippon Pharmaceutical Co., Ltd. | Condensation product of 4,4'-dihydroxydiphenyl sulfone, 4,4'-dihydroxydiphenylsulfone sulfonic acid and a lower aldehyde and method of preparation |
| US4800118A (en) * | 1987-11-04 | 1989-01-24 | West Point Pepperell | Compositions and methods for imparting stain resistance to textile articles |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1805793B2 (de) | 1976-09-09 |
| FR1591243A (enExample) | 1970-04-27 |
| ES359966A1 (es) | 1970-06-16 |
| CH481263A (de) | 1969-12-31 |
| DE1805793A1 (de) | 1969-06-26 |
| BE723501A (enExample) | 1969-05-07 |
| CH1562367A4 (enExample) | 1969-05-30 |
| GB1226165A (enExample) | 1971-03-24 |
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