US3416945A - Process for the optical brightening of fibers containing terephthalic acid polyesters - Google Patents
Process for the optical brightening of fibers containing terephthalic acid polyesters Download PDFInfo
- Publication number
- US3416945A US3416945A US45844865A US3416945A US 3416945 A US3416945 A US 3416945A US 45844865 A US45844865 A US 45844865A US 3416945 A US3416945 A US 3416945A
- Authority
- US
- United States
- Prior art keywords
- fabric
- brightening
- brightener
- formula
- terephthalic acid
- 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
- 238000000034 method Methods 0.000 title description 38
- 238000005282 brightening Methods 0.000 title description 34
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title description 28
- 239000000835 fiber Substances 0.000 title description 25
- 229920000728 polyester Polymers 0.000 title description 21
- 230000003287 optical effect Effects 0.000 title description 11
- 239000004744 fabric Substances 0.000 description 46
- 230000000694 effects Effects 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- -1 ethyleneoxy groups Chemical group 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 13
- 239000000203 mixture Substances 0.000 description 9
- 239000005020 polyethylene terephthalate Substances 0.000 description 9
- 229920000742 Cotton Polymers 0.000 description 8
- 229920004934 Dacron® Polymers 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 239000002202 Polyethylene glycol Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 229960000956 coumarin Drugs 0.000 description 7
- 239000002657 fibrous material Substances 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- 235000001671 coumarin Nutrition 0.000 description 5
- 238000009980 pad dyeing Methods 0.000 description 5
- 229920000151 polyglycol Polymers 0.000 description 5
- 239000010695 polyglycol Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000002562 thickening agent Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 description 2
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 2
- IJCLOOKYCQWSJA-UHFFFAOYSA-N 7-amino-3-phenylchromen-2-one Chemical class O=C1OC2=CC(N)=CC=C2C=C1C1=CC=CC=C1 IJCLOOKYCQWSJA-UHFFFAOYSA-N 0.000 description 2
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 2
- 229960002218 sodium chlorite Drugs 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- RWFZHFYWPYSEOZ-UHFFFAOYSA-N 1,2-diphenyl-N,N'-bis(triazin-4-yl)ethene-1,2-diamine Chemical compound N1=NN=C(C=C1)NC(=C(C1=CC=CC=C1)NC1=NN=NC=C1)C1=CC=CC=C1 RWFZHFYWPYSEOZ-UHFFFAOYSA-N 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- YTZPUTADNGREHA-UHFFFAOYSA-N 2h-benzo[e]benzotriazole Chemical class C1=CC2=CC=CC=C2C2=NNN=C21 YTZPUTADNGREHA-UHFFFAOYSA-N 0.000 description 1
- HWDSXZLYIKESML-UHFFFAOYSA-N 3-phenylchromen-2-one Chemical group O=C1OC=2C=CC=CC=2C=C1C1=CC=CC=C1 HWDSXZLYIKESML-UHFFFAOYSA-N 0.000 description 1
- 241001482107 Alosa sapidissima Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ABEOQSWLOAHSPF-UHFFFAOYSA-N O1C(=NC2=C1C=CC=C2)C=C/C=2OC1=C(N2)C=CC=C1 Chemical group O1C(=NC2=C1C=CC=C2)C=C/C=2OC1=C(N2)C=CC=C1 ABEOQSWLOAHSPF-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 235000017284 Pometia pinnata Nutrition 0.000 description 1
- 240000007653 Pometia tomentosa Species 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 229920004933 Terylene® Polymers 0.000 description 1
- 229920004935 Trevira® Polymers 0.000 description 1
- 241001584775 Tunga penetrans Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920013820 alkyl cellulose Polymers 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- DWHOIYXAMUMQTI-UHFFFAOYSA-L disodium;2-[(1-sulfonatonaphthalen-2-yl)methyl]naphthalene-1-sulfonate Chemical compound [Na+].[Na+].C1=CC2=CC=CC=C2C(S(=O)(=O)[O-])=C1CC1=CC=C(C=CC=C2)C2=C1S([O-])(=O)=O DWHOIYXAMUMQTI-UHFFFAOYSA-L 0.000 description 1
- FYIBGDKNYYMMAG-UHFFFAOYSA-N ethane-1,2-diol;terephthalic acid Chemical compound OCCO.OC(=O)C1=CC=C(C(O)=O)C=C1 FYIBGDKNYYMMAG-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- LCRMGUFGEDUSOG-UHFFFAOYSA-N naphthalen-1-ylsulfonyloxymethyl naphthalene-1-sulfonate;sodium Chemical compound [Na].C1=CC=C2C(S(=O)(OCOS(=O)(=O)C=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 LCRMGUFGEDUSOG-UHFFFAOYSA-N 0.000 description 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-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
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 230000002311 subsequent effect Effects 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
- D06L4/60—Optical bleaching or brightening
- D06L4/614—Optical bleaching or brightening in aqueous solvents
- D06L4/636—Optical bleaching or brightening in aqueous solvents with disperse brighteners
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
- D06L4/60—Optical bleaching or brightening
- D06L4/65—Optical bleaching or brightening with mixtures of optical brighteners
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2964—Artificial fiber or filament
- Y10T428/2967—Synthetic resin or polymer
- Y10T428/2969—Polyamide, polyimide or polyester
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2971—Impregnation
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2582—Coating or impregnation contains an optical bleach or brightener or functions as an optical bleach or brightener [e.g., it masks fabric yellowing, etc.]
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2861—Coated or impregnated synthetic organic fiber fabric
Definitions
- ABSTRACT OF THE DISCLOSURE 15 An improved pad dyeing process for the optical brightening of terephthalic acid polyster fibers is disclosed.
- the process comprises impregnating the fiber at room temperature with either 214'"-chlorinc-2"-cyanostilbyl-4" (naphtho-l',2':4,5) l,2.3-triazole alone or in a weight ratio of 1:5 to 2:1 with at least One other brightener compound which t'orms colorless blue fluorescent solutions and contains no stilbene groups and has at least one hetero atom fused with a benezene ring selected from coumarin, benzoxazole or naphthalic acid amides.
- the fiber is squeezed out and heated at preferably 180-220 C. to achieve a white to reddishwhite whiter-white effect.
- the present invention concerns a process for the optical brightening of fibers containing terephthalic acid polyesters as well as, as industrial product, the fiber materials brightened according to the invention.
- polyester fibers especially of the Dacron type with optical brightencrs of the oxazole and the like types by methods corresponding to those of the well-known pad-dyeing process, i.e, by impregnation of the goods on a pad mangle (foularding) at room temperature (about 15 to 40 C.), removal of an excess of the impregnating liquor and sub sequent drying and developing by exposure to a higher temperature, in the range of 140 to 220 C., for a short time, up to about one minute.
- the aqueous brightening dispersion to be used as pad liquor according to the invention contains about 0.5 to 6 g. per liter of finely distributed brightener of Formula I.
- the particle size of the brightener in the dispersion should be about 1 to 5;!- or even less.
- the fine degree of distribution of the brightener is attained by the usual methods, advantageously by milling with sand and in the presence of water and a dispersing agent, e.g., a condensation product of naphthalene sulfonic acid and formaldehyde.
- the amount of'the dispersing agent is about ,4, to 1/ calculated on the weight of the brightener used.
- the dispersion advantageously contains dispersing or emulsifying agents, e.g., fatty alcohol polyglycol ethers such as stearyl alcohol polyglycol ethers having 8 to 10 ethyleneoxy groups, or it contains protective colloids such as higher polymeric polyacrylates or polyacrylamides such as the commercial product Separan AP (sold by Dow Chemical) or Irgamin E (sold by Geigy, Basel, Switzerland), also thickeners such as alginates or cellulose derivatives, e.g. carboxyalkyl cellulose derivatives such as carboxymethyl cellulose or alkyl cellulose derivatives such as methyl cellulose.
- dispersing or emulsifying agents e.g., fatty alcohol polyglycol ethers such as stearyl alcohol polyglycol ethers having 8 to 10 ethyleneoxy groups
- protective colloids such as higher polymeric polyacrylates or polyacrylamides
- thickeners such as alginates or cellulose derivatives, e.g. carb
- fabrics which consist exclusively of polyesters are used as "fibers containing terephthalic acid polyesters," for example, fabrics made of poly-(1,2-ethyleneglycol)-terephthalic acid esters such as the commercial products Dacron (E. I. du Pont de Nemours, Wilmington, Del.), Terylene (Imperial Chemical Industries Ltd., London, England), Trevira (Farbwerke Hoechst A.G., Frankfurt am Main, Germany), Diolen (Ve occidentale Glanzstolf AG., Wuppertal, Germany) or Tergal (Rhodiaceta, Lyons, France), but also fabrics made of poly-(1,4-cyclohexyleneglycol)-terephthalic acid esters, e.g., the commercial product Kodel (Tennessee Eastman, Kingsport, Tenn.) are used.
- the polyterephthalic acid part is brightened. If it is desired to brighten the other component as well, then a brightening pad liquor is used which, in addition to the components mentioned above also contains an optical brightener suitable for the brightening of this component of the fabric. If the fabric is of the preferred mixture of polyterephthalate and cotton, then the cotton part is advantageously optically brightened with a brightener from the class of 4,4-bis-(triazinylamino)-stilbene disulfonic acids, e.g., with one of the brightener: described in U.S. Patent No. 2,473,475.
- the goods are impregnated with the brightening dispersion by the usual methods, advantageously on a pad mangle.
- the impregnated material is advantageously squeezed so that its remaining liquor content is from 40 3 to 100%, calculated on the dry weight of the material.
- the squeezed goods are then, optionally after an intermediate drying, heated to higher temperatures, advantageously with hot air at ISO-220 C.
- This mixture of brighteners according to the invention consists of the above-mentioned stilbene compound of Formula I and of at least one compound having affinity to polyesters, which compound forms colorless, blue-fluorescent solutions, contains no stilbene groups and contains at least one hetero ring fused with a benzene ring.
- the mixtures according to the invention cause a surprising, unexpected rise in the strength of the brightening effect.
- Suitable brighteners containing the coumarin ring are chiefly derivatives of 3-phenyl-7-aminocoumarin; of these the 3-phenyl coumarin compounds substituted in the 7- position by the 3-methyl-pyrazolyl-(l), the naphtho- (1',2':4,S)-triazolyl-(2) or the 4-chloro-6-diethylamino- 1,3,5-triazinyl-(2) radical are particularly suitable.
- Suitable compounds containing a benzoxazole ring are. e.g., the bis-benzoxazolyl-(2)-ethylenes and -2,5-thiophenes.
- naphthalic acid imides are 4- alkoxy-naphthalie acid-N-methyl-imide or 4-a'cetamino naphthalic acid-N-butyl-imide.
- the weight ratio of the brightener of Formula 1 to the other components as defined is advantageously from about 1:5 to 2:1, preferably up about 1:1.
- the particle size of the brightener should be about 1 to 5;. or even less.
- the necessary degree of distribution of the brightener is attained by the usual methods described hcreinbct'ore.
- the aqueous suspension of the active substances to be used as pad liquor in this aspect of the invention preferably contains 0.3 to 5 g. per liter of the brightening mixture and also, advantageously, emulsifying agents, such as the known commercial products- 4 Separan AP or Irgamin E. as well as thickeners, all mentioned in the foregoing.
- the goods are impregnated with the brightening suspension on a pad mangle and further treated in the manner described hereinbefore.
- Fibers containing polyesters of terephthalic acid brightcned according to the invention show a similar greatly improved white appearance in daylight and this white shade has similar good fastness to light as the brightened polyester materials obtained by the treatment described under the first aspect of this invention.
- Example 1 A white ethyleneglycol terephthalate polyester fabric (Dacron) is impregnated on a pad mangle at 25 C. with a ad liquor containing 2 g. of the brightening agent of Formula I in 1000 ml. of water. The fabric is squeezed to leave a liquor content of (calculated on the fiber dry weight) thereon given an intermediate drying at in a hot air stream, and then developed by pasing it for 30 seconds through a heat chamber at 210-220". The fabric so treated shows a very strong, brilliant white effeet.
- the pad liquor used is produced as follows: 30 parts of thcbrightener, with the addition of 2 parts of sodium methylene-bis-(naphthalene sulfonate) (commercially available under the trade name of Belloid TD) as dispersant, in parts of water are milled with sand until a particle size of at most 5; to smaller than 1;!- is attained. Water and parts of a thickenerconsisting of a stearyl alcohol polyglycol ether having about 9 ethyleneoxy groups are added to this 30% paste and the whole is diluted to 1000 parts so that a 10% paste is obtained. 20 parts of this 10% paste are then diluted with water to 1000 parts and the suspension obtained is used for the processing in the foulard described in the above example.
- Example 2 A blended fabric consisting of 67% polyethylene glycol terephthalate and 33% cotton, which has been previously bleached with hydrogen peroxide, is impregnated at 25 in a foulard with a suspension obtained analogously to Example 1 which contains 2 g. of the brightener of Formula I and 0.5 g. of the brightener of the formula 3, 1 in 1000 ml. of water. The fabric is squeezed to a liquor content of 60% calculated on the dry fabric weight, given an intermediate drying at 60 and then developed for 2% minutes at 180. The fabric thus treated shows a very strong, brilliant white effect in daylight.
- Example 4 An unbleached mixed fabric consisting of 65% polyethylene glycol terephthalate and 35% cotton is impregnated at 20 on a pad mangle with a suspension produced according to Example 1 containing 1.5 g. of the brightening agent of Formula I in 1000 ml. of water. The fabric is then wrung out to a liquor content of 50% based on the dry fabric weight and passed through a tentering frame which is so adjusted that the fabric is first pre-dried at 100' and is then heated for 30 seconds at 210'. The fabric thus treated is quite clearly brown colored and, as yet, has no visual white effect. It is then bleached on a covered jigger with an 85 hot aqueous solution which contains 3 m l.
- Example 6 A mixed fabric made of 67% polyethylene glycol terephthalate and 33% cotton which has been previously bleached with sodium chlorite, is padded at with a pad liquor obtained according to Example 5 which contains 1.2 g. of the brightener of Formula V and 0.8 g. of the brightener of Formula I, in 1000 ml. of water.
- the fabric is squeezed to a liquor content of about 60% 0f the dry fabric weight, given an intermediate drying at 60, and then developed for 2 minutes at 180.
- the resulting fabric has a beautiful, brilliant white effect in daylight, of very good fastness to light.
- Example 7 A mixed fabric made of 67% polyethylene glycol terephthalate and 33% cotton which has been previously bleached with sodium chlorite 'or hydrogen peroxide, is impregnated at 25' on a 'pa'd mangle with a liquor produced analogously to Example 5, but which contains 1.2 g. of the brightener of Formula V, 0.8 g. of the brightener in 1000 ml. of water. The fabric is then thoroughly rinsed, first with warm and then with cold water and afterwards dried at a temperature of 5fl-80. After this treatment both fibers in the mixed fabric show a strong, brilliant white effect.
- Example 5 A polyethyleneglycol terephthalate fabric (Dacron) is padded at '25 with a suspension containing 1.2 g. of
- the brightener of the formula ind 0.8 g. of the brightener of Formula I in 1000 ml. of .vater.
- the goods are squeezed to a liquor content of 50% on the dry fabric weight, given an intermediate drying at and then developed for 30 seconds at 2l0220.
- the fabric is given a strong, brilliant white effect which has very good fastness to light.
- the suspension used is produced as follows: 30 parts of the mixture of brighteners of the weight ratio given above and about 2 parts of sodium methylene bis-(naphthalene sulfonate) in 70 parts of water are milled with sand until a particle size of at most 5 microns to less than 1 micron is attained. To 330 parts of the 30%-paste Example 8 A Dacron fabric is impregnated on a pad mangle at 25' with a liquor produced analogously to Example 5 from 1.2 g. of the brightening agent of the formula CH: CH:
- the fabric is squeezed to a liquor content of 50% (calculated on the dry fabric weight). given an intermediate drying at 60 and then developed for 30 seconds at 210- 220.
- the resulting fabric shows a very strong, brilliant white effect in daylight, which has very good fastness to light.
- Example 9 A Dacron fabric is impregnated on a pad mangle at 25 with a liquor produced analogously to Example and 0.8 g. of the brightener of Formula I in l000'ml. of
- Example 10 A Dacron fabric is impregnated at on a pad mangle with a liquor produced analogously to Example 5 from L2 g. of the brightener of the formula and 0.8 g. of the brightener of Formula I, in 1000 ml. of water.
- the fabric is wrung out to leave a liquor content of 50% based on the dry fabric weight, pre-dried at and then developed for 30 seconds at 2l0-220 In daylight, the fabric so treated shows a strong, very lightstable, brilliant white effect.
- Example l 1 An unbleached blended fabric consisting of polyethylene glycol terephthalate and 35% cotton is impregnated at 20' on a pad mangle with a liquor produced according to Example 1 containing 1.2 g. of the brightener of Formula V and 0.8 g. of the brightener of Formula I in 1000 ml. of water.
- the fabric is wrung out to leave a liquor content of 50%., calculated on the dry weight of the'fabric, and then passed through a tentering frame which is so adiusted that the fabric is pre-dried at and is afterwards heated for 30 seconds at 210'.
- the fabric so treated is brown colored and has not yet any visual white effect. It is then bleached on a covered iigger with an aqueous solution, having a temperature of 85', which contains 3 ml. of 30%-hydrogen peroxide, 1 ml. of sodium silicate solution (38 136.), 0.25 g. of sodium hydroxide and 0.06 g. of the brightener of Formula IV in 1000 ml. of water.
- the fabric is then thoroughly rinsed, first with warm and then with cold water, and dried at a temperature of 50-80. After this treatment, both fibers of the blended fabric show a strong, brilliant white effect.
- the concentration of the exhaustion bath is the highest one usable with excessive "greening" occurring in the brightened fiber material.
- a fiber material containing terephthalic acid polyester fibers said fiber having been impregnated with from about 0.2 to 6 grams of the compound defined in claim 1 per kilogram of said fiber material and then having been heated at from 180 to 220' C.
- naphthalic acid imide compound is 4-alkoxy-naphthalic acid-N-methyl imide.
- naphthalic acid imide compound is 4-acetamino-naphthalic acid-N-butyl imide.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH706064A CH427722A (de) | 1964-05-29 | 1964-05-29 | Verfahren zum optischen Aufhellen von Polyester der Terephthalsäure enthaltendem Fasermaterial |
CH706164A CH424701A (de) | 1964-05-29 | 1964-05-29 | Verfahren zum optischen Aufhellen von polymere Ester der Terephthalsäure enthaltendem Fasermaterial |
Publications (1)
Publication Number | Publication Date |
---|---|
US3416945A true US3416945A (en) | 1968-12-17 |
Family
ID=25700664
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US45844865 Expired - Lifetime US3416945A (en) | 1964-05-29 | 1965-05-24 | Process for the optical brightening of fibers containing terephthalic acid polyesters |
US74711868 Expired - Lifetime US3467600A (en) | 1964-05-29 | 1968-07-24 | Combination optical brightener for terephthalic acid polyester fibers |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US74711868 Expired - Lifetime US3467600A (en) | 1964-05-29 | 1968-07-24 | Combination optical brightener for terephthalic acid polyester fibers |
Country Status (9)
Country | Link |
---|---|
US (2) | US3416945A (enrdf_load_stackoverflow) |
JP (1) | JPS5015903B1 (enrdf_load_stackoverflow) |
BE (2) | BE664606A (enrdf_load_stackoverflow) |
CH (2) | CH427722A (enrdf_load_stackoverflow) |
DE (2) | DE1519475B1 (enrdf_load_stackoverflow) |
FR (2) | FR1440255A (enrdf_load_stackoverflow) |
GB (2) | GB1052355A (enrdf_load_stackoverflow) |
NL (2) | NL6506796A (enrdf_load_stackoverflow) |
SE (2) | SE329589B (enrdf_load_stackoverflow) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3900608A (en) * | 1971-10-23 | 1975-08-19 | Bayer Ag | Preparations of optical brighteners |
US5187015A (en) * | 1989-02-17 | 1993-02-16 | Minnesota Mining And Manufacturing Company | Ice release composition, article and method |
US5646207A (en) * | 1994-03-14 | 1997-07-08 | Ppg Industries, Inc. | Aqueous sizing compositions for glass fibers providing improved whiteness in glass fiber reinforced plastics |
US8066140B1 (en) * | 2003-02-28 | 2011-11-29 | The Charles Machine Works, Inc. | Container door and container door latching and sealing system |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4055565A (en) * | 1969-12-30 | 1977-10-25 | Sumitomo Chemical Company, Limited | Optical brightening agents of naphthalimide derivatives |
US4622775A (en) * | 1982-11-30 | 1986-11-18 | Kraft, Inc. | Hydroponic plant collars |
EP0323399B1 (de) * | 1987-11-27 | 1993-02-17 | Ciba-Geigy Ag | Aufhellerdispersion |
DE3878540D1 (de) * | 1987-11-27 | 1993-03-25 | Ciba Geigy Ag | Aufhellerdispersion. |
CN111926559A (zh) * | 2020-08-18 | 2020-11-13 | 宁夏峰盛科技有限公司 | 一种三嗪基香豆素型荧光增白剂及其制备方法 |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2945033A (en) * | 1957-05-29 | 1960-07-12 | Geigy Ag J R | 7-triazinylamino-3-phenyl coumarins |
US2972611A (en) * | 1961-02-21 | Irrttnrpsrumttuiatotvt stttkvnf | ||
US3123617A (en) * | 1964-03-03 | Xnhxch | ||
US3127416A (en) * | 1960-09-26 | 1964-03-31 | Ciba Ltd | New chlorinated dicarboxylic acid dichloride and process for its manufacture |
US3147253A (en) * | 1961-06-17 | 1964-09-01 | Hodogaya Chemical Co Ltd | Process for manufacturing alpha, betadi-[aryloxazolyl-(2)]-ethylene |
US3181948A (en) * | 1958-06-02 | 1965-05-04 | Gevaert Photo Prod Nv | Method for optical bleaching of coated papers and resultant product |
US3288801A (en) * | 1962-06-07 | 1966-11-29 | Sandoz Ltd | Fluorescent 1, 2, 3-triazole derivatives of 3-phenyl-coumparin |
US3288786A (en) * | 1962-09-10 | 1966-11-29 | Gen Aniline & Film Corp | Naphthotriazole optical brighteners |
US3310564A (en) * | 1961-01-21 | 1967-03-21 | Kasai Toshiyasu | Novel 4-alkoxy naphthalimides |
US3330834A (en) * | 1967-07-11 | Naphthalimide whitening agents anb method of making same |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE560579A (fr) * | 1956-09-06 | 1960-04-22 | Geigy Ag J R | Composes triazolyl-stilbeniques fluorescents, leur preparation et leurs applications. |
DE1166197B (de) * | 1958-09-02 | 1964-03-26 | Ciba Geigy | Verfahren zur Herstellung von 2, 5-Di[benzoxazolyl-(2)]-thiophenderivaten |
US3366575A (en) * | 1964-03-13 | 1968-01-30 | Nippon Kayaku Kk | Enhancement of optical brightening effects by using two or more species of brightening agent |
-
1964
- 1964-05-29 CH CH706064A patent/CH427722A/de unknown
- 1964-05-29 CH CH706164A patent/CH424701A/de unknown
-
1965
- 1965-05-24 US US45844865 patent/US3416945A/en not_active Expired - Lifetime
- 1965-05-28 JP JP3114665A patent/JPS5015903B1/ja active Pending
- 1965-05-28 FR FR18658A patent/FR1440255A/fr not_active Expired
- 1965-05-28 NL NL6506796A patent/NL6506796A/xx unknown
- 1965-05-28 DE DE19651519475 patent/DE1519475B1/de active Pending
- 1965-05-28 BE BE664606D patent/BE664606A/xx unknown
- 1965-05-28 GB GB2278265A patent/GB1052355A/en not_active Expired
- 1965-05-28 SE SE701265A patent/SE329589B/xx unknown
- 1965-05-28 DE DE1519476A patent/DE1519476C3/de not_active Expired
- 1965-05-28 BE BE664605D patent/BE664605A/xx unknown
- 1965-05-28 GB GB2278165A patent/GB1051814A/en not_active Expired
- 1965-05-28 FR FR18657A patent/FR1440254A/fr not_active Expired
- 1965-05-28 SE SE701365A patent/SE328844B/xx unknown
- 1965-05-28 NL NL6506795A patent/NL6506795A/xx unknown
-
1968
- 1968-07-24 US US74711868 patent/US3467600A/en not_active Expired - Lifetime
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2972611A (en) * | 1961-02-21 | Irrttnrpsrumttuiatotvt stttkvnf | ||
US3123617A (en) * | 1964-03-03 | Xnhxch | ||
US3330834A (en) * | 1967-07-11 | Naphthalimide whitening agents anb method of making same | ||
US2945033A (en) * | 1957-05-29 | 1960-07-12 | Geigy Ag J R | 7-triazinylamino-3-phenyl coumarins |
US3181948A (en) * | 1958-06-02 | 1965-05-04 | Gevaert Photo Prod Nv | Method for optical bleaching of coated papers and resultant product |
US3127416A (en) * | 1960-09-26 | 1964-03-31 | Ciba Ltd | New chlorinated dicarboxylic acid dichloride and process for its manufacture |
US3310564A (en) * | 1961-01-21 | 1967-03-21 | Kasai Toshiyasu | Novel 4-alkoxy naphthalimides |
US3147253A (en) * | 1961-06-17 | 1964-09-01 | Hodogaya Chemical Co Ltd | Process for manufacturing alpha, betadi-[aryloxazolyl-(2)]-ethylene |
US3288801A (en) * | 1962-06-07 | 1966-11-29 | Sandoz Ltd | Fluorescent 1, 2, 3-triazole derivatives of 3-phenyl-coumparin |
US3288786A (en) * | 1962-09-10 | 1966-11-29 | Gen Aniline & Film Corp | Naphthotriazole optical brighteners |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3900608A (en) * | 1971-10-23 | 1975-08-19 | Bayer Ag | Preparations of optical brighteners |
US5187015A (en) * | 1989-02-17 | 1993-02-16 | Minnesota Mining And Manufacturing Company | Ice release composition, article and method |
US5646207A (en) * | 1994-03-14 | 1997-07-08 | Ppg Industries, Inc. | Aqueous sizing compositions for glass fibers providing improved whiteness in glass fiber reinforced plastics |
US6207737B1 (en) | 1994-03-14 | 2001-03-27 | Ppg Industries Ohio, Inc. | Glass fiber sizing, sized glass fibers and polyolefin reinforced articles |
US8066140B1 (en) * | 2003-02-28 | 2011-11-29 | The Charles Machine Works, Inc. | Container door and container door latching and sealing system |
Also Published As
Publication number | Publication date |
---|---|
NL6506796A (enrdf_load_stackoverflow) | 1965-11-30 |
US3467600A (en) | 1969-09-16 |
NL6506795A (enrdf_load_stackoverflow) | 1965-11-30 |
GB1052355A (enrdf_load_stackoverflow) | 1966-12-21 |
DE1519476C3 (de) | 1973-11-08 |
DE1519476B2 (de) | 1973-04-19 |
FR1440255A (fr) | 1966-05-27 |
DE1519476A1 (de) | 1970-12-23 |
FR1440254A (fr) | 1966-05-27 |
SE328844B (enrdf_load_stackoverflow) | 1970-09-28 |
CH427722A (de) | 1966-09-30 |
BE664606A (enrdf_load_stackoverflow) | 1965-11-29 |
CH424701A (de) | 1966-08-15 |
BE664605A (enrdf_load_stackoverflow) | 1965-11-29 |
JPS5015903B1 (enrdf_load_stackoverflow) | 1975-06-09 |
SE329589B (enrdf_load_stackoverflow) | 1970-10-19 |
DE1519475B1 (de) | 1970-05-14 |
GB1051814A (enrdf_load_stackoverflow) | 1966-12-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3400124A (en) | Optical brightening and new compositions of matter | |
US3416945A (en) | Process for the optical brightening of fibers containing terephthalic acid polyesters | |
US3900419A (en) | Benzofurans | |
US2956898A (en) | Certification of correction | |
DE60314746T2 (de) | Aufhellerpigmente | |
GB2174731A (en) | Extinguishing or preventing optical brightening | |
US3378389A (en) | 1, 3-diphenyl pyrazolines and method for brightening synthetic material therewith | |
US2773869A (en) | Alkenyl bisimidazole optical bleaching agents | |
US3595801A (en) | Aqueous dispersions of mixtures of benzoxazole derivatives and their use as optical brighteners | |
US4129412A (en) | Brightener mixtures and their use | |
US3135742A (en) | 1, 3-diaryl and 1, 3, 5-triaryl-pyrazoline derivatives | |
US3520814A (en) | Pyrazoline optical brighteners | |
JPH0116868B2 (enrdf_load_stackoverflow) | ||
US2424778A (en) | Composition for and method of whitening textiles with a blue fluorescent material and ultramarine | |
US2643197A (en) | Fluorescent alkoxy benzoyl derivatives of 4,4' diamino stilbene-2,2' disulfonic acidand detergent compositions containing same | |
US2528323A (en) | Method of treating textile mate | |
US3294570A (en) | Optical brightening of materials of synthetic polyesters and polyamides | |
US3242177A (en) | 7-(5-triazinyl-amino)-3-aryl-coumarin compounds | |
US2643198A (en) | Fluorescent compound and methods of imparting fluorescent effects to materials | |
US2661305A (en) | Method for improving the brightness of textile materials and product | |
JP4580241B2 (ja) | 蛍光増白剤の混合物 | |
US3366630A (en) | 2-(4'-amidostyryl)-benzoxazoles and method for using the same for the optical brightening of textiles | |
US3595604A (en) | Processes for whitening and retarding sunlight yellowing of protein fibers by treatment with a fluorescent brightening agent,thiourea,and a source of formaldehyde | |
US3708475A (en) | Process for the production of chlorine-containing v-triazole compounds | |
JPH02300147A (ja) | 新規な4―スチリルビフエニルアルデヒドとその製造法 |