US3802841A - Nitro aromatic hydrocarbon,amino nitro aromatic & nitro aromatic phosphine oxides on aromatic polyamide-imide as light fading inhibitors for dyes thereon - Google Patents
Nitro aromatic hydrocarbon,amino nitro aromatic & nitro aromatic phosphine oxides on aromatic polyamide-imide as light fading inhibitors for dyes thereon Download PDFInfo
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- US3802841A US3802841A US00262441A US26244172A US3802841A US 3802841 A US3802841 A US 3802841A US 00262441 A US00262441 A US 00262441A US 26244172 A US26244172 A US 26244172A US 3802841 A US3802841 A US 3802841A
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- United States
- Prior art keywords
- nitro aromatic
- nitro
- aromatic
- textile article
- textile
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- Expired - Lifetime
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- -1 Nitro aromatic hydrocarbon Chemical class 0.000 title claims abstract description 156
- 239000004962 Polyamide-imide Substances 0.000 title claims abstract description 23
- 229920002312 polyamide-imide Polymers 0.000 title claims abstract description 23
- 125000003118 aryl group Chemical group 0.000 title claims description 34
- 239000000975 dye Substances 0.000 title description 32
- 238000005562 fading Methods 0.000 title description 3
- 239000003112 inhibitor Substances 0.000 title description 3
- 239000004753 textile Substances 0.000 claims abstract description 86
- 238000000034 method Methods 0.000 claims abstract description 61
- 238000004043 dyeing Methods 0.000 claims abstract description 50
- 238000007639 printing Methods 0.000 claims abstract description 40
- 229920000642 polymer Polymers 0.000 claims abstract description 25
- 239000004760 aramid Substances 0.000 claims abstract description 23
- 229920003235 aromatic polyamide Polymers 0.000 claims abstract description 23
- 229920001059 synthetic polymer Polymers 0.000 claims description 27
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 11
- RJKGJBPXVHTNJL-UHFFFAOYSA-N 1-nitronaphthalene Chemical compound C1=CC=C2C([N+](=O)[O-])=CC=CC2=C1 RJKGJBPXVHTNJL-UHFFFAOYSA-N 0.000 claims description 3
- DSBIJCMXAIKKKI-UHFFFAOYSA-N 5-nitro-o-toluidine Chemical group CC1=CC=C([N+]([O-])=O)C=C1N DSBIJCMXAIKKKI-UHFFFAOYSA-N 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 abstract description 17
- 239000004744 fabric Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- 125000000217 alkyl group Chemical group 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 15
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 14
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 14
- 125000003545 alkoxy group Chemical group 0.000 description 13
- 150000001805 chlorine compounds Chemical class 0.000 description 11
- 150000004985 diamines Chemical class 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 239000000981 basic dye Substances 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 229910052736 halogen Inorganic materials 0.000 description 10
- 150000002367 halogens Chemical class 0.000 description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 7
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
- 238000004040 coloring Methods 0.000 description 5
- 238000005108 dry cleaning Methods 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 150000004984 aromatic diamines Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000875 corresponding effect Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000013589 supplement Substances 0.000 description 3
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical class ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 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 2
- 125000003963 dichloro group Chemical group Cl* 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- LHRXTFDXJQAGAV-UHFFFAOYSA-L disodium 3-hydroxy-4-(naphthalen-1-yldiazenyl)naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].Oc1c(cc2cc(ccc2c1N=Nc1cccc2ccccc12)S([O-])(=O)=O)S([O-])(=O)=O LHRXTFDXJQAGAV-UHFFFAOYSA-L 0.000 description 2
- 244000144992 flock Species 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 229920002480 polybenzimidazole Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 150000003628 tricarboxylic acids Chemical class 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 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 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical class NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- MCRYBELDVGNCFW-UHFFFAOYSA-N 2,4-dimethyl-3-nitroaniline Chemical compound CC1=CC=C(N)C(C)=C1[N+]([O-])=O MCRYBELDVGNCFW-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical group CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- LIPNWLFZHQUBEA-UHFFFAOYSA-N 2-ethylbenzene-1,3-dicarbonyl chloride Chemical compound C(C)C1=C(C(=O)Cl)C=CC=C1C(=O)Cl LIPNWLFZHQUBEA-UHFFFAOYSA-N 0.000 description 1
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 1
- IBMNARSXHOVILE-UHFFFAOYSA-N 4,6-diethoxybenzene-1,3-dicarbonyl chloride Chemical class C(C)OC1=CC(=C(C=C1C(=O)Cl)C(=O)Cl)OCC IBMNARSXHOVILE-UHFFFAOYSA-N 0.000 description 1
- OSUWBBMPVXVSOA-UHFFFAOYSA-N 4-(4-carbonochloridoylphenoxy)benzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1OC1=CC=C(C(Cl)=O)C=C1 OSUWBBMPVXVSOA-UHFFFAOYSA-N 0.000 description 1
- QDBOAKPEXMMQFO-UHFFFAOYSA-N 4-(4-carbonochloridoylphenyl)benzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=C(C(Cl)=O)C=C1 QDBOAKPEXMMQFO-UHFFFAOYSA-N 0.000 description 1
- IJEULPFTGXDFEV-UHFFFAOYSA-N 4-ethoxy-2-methoxybenzene-1,3-dicarbonyl chloride Chemical compound COC1=C(C(=O)Cl)C=CC(=C1C(=O)Cl)OCC IJEULPFTGXDFEV-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PJBFAFQWOGGBQB-UHFFFAOYSA-N CCC1=C(CC)C(C(Cl)=O)=C(CC)C(C(Cl)=O)=C1CC Chemical class CCC1=C(CC)C(C(Cl)=O)=C(CC)C(C(Cl)=O)=C1CC PJBFAFQWOGGBQB-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241001522296 Erithacus rubecula Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- LNWBFIVSTXCJJG-UHFFFAOYSA-N [diisocyanato(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(N=C=O)(N=C=O)C1=CC=CC=C1 LNWBFIVSTXCJJG-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002222 fluorine compounds 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
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 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
- D06P1/64—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
- D06P1/6422—Compounds containing nitro or nitroso groups
-
- 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
- D06M13/322—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 nitrogen
- D06M13/392—Nitroso compounds; Nitro compounds
-
- 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
- D06P3/24—Polyamides; Polyurethanes
-
- 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
- D06P3/24—Polyamides; Polyurethanes
- D06P3/242—Polyamides; Polyurethanes using basic 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
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/924—Polyamide fiber
Definitions
- ABSTRACT An improved process of dyeing or printing textile articles composed of thermostable polymers, i.e. aromatic polyamides and polyamide imides, and the textile articles so dyed or printed, wherein the dyeing or printing solution contacting the textile article contains as an adjuvant, in an amount sufficient to provide improved light fastness to the textile article, an ultraviolet light absorbing nitro aromatic compound.
- the nitro aromatic compound is preferably selected from nitro aromatic hydrocarbons, nitro aromatic amines and nitro aromatic phosphine oxides.
- the present invention is directed to a novel improved process for dyeing or printing textile articles having a base of a thermostable synthetic polymer as well as the novel dyed or printed textile article itself. More specifically, the present invention is directed to such novel process and product wherein in the dyeing or printing of a textile article having a base of a thermostable synthetic polymer, improved light resistance is created by utilization as an adjuvant an ultraviolet light absorbing nitro aromatic compound.
- thermostable polymer Prior to the development of the present invention, it has been known that textile articles having a base of a thermostable polymer can be dyed with plastosoluble dyes. While such dyeing can be carried out utilizing plastosoluble dyes, this method is not totally satisfactory, particularly for dark colors. This is due to the fact that the plastosoluble dyes do not appreciably fix on the thermostable materials, even after addition of a carrier to the dye bath, the carrier generally improving the fixing of the plastosoluble dye. Still further, the shade which is obtained on the thermostable polymer textile article utilizing the plastosoluble dye is not sufficiently light fast.
- thermostable polymer acid sites so as to provide the fibers produced an affinity for basic dyes. While this procedure effectively allowed the dyeing of the fibers produced from the thermostable polymers to be dyed with basic dyes due to the affinity for the acid sites, it was unfortunately found that the dyeings or printings obtained had poor light fastness. Here again, this is an industrial or commercial drawback to this dyeing procedure.
- thermostable synthetic polymer having a base of thermostable polymer
- the textile articles having a base of the thermostable polymer are dyed or printed with a dyeing or printing solution or bath containing as an adjuvant at least one ultraviolet light absorbing nitro aromatic compound in an amount sufficient to provide improved light fastness to the textile article.
- the nitro aromatic derivatives having the ability to absorb ultraviolet rays are selected from nitro aromatic hydrocarbons, nitro aromatic amines and nitro aromatic phosphine oxides.
- thermostable synthetic 2 polymers are further object of the present invention to provide a novel improved process for dyeing or printing textile articles composed of thermostable synthetic 2 polymers, wherein the improvement resides in dyeing or printing such textile article utilizing as an adjuvant in the dyeing or printing solution at least one ultraviolet light absorbing nitro aromatic compound.
- a still further object of the present invention comprises such improved process for dyeing or printing textile articles having a thermostable synthetic polymer base, wherein at least one ultraviolet light absorbing nitro aromatic compound selected from nitro aromatic hydrocarbons, nitro aromatic amines and nitro aromatic phosphine oxides is employed as an adjuvant in an amount sufficient to provide light fastness.
- a still further object of the present invention is to provide such a process for the production of textile articles dyed or printed and having improved light fastness, the textile articles containing 1 to 5 percent by weight of a nitro aromatic compound having the ability to absorb ultraviolet light.
- a dyeing or printing process wherein a textile article composed of a thermostable synthetic polymer is dyed or printed with a dyeing or printing solution containing as an adjuvant, in an amount sufficient to provide improved light fastness to the textile article, an ultraviolet light absorbing nitro aromatic compound,
- the nitro aromatic compound having the ultraviolet light absorbing property is selected from nitro aromatic hydrocarbons, nitro aromatic amines and nitro aromatic phosphine oxides.
- the term textile article that can be effectively dyed or printed embraces not only textile fabrics but other articles in the form of yarns, flocks, knits, unwoven materials and the like. Accordingly, the textile article to be effectively dyed or printed in the process of the present invention can take any conventional form.
- thermostable synthetic polymer is meant to embrace those synthetic polymers which have a high heat resistance, i.e. a heat resistance in the order of 350 to 500C. While such thermostable synthetic polymers can take various forms, the polymers most suited in carrying out the process of the present invention are of the aromatic polyamide type or polyamide-imide type.
- aromatic polyamides which are advantageously dyed or printed in accordance with the process of the present invention are well known thermally stable synthetic polymers which are conventionally prepared in the form of textile fibers, filaments and yarns in the 1 production of textile articles.
- the aromatic polyamides are characterized predominantly by the recurring structural unit which do not form a polyamide during polymerization, the term lower referring to less than five carbon atoms.
- Aromatic polyamides are well known in the art and they and their preparation are described, for example, in Hill, Kwolek and Sweeny, U.S. Pat. No. 3,094,51 1, the entire disclosure of which is hereby incorporated by reference. The description of Hill et al., column l, line 48, to column 5, line 20, is particularly incorporated.
- Aromatic polyamides may be obtained by reacting a diisocyanate or a diacid such as described in US. Pat. No. 3,642,715.
- the aromatic polyamides are also reaction products of an aromatic diacid chloride with an aromatic diamine, the aromatic diacid chloride being of the formula wherein Ar, is a divalent aromatic radical, i.e. it contains resonant'unsaturation, and Hal is a halogen atom from the class consisting of chlorine, bromine, and fluorine.
- the aromatic radical may have a single, multiple, or fused ring structure.
- One or more hydrogens of the aromatic nucleus may be replaced by non-polyamideforming groups such as lower alkyl, lower alkoxy, halogen, nitro, sulfonyl, lower carbalkoxy, and the like.
- the terms lower alkyl and lower alkoxy" and lower carbalkoxy refers to groups containing less than five carbon atoms.
- Diacid chlorides which may be utilized to prepare the polyamides include isophthaloyl chloride and lower alkyl isophthaloyl chlorides, such as methyl-, ethyl-, propyl-, etc., isophthaloyl chlorides. There may be more than one alkyl group attached to the aromatic ring as in the case of dimethyl, trimethyl, tetramethyl, diethyl, triethyl, and tetraethyl isophthaloyl chlorides.
- alkyl substituent groups be the same because compounds such as 2- 'methyl-4 ethyl isophthaloyl chloride and 2-methyl-4- ethyl-S-propyl isophthaloyl chloride may be utilized,
- the total number of carbon atoms in all the substituentgroups (non-polyamide-forming groups) attached to the aromatic ring in the latter two compounds being three and six, respectively.
- the aromatic ring in isophthaloyl chloride may be substituted with one or more lower alkoxy groups such as, for example, methoxy-, ethoxy-, propoxy-, butoxy-, etc., isophthaloyl chlorides.
- alkyl-substituted isophthaloyl chlorides it is desirable that the total number of carbon atoms in the alkoxy groups attached to the aromatic ring be less than about five, but it is not necessary that all of the alkoxy groups be the same.
- vdimethoxy-, trimethoxy, tetramethoxy-, and diethoxy-isophthaloyl chlorides and 2-methoxy-4-ethoxy isophthaloyl chloride.
- Halogen-substituted isophthaloyl chlorides as examplified by chloro-, bromo-, and fluoroisophthaloyl chlorides may be used. More than one halogen may be attached to the aromatic ring and dihalo isophthaloyl chlorides.
- halogens in these compounds may be the same or different as in the case of the dihalo compounds.
- isophthaloyl chlorides which may be used include nitro and lower carbalkoxy isophthaloyl ch rides. One or more of the latter groups may be attached to the aromatic nucleus along with one or more alkyl, alkoxy, or halogen groups. Thus, it will be apparent that the aromatic radical of the isophthaloyl chloride may contain one or more of any combination of lower alkyl, lower alkoxy, halogen, nitro, phenyl, lower carbalkoxy, or other nompolyamide-forming groups.
- substituted terephthaloyl chlorides correspond to the substituted isophthaloyl chlorides described above and include lower alkyl, lower alkoxy, halogen, nitro, phenyl, and carbalkoxy substituted terephthaloyl chlorides. There may be one or more or a combination of these substituents attached to the aromatic ring so long as the total number of carbon atoms in all the substituents does not exceed nine.
- terephthaloyl chloride compounds which may be mentioned include, in addition to the terephthaloyl chloride itself, methyl-, ethyl-, propyl-, butyl-, etc., terephthaloyl chlorides, methoxy-, ethoxy-, propoxy-, butoxy-, etc., terephthaloyl chlorides, chloro-, bromo-, dichloro-, chlorobromo-, etc., terephthaloyl chlorides and nitro and lower carbalkoxy terephthaloyl chlorides.
- multiple ring diacid chlorides in which the acid chloride groups are oriented meta or para with respect to each other are also useful in this invention.
- Exemplary of such compounds are 4,4- methylenedibenzoyl chloride, 4,4'-oxydibenzoyl chloride, 4,4-sulfonyldibenzoyl chloride, 4,4'-dibenzoyl chloride, 3,3-oxydibenzoyl chloride, 3,3-sulfonyldibenzoyl chloride, and 3,3'-dibenzoyl chloride, the cor responding bromides and fluorides, and similar compounds in which one or both of the aromatic rings contains one or more or a combination of lower alkyl, lower alkoxy, halogen, nitro, sulfonyl, lower carbalkoxy groups.
- the diamines useful as reactants in forming the aromatic polyamides are compounds of the formulas HgN-AI'y-JQHg and R HNAt' NHR where R is hydrogen or lower alkyl and Ar, is a divalent aromatic radical as defined above and the --Nl-l and NHR groups are oriented meta or para with respect to each other.
- the diamines may contain single or multiple rings as well as fused rings.
- One or more hydrogens of the aromatic nucleus may be replaced by nonpolyamide-forming groups such as lower alkyl, lower alkoxy, halogen, nitro, sulfonyl, lower carbalkoxy as mentioned above.
- the aromatic nucleus of the diamines may be identical to any of the aromatic radicals mentioned above for the diacid chlorides, and the diamine utilized in any given instance may contain the same or different aromatic radical as the diacid chloride utilized.
- the total number of carbon atoms in the substituent groups attached to any aromatic ring should not exceed nine.
- Exemplary diamines which may be utilized in this invention include meta-phenylene diamine and lower alkyl substituted meta-phenylene diamine such as methyl-, ethyl-, propyl-, etc., meta-phenylene diamine; N,N'-dimethylmetaphenylene diamine, N,N'-diethylmetaphenylene diamine, etc. There may be more than one alkyl group attached to the aromatic ring as in the case of dimethyl, trimethyl, tetramethyl, diethyl, triethyl, and triisopropyl meta-phenylene diamine.
- alkyl substituent groups need not be the same because compounds such as 2-methyl-4-ethyl meta-phenylene diamine and 2-methyl-4-ethyl-5-propyl metaphenylene diamine may be utilized.
- the aromatic ring may be substituted with one or more lower alkoxy groups suchas, for example, methoxy-, ethoxy-, propoxy-, butoxy-, etc., meta-phenylene diamine.
- Other representative aromatic diamines which may be utilized include dimethoxy, trimethoxy, tetramethoxy, diethoxy meta-phenylene diamine, and 2 methoxy-4-ethoxy meta-phenylene diamine.
- Halogensubstituted meta-phenylene diamine as exemplified by chloro, bromo, and fluoro meta-phenylene diamine may be utilized. More than one halogen may be attached to the aromatic ring. The halogens in these compounds may be the same or different as in the case of the dihalo compound.
- Other meta-phenylene diamines which may be used include nitro and lower carbalkoxy meta-phenylene diamines. One or more of the latter groups may be attached to the aromatic nucleus along with one or more alkyl, alkoxy, or halogen groups so long as the total number of carbon atoms in the substituents attached to an aromatic ring does not exceed nine.
- multiple or fused ring aromatic diamines in which the amino groups are oriented meta or para with respect to each other are also useful in this invention.
- exemplary of such compounds are 4,4- diphenylmethene 4,4-oxydiphenyldiamine, 4,4'-sulfonyldiphenyldiamine, 4,4'-diphenyldiamine, 3,3-oxydiphenyldiamine, 3,3'-sulfonyldiphenyldiamine, and 3,3'-diphenyldiamine, and the corresponding compounds in which one or both of the aromatic rings contains one or more or a combination of lower alkyl, lower alkoxy, halogen, nitro, sulfonyl, lower carbalkoxy groups and the total number of carbon atoms in the substituent groups attached to an aromatic ring does not exceed nine.
- any or all of the conventional aromatic polyamides having high heat resistance can be advantageously dyed or printed in accordance with the process of the present invention.
- the present invention is not limited to any specific type of aromatic polyamide but any of those conventionally employed in the production of textile articles is applicable.
- thermostable synthetic polymer suitably employed in accordance with the present invention is of the polyamide-imide type, i.e. polymers obtainedthrough the reaction of a diamine or one or its derivatives and an acid anhydride or one of its derivatives.
- diamines are aromatic diisocyanates such as toluylene diisocyanate, 4 4diisocyanatop ny an t 4,4.qiisocy nawsli hcnylnroranq 4 4'diisocyanatodiphenylether etc.
- polyamide-imide type thermostable synthetic polymer one or more diamines is reacted with a polycarboxylic acid or derivative, preferably a tricarboxylic acid.
- a polycarboxylic acid or derivative preferably a tricarboxylic acid.
- any of the diamine reactants set forth above with respect to the preparation of the aromatic polyamide can be advantageously employed in connection with the production of polyamide-imide type thermostable synthetic polymers.
- the polycarboxylic acids which are advantageously employed in the production of the polyamide-imide type thermostable synthetic polymer include, for example, benzenel ,2,4-tricarboxylic acid (trimellitic acid), benqrhen a 3t3f i hqrsyliquas sitnanht ene- 245 tricarboxylic acid, etc. Of course, derivatives of these acids can advantageously be employed. Still further, in the production of the polyamide-imide type thermostable synthetic polymer a dibasic acid or derivative thereof is generally employed in the reaction system so as to produce the amide-imide linkage. Such dicarboxylic acids include any of those previously discussed in connection with the preparation of the aromatic polyamide.
- thermostable synthetic polymers suitably employed in accordance with the present invention
- U.S. Pat. No. 2,421,024 and British Pat. No. 570,858 which illustrate the preparation of such polymeric materials having fiber-forming characteristics. Accordingly, the disclosures of these references are herein incorporated by reference, noting again that any of the conventionally employed polyamideimide type thermostable synthetic polymers can be advantageously dyed or printed in accordance with the process of the present invention.
- thermostable synthetic polymers can be advantageously dyed or printed in accordance with the process of the present invention.
- heterocyclic polymers prepared from diamino-diamido compounds and polycarboxylic acid derivatives as set forth, for example, in U.S. Pat. No. 3,639,342 as well as the polybenzimidazoles, described, for example, in various patent literature as well as in the Journal of Polymer Science, Vol. L, pages 51 l 539, 1961, under Polybenzimidazoles, New Thermally Stable Polymers" by Herward Vogel and C. S. Marvel.
- polyamides such as described, for
- thermostable synthetic polymers can be advantageously modified by introduction of acid groups which favor coagulation of the polymer in the spinning bath and give to the polymer an affinity for basic dyes.
- acid groups which favor coagulation of the polymer in the spinning bath and give to the polymer an affinity for basic dyes.
- Such technique of modifying polymers by introduction of acid groups so as to provide an affinity for basic dyes is, of course well known in the art.
- thermostable synthetic polymers described above are dyed or printed in accordance with the present invention and a textile article having improved light fastness is obtained, by dyeing or printing the textile article through contact with a dyeing or printing solution containing a specifically identified adjuvant comprising an aromatic nitro compound having ultravioletlight absorbing capabilities.
- a specifically identified adjuvant comprising an aromatic nitro compound having ultravioletlight absorbing capabilities.
- nitro aromatic compound employed as the adjuvant in the dyeing or printing process of the present invention may be of the nitro aromatic phosphine type such as methyl-bis(N- nitrophen'yhphosphine oxide.
- the amount of such adjuvant is not critical and, the nitro aromatic compound need only be employed in an amount sufficient to create the desired light fastness in the dyed or printed textile article.
- the amount of nitro aromatic compound employed should be that which allows l to 5 percent, preferably l.5 to 3 percent, by weight of the nitro aromatic compound torernain on the dyed or printed textile article, the percentages being based upon the weight of the textile material.
- the amount of nitro aromatic compound to be employed in any particular dyeing or printing bath or solution can be easily calculated based upon the weight and pick-up of of the article to be dyed. Still further, due to the fact that the nitro aromatic compounds which adhere tothe textile article are those which provide the improved light fastness, those which are insoluble or just slightly soluble in water are preferred since such nitro aromatic compounds have been found to fix particularly well on the material to be dyed or printed.
- the dyeing or printing solution into which the adjuvant is incorporated can be any typically employed solution or bath for dyeing or printing textile articles.
- an aqueous solution of a suitable dye is advantageously utilized in accordance with the present invention, the dye bath or solution optionally containing other adjuvants such as carriers, equalizing agent, etc.
- the nature of the dye or printing bath or solution is not critical to the present invention and any such bath or solution conventionally employed can be utilized as long as the same contains the nitro aromatic compound as an adjuvant.
- the dyes which are utilized in the dyeing or printing solution can be any conventional dye which has been employed in connection with the dyeing of the abovenoted thermostable synthetic polymers. Accordingly,
- the present invention is not in any way to be limited to any specific dye or class of dyes.
- the dyes employed in accordance with the present invention are the conventionally used plastosoluble dyes with basic dyes being most preferrred, particularly where the polymer has been modified by the inclusion of acid groups.
- any conventionally employed dye can be advantageously utilized in carrying out the process of the present invention which, as previously noted, is
- the dyeing or printing process of the present invention it is not necessary to strictly adhere to rigid parameters although it can generally be said that the dyeing or printing should be carried out under such conditions that the nitro aromatic compound fixes on the textile material to be dyed in the amounts previously noted.
- the textile article may be treated in any conventional manner although it is preferred to rinse the dyed or printed article with hot water, i.e. about 80C.
- the washed textile article may then be immersed in a bath which contains a conventional non-ionic wetting agent and, if benzaldehyde is used, as the carrier, sodium bisulfite may additionally be present.
- Dyeing of the textile article is then carried out in a conventional manner.
- Each of these after-treatments is one which is conventionally adopted in the dyeing or printing of textile articles.
- the nitro aromatic compound as an adjuvant in the dyeing or printing of thermostable polymers, it is possible to produce dyed textile articles with high yield and good equalizing. Additionally, the articles dyed or printed in accordance with the present invention show improved light fastness without losing their wash resistance, resistance to treatment with solvents and resistance to wear.
- Example 1 A fabric weighing 125 g/m made up in warp and weft of filaments of 235 dtex (210 den), of a polyamide-imide, obtained by the reaction of 100 moles of 4 4'diisocyanatodiphenylmethane, with 80 moles of trimellitic anhydride, 16 moles of terephthalic acid and 4 moles of sulfo-S-isophthalic sodium salt, is dyed in a bath with a pH of 3-4, containing: I
- the fabric is dyed for 2 hours at 130C in an autoclave under pressure.
- the dyed fabric is then rinsed in hot water (80C) and immersed for 30 minutes in an aqueous bath heated to 95C and containing 5 cc/liter of sodium bisulfite solution 35Be' and l cc/liter of a condensate of ethylene oxide and a fatty alcohol. Drying is performed in an oven at 60C.
- the fabric which is obtained has an equalized orange dyeing and its light fastness is 5.
- the light fastness of an identical control fabric dyed under the same conditions but without introduction of l-methyl 2-amino 4- nitrobenzene in the dye bath is only 2-3. The improvement of the light fastness remains after washings and dry cleanings.
- Example 2 A fabric identical with that described in Example 1 is dyed under the same conditions as Example 1, except the dye bath contains:
- the fabric which is obtained has a Bordeaux red coloring with a light fastness of 3.
- the control fabric dyed under the same conditions, but without the presence of nitrobenzene has a light fastness of only 2.
- the improvement in light fastness remains after washings and dry cleanings.
- Example 3 A fabric identical with that of Example 1 is dyed under the same conditions as Example 1, except the dye bath contains: I
- the fabric obtained has a Bordeaux red coloring and a light fastness of 3-4.
- a control fabrc dyed under the same conditions but without vthe presence of methylbis(N-nitrophenyl) phosphine oxide has a light fastness of only 2.
- Example 4 A fabric identical with that described in Example 1 is dyed under the same conditions as Example 1. except the dye bath contains:
- the fabric obtained has a rather dark blue-green coloring, and a light fastness giving the results indicated in Table l.
- the table also has a comparison with a control fabric dyed under the same conditions but without the presence of l-methyl 2-amino 4-nitrobenzene and that of an identical fabric dyedv under the same conditions but by replacing l-methyl 2-amino 4-nitrobenzene with the same amount of 2-hydroxy 3,5-methyl-phenylbenzotriazole (standard ultraviolet ray absql'hcfli w Table 1 Control With 2-hydroxy With l-methyl 3,5-methylphenyl Z-amino benzotriazole 4-nitrobenzene Light fastness 4 4-5 6-7
- Example 5 A fabric identical with that described in Example 1 is dyed under the same conditions, except the dye bath contains:
- the fabric which is obtained has a rather dark orange coloring and a light fastness of 4.
- the light fastness of a control fabric dyed under the same conditions, but without the presence of b l-methyl 2- amino 4-nitrobenzene, is only 2.
- the improvement in the light fastness lasts after washings and dry cleanings.
- Example 7 Flock having a count per strand is 2.2 dtex (2 den) and a section length of 51 mm, of an aromatic polyamide obtained by the reaction of 50 moles of metaphenylene diamine and 50 moles of isophthalic acid chloride, is dyed under thesame conditions as in Example 1, except the dye bath contains:
- aromatic polyamide and polyamide-imide polymer is selected from aromatic polyamides and polyamide-imides having a heat resistance of 350 500C. 7
- nitro aromatic compound is a nitro aromatic phosphine oxide.
- a textile article composed at least in part of an aromatic polyamide and polyamide-imide synthetic polymer, said textile article having improved light fastness associated with the presence in said textile article of 1-5 percent by weight of a nitro aromatic compound whichis not used as a dye selected from nitro aromatic hydrocarbons, nitro aromatic t amines and nitro aromatic phosphine oxides.
- nitro aromatic compound is selected from nitro aromatic hydrocarbons, nitro aromatic amines and nitro aromatic phosphine oxides.
- nitro aromatic compound is a nitro aromatic hydrocarbon.
- nitro aromatic compound is a nitro aromatic phosphine oxide.
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Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7121770A FR2141556B1 (enrdf_load_stackoverflow) | 1971-06-14 | 1971-06-14 | |
NL7208000A NL7208000A (enrdf_load_stackoverflow) | 1971-06-14 | 1972-06-12 | |
GB2764372A GB1364000A (en) | 1971-06-14 | 1972-06-13 | Process for dyeing or printing textile articles |
LU65501D LU65501A1 (enrdf_load_stackoverflow) | 1971-06-14 | 1972-06-13 | |
BE784808A BE784808A (fr) | 1971-06-14 | 1972-06-13 | Nouveau procede de teinture ou d'impression d'articles textilesen polymeres synthetiques thermostables |
US00262441A US3802841A (en) | 1971-06-14 | 1972-06-14 | Nitro aromatic hydrocarbon,amino nitro aromatic & nitro aromatic phosphine oxides on aromatic polyamide-imide as light fading inhibitors for dyes thereon |
DE19722229046 DE2229046A1 (de) | 1971-06-14 | 1972-06-14 | Verfahren zum Färben oder Bedrucken von Textilerzeugnissen aus wärmebeständigen synthetischen Polymeren |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7121770A FR2141556B1 (enrdf_load_stackoverflow) | 1971-06-14 | 1971-06-14 | |
US00262441A US3802841A (en) | 1971-06-14 | 1972-06-14 | Nitro aromatic hydrocarbon,amino nitro aromatic & nitro aromatic phosphine oxides on aromatic polyamide-imide as light fading inhibitors for dyes thereon |
Publications (1)
Publication Number | Publication Date |
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US3802841A true US3802841A (en) | 1974-04-09 |
Family
ID=26216457
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00262441A Expired - Lifetime US3802841A (en) | 1971-06-14 | 1972-06-14 | Nitro aromatic hydrocarbon,amino nitro aromatic & nitro aromatic phosphine oxides on aromatic polyamide-imide as light fading inhibitors for dyes thereon |
Country Status (7)
Country | Link |
---|---|
US (1) | US3802841A (enrdf_load_stackoverflow) |
BE (1) | BE784808A (enrdf_load_stackoverflow) |
DE (1) | DE2229046A1 (enrdf_load_stackoverflow) |
FR (1) | FR2141556B1 (enrdf_load_stackoverflow) |
GB (1) | GB1364000A (enrdf_load_stackoverflow) |
LU (1) | LU65501A1 (enrdf_load_stackoverflow) |
NL (1) | NL7208000A (enrdf_load_stackoverflow) |
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-
1971
- 1971-06-14 FR FR7121770A patent/FR2141556B1/fr not_active Expired
-
1972
- 1972-06-12 NL NL7208000A patent/NL7208000A/xx unknown
- 1972-06-13 LU LU65501D patent/LU65501A1/xx unknown
- 1972-06-13 BE BE784808A patent/BE784808A/xx unknown
- 1972-06-13 GB GB2764372A patent/GB1364000A/en not_active Expired
- 1972-06-14 US US00262441A patent/US3802841A/en not_active Expired - Lifetime
- 1972-06-14 DE DE19722229046 patent/DE2229046A1/de active Pending
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US20040120920A1 (en) * | 2002-09-26 | 2004-06-24 | Bertrand Lion | Novel block polymers and cosmetic compositions and processes comprising them |
US20060134051A1 (en) * | 2002-09-26 | 2006-06-22 | Xavier Blin | Glossy non-transfer composition comprising a sequenced polymer |
US20060134044A1 (en) * | 2002-09-26 | 2006-06-22 | Xavier Blin | Cosmetic composition comprising a sequenced polymer and a plasticizer |
US20060147402A1 (en) * | 2002-09-26 | 2006-07-06 | Xavier Blin | Composition comprising a sequenced polymer and a gelling agent |
US20060147403A1 (en) * | 2002-09-26 | 2006-07-06 | L'oreal C.A. | Non-transfer cosmetic composition comprising a sequenced polymer |
US7915347B2 (en) | 2002-09-26 | 2011-03-29 | L'oreal S.A. | Block polymers and cosmetic compositions and processes comprising them |
US7803877B2 (en) | 2002-09-26 | 2010-09-28 | L'oreal S.A. | Block polymers and cosmetic compositions and processes comprising them |
US7993632B2 (en) | 2002-12-20 | 2011-08-09 | L'oreal S.A. | Composition for coating keratin fibres having a threading nature |
US20040191200A1 (en) * | 2002-12-20 | 2004-09-30 | Lezer Nathalie Jager | Composition for coating keratin fibres having a threading nature |
US20050005002A1 (en) * | 2003-07-02 | 2005-01-06 | International Business Machines Corporation | Administering device with domain state objects |
US20050175650A1 (en) * | 2003-07-08 | 2005-08-11 | Anke Hadasch | Composition comprising an elastomeric organopolysiloxane and additional particles |
US8119110B2 (en) | 2003-09-26 | 2012-02-21 | L'oreal S.A. | Cosmetic composition comprising a block polymer and a non-volatile silicone oil |
US20050106197A1 (en) * | 2003-09-26 | 2005-05-19 | Xavier Blin | Cosmetic composition comprising a block polymer and a non-volatile silicone oil |
US20050095213A1 (en) * | 2003-09-26 | 2005-05-05 | Xavier Blin | Two-coat cosmetic product, cosmetic process of using thereof and makeup kit containing this product |
US20050175562A1 (en) * | 2004-01-05 | 2005-08-11 | Anke Hadasch | Skin makeup composition |
US7820151B2 (en) | 2004-02-13 | 2010-10-26 | L'oreal S.A. | Composition for coating keratin fibers, comprising at least one tacky wax and fibers |
US20050191259A1 (en) * | 2004-02-13 | 2005-09-01 | Sue Feng | Composition for coating keratin fibers, comprising at least one tacky microcrystalline wax and fibers |
US20050215679A1 (en) * | 2004-02-13 | 2005-09-29 | De La Poterie Valerie | Composition for coating keratin fibers, comprising at least one tacky wax and fibers |
US20050220731A1 (en) * | 2004-03-23 | 2005-10-06 | Philippe Ilekti | Nail varnish composition comprising at least one polymer and at least one plasticizer |
US8728451B2 (en) | 2004-03-25 | 2014-05-20 | L'oreal | Styling composition comprising, in a predominantly aqueous medium, a pseudo-block polymer, processes employing same and uses thereof |
US7854017B2 (en) | 2005-12-16 | 2010-12-21 | Southern Mills, Inc. | Protective garments that provide thermal protection |
US20070249247A1 (en) * | 2006-04-20 | 2007-10-25 | Truesdale Rembert J Iii | Ultraviolet-resistant fabrics and methods for making them |
US20080153372A1 (en) * | 2006-04-20 | 2008-06-26 | Southern Mills | Insect-Repellant Fabrics and Methods for Making Them |
US7862865B2 (en) | 2006-04-20 | 2011-01-04 | Southern Mills, Inc. | Ultraviolet-resistant fabrics and methods for making them |
US7811952B2 (en) | 2006-04-20 | 2010-10-12 | Southern Mills, Inc. | Ultraviolet-resistant fabrics and methods for making them |
US20070248765A1 (en) * | 2006-04-20 | 2007-10-25 | Rembert Joseph Truesdale | Ultraviolet-resistant fabrics and methods for making them |
EP2377991A3 (en) * | 2006-04-20 | 2011-12-28 | Southern Mills, Inc. | Ultraviolet-resistant fabrics and methods for making them |
WO2007133177A3 (en) * | 2006-04-20 | 2008-05-22 | Southern Mills Inc | Ultraviolet-resistant fabrics and methods for making them |
WO2007133177A2 (en) | 2006-04-20 | 2007-11-22 | Southern Mills, Inc. | Ultraviolet-resistant fabrics and methods for making them |
US8710152B2 (en) | 2006-07-27 | 2014-04-29 | L'oreal | Block polymers and their process of preparation |
US20080031837A1 (en) * | 2006-07-27 | 2008-02-07 | Celine Farcet | Block polymers and their process of preparation |
WO2010063952A2 (fr) | 2008-12-02 | 2010-06-10 | L'oreal | Procede de maquillage des cils ou sourcils utilisant une resine de siloxane et un compose particulier et kit associe |
US9216145B2 (en) | 2009-10-27 | 2015-12-22 | The Procter & Gamble Company | Semi-permanent cosmetic concealer |
US9237992B2 (en) | 2009-10-27 | 2016-01-19 | The Procter & Gamble Company | Two-step mascara product |
US9004791B2 (en) | 2010-04-30 | 2015-04-14 | The Procter & Gamble Company | Package for multiple personal care compositions |
US10034829B2 (en) | 2010-10-27 | 2018-07-31 | Noxell Corporation | Semi-permanent mascara compositions |
US9173824B2 (en) | 2011-05-17 | 2015-11-03 | The Procter & Gamble Company | Mascara and applicator |
WO2013163502A1 (en) | 2012-04-26 | 2013-10-31 | The Procter & Gamble Company | Two-step mascara product |
US9140681B2 (en) | 2012-05-15 | 2015-09-22 | The Procter & Gamble Company | Method for quantitatively determining eyelash clumping |
Also Published As
Publication number | Publication date |
---|---|
FR2141556A1 (enrdf_load_stackoverflow) | 1973-01-26 |
DE2229046A1 (de) | 1972-12-21 |
BE784808A (fr) | 1972-12-13 |
GB1364000A (en) | 1974-08-21 |
LU65501A1 (enrdf_load_stackoverflow) | 1972-10-23 |
NL7208000A (enrdf_load_stackoverflow) | 1972-12-18 |
FR2141556B1 (enrdf_load_stackoverflow) | 1974-03-22 |
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