US3717491A - Dye compositions - Google Patents
Dye compositions Download PDFInfo
- Publication number
- US3717491A US3717491A US00065312A US3717491DA US3717491A US 3717491 A US3717491 A US 3717491A US 00065312 A US00065312 A US 00065312A US 3717491D A US3717491D A US 3717491DA US 3717491 A US3717491 A US 3717491A
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- United States
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- composition
- organic acid
- percent
- acid compound
- pigment
- Prior art date
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- Expired - Lifetime
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- 239000000203 mixture Substances 0.000 title claims description 56
- -1 organic acid compound Chemical class 0.000 claims abstract description 46
- 239000000049 pigment Substances 0.000 claims description 33
- 239000007767 bonding agent Substances 0.000 claims description 26
- 239000006185 dispersion Chemical class 0.000 claims description 16
- 239000002270 dispersing agent Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical group CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 claims description 10
- 239000000661 sodium alginate Substances 0.000 claims description 10
- 235000010413 sodium alginate Nutrition 0.000 claims description 10
- 229940005550 sodium alginate Drugs 0.000 claims description 10
- 238000009980 pad dyeing Methods 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000008240 homogeneous mixture Substances 0.000 claims description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
- 239000004471 Glycine Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 239000004744 fabric Substances 0.000 description 34
- 239000004753 textile Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- 239000002689 soil Substances 0.000 description 12
- 238000004043 dyeing Methods 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 6
- 238000004900 laundering Methods 0.000 description 6
- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical compound NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- 239000001023 inorganic pigment Substances 0.000 description 3
- 239000012860 organic pigment Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 102000011632 Caseins Human genes 0.000 description 2
- 108010076119 Caseins Proteins 0.000 description 2
- 239000001856 Ethyl cellulose Substances 0.000 description 2
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 238000005108 dry cleaning Methods 0.000 description 2
- 235000019325 ethyl cellulose Nutrition 0.000 description 2
- 229920001249 ethyl cellulose Polymers 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229960002449 glycine Drugs 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- OSNILPMOSNGHLC-UHFFFAOYSA-N 1-[4-methoxy-3-(piperidin-1-ylmethyl)phenyl]ethanone Chemical compound COC1=CC=C(C(C)=O)C=C1CN1CCCCC1 OSNILPMOSNGHLC-UHFFFAOYSA-N 0.000 description 1
- JIOVPPZHKHZULI-UHFFFAOYSA-N 2,2-difluoro-2-[fluoro(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoyl)amino]acetic acid Chemical compound OC(=O)C(F)(F)N(F)C(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JIOVPPZHKHZULI-UHFFFAOYSA-N 0.000 description 1
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- VZIBAMYIHSHADC-UHFFFAOYSA-N 5-nitro-1,3-dihydro-2-benzofuran Chemical compound [O-][N+](=O)C1=CC=C2COCC2=C1 VZIBAMYIHSHADC-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229920002972 Acrylic fiber Polymers 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920000896 Ethulose Polymers 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000001859 Ethyl hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N N-methylaminoacetic acid Natural products C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241001300834 Pictetia aculeata Species 0.000 description 1
- 206010037867 Rash macular Diseases 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 108010077895 Sarcosine Proteins 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- VAPILSUCBNPFBS-UHFFFAOYSA-L disodium 2-oxido-5-[[4-[(4-sulfophenyl)diazenyl]phenyl]diazenyl]benzoate Chemical compound [Na+].[Na+].Oc1ccc(cc1C([O-])=O)N=Nc1ccc(cc1)N=Nc1ccc(cc1)S([O-])(=O)=O VAPILSUCBNPFBS-UHFFFAOYSA-L 0.000 description 1
- 230000003028 elevating effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000019326 ethyl hydroxyethyl cellulose Nutrition 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 235000021384 green leafy vegetables Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 235000019239 indanthrene blue RS Nutrition 0.000 description 1
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- YOBAEOGBNPPUQV-UHFFFAOYSA-N iron;trihydrate Chemical compound O.O.O.[Fe].[Fe] YOBAEOGBNPPUQV-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- JHOKTNSTUVKGJC-UHFFFAOYSA-N n-(hydroxymethyl)octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCO JHOKTNSTUVKGJC-UHFFFAOYSA-N 0.000 description 1
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 150000004812 organic fluorine compounds Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004302 potassium sorbate Substances 0.000 description 1
- 235000010241 potassium sorbate Nutrition 0.000 description 1
- 229940069338 potassium sorbate Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229940080237 sodium caseinate Drugs 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 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
- 238000012360 testing method Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 235000014692 zinc oxide Nutrition 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0084—Guluromannuronans, e.g. alginic acid, i.e. D-mannuronic acid and D-guluronic acid units linked with alternating alpha- and beta-1,4-glycosidic bonds; Derivatives thereof, e.g. alginates
-
- 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
- D06P1/647—Nitrogen-containing carboxylic acids or their salts
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/651—Compounds without nitrogen
- D06P1/65106—Oxygen-containing compounds
- D06P1/65125—Compounds containing ester groups
Definitions
- ABSTRACT A fluorinated organic acid compound of the formula C F CoNRCl-lRCooH
- the present invention relates to compositions for dyeing textiles with insoluble pigments and more particularly, to the preparation of improved pad dyeing compositions obtained by the incorporation of certain fluorinated organic acid compounds with a dispersion containing a pigment, a bonding agent and a dispersing agent.
- pigment dyeing systems consist of a dispersion of finely ground pigment and binder compound.
- One method of pad dyeing is to immerse the textile in a bath containing the pigment and binder compound and then pass the textile between squeeze rolls which remove the excess of color and other bath constituents.
- one of the squeeze rolls is partially immersed in the color bath, whereby some of the bath is carried to the nip between the partially immersed roll and the roll adjacent to it. In the latter case, the textile is dyed by passing between the rolls without previous immersion in the bath.
- the amount of pigment in respect to the amount of resin binder employed will vary with the character of pigment and the depth of color desired.
- the pigment should impinge on the fabric surface with a minimum of excess binder resin protecting the surface.
- the process of pad dyeing with pigments has had serious drawbacks.
- One of these drawbacks is the fact that the pigment dyed textile may have what is described as poor appearance. In other words, the dyeing is uneven, showing dark areas and light areas in the textile material. This unevenness may be due to the migration of the pigment.
- Another drawback is the fact that the pigment dyed textile material does not have durability to dry cleaning and laundering.
- fluorochemicals have been used to impart soil repellency characteristics to textiles and are in fact 'used commercially today for that purpose, it was unexpected to find that certain fluorochemicals can be incorporated into dye compositions to improve the uniformity of fabric dyeing and to impart durability to the dye applied to the fabrics.
- An object of the present invention is to provide improved pad dyeing compositions and a method of preparing the same.
- Another object of the present invention is to provide dye compositions, comprising certain fluorinated organic acid compounds and a dispersion containing a pigment, bonding agent and dispersing agent, which provide uniformity of fabric dyeing and impart durability to the dye applied to the fabric.
- Still another object of the present invention is to provide pad dyeing compositions having improved uniformity of fabric dyeing together with soil repellency and soil release characteristics.
- bonding agent is added to a dispersion of pigment and the total material is stirred until homogeneous.
- the dispersing agent preferably sodium alginate
- the bath is then adjusted to a pl-I equal to or greater than 8 by the addition of a base.
- the fluorinated organic acid compound is added to the aqueous dispersion and the resulting mixture is stirred until the composition is homogeneous.
- the resulting composition constitutes the bath which is used for padding fabric. Typically, the fabric is weighed before and after padding, and the pressure on the padding rolls is adjusted to yield the desired wet pickup of the composition.
- the fluorinated organic acid compounds employed in this invention have the structure C F CONRCHRCOOH wherein each R is independently selected from H or an alkyl radical of one to eight carbon atoms and n is an integer of 6 to 18.
- Representative compounds include perfluorohexanoylamino acetic acid, perfluorooctanoylamino acetic acid, perfluoroundecanoylamino acetic acid, perfluoropentadecanoylamino acetic acid, perfluorooctadecanoyl amino acetic acid, perfluoroheptanoyl-Z-amino propionic acid, perfluorooctanoyl-2-amino butyric acid and perfluoroundecanoyl- 2-aminobutyric acid, perfluorooctanoyl sarcosine and perfluoroundecanoyl-Z-amino caprylic acid.
- organic and inorganic pigments may be employed in the present invention.
- Such pigments include such natural organic pigments as fustic and tumeric; such synthetic organic pigments as indanthrene blues, naphthol yellows, azo reds and phthalocyanine greens; such natural inorganic pigments as umber, and ochre; and such synthetic inorganic pigments as iron blues, chrome orange, cadmium reds, zinc whites, iron oxide brown and the like.
- the pigments employed will be inert with respect to the balance of the dye composition and be fast to light.
- the pigments should be nonbleeding, and unaffected by cleaning solutions and soaps. Based on the active weight to be deposited on the fabric, the amount of pigment employed can vary between 0.1 to 15 percent by weight of the fabric weight, with 2 to 10 percent being a preferred amount.
- aqueous dispersion is preferred, but'various non-aqueous systems, including alcohols, ketones, etc., can be employed.
- the bonding agent utilized in the present invention can include any of the bonding agents normally employed in the art, such as urea formaldehyde, melamine formaldehyde, ethyl cellulose, mixtures of ethyl and butyl cellulose, carboxymethyl cellulose, ethylacrylate homopolymers and copolymers, methyl methacrylate homopolymers and copolymers, and the like.
- Specific examples of alkylated melamine formaldehyde condensation products which may be used in accordance with this invention include propylated methylol-melamine, butylated methylol-melamine, hexylated methylolmelamine, cyclohexylated methylol-melamine, etc.
- the bonding agent constitutes a resin emulsion such as an acrylate emulsion containing at least one reactive pendant group, such as N-methylol acrylamide.
- a resin emulsion such as an acrylate emulsion containing at least one reactive pendant group, such as N-methylol acrylamide.
- both natural bonding agents such as albumen and casein
- synthetic bonding agents such as ethyl cellulose, hydroxyethyl cellulose and urea formaldehyde.
- the choice of the particular bonding agent was extremely critical since the fastness of pigment-dyed fabrics to washing, dry-cleaning, scrubbing and abrasion depended largely upon the type of bonding material employed. In fact, it was not uncommon to employ combinations of two or more types of bonding agents in order to attempt to obtain all of the desired characteristics.
- the present invention provides a marked improvement in this area in permitting use of a single bonding agent to obtain a greater number of advantages. Based on the percentage of active weight to be deposited on the fabric, between 1 to 20 percent of the bonding agent can be employed, with a preferred amount being in the range of about 4 to percent.
- the dispersing agent utilized in the present invention can be of the type normally employed in the art. It is not unknown to employ a material as the dispersing agent which in some formulation may serve as a bonding agent. Such additives may thus be carboxymethyl cellulose, hydroxyethyl cellulose, sodium lignosulfonate, sodium caseinate, or other. Particularly preferred is sodium alginate as the dispersing agent.
- the sodium alginate is typically added to the other ingredients as a dispersion of the sodium alginate in liquid such that, based on the percent of active weight to be deposited on the fabric, an effective amount between 0.025 and 2 percent of sodium alginate is employed, with the preferred amount being in the vicinity of 0.07 to 1.0 percent. Since the preferred dispersion system is an aqueous system, normally a dispersion of sodium alginate in water is added to the homogeneous aqueous dispersion of pigment and bonding agent.
- aqueous ammonia In order to regulate the pH in a range to or greater than 8, aqueous ammonia is normally employed. However, any amine which can be volatilized at moderate temperatures can be employed. Such amines include ethylamine and isopropylamine.
- Textile materials such as cotton fabrics, Dacron-cotton fabrics, polyester fabrics, rayon blends, nylon, Orlon, and similar textile materials are normally treated by running the textile material through a padding bath maintained at a temperature between about 65F. and 180F.
- Pickup of the padding composition is controlled by regulating the pressure of squeeze rolls to yield the desired wet pickup, e.g. about percent of the weight of the dry fabric being treated.
- an adequate cure time for the treated fabric is 15 minutes at 325F.
- the cure time can be shortened by elevating the temperature. The actual time and temperature used depend on the weight of the fabric and to a lesser degree on the depth of shade applied.
- EXAMPLE I A dye composition of the following materials was prepared containing approximately 8.318 percent active weight of materials diluted to percent with The above dye composition was padded onto a 65/35 unsized polyester/cotton fabric to deposit an 85 percent wet pickup, based on the weight of the fabric. Thus, 85 percent of the value shown under percent active weight in the above table was deposited on the fabric.
- the fabric treated with the dye composition in the manner indicated above was compared to identical fabric similarly treated except for the absence of a fluorinated organic acid compound in the dye composition. It was found that the dyed fabric containing the fluorochemical was (1) dyed more uniformly, (2) that the dye was more durable to laundering, and (3) that the dyed fabric showed improved soil repellency and soil release characteristics.
- a photoelectric reflection meter having a green tristimulus filter was employed to measure the percent reflectance of padded swatches to reveal the durability and soil release characteristics of both the control dye composition and the dye composition containing fluorinated organic acid compounds in accordance with the present invention.
- the padded swatches were cured in a gravity feed circulating hot air oven at 325F. for 15 minutes and then allowed to equilibriate for 24 hours at 50 percent relative humidity at a temperature of 73F. before testing commenced. Soiling of the padded swatches was made with the synthetic soil described in the article by J. M. Salsbury et al. entitled Soil Resistant Treatment of Fabrics in The American Dyestujj Reporter for Mar. 26, 1956. Laundering of soiled fabric swatches was done as described in AATCC Test Method 61, No. IllA, except that 0.2 percent Tide was employed and no sodium metasilicate was employed.
- a 62 percent reflectance was obtained from both the control padded swatch and the padded swatch containing the fluorinated organic acid compounds of the present invention.
- the reflectance of the control padded swatch fell to 44 percent, whereas, after one soiling and washing by AATCC Test Method 61, No. 111A, the padded swatches prepared using the fluorinated organic acid compounds of the present invention had a reflectance value of 61 percent. Even after repeating the soiling and washing procedure on the padded swatches prepared in accordance with the present invention the reflectance value was 58 percent.
- This fluorochemical composition was substituted on the basis of fluorochemical content for the perfluoroctanoyl glycine of Example I in the dye composition otherwise similar to that according to Example I and thereafter applied and tested as in Example I.
- the pad dyed swatches had and uneven and blotchy appearance of the applied dye and were lacking in fastness properties during laundering. Soil release properties likewise were unsatisfactory.
- anti-soiling substances such as aluminum silicate; preservatives, such as sodium benzoate or potassium sorbate; water-proofing agents, such as methylol stearamide and methylene-bis-stearamide; anti-static agents; heat stability additives; buffering agents, such as diarnmonium phosphate; etc. may be incorporated into the formulations of the present invention.
- a pad dyeing composition comprising a fluorinated organic acid compound and a dispersion of a pigment, bonding agent and dispersing agent said organic acid compound having the formula:
- each R is independently selected from H or an alkyl radical of one to eight carbon atoms and n is an integer of 6 to 18.
- composition of claim 1 wherein the dispersing agent is sodium alginate.
- composition of claim 2 wherein the sodium alginate is present in an effective amount, but not more than about two percent by weight.
- composition of claim 1 wherein the fluorinated organic acid compound is present in an amount from about 0.1 to about 5 percent by weight.
- composition of claim 1 wherein the pigment is present in an amount from about 0.1 to about 10 percent by weight.
- composition of claim 1 wherein the bonding agent is present in an amount from about 1 to about 20 percent by weight.
- composition of claim 1 wherein the fluorinated organic acid compound is perfluorooctanoyl glycine.
- a method of making a pad dyeing composition comprising adding a bonding agent to a dispersion of pigment and stirring the bonding agent and pigment until a homogeneous mixture is obtained, adding dispersing agent to the homogeneous mixture of bonding agent and pigment, adjusting the mixture to a pH of at least 8, and adding a fluorinated organic acid compound to the resulting mixture, said organic acid compound having the formula:
- each R is independently selected from H or an alkyl radical of one to eight carbon atoms and n is an integer of 6 to 18.
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Abstract
A fluorinated organic acid compound of the formula
Description
United States Patent [191 Uffner Feb. 20, 1973 [541 DYE COMPOSITIONS [751 Inventor: Melville W. Uffner, Media, Pa.
[73] Assignee: Air Products and Chemicals, Inc.,
Philadelphia, Pa.
[22] Filed: Aug. 19, 1970 [21] Appl. No.: 65,312
[52] U.S. Cl. ..l06/209, 8/65, 117/1355, 117/1395 C, 260/296 F [51] Int. Cl. ..C08b 25/00 [58] Field of Search ..l06/l62, 209; 260/296 F; 8/65;117/139.5 C, 135.5; 165/313 [56] References Cited UNITED STATES PATENTS 3,576,019 4/1971 Sweeney ..260/404.5
3,282,717 11/1966 Kelley ..106/205 3,414,368 3/1968 Kitamul'a 3,238,235 1/1966 Hauptschein ..260/29.6 F
Primary Examiner-Theodore Morris Att0rneyB. Max Klevit and David T. Nikaido [57] ABSTRACT A fluorinated organic acid compound of the formula C F CoNRCl-lRCooH,
13 Claims, No Drawings DYE coMPosmoNs BACKGROUND OF THE INVENTION The present invention relates to compositions for dyeing textiles with insoluble pigments and more particularly, to the preparation of improved pad dyeing compositions obtained by the incorporation of certain fluorinated organic acid compounds with a dispersion containing a pigment, a bonding agent and a dispersing agent.
conventionally, pigment dyeing systems consist of a dispersion of finely ground pigment and binder compound. One method of pad dyeing is to immerse the textile in a bath containing the pigment and binder compound and then pass the textile between squeeze rolls which remove the excess of color and other bath constituents. As an alternative method, one of the squeeze rolls is partially immersed in the color bath, whereby some of the bath is carried to the nip between the partially immersed roll and the roll adjacent to it. In the latter case, the textile is dyed by passing between the rolls without previous immersion in the bath. The amount of pigment in respect to the amount of resin binder employed will vary with the character of pigment and the depth of color desired. Properly applied, the pigment should impinge on the fabric surface with a minimum of excess binder resin protecting the surface. The process of pad dyeing with pigments has had serious drawbacks. One of these drawbacks is the fact that the pigment dyed textile may have what is described as poor appearance. In other words, the dyeing is uneven, showing dark areas and light areas in the textile material. This unevenness may be due to the migration of the pigment. Another drawback is the fact that the pigment dyed textile material does not have durability to dry cleaning and laundering.
Although fluorochemicals have been used to impart soil repellency characteristics to textiles and are in fact 'used commercially today for that purpose, it was unexpected to find that certain fluorochemicals can be incorporated into dye compositions to improve the uniformity of fabric dyeing and to impart durability to the dye applied to the fabrics.
SUMMARY OF THE INVENTION An object of the present invention is to provide improved pad dyeing compositions and a method of preparing the same.
Another object of the present invention is to provide dye compositions, comprising certain fluorinated organic acid compounds and a dispersion containing a pigment, bonding agent and dispersing agent, which provide uniformity of fabric dyeing and impart durability to the dye applied to the fabric.
Still another object of the present invention is to provide pad dyeing compositions having improved uniformity of fabric dyeing together with soil repellency and soil release characteristics.
These and other objects, advantages and features of the invention are obtained by the addition of 0.1 to 5 percent by weight of a fluorinated organic acid compound having the formula wherein each R is independently selected from H or an alkyl radical of one to eight carbon atoms, and n is an integer of 6 to 18, to a dispersion containing a pigment, bonding agent and a dispersing agent. The resulting dye compositions not only permit fabrics to be dyed more uniformly, but impart durability to the dye applied to the fabric, such that the dye is more durable to more laundering. The dyeing compositions of the present invention also render the dyed fabric soil repellent.
DESCRIFI'ION OF THE PREFERRED EMBODIMENTS In a preferred embodiment of the invention, bonding agent is added to a dispersion of pigment and the total material is stirred until homogeneous. The dispersing agent, preferably sodium alginate, is then added to the homogeneous material. For maximum pad bath stability, the bath is then adjusted to a pl-I equal to or greater than 8 by the addition of a base. Finally, the fluorinated organic acid compound is added to the aqueous dispersion and the resulting mixture is stirred until the composition is homogeneous. The resulting composition constitutes the bath which is used for padding fabric. Typically, the fabric is weighed before and after padding, and the pressure on the padding rolls is adjusted to yield the desired wet pickup of the composition.
The fluorinated organic acid compounds employed in this invention have the structure C F CONRCHRCOOH wherein each R is independently selected from H or an alkyl radical of one to eight carbon atoms and n is an integer of 6 to 18. Representative compounds include perfluorohexanoylamino acetic acid, perfluorooctanoylamino acetic acid, perfluoroundecanoylamino acetic acid, perfluoropentadecanoylamino acetic acid, perfluorooctadecanoyl amino acetic acid, perfluoroheptanoyl-Z-amino propionic acid, perfluorooctanoyl-2-amino butyric acid and perfluoroundecanoyl- 2-aminobutyric acid, perfluorooctanoyl sarcosine and perfluoroundecanoyl-Z-amino caprylic acid. These fluorinated organic acid compounds are synthesized from organic fluorine compounds prepared by either telomerization or electrolytic fluorination.
All commercially available organic and inorganic pigments may be employed in the present invention. Such pigments include such natural organic pigments as fustic and tumeric; such synthetic organic pigments as indanthrene blues, naphthol yellows, azo reds and phthalocyanine greens; such natural inorganic pigments as umber, and ochre; and such synthetic inorganic pigments as iron blues, chrome orange, cadmium reds, zinc whites, iron oxide brown and the like. Advantageously, the pigments employed will be inert with respect to the balance of the dye composition and be fast to light. In addition, the pigments should be nonbleeding, and unaffected by cleaning solutions and soaps. Based on the active weight to be deposited on the fabric, the amount of pigment employed can vary between 0.1 to 15 percent by weight of the fabric weight, with 2 to 10 percent being a preferred amount.
For printing and dyeing of textiles, the usual procedure is to disperse the pigment particles in a liquid. An aqueous dispersion is preferred, but'various non-aqueous systems, including alcohols, ketones, etc., can be employed.
The bonding agent utilized in the present invention can include any of the bonding agents normally employed in the art, such as urea formaldehyde, melamine formaldehyde, ethyl cellulose, mixtures of ethyl and butyl cellulose, carboxymethyl cellulose, ethylacrylate homopolymers and copolymers, methyl methacrylate homopolymers and copolymers, and the like. Specific examples of alkylated melamine formaldehyde condensation products which may be used in accordance with this invention include propylated methylol-melamine, butylated methylol-melamine, hexylated methylolmelamine, cyclohexylated methylol-melamine, etc. Preferably, the bonding agent constitutes a resin emulsion such as an acrylate emulsion containing at least one reactive pendant group, such as N-methylol acrylamide. Thus, both natural bonding agents, such as albumen and casein, and synthetic bonding agents, such as ethyl cellulose, hydroxyethyl cellulose and urea formaldehyde, can be employed. Prior to the present invention, the choice of the particular bonding agent was extremely critical since the fastness of pigment-dyed fabrics to washing, dry-cleaning, scrubbing and abrasion depended largely upon the type of bonding material employed. In fact, it was not uncommon to employ combinations of two or more types of bonding agents in order to attempt to obtain all of the desired characteristics. The present invention provides a marked improvement in this area in permitting use of a single bonding agent to obtain a greater number of advantages. Based on the percentage of active weight to be deposited on the fabric, between 1 to 20 percent of the bonding agent can be employed, with a preferred amount being in the range of about 4 to percent.
The dispersing agent utilized in the present invention can be of the type normally employed in the art. It is not unknown to employ a material as the dispersing agent which in some formulation may serve as a bonding agent. Such additives may thus be carboxymethyl cellulose, hydroxyethyl cellulose, sodium lignosulfonate, sodium caseinate, or other. Particularly preferred is sodium alginate as the dispersing agent. The sodium alginate is typically added to the other ingredients as a dispersion of the sodium alginate in liquid such that, based on the percent of active weight to be deposited on the fabric, an effective amount between 0.025 and 2 percent of sodium alginate is employed, with the preferred amount being in the vicinity of 0.07 to 1.0 percent. Since the preferred dispersion system is an aqueous system, normally a dispersion of sodium alginate in water is added to the homogeneous aqueous dispersion of pigment and bonding agent.
In order to regulate the pH in a range to or greater than 8, aqueous ammonia is normally employed. However, any amine which can be volatilized at moderate temperatures can be employed. Such amines include ethylamine and isopropylamine.
Textile materials such as cotton fabrics, Dacron-cotton fabrics, polyester fabrics, rayon blends, nylon, Orlon, and similar textile materials are normally treated by running the textile material through a padding bath maintained at a temperature between about 65F. and 180F. Pickup of the padding composition is controlled by regulating the pressure of squeeze rolls to yield the desired wet pickup, e.g. about percent of the weight of the dry fabric being treated. Normally an adequate cure time for the treated fabric is 15 minutes at 325F. Of course, the cure time can be shortened by elevating the temperature. The actual time and temperature used depend on the weight of the fabric and to a lesser degree on the depth of shade applied.
While the following examples illustrate the nature of the present invention, the invention is not intended to be limited to these specific embodiments.
EXAMPLE I A dye composition of the following materials was prepared containing approximately 8.318 percent active weight of materials diluted to percent with The above dye composition was padded onto a 65/35 unsized polyester/cotton fabric to deposit an 85 percent wet pickup, based on the weight of the fabric. Thus, 85 percent of the value shown under percent active weight in the above table was deposited on the fabric.
The fabric treated with the dye composition in the manner indicated above was compared to identical fabric similarly treated except for the absence of a fluorinated organic acid compound in the dye composition. It was found that the dyed fabric containing the fluorochemical was (1) dyed more uniformly, (2) that the dye was more durable to laundering, and (3) that the dyed fabric showed improved soil repellency and soil release characteristics.
A photoelectric reflection meter having a green tristimulus filter was employed to measure the percent reflectance of padded swatches to reveal the durability and soil release characteristics of both the control dye composition and the dye composition containing fluorinated organic acid compounds in accordance with the present invention. In each instance, the padded swatches were cured in a gravity feed circulating hot air oven at 325F. for 15 minutes and then allowed to equilibriate for 24 hours at 50 percent relative humidity at a temperature of 73F. before testing commenced. Soiling of the padded swatches was made with the synthetic soil described in the article by J. M. Salsbury et al. entitled Soil Resistant Treatment of Fabrics in The American Dyestujj Reporter for Mar. 26, 1956. Laundering of soiled fabric swatches was done as described in AATCC Test Method 61, No. IllA, except that 0.2 percent Tide was employed and no sodium metasilicate was employed.
A 62 percent reflectance was obtained from both the control padded swatch and the padded swatch containing the fluorinated organic acid compounds of the present invention. However, following one soiling and then washing by AATCC Test Method 61, No. IIIA, equivalent to five commercial washes, the reflectance of the control padded swatch fell to 44 percent, whereas, after one soiling and washing by AATCC Test Method 61, No. 111A, the padded swatches prepared using the fluorinated organic acid compounds of the present invention had a reflectance value of 61 percent. Even after repeating the soiling and washing procedure on the padded swatches prepared in accordance with the present invention the reflectance value was 58 percent.
EXAMPLE II A qualitative, visual analysis of the difference between padded, dyed fabric swatches containing no fluorinated organic acid compound and padded, dyed fabric swatches containing the fluorinated organic acid compound of the present invention can be clearly shown. For example, employing the composition of Example l, except using benzidine yellow as the pigment, the following results were obtained:
One Soiling Two Soilings One wash & Two Dye No Soil,
Cycle Wash Cycles Composition No Wash Control Yellow, with Dirty Yellow Olive white Green striations With fluoro- Bright uni- Bright Yellow Bright chemical form yellow Yellow EXAMPLE 111 Following the procedure of Example I, a commercially available fluorochemical, representative of the types employed to impart oil and water repellency characteristics to textiles, was incorporated as the fluorochemical in the dye composition. This commercially available material is an aqueous emulsion blend of an aqueous emulsion copolymer whose major component (about 90 percent) is derived from the monomer copolymerized with a minor amount of a hydrocarbon monomer; and an aqueous emulsion hornopolymer derived from 2-ethylhexylacrylate. The proportions of these materials are in the order of about 4 percent copolymer and 9 percent hornopolymer in the blended aqueous emulsion system.
This fluorochemical composition was substituted on the basis of fluorochemical content for the perfluoroctanoyl glycine of Example I in the dye composition otherwise similar to that according to Example I and thereafter applied and tested as in Example I. The pad dyed swatches had and uneven and blotchy appearance of the applied dye and were lacking in fastness properties during laundering. Soil release properties likewise were unsatisfactory.
From the foregoing it will be seen that this invention is well adapted to obtain all of the ends and objects hereinabove set forth, together with other advantages which are obvious and which are inherent to the system. When the fluorinated acid compounds of the formula wherein each R is independently selected from H or an alkyl radical of one to eight carbon atoms and n is an integer of 6 to 18, are added to a dispersion of pigment, bonding agent and dispersing agent the appearance of dyed textile is not only improved, but also the fastness properties of the dye imparted to the textile material is improved thus rendering the dye more durable to laundering. Moreover, the compositions of the present invention also render treated fabrics more soil repellent.
If desired, known anti-soiling substances, such as aluminum silicate; preservatives, such as sodium benzoate or potassium sorbate; water-proofing agents, such as methylol stearamide and methylene-bis-stearamide; anti-static agents; heat stability additives; buffering agents, such as diarnmonium phosphate; etc. may be incorporated into the formulations of the present invention.
Obviously, many modifications and variations of the invention as hereinbefore set forth may be made without departing from the spirit and scope thereof and therefore, only such limitations should be imposed as are indicated in the appended claims.
What is claimed is:
1. A pad dyeing composition comprising a fluorinated organic acid compound and a dispersion of a pigment, bonding agent and dispersing agent said organic acid compound having the formula:
C,,F CONRCHRCOOH wherein each R is independently selected from H or an alkyl radical of one to eight carbon atoms and n is an integer of 6 to 18.
2. The composition of claim 1 wherein the dispersing agent is sodium alginate.
3. The composition of claim 2 wherein the sodium alginate is present in an effective amount, but not more than about two percent by weight.
4. The composition of claim 1 wherein the fluorinated organic acid compound is present in an amount from about 0.1 to about 5 percent by weight.
5. The composition of claim 1 wherein the pigment is present in an amount from about 0.1 to about 10 percent by weight.
6. The composition of claim 1 wherein the bonding agent is present in an amount from about 1 to about 20 percent by weight.
7. The composition of claim 1 wherein the fluorinated organic acid compound is perfluorooctanoyl glycine.
8. A method of making a pad dyeing composition comprising adding a bonding agent to a dispersion of pigment and stirring the bonding agent and pigment until a homogeneous mixture is obtained, adding dispersing agent to the homogeneous mixture of bonding agent and pigment, adjusting the mixture to a pH of at least 8, and adding a fluorinated organic acid compound to the resulting mixture, said organic acid compound having the formula:
wherein each R is independently selected from H or an alkyl radical of one to eight carbon atoms and n is an integer of 6 to 18.
9. The method of claim 8 wherein the composition containing the fluorinated organic acid compound is stirred until a homogeneous mixture is obtained.
10. The method of claim 8 wherein the fluorinated
Claims (12)
1. A pad dyeing composition comprising a fluorinated organic acid compound and a dispersion of a pigment, bonding agent and dispersing agent said organic acid compound having the formula: CnF2n 1 CONRCHRCOOH wherein each R is independently selected from H or an alkyl radical of one to eight carbon atoms and n is an integer of 6 to 18.
2. The composition of claim 1 wherein the dispersing agent is sodium alginate.
3. The composition of claim 2 wherein the sodium alginate is present in an effective amount, but not more than about two percent by weight.
4. The composition of claim 1 wherein the fluorinated organic acid compound is present in an amount from about 0.1 to about 5 percent by weight.
5. The composition of claim 1 wherein the pigment is present in an amount from about 0.1 to about 10 percent by weight.
6. The composition of claim 1 wherein the bonding agent is present in an amount from about 1 to about 20 percent by weight.
7. The composition of claim 1 wherein the fluorinated organic acid compound is perfluorooctanoyl glycine.
8. A method of making a pad dyeing composition comprising adding a bonding agent to a dispersion of pigment and stirring the bonding agent and pigment until a homogeneous mixture is obtained, adding dispersing agent to the homogeneous mixture of bonding agent and pigment, adjusting the mixture to a pH of at least 8, and adding a fluorinated organic acid compound to the resulting mixture, said organic acid compound having the formula: CnF2n 1CONRCHRCOOH wherein each R is independently selected from H or an alkyl radical of one to eight carbon atoms and n is an integer of 6 to 18.
9. The method of claim 8 wherein the composition containing the fluorinated organic acid compound is stirred until a homogeneous mixture is obtained.
10. The method of claim 8 wherein the fluorinated organic acid compound is present in an amount between 0.1 and 5 percent by weight.
11. The method of claim 10 wherein the fluorinated organic acid compound is perfluorooctanoyl glycine.
12. The method of claim 8 wherein the dye composition is diluted to 100 percent with water.
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US6531270A | 1970-08-19 | 1970-08-19 |
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US20030225178A1 (en) * | 2002-05-28 | 2003-12-04 | Alcatel | Composition comprising fluorinated, radiation-curable dyes for surface energy control |
WO2010039935A1 (en) * | 2008-10-02 | 2010-04-08 | Peach State Labs, Inc. | Compositions and methods for treating textile fibers |
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US3238235A (en) * | 1963-04-29 | 1966-03-01 | Pennsalt Chemicals Corp | Fluorinated amido carboxylic acids and salts thereof |
US3282717A (en) * | 1963-04-23 | 1966-11-01 | Kelco Co | Print paste thickener |
US3414368A (en) * | 1963-07-18 | 1968-12-03 | Teijin Ltd | Resist printing method for hydrophobic fibers |
US3576019A (en) * | 1968-08-01 | 1971-04-20 | Allied Chem | Fluorocarbon oil-repellency agents |
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US3282717A (en) * | 1963-04-23 | 1966-11-01 | Kelco Co | Print paste thickener |
US3238235A (en) * | 1963-04-29 | 1966-03-01 | Pennsalt Chemicals Corp | Fluorinated amido carboxylic acids and salts thereof |
US3414368A (en) * | 1963-07-18 | 1968-12-03 | Teijin Ltd | Resist printing method for hydrophobic fibers |
US3576019A (en) * | 1968-08-01 | 1971-04-20 | Allied Chem | Fluorocarbon oil-repellency agents |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030225178A1 (en) * | 2002-05-28 | 2003-12-04 | Alcatel | Composition comprising fluorinated, radiation-curable dyes for surface energy control |
US6844373B2 (en) | 2002-05-28 | 2005-01-18 | Alcatel | Composition comprising fluorinated, radiation-curable dyes for surface energy control |
US20050154078A1 (en) * | 2002-05-28 | 2005-07-14 | Alcatel | Composition comprising fluorinated, radiation-curable dyes for surface energy control |
US7050684B2 (en) | 2002-05-28 | 2006-05-23 | Alcatel | Composition comprising fluorinated, radiation-curable dyes for surface energy control |
WO2010039935A1 (en) * | 2008-10-02 | 2010-04-08 | Peach State Labs, Inc. | Compositions and methods for treating textile fibers |
US20100136335A1 (en) * | 2008-10-02 | 2010-06-03 | Sargent Ralph R | Compositions and methods for treating textile fibers |
AU2015207924B2 (en) * | 2008-10-02 | 2017-02-02 | Peach State Labs, Inc. | Compositions and methods for treating textile fibers |
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