US3853459A - Process for dyeing crosslinked cellulosic fabrics with disperse dyestuffs - Google Patents
Process for dyeing crosslinked cellulosic fabrics with disperse dyestuffs Download PDFInfo
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- US3853459A US3853459A US00196211A US19621171A US3853459A US 3853459 A US3853459 A US 3853459A US 00196211 A US00196211 A US 00196211A US 19621171 A US19621171 A US 19621171A US 3853459 A US3853459 A US 3853459A
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- dyed
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- 239000004744 fabric Substances 0.000 title claims abstract description 144
- 238000000034 method Methods 0.000 title claims abstract description 50
- 230000008569 process Effects 0.000 title claims abstract description 34
- 238000004043 dyeing Methods 0.000 title claims abstract description 29
- 229920000642 polymer Polymers 0.000 claims abstract description 112
- 239000000975 dye Substances 0.000 claims abstract description 57
- 229920000742 Cotton Polymers 0.000 claims description 57
- ZEYUSQVGRCPBPG-UHFFFAOYSA-N 4,5-dihydroxy-1,3-bis(hydroxymethyl)imidazolidin-2-one Chemical compound OCN1C(O)C(O)N(CO)C1=O ZEYUSQVGRCPBPG-UHFFFAOYSA-N 0.000 claims description 20
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 20
- 239000004753 textile Substances 0.000 claims description 13
- 229920002678 cellulose Polymers 0.000 claims description 10
- 239000001913 cellulose Substances 0.000 claims description 10
- 239000000178 monomer Substances 0.000 claims description 9
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 8
- 239000000835 fiber Substances 0.000 claims description 8
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 7
- 229920002994 synthetic fiber Polymers 0.000 claims description 5
- 238000010559 graft polymerization reaction Methods 0.000 claims description 4
- 239000012209 synthetic fiber Substances 0.000 claims 2
- 238000004132 cross linking Methods 0.000 abstract description 15
- 238000011282 treatment Methods 0.000 abstract description 14
- 239000003431 cross linking reagent Substances 0.000 abstract description 11
- 241000219146 Gossypium Species 0.000 description 49
- 239000000523 sample Substances 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 13
- 239000000986 disperse dye Substances 0.000 description 11
- 238000010521 absorption reaction Methods 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 10
- 230000003287 optical effect Effects 0.000 description 9
- 229920000058 polyacrylate Polymers 0.000 description 9
- 239000012153 distilled water Substances 0.000 description 8
- 229920002635 polyurethane Polymers 0.000 description 8
- 239000004814 polyurethane Substances 0.000 description 8
- XIOUDVJTOYVRTB-UHFFFAOYSA-N 1-(1-adamantyl)-3-aminothiourea Chemical compound C1C(C2)CC3CC2CC1(NC(=S)NN)C3 XIOUDVJTOYVRTB-UHFFFAOYSA-N 0.000 description 7
- VGKYEIFFSOPYEW-UHFFFAOYSA-N 2-methyl-4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound Cc1cc(ccc1O)N=Nc1ccc(cc1)N=Nc1ccccc1 VGKYEIFFSOPYEW-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 description 6
- 229920002239 polyacrylonitrile Polymers 0.000 description 6
- -1 polyethylene Polymers 0.000 description 6
- 238000013459 approach Methods 0.000 description 5
- 229920000459 Nitrile rubber Polymers 0.000 description 4
- 239000005062 Polybutadiene Substances 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 229920003048 styrene butadiene rubber Polymers 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 229920000578 graft copolymer Polymers 0.000 description 3
- 238000004900 laundering Methods 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- RTZYVAQWQXPIAC-UHFFFAOYSA-N 4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound C1=CC(O)=CC=C1N=NC1=CC=C(N=NC=2C=CC=CC=2)C=C1 RTZYVAQWQXPIAC-UHFFFAOYSA-N 0.000 description 2
- BBFRYSKTTHYWQZ-UHFFFAOYSA-N 4-anilino-3-nitro-n-phenylbenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC=2C=CC=CC=2)=CC=C1NC1=CC=CC=C1 BBFRYSKTTHYWQZ-UHFFFAOYSA-N 0.000 description 2
- 239000002174 Styrene-butadiene Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BXIGAWRFDMDLTL-UHFFFAOYSA-N n-(4-amino-3-methoxy-9,10-dioxoanthracen-1-yl)-4-methylbenzenesulfonamide Chemical compound C=12C(=O)C3=CC=CC=C3C(=O)C2=C(N)C(OC)=CC=1NS(=O)(=O)C1=CC=C(C)C=C1 BXIGAWRFDMDLTL-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000011115 styrene butadiene Substances 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 239000004758 synthetic textile Substances 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
- D06P3/8223—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups
- D06P3/8228—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using one kind of dye
- D06P3/8233—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using one kind of dye using dispersed dyes
-
- 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
- D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
- D06M14/02—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials on to materials of natural origin
- D06M14/04—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials on to materials of natural origin of vegetal origin, e.g. cellulose or derivatives thereof
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/6033—Natural or regenerated cellulose using dispersed dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/15—Locally discharging the dyes
- D06P5/17—Azo dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/22—Effecting variation of dye affinity on textile material by chemical means that react with the fibre
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/918—Cellulose textile
Definitions
- This invention relates to the dyeing of cellulosic fabties with disperse dyestuffs. More particularly this invention relates to a process which permits cotton and other cellulosic fabrics to be dyed after crosslinking.
- disperse dyestuffs have little affinity for cellulosic fabrics.
- cotton or other cellulosic containing fabric is treated with a polymer or a polymer and crosslinking agent.
- the sequence of application is unimportant. That is, the polymer can be applied either before, with or after the crosslinking agent.
- the important aspect of this treatment is that a polymer is selected for which the disperse dyestuff will have high affinity. Because the dyestuff becomes attached to the polymer which is attached to the cellulose, rather than to the cellulose directly, this provides a route for the dyeing of cotton fabrics which is independent'of the degree of crosslinking of the cellulose. Because of this, a cotton or blended fabric can be readily dyed either before or after crosslinking.
- the process variables can be easily worked out by one knowledgeable in the textile field. Some variations of this process are asfollows.
- polymer-and crosslinking agent are applied to fabric and the fabric is raised to durablepress or wash-wear performance standards.
- the polymer can be applied before, with, or after the crosslinking agent.
- peripheral fibers of the fabric with the 47% fiber add-on were deeply dyed thus indicating that 4 accessibility is the major factor in the poor dyeing of the fabric. Perhaps, a very loosely woven fabric such as a knit would dye satisfactorily with a 47% add-on.
- the next step consists of the application of the disperse dyestuff to the fabric.
- the method most commonly employed in this work was placing the disperse dyestuff in a bath,and heating the fabric at an elevated temperature in the dyebath containing the disperse dyestuff. Because crosslinking finishes are sensitive to bath pH at higher temperatures, an important consideration is to use dyestuffs and baths which can be adjusted close to pI-I 7 if necessary.
- thermosol method is a high temperature fixation method frequently employed with synthetic fabrics. While the nature of the polymers utilized in this work are such that dye bath techniques would seem to be preferred, use of the thermosol type application using dyestuffs with low sublimation characteristics should be possible. In particular, this method should be appropriate with blended fabrics, in which the synthetic component may be dyed most easily using the thermosol process.
- Dye uptake increases progressively as the amount of polymer applied to the fabric is increased.
- An effective area of polymer application is from 4-20% with the preferred range being from 7-15% taking into consideration such variables as effectiveness, fabric hand, cost and other factors influencing fabric use.
- optical brightener normally used on synthetic fabrics or an optical brightener having the characteristics of a disperse dyestuff to whiten polymer treated and crosslinked fabrics.
- the process is analogous to the method employed with the disperse dyestuff except of course that optical brighteners are more temperature sensitive and as such the temperature range of the bath containing the brightener is lower than in normal dye bath temperatures.
- the absorption of the brightener by the fabrics can be noted in three ways.
- crosslinked fabric with polymer to absorb brightener is important because conventionally crosslinked fabrics show poor absorption of optical brightener. As such, fabrics so treated tend to become textile art.
- EXAMPLE I A sample of cotton printcloth and a sample of 50% polyester-50% cotton cloth were treated with a water solution containing 9% dimethylol dihydroxyethyleneurea and 0.6% zinc nitrate hexahydrate. These fabrics were then dried for 7 minutes at 60 C and cured for 15 minutes at 130 C. The fabrics were then given a wash-wear wash and tumbled dry. Samples of these fabrics as well as the untreated cotton and blended fabric were treated with a polymer emulsion containing 8% polyurethane (of low glass transition temperature). The fabrics were then dried for 7 minutes at 60 C and cured for l0 minutes at l40 C. The fabrics were laundered.
- EXAMPLE 2 Undyed samples from Example 1 were dyed at 90l00 C for a period of 30 minutes in a bath containing 1% Disperse Yellow 88. The samples were rinsed in distilled water and laundered. All of the polymer treated samples were dyed a deep yellow while the samples with no polymer on them were relatively undyed. This example demonstrates that the presence of polymer permits both cotton and blended fabrics to be dyed with disperse dyes. The dye uptake was equally good on both the crosslinked and noncrosslinked polymer treated fabrics. This indicates that the process is independent of the degree of crosslinking of the cotton. The only necessary requirement was for a suitable polymer to be on the fabric.
- EXAMPLE 3 Undyed samples from Example 1 were dyed at 90l00 C for a period of 30 minutes in a bath containing 1% Disperse Yellow 42. The samples were then rinsed in distilled water and laundered. All of the polymer treated samples were dyed a deep yellow while the samples with no polymer on them were relatively undyed.
- EXAMPLE 4 A sample of cotton printcloth and a sample of 50% polyester-50% cotton cloth were treated with a water solution containing 9% dimethylol dihydroxyethyleneurea and 0.6% zinc nitrate hexahydrate. These fabrics were dried for 7 minutes at 60 C and cured for minutes at 130 C. The fabrics were given a wash wear wash and tumbled dry. Samples of these fabrics as well as the untreated cotton and blended fabric were then treated with a polymer emulsion containing 8% butadiene-acrylonitrile copolymer. The fabrics were dried for 7 minutes at 60 C and cured for 10 minutes at 140 C. The fabrics were then laundered.
- Example 5 Undyed samples from Example 4 were dyed at 90l00 C for a period of 30 minutes in a bath containing 1% Disperse Yellow 88. The samples were rinsed in distilled water and laundered. All of the polymer treated samples were dyed a deep yellow while the samples with no polymer on them were relatively undyed. This example demonstrates that the presence of polymer permits both cotton and blended fabrics to be dyed with disperse dyes. The dye uptake was equally good on both the crosslinked and noncrosslinked polymer treated fabrics. This indicates that the process is independent of the degree of crosslinking of the cotton. The only necessary requirement was for a suitable polymer to be on the fabric.
- EXAMPLE 6 Undyed samples from Example 4 were dyed at 90l00 C for'a period of 30 minutes in a bath containing 1% Disperse Yellow 42. The samples were rinsed in distilled water and laundered. All of the polymer treated samples were dyed a deep yellow while the samples withno polymer on them were relatively undyed. This example demonstrates that the presence of polymer permits both cotton and blended fabrics to be dyed with disperse dyes. The dye uptake was equally good on both the crosslinked and noncrosslinked polymer treated'fabrics. Theonly necessary requirement was for a suitable polymer to be on the fabric.
- EXAMPLE 7 An untreated cotton basket weave fabric was padded with a solution containing 12% polyurethane. The fabric was dried for 7 minutes at 60 C and cured for l0 minutes at 150 C. Another untreated cotton basket weave was given a similar treatment using 12% polyacrylate. A third sample was given a similar treatment using a butadiene-acrylonitrile copolymer. All of these samples plus an additional untreated cotton sample were padded with a solution containing 7.2% dimethylol dihydroxyethyleneurea and 0.6% zinc nitrate hexahydrate. These fabrics were dried for 7 minutes at 60 1 C and cured for 15 minutes at 130 C. They were laundered and tumbled dry.
- EXAMPLE 8 An untreated cotton basket weave fabric was padded with a solution containing 12% polybutadiene. The fabric was dried for 7 minutes at 60 C and cured for 10 minutes at 150 C. This sample was padded with a solution containing 7.2% dimethylol dihydroxyethyleneurea and 0.6% zinc nitrate hexahydrate. The fabric was dried for 7 minutes at 60 C and cured for 15 minutes at C. It was laundered and tumbled dry. This sample plus undyed samples from'Example 7 plus the same samples treated with polymer but without crosslinking agent were dyed at 90l00 C for a period of 25 minutes in a bath containing 1% Disperse Yellow 88. The samples were rinsed in distilled water and extracted with a hot water bath.
- the untreated cotton and crosslinked cotton control were undyed.
- the sample treated with polybutadiene was slightly dyed. All of the other polymer treated samples were dyed a deep yellow to orange. This example again deomonstrates that the dyeing system is effective whether or not the cotton is crosslinked.
- the poor dyeing characteristics of the sample treated with a polybutadiene indicates the character of the polymer is an important factor in whether or not the fabrics can be dyed with a disperse dye.
- EXAMPLE 9 An untreated cotton basket weave fabric was padded 6% of a polyacrylonitrile. The fabrics were dried for 7 minutes at 60 C. A second pair of samples were given a similar treatment using 12% of a polyacrylonitrile. One of the fabrics treated with each level of polymer plus an untreated cotton were padded with 8.1% dimethylol dihydroxyethyleneurea and 0.5% zinc nitrate hexahydrate. The fabrics were dried for 7 minutes at 60 C and cured for 10 minutes at 130 C. The samples were laundered and tumbled dry. Samples of each of these fabrics plus an untreated cotton were then dyed with 1% Disperse Yellow 88 as in Example 9. The fabrics with the polyacrylonitrile on them were dyed a bright yellow.
- Copolymer 'DMDl-IEU dimethylol dihydroxycthylencurca larly the samples treated with polyethylene were a very light beige. By contrast the samples treated with polyurethane or silicone were a moderately deep yellow while the samples treated with a polyacrylate were a bright yellow. About equivalent dye uptake was shown by both the crosslinked and noncrosslinked-sarnples treated with the same polymer.
- EXAMPLE 12 A sample of cotton fabric was placed in a nitrogen saturated solution containing 2% methyl acrylate, 0.09% ceric ammonium nitrate, 0.63% nitric acid, and 97.28% water. The sample was allowed to remain in the solution for 30 minutes. After laundering the fabric had an add-on of 47%.
- Another sample of cotton fabric was placed in a nitrogen saturated solution containing 5% acrylamide, 0.1 1% ceric ammonium nitrate, 0.63% nitric acid, and 94.26% water. The sample was allowed to react at 25 C for 80 minutes. After laundering the sample had a 5% add-on.
- a sample of cotton fabric was placed in a nitrogen saturated solution containing 4% acrylonitrile, 0.27% ceric ammonim nitrate, 0.63% nitric acid, and 95.1% water. The sample was allowed to remain in the solution at 25 C for 30 minutes, after which time the sample was laundered. The sample had an add-on of 27%.
- a process for applying a disperse dyestuff to a cellulose fabric having poor affinity for said dyestuff which process consists of installing a polymer selected from the group consisting of polymerized methyl acrylate and polymerized. acrylamide onthe fiber surfaces ofthe cellulose fabric, said polymer being installed via graft polymerization employing the counterpart monomer, and subsequently dyeing the cellulose witha disperse dyestuff.
- a process for dyeing with a disperse dyestuff a crosslinked cellulosic textile fabric having poor affinity for said dyestuff, said fabric selected from the group consisting of a cotton fiber textile fabric crosslinked by dimethylol dihydroxyethyleneurea and a cotton fibersynthetic fiber blended textile fabric crosslinked by dimethylol dihydroxyethyleneurea, which process consists-of installing on the fiber surfaces of the fabric a polymer selected from the group consisting of polymerized methyl acrylate and polymerized acrylamide, said polymer being installed via graft polymerization employing the counterpart monomer, and subsequently blended textile fabric.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Coloring (AREA)
Abstract
A process has been developed for the dyeing of subsequent to crosslinking, it also allows cellulosic fabrics to be dyed with disperse dyestuffs. This process consists of the treatment of a fabric with crosslinking agent and a suitable polymer. This was followed by dyeing the fabric with a disperse dyestuff. In addition to permitting cellulosic fabrics to be dyed subsequent to crosslinking, it also allows cellulosic fabrics to be dyed with disperse dyestuffs. The latter is important because it permits blended fabrics to be dyed with a single class of dye under relatively mild conditions.
Description
United States Patent 1191 Harper, Jr. et al.
[ PROCESS FOR DYEING CROSSLINKED CELLULOSIC FABRICS WITH DISPERSE DYESTUFFS [73] Assignee: The United States of America as represented by the United States Department of Agriculture,
Washington, DC.
1221 Filed: Nov. 5, 1971 211 Appl. N0.2 l96,21l
[52] U.S. Cl 8/18, 8/31, 8/100, 117/15,117/62 [51] Int. Cl D06p 1/76 [58] Field of Search 8/31, l8, 17; 117/13; 156/178, 76 T [56] 7 References Cited UNITED STATES PATENTS 2,865,872 12/1958 Hagemeyer et a1 8/DIG. 18
[ 1' Dec. 10, 1974 3,097,960 7 1963 Lawton 6! a1 8/D1G. l8 3,138,431 6/1964 Swiggett 8/ll5.5 3,184,421 5/1965 Caldwell et al. 8/010. 18 3,281,263 10/1966 Priesing 8/DIG. 18 3,508,854 4/1970 SOkOl 8/18 Primary Examiner-Donald Levy Attorney, Agent, or Firm-M. Howard Silverstein; Max D. Hensley 57 ABSTRACT A process has been developed for the dyeing of subsequent to crosslinking, it also allows cellulosic fabrics to be dyed with disperse dyestuffs. This process consists of the treatment of a fabric with crosslinking agent and a suitable polymer. This was followed. by dyeing the fabric witha disperse dyestuff.
In addition to permitting cellulosic fabrics to be dyed subsequent to crosslinking, it also allows cellulosic fabrics to be dyed with disperse dyestuffs. The latter is important because it permits blended fabrics to be dyed with a single class of dye under relatively mild conditions.
7 Claims, I No Drawings 'of America.
PROCESS FOR DYEING CROSSLINKED CELLULOSIC FABRICS WITH DISPERSE DYESTUFFS A non-exclusive, irrevocable, royalty-free license in the invention herein described, throughout the world for all purposes of the United States Government, with the power to grant sublicenses for such purposes, is hereby granted to the Government of the United States This invention relates to the dyeing of cellulosic fabties with disperse dyestuffs. More particularly this invention relates to a process which permits cotton and other cellulosic fabrics to be dyed after crosslinking. Heretofor, it is well known that disperse dyestuffs have little affinity for cellulosic fabrics. Likewise, it is well known that only limited systems exist for the dyeing of crosslinked cellulosic fabrics.
In this process, cotton or other cellulosic containing fabric is treated with a polymer or a polymer and crosslinking agent. The sequence of application is unimportant. That is, the polymer can be applied either before, with or after the crosslinking agent. The important aspect of this treatment is that a polymer is selected for which the disperse dyestuff will have high affinity. Because the dyestuff becomes attached to the polymer which is attached to the cellulose, rather than to the cellulose directly, this provides a route for the dyeing of cotton fabrics which is independent'of the degree of crosslinking of the cellulose. Because of this, a cotton or blended fabric can be readily dyed either before or after crosslinking. The latter instance is particularly important because heretofore all smooth drying techniques drastically reduced the affinity of cotton fabrics for dyestuffsThis method is important because it permits flexability in inventory controls, that is, fabric can be completely finished except for dyeing. When an order for a particular color is obtained, this fabric can then be dyed and shipped out. Second, cotton fiber whether crosslinked or not normally has poor affinity for disperse dyestuffs. By this method cotton fabrics can be obtained that are dyed with a whole new class of dyestuffs. Another advantage is that in current practice cotton is dyed prior to crosslinking. However, dye sublimation, shade change and reduced lightfastness are frequently encountered due to the action of the second. The harmful effects of high temperature cures and of the crosslinking agents and catalysts on the dyestuff are thereby eliminated.
While a number of polymers and copolymers have been used in finishing prior to dyeing only those with relatively low functionality such as polyethylene perform poorly. Polybutadiene is only slightly better. Silicones have shown variable performance, being satisfactory with some dyes and unsatisfactory with others. Both polyacrylates and polyurethanes are moderately effective and give satisfactory take-up of disperse dyes in dyeing experiments. Particularly effective are polymers and copolymers containing acrylonitrile as a monomer. An example of this type is the butadieneacrylonitrile copolymer. Dye uptake seems to increase with increasing acrylonitrile content in the polymer, so that, polyacrylonitrile is particularly effective.
Numerous polymers are available to promote dye uptake. It is only necessary to select those which possess the desired functionality or chemical groups that when used in fibers have shown good affinity. for disperse dyes. Some groups which are particularly effective are copolymers in which an acrylonitrile moiety (A) is present and those in which a urethane (B) or amide (C) type linkage is formed. Acrylate copolymers likewise'have shown good performance as well as butadiene-styrene copolymers.
From a practical point of view, polymers with glass transition temperatures below room temperature would appear to be most suitable. Dye uptake can be achieved with polymersof high glass transition temperature-but the high polymer add-ons required in this process leads to fairly stiff fabrics.
Once the requirement for the dye acceptability of the polymer becomes recognized, the process variables can be easily worked out by one knowledgeable in the textile field. Some variations of this process are asfollows. In the initial step, polymer-and crosslinking agent are applied to fabric and the fabric is raised to durablepress or wash-wear performance standards. In the first step, the polymer can be applied before, with, or after the crosslinking agent. The polymer .canbe applied either as an emulsion or from solvent.
Another means of polymer treatment has been achieved when a monomer or polymer is applied to fabric and the monomer is polymerized to give a polymer treated fabric with the desired affinity for dispersedyestuffs. Examples of monomersused in this work were acrylonitrile, acrylamide and methyl acrylate.
There are two basic differences in the approach based upon monomer grafting versus the approach based upon deposition of preformed polymers. First, monomer grafting is a much more intimate reaction with the cellulose substrate. As such, a balance has to be achieved between sufficient grafted polymer to give good dye absorption and so much polymer graft that accessability of the dye to the fiber is hindered. By way of example, methyl acrylate was reacted on cotton to the extent of 16, 27 and 47%. The fabric was then crosslinked and dyed with disperse dyestuffs. The best dyestuff absorption was displayed ,by the fabric with 27% polymer add-on, the next with 16% and the fabric with 47% add-on showed relatively poor dyestuff absorption. The peripheral fibers of the fabric with the 47% fiber add-on were deeply dyed thus indicating that 4 accessibility is the major factor in the poor dyeing of the fabric. Perhaps, a very loosely woven fabric such as a knit would dye satisfactorily with a 47% add-on.
The second characteristic encountered in this work was that grafted and crosslinked fabrics frequently showed substantially better or poorer dye absorption than fabric which was grafted only. This difference in grafted fabrics is much greater than the same differ ence (between polymer coated and crosslinked and polymer coated only) in the case in which the preformed polymer is deposited on the fabric.
Once this initial phase of polymer treatment is accomplished, the next step consists of the application of the disperse dyestuff to the fabric. The method most commonly employed in this work was placing the disperse dyestuff in a bath,and heating the fabric at an elevated temperature in the dyebath containing the disperse dyestuff. Because crosslinking finishes are sensitive to bath pH at higher temperatures, an important consideration is to use dyestuffs and baths which can be adjusted close to pI-I 7 if necessary.
In addition to dye bath techniques, other methods usually employed with disperse dyestuffs can also be used. One such method is the thermosol method, which is a high temperature fixation method frequently employed with synthetic fabrics. While the nature of the polymers utilized in this work are such that dye bath techniques would seem to be preferred, use of the thermosol type application using dyestuffs with low sublimation characteristics should be possible. In particular, this method should be appropriate with blended fabrics, in which the synthetic component may be dyed most easily using the thermosol process.
While this method covers only the cases of dyeing subsequent to crosslinkingflt should be realized that other variations are possible. In particular, the application of the polymer to synthetic fabric blends such as polyester-cotton or polyester-rayon followed by dyeing at this point appears to be particularly beneficial. It is well known that such blended fabrics require dyeing by two classes of dyes, one for the dyeing of the polyester component, the other for dyeing of the cellulosic component. This entails considerable processing and com-- paratively high dye costs. By contrast, polymer treated blended fabrics can be dyed with a single dye system with the accompanying reduction in processing costs. Of course, the other variation of the application of polymer and crosslinking agent to produce a durablepress fabric followed by dyeing likewise is effective. The advantage of this approach is threefold. First it permits blended fabrics to be dyed using a single class of dye. Second, it permits such blended fabrics to be dyed subsequent to crosslinking. Finally, dye uptake is much more rapid than on nonpolymer treated fabrics.
Similar treatments of all-cotton fabrics with polymer only makes such fabrics potentially dyeable with disperse dyestuffs.
To this point, little consideration has been given to how much polymer is required for these treatments. Dye uptake increases progressively as the amount of polymer applied to the fabric is increased. An effective area of polymer application is from 4-20% with the preferred range being from 7-15% taking into consideration such variables as effectiveness, fabric hand, cost and other factors influencing fabric use. By use of a polymer with higher dye affinity, the lower end of the polymer concentration range can be used and conversely, with polymers with lower dye affinities, polymer concentration at the higher end of the dye range may be necessary.
Another extension of this general approach has also been developed. This consists of using an optical brightener normally used on synthetic fabrics or an optical brightener having the characteristics of a disperse dyestuff to whiten polymer treated and crosslinked fabrics. The process is analogous to the method employed with the disperse dyestuff except of course that optical brighteners are more temperature sensitive and as such the temperature range of the bath containing the brightener is lower than in normal dye bath temperatures.
Once the polymer treated fabrics have been exposed to the bath containing optical brightener, the absorption of the brightener by the fabrics can be noted in three ways. First, the samples treated with polymer and crosslinking agent are whiter than those treated with polymer only or which are untreated. Second, inspection of the various samples under UV light reveals the fact that the polymer treated samples are white under UV light while the nonpolymer treated samples are grey.
In addition to the observation of improved optical brightener absorption and hence fabric whiteness under either regular or UV light, a method has been developed to measure the relative improvement in absorptionof brightener by the polymer treated fabrics. In this method, a series of fabrics including an untreated cotton, a crosslinked cotton without polymer, and crosslinked cottons with various polymers is placed in a bath containing optical brightener for a period of time. The samples are then laundered. The fluorescence of thses samples is measured at the maximum corresponding to optical brightener fluorescence. The values are expressed on a percentage basis with one of the polymer treated cottons given the arbitrary value of 100%. Under these conditions, the crosslinked cotton had a value of 12%, the untreated cotton 18% and the crosslinked cotton samples with other polymers had values ranging from 73 to 151%.
In addition to the dye bath technique described, other standard methods for adding brightener such as laundering with a wash solution containing brightener or padding with a solution containing brightener should also be applicable.
The ability of crosslinked fabric with polymer to absorb brightener is important because conventionally crosslinked fabrics show poor absorption of optical brightener. As such, fabrics so treated tend to become textile art.
EXAMPLE I A sample of cotton printcloth and a sample of 50% polyester-50% cotton cloth were treated with a water solution containing 9% dimethylol dihydroxyethyleneurea and 0.6% zinc nitrate hexahydrate. These fabrics were then dried for 7 minutes at 60 C and cured for 15 minutes at 130 C. The fabrics were then given a wash-wear wash and tumbled dry. Samples of these fabrics as well as the untreated cotton and blended fabric were treated with a polymer emulsion containing 8% polyurethane (of low glass transition temperature). The fabrics were then dried for 7 minutes at 60 C and cured for l0 minutes at l40 C. The fabrics were laundered. Samples of these fabrics plus appropriate controls were then dyed at l00 C for a period of 20 minutes in a bath containing l% Disperse Yellow 23. The samples were rinsed in distilled water and laundered. All of the polymer treated samwith no polymer on them were very slightly dyed. This example shows that the presence of polymer permits both cotton and blended fabrics to be dyed with disperse dyes. The dye uptake was good and about equivalent on both the crosslinked and noncrosslinked fabrics. The only requirement was for the polyurethane to be present on the fabric.
EXAMPLE 2 Undyed samples from Example 1 were dyed at 90l00 C for a period of 30 minutes in a bath containing 1% Disperse Yellow 88. The samples were rinsed in distilled water and laundered. All of the polymer treated samples were dyed a deep yellow while the samples with no polymer on them were relatively undyed. This example demonstrates that the presence of polymer permits both cotton and blended fabrics to be dyed with disperse dyes. The dye uptake was equally good on both the crosslinked and noncrosslinked polymer treated fabrics. This indicates that the process is independent of the degree of crosslinking of the cotton. The only necessary requirement was for a suitable polymer to be on the fabric.
EXAMPLE 3 Undyed samples from Example 1 were dyed at 90l00 C for a period of 30 minutes in a bath containing 1% Disperse Yellow 42. The samples were then rinsed in distilled water and laundered. All of the polymer treated samples were dyed a deep yellow while the samples with no polymer on them were relatively undyed.
This example demonstrates that the presence of polymer permits both cotton and blended fabrics to be dyed with disperse dyes. The dye uptake was equally good on both the crosslinked and noncrosslinked polymer treated fabrics. The only necessary requirement was for a suitable polymer to be on the fabric.
EXAMPLE 4 A sample of cotton printcloth and a sample of 50% polyester-50% cotton cloth were treated with a water solution containing 9% dimethylol dihydroxyethyleneurea and 0.6% zinc nitrate hexahydrate. These fabrics were dried for 7 minutes at 60 C and cured for minutes at 130 C. The fabrics were given a wash wear wash and tumbled dry. Samples of these fabrics as well as the untreated cotton and blended fabric were then treated with a polymer emulsion containing 8% butadiene-acrylonitrile copolymer. The fabrics were dried for 7 minutes at 60 C and cured for 10 minutes at 140 C. The fabrics were then laundered. Samples of these fabrics plus appropriate controls were dyed at 90l00 C for a period of minutes in a bath containing 1% Disperse Yellow 23. The samples were rinsed in distilled water and laundered. All of the polymer treated samples were dyed a deep orange-yellow while the samples with no polymer on them were very slightly dyed. This example shows that the presence of polymer permits both cotton and blended fabrics to be dyed with disperse dyes. The dye uptake was good on both the crosslinked and noncrosslinked fabrics. The only requirement was for the butadiene-acrylonitrile copolymer to be present. I
' EXAMPLE 5 Undyed samples from Example 4 were dyed at 90l00 C for a period of 30 minutes in a bath containing 1% Disperse Yellow 88. The samples were rinsed in distilled water and laundered. All of the polymer treated samples were dyed a deep yellow while the samples with no polymer on them were relatively undyed. This example demonstrates that the presence of polymer permits both cotton and blended fabrics to be dyed with disperse dyes. The dye uptake was equally good on both the crosslinked and noncrosslinked polymer treated fabrics. This indicates that the process is independent of the degree of crosslinking of the cotton. The only necessary requirement was for a suitable polymer to be on the fabric.
EXAMPLE 6 Undyed samples from Example 4 were dyed at 90l00 C for'a period of 30 minutes in a bath containing 1% Disperse Yellow 42. The samples were rinsed in distilled water and laundered. All of the polymer treated samples were dyed a deep yellow while the samples withno polymer on them were relatively undyed. This example demonstrates that the presence of polymer permits both cotton and blended fabrics to be dyed with disperse dyes. The dye uptake was equally good on both the crosslinked and noncrosslinked polymer treated'fabrics. Theonly necessary requirement was for a suitable polymer to be on the fabric.
EXAMPLE 7 An untreated cotton basket weave fabric was padded with a solution containing 12% polyurethane. The fabric was dried for 7 minutes at 60 C and cured for l0 minutes at 150 C. Another untreated cotton basket weave was given a similar treatment using 12% polyacrylate. A third sample was given a similar treatment using a butadiene-acrylonitrile copolymer. All of these samples plus an additional untreated cotton sample were padded with a solution containing 7.2% dimethylol dihydroxyethyleneurea and 0.6% zinc nitrate hexahydrate. These fabrics were dried for 7 minutes at 60 1 C and cured for 15 minutes at 130 C. They were laundered and tumbled dry. Samples of these fabrics were dyed at l00 C for a period of 30 minutes in a bath containing 1% Disperse Red 86. All of the samples were dyed a deep red except for the crosslinked cotton control. This sample was dyed a light pink. This example demonstrates that the presence of various polymers on crosslinked fabrics permits these fabrics to be dyed subsequent to crosslinking provided that disperse dyes are used for dyeing.
EXAMPLE 8 An untreated cotton basket weave fabric was padded with a solution containing 12% polybutadiene. The fabric was dried for 7 minutes at 60 C and cured for 10 minutes at 150 C. This sample was padded with a solution containing 7.2% dimethylol dihydroxyethyleneurea and 0.6% zinc nitrate hexahydrate. The fabric was dried for 7 minutes at 60 C and cured for 15 minutes at C. It was laundered and tumbled dry. This sample plus undyed samples from'Example 7 plus the same samples treated with polymer but without crosslinking agent were dyed at 90l00 C for a period of 25 minutes in a bath containing 1% Disperse Yellow 88. The samples were rinsed in distilled water and extracted with a hot water bath. The untreated cotton and crosslinked cotton control were undyed. The sample treated with polybutadiene was slightly dyed. All of the other polymer treated samples were dyed a deep yellow to orange. This example again deomonstrates that the dyeing system is effective whether or not the cotton is crosslinked. The poor dyeing characteristics of the sample treated with a polybutadiene indicates the character of the polymer is an important factor in whether or not the fabrics can be dyed with a disperse dye.
EXAMPLE 9 An untreated cotton basket weave fabric was padded 6% of a polyacrylonitrile. The fabrics were dried for 7 minutes at 60 C. A second pair of samples were given a similar treatment using 12% of a polyacrylonitrile. One of the fabrics treated with each level of polymer plus an untreated cotton were padded with 8.1% dimethylol dihydroxyethyleneurea and 0.5% zinc nitrate hexahydrate. The fabrics were dried for 7 minutes at 60 C and cured for 10 minutes at 130 C. The samples were laundered and tumbled dry. Samples of each of these fabrics plus an untreated cotton were then dyed with 1% Disperse Yellow 88 as in Example 9. The fabrics with the polyacrylonitrile on them were dyed a bright yellow. By contrast, those without any polymer on them were off-white. The excellent shade of yellow achieved on both the noncrosslinked and crosslinked with a solution containing 12% polyethylene. The fab- 15 Sam ples with only 6% polyacrylonitrile on them indiwas f gz i atl60 C i T; s cates the effectiveness of thisv type of polymer in this 2 2:5233 h i r l g z z i ai g ig process. Similar results were also obtained except that thyleneurea and 0.6% zinc nitrate hexahydrate. A simithe g i g y g p g the fagncs lar treatment sequence was also applied to another fabwere ye Sparse ue usmg e proce ric except that 12% silicone rather than 12% polyethyldescnbed m Example ene was used-as the polymer. These fabrics were dried EXAMPLE i 1 for 7 minutes at 60 C and cured for 15 minutes at 130 C. They were laundered and tumbled dry. These sam- A Sample: of q p l was treated Wlth ples plus undyed Samples f Example 7 plus appm water solution containing 9% d1methylol dihydroxyepriate controls treated with only the polymer or crossthylerneufea and 07% Zmc "mate hexahydrate- Thls linking agent were d ed at 90-100 C f a period of fabric was then dried for 7 minutes at 60 C and cured minutes in a bath containing 1% Disperse Yellow 88 for 15 minutes at 130 C. Other samples were given a and then laundered. 30 similar treatment. In these cases, the padding mixtures The untreated cotton sample and crosslinked control contained crosslinking agent, catalyst and polymer as (without polymer) showed very little dye uptake. Similisted in Table l. The fabrics were laundered,
TABLE I Sample Zinc Nitrate No. Polymer Type Polymer DMDHEU Hex-ahydrate l Polyacrylate 5 6.8 0.6 2 Polyacrylate 8 6.8 0.6 3 Polyurethane 8 6.8 0.6 4 Nitrile Copolymer 5 6.8 0.6 5 Nitrile Copolymer 8 6.8 0.6 6 Styrene-butadiene 5 6.8 0.6
Copolymer 7 Styrene-butadiene 8 6.8 0.6
Copolymer 'DMDl-IEU dimethylol dihydroxycthylencurca larly, the samples treated with polyethylene were a very light beige. By contrast the samples treated with polyurethane or silicone were a moderately deep yellow while the samples treated with a polyacrylate were a bright yellow. About equivalent dye uptake was shown by both the crosslinked and noncrosslinked-sarnples treated with the same polymer.
Undyecl samples were dyed in a similar fashion with Disperse Blue 79 except that the dye period was 30 minutes. Results were comparable to the preceding case, namely, the untreated and polyethylene treated samples and their crosslinked counterparts showed poor uptake. The polyacrylate treated samples showed excellent absorption, the polyurethane treated samples showed good absorption andthe silicone treated samples showed only marginal absorption. These results demonstrate that not all polymers are suitable for this process but only those with functional moieties.
EXAMPLE 10 Two samples of cotton printcloth were padded with Small'samples of these fabrics were immersed in a bath containing 0.8% of a disperse brightener (Phorwite EBL) for a period of 30 minutes at 50-60 C. The samples were rinsed 10 times in distilled water and laundered. The polymer treated samples were whiter under both regular light and UV light than the nonpolymer treated samples. The fluorescence values of these samples were measured using a Farrard Spectrofluorometer at the maximum for this disperse brightener,
which occurs at 450 mg. The optical density readings TABLE II Sample Relative No. Treatment Fluorescence 1 Polyacrylate and DMDHEU 100 2 8% Polyacrylate and DMDHEU 84 g 3 8% Polyurethane and DMDHEU 73 4 5% Nitrile Copolymer and DMDHEU 129 5 8% Nitrile Copolynier and DMDHEU 151 6 5% Styrene-butadiene Copolymer 86 and DMDHEU 7 8% Styrene-butadiene Copolymer l 12 and DMDHEU DMDHEU 12 8 9 Untreated Cotton 18 DMDHEU dimethylol dihydroxyethyleneurea All of these results clearly indicate the validity of an approach based upon polymer treatment followed by application of a bath containing a brightener having the characteristics of a disperse dyestuff as a means of whitening cellulosic fabrics.
EXAMPLE 12 A sample of cotton fabric was placed in a nitrogen saturated solution containing 2% methyl acrylate, 0.09% ceric ammonium nitrate, 0.63% nitric acid, and 97.28% water. The sample was allowed to remain in the solution for 30 minutes. After laundering the fabric had an add-on of 47%.
Similar experiments were conducted in which the reaction time was reduced to 15 minutes and 7.5 minutes. Add-on of grafted polymer in these cases was 27% and 16% respectively.
Another sample of cotton fabric was placed in a nitrogen saturated solution containing 5% acrylamide, 0.1 1% ceric ammonium nitrate, 0.63% nitric acid, and 94.26% water. The sample was allowed to react at 25 C for 80 minutes. After laundering the sample had a 5% add-on.
A sample of cotton fabric was placed in a nitrogen saturated solution containing 4% acrylonitrile, 0.27% ceric ammonim nitrate, 0.63% nitric acid, and 95.1% water. The sample was allowed to remain in the solution at 25 C for 30 minutes, after which time the sample was laundered. The sample had an add-on of 27%.
A similar reaction was conducted with 50-50% cotton-polyester fabric'except that 0.135% ceric ammonium nitrate was used. ln this case the fabric had an add-on of 10%. v
Half of each of these grafted samples and an untreated cotton sample were padded with a solution containing 8.1% dimethylol dihydroxyethyleneurea and 0.5% zinc nitrate hexahydrate and the remainder water. The samples were dried for 7 minutes at 60 C. and cured for 15 minutes at 130 C. Samples of each of these fabrics (crosslinked and noncrosslinked) were immersed in a dye bath containing 1% Disperse Yellow 88 for a period of 1 hour at -90 C. The samples were rinsed and laundered. The samples with the grafted groups were dyed yellow while the untreated samples and crosslinked samples were relatively undyed. In the case of the samples with the methyl acrylate graft, the samplewith 27% acrylate polymer addon was the deepest yellow, the one with 16% polymer add-on was next and the sample with 47% polymer addon was poorly dyed. 1n the case of the samples with the polyacrylonitrile or polyacrylamide grafts, the crosslinked samples were dyed a deeper shade of yellow than the noncrosslinked. Samples were also dyed in a similar fashion using Disperse Blue 79 and Disperse Red 86. In each case, the samples with the grafted polymers were dyed red and blue respectively while those without polymer were relatively undyed. These results indicate that polymer grafting, crosslinking and then dyeing with disperse dyes provide another route by which cotton and other cellulosic fabrics can be dyed subsequent to crosslinking.
We claim:-
1. A process for applying a disperse dyestuff to a cellulose fabric having poor affinity for said dyestuff, which process consists of installing a polymer selected from the group consisting of polymerized methyl acrylate and polymerized. acrylamide onthe fiber surfaces ofthe cellulose fabric, said polymer being installed via graft polymerization employing the counterpart monomer, and subsequently dyeing the cellulose witha disperse dyestuff.
2. The process of claim 1 wherein the polymer is polymerized methyl acrylate.
3. The process of claim 1 wherein the polymer is polymerized acrylamide.
4. The process of claim 1 wherein the polymer is polymerized acrylonitrile.
5. A process for dyeing with a disperse dyestuff a crosslinked cellulosic textile fabric having poor affinity for said dyestuff, said fabric selected from the group consisting of a cotton fiber textile fabric crosslinked by dimethylol dihydroxyethyleneurea and a cotton fibersynthetic fiber blended textile fabric crosslinked by dimethylol dihydroxyethyleneurea, which process consists-of installing on the fiber surfaces of the fabric a polymer selected from the group consisting of polymerized methyl acrylate and polymerized acrylamide, said polymer being installed via graft polymerization employing the counterpart monomer, and subsequently blended textile fabric.
Claims (7)
1. A PROCESS FOR APPLYING A DISPERSE DYSTUFF TO A CELLULOSE FABRIC HAVING POOR AFFINITY FOR SAID DRYSTUFF, WHICH PROCESS CONSISTS OF INSTALLING A POLYMER SELECTED FROM THE GROUP CONSISTING OF POLYMERIZED METHYL ACRYLATE AND POLYMERIZED ACRYLAMIDE ON THE FIBER SURFACES OF THE CELLULOSE FABRIC, SAID POLYMER BEING INSTALLED VIA GRAFT POLYMERIZATION EMPLOYING THE COUNTERPART MONOMER, AND SUBSEQUENTLY DYEING THE CELLULOSE WITH A DISPERSE DYESTUFF.
2. The process of claim 1 wherein the polymer is polymerized methyl acrylate.
3. The process of claim 1 wherein the polymer is polymerized acrylamide.
4. The process of claim 1 wherein the polymer is polymerized acrylonitrile.
5. A process for dyeing with a disperse dyestuff a crosslinked cellulosic textile fabric having poor affinity for said dyestuff, said fabric selected from the group consisting of a cotton fiber textile fabric crosslinked by dimethylol dihydroxyethyleneurea and a cotton fiber-synthetic fiber blended textile fabric crosslinked by dimethylol dihydroxyethyleneurea, which process consists of installing on the fiber surfaces of the fabric a polymer selected from the group consisting of polymerized methyl acrylate and polymerized acrylamide, said polymer being installed via graft polymerization employing the counterpart monomer, and subsequently dyeing the fabric with said dyestuff.
6. The process of claim 5 wherein the cellulosic textile fabric is a cross-linked cotton fiber textile fabric.
7. The process of claim 5 wherein the cellulosic textile fabric is a crosslinked cotton fiber-synthetic fiber blended textile fabric.
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US4235596A (en) * | 1975-12-23 | 1980-11-25 | Ciba-Geigy Corporation | Process for the pad-dyeing and printing of textile material made from mixed fibres of cellulose and polyester |
US4265631A (en) * | 1978-08-02 | 1981-05-05 | Ciba-Geigy Corporation | Aqueous dyestuff preparations of water-insoluble or sparingly water-soluble dyes |
US4615708A (en) * | 1985-10-18 | 1986-10-07 | The United States Of America As Represented By The Secretary Of Agriculture | Method for insitu coloring crosslinked cellulosic materials |
US4629470A (en) * | 1985-10-18 | 1986-12-16 | The United States Of America As Represented By The Secretary Of Agriculture | Process for dyeing smooth-dry cellulosic fabric |
US4780102A (en) * | 1985-10-18 | 1988-10-25 | The United States Of America As Represented By The Secretary Of Agriculture | Process for dyeing smooth-dry cellulosic fabric |
US4743266A (en) * | 1986-09-09 | 1988-05-10 | The United States Of America As Represented By The Secretary Of Agriculture | Process for producing smooth-dry cellulosic fabric with durable softness and dyeability properties |
US5298584A (en) * | 1990-12-14 | 1994-03-29 | The United States Of America As Represented By The Secretary Of Agriculture | Anionically dyeable smooth-dry crosslinked cellulosic material created by treatment of cellulose with reactive swelling agents and nitrogen based compounds |
US5242463A (en) * | 1991-03-06 | 1993-09-07 | The United States Of America As Represented By The Secretary Of Agriculture | Anionically dyeable smooth-dry crosslinked cellulosic material created by treatment of cellulose with non-reactive glycol ether swelling agents and nitrogen based compounds |
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WO2012135622A1 (en) * | 2011-03-31 | 2012-10-04 | Celanese International Corporation | Disperse dyeing of textile fibers |
US20120246842A1 (en) * | 2011-03-31 | 2012-10-04 | Celanese International Corporation | Disperse dyeing of textile fibers |
CN103459709A (en) * | 2011-03-31 | 2013-12-18 | 国际人造丝公司 | Disperse dyeing of textile fibers |
WO2013130352A3 (en) * | 2012-03-01 | 2013-12-27 | Ticona Llc | Polyarylene sulfide fibers containing an emulsion copolymer coating |
WO2013148295A3 (en) * | 2012-03-30 | 2013-12-19 | Celanese International Corporation | Disperse dyeing of textile fibers |
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