US3322561A - Process for textile decorating and textile webs decorated thereby - Google Patents
Process for textile decorating and textile webs decorated thereby Download PDFInfo
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- US3322561A US3322561A US295813A US29581363A US3322561A US 3322561 A US3322561 A US 3322561A US 295813 A US295813 A US 295813A US 29581363 A US29581363 A US 29581363A US 3322561 A US3322561 A US 3322561A
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- textile
- polyamide
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- 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
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2033—Coating or impregnation formed in situ [e.g., by interfacial condensation, coagulation, precipitation, etc.]
Definitions
- This invention relates to textile decorating with resin bonded pigment colors and to textile webs decorated thereby.
- the basic novel concept of the invention is the formation of a binder resin in situ on the textile fabric by reacting an anionic polymer containing carboxyl groups with certain water-soluble, cationic, thermosetting polymeric materials. Such reaction appears'to take place, at least to some extent, even at room temperature. Such initial room temperature reaction appears to be very desirable and is believed to be largely responsible for the effectiveness of the system to control pigment migration in padding and to obtain improvement in color value in both printing and padding.
- the pH of the material on the fabric must be shifted to the acid side. This is readily accomplished by formulating the pad liquor with some ammonia or volatile amine that is readily driven off when the wet fabric is heated.
- the process of this invention may be carried out by applying the after-treating liquid in any conventional manner for applying liquids to fabrics, such as by printing or padding.
- the paddings may be passed through an infrared-heated area prior to rollup or final drying and curing.
- the spray should be finely atomized and should hit the fabric with considerable force, otherwise the material may acquire a frosty appearance. Too much total Wet pickup should be avoided, whether due to excessive binder spray or too high an amount of wet pickup on the original padding. Otherwise foaming and squeeze-out take place during the rolling up operation while facing and a frosty appearance are displayed in the finished padding. If the binder solution is too concentrated, a frosty appearance is also produced.
- EXAMPLE 1 Anionic padding formulation: Parts by wt., dry basis Phthalocyanine blue 1.00 Sodium lauryl sulfate 080 x 80 count cotton was padded with a padding liquor, at a slightly alkaline pH, consisting of 6.9 parts of the above anionic padding formulation in 93.1 parts of water to give 0.6% pigment on the weight of the fabric. The speed of application was 10 yards per minute, using a deep pan, 2 clips and 1 nip. The wet pickup was 60%.
- a 2% solution of special binder X, described below, at a pH of 4 to 6 was sprayed on the padded cotton with Bink spray guns model 21A, 63 PB air nozzles, and 63A liquid nozzles at a delivery rate of 35 cc. per minute per gun, using 50 lbs. of air (propellant) pres-sure, and 2 lbs. liquid transport pressure.
- the spray nozzles were placed 7 inches from the web, one nozzle on each side. The spray pickup amounted to 25%.
- the inclusion of a cationic or nonionic latex in the overspray liquor is conducive to good fastness properties, especially low crocking, without impairment of hand, since less latex is required in this form of application than in conventional padding for imparting the same desirable fastness properties.
- the amount of binder used in the first padding or printing liquor may thus be reduced to as little as about 10% of that in conventional compositions, however, the total binder in the finished product may have 50% or less of the conventional amount of binder.
- overspray adjuvants may be catalysts, finishing agents, softeners, latices, fire retardants, rot-proofing materials, and in general resins incompatible with the normal components of the pad liquors.
- Combinations of the various ingredients in other ways than those set forth in this description of the invention do not achieve the same good results.
- Inclusion of cationic or nonionic emulsion polymers in the overspray when the special cationic binder-dispersant is present improves crock resistance of deep shade dyeings to the point where a normal crock test shows almost no crocking. This fastness is accomplished at very low ratios of binder to pigment, and With excellent hand. This has heretofore been impossible.
- the polysiloxanes are incompatible and heat resistant, and their action here is believed to be due to their apparent migration to the top of the coated textiles.
- Other materials will do part of the job performed by the polysiloxane but none can be used as completely satisfactory substitutes for it.
- Such other materials are for example microcrystalline wax and finely-divided polyethylene of molecular weight around 18,000.
- a typical formulation with a latex binder and a polysiloxane follows. Parts are parts by weight and percentages are on the weight basis.
- the pH of this mixture is 8 to 9.
- Crosslinker solution Parts Hexamethyl ether of hexamethylol melamine (wet basis) 60 Isopropanol (wet basis) 26 Water 14 Pad liquor:
- Cationic agent X (dry basis) 1.0 Copolymer of 85 parts Z-ethylhexyl acrylate, 13 parts acrylonitrile, 2 parts itaconic acid in latex form with a nonionic emulsifier (dry basis) 8.8 Polydimethylsiloxane (dry basis) 1.75 Water 88.45
- the overspray was applied in the proportion of 20 to 60% (wet basis) on the fabric.
- overspray or overpadding treatment may be applied to textiles printed by conventional methods. Also as before mentioned, the amount of binder in conventional printing compositions may be greatly reduced. Examples of typical printing compositions follow.
- the mixture was emulsified.
- the cationic thermosetting polymeric materials preferred for carrying out the process of this invention comprises water-soluble reaction products of epichlorohydrin and a polyamide derived from a polyalkylene polyamine having two primary amine groups and at least one secondary amine group and a dicarboxylic acid selected from the group consisting of diglycollic acid and C to C saturated aliphatic dicarboxylic acids.
- the polyamide referred to is a water-soluble, long chain polyamide, containing secondary amine groups, the mole ratio of polyalkylene polyamine to dicarboxylic acid being from about 0.8 to 1 to about 1.4 to 1.
- the reaction of the polyamide with epichlorohydrin is carried out in aqueous solution in a mole ratio of from about 0.5 to about 1 epichlorohydrin to about 1.8 to 1 secondary amine groups of the polyamide to form an aqueous solution of a water-soluble, thermosetting cationic resin.
- aqueous solution in a mole ratio of from about 0.5 to about 1 epichlorohydrin to about 1.8 to 1 secondary amine groups of the polyamide to form an aqueous solution of a water-soluble, thermosetting cationic resin.
- a polyamide was made by adding 290 g. of adipic acid to 319 g. of triethylenetetramine and heating the resulting solution 1% hours at 185200 C. The batch was then allowed to cool to 140 C. while under vacuum supplied by a water pump. 430 g. of water were added at this point, giving a polyamide solution having 49.8% solids, a pH of 10.8, and an acid number of 3.2.
- a solution consisting of 225 g. water and 6 3 g. of the above polyamide solution was heated to 50 C. and 25 g. of epichlorohydrin added dropwise over a period of 3 minutes. The solution was then heated to 60-70 C. until the viscosity was E (Gardner). 225 g. of water were added, the batch was cooled to 25 C., and the pH adjusted to 5.0 with 11 ml. of 10% HCl. The product had a solids content of 8.4% and a Gardner viscosity of C., and constituted the previously mentioned special binder X.
- a polyamide was also prepared by reacting 1.25 moles of triethylenetetramine with 1 mole of succinic acid. The product was reacted with epichlorohydrin.
- the batch was refluxed another hour, cooled, and the solvent vacuum distilled oflf at room temperature at 4.5 mm. of mercury.
- a solution of 64 parts of 37% Formalin in 300 parts of water and 41 parts of 29% aqueous ammonium hydroxide was added to the resin and the mixture brought slowly up to 70 C. It was heated 4 hours more at 7072 C. Solids content was 30.9%.
- DX 840-73 is a high molecular weight copolymer of ethylene and maleic anhydride that is partly crosslinked and has a viscosity of 40,000 cps. at 25 C. as a 1% solution in dimethyl formamide. Such compounds are described in US. Patent No. 2,921,928.
- Solvesso is a liquid hydrocarbon solvent predominantly aromatic in character, having a boiling range of 367-421 F. and a kauri-butanol value of 90.
- Varsol is a liquid hydrocarbon solvent, predominantly aliphatic in character, having a boiling range of 322-386 F. and a kauri-butanol value of 38.
- a process for decorating textiles consisting essentially of (1) applying a slightly alkaline anionic, pigmentcontaining textile-coloring composition containing polymeric material containing carboxyl groups to a textile web, (2) applying to the so-treated textile web a suitable quantity of a slightly acidic aqueous solution of a watersoluble cationic thermosetting polymeric material that is reactive with said polymeric material containing carboxyl groups which is made by reacting a polyalkylene polyamine having two primary amine groups and at least one secondary amine group with a dicarboxylic acid selected from the group consisting of diglycollic acid and C to C saturated aliphatic di-carboxylic acids to form a watersoluble long chain polyamide containing secondary amine groups, the mole ratio of polyalkylene polyamine to dicarboxylic acid being from about 0.8 to 1 to about 1.4 to 1, and then reacting the polyamide in aqueous solution with epichlorohydrin in a mole ratio of from about 0.5 to 1 mole of epichlorohydrin to about
- step (2) also contains a substantial amount of at least one non-anionic latex in addition to said cationic thermosetting polymeric material.
- step (2) also contains a minor amount of a polysiloxane selected from the group consisting of polysiloxanes having (A) methyl groups and (B) methyl groups and hydrogen atoms attached to the silicon in the repeating units of the polymer chain.
- step (2) also contains a substantial amount of at least one non-anionic latex mixed with a polysiloxane.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Description
United States Patent 3,322,561 PROCESS FOR TEXTILE DECORATING AND TEXTILE WEBS DECORATED THEREBY Charles A. Kumins, Chappaqua, N.Y., Vernon Lindsay Chase, Butler, N.J., Jerome Fine, Oceanside, N.Y., and
Ernest Messmer, Fair Lawn, N.J., assignors to Inter- Chemical Corporation, New York, N.Y., a corporation of Ohio N0 Drawing. Filed July 17, 1963, Ser. No. 295,813
8 Claims. (Cl. 117-622) This invention relates to textile decorating with resin bonded pigment colors and to textile webs decorated thereby.
In the art of textile decorating with resin bonded pigments, deep-shade pigment coloration has not been so successful as light shade coloration because of the large amount of binder needed to meet minimum fastness requirements. Such processing yields fabrics that have not been accepted by the trade in many applications because of the boardy hand caused by the quantity of binder required. Beyond minimum fastness even large amounts of binder have shown little or no improvement.
It has now been found that after treatment of a deepshade anionic padding or print with minor amounts of a cationic polymeric material improves color value and imparts good wash and scrub-fastness. In padding processes, it also gives excellent migration control in the padding without impairing desirable hand. The application of the new system to textile printing, besides having the advantage of producing fabric with improved color values and good fastness properties, also improves the runnability of low-crock systems. Runnability refers to the amount of continuous processing possible before it becomes necessary to stop the run and clean up the system.
The basic novel concept of the invention is the formation of a binder resin in situ on the textile fabric by reacting an anionic polymer containing carboxyl groups with certain water-soluble, cationic, thermosetting polymeric materials. Such reaction appears'to take place, at least to some extent, even at room temperature. Such initial room temperature reaction appears to be very desirable and is believed to be largely responsible for the effectiveness of the system to control pigment migration in padding and to obtain improvement in color value in both printing and padding.
To obtain maximum fastness properties by heat curing, the pH of the material on the fabric must be shifted to the acid side. This is readily accomplished by formulating the pad liquor with some ammonia or volatile amine that is readily driven off when the wet fabric is heated.
While the process of this invention may be carried out by applying the after-treating liquid in any conventional manner for applying liquids to fabrics, such as by printing or padding, We prefer to spray the solution or dispersion on top of the fabric emerging from the padder or printer coated with the anionic padding or printing composition. In order to reduce the moisture content to a satisfactory level after the binder application, the paddings may be passed through an infrared-heated area prior to rollup or final drying and curing. The spray should be finely atomized and should hit the fabric with considerable force, otherwise the material may acquire a frosty appearance. Too much total Wet pickup should be avoided, whether due to excessive binder spray or too high an amount of wet pickup on the original padding. Otherwise foaming and squeeze-out take place during the rolling up operation while facing and a frosty appearance are displayed in the finished padding. If the binder solution is too concentrated, a frosty appearance is also produced.
"ice
EXAMPLE 1 Anionic padding formulation: Parts by wt., dry basis Phthalocyanine blue 1.00 Sodium lauryl sulfate 080 x 80 count cotton was padded with a padding liquor, at a slightly alkaline pH, consisting of 6.9 parts of the above anionic padding formulation in 93.1 parts of water to give 0.6% pigment on the weight of the fabric. The speed of application was 10 yards per minute, using a deep pan, 2 clips and 1 nip. The wet pickup was 60%. A 2% solution of special binder X, described below, at a pH of 4 to 6 was sprayed on the padded cotton with Bink spray guns model 21A, 63 PB air nozzles, and 63A liquid nozzles at a delivery rate of 35 cc. per minute per gun, using 50 lbs. of air (propellant) pres-sure, and 2 lbs. liquid transport pressure. The spray nozzles were placed 7 inches from the web, one nozzle on each side. The spray pickup amounted to 25%.
The inclusion of a cationic or nonionic latex in the overspray liquor is conducive to good fastness properties, especially low crocking, without impairment of hand, since less latex is required in this form of application than in conventional padding for imparting the same desirable fastness properties. The amount of binder used in the first padding or printing liquor may thus be reduced to as little as about 10% of that in conventional compositions, however, the total binder in the finished product may have 50% or less of the conventional amount of binder. This process also makes possible the application, in a continuous operation, of materials which would be in compatible with other components if put into the pad liquor. Such overspray adjuvants may be catalysts, finishing agents, softeners, latices, fire retardants, rot-proofing materials, and in general resins incompatible with the normal components of the pad liquors. Combinations of the various ingredients in other ways than those set forth in this description of the invention do not achieve the same good results. Inclusion of cationic or nonionic emulsion polymers in the overspray when the special cationic binder-dispersant is present improves crock resistance of deep shade dyeings to the point where a normal crock test shows almost no crocking. This fastness is accomplished at very low ratios of binder to pigment, and With excellent hand. This has heretofore been impossible.
It has further been found that more consistent crock results, and of an improved kind, are obtained by incorporating in the overspray liquor polysiloxanes of the type having methyl groups or methyl groups and hydrogen atoms attached to the silicon in the typical repeating units of the polymer chain. Such materials are represented by the commercial products DC-36 emulsion and Silolf 22 for example. It is surprising that the polysiloxanes improve the dry crock resistance, but not the wet crock resistance. The reproductibility, however, is bettered for both wet and dry crock. This phenomenon is quite different from the behavior of acrylics, for instance. The polysiloxanes are incompatible and heat resistant, and their action here is believed to be due to their apparent migration to the top of the coated textiles. Other materials will do part of the job performed by the polysiloxane but none can be used as completely satisfactory substitutes for it. Such other materials are for example microcrystalline wax and finely-divided polyethylene of molecular weight around 18,000.
A typical formulation with a latex binder and a polysiloxane follows. Parts are parts by weight and percentages are on the weight basis.
EXAMPLE 2 Color mix: Parts Phthalocyanine blue (dry basis) 10.0 Sodium lauryl sulfate (dry basis) 6.0 Special binder and pigment dispersant Y (dry basis) 3.6 Antifoam B emulsion (as is) 1.0 Water 79.4
The pH of this mixture is 8 to 9.
Clear:
Polyacrylic acid (dry basis) 4.0 Sodium lauryl sulfate (dry basis) 2.0 Special binder and pigment dispersant Y (dry basis) 4.25 Ammonia (26%) 1.17 Water to make 100.00
Crosslinker solution: Parts Hexamethyl ether of hexamethylol melamine (wet basis) 60 Isopropanol (wet basis) 26 Water 14 Pad liquor:
Color mix (wet basis) 12.0 Clear (wet basis) 13.2 Crosslinker solution (wet basis) 3.0 Water 71.8
The wet pickup on the fabric was in the range 60 to 80%. Overspray:
Cationic agent X (dry basis) 1.0 Copolymer of 85 parts Z-ethylhexyl acrylate, 13 parts acrylonitrile, 2 parts itaconic acid in latex form with a nonionic emulsifier (dry basis) 8.8 Polydimethylsiloxane (dry basis) 1.75 Water 88.45
The overspray was applied in the proportion of 20 to 60% (wet basis) on the fabric.
Similarly the overspray or overpadding treatment may be applied to textiles printed by conventional methods. Also as before mentioned, the amount of binder in conventional printing compositions may be greatly reduced. Examples of typical printing compositions follow.
EXAMPLE 3 All-aqueous printing paste Color concentrate: Parts by wt. Pigment 13.0 Special binder and pigment dispersant Y (dry basis) 4.9 Sodium lauryl sulfate (dry basis) 0.7 DX 840-73 (dry basis) 1.0 NH OH (26%) 1.0
Water to make 100.0.
Clear: Parts by wt. DX 840-73 (dry basis) 1.5 NH OH (26%) 2.0 Ammonium acetate 1.5
Water to make 100.0.
The concentrate and the clear were combined in the conventional way. A cotton fabric was printed with the resulting paste and then oversprayed with a composition similar to that used in Example 2. The material was dried.
EXAMPLE 4 Oil-in-water printing paste Color concentrate: Parts by wt. Pigment 16.0
Sodium lauryl sulfate 6.4
Methyl cellulose 0.3
NH O'H (26%) 0.6
Special binder and pigment dispersant Y (dry basis) 0.8
Melamine formaldehyde resin 1.4
Varsol 3.7
Water to make 100.0.
The mixture was emulsified. Clear:
Alkyd and melamine formaldehyde resin 0.26
Methyl cellulose 0.32
Sodium lauryl sulfate 0.22
Varsol 49.6
Water 49.6
The mixture was emulsified.
The color concentrate and the clear were combined in the conventional way. A cotton fabric was printed with the resulting paste and then oversprayed with a composition similar to that used in Example 2. Afterwards the treated fabric was dried.
EXAMPLE 5 Water-in oil printing paste Color concentrate: Parts by wt. Pigment 13.0
Dry melamine formaldehyde resin 6.5
Ethyl cellulose 0.5
Water 6.0
Organic solvent (Solvesso 150, turpentine,
pine oil) 74.0
An emulsion was made of the ingredients. Clear:
Alkyd resin 1.25
Varsol 31.25
Water 67.00
Ammonium sulfate 0.30
An emulsion was made of these ingredients.
The color concentrate and the clear were combined in the conventional way. A cotton fabric was printed with the resulting paste and then oversprayed with a composition similar to that used in Example 2. Following this treatment the fabric was dried.
The cationic thermosetting polymeric materials preferred for carrying out the process of this invention comprises water-soluble reaction products of epichlorohydrin and a polyamide derived from a polyalkylene polyamine having two primary amine groups and at least one secondary amine group and a dicarboxylic acid selected from the group consisting of diglycollic acid and C to C saturated aliphatic dicarboxylic acids. The polyamide referred to is a water-soluble, long chain polyamide, containing secondary amine groups, the mole ratio of polyalkylene polyamine to dicarboxylic acid being from about 0.8 to 1 to about 1.4 to 1. The reaction of the polyamide with epichlorohydrin is carried out in aqueous solution in a mole ratio of from about 0.5 to about 1 epichlorohydrin to about 1.8 to 1 secondary amine groups of the polyamide to form an aqueous solution of a water-soluble, thermosetting cationic resin. Such materials are described in US. Patent No. 2,926,154.
Preparation of cationic agents (A) A polyamide was made by adding 290 g. of adipic acid to 319 g. of triethylenetetramine and heating the resulting solution 1% hours at 185200 C. The batch was then allowed to cool to 140 C. while under vacuum supplied by a water pump. 430 g. of water were added at this point, giving a polyamide solution having 49.8% solids, a pH of 10.8, and an acid number of 3.2.
A solution consisting of 225 g. water and 6 3 g. of the above polyamide solution was heated to 50 C. and 25 g. of epichlorohydrin added dropwise over a period of 3 minutes. The solution was then heated to 60-70 C. until the viscosity was E (Gardner). 225 g. of water were added, the batch was cooled to 25 C., and the pH adjusted to 5.0 with 11 ml. of 10% HCl. The product had a solids content of 8.4% and a Gardner viscosity of C., and constituted the previously mentioned special binder X.
(B) Similarly epichlorohydrin was reacted with a polyamide made from 2.8 moles diethylenetri-amine and 2.0 moles adipic acid.
(C) A polyamide was also prepared by reacting 1.25 moles of triethylenetetramine with 1 mole of succinic acid. The product was reacted with epichlorohydrin.
(D) 1.98 moles of diethylenetriamine and 0.24 mole of ethylenediamine were reacted with 1.98 moles of adipic acid in 100 g. water. The resulting polyamide was treated with epichlorohydrin as in the preceding examples.
(E) 2.2 moles of tetraethylenepentamine were reacted with 1.81 moles of adipic acid and the resulting polyamide was also reacted with epichlorohydrin.
The specific details of these and similar preparations may he found in US. Patent No. 2,926,154, previously referred to. The epichlorohydrin is added in sufficient amount to convert all secondary amine groups to tertiary amine groups or quarternary ammonium groups including cyclic structures. More than this or even less may be used to help regulate the rate of reaction. The various polyamines and acids suitable are also described in the patent.
Special binder and pigment dispersant Y 125 parts of isopropanol were heated to reflux (82 C.). Then over a period of 1 hour was added a mixture of 28.2 parts acrylamide, 130.0 parts ethyl acrylate, 20.0 parts lauryl acrylate, 10.0 parts methacrylic acid, 75.0 parts isopropanol, 1.5 parts benzoyl peroxide, and 0.8 part of tertiary-dodecyl merca-ptan, the reflux temperature of 82-83 C. being maintained. Refluxing was continued 2 hours more. 1.5 parts benzoyl peroxide were added. The batch was refluxed another hour, cooled, and the solvent vacuum distilled oflf at room temperature at 4.5 mm. of mercury. A solution of 64 parts of 37% Formalin in 300 parts of water and 41 parts of 29% aqueous ammonium hydroxide was added to the resin and the mixture brought slowly up to 70 C. It was heated 4 hours more at 7072 C. Solids content was 30.9%.
Other proportions may be used, for instance 60-70 parts of ethyl acrylate, 5-20 parts lauryl methacrylate, 5-20 parts methacrylic acid, and 20 parts acrylamide. Instead of acrylamide, N-methylolacry-lamide, N,N-di allyl melamine, or similar compositions with similar properties would also be suitable. Instead of Y, Carboset 531 may be used.
"DX 840-73 is a high molecular weight copolymer of ethylene and maleic anhydride that is partly crosslinked and has a viscosity of 40,000 cps. at 25 C. as a 1% solution in dimethyl formamide. Such compounds are described in US. Patent No. 2,921,928.
Solvesso is a liquid hydrocarbon solvent predominantly aromatic in character, having a boiling range of 367-421 F. and a kauri-butanol value of 90.
Varsol is a liquid hydrocarbon solvent, predominantly aliphatic in character, having a boiling range of 322-386 F. and a kauri-butanol value of 38.
What is claimed is:
1. A process for decorating textiles consisting essentially of (1) applying a slightly alkaline anionic, pigmentcontaining textile-coloring composition containing polymeric material containing carboxyl groups to a textile web, (2) applying to the so-treated textile web a suitable quantity of a slightly acidic aqueous solution of a watersoluble cationic thermosetting polymeric material that is reactive with said polymeric material containing carboxyl groups which is made by reacting a polyalkylene polyamine having two primary amine groups and at least one secondary amine group with a dicarboxylic acid selected from the group consisting of diglycollic acid and C to C saturated aliphatic di-carboxylic acids to form a watersoluble long chain polyamide containing secondary amine groups, the mole ratio of polyalkylene polyamine to dicarboxylic acid being from about 0.8 to 1 to about 1.4 to 1, and then reacting the polyamide in aqueous solution with epichlorohydrin in a mole ratio of from about 0.5 to 1 mole of epichlorohydrin to about 1.8 to 1 mole of secondary amine groups of said polyamide to form an aqueous solution of a water-soluble cationic thermosetting resin, and (3) subsequently drying the treated textile web.
2. The process described in claim 1, in which the material described in step (2) also contains a substantial amount of at least one non-anionic latex in addition to said cationic thermosetting polymeric material.
3. The process described in claim 2, in which the material described in step (2) also contains a minor amount of a polysiloxane selected from the group consisting of polysiloxanes having (A) methyl groups and (B) methyl groups and hydrogen atoms attached to the silicon in the repeating units of the polymer chain.
4. The process described in claim 1, in which the material described in step (2) also contains a substantial amount of at least one non-anionic latex mixed with a polysiloxane.
5. A textile web decorated by the process described in claim 1.
6. A textile web decorated by the process described in claim 2.
7. A textile web decorated by the process described in claim 3.
8. A textile web decorated by the process described in claim 4.
References Cited UNITED STATES PATENTS 2,926,154 2/ 1960 Keim 260-292 2,995,512 8/1961 Weidner et al. 117-163 X 3,062,686 11/1962 Graulich et al. 117-1395 X 3,211,580 10/1965 Langmann et al. 117-143 X 3,224,986 12/1965 Butler et al. 117-1395 X WILLIAM D. MARTIN, Primary Examiner.
H. W. MYLIUS, M. R. LUSIGNAN,
Assistant Examiners.
Claims (1)
1. A PROCESS FOR DECORATING TEXTILES CONSISTING ESSENTIALLY OF (1) APPLYING A SLIGHTLY ALKALINE ANIONIC, PIGMENTCONTAINING TEXTILE-COLORING COMPOSITION CONTAINING POLYMERIC MATERIAL CONTAINING CARBOXYL GROUPS TO A TEXTIEL WEB, (2) APPLYING TO THE SO-TREATED TEXTILE WEB A SUITABLE QUANTITY OF A SLIGHTLY ACIDIC AQUEOUS SOUTION OF A WATERSOLUBLE CATIONIC THERMOSETTING POLYMERTIC MATERIAL THAT IS REACTIVE WITH SAID POLYMERIC MATERIAL CONTAINING CARBOXYL GROUPS WHICH IS MADE BY REACTING A POLYALKYLENE POLYAMINE HAVING TWO PRIMARY AMINE GROUPS AND AT LEAST ONE SECONDARY AMINE GROUP WITH A DICARBOXYLIC ACID SELECTED FROM THE GROUP CONSISTING OF DIGLYCOLIC ACID AND C3 TO C8 SATURATED ALIPHATIC DICARBOXYLIC ACIDS TO FORM A WATERSOLUBLE LONG CHAIN POLYAMIDE CONTAINING SECONDARY AMINE GROUPS, THE MOLE RATIO OF POLYALKYLENE POLYAMINE TO DICARBOXYLIC ACID BEING FROM ABOUT 0.8 TO 1 TO ABOUT 1.4 TO 1, AND THEN REACTING THE POLYAMIDE IN AQUEOUS SOLUTION WITH EPICHLOROHYDRIN IN A MOLE RATIO OF FROM ABOUT 0.5 TO 1 MOLE OF EPICHLOROHYDRIN TO ABOUT J1.8 TO 1 MOLE OF SECONDARY AMINE GROUPS OF SAID-POLYAMIDE TO FORM AN AQUEOUS SOLUTION OF A WATER-SOLUBLE CATIONIC THERMOSETTING RESIN, AND (3) SUBSEQUENTLY DRYING THE TREATED TEXTILE WEB.
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3428479A (en) * | 1966-02-25 | 1969-02-18 | American Cyanamid Co | Anchoring composition for film and film anchored therewith |
US3471428A (en) * | 1965-10-01 | 1969-10-07 | Champion Products | Plastisol inks for fabrics |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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US2926154A (en) * | 1957-09-05 | 1960-02-23 | Hercules Powder Co Ltd | Cationic thermosetting polyamide-epichlorohydrin resins and process of making same |
US2995512A (en) * | 1950-02-17 | 1961-08-08 | Dow Chemical Co | Clarification process |
US3062686A (en) * | 1955-04-30 | 1962-11-06 | Bayer Ag | Process of treating textile with a copolymer and a cross-linking agent |
US3211580A (en) * | 1959-11-21 | 1965-10-12 | Bayer Ag | Process for the treatment of materials with silicones |
US3224986A (en) * | 1962-04-18 | 1965-12-21 | Hercules Powder Co Ltd | Cationic epichlorohydrin modified polyamide reacted with water-soluble polymers |
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1963
- 1963-07-17 US US295813A patent/US3322561A/en not_active Expired - Lifetime
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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US2995512A (en) * | 1950-02-17 | 1961-08-08 | Dow Chemical Co | Clarification process |
US3062686A (en) * | 1955-04-30 | 1962-11-06 | Bayer Ag | Process of treating textile with a copolymer and a cross-linking agent |
US2926154A (en) * | 1957-09-05 | 1960-02-23 | Hercules Powder Co Ltd | Cationic thermosetting polyamide-epichlorohydrin resins and process of making same |
US3211580A (en) * | 1959-11-21 | 1965-10-12 | Bayer Ag | Process for the treatment of materials with silicones |
US3224986A (en) * | 1962-04-18 | 1965-12-21 | Hercules Powder Co Ltd | Cationic epichlorohydrin modified polyamide reacted with water-soluble polymers |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3471428A (en) * | 1965-10-01 | 1969-10-07 | Champion Products | Plastisol inks for fabrics |
US3428479A (en) * | 1966-02-25 | 1969-02-18 | American Cyanamid Co | Anchoring composition for film and film anchored therewith |
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