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US3519626A - Amino - methylolated melamines and processes for finishing cellulose textile - Google Patents

Amino - methylolated melamines and processes for finishing cellulose textile Download PDF

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US3519626A
US3519626A US622415A US3519626DA US3519626A US 3519626 A US3519626 A US 3519626A US 622415 A US622415 A US 622415A US 3519626D A US3519626D A US 3519626DA US 3519626 A US3519626 A US 3519626A
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dyed
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Michael Thomas Beachem
Frederic Houghton Megson
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Wyeth Holdings LLC
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American Cyanamid Co
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    • 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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423—Amino-aldehyde resins
    • 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

  • alkyl is a lower-alkyl group (1-4 C atoms) and each of R and R is hydrogen, alkyl or up to 18 C atoms, phenyl or phenyl-(lower-alkyl), any of the phenyl or said R groups, especially when R is aryl, having up to two inert radicals, such as lower-alkyl and loweralkoxy.
  • aminoplast resins to impart crease-resistance to cellulosics is well-known. These resin perform their function economically and efiiciently without adversely alfecting many of the other desirable properties of cellulosics, such as for example, fabric hand, soil resistance or fabric durability. However, aminoplast resins do, in some cases, have an adverse efiect on color stability of dyed cellulosics.
  • aminoplast crease-preventing finishes can cause accelerated fading of many direct dyes, i.e., the lightfastness of cellulosic textile material dyed with direct dyes is often reduced when the dyed material is after-treated with an aminoplast resin or reactant, such as a urea formaldehyde or a melamine-formaldehyde condensate.
  • an aminoplast resin or reactant such as a urea formaldehyde or a melamine-formaldehyde condensate.
  • Commercial resins which have been shown to cause fading of certain direct dyes include hexa(methoxymethyl)melamine, polymethylolurea with slight degree of methylation, blends of partially methylated hexamethylolmelamine and ureaformaldehyde reaction products, and methylated trimethylolmelamine.
  • methylolated melamines of Formula I impart crease-resistant properties to cellulosic textile materials without adversely affecting the lightfastness of such material dyed with direct dyes. This is a surprising discovery since cellulosics dyed with direct dyes are normally adversely aifected as to lightfastness when aftertreated with aminoplast textile finishes.
  • the textile finishing aminoplast resins used in this invention are applied to direct-dyed cellulosic textile materials by standard procedures, as by dipping, padding, spraying, etc., and the finishes are converted to an insoluble state by heating the treated fabrics in the presence of a catalyst.
  • the dyed materials thus treated exhibit crease-resistant and wrinkle-recovery properties, and a lightfastness equal to, or even better than the untreated, dyed material.
  • the compounds of Formula I can be made by reacting an N-halomethylmelamine of Formula II with a compound of Formula III as follows:
  • N-halomethylmelamines of Formula II which can be used in this invention include N-chloromethyl N,N,N',N",N pentakis (methoXymethyl)-2,4, 6-triamino-s-triazine, N bromomethyl N,N,N',N",N"- pentakis(methoxymethyl) 2,4,6 triamino s triazine, N bromomethyl N,N',N,N",N" pentakis(ethoxymethyl)-2,4,6-triamino-s-triazine, N-chloromethyl-N,N', N,N",N” pentakis (butoxymethyl)-2,4,6-triamino-s-triazine, etc.
  • Representative compounds of Formula HI include diphenylamine, di p tolylamine, di-m-tolylamine, bis- (p-ethylphenyl)amine, p-methyldiphenylamine, and bis- (p-methoxybiphenylyl amine.
  • reaction of compounds of Formula II with compounds of Formula III is carried out with or without a solvent, although it is preferable to use a solvent, particularly when both reactants are solids. It is also advantageous to use an acid acceptor such as an alkali metal carbonate or bicarbonate to take up the hydrogen halide which is formed by the reaction.
  • the reaction is conveniently carried out at room temperature, although any temperature between the freezing and boiling points of 3 the reaction mixture may be used. Equimolar amounts of reactants can be advantageously used although an excess of either can be present without adverse effect.
  • the cellulosic textile materials include fibers, threads, yarns, knitted and woven cloth as well as non-woven fabrics and felted materials. These cellulosic materials will normally contain at least 50% cellulosic fibers, such as cotton, viscose, cuprammonium rayons, linen, hemp, jute, and ramie, either alone or mixed with themselves or other fibers.
  • the cellulosic textile materials will be dyed with the class of azo dyes known as direct dyes and so classified in the Color Index, second edition.
  • Such dyes are characterized as anionic dyes having affinity for cellulosic fibers when applied from an aqueous dyebath containing an electrolyte. They are mainly azo dyes containing sulfonic acid groups as the sodium salts.
  • Representative direct dyes are Direct Yellow 6 (C.I. 4001), Direct Yellow 11 (C.I. 40000), Direct Orange 26 (C.I. 29150), Direct Red 1 (C.I. 22310), Direct Red 31 (C.I. 29100), Direct Blue 2 (C.I. 22590) and Direct Green 1 (30280).
  • the dyed materials are treated with the textile finishes of this invention using aqueous or organic solvent solutions or dispersions which can be applied by spraying, dipping or padding according to well-known procedures. Between 0.5% and 40% solutions or dispersions are normally used.
  • the amount of finish on the textile material can be varied, usually between 0.5% and 40% based on the weight of the textile material, with amounts between 2.5% and 15% preferably being used for practical creaseresistant and wrinkle-recovery properties.
  • the treated fabrics are dried and then heated, preferably in the presence of a catalyst, to effect insolubility of the precondensate on the fabric (cross-linking, etc.). Curing temperatures between 275 and 400 F. for periods of about minutes to seconds are normally used.
  • Suitable catalysts include those normally used for melamineformaldehyde condensates and their etherates. These include the metal salts such as magnesium chloride, zinc nitrate and zinc chloride, ammonium salts such as ammonium sulfate, ammonium chloride, and organic amine hydrochlorides, In the case of magnesium chloride, the amount is between about 4.5% and 24%, preferably between 9% and 15 of the anhydrous salt based on the weight of the precondensate.
  • the treated dyed fabric obtained by this invention will be found to have good wrinkle recovery and crease resistance normally required for commercial cellulosics. In addition, advantageously, they will be found to possess lightfastness not previously attained with aminoplast resintreated direct-dyed cellulosics.
  • the residue from the evaporation of the ether, a viscous liquid, is N (di p-tolylaminomethyl)-N,N',N',N",N"-pentakis (methoxymethyl -2,4,6-triamino-s-triazine.
  • the benzene is removed by distillation and the residue is extracted with ether.
  • the residue from the evaporation of the ether, a viscous liquid, is N (diphenylaminomethyl) N,N,N,N",N pentakis (ethoxymethyl)-2,4,6-triamino-s-triazine.
  • reaction mixture is filtered, and the acetone is removed by distillation.
  • a solution of the residue in benzene is washed with water.
  • the benzene is removed by distillation and the residue is extracted with ether.
  • the residue from the evaporation of the ether, a viscous liquid, is N [di(biphenylyl)aminomethyl]-N,N',N',N",N"-pentakis (methoxymethyl) -2,4,6-triamino-s-triazine.
  • Pad baths are prepared containing 6.25% precondensate solids and 12% magnesium chloride based on the precondensate solids in the bath.
  • Pad bath A N (diphenylaminomethyl) N,N', N,N,N"-pentakis (methoxymethyl)-2,4,6-triamino-s-triazine in acetone.
  • Pad bath B N,N,N,N',N,N hexakis(methoxymethyl)-2,4,6-triamino-s-triazine in water.
  • the pad baths are applied to a sample of 80 x 80 cotton percale dyed with Direct Red 81 (CI. 28160) at 5% O.W.F. of precondensate solids by standard padding procedure using 80% wet pickup.
  • the treated fabrics are dried for 2 minutes at 225 F., and the finishes are cured by heating the fabrics at 350 F. for 1.5 minutes.
  • a sample of the dyed, but untreated, fabric is rinsed in water and dried. A portion of each of the fabrics of each color is washed in a home-style washing machine at 110- 115 F. with water containing 0.25% of a commercial anionic surface active agent and 0.25% of sodium carbonate. The washed fabrics are dried.
  • Spectrophotometric curves of the unexposed portion of dyed fabric and the exposed portion of dyed fabric are recorded for 21 wavelengths over the complete visual range.
  • the spectrophotometric data are converted to colorimetric data by means of a digital computer. Numerical expressions of color in terms of 3-dimensional color coordinates are thus obtained.
  • the two sets of colorimetric data i.e., one set for unexposed fabric and one set for the exposed fabric, are then converted into a single color difference (in NBS units) by the system of Wyszecki, J. Opt. Soc. Am., 53, 1318 (1963).
  • the evaluation of the colorimetric data can be done by computer.
  • the single number color difference thus obtained can be considered in this instance to be strength ratio figures between exposed and unexposed fabric, negative numbers indicating loss in strength, i.e. fading.
  • finish A is superior to finish B in resistance to light-fading and is generally equivalent to the untreated dyed fabric.
  • alkyl is an alkyl radical of 1-4 C atoms and R and R are individually either hydrogen, alkyl of up to 18 C atoms, phenyl or (lower-alkoxy)phenyl.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

United States Patent 3,519,626 AMINO METHYLOLATED MELAMINES AND PROCESSES FOR FINISHING CELLULOSE TEXTILE Michael Thomas Beachem, Somerset, and Frederic Hough- 5 ton Megson, Martinsville, N.J., assignors to American Cyanamid Company, Stamford, Conn., a corporation of Maine No Drawing. Filed Mar. 13, 1967, Ser. No. 622,415 Int. Cl. C07d 55/22 US. Cl. 260-249.6 6 Claims ABSTRACT OF THE DISCLOSURE This invention relates to new amino-methylolated melamines and to their use on cellulosic textile materials that have been dyed with direct dyes. The new aminomethylolated melamines impart crease-resistance to such materials and dyed materials so finished have improved light-fastness.
wherein alkyl is a lower-alkyl group (1-4 C atoms) and each of R and R is hydrogen, alkyl or up to 18 C atoms, phenyl or phenyl-(lower-alkyl), any of the phenyl or said R groups, especially when R is aryl, having up to two inert radicals, such as lower-alkyl and loweralkoxy.
The use of aminoplast resins to impart crease-resistance to cellulosics is well-known. These resin perform their function economically and efiiciently without adversely alfecting many of the other desirable properties of cellulosics, such as for example, fabric hand, soil resistance or fabric durability. However, aminoplast resins do, in some cases, have an adverse efiect on color stability of dyed cellulosics. Thus, it is well-known that aminoplast crease-preventing finishes can cause accelerated fading of many direct dyes, i.e., the lightfastness of cellulosic textile material dyed with direct dyes is often reduced when the dyed material is after-treated with an aminoplast resin or reactant, such as a urea formaldehyde or a melamine-formaldehyde condensate. Commercial resins which have been shown to cause fading of certain direct dyes include hexa(methoxymethyl)melamine, polymethylolurea with slight degree of methylation, blends of partially methylated hexamethylolmelamine and ureaformaldehyde reaction products, and methylated trimethylolmelamine.
In view of the widespread use of both direct dyes and aminoplast resins on cellulosics, it is extremely und'e sirable to have the use of the resin for its purpose, restrict the functioning of the dye for its purpose. It is therefore 3,519,626 Patented July 7, 1970 an object of the present invention to provide a means of treating direct dyed cellulosics with aminoplast resins whereby crease-resistance is imparted to the cellulosic with no substantial reduction in lightfastness other than normally encountered. It is a further object to provide cellulosics which have been direct dyed and have improved lightfastness while also exhibiting good creaseresistance by virtue of treatment with a particular aminoplast resin textile improving agent. Other objects will be apparent from the ensuing description of this invention.
It has now been discovered in accordance with this invention that methylolated melamines of Formula I impart crease-resistant properties to cellulosic textile materials without adversely affecting the lightfastness of such material dyed with direct dyes. This is a surprising discovery since cellulosics dyed with direct dyes are normally adversely aifected as to lightfastness when aftertreated with aminoplast textile finishes.
The textile finishing aminoplast resins used in this invention are applied to direct-dyed cellulosic textile materials by standard procedures, as by dipping, padding, spraying, etc., and the finishes are converted to an insoluble state by heating the treated fabrics in the presence of a catalyst. The dyed materials thus treated exhibit crease-resistant and wrinkle-recovery properties, and a lightfastness equal to, or even better than the untreated, dyed material.
The compounds of Formula I can be made by reacting an N-halomethylmelamine of Formula II with a compound of Formula III as follows:
CHz0-alkyl HN (alkyl-O (lHmN-ii wherein X is chlorine or bromine and alkyl and R and R are as defined above for Formula I. The compounds of Formula II and a process for their manufacture are disclosed and claimed in US. Pat. No. 3,317,529, issued May 2, 1967 to Beachem et al.
Representative N-halomethylmelamines of Formula II which can be used in this invention include N-chloromethyl N,N,N',N",N pentakis (methoXymethyl)-2,4, 6-triamino-s-triazine, N bromomethyl N,N,N',N",N"- pentakis(methoxymethyl) 2,4,6 triamino s triazine, N bromomethyl N,N',N,N",N" pentakis(ethoxymethyl)-2,4,6-triamino-s-triazine, N-chloromethyl-N,N', N,N",N" pentakis (butoxymethyl)-2,4,6-triamino-s-triazine, etc.
Representative compounds of Formula HI include diphenylamine, di p tolylamine, di-m-tolylamine, bis- (p-ethylphenyl)amine, p-methyldiphenylamine, and bis- (p-methoxybiphenylyl amine.
The reaction of compounds of Formula II with compounds of Formula III is carried out with or without a solvent, although it is preferable to use a solvent, particularly when both reactants are solids. It is also advantageous to use an acid acceptor such as an alkali metal carbonate or bicarbonate to take up the hydrogen halide which is formed by the reaction. The reaction is conveniently carried out at room temperature, although any temperature between the freezing and boiling points of 3 the reaction mixture may be used. Equimolar amounts of reactants can be advantageously used although an excess of either can be present without adverse effect.
The cellulosic textile materials include fibers, threads, yarns, knitted and woven cloth as well as non-woven fabrics and felted materials. These cellulosic materials will normally contain at least 50% cellulosic fibers, such as cotton, viscose, cuprammonium rayons, linen, hemp, jute, and ramie, either alone or mixed with themselves or other fibers.
The cellulosic textile materials will be dyed with the class of azo dyes known as direct dyes and so classified in the Color Index, second edition. Such dyes are characterized as anionic dyes having affinity for cellulosic fibers when applied from an aqueous dyebath containing an electrolyte. They are mainly azo dyes containing sulfonic acid groups as the sodium salts. Representative direct dyes are Direct Yellow 6 (C.I. 4001), Direct Yellow 11 (C.I. 40000), Direct Orange 26 (C.I. 29150), Direct Red 1 (C.I. 22310), Direct Red 31 (C.I. 29100), Direct Blue 2 (C.I. 22590) and Direct Green 1 (30280).
The dyed materials are treated with the textile finishes of this invention using aqueous or organic solvent solutions or dispersions which can be applied by spraying, dipping or padding according to well-known procedures. Between 0.5% and 40% solutions or dispersions are normally used. The amount of finish on the textile material can be varied, usually between 0.5% and 40% based on the weight of the textile material, with amounts between 2.5% and 15% preferably being used for practical creaseresistant and wrinkle-recovery properties. The treated fabrics are dried and then heated, preferably in the presence of a catalyst, to effect insolubility of the precondensate on the fabric (cross-linking, etc.). Curing temperatures between 275 and 400 F. for periods of about minutes to seconds are normally used. Suitable catalysts include those normally used for melamineformaldehyde condensates and their etherates. These include the metal salts such as magnesium chloride, zinc nitrate and zinc chloride, ammonium salts such as ammonium sulfate, ammonium chloride, and organic amine hydrochlorides, In the case of magnesium chloride, the amount is between about 4.5% and 24%, preferably between 9% and 15 of the anhydrous salt based on the weight of the precondensate.
The treated dyed fabric obtained by this invention will be found to have good wrinkle recovery and crease resistance normally required for commercial cellulosics. In addition, advantageously, they will be found to possess lightfastness not previously attained with aminoplast resintreated direct-dyed cellulosics.
The following examples are presented to further illustrate this invention.
EXAMPLE 1 CH2O CH3 To a solution of 25.4 parts (0.15 mole) of diphenylamine in 80 parts of acetone containing 82.9 parts (0.60 mole) of potassium carbonate there is added a solution of 138.4 parts (0.30 mole) of N-chloromethyl-N,N,N',N",
"-pentakis(methoxymethyl)-2,4,6-triamino-s-triazine in 80 parts of acetone. After a reaction period of about 15 hours, the reaction mixture is filtered, and the acetone is removed by distillation. A solution of the residue in benzene is washed with water. Thet benzene is removed by distillation and the residue is extracted with ether. The residue from the evaporation of the ether, a viscous liquid, is N (diphenylaminomethyl) N,N,N',N",N pentakis (methoxymethyl)-2,4,6-triamino-s-triazine.
4 EXAMPLE 2 lTKCHzO CH3):
N onmtclnronupuz To a solution of 0.15 mole of di(p-tolyl)amine in parts of acetone containing 82.9 parts (0.60 mole) of potassium carbonate there is added a solution of 138.4 parts (0.30 mole) of N-chloromethyl-N,N,N,N",N"- pentakis(methoxymethyl)-2,4,6-triamino-s-triazine in 80 parts of acetone. After a reaction period of about 15 hours, the reaction mixture is filtered, and the acetone is removed by distillation. A solution of the residue in benzene is washed with water. The benzene is removed by distillation and the residue is extracted with ether. The residue from the evaporation of the ether, a viscous liquid, is N (di p-tolylaminomethyl)-N,N',N',N",N"-pentakis (methoxymethyl -2,4,6-triamino-s-triazine.
EXAMPLE 3 N(CH2OC2H5)2 01120011 (CH3O CHzhN-(J To a solution of 25.4 parts (0.15 mole) of diphenylamine in 80 parts of acetone containing 82.9 parts (0.60 mole) of potassium carbonate there is added a solution of 0.30 mole of N-chloromethyl-N,N,N,N",N-pentakis (ethoxymethyl)-2,4,6-triamino-s-triazine in 80 parts of acetone. After a reaction period of about 15 hours, the reaction mixture is filtered, and the acetone is removed by distillation. A solution of the residue in benzene is washed with water. The benzene is removed by distillation and the residue is extracted with ether. The residue from the evaporation of the ether, a viscous liquid, is N (diphenylaminomethyl) N,N,N,N",N pentakis (ethoxymethyl)-2,4,6-triamino-s-triazine.
EXAMPLE 4 V H2OCH3M 0\ N/ N (oH,ooHl)zN i N N C H2N[ C BH4C a r-(pnz To a solution of 0.15 mole of di(biphenylyl)amine in 80 parts of acetone containing 82.9 parts (0.60 mole) of potassium carbonate there is added a solution of 138.4 parts (0.30 mole) of N-chloromethyl-N,N',N',N",N"- pentakis(rr'1ethoxymethyl)-2,4,6-triamino-s-triazine in 80 parts of acetone. After a reaction period of about 15 hours, the reaction mixture is filtered, and the acetone is removed by distillation. A solution of the residue in benzene is washed with water. The benzene is removed by distillation and the residue is extracted with ether. The residue from the evaporation of the ether, a viscous liquid, is N [di(biphenylyl)aminomethyl]-N,N',N',N",N"-pentakis (methoxymethyl) -2,4,6-triamino-s-triazine.
EXAMPLE 5 lTHCHzOOHQz OHzOCHg CHzOCH;
parts of acetone. After a reaction period of about hours, the reaction mixture is filtered, and the acetone is removed by distillation. A solution of the residue in benzene is washed with water. The benzene is removed by distillation and the residue is extracted with ether. The residue from the evaporation of the ether, a viscous liquid, is N [di(p-ethylphenyl)aminomethyl]-N,N,N,N,N- pentakis (methoxymethyl) -2,4,6-triamino-s-triazine.
EXAMPLE 6 Pad baths are prepared containing 6.25% precondensate solids and 12% magnesium chloride based on the precondensate solids in the bath.
Pad bath A N (diphenylaminomethyl) N,N', N,N,N"-pentakis (methoxymethyl)-2,4,6-triamino-s-triazine in acetone.
Pad bath B N,N,N,N',N,N hexakis(methoxymethyl)-2,4,6-triamino-s-triazine in water.
The pad baths are applied to a sample of 80 x 80 cotton percale dyed with Direct Red 81 (CI. 28160) at 5% O.W.F. of precondensate solids by standard padding procedure using 80% wet pickup. The treated fabrics are dried for 2 minutes at 225 F., and the finishes are cured by heating the fabrics at 350 F. for 1.5 minutes. Also, a sample of the dyed, but untreated, fabric is rinsed in water and dried. A portion of each of the fabrics of each color is washed in a home-style washing machine at 110- 115 F. with water containing 0.25% of a commercial anionic surface active agent and 0.25% of sodium carbonate. The washed fabrics are dried.
Samples of the treated fabrics, both washed and unwashed, are exposed in a Fadc-Ometer for 60 hours. The degree of fading of the exposed samples of fabric is measured as follows:
Spectrophotometric curves of the unexposed portion of dyed fabric and the exposed portion of dyed fabric are recorded for 21 wavelengths over the complete visual range. The spectrophotometric data are converted to colorimetric data by means of a digital computer. Numerical expressions of color in terms of 3-dimensional color coordinates are thus obtained. The two sets of colorimetric data, i.e., one set for unexposed fabric and one set for the exposed fabric, are then converted into a single color difference (in NBS units) by the system of Wyszecki, J. Opt. Soc. Am., 53, 1318 (1963). The evaluation of the colorimetric data can be done by computer.
The single number color difference thus obtained can be considered in this instance to be strength ratio figures between exposed and unexposed fabric, negative numbers indicating loss in strength, i.e. fading. The larger the color difference number, the greater the difference in the visual appearance between the two samples.
It is generally accepted that a color difference of 0.2 NBS unit is the minimum detectable amount which an experienced person can detect between two samples. The color difference for an acceptable commercial match is probably between 1.0 and 2.0 NBS units as discussed in the monograph by Judd, Color in Business, Science and Industry, Wiley, New York, 1952.
The results of the fading measurements are shown in Table I, finishes A and B, corresponding to pad baths A and B, respectively.
TABLE I.-FADING IN NBS UNITS It can be seen that finish A is superior to finish B in resistance to light-fading and is generally equivalent to the untreated dyed fabric.
6 What is claimed is: 1. A compound of the formula:
CHaO-alkyl wherein alkyl is an alkyl radical of 1-4 C atoms and R and R are individually either hydrogen, alkyl of up to 18 C atoms, phenyl or (lower-alkoxy)phenyl.
2. The compound according to claim 1 which has the formula:
N(CH2O cHm (CH O Guam-b C-N N CHzN(CeHs)2 3. The compound according to claim 1 which has the formula:
onto on,
4. The compound according to claim 1 which has the formula:
I 01120 CH3 (CHsOCHQzN-b N/ \N CHzO CzHs (C2H5OCH2)2Ni y N\ N CH2N C6HE 2 5. The compound according to claim 1 which has the formula:
I i (OHKO CH2)2N C-N N CHzN[C H CsH5(D)]2 6. The compound according to claim 1 which has the formula:
N CH2O CH OTHER REFERENCES Campbell et al., J. Org. Chem., vol. 26, pp. 2786-9 (1961).
JOHN D. RANDOLPH, Primary Examiner I. M. FORD, Assistant Examiner US. Cl. X.R.
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Cited By (3)

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US3617182A (en) * 1967-03-13 1971-11-02 American Cyanamid Co Process for finishing cellulosic textile materials with etherified melamines
US3878163A (en) * 1971-07-01 1975-04-15 Martin Dexter 3,5-dialkyl-4-hydroxyphenyl alkanoic acid esters of 2,4,6-tris(alkanolamino) derivatives of triazine as antioxidants
US9017353B2 (en) 2004-11-12 2015-04-28 Boston Scientific Scimed, Inc. Cutting balloon catheter having flexible atherotomes

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CA2205098A1 (en) * 1996-05-17 1997-11-17 James D. Burrington Alkylation of aromatic amines using a heteropoly catalyst

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US2861054A (en) * 1953-06-03 1958-11-18 Montclair Res Corp Water repellents techniques
US3422020A (en) * 1965-02-11 1969-01-14 Henkel & Cie Gmbh Low-sudsing detergent compositions

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US3519626A (en) * 1967-03-13 1970-07-07 American Cyanamid Co Amino - methylolated melamines and processes for finishing cellulose textile

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US2709693A (en) * 1950-12-04 1955-05-31 Ciba Ltd Etherified condensation products of formaldehyde with amino-1:3:5-triazines containing at least two aminogroups
US2861054A (en) * 1953-06-03 1958-11-18 Montclair Res Corp Water repellents techniques
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3617182A (en) * 1967-03-13 1971-11-02 American Cyanamid Co Process for finishing cellulosic textile materials with etherified melamines
US3878163A (en) * 1971-07-01 1975-04-15 Martin Dexter 3,5-dialkyl-4-hydroxyphenyl alkanoic acid esters of 2,4,6-tris(alkanolamino) derivatives of triazine as antioxidants
US9017353B2 (en) 2004-11-12 2015-04-28 Boston Scientific Scimed, Inc. Cutting balloon catheter having flexible atherotomes
US9603619B2 (en) 2004-11-12 2017-03-28 Boston Scientific Scimed, Inc. Cutting balloon catheter having flexible atherotomes

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