Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
  • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
  • C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
  • C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
  • C07D239/10—Oxygen or sulfur atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
  • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
  • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D233/30—Oxygen or sulfur atoms
  • C07D233/32—One oxygen atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
  • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
  • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D233/30—Oxygen or sulfur atoms
  • C07D233/40—Two or more oxygen atoms
• • 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
  • 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
  • Y10T442/2369—Coating or impregnation improves elasticity, bendability, resiliency, flexibility, or shape retention of the fabric
  • Y10T442/2393—Coating or impregnation provides crease-resistance or wash and wear characteristics
• • 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
  • Y10T442/2549—Coating or impregnation is chemically inert or of stated nonreactance
  • Y10T442/2574—Acid or alkali resistant

Definitions

• This invention relates to the finishing of fabrics, particularly cotton fabrics and cotton polyester blends so as to make them wrinkle and crush resistant, resistant to scorching and yellowing and capable of being laundered with the use of hypochlorite bleaching and acid sours in the rinse without suffering any deleterious effects, including substantial loss in tensile strength.
• the invention is particularly concerned with such finishes and methods of producing them.
• carbamate finishes are quite volatile and have a tendency to sublime on drying and even in storage. For this reason, they do not lend themselves well to permanent press or delayed curing processes.
• a garment made from uncured fabric treated with a conventional carbamate finish may 3,590,100 Patented June 29, 1971 lose most of its finish by sublimation before the garment is given the final processing.
• An object of the present invention is the provision of finishes which will have all the advantages of carbamate finishes but which will not have any drawbacks of these finishes.
• Another object is to eliminate the disadvantages of excessive formaldehyde and volatility in the processing of carbamate finishes.
• methylol derivatives of ethyl and methyl carbamate will completely volatize when exposed to temperatures of about 200 F. However, when they are further reacted With ethylene or propylene urea between 50%60% of the reaction product does not volatize.
• methylol derivatives of methyl, ethyl, propyl, hydroxy ethyl, methoxy ethyl and butyl carbamate are further reacted with glyoxal and urea, the resulting product does not volatilize even when exposed to temperatures of 300 F. for 30 minutes.
• the amount of formaldehyde may vary from 2 to 2.5 moles, the preferred amount being 2.25 moles.
• the pH must be adjusted to about 10 by the use of an alkali, for example, sodium hydroxide, potassium hydroxide, sodium carbonate, etc.
• Reaction is continued for about 1' /2 hours at 10 pH. It was found to be of importance that the pH should not drop below 9.5.
• the degree of methylolation is usually between and The reaction temperature is about F. to F.
• the resulting product is cooled to 120 F. and pH is adjusted to 4.0 by the use of maleic acid, citric acid, tartaric acid or hydrochloric acid. Maleic acid is preferred.
• the product is held at a pH of 4.0 at 120 F. for about one hour.
• reaction takes place with glyoxal and urea
• the pH is adjusted to from 4 to about 5 with caustic soda solution; the product is heated for 3 to 3%. hours and then cooled. No further adjustment is necessary.
• the free residual formaldehyde amounts to less than 1% and the product does not volatilize even at high temperatures.
• Experimentation with various amounts of glyoxal and urea has indicated that the amount of free formaldehyde decreases if a somewhat larger amount of urea in relation to glyoxal is used, namely for 1 mole glyoxal the urea should preferably be in the range of about 1.3 to 1.4 moles.
• EXAMPLE 1 75 gr. methyl carbamate (1 mole) are reacted with 183 gr. (2.25 moles) of 37% formaldehyde. 0.45 gr. sodium hydroxide are added to adjust the pH to 10.3. The reaction is continued for 1% hours at 158 P. Then the product is cooled to 113 F. About 1 gr. maleic acid is added to adjust the pH to 4.0. At this stage 1.71 moles of formaldehyde have been reacted, leaving 0.54 mole free formaldehyde.
• the resulting product is practically water white. It contains from 0.5% to 1.0% free formaldehyde and it will not volatilize at 300 F. for minutes. It is most effective as a finish for cotton fabrics and cotton polyester blend fabrics.
• EXAMPLE 2 103. gr. (1 mole) propyl carbamate are reacted with 183 gr. (2.25 moles) of 37% formaldehyde. 0.45 gr. sodium hydroxide are added to adjust the pH to 10.3. The reaction is continued for 2 hours at 158 F. Then the product is cooled to 113 F. 1 gr. maleic acid is added to change the pH to 4.0. At this stage 1.75 moles of formaldehyde have been reacted, leaving 0.5 mole of formaldehyde free.
• Sodium hydroxide is added to set pH at 5.0. 40.7 gr. (0.27 mole) of 40% glyoxal are added along with an amount of urea which may vary from 16.2 gr. (0.27 mole) to 21 gr. (0.35 mole). The reaction is continued for about 2 hours at about 175 F. The resulting product contains 0.5% to 1.0% free formaldehyde, it will not volatilize readily and it produces an excellent finish.
• EXAMPLE 4 119 gr. (1 mole) methoxy ethyl carbamate are reacted with 183 gr. (2.25 moles) of 37% formaldehyde. 1 gr. potassium hydroxide is added to adjust the pH to 10.2. The reaction is continued for 1% hours at F. Then the product is cooled to 113 F. Citric acid is added to set the pH at 4.0. At this stage 1.7 moles of formaldehyde have been reacted, leaving 0.55 mole of free formaldehyde.
• Fabrics which are those finished have excellent crush resistance and dimensional control as well as all other advantageous properties which are at least as good as those imparted to fabrics by prior art carbamate finishes. Furthermore, they have the additional advantages as compared to prior art carbamate finishes, that the amount of free formaldehyde is reduced to a negligible quantity and that the finish is non-volatile. Accordingly, the carbamate finishes of this invention can be used satisfactorily in permanent press processing.
• a finish for textile fabrics comprising a material resulting from a first reaction of one molar part of a carbamate compound selected from the group consisting of methyl carbamate, ethyl carbamate, propyl carbamate, methoxy-ethyl carbamate, hydroxy-ethyl carbamate and butyl carbamate with more than two molar parts of formaldehyde under reaction conditions of elevated temperature and alkaline pH and carrying forward said reaction as far as it will go and thence reacting all of the excess formaldehyde from said first reaction and in the presence of said product of said first reaction in a second reaction with a sufiicient amount of a compound selected from the group consisting of ethylene urea, propylene urea and combined glyoxal and urea at elevated temperatures and at a pH of from 5 to 9 and carrying forward said second reaction as far as it will go.
• a carbamate compound selected from the group consisting of methyl carbamate, ethyl
• a finish for textile fabrics as described in claim 1 the reactant used to react with said excess formaldehyde from said first reaction being combined glyoxal and urea in proportion of one molar part of glyoxal to at least 1.3 molar parts of urea.

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

Applications Claiming Priority (1)

Publications (1)

Family

ID=24448345

Family Applications (1)

Country Status (3)

Cited By (14)

• 1967
  • 1967-01-24 US US3590100D patent/US3590100A/en not_active Expired - Lifetime
  • 1967-04-28 BE BE697759D patent/BE697759A/xx unknown
  • 1967-06-16 NL NL6708395A patent/NL6708395A/xx unknown

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