Classifications

• • 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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
  • C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
  • C07C273/189—Purification, separation, stabilisation, use of additives
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/16—Nitrogen-containing compounds
• • 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
  • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
  • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
  • D06M13/35—Heterocyclic compounds

Definitions

• methylol compounds of urea may be used as agents for textile finishing, particularly for creaseresist finishing and shrink-resist finishing of textiles which consist of or contain cellulose.
• Monomethylolurea can also be prepared in solid form, but like dimethylolurea it has in adequate stability in storage.
• textile finishing agents which may have been spray-dried and which are solid mixtures containing a maximum of 0.3% by weight of free formaldehyde, contain urea and/or monomethylolurea and dimethylolurea in such amounts that the molar ratio of free and combined urea to combined formaldehyde is from 121.4 to 1:1.85, have much better watersolubility and stability than the abovementioned agents.
• these agents may be stored satisfactorily even under unfavorable conditions, however, it is sometimes desirable to further improve their stability in the solid condition.
• a spray-dried textile finishing agent containing as active component at least one methylol compound of urea is superior to all the abovementioned agents of this type in storage stability when it contains 2 to 8%, preferably 3 to 6%, by weight (with reference to the methylol compounds of urea) of at least one substance having the general formula:
• ZC O iZ-IC in which Z denotes one of the radicals NH and N(CH OH), X denotes one of the radicals NH, N(CH OH)-, CH and 0- and Y denotes a 1,2-alkylene radical, 1,3-alkylene radical or 1,4-alkylene radical which may bear hydroxyl groups, alkyl groups and/or alkoxyl groups each bearing up to four carbon atoms as substituents, and not more than 2% by weight of water.
• epsilon-caprolactam and derivatives of the said substances which are wholly or partly substituted by methylol groups, i.e. hydroxymethyl groups, on the nitrogen atoms.
• Substances having the Formula I are contained in the agents according to this invention in amounts of 2 to 8%, preferably 3 to 6%, by Weight with reference to the methylol compounds of urea. They may be added at any time during the production of the agents, particularly prior to or during the spray drying. It is preferable to add them to the aqueous mixture which is to be spray-dried, during or after the reaction of urea with formaldehyde.
• the agent according to this invention may be prepared by conventional methods.
• urea and formaldehyde may be reacted with each other in a molar ratio of 1:1.4 to 1:22 in aqueous solution at a pH value of 6.5 to 9 and at a temperature of up to C. and the reaction product supplied to a spray dryer, the substances having the Formula I being added either during the dissolution of the urea, or after the formaldehyde has been added at any stage of the reaction, or after the reaction is over immediately prior to or during spray drying.
• Urea and formaldehyde are reacted with each other in a molar ratio of 1:1.4 to 1:1.85, preferably 1: 1.55 to 1:1.8, with or without adding the abovementioned amounts of substances having the Formula I, in aqueous solution at a pH value of 6.5 to 8.5, preferably 7.0 to 8.0, and at a temperature of 30 to 40 C. for up to five hours, preferably from half an hour to two hours, the reaction mixture is cooled to 15 to 28 C., stirred for at least 24 hours, preferably for 30 to 70 hours, at the said temperature (the substance having the Formula I being if desired added at this point and not earlier) and the resultant crystal slurry is subjected to spray drying.
• an alkaline-reacting substance is used; medium-strength organic bases are particularly suitable for this purpose because when the'y are used end products are obtained which are particularly stable in storage.
• bases are: low molecular weight alkanolamines, particularly those having up to six carbon atoms in the molecule, such as triethanolamine, diethanolamine, N-methylethanolamine and N-dimethylethanolamine.
• the crystal slurry intended for spray drying prefferably has a dry residue of at least 30% by weight.
• Products having particularly good stability in storage are obtained from crystal pastes having a dry residue of 40 to 50% by weight; these pastes can also be easily conveyed and atomized.
• the production of the crystal pastes may be carried out batchwise or continuously for example in a cascade of stirred vessels.
• Drying the crystal slurry in order to obtain the end product may be carried out in nozzle or disc spray dryers. It has proved to be particularly advantageous for the inlet temperature of the spray dryer to be from 135 to 170 C., preferably from 140 to 160 C., and for the outlet temperature of the spray dryer to be from 50 to 80 0., preferably from 60 to 75 C. It is advantageous to cool the material discharge from the dryer as quickly as possible to a temperature of 40 C. or less, for example by means of a cooling channel.
• agents according to this invention have much better stability in storage than agents which do not contain substances having Formula I but are otherwise identical. Moreover their aqueous solutions, particularly in concen trated form, have a considerably better storage life; stock solutions of the agents according to this invention may therefore be kept for days without detriment.
• EXAMPLE 1 60 parts of urea is mixed with 40 parts of water and such an amount of 35% aqueous formaldehyde solution is added thereto that the molar ratio of urea to formaldehyde is 1:17 A solution having a substance content of 45% is obtained. Half of the mixture has 6% of pyrrolidone-2 added to it with reference to the substance contained in the solution. Both halves are adjusted to a pH value of 7.5 to 7.7 with triethanolamine, condensed for two hours at 35 C. and then allowed to crystallize while being stirred for sevent'y hours at 21 to 25 C. The crystal slurries obtained are spray-dried, the inlet temperature of the dryer being 150 C. and the outlet temperature being 70 C. The powder obtained contains 1.2% of water in the case of the product free from pyrrolidone and 1.4% of water in the case of the product containing pyrrolidone according to the invention.
• Both products dissolve in water without any residue immediately after their production. They are then stored for forty days at 40 C. After this period, the agent according to the invention contains 0.16% of constituents which are insoluble in water while the agent free from pyrrolidone contains 1% of constituents which are insoluble in water.
• EXAMPLE 2 60 parts of urea, 40 parts of water and such an amount of 35% aqueous formaldehyde solution are mixed that the molar ratio of urea to formaldehyde is 1:1.75; the mixture is adjusted to a pH value of 7.8 with triethanolamine, condensed for one hour at 35 C. and then allowed to crystallize for sixty-nine hours at 20 to 24 C. while stirring. 2% of pyrrolidone (with reference to the solids contained therein) is added to half of the mixture. One hour later the two halves are spray-dried as described in Example 1.
• the samples which give clear solutions in water and which contain 0.92% of water (product free from pyrrolidone) and 0.84% of water (product according to this invention) are stored for fifty days at 40 C. After this period the agent according to this invention contains 0.4% of constituents which are insoluble in water while the agent free from pyrrolidone contains 1.33% of water-insoluble constituents.
• Example 3 The procedure of Example 2 is followed but omitting pyrrolidone-2 (sample 1). Further samples are prepared in the same way. Samples 2 and 3 have 3% and 5% of imidazolidone-2 added to them prior to condensation and Samples 4 and 5 have 3% and 5% of imidazolidone-2 added to them one hour prior to spray drying. All the samples are free from water-insoluble constituents immediately after the spray drying. They contain the following amounts of water:
• the samples are kept at 40 C. for seven weeks. After this period they contain the following amounts of waterinsoluble constituents.
• the agents according to this invention are therefore more stable in storage than the agent free from additive although they contain more water.
• Example 5 The procedure of Example 2 is followed but omitting the pyrrolidone-2. One-half of the mixture has 6% (with reference to the solids content) of epsilon-caprolactam added to it prior to condensation (Sample 2), while the other half is processed without additive (Sample 1). The samples obtained had the following water contents and,
• EXAMPLE 6 An aqueous solution of urea and formaldehyde (molar ratio 1:1.75, solids content 46%) is adjusted to a pH value of 7.6 with triethanolamine, kept for sixty minutes at 35 C. and then stirred for three days at 22 to 25 C. The aqueous suspension of crystals is divided into four parts. Sample 1 is spray-dried, without adadditive, at a dryer inlet temperature of 150 C.
• Sample 2 is spray-dried under the same conditions after an addition of 6% of hexahydropyrirnidone-Z (with reference to the solids content in the aqueous suspension);
• Sample 3 is spray-dried after an addition of 3% of 4,5-dihydroxyimidazolidone-2; and
• Sample 4 is spray dried after an addition of 4% of N- hydroxymethylpyrrolidone.
• the powders obtained by the spray drying are all soluble in water (140 g./l.) without residue. They have the following properties:
• EXAMPLE 7 1000 parts of a methylolurea spray-dried product prepared by spray drying a 45% aqueous methylolurea paste (which has been prepared by reaction of urea and formaldehyde for two hours in the molar ratio 1:1.75 at 35 C., stirring at room temperature for fifty hours and adjustment to pH 7.5 with triethanolamine (is well mixed with 30 parts of finely powdered imidazolidone-Z. Both the starting product and the mixture are soluble in water without residue. After storage for four weeks at 40 C., the starting product contains 0.6% of water-insoluble constituents while the mixture contains only 0.3%.
• a spray-dried agent for textile finishing having improved stability in storage which consists essentially of:
• component (b) 2 to 8% by weight with reference to component (a) of at least one substance having the formula:
• Z denotes a radical selected from the group consisting of NH and -N(CH OH)--
• X denotes a radical selected from the group consisting of NH, N(CH OH), CH and -O-
• Y denotes a divalent radical selected from the group consisting of alkylene of 2 to 4' carbon atoms and said alkylene substituted by at least one of the radicals: hydroxyl, alkyl having one to four carbon atoms and alkoxyl having one to four carbon atoms, as stabilizer, and
• An agent as claimed in claim 1 which contains 3 to 6% by weight of component (b) with reference to component (a).
• a process for the production of a textile-finishing agent which comprises:

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

Applications Claiming Priority (1)

Publications (1)

Family

ID=6984735

Family Applications (1)

Country Status (8)

Cited By (4)

Families Citing this family (1)

• 1966
  • 1966-10-13 DE DE19661594916 patent/DE1594916A1/de active Pending
• 1967
  • 1967-10-11 CH CH1415767A patent/CH479752A/de not_active IP Right Cessation
  • 1967-10-12 GB GB46579/67A patent/GB1192990A/en not_active Expired
  • 1967-10-13 SE SE14067/67A patent/SE317943B/xx unknown
  • 1967-10-13 AT AT929367A patent/AT273880B/de active
  • 1967-10-13 US US675013A patent/US3651139A/en not_active Expired - Lifetime
  • 1967-10-13 BE BE705052D patent/BE705052A/xx unknown
  • 1967-10-13 NL NL6713955A patent/NL6713955A/xx unknown

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