Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From carboxylic acid or derivative thereof
Reexamination Certificate
1999-05-14
2001-10-23
Hampton-Hightower, P. (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From carboxylic acid or derivative thereof
C528S243000, C528S254000, C528S257000, C528S268000, C008S115510, C008S115600, C008S116100, C008S536000, C008S543000, C008S556000
Reexamination Certificate
active
06307007
ABSTRACT:
The invention relates to water soluble polycondensation products which are produced by the reaction of polyfunctional amines with cyanamide or its derivatives and polymers.
BACKGROUND OF THE INVENTION
Such reaction products as well as their use for the improvement of fastness properties of dyeings with substantive dyestuffs have long been known. Thus DE-A-855 001 describes polycondensates obtained by heating a polyfunctional amine with cyanamide or a polymer or a derivative thereof in the absence of water, optionally in the presence of non-aqueous solvents, under elimination of ammonia. According to EP-A-0 431 423 these products contain, due to the process by which they are produced, water-insoluble by-products, a drawback which can be eliminated by carrying out the condensation between the polyfunctional amine and the cyanamide or its derivative or polymer in the presence of ammonium salts, such as ammonium chloride, sulfate, carbonate, formiate or acetate, in the absence or presence of a non-aqueous solvent, preferably in the presence of a solvent containing hydroxy groups and having a boiling point above 180° C. According to EP-A-0 692 511 an advantageous modification of this process consists of reacting the polyfunctional amine with the ammonium salt in the presence of a non-aqueous solvent and heating the protonised product thus obtained with the cyanamide component; this embodiment improves the safety of the process.
JP-A-60 252 787 describes wet fastness boosters for cellulose fiber dyed material, comprising the product of a polycondensation of an aliphatic diamine having 6 or more carbon atoms, preferably 1,6-hexanediamine or 2,2,4-trimethylhexamethylenediamine, or a salt thereof with an inorganic acid or an organic acid (such as formic, acetic and sulfamic acid), preferably the hydrochloride, with a guanidine compound or a salt thereof, preferably dicyandiamide, guanidine hydrochloride or guanidine sulfate. The resulting polycondensates are stated to have improved fastness-providing properties as compared with similar products obtained from other diamines.
SUMMARY OF THE INVENTION
It has been found that water-soluble condensation products with excellent properties are obtained if the reaction of amines with cyanamide, its derivatives or polymers is performed in the presence of 0.1 to 0.7 mol of sulfamic acid, or its salts, per mol of the cyanamide component.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The invention, therefore, relates to water-soluble basic polycondensation products obtained by the reaction of
A) an amine of formula (I)
in which
A is an alkylene chain optionally interrupted by a hetero atom, and
R
1
-R
4
are independently selected from hydrogen, alkyl optionally substituted by OH, CN or C
1
-C
4
-alkoxy, provided that at least one of R
1
to R
4
is hydrogen, with
B) cyanamide, its derivatives or polymers in a mol ratio of A:B=2:1 to 1:2, preferably 1:1 to 1:1.5 in the presence of
C) 0.1 to 0.7 mol sulfamic acid, or its salts, per mole of B, at temperatures of 80 to 180° C., preferably 130 to 160° C.,
and their water-soluble salts obtained by neutralization with inorganic or organic acids usual in the dyeing technique.
Preferred amines of formula (I) are those in which
A is an C
2
-C
20
-alkylene chain optionally interrupted by O, S, NH or N—C
1
-C
4
-alkyl or substituted by OH, and
R
1-R
4
are independently hydrogen or C
1
-C
4
-alkyl, provided that at least one of R
1
to R
4
is hydrogen.
Examples of suitable polyfunctional amines A are 1,4-butanediamine, 1,6-hexanediamine, N-(2-aminoethyl)-1,3-propanediamine, dipropylenetriamine, N,N-bis-(2-aminopropyl)-methylamine, polyethylenimine and preferably polyethylenpolyamines such as triethylene-tetramine, tetraethylenepentamine, pentaethylenehexamine and most preferably diethylene-triamine.
Suitable components B are cyanamide, dicyandiamide, guanidine and biguanidine. Dicyandiamide is preferred. Component C is preferably free sulfamic acid.
The reaction of component A with component B is performed in a mol ratio of 2:1 to 1:2, preferably 1:1 to 1:1.5 in the presence of 0.1 to 0.7 mol sulfamic acid at temperatures of 80 to 180° C., preferably 130 to 160° C., in the molten state whereby ammonia is split off. According to one possible variant of this process, Lewis acids, e.g. zinc chloride are used as catalysts.
It is also possible to use a suitable solvent, preferably one containing hydroxy groups and with boiling point above 180° C., to improve the stirrability of the mixture during condensation. In general, the condensation reaction is performed until no further ammonia is generated or is stopped after obtaining the desired level of viscosity. To counteract the influence of iron ions when performing the condensation in iron vessels, it is advisable to add a phosphonic acid sequestrant in appropriate amounts.
The reaction products are highly viscous liquids or solids with basic properties which dissolve in water to provide clear solutions. Preferably, they are transformed into water-soluble salts by neutralization with inorganic or organic acids as usual in the dyeing technique. Preferred acids are sulfuric, hydrochloric and acetic acid.
The basic polycondensation products or their salts according to the invention are useful for pretreatment or aftertreatment of textile fibers of hydroxy group or amino group containing materials which are dyed or printed with direct or reactive dyestuffs. Such textile fibers can also consist of mixtures of natural and synthetic fibers, e.g. mixtures of cellulose and polyester, polyacrylonitrile, polyamide or wool. The pretreatment of such fibers with the basic polycondensation products improves their dyeability and makes the dyeings more exhaustive, the aftertreatment improves the wet fastness of the dyeings and printings and more specifically the fastness to perspiration, to water and to washing.
The basic polycondensation products or their salts are also useful fixing agents for anionic dyes on paper, board and non-wovens. The treatment with such fixing agents results in better retention of the dye on the fibers or substrate, giving higher color yield and clearer backwater. In addition, the bleedfastness properties of such dyeings are superior to those of the unfixed dyeings. In comparison to fixing agents of the prior art, the advantages of the fixing agents according to the invention are brighter shades of the dyeings (less influence on the shade of the dyeings) and better light-fastness (less negative effect on this parameter).
The fixing agents according to the invention, when applied on paper, are also useful for improving colored two-sidedness with both anionic and cationic dyes (e.g. cationic direct dyes), and for improving color yield with cationic direct dyes where recycled raw materials are used or there are large amounts of filler or fines present.
For the treatment of the substrates with the fixing agents according to the invention, the substrates are treated with aqueous solutions of the basic polycondensation products or, preferably, their salts with inorganic or organic acids. The amounts of polycondensation products or their salts can vary in broad ranges. In general, amounts of 0.1 to 4% by weight, preferably 0.5 to 3% by weight, based on the weight of the substrate, are suitable to obtain the desired effect.
The treatment is performed by immersing the textile fibers either before or after the dyeing process in aqueous treatment baths containing the basic polycondensation products or preferably their salts with inorganic or organic acids. Such treatment of dyed or printed fiber material for improving the wet fastness is typically performed in an exhaustion process whereby the materials stay for 20 to 30 minutes in the aqueous bath containing the basic polycondensation product at pH values from e.g. 4 to 8, preferably 5.5 to 6.5 and temperatures from 20 to 70° C. Alternatively, the aftertreatment is performed continuously in that the aqueous bath is applied by padding and fixation takes place in conventional ways.
If paper, board or non-w
Heller Jurg
Tindal Alec
Clariant Finance (BVI) Limited
Hampton-Hightower P.
Hanf Scott E.
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