US4439203A — Process for improving the wetfastness of dyeings,…

Claim 1

Independent Claim 271 words

A process for improving the fastness properties of a dyestuff or optical brightener on a substrate comprising hydroxy group-containing fibers, which process comprises applying to a dyed, printed or brightened substrate a composition comprising IV. a water soluble precondensate produced by reacting (A) with (B), V. a water-soluble precondensate produced by reacting (A) and (B) together with (E), VI. a water-soluble precondensate produced by reacting (A) with (C) in an aqueous medium at 20°-60° C., VII. a water-soluble precondensate produced by reacting (A) and (C) together with (E), VIII. a water-soluble precondensate produced by reacting (A) with (D), or IX. a water-soluble precondensate produced by reacting (A) and (D) together with (E), each of V, VI, VII, VIII and IX being in combination with a catalyst (F) and IV optionally being in combination with a catalyst (F) wherein (A) is the product of reacting a mono- or polyfunctional primary or secondary amine with cyanamide, dicyandiamide, guanidine or biguanidine; with the proviso that up to 50 mole % of the cyanamide, dicyandiamide, guanidine or biguanide may be replaced with a dicarboxylic acid or a mono- or di-ester thereof, said product (A) containing reactive hydrogen atoms bound to nitrogen, (B) is an epihalohydrin or a precursor thereof, (C) is formaldehyde or a formaldehyde precursor, (D) is a dihydroxyalkyleneurea or a methyl ether thereof, followed by formaldehyde or a formaldehyde precursor (E) is a member selected from the group consisting of N,N'-dimethylol-4,5-dihydroxy-ethyleneurea, N,N'-dimethylol-4,5-dimethoxy-ethyleneurea, N,N'-dimethylol-4-methoxy-5,5-dimethyl-propyleneurea, N,N'-dimethylol-carbamates and the ethers of said compounds, and (F) is a catalyst for the cross-linking of N-methylol compounds of the type (E) above, and subsequently carrying out a cross-linking step.

Claim 2

Dependent Claim 271 words

A process for improving the fastness properties of a dyestuff or optical brightener on a substrate comprising hydroxy group-containing fibers, which process comprises applying to a dyed, printed or brightened substrate a composition comprising IV. a water soluble precondensate produced by reacting (A) with (B), V. a water-soluble precondensate produced by reacting (A) and (B) together with (E), VI. a water-soluble precondensate produced by reacting (A) with (C) in an aqueous medium at 20°-60° C., VII. a water-soluble precondensate produced by reacting (A) and (C) together with (E), VIII. a water-soluble precondensate produced by reacting (A) with (D), or IX. a water-soluble precondensate produced by reacting (A) and (D) together with (E), each of V, VI, VII, VIII and IX being in combination with a catalyst (F) and IV optionally being in combination with a catalyst (F) wherein (A) is the product of reacting a mono- or polyfunctional primary or secondary amine with cyanamide, dicyandiamide, guanidine or biguanidine; with the proviso that up to 50 mole % of the cyanamide, dicyandiamide, guanidine or biguanide may be replaced with a dicarboxylic acid or a mono- or di-ester thereof, said product (A) containing reactive hydrogen atoms bound to nitrogen, (B) is an epihalohydrin or a precursor thereof, (C) is formaldehyde or a formaldehyde precursor, (D) is a dihydroxyalkyleneurea or a methyl ether thereof, followed by formaldehyde or a formaldehyde precursor (E) is a member selected from the group consisting of N,N'-dimethylol-4,5-dihydroxy-ethyleneurea, N,N'-dimethylol-4,5-dimethoxy-ethyleneurea, N,N'-dimethylol-4-methoxy-5,5-dimethyl-propyleneurea, N,N'-dimethylol-carbamates and the ethers of said compounds, and (F) is a catalyst for the cross-linking of N-methylol compounds of the type (E) above, and subsequently carrying out a cross-linking step.

Claim 3

Dependent Claim 106 words

A process according to claim 1 in which component (A) is the product of reacting with dicyandiamide a polyalkylene polyamine of formula I RRN--Z--X).sub.n Z--NRR I in which each R independently is hydrogen or a C 1-10 alkyl group unsubstituted or monosubstituted with hydroxy, C 1-4 alkoxy or cyano, n is a number from 0 to 100 Z, or each Z independently when n>0, is C 2-4 alkylene or hydroxyalkylene and X, or each X independently when n>1, is --O--, --S-- or --NR-- where R is as defined above, provided that the amine of formula I contains at least one reactive --NH-- or --NH 2 group.

Claim 4

Dependent Claim 51 words

A process according to claim 2 wherein component (A) is the product of reacting dicyandiamide with a polyamine of formula I in which each R is hydrogen, n is 0 to 4, X is --NH-- or --NCH 3 -- and Z, or each Z independently when n>0, is C 2-4 alkylene.

Claim 5

Dependent Claim 21 words

A process according to claim 1 in which a precondensate of component (A) with component (B) is applied to the substrate.

Claim 6

Dependent Claim 33 words

A process as claimed in claim 3, employing a precondensate of (A) and (B), in which application is by exhaust and the cross-linking step takes place in the exhaust bath under alkaline conditions.

Claim 7

Dependent Claim 23 words

A process according to claim 3 wherein the precondensate is one produced at pH 6-9 and the substrate is cotton or viscose rayon.

Claim 8

Dependent Claim 28 words

A process as claimed in claim 1 in which catalyst (F) is present, the precondensate is applied by padding, and the cross-linking step is carried out by heat-curing.

Claim 9

Dependent Claim 14 words

A process according to claim 1 wherein the substrate is cotton or viscose rayon.

Claim 10

Dependent Claim 179 words

A process according to claim 1 wherein (A) is the product of reacting cyanamide, dicyandiamide or guanidine with a polyamine of formula I RRN--Z--X).sub.n Z--NRR I in which each R, independently, is hydrogen or a C 1-10 alkyl group unsubstituted or monosubstituted with hydroxy, C 1-4 alkoxy or cyano, n is a number from 0 to 100 Z, or each Z independently when n>0, is C 2-4 alkylene or hydroxyalkylene and X, or each X independently when n>1, is --O--, --S-- or --NR-- where R is as defined above, provided that the amine of formula I contains at least one reactive --NH-- or --NH 2 group, (B) is epichlorohydrin or dichlorohydrin, (C) is formaldehyde or paraformaldehyde, (D) is dihydroxyethyleneurea or its methyl ether followed by formaldehyde or paraformaldehyde, and (F) is selected from the nitrates, sulphates, chlorides, tetrafluoroborates and dihydrogen orthophosphates of aluminum, magnesium and zinc; aluminum hydroxycloride; zirconyl oxychloride; alkali metal bisulphites; 2-amino-2-methylpropanol hydrochlorides; citric, oxalic, maleic, glycollic and trichloracetic acids; phosphoric and hydrochloric acids; ammonium nitrate, chloride, sulphate and oxalates; mono- and di-ammonium orthophosphate; and mixtures thereof.

Claim 11

Dependent Claim 18 words

A process according to claim 9 wherein component (E), when an ether, is a methyl or ethyl ether.

Claim 12

Dependent Claim 14 words

A process according to claim 7 wherein the substrate is cotton or viscose rayon.

Claim 13

Dependent Claim 119 words

A process according to claim 11 wherein i. (A) is the product of reacting 0.1 to 1 mol of cyanamide, dicyandiamide, guanidine or biguanidine per mol of reactive --NH-- or --NH 2 groups in the polyamine, with the proviso that up to 50% of said amount of cyanamide, dicyandiamide, guanidine or biguanidine may be replaced by adipic acid, oxalic acid, terephthalic acid or a dimethyl ester of said acids; ii. the mol ratio of (A) to (B) is 1:0.3-2; iii. The mol ratio of (A) to (C) is 1:2-6, based on the number of mols of amine originally present iv. the amount of (E), when present, is 50 to 200 % of the weight of (A)+ (B) or (A)+(C).

Claim 14

Dependent Claim 132 words

A process for producing a product useful as an aftertreatment agent for improving the fastness of a dyeing, printing or optical brightening on a hydroxy group-containing substrate which comprises reacting (A) the product of reacting a mono- or polyfunctional primary or secondary amine with cyanamide, dicyandiamide, guanidine or biguanidine; with the proviso that up to 50 mole % of the cyanamide, dicyandiamide, guanidine or biguanidine may be replaced with a dicarboxylic acid or a mono- or di-ester thereof, said product (A) containing reactive hydrogen atoms bound to nitrogen, with a dihydroxyalkyleneurea or methyl ether thereof in an aqueous medium at a temperature between room temperature and 80° C., and reacting the resulting product with formaldehyde under acid conditions, the proportions of A:dihydroxyalkyleneurea:formaldehyde being 5-40:25-110:1-60 based on the dry weight of active component.

Claim 15

Dependent Claim 132 words

A process for producing a product useful as an aftertreatment agent for improving the fastness of a dyeing, printing or optical brightening on a hydroxy group-containing substrate which comprises reacting (A) the product of reacting a mono- or polyfunctional primary or secondary amine with cyanamide, dicyandiamide, guanidine or biguanidine; with the proviso that up to 50 mole % of the cyanamide, dicyandiamide, guanidine or biguanidine may be replaced with a dicarboxylic acid or a mono- or di-ester thereof, said product (A) containing reactive hydrogen atoms bound to nitrogen, with a dihydroxyalkyleneurea or methyl ether thereof in an aqueous medium at a temperature between room temperature and 80° C., and reacting the resulting product with formaldehyde under acid conditions, the proportions of A:dihydroxyalkyleneurea:formaldehyde being 5-40:25-110:1-60 based on the dry weight of active component.

Claim 16

Dependent Claim 189 words

A composition useful for the aftertreatment of a dyed, printed or brightened substrate comprising hydroxy group-containing fibers, which composition comprises V. a water-soluble precondensate produced by reacting (A) and (B) together with (E), VI. a water-soluble precondensate produced by reacting (A) with (C) in an aqueous medium at 20°-60° C., or VII. a water-soluble precondensate produced by reacting (A) and (C) together with (E), each of V, VI and VII being in combination with a catalyst (F), wherein (A) is the product of reacting a mono- or polyfunctional primary or secondary amine with cyanamide, dicyandiamide, guanidine or biguanidine; with the proviso that up to 50 mole % of the cyanamide, dicyandiamide, guanidine or biguanidine may be replaced with a dicarboxylic acid or a mono- or di-ester thereof, said product (A) containing reactive hydrogen atoms bound to nitrogen, (B) is a epihalohydrin or a precursor thereof, (C) is formaldehyde or a formaldehyde precursor, (E) is a member selected from the group consisting of N,N'-dimethylol-4,5-dihydroxy-ethyleneurea, N,N'-dimethylol-4,5-dimethoxy-ethyleneurea, N,N'-dimethylol-4-methoxy-5,5-dimethyl-propyleneurea, N,N'-dimethylol carbamates and the ethers of said compounds, and (F) is a catalyst for the cross-linking of N-methylol compounds of the type (E) above.

Claim 17

Dependent Claim 189 words

A composition useful for the aftertreatment of a dyed, printed or brightened substrate comprising hydroxy group-containing fibers, which composition comprises V. a water-soluble precondensate produced by reacting (A) and (B) together with (E), VI. a water-soluble precondensate produced by reacting (A) with (C) in an aqueous medium at 20°-60° C., or VII. a water-soluble precondensate produced by reacting (A) and (C) together with (E), each of V, VI and VII being in combination with a catalyst (F), wherein (A) is the product of reacting a mono- or polyfunctional primary or secondary amine with cyanamide, dicyandiamide, guanidine or biguanidine; with the proviso that up to 50 mole % of the cyanamide, dicyandiamide, guanidine or biguanidine may be replaced with a dicarboxylic acid or a mono- or di-ester thereof, said product (A) containing reactive hydrogen atoms bound to nitrogen, (B) is a epihalohydrin or a precursor thereof, (C) is formaldehyde or a formaldehyde precursor, (E) is a member selected from the group consisting of N,N'-dimethylol-4,5-dihydroxy-ethyleneurea, N,N'-dimethylol-4,5-dimethoxy-ethyleneurea, N,N'-dimethylol-4-methoxy-5,5-dimethyl-propyleneurea, N,N'-dimethylol carbamates and the ethers of said compounds, and (F) is a catalyst for the cross-linking of N-methylol compounds of the type (E) above.

Claim 18

Dependent Claim 24 words

An aftertreatment agent according to claim 14 comprising a precondensate of component (A) with formaldehyde or a precursor thereof (C), together with catalyst (F).

Claim 19

Dependent Claim 12 words

An aftertreatment agent according to claim 15, in admixture with component (E).

Claim 20

Dependent Claim 19 words

A composition according to claim 14 prepared by reacting (A), (B) and (E) in the presence of catalyst (F).

Claim 21

Dependent Claim 19 words

A composition according to claim 14 prepared by reacting (A), (C) and (E) in the presence of catalyst (F).

Claim 22

Dependent Claim 107 words

A composition according to claim 14 wherein component (A) is the product of reacting cyanamide, dicyandiamide or guanidine with a polyamine of formula I RRN--Z--X).sub.n Z--NRR I in which each R, independently, is hydrogen or a C 1-10 alkyl group unsubstituted or monosubstituted with hydroxy, C 1-4 alkoxy or cyano, n is a number from 0 to 100 Z, or each Z independently when n>0, is C 2-4 alkylene or hydroxyalkylene and X, or each X independently when n>1, is --O--, --S-- or --NR-- where R is as defined above, provided that the amine of formula I contains at least one reactive --NH-- or --NH 2 group.

Claim 23

Dependent Claim 51 words

A composition according to claim 16 wherein component (A) is the product of reacting dicyandiamide with a polyamine of formula I in which each R is hydrogen, n is 0 to 4, X is --NH-- or --NCH 3 -- and Z, or each Z independently when n>0 is C 2-4 alkylene.

Claim 24

Dependent Claim 117 words

A composition according to claim 16 wherein i. (A) is the product of reacting 0.1 to 1 mol of cyanamide, dicyandiamide, guanidine or biguanidine per mol of reactive --NH-- or --NH 2 groups in the polyamine, with the proviso that up to 50% of said amount of cyanamide, dicyandiamide, guanidine or biguanidine may be replaced by adipic acid, oxalic acid, terephthalic acid or a dimethyl ester of said acids; ii. the mole ratio of (A) to (B) is 1:0.3-2; iii. the mol ratio of (A) to (C) is 1:2-6, based on the number of mols of amine originally present iv. the amount of (E), when present, is 50 to 200% of the weight of (A)+(B) or (A)+(C).

Claim 25

Dependent Claim 73 words

A composition according to claim 16 wherein (B) is epichlorohydrin or dichlorohydrin (C) is formaldehyde or paraformaldehyde with an aimne of formula II (F) is selected from the nitrates, sulphates, chlorides, tetrafluoroborates and dihydrogen orthophosphates of aluminium, magnesium and zinc; aluminium hydroxychloride; zirconyl oxychloride; alkali metal bisulphites; 2-amino-2-methylpropanol hydrochloride; citric, oxalic, maleic, glycollic and trichloroacetic acids; phosphoric and hydrochloric acids; ammonium nitrate, chloride, sulphate and oxalate; mono- and di-ammonium orthophosphate; and mixtures thereof.

Claim 26

Dependent Claim 117 words

A composition according to claim 19 wherein i. (A) is the product of reacting 0.1 to 1 mol of cyanamide, dicyandiamide, guanidine or biguanidine per mole of reactive --NH-- or --NH 2 groups in the polyamine, with the proviso that up to 50% of said amount of cyanamide, dicyandiamide, guanidine or biguanidine may be replaced by adipic acid, oxalic acid, terephthalic acid or a dimethyl ester of said acids; ii. the mol ratio of (A) to (B) is 1:0.3-2; iii. the mole ratio of (A) to (C) is 1:2-6, based on the number of mols of amine originally present iv. the amount of (E), when present, is 50 to 200% of the weight of (A)+(B) or (A)+(C).

Claim 27

Dependent Claim 18 words

A composition according to claim 22 wherein component (E), when an ether, is a methyl or ethyl ether.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1987-03-27	1987-09-26	1988-03-27	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1991-03-27	1991-09-26	1992-03-27	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	1995-03-27	1995-09-26	1996-03-27	$7700.00	Window Closed / Lapsed

Process for improving the wetfastness of dyeings, printings and optical brightenings on cellulosic substrates and compositions useful therefor

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