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US4410652A Expired / Lapsed US ⏱️ 0.0 years remaining

Reaction products useful for improving the wetfastness of direct and reactive dyes on cellulosic substrates

Assignee: Fidelity Union Bank
•
Filing: 1982-02-09
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Granted: 1983-10-18
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Expires: 2002-02-09
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Abstract

Abstract The wet fastness of direct dyes on cellulose substrates is improved by after-treatment with the reaction product of an amine with cyanamide, dicyanodiamide, guanidine or biguanidine which is further reacted with an N-methylol resin precursor, and heat curing in the presence of a catalyst. The unfixed portion of reactive dyes substantive to cellulose may also be given improved wet fastness by this treatment, so that washing to remove unfixed reactive dye may not be necessary.

Inventors

  • 👤 Tibor Robinson
  • 👤 Walter Knobel
  • 👤 Bruno Kissling

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-25 03:30
CPC Classifications
D; D06; D06P; D06P1/00; D06P1/38; C; C08; C08G; C08G12/00; C08G12/02; C08G12/04; C08G12/043; C08G12/046; C08G12/26; C08G12/34; D06M; D06M15/00; D06M15/19; D06M15/37; D06M15/39; D06M15/423; D06P1/44; D06P1/52; D06P1/5264; D06P1/56; D06P3/00; D06P3/58; D06P3/60; D06P3/62; D06P3/66; D06P5/00; D06P5/02; D06P5/04; D06P5/08

Claims Analysis

Total Claims: 27
Claim 1
Independent Claim 60 words
A water-soluble product obtained by reacting together (A) the product of reacting a mono- or polyfunctional primary or secondary amine in free base or salt form with cyanamide, dicyanodiamide, guanidine or biguanidine; said product containing reactive hydrogen atoms bound to nitrogen, and (B) an N-methylol derivative of a urea, melamine, guanamine, triazinone, urone, carbamate or acid amide in aqueous solution.
Claim 2
Dependent Claim 60 words
A water-soluble product obtained by reacting together (A) the product of reacting a mono- or polyfunctional primary or secondary amine in free base or salt form with cyanamide, dicyanodiamide, guanidine or biguanidine; said product containing reactive hydrogen atoms bound to nitrogen, and (B) an N-methylol derivative of a urea, melamine, guanamine, triazinone, urone, carbamate or acid amide in aqueous solution.
Claim 3
Dependent Claim 34 words
A product according to claim 1 obtained by reacting together reactants (A) and (B) in aqueous solution in the presence of (C) a catalyst for the crosslinking of N-methylol compounds of the type (B).
Claim 4
Dependent Claim 24 words
A product according to claim 2 in which catalyst (C) is selected from nitrates sulphates, chlorides and dihydrogen orthophosphates of aluminium, magnesium and zinc.
Claim 5
Dependent Claim 14 words
A product according to claim 3 in which the catalyst (C) is magnesium chloride.
Claim 6
Dependent Claim 22 words
A product according to claim 1 in which reactant (B) is N,N'-dimethylol-4,5-dihydroxyethyleneurea, N,N'-dimethylol-4,5-dimethoxyethyleneurea, an N,N'-dimethylol carbamate, or a lower alkyl ether thereof.
Claim 7
Dependent Claim 32 words
A product according to claim 1 obtained by reacting together (A) the product of reacting diethylene triamine or triethylene tetramine with dicyanodiamide and (B) N,N'-dimethylol-4,5-dihydroxyethyleneurea in the presence of (C) magnesium chloride.
Claim 8
Dependent Claim 38 words
A product according to claim 1 stabilized against gel formation on storage by the addition of from 1 to 10% by weight of dicyanodiamide, cyanamide, guanidine or biguanidine before, during or after the reaction of (A) with (B).
Claim 9
Dependent Claim 135 words
A product according to claim 1 in which reactant (A) is the reaction product of a monofunctional amine of formula Ia RRNH Ia in which each R is as defined below, provided that at least one is other than hydrogen, or a polyfunctional amine of formula Ib RRN--Z--X--.sub.n Z--NRR Ib 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 1-4 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 Ib contains at least one reactive --NH-- or --NH 2 group, with cyanamide, dicyanodiamide or guanidine.
Claim 10
Dependent Claim 26 words
A product according to claim 8 in which reactant (A) is the reaction product of a polyfunctional amine of formula Ib with cyanamide, dicyanodiamide or guanidine.
Claim 11
Dependent Claim 42 words
A product according to claim 9 in which, in the polyfunctional amine of formula Ib, R is hydrogen or C 1-4 alkyl or hydroxyalkyl, n is a number from 0 to 30, Z is 1,2-ethylene, 1,3-propylene or 1,3-(2-hydroxypropylene) and X is --NR--.
Claim 12
Dependent Claim 27 words
A product according to claim 10 in which, in the polyfunctional amine of formula Ib, R is hydrogen and n is an integer from 1 to 6.
Claim 13
Dependent Claim 24 words
A product according to claim 10 in which reactant (B) is N,N'-dimethylol-4,5-dihydroxyethyleneurea, N,N'-dimethylol-4,5-dimethoxyethyleneurea, an N,N'-dimethylol carbamate; or a lower alkyl ether of said compounds.
Claim 14
Dependent Claim 45 words
A product according to claim 12 which is obtained by reacting (A) and (B) in aqueous solution in the presence of (C) a catalyst suitable for crosslinking N-methylol compounds (B) and selected from the nitrates, sulphates, chlorides and dihydrogen orthophosphates of aluminum, magnesium and zinc.
Claim 15
Dependent Claim 32 words
A product according to claim 13 which is obtained from (A), (B) and (C) in relative amounts of 5-40 parts by weight, 25-110 parts by weight and 1-30 parts by weight, respectively.
Claim 16
Dependent Claim 23 words
A product according to claim 10 in which reactant (A) is the reaction product of a polyfunctional amine of formula Ib with dicyanodiamide.
Claim 17
Dependent Claim 28 words
A product according to claim 15 in which reactant (A) is the product of reacting the dicyanodiamide and the amine in a molar ratio of 2:1 to 1:2.
Claim 18
Dependent Claim 39 words
A product according to claim 8 in which reactant (A) is the product of the reaction of 0.1 to 1 mole of cyanamide, dicyanodiamide, guanidine or biguanidine per mole of reactive --NH or --NH 2 group in the amine.
Claim 19
Dependent Claim 24 words
A product according to claim 17 in which reactant (B) is N,N'-dimethylol-4,5-dihydroxyethyleneurea, N,N'-dimethylol-4,5-dimethoxyethyleneurea, an N,N'-dimethylol carbamate; or a lower alkyl ether of said compounds.
Claim 20
Dependent Claim 32 words
A product according to claim 8, which has a viscosity of 50 to 200 centipoises at room temperature in the presence of water in an amount of 30 to 50% by weight.
Claim 21
Dependent Claim 27 words
A product according to claim 8, in which reactants (A) and (B) are in relative amounts of 5-40 parts by weight and 25-110 parts by weight, respectively.
Claim 22
Dependent Claim 27 words
A product according to claim 20 in which reactants (A) and (B) are in relative amounts of 5-40 parts by weight and 25-110 parts by weight, respectively.
Claim 23
Dependent Claim 38 words
A product according to claim 21 stabilized against gel formation on storage by the addition of from 1 to 10% by weight of dicyanodiamide, cyanamide, guanidine or biguanidine before, during or after the reaction of (A) and (B).
Claim 24
Dependent Claim 60 words
A product according to claim 5 in which reactant (B) is N,N'-dimethylol-4,5-dihydroxyethyleneurea, N,N'-dimethylol-4,5-dimethoxyethyleneurea, an N,N'-dimethylol carbamate, or a lower alkyl ether thereof, the reactants (A) and (B) being reacted in aqueous solution in the presence of (C) a catalyst suitable for crosslinking of N-methylol compounds (B) and selected from nitrates, sulphates, chlorides and dihydrogen orthophosphates of aluminum, magnesium and zinc.
Claim 25
Dependent Claim 32 words
A product according to claim 23 which is obtained from (A), (B) and (C) in relative amounts of 5-40 parts by weight, 25-110 parts by weight and 1-30 parts by weight, respectively.
Claim 26
Dependent Claim 88 words
A product according to claim 8 wherein reactant (B) is selected from the group consisting of N,N'-dimethylolurea; N,N'-dimethylolethyleneurea; N,N'-dimethylolpropyleneurea; N,N'-dimethylol-4,5-dihydroxyethyleneurea; N,N'-dimethylol-4,5-dimethoxyethyleneurea; N,N'-dimethylol-5-hydroxypropyleneurea; N,N'-dimethylol-5-methylpropyleneurea; N,N'-dimethylol-5,5-dimethylpropyleneurea; N,N'-dimethylol-4-hydroxy-5,5-dimethylpropyleneurea; N,N'-dimethylol-4-methoxy-5,5-dimethylpropyleneurea; N,N,N',N'-tetramethylolacetylenediurea; mono- or polymethylol melamine; mono- or polymethylol C 1-12 alkyl or C 6-12 arylguanamine; N,N'-dimethylol-5-C 1-12 alkylhexahydro-1,3,5-triazin-2-one; N,N'-dimethylololurone; C 1-4 alkyl-, C 1-2 alkoxy-C 1-4 alkyl- or hydroxy C 1-4 alkyl N,N'-dimethylol carbamates; C 1-4 alkylene tetramethyl dicarbamates; N-methylol C 1-4 alkylene cyclic carbamates; N,N'-dimethylol acrylamide; N,N'-dimethylol methacrylamide; N-methylol C 1-5 alkylene cyclic lactams; and lower alkyl ethers of said compounds.
Claim 27
Dependent Claim 45 words
A product according to claim 25 which is obtained by reacting (A) and (B) in aqueous solution in the presence of (C) a catalyst suitable for crosslinking N-methylol compounds (B) and selected from the nitrates, sulphates, chlorides and dihydrogen orthophosphates of aluminum, magnesium and zinc.

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CH574536B5 Cited
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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-10-17 1987-04-18 1987-10-18 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-10-17 1991-04-18 1991-10-18 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-10-17 1995-04-18 1995-10-18 $7700.00 Window Closed / Lapsed

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