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US4243390A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for dyeing or printing fibrous material using quaternary polymerized ammonium salts as assistants

Assignee: BASF Corp
•
Filing: 1979-12-26
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Granted: 1981-01-06
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Expires: 1999-12-26
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Abstract

Abstract A process for dyeing or printing organic fibrous material made e.g. of polyamide, polyester or polyacrylonitrile, and also of cellulose, said process comprising the use of a dyeing or printing assistant which contains a quaternary ammonium salt. The salt is a reaction product of a copolymer of maleic anhydride and ethylene, propylene or styrene, with a N,N-disubstituted n-alkylenediamine, a homopolymer of a vinylpyridine, or a quaternized copolymer of a vinylpyridine and styrene. The reaction product, the homopolymer, and the copolymer are quaternized with e.g. benzyl chloride. The ammonium salt can also be a homopolymer of a vinylbenzyl chloride which is quaternized with a tertiary monoamine. The fibrous material dyed or printed with e.g. direct or disperse dyes or with cationic dyes has excellent levelness, good penetration of the dye, and good wetfastness properties. It is also possible to obtain multi-shade effects by printing the material patchwise with a reserve paste and then dyeing it.

Inventors

  • 👤 Paul Schafer
  • 👤 Hans-Ulrich Berendt
  • 👤 Jaroslav Haase

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 05:31
CPC Classifications
D; D06; D06P; D06P1/00; D06P1/44; D06P1/52; D06P1/5207; D06P1/525; D06P1/5214; D06P1/5242

Claims Analysis

Total Claims: 19
Claim 1
Independent Claim 284 words
A process for dyeing or printing organic fibrous material using a dyeing or printing assistant which contains, as quaternary ammonium salt, (a) a reaction product of a copolymer of maleic anhydride and ethylene, propylene or styrene, with a N,N-disubstituted 1,2-ethylenediamine or 1,3-propylenediamine, in which the substituents are alkyl of 1 to 4 carbon atoms or together with the nitrogen atom form a 5- or 6-membered ring which optionally contains an oxygen atom as second heteroatom, (b) a homopolymer of a 4-vinylpyridine which is unsubstituted or substituted at a ring carbon atom by methyl or ethyl, (c) a copolymer of the above vinylpyridine and styrene, and the reaction product (a), the homopolymer (b) and the copolymer (c) are quaternised with an alkyl or alkenyl halide containing up to 6 carbon atoms alone, or with a halomethylnaphthalene, halomethyldiphenyl, chloroacetamide, chloroacetonitrile, or with a haloacetic acid or an alkali metal salt or alkyl ester of haloacetic acid containing 1 to 12 carbon atoms in the alkyl moiety, or with a benzyl halide which is unsubstituted or substituted by halogen, methyl or ethyl, alone or in admixture with each other or with an alkyl or alkenyl halide containing up to 4 carbon atoms, or (d) a homopolymer of a 2- or 4-vinylbenzyl chloride which is quaternised with a tertiary monoamine containing up to 20 carbon atoms, whilst two substituents of the monoamine are alkyl of 1 to 4 carbon atoms or together with the nitrogen atom form a 5- or 6-membered ring which optionally contains an oxygen atom as second heteroatom, and the third substituent of the monoamine is alkyl, alkenyl or aryl containing up to 18 carbon atoms which is unsubstituted or substituted by alkyl or alkylene.
Claim 2
Dependent Claim 284 words
A process for dyeing or printing organic fibrous material using a dyeing or printing assistant which contains, as quaternary ammonium salt, (a) a reaction product of a copolymer of maleic anhydride and ethylene, propylene or styrene, with a N,N-disubstituted 1,2-ethylenediamine or 1,3-propylenediamine, in which the substituents are alkyl of 1 to 4 carbon atoms or together with the nitrogen atom form a 5- or 6-membered ring which optionally contains an oxygen atom as second heteroatom, (b) a homopolymer of a 4-vinylpyridine which is unsubstituted or substituted at a ring carbon atom by methyl or ethyl, (c) a copolymer of the above vinylpyridine and styrene, and the reaction product (a), the homopolymer (b) and the copolymer (c) are quaternised with an alkyl or alkenyl halide containing up to 6 carbon atoms alone, or with a halomethylnaphthalene, halomethyldiphenyl, chloroacetamide, chloroacetonitrile, or with a haloacetic acid or an alkali metal salt or alkyl ester of haloacetic acid containing 1 to 12 carbon atoms in the alkyl moiety, or with a benzyl halide which is unsubstituted or substituted by halogen, methyl or ethyl, alone or in admixture with each other or with an alkyl or alkenyl halide containing up to 4 carbon atoms, or (d) a homopolymer of a 2- or 4-vinylbenzyl chloride which is quaternised with a tertiary monoamine containing up to 20 carbon atoms, whilst two substituents of the monoamine are alkyl of 1 to 4 carbon atoms or together with the nitrogen atom form a 5- or 6-membered ring which optionally contains an oxygen atom as second heteroatom, and the third substituent of the monoamine is alkyl, alkenyl or aryl containing up to 18 carbon atoms which is unsubstituted or substituted by alkyl or alkylene.
Claim 3
Dependent Claim 138 words
A process according to claim 1, in which the assistant contains (a) a reaction product of a copolymer of maleic anhydride and ethylene, propylene or sytrene, with a N,N-disubstituted 1,2-ethylenediamine or 1,3-propylenediamine, in which the substituents are alkyl of 1 to 4 carbon atoms or together with the nitrogen atom form a 5- or 6-membered ring which optionally contains an oxygen atom as second heteroatom, or (b) a homopolymer of a 4-vinylpyridine which is unsubstituted or substituted at a ring carbon atom by methyl or ethyl, and the reaction product (a) and the homopolymer (b) are quaternised with a halomethylnaphthalene, halomethyldiphenyl, chloroacetamide, chloroacetonitrile or with a benzyl halide which is unsubstituted or substituted by halogen, methyl or ethyl, alone or in admixture with each other or with an alkyl or alkenyl halide containing up to 4 carbon atoms.
Claim 4
Dependent Claim 199 words
A process according to claim 1, in which the assistant contains a quaternary ammonium salt the recurring units of which correspond to the formulae ##STR24## in which Q 1 is alkyl or alkenyl containing 6 to 12 carbon atoms, or is a substituent of the formulae ##STR25## or a mixture of a substituent of the formulae indicated for Q 1 and alkyl or alkenyl containing up to 4 carbon atoms, A is ethylene or n-propylene, E 1 is hydrogen, methyl or phenyl, M 1 is hydrogen or an alkali metal, or alkyl of 1 to 12 carbon atoms, R 1 and R 2 are alkyl of 1 to 4 carbon atoms or together with the nitrogen atom to which they are attached form a 5- or 6-membered ring which optionally contains an oxygen atom as second heteroatom, T 1 is alkyl, alkenyl, or aryl which contains up to 18 carbon atoms and is unsubstituted or substituted by alkyl or alkylene, X 1 .sup.⊖ is halogen, Y 1 and Y 2 are methyl or ethyl, Z 1 , Z 2 and Z 3 are halogen, ethyl or methyl, and n, p, q, r, s and t are 1 or 2.
Claim 5
Dependent Claim 134 words
A process according to claim 1 in which the assistant contains a quaternary ammonium salt containing recurring units of the formula ##STR26## in which Q 2 is a substituent of the formulae ##STR27## or a mixture of a substituent of the formulae indicated for Q 2 with alkyl or alkenyl containing up to 4 carbon atoms, and A is ethylene or n-propylene, E 1 is hydrogen, methyl or phenyl, R 3 and R 4 are methyl, ethyl, n-propyl or n-butyl or together with the nitrogen atom to which they are attached form a pyrrolidine, piperidine or morpholine radical, X 1 .sup.⊖ is halogen, Y 1 and Y 2 are methyl or ethyl, Z 1 , Z 2 and Z 3 are halogen, methyl or ethyl, and r, s and t are 1 or 2.
Claim 6
Dependent Claim 75 words
A process according to claim 1, in which the assistant contains a quaternary ammonium salt containing recurring units of the formula ##STR28## in which Q 3 is --CN, --CO--NH 2 or phenyl, A is ethylene or n-propylene, X 2 .sup.⊖ is chlorine or bromine and R 5 and R 6 are methyl, ethyl or n-propyl, or R 5 and R 6 together with the nitrogen atom to which they are attached form a morpholine radical.
Claim 7
Dependent Claim 39 words
A process according to claim 1 in which the assistant contains a quaternary ammonium salt containing recurring units of the formula ##STR29## in which A is ethylene or n-propylene and R 5 and R 6 are methyl or ethyl.
Claim 8
Dependent Claim 51 words
A process according to claim 1, in which the assistant contains a quaternary ammonium salt containing recurring units of the formula ##STR30## in which X 1 .sup.⊖, Y 1 , Y 2 , p and q are as defined in claim 3 and Q 2 is as defined in claim 4.
Claim 9
Dependent Claim 40 words
A process according to claim 1, in which the assistant contains a quaternary ammonium salt containing recurring units of the formula ##STR31## in which X 2 .sup.⊖ is chlorine or bromine and Q 3 is --CON, --CO--NH 2 or phenyl.
Claim 10
Dependent Claim 71 words
A process according to claim 1, in which the assistant contains a quaternary ammonium salt containing recurring units of the formula ##STR32## in which D is ethylene or methylene, T 2 is alkyl or aryl containing up to 18 carbon atoms which is unsubstituted or substituted by methyl or ethyl, v is 1 or 2, and R 3 , R 4 and X 1 .sup.⊖ are as defined in claim 4.
Claim 11
Dependent Claim 48 words
A process according to claim 1, in which the assistant contains a quaternary ammonium salt containing recurring units of the formulae ##STR33## in which T 4 is naphthyl, benzyl or phenyl, R 5 and R 6 are ethyl or methyl, and X 2 .sup.⊖ is bromine or chlorine.
Claim 12
Dependent Claim 24 words
A process according to claim 1, in which the quaternary ammonium salt contained in the assistant has a molecular weight of 1500 to 1,000,000.
Claim 13
Dependent Claim 20 words
A process according to claim 1, in which the assistant is in the form of an aqueous or organic solution.
Claim 14
Dependent Claim 30 words
A process according to claim 1, which comprises the use of 0.01 to 5% of the assistant, calculated as pure ammonium salt, based on the weight of the fibrous material.
Claim 15
Dependent Claim 36 words
A process according to claim 1, which comprises the use of synthetic fibers of polyacrylonitrile, acrylonitrile copolymers, or of modified polyester or polyamide which can be dyed with cationic dyes, or of natural fibers of cellulose.
Claim 16
Dependent Claim 40 words
A process according to claim 1, in which the fibrous material is dyed or printed with a preparation which is in the form of an aqueous or aqueous-organic solution, dispersion, printing paste or printing ink, and which contains a dye.
Claim 17
Dependent Claim 29 words
A process according to claim 1, in which the fibrous material is dyed by the exhaust method in the presence of the dyeing assistant as defined in claim 1.
Claim 18
Dependent Claim 31 words
A process according to claim 1, in which the fibrous material is printed patchwise, before dyeing, with an aqueous printing paste which contains the printing assistant as defined in claim 1.
Claim 19
Dependent Claim 25 words
An aqueous preparation for carrying out the process according to claim 1, which conains a cationic dye and the assistant as defined in claim 1.

References Cited (Backward Citations)

US2740687A Cited
US2861863A Cited
GB855028A Cited
GB1092965A Cited
US3940247A Cited
US4036587A Cited
DE2604910A1 Cited
US4095942A Cited
US4131422A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-01-06 1984-07-07 1985-01-06 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-01-06 1988-07-07 1989-01-06 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-01-06 1992-07-07 1993-01-06 $7700.00 Window Closed / Lapsed

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