Dyeability or mass coloration of synthetic polyamide

Details Dyeability or mass coloration of synthetic polyamide Dyeability or mass coloration of synthetic polyamide

1999-07-23

2001-04-17

Sanders, Kriellion (Department: 1714)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Processes of preparing a desired or intentional composition...

C524S099000, C524S100000, C524S714000, C524S718000, C524S720000, C525S418000, C525S420000, C525S432000, C528S335000, C528S341000

Reexamination Certificate

active

06218452

ABSTRACT:

It has been found that the dyeability or mass coloration of synthetic polyamides preferably with anionic dyes can be improved by incorporating into untreated polyamide one or more of the following compounds:
a) a compound having at least one sterically hindered amino, imino or amido group (preferably amino); [hereinafter referred to as compounds a)]; or
b) a trimesic acid trialkylamide, or pyromellitic acid tetra-alkylamide, at least one alkyl group of which bears at least one free amino, imino, amido and/or alkylamino group [hereinafter referred to as compounds b)]; or
c) a trialkylamino, imino or amido substituted triazine, at least one alkyl group of which carries a free amino, imino, amido and/or alkylamino group [hereinafter referred to as compounds c)]; or
d) a dyestuff (preferably of the azo-, anthraquinone- or perinone series) that contains at least one group that is reactive to a hydroxy and/or amino group and is preferably free of sulphonic acid groups [hereinafter referred to as compounds d)]; or
e) a synthetic modified polyamide (preferably a polymeric or oligomeric isophthalic acid amide or terephthalic acid amide) containing at least one group that is reactive with a hydroxy and/or amino group [herein- referred to as compounds e)].
Compounds containing a sterically hindered amino group are preferably those containing a group of the formula
in which
R is hydrogen, C
1-8
alkyl, C
1-8
alkoxy, or —COR
5
,
where R
5
is hydrogen, C
1-6
alkyl, phenyl, COO(C
1-4
alkyl) or NR
15
R
16
;
where R
15
is hydrogen, C
1-12
alkyl, C
5-6
cycloalkyl, phenyl or (C
1-12
alkyl)phenyl; and R
16
is C
1-12
alkyl or hydrogen; or
R
15
and R
16
together with the N atom to which they are attached form a five- to seven-membered ring which may contain an additional N or O atom (preferably forming a piperidine or a morpholine ring).
Preferred groups containing sterically hindered amines are of the formula I to VI
in which
R is hydrogen, C
1-8
alkyl, C
1-8
alkoxy, or —COR
5
;
where R
5
is hydrogen, C
1-6
alkyl, phenyl, —COO(C
1-4
alkyl) or NR
15
R
16
;
where R
15
is hydrogen, C
1-12
alkyl, C
5-6
cycloalkyl, phenyl or (C
1-12
alkyl)phenyl; and R
16
is C
1-12
alkyl or hydrogen or
R
15
and R
16
together with the N atom to which they are attached form a five- to seven-membered ring which may contain an additional N or O atom (preferably forming a piperidine or a morpholine ring); and
Y is the group
where CO forms a part of the cyclic structure;
each R
6
independently is selected from hydrogen, C
1-2
alkyl or phenyl, provided only one group R
6
can be phenyl, or both groups R
6
together form the group —(CH
2
)
11
—, —(CH
2
)
n
—, —C(CH
3
)
2
—, —C(CH
3
)
2
—CH
2
CH
2
— or —C(CH
3
)
2
CH
2
CH
2
CH(CH
3
)—,and
n is 1 or 2.
Compounds containing groups of formulae III, IV and V are known, for example, from U.S. Pat. No. 4,292,240 and Japanese Kokai 62-190786, the contents of which are are incorporated herein by reference.
More preferred compounds of a) to c) are those of formulae 1 to 38 below:
in which each R
3
independently is hydrogen or C
1-12
alkyl;
R
4
is a group of formula &agr; or &bgr;
where R′ is hydrogen, C
1-6
alkyl, C
1-4
alkoxy or —CO—C
1-4
alkyl.
A is C
2-3
alkylene;
R
4′
is of formula &agr;′ or &agr;″
R
2
is C
1-3
alkyl.
where
Preferred groups that are reactive to —OH or —NH
2
(of compounds of d) and/or e) are e.g. those known as reactive groups in the chemistry of reactive dyes. More preferably such are cyclic groups having at least 2 nitrogen atoms (separated preferably by one or two carbon atoms), e.g. triazinyl-, pyrimidyl-, quinoxalyl-, quinazolyl groups phthalazinyl, benzoxazolyl and benzthiazolyl groups, bearing 1 to 3 chlorine atoms on the carbon atoms adjacent to the nitrogen atoms.
Additional more preferred reactive groups are of formula i) to xi)
in which Z is a halogen (preferably chlorine) or a group of the formula
where A
−
is an anion.
Preferably Alkyl is C
1-4
alkyl.
Such groups are described in The Chemistry of Synthetic Dyes, Vol. VI, Chapter I - by E. Siegel, [editor K. Venkataraman,] Academic Press. (1972);
Chimica, Supplement März 1968, Farben Symposium Interlaken, p. 102 et seq - E. Siegel “Chemie der Reactivfarbstoffe” and
Angew. Chem. 76, (1964), No. 10, p. 423 et seq - K.G. Kleb “Ueber neue Reactivfarbstoffe”.
Of particular interest are those compounds a) to c) for incorporation into synthetic polyamides having one or two sterically hindered amino groups and one or two groups reactive to —OH and/or —NH
2
.
Such compounds having one or two sterically hindered amino groups and one or two groups reactive to OH and/or —NH
2
are of formulae 39 to 46 below:
41. R
4
—CO—CH═CH
2
42. R
4
—CO—CH
2
CH
2
SO
2
C
6
H
5
43. R
4
—SO
2
—CH═CH
2
Compounds of formulae 39-46 can be prepared conventionally, e.g. by condensing the appropriate acid chloride or the cyanuric-acid chloride with a free amino or imino group of a sterically hindered amine containing compound in appropriate amounts.
The preferred azo, anthraquinone or perinone dyestuffs of compounds d having groups that are reactive to hydroxy and/or amio groups are preferably those described in Examples 50 to 69 inclusive, hereinafter described.
Examples 50-58 are in 2:1 chromium complex form.
EXAMPLE 50
EXAMPLE 51
EXAMPLE 52
EXAMPLE 53
EXAMPLE 54
EXAMPLE 55
EXAMPLE 56
EXAMPLE 57
EXAMPLE 58
EXAMPLE 59
EXAMPLE 60
EXAMPLE 61
EXAMPLE 62
EXAMPLE 63
EXAMPLE 64
EXAMPLE 65
EXAMPLE 66
EXAMPLE 67
EXAMPLE 68
EXAMPLE 69
The preferred polymeric isophthalic or terephthalic acid amides of compounds e) and a) respectively are those of formula VII and VIII
Pa - (R
11
)
m
  VII
Pa - (CO—R
12
)
m
  VIII
in which Pa is a nitrogen containing radical of a synthetic polyamide,
R
11
is a group attached to the nitrogen atom of the polyamide molecule containing one or more groups reactive to hydroxy and/or amino,
R
12
is a group containing a sterically hindered amino group and
m is 1 or 2.
The compounds of formulae VII and VIII can be added to a synthetic polyamide before, during or after the polycondensation synthesis or worked into the molten mass.
The compounds of formula VIII can be produced when a synthetic polyamide having a terminal carboxy group or functional derivative thereof (e.g. the acid chloride or an ester) is reacted during the polycondensation process with one or more amino groups or one or more sterically hindered amino group containing compounds, preferably of aromatic nature. The reactive groups are preferably those described above as groups of formula i-xii.
The compounds of the formula R
12
H which are used for producing the compounds of formula VIII have a reactive nitrogen atom that is either an amino group or part of a cycle group, for example a piperazine group. These compounds may also contain one or two sterically hindered nitrogen atoms in a cyclic structure, for example N—C
1-4
alkyl or N-acyl substituted 2,2,6,6-tetraalkylpiperidyl-4-groups.
The synthetic polyamides according to the invention can be dyed in the mass with any type of dyestuff, provided that it is stable at high temperatures (of the melt). Preferred dyestuff groups are the monoazo-metal complexes, in particular the chrome complexes that are sufficiently stable at high temperatures to be used. Preferred reactive dyestuffs that can be used are the halogen-containing triazinyl or vinyl group containing metallized azo dyestuffs (i.e., those metallized with chromium, nickel or copper). Such reactive dyestuffs have been commercially available for a number of years.
The preparation of modified synthetic polyamides according to the invention can be effected in a conventional manner, preferably by mixing the reactive compounds with molten synthetic polyamide, e.g. in an extruder prior to spinning, or before or during the polycondensation process of the synthetic amide itself.
Generally one uses 0.5 to 5 percent by weight of the compounds a) to e) based on the weight of synthetic polyamides. More preferabl

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