Process for the treatment of cellulose fibres

Details Process for the treatment of cellulose fibres Process for the treatment of cellulose fibres

1999-04-09

2001-03-20

Tentoni, Leo B. (Department: 1732)

Plastic and nonmetallic article shaping or treating: processes

Treating shaped or solid article

Reexamination Certificate

active

06203746

ABSTRACT:

The present invention relates to a process for reducing the fibrillation tendency in lyocell cellulose fibres.
“Lyocell” designates fibres that have been obtained by a process in which the cellulose is dissolved in an organic solvent, in a combination of an organic solvent and an inorganic salt, or in an aqueous salt solution, and is then spun from the resulting solution.
The usefulness of flat goods, for example textile materials, produced from such fibres as severely limited, however, as a result of the pronounced tendency of those fibres to fibrillate in the wet state. “Fibrillation” is to be understood as meaning the breaking up of the wet fibres in the longitudinal direction when subjected, for example, to mechanical stress, to the extent that fibrils become detached along the surface of the fibres, giving the fibres a hairy or furry appearance. In addition, a fabric produced from such fibres suffers a pronounced loss in colour intensity after a few washes.
A need therefore exists for a process that reduces or completely prevents fibrillation in lyocell fibres.
Surprisingly, it has been found that by means of the process according to the invention the fibrillation tendency of the treated lyocell fibres is substantially reduced.
The present invention accordingly relates to a process for the treatment of lyocell cellulose fibres which comprises treating the lyocell cellulose fibres with at least one compound of the formula
wherein
R
1
and R
2
are each independently of the other halogen or a sulfo-substituted phenylamino radical, at least one of the two substituents R
1
and R
2
being halogen,
R
3
and R
4
are each independently of the other unsubstituted phenyl or phenyl substituted by C
1
-C
4
alkyl, C
1
-C
4
alkoxy, acylamino, sulfo, —SO
2
—CH═CH
2
, —SO
2
—CH
2
CH
2
—OSO
3
H, —NH—CO—CBr═CH
2
or by —NH—CO—CHBr—CH
2
Br,
A
1
and A
2
are each independently of the other —O—, —S— or —NR
5
—, wherein R
3
is hydrogen or C
1
-C
4
alkyl,
A
3
and A
4
are each independently of the other —O—, —S— or —NR
5
—, or —A
3
—R
3
is halogen and/or —A
4
—R
4
is halogen, wherein R
5
is hydrogen or C
1
-C
4
alkyl and
B is an aromatic bridge member, or
—A
1
—B—A
2
— is a bridge member of the formula —NH—CH
2
—CH(CH
3
)—NH—,
with the proviso that the compound of formula (1) must contain at least one dihalotriazine radical, at least two monohalotriazine radicals or at least one substituent, but preferably at least two identical or different substituents, from the group consisting of —SO
2
—CH═CH
3
, —SO
2
—CH
2
CH
2
—OSO
3
H, —NH—CO—CBr═CH
2
and —NH—CO—CHBr—CH
2
Br.
C
1
-C
4
Alkyl as a phenyl substituent in R
3
and R
4
is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl.
As C
1
-C
3
alkyl R
5
is methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl.
C
1
-C
4
Alkoxy as a phenyl substituent in R
3
and R
4
is, for example, methoxy, ethoxy, propoxy or butoxy.
Acylamino as a phenyl substituent in R
3
and R
4
is, for example, acetylamino.
A
3
—R
3
and A
4
—R
4
as halogen are preferably fluorine and especially chlorine.
B as an aromatic bridge member is, for example, a radical of the formula
in which formulae (2a) to (2f) the phenyl radicals may be mono- or poly-substituted by sulfo.
R
1
and R
2
as halogen are each independently of the other fluorine or chlorine.
R
1
is preferably halogen, especially chlorine.
R
2
is preferably halogen, especially chlorine.
R
3
is preferably a phenyl radical substituted by C
1
-C
4
alkyl, C
1
-C
4
alkoxy, acylamino, sulfo, —SO
2
—CH═CH
2
, —SO
2
—CH
2
CH
2
—OSO
3
H, —NH—CO—CBr═CH
2
or by —NH—CO—CHBr—CH
2
Br, the phenyl radical being mono- or poly-substituted by the substituents mentioned.
There is preferred as R
4
a phenyl radical substituted by C
1
-C
4
alkyl, C
1
-C
4
alkoxy, acylamino, sulfo, —SO
2
—CH═CH
2
, —SO
2
—CH
2
CH
2
—OSO
3
H, —NH—CO—CBr═CH
2
or by —NH—CO—CHBr—CH
2
Br, the phenyl radical being mono- or poly-substituted by the substituents mentioned.
A
1
is preferably —NR
5
—.
A
2
is preferably —NR
5
—.
A
3
is preferably —NR
5
—.
A
4
is preferably —NR
5
—.
R
5
is preferably hydrogen.
Compounds of formula (1) that are of importance for the process according to the invention are those wherein A
1
, A
2
, A
3
and A
4
are —NH—, B is a radical of the formula
R
1
is chlorine, fluorine or
R
2
is chlorine or fluorine, R
3
is a radical of the formula
and R
4
is a radical of formula (4a), (4b), (4d), (4e), (4f),
or A
3
-R
3
and/or A
4
-R
4
are/is chlorine.
Compounds that are of particular importance for the process according to the invention are the compounds of formulae
Compounds that are more especially important for the process according to the invention are the compounds of formulae (100), (101), (102), (103), (105), (108), (114), (117), (118) and (119).
The compounds of formulae (100), (101), (103), (105) to (116) and (119) are novel and the present invention relates also thereto.
The preparation of the compounds of formula (1) used in the process according to the invention is carried out according to methods known per se, for example by reacting a trichlorotriazine of the formula
or a trifluorotriazine of the formula
with an equimolar amount of a compound of the formula
R
3
—A
3
H  (6),
wherein R
3
and A
3
are as defined for formula (1), and then with a compound of the formula
HA
1
—B—A
2
—H  (7),
wherein A
1
, A
2
and B are as defined for formula (1),
to form an intermediate of the formula
Subsequently, a second trichlorotriazine of formula (5) or a second trifluorotriazine of formula (5a) is, where appropriate, reacted with an equimolar amount of a compound of the formula
R
4
—A
4
H  (9),
wherein A
4
and R
4
are as defined for formula (1),
and then with the intermediate of formula (8), and the resulting compound of the formula
is isolated.
Alternatively, for example, a trichlorotriazine of formula (5) or a trifluorotriazine of formula (5a) is reacted with a compound of formula (7) in a molar ratio of 2:1.
The novel compounds of formulae (100), (101), (103), (105) to (116) and (119) are prepared in an analogous manner by reacting a trichlorotriazine of formula (5) with a compound of the formula
and then with a compound of the formula
and condensing the resulting intermediate with a second trichlorotriazine of formula (5), which has, where appropriate, been reacted beforehand with a compound of the formula
or, when A
3
—R
3
═A
4
—R
4
, reacting a trichlorotriazine of formula (5) with a compound of formula (13),
and condensing the resulting intermediate with a compound of the formula
in a molar ratio of 2:1, or, when A
3
—R
3
═A
4
—R
4
=halogen, condensing a trichlorotriazine of formula (5) with a compound of formula (15) or
in a molar ratio of 2:1, or reacting a trifluorotriazine of formula (5a) with a compound of the formula
and then with a compound of formula (16), and condensing the resulting intermediate with a second trifluorotriazine of formula (5a), which has been reacted beforehand with a compound of the formula
or, when A
3
—R
3
═A
4
—R
4
, reacting a trifluorotriazine of formula (5a) with a compound of formula (27) or (11), and condensing the resulting intermediate with a compound of the formula
or (21) in a molar ratio of 2:1.
Compounds of formulae (11) to (28) are known and can be prepared according to methods known per se.
An advantageous embodiment of the process according to the invention comprises treating the lyocell cellulose fibres with the compounds used in accordance with the invention in an alkaline medium.
The alkaline medium is preferably formed by an alkali metal carbonate and/or an alkali metal hydroxide, such as, for example, sodium carbonate, sodium hydroxide or potassium hydroxide.
The treatment can be performed either on undyed fibres, or on fibres that are to be dyed, before, during or immediately after a dyeing process. Where the compounds used in accordance with the invention are applied to undyed fibres, they may be a

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