Process for treating organic fibers

Details Process for treating organic fibers Process for treating organic fibers

2002-03-26

2003-04-15

Green, Anthony (Department: 1755)

Compositions

Durable finishes for textile materials, or processes of...

C252S008630, C252S008810, C252S008840, C252S008850, C106S287110, C427S387000, C427S389900

Reexamination Certificate

active

06547981

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to a process for treating organic fibers with amino-functional organosilicon compounds.
2. Background Art
Siloxanes bearing ammonium groups are well known from the literature, and may be prepared in various ways. One synthetic route, as described in GB-A 2 201 433 for example, starts with epoxy-functional silicones, which are obtained by a hydrosilylation of Si-H-bearing siloxanes with a vinyl-bearing epoxide, i.e. (allyl glycidyl ether) and reacts these epoxy-functional silicones with ammonium salts of tertiary amines to form silicones bearing ammonium groups. A further possibility comprises first preparing an aminoalkyl-bearing siloxane and then quaternizing it with alkylating agents, as described in EP-A 436 359.
Aminosiloxanes used as softeners in textile finishing overwhelmingly bear aminoethylaminopropyl or aminopropyl pendant groups. These pendant groups, which are cationic in neutralized form, become aligned on the fiber surface and hence cause the siloxane to become oriented on the fiber surface. This leads to an extremely soft and pleasant hand for textile substrates treated therewith. Aminosiloxanes are customarily applied in the form of emulsions. This constitutes the last operation in the production of textile fabrics and can be accomplished by so-called forced application, for example in a pad-mangle, or else in principle by exhaustion, owing to the cationic character of the aminosiloxanes.
A significant disadvantage of aminosiloxanes used today in textile finishing is the drastically impaired rewettability of textile substrate finished therewith. Rewettability is especially troublesome in the textile finishing field insofar as textile material, once finished, can no longer be crossdyed. This is important in particular because silicones, owing to their low refractive index, have a strongly color-deepening effect which can lead to hue shifts. Similarly, in the case of off-shade dyeings, poor rewettability of fabric treated with silicone softeners is detrimental because correcting the shade is virtually impossible. In addition, there are articles among consumer textiles which, although a “fuzzy” soft hand is desired, must be rewettable, for example terry toweling, underwear, etc. Similar requirements apply to treated nonwovens used, for example, in skin care. These articles must likewise have a soft hand without impairing absorbency.
SUMMARY OF THE INVENTION
It is an object of the present invention to provide a process for treating organic fibers with amino-functional organosilicon compounds which confer a soft hand and good rewettability without adverse effect on the thermal yellowing of the treated organic fibers and textile materials containing them.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT(S)
This object is achieved by the process for treating organic fibers with aqueous preparations comprising amino-functional organosilicon compounds of the general formula
H
2
N—R
1
—SiR
2
O(SiR
2
O)
i
SiR
2
—R
1
—NH
2
where
i is an integer from 1 to 1,000, preferably 20 to 650,
R is an identical or different monovalent hydrocarbon radical having 1 to 18 carbon atoms per radical, and
R
1
is a divalent hydrocarbon radical having 2 to 10 carbon atoms.
The organosilicon compounds of the invention are preferably linear diorganopolysiloxanes having terminal SiC-attached amino groups. The viscosity of the organosilicon compounds is preferably in the range from 30 to 10,000 mPa·s at 25° C., more preferably in the range from 30 to 5,000 mPa·s at 25° C., and the amine number is preferably in the range from 1.35 to 0.035 mmol/g and more preferably in the range from 1.35 to 0.042 mmol/g.
Examples of R radicals are alkyl radicals, such as the methyl, ethyl, n-propyl, isopropyl, 1-n-butyl, 2-n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and tert-pentyl radicals, hexyl radicals such as the n-hexyl radical, heptyl radicals such as the n-heptyl radical, octyl radicals such as the n-octyl radical and isooctyl radicals such as the 2,2,4-trimethylpentyl radicals, nonyl radicals such as the n-nonyl radical, decyl radicals such as n-decyl radical, dodecyl radicals such as n-dodecyl radical, and octadecyl radicals such as the n-octadecyl radical; cycloalkyl radicals such as the cyclopentyl, cyclohexyl, cycloheptyl and methylcyclohexyl radicals; aryl radicals such as the phenyl, naphthyl, anthryl and phenanthryl radicals; alkaryl radicals such as o-, m-, p-tolyl, xylyl and ethylphenyl radicals; and aralkyl radicals such as the benzyl, &agr;-phenylethyl and &bgr;-phenylethyl radicals. R is preferably an alkyl radical having 1 to 6 carbon atoms per radical, preferably methyl.
Examples of R
1
are ethylene, n-propylene, isopropylene, n-butylene, cyclohexylene, phenylene and butenylene. R
1
is preferably an alkylene radical, preferably an alkylene radical of 3 or 4 carbon atoms, most preferably n-propylene.
The amino-functional organosilicon compounds of the invention may be prepared, for example, by a two stage process. The first stage of the process comprises reacting a short-chain dialkylpolysiloxane which bears a reactive Si—H group on both end groups with N,N-bis(trimethylsilyl)allylamine in the presence of a hydrosilylation catalyst. In the second stage, the &agr;,&ohgr;-aminoalkylene-diorganopolysiloxane thus obtained is coequilibrated with cyclic methylsiloxanes under basic catalysis.
The aqueous preparations of the invention are preferably in the form of an aqueous emulsion or an aqueous solution. The aqueous emulsions preferably comprise the amino-functional organosilicon compound of the invention, optionally an emulsifier, acid, and water.
The aqueous emulsions can be prepared by generally known processes. The preparation of the emulsions can be effected in customary mixing apparatus suitable for preparing emulsions, such as high-speed stator-rotor stirrers after Professor P. Willems of the kind known under the registered trademark “Ultra-Turrax”. The organosilicon compounds of the invention can be emulsified using prior art processes such as shearing or phase inversion emulsification or by heating.
The aqueous emulsions preferably contain emulsifiers known per se.
Examples of anionic emulsifiers are:
1. Alkyl sulfates, particularly those having a chain length of 8 to 18 carbon atoms, alkyl and alkaryl ether sulfates having 8 to 18 carbon atoms in the hydrophobic radical and 1 to 40 ethylene oxide (EO) or propylene oxide (PO) units.
2. Sulfonates, particularly alkylsulfonates of 8 to 18 carbon atoms, alkylarylsulfonates of 8 to 18 carbon atoms, taurides, esters and monoesters of sulfosuccinic acid wit h monohydric alcohols or alkylphenols of 4 to 15 carbon atoms; optionally these alcohols or alkylphenols can also be ethoxylated with 1 to 40 EO units.
3. Alkali metal and ammonium salts of carboxylic acids having 8 to 20 carbon atoms in the alkyl, aryl, alkaryl or aralkyl radical.
4. Phosphoric acid partial esters and their alkali metal and ammonium salts, particularly alkyl and alkaryl phosphates having 8 to 20 carbon atoms in the organic radical, alkyl ether and alkaryl ether phosphates having 8 to 20 carbon atoms in the alkyl or alkaryl radical respectively and 1 to 40 EO units.
Examples of nonionic emulsifiers are:
5. Polyvinyl alcohol still having 5% to 50% and preferably 8% to 20% of vinyl acetate units and a degree of polymerization of 500 to 3,000.
6. Alkyl polyglycol ethers, preferably those having 6 to 40 EO units and alkyl radicals of 8 to 20 carbon atoms.
7. Alkylaryl polyglycol ethers, preferably those having 8 to 40 EO units and 8 to 20 carbon atoms in the alkyl and aryl radicals.
8. Ethylene oxide/propylene oxide (EO/PO) block copolymers, preferably those having 8 to 40 EO or PO units.
9. Addition products of alkylamines having alkyl radicals of 8 to 22 carbon atoms with ethylene oxide or propylene oxide.
10. Fatty acids of 6 to 24 carbon atoms.
11. Alkylpolyglycosides of the general formula R*—O—Z
o
, where R* is a linear or branched, saturated or unsaturated alkyl radical ha

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