Organopolysiloxanes with dye residues

Details Organopolysiloxanes with dye residues Organopolysiloxanes with dye residues

1999-09-20

2001-02-27

Dawson, Robert (Department: 1712)

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

Synthetic resins

From silicon reactant having at least one...

C528S028000, C528S027000, C528S038000, C528S030000, C534S651000

Reexamination Certificate

active

06194534

ABSTRACT:

The invention relates to functionalized silicone compounds with chromophoric molecules additionally attached covalently to them, to processes for their preparation and to the use of these colored silicone compounds.
The simultaneous use of silicone compounds and dyes is hampered by the immiscibility or insolubility of the majority of dyes in silicone compounds. In order to solve this problem, therefore, special blends of dyes with silanes or siloxanes are used, as described for example in U.S. Pat. No. 5,281,240. A further possibility for avoiding this incompatibility is the covalent attachment of dyes to silanes, as is described for example in J. Soc. Dyers and Col. 85, 1969, No. 9, 401-4. U.S. Pat. No. 2,925,313 and U.S. Pat. No. 4,403,099 describe dye-bearing siloxanes. These compounds, however, owing to their preparation processes, such as azo coupling or basic epoxy opening, are restricted to only one class of dye, such as aniline-containing azo compounds or aromatic compounds which carry nitro substituents, and/or to only epoxy-functionalized siloxanes. In addition, these siloxanes do not carry any other functional groups in the polymer chains.
The present invention provides organopolysiloxanes with dye radicals, comprising units of the general formula
R
1
a
(RO)
b
A
c
R
2
d
SiO
(4−a−b−c−d)/2
  (I)
in which
R can be identical or different and is hydrogen atom or monovalent, substituted or unsubstituted hydrocarbon radical,
R
1
can be identical or different and is hydrogen atom or monovalent, SiC-bonded hydrocarbon radical,
R
2
can be identical or different and is substituted, monovalent, SiC-bonded hydrocarbon radical, A can be identical or different and is the radical of a water-soluble organic dye, containing sulfonic acid groups and/or sulfonate groups, and/or of its complex compound with metals,
a is 0, 1, 2 or 3,
b is 0, 1, 2 or 3,
d is 0, 1, 2 or 3, preferably 0 or 1, and
c is 0, 1 or 2, preferably 0 or 1,
with the proviso that the sum of a, b, c and d is less than or equal to 3, the organopolysiloxanes have at least one radical A per molecule, and in the units of the formula (I) where c is other than 0, d is 0.
In the context of the present invention, the term organopolysiloxanes is intended to embrace not only polymeric but also dimeric and oligomeric siloxanes.
The radical R
1
preferably comprises hydrogen atom and hydrocarbon radicals having 1 to 18 carbon atoms, with particular preference hydrocarbon radicals having 1 to 6 carbon atoms, and especially the methyl radical.
Examples of radical R
1
are alkyl radicals, such as the methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl and the tert-pentyl radical, 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 and the 2-ethylhexyl radical, nonyl radicals, such as the n-nonyl radical, decyl radicals, such as the n-decyl radical, dodecyl radicals, such as the n-dodecyl radical, tetradecyl radicals, such as the n-tetradecyl radical, hexadecyl radicals, such as the n-hexadecyl radical and octadecyl radicals, such as the n-octadecyl radical, cycloalkyl radicals, such as cyclopentyl, cyclohexyl and 4-ethylcyclohexyl radical, cycloheptyl radicals, norbornyl radicals and methylcyclohexyl radicals, alkenyl radicals, such as the vinyl, allyl, 3-butenyl, 4-pentenyl and 5-hexenyl radical, aryl radicals, such as the phenyl, biphenylyl, naphthyl and anthryl and phenanthryl radical; alkaryl radicals, such as o-, m-, p-tolyl radicals, xylyl radicals and ethylphenyl radicals; aryl radicals, such as the benzyl radical, and also the &agr;- and the &bgr;-phenylethyl radical.
The radical R preferably comprises hydrogen atom or substituted or unsubstituted alkyl radicals having 1 to 12 carbon atoms, which can be interrupted by oxygen atoms, and with particular preference comprises hydrogen atom, the methyl and the ethyl radical.
Examples of radical R are the examples specified for R
1
.
The radical R
2
preferably comprises substituted hydrocarbon radicals having 1 to 18 carbon atoms, with particular preference hydrocarbon radicals having 1 to 18 carbon atoms, which are substituted by amino groups and/or derivatives thereof, mercapto groups and also carboxyl groups and/or derivatives thereof.
Examples of radical R
2
are hydrocarbon radicals substituted by amino groups and derivatives thereof, such as aminopropyl, aminopropylaminoethyl, cyclohexylaminopropyl or acetylated aminopropyl radicals,
mercapto-substituted hydrocarbon radicals, such as the mercapto-n-propyl radical,
epoxy-substituted hydrocarbon radicals, such as propyl glycidyl ether radical,
hydrocarbon radicals substituted by acrylate and/or methacrylate groups, such as n-propylacrylic ester radical and n-propylmethacrylic ester radical,
hydrocarbon radicals substituted by carboxyl groups or derivatives thereof, such as by alkanoic acid radicals, such as the acetic acid radical, the butyric acid radical, the undecenoic acid radical, by acid anhydrides, such as the succinic anhydride radical, by esters, such as the undecene silyl ester radical,
hydrocarbon radicals substituted by aldehyde groups, such as propionaldehyde radical,
hydroxyl-substituted hydrocarbon radicals, such as primary, secondary and tertiary alcohol radicals, such as the propanol radical, the butanol radical, or aromatic hydroxy-bearing hydrocarbon radicals, such as the phenol radical and the eugenol radical,
hydrocarbon radicals substituted by polyglycol groups, such as alkyl polyglycol radicals, an example being the propyl polyglycol radical,
hydrocarbon radicals substituted by phosphonato groups, such as phosphonatoalkyl radicals,
hydrocarbon radicals substituted by silalactone groups, hydrocarbon radicals substituted by glycoside groups, such as radicals of the formula Z—R
3
— where Z is a glycoside radical composed of from 1 to 10 monosaccharide units and R
3
is alkylene radical or oxyalkylene radical, and also the radicals specified in EP-A-612 759, page 2, line 11 to page 3 up to line 53.
The radical A preferably comprises water-soluble organic dye radicals which contain sulfonic acid groups or sulfonate groups and have azo groups or quinone groups, and/or the complex compound of such radicals with metals.
The radical A can comprise monovalent or polyvalent radicals, so that radical A may also link two or more sil(oxan)yl radicals with one another.
Examples of radical A are
where X is a divalent radical of the formula —YR
4
—
where Y is a radical —O—, —S—, —NH— or —NR
5
—, R
4
is a divalent, substituted or unsubstituted hydrocarbon radical and R
5
is a monovalent, substituted or unsubstituted hydrocarbon radical, with the proviso that, in the compound of the invention, Y is connected to the dye radical and R
4
is connected to the relevant silicon atom.
The radical R
4
preferably comprises divalent, substituted or unsubstituted linear hydrocarbon radicals having 1 to 30 carbon atoms, which can be interrupted by heteroatoms, such as nitrogen, sulfur or oxygen, particular preference being given to substituted or unsubstituted alkylene radicals having 1 to 10 carbon atoms, such as methylene, ethylene, propylene and butylene radical, aminopropylaminoethyl radical, ethylene oxide radical, and alkylene groups substituted by not more than 4 sugar radicals.
The radical R
5
preferably comprises monovalent, substituted or unsubstituted hydrocarbon radicals, particular preference being given to substituted or unsubstituted alkyl radicals having from 1 to 10 carbon atoms.
Examples of R
5
are the methyl, ethyl, propyl, butyl, cyclohexyl, phenyl and benzyl radical.
The organopolysiloxanes of the invention are prepared using preferably azo or quinonoid dyes which possess one or more identical or different reactive groups.
Examples of such reactive groups which may be attached to the dye molecules are radicals of the formula
—SO
2
—(CH
2
)
2
—V,
where V has the meaning of halo, sulfato o

Affiliated with

Also associated with

Rating

Organopolysiloxanes with dye residues does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Organopolysiloxanes with dye residues, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Organopolysiloxanes with dye residues will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2605056