Polysiloxanes with radiation- and moisture-cross-linkable groups

Patent metadata

Field	Value
Publication number	US-12448487-B2
Application number	US-202017916053-A
Country	US
Kind code	B2
Filing date	Apr 14, 2020
Priority date	Apr 14, 2020
Publication date	Oct 21, 2025
Grant date	Oct 21, 2025

Abstract

An organo(poly)siloxane (A) consists of units of general formula (I) R n SiO (4-n/2) , where R is selected from the radicals R 1 , —OR 2 , R u , R S and Q, wherein R 1 denotes a monovalent substituted or unsubstituted hydrocarbon radical having 1 to 18 carbon atoms, R 2 denotes a hydrogen atom or a monovalent substituted or unsubstituted hydrocarbon radical having 1 to 6 carbon atoms, R u denotes a monovalent aliphatic unsaturated hydrocarbon radical having 2 to 18 carbon atoms, R S denotes a monovalent thiol-functionalized hydrocarbon radical, Q is a nitrogen functional group of formula (II) —CR 5 R 6 —NR 4 R 3 , where R 3 and R 4 each independently denote hydrogen or a substituted or unsubstituted hydrocarbon radical, and R 5 and R 6 each independently denote hydrogen or the methyl radical. The organo(poly)siloxane (A) contains per molecule at least one unit of general formula (III) Q-Si(OR 7 ) 2 O 1/2 , at least 1 aliphatically unsaturated radical R u , and at least 2 thiol-functionalized groups R S .

First claim

The invention claimed is:

1. An organo(poly)siloxane (A) consisting of units of general formula (I)
R n SiO (4-n/2)   (I)

where
n is 0, 1, 2 or 3, wherein the proportion of units in which n=0 is not more than 50 mol % and the proportion of units in which n=1 is not more than 60 mol %, in each case based on all units of general formula (I),
R is selected from the radicals R 1 , —OR 2 , R u , R S and Q, where
R 1 denotes a monovalent substituted or unsubstituted hydrocarbon radical having 1 to 18 carbon atoms,
R 2 denotes a hydrogen atom or a monovalent substituted or unsubstituted hydrocarbon radical having 1 to 6 carbon atoms,
R u denotes a monovalent aliphatic unsaturated hydrocarbon radical having 2 to 18 carbon atoms,
R S denotes a monovalent thiol-functionalized hydrocarbon radical having 1 to 18 carbon atoms,
Q is a nitrogen functional group of formula (II)
—CR 5 R 6 —NR 4 R 3   (II),

where
R 3 and R 4 each independently denote hydrogen or a substituted or unsubstituted hydrocarbon radical having 1 to 18 carbon atoms and
R 5 and R 6 each independently denote hydrogen or the methyl radical, with the proviso that the organo (poly) siloxane (A) contains per molecule at least one unit of general formula (III),
Q—Si(OR 7 ) 2 O 1/2   (III)

in which R 7 is as defined for R 2 ;
at least 1 aliphatically unsaturated radical R u ;
and at least 2 thiol-functionalized groups R S .

2. The organo(poly)siloxane (A) as claimed in claim 1 , in which R u is a vinyl or allyl radical.

3. The organo(poly)siloxane (A) as claimed in claim 1 , in which the radical R S denotes a linear thioalkyl radical having 3 to 6 carbon atoms.

4. The organo(poly)siloxane (A) as claimed in claim 1 , in which the units —NR 4 R 3 are selected from di-n-butylamino, anilino, cyclohexylamino, and N-morpholino units.

5. The organo(poly)siloxane (A) as claimed in claim 1 , which have 10 to 400 units of general formula (I).

6. The organo(poly)siloxane (A) as claimed in claim 1 , in which at least 0.5 mol % of all units of general formula (I) are a unit of general formula (III).

7. The organo (poly) siloxane (A) as claimed in claim 1 , in which the molar ratio of the radicals R S to the radicals R u is within a range between 0.3 and 5.

8. A process for preparing the organo(poly)siloxanes (A) as claimed in claim 1 , in which alkoxysilanes of general formula (IV)
(R 2 O) 3 Si—CR 5 R 6 —NR 4 R 3   (IV)

undergo condensation with silanol groups of a polysiloxane (V) that contains silanol groups and both aliphatically unsaturated radicals R u and thiol-functionalized groups R S .

9. A moisture-and radiation-crosslinkable organo(poly)siloxane mixture (M) comprising an organo(poly)siloxane (A) as claimed in claim 1 .

10. The organo(poly)siloxane mixture (M) as claimed in claim 9 , which comprises a photoinitiator (B).

11. The organo(poly)siloxane mixture (M) as claimed in claim 9 , which comprises a stabilizer (C) to avoid unwanted free-radical reactions.

Assignees

• Wacker Chemie Ag

Inventors

• Stepp Michael
• Jin Hyungdae
• Karabiyik Ufuk
• Makki Rabih

Classifications

• C08K5/07

  Aldehydes; Ketones · CPC title

• C09D183/08

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen · CPC title

• C08G77/388

  containing nitrogen · CPC title

• C08G77/26 Primary

  nitrogen-containing groups · CPC title

• C08G77/20

  containing silicon bound to unsaturated aliphatic groups · CPC title