Method for the production of organosiloxanes modified by a phosphonic acid ester
Phosphone ester modified organosilicon compounds are prepared by reacting phosphonic ester-functionalized alkoxysilane with a silanol-functional organosilicon compound. The product is produced in high yield and purity.
1. A process for the preparation of phosphonic ester-modified organosiloxanes of the formula
(R 2 SiO 2/2 ) p (R 3 SiO 1/2 ) q [O 1/2 H] t [(O f/2 R 1 3-f SiCR 2 2 P(O)(OR) 4 ) 2 ] 2 (I),
in which
R is a hydrogen atom or a monovalent, optionally —CN—, —NCO—, NR 5 2 —, —COOH—, —COOR 5 —, -halogen-, -acryloyl-, -epoxy-, —SH—, —OH— or —CONR 5 2 — substituted Si—C-bonded C 1 -C 20 hydrocarbon radical or C 1 -C 15 hydrocarbonoxy radical in which one or more nonadjacent methylene units may be replaced by groups —O—, —CO—, —COO—, —OCO—, —OCOO—, —S—, or —NR 5 — and in which one or more nonadjacent methine units may be replaced by groups —N═, —N═— or —P═,
R 1 is a hydrogen atom or a monovalent, optionally —CN—, —NCO—, —COOH—, —COOR 5 —, -halogen-, -acryloyl-, —SH—, —OH— or —CONR 5 2 — substituted Si—C-bonded C 1 -C 20 hydrocarbon radical or C 1 -C 15 hydrocarbonoxy radical in which one or more nonadjacent methylene units may be replaced by groups —O—, —CO—, —COO—, —OCO—,—OCOO—, —S—, or —NR 5 — and in which one or more nonadjacent methine units may be replaced by group, —N═, —N═— or —P═,
R 2 is hydrogen or an optionally —CN— or halogen-substituted C 1 -C 20 hydrocarbon radical,
R 4 is hydrogen or an optionally —CN— or halogen-substituted C 1 -C 20 hydrocarbon radical or a substituted or unsubstituted polyalkylene oxide having 1 to 4000 carbon atoms,
R 5 is hydrogen or an optionally —CN— or halogen-substituted C 1 -C 10 hydrocarbon radical,
p is 0 or an integer from 1 to 100,000,
q is 0 or an integer from 1 to 100,000,
f is 1, 2 or 3,
s is an integer which is at least 1 and
t is 0 or an integer which is at least 1,
p+q is an integer which is at least 1,
comprising reacting:
at least one silane of the formula
[(R 3 O) f R 1 3−f SiCR 2 2 P(O)(OR 4 ) 2 ] [III]
with at least one silicon compound of the general formula
(R 2 SiO 2/2 ) p (R 3 SiO 1/2 ) q [O 1/2 H] m [IV]
where
R 3 is hydrogen or an optionally —CN— or halogen-atom-substituted C 1 -C 20 hydrocarbon radical, and
m is an integer 1 or 2,
the reaction taking place neat or in organic solvent.
2. The process of claim 1 , wherein the sum p+q is an integer which is at least 2.
3. The process of claim 2 , carried out in the presence of catalyst.
4. The process of claim 2 , carried out at temperature(s) of 0 to 200° C.
5. The process of claim 2 , carried out in an inert gas atmosphere.
6. The process of claim 1 , carried out in the presence of catalyst.
7. The process of claim 6 , carried out at temperature(s) of 0 to 200° C.
8. The process of claim 6 , carried out in an inert gas atmosphere.
9. The process of claim 1 , carried out at temperature(s) of 0 to 200° C.
10. The process of claim 9 , carried out in an inert gas atmosphere.
11. The process of claim 1 , carried out in an inert gas atmosphere.
12. The process of claim 1 , wherein the reaction takes place in an aprotic organic solvent.
13. The process of claim 1 , wherein the reaction takes place in the absence of a catalyst.
14. The process of claim 1 , wherein the reaction takes place neat.
15. The process of claim 1 , wherein the reaction mixture is homogenous.