CA1087203A - Organosilane compounds - Google Patents

Abstract

ORGANOSILANE COMPOUNDS
Abstract of the Disclosure Novel compounds of the formula or siloxane oligomers thereof, wherein R1 is an alkyl group containing 1 to 4 carbon atoms, (CH3)3Si or Z(OCxH2x)m where x is 2 to 4, m is 1 to 20, Z is hydrogen, an alkyl group containing 1 to 18 carbons or an acyl group containing 1 to 4 carbon atoms; a is 0 to 2; R2 is an alkyl group con-taining 1 to 18 carbon atoms; R3 is an alkyl group containing 1 to 18 carbon atoms; R4 is an alkyl, aryl or arylalkyl group containing 1 to 12 carbon atoms, a carboxy-substituted alkyl group containing 1 to 4 carbon atoms, (CxH2xO)mZ

where x, m, and Z are as defined above, or oxygen provided only one R4 is oxygen and that when R4 is oxygen, there is no X-; R5 is an alkyl, aryl or arylalkyl group containing 1 to 22 carbon atoms; X-is halide; and Y is nitrogen, phosphorus or sulfur. The novel compounds are useful for inclusion in a detergent composition for imparting soil release benefits to metallic and vitreous surfaces contacted therewith.

Description

BACKGROUND OF THE INVENTION
. . . _ _ This invention relates to novel organosilane compounds.
Various quaternized substituted organosilane compounds are known. For example, British Patent 686,068 discloses compounds having the general formula [ (R3SiCH2) aNR bH4-a-b]
where R is an alkyl, monocyclic aryl hydrocarbon or alkoxy radical, Rl is an alkyl, alicyclic hydrocarbon or mono-cyclic aryl hydrocarbon radical or hydroxy alkyl radical, a is 1 to 2, b is 0 to 3 with a+b being not greater than 4 and Y is an acid anion. Boyer, British Patent 1,164,581, dated September 17, 1969, discloses compounds of the general formula ~-[( )asi(cH3)3-acH2N(cH3)3] Br wherein R is an alkyl radical containing 1 to 6 carbon atoms or a phenyl radical and a is 1 or 2. Isquith et al U.S. Patent 3,730,701 issued May 1, 1973 discloses compounds of the formula (cH30)3si(cH2)3N (CH3)2R R
where R is an alkyl radical having 11 to 22 carbon atoms and Rl is halide. These compounds are said to be useful as intermediates in the formation of organosilicon resins, catalysts and emulsifying agents (Dow Corning B. P.
686,068 published January 14, 1953), as modifiers for organopolysiloxane resins and oils (Boyer B. P. 1,164,581 published September 17, 1969) and for the control of algae (Isquith et al U~ S. Patent 3,730,701 issued May 1, 1973).
Cox, U. S. Patent 3,560,442 issued February 2, 1971 discloses cross-linking agents of formula ~- 30 (RO)3SiCH(R )N(R )R

where R is an alkyl radical having 1 to 4 carbon atoms, ~, ,................................. .

~0~7203 R is hydrogen, an alkyl radical having 1 to 6 carbon atoms or a phenyl radical, R is hydrogen or a methyl . . .
radical and R is hydrogen, alkyl, cycloalkyl, aminoalkyl, (methylamino)-alkyl or (dimethylamino~-alkyl radical with 1 to 6 carbon atoms or a radical of formula . .
(RO)3SiCH(R )- or (RO)3SiCH(R )N(R )CH2CH2-.

British Patent 882,057 diseloses eompounds of formula R Ib N - R X4-c-b LR
wherein R is a substituted or unsubstituted alkyl group, l l R and R are hydrogen, or organie radicals, preferably alkyl, aminoalkyl, eyanoalkyl, hydroxyalkyl, earbo-alkoxyalkyl, earboxyalkyl or aryl radicals, or the monovalent grouping - R - Si - X

~ 2 where x is an alkoxy radieal or the oxygen atom of a siloxylidyne radical ^ Si - 0 -, or R and R
together with the nitrogen atom may form a heteroeyelie ring, Y is a hydroxy, alkoxy, alkyl or aryl radieal, ~ is an alkoxy, alkyl, or aryl radieal, e is 1 or 2, b is 0 to

2~ 2, and e+b is not more than 3.
It has now been found that the novel eompounds as hereindeseribed are useful as an additive to a detergent eomposition. Heekert et al U.S. Patents 4,005,028 and 4,005,030 issued January 25, 1977, diselose detergent eompositions eontaining a elass of organosilanes. When metallie or ~, ''.

~i / .,, . , ~
.

7Z~3 vitreous surfaces are washed with a detcrgent com?osition containing the organosilane, a thin polymeric coating of the organosilane is deposited upon the washed or rinsed surfaces. The polymerized coating imparts a soil release benefit to the surface, therebv making the surace easier to clean in subsequent washings.
It is an object of this invention to produce novel organosilane compounds.

~t is another object of this invention to produce organosilane compounds having utilitv in a detergent composition.
These and other objects will become apparent from the description to follow.
As used herein all percentages and ratios are by weight unless otherwise indicated.

i~ SUMMARY OF THE INVENTION
An organosilane having the formula 2Ja 1' l4 1 )3-a Si ~ t ~ Y - R5 X

~, . , .
's ~
l - :
j, '- ~ ' ''' ' . ~

~87Z03 or siloxane oligomers thereof having a degree of poly-merization of 2 to 100, wherein Rl is an alkyl group containing 1 to 4 carbon atoms, (CH3)3Si or Z(cxH2x)m where x is 2 to 4, m is 1 to 20, Z is hydrogen, an alkyl group containing 1 to 18 carbons or an acyl group containing 1 to 4 carbon atoms; a is 0 to 2; R2 is an alkyl group containing 1 to 18 carbon atoms; R3 is an alkyl group containing 1 to 18 carbon atoms; R4 is an alkyl, aryl or arylalkyl group containing 1 to 12 carbon atoms, a carboxy-substituted alkyl group containing 1 to 4 carbon atoms, (CxH2x)mz where x, m, and Z are as defined above, or oxygen provided only one R4 is oxygen and that when R4 is oxygen, _ there is no X ; R5 is an alk~l, aryl or arylalkyl group containing 1 to 22 carbon atoms; X is halide; and Y is nitrogen, phosphorus or sulfur, provided that when Y
is sulfur there is only one R4.
DESCRIPTION OF THE PRBFERRED EMBODIMENTS
This invention relates to organosilane compounds having the formula (R2)a IH IR4 (R1O)3-a ~ Si - IC - IY - R5 X

.

.~~ 5 ` D
., ~,~,.
,.

72t)3 or siloxane oligomers thereof wherein Rl, x, m, ~, R2, a, R3, b, R4, R5, Y and X are as defined immediately above.
Preferably X is chloride or bromide, a is O or 1, R3 is a methyl group, R4 is an alkyl group containing 1 to 4 carhon atoms and R5 is an alkyl, aryl or arylalkyl group containing 6 to 12 carbon atoms.
It should be understood that the R4 in the above formula and the formulae to follow may be the same or differ-ent. It should further be understood that when Y is sulfur, there will be only one R4 substituent. Also, when one R4 is oxygen or, under basic conditions, the anion of a carboxylic acid substituted alkyl, the counter ion X is not extant. The 1 to 4 carbon atoms in the carboxy-sub-stituted alkyl group is inclusive of the carboxyl group.
The preparation of the above compounds is described in the succeeding paragraphs.
The compounds when a is O and R is an alkyl group and R4 is an alkyl, aryl or arylalkyl group are prepared by the following route:

~ ' 20~

r1 h O
.,1 ~~i `
U~ o O .!C`~ ^ ~ X
~1 ~1 0 ~ ~1 o ~ o '-/ ~ X :>~ 0 ~1 U) C O ,-~
U~ X ~ ~
+ ~ lJ ~'~1 X ~ + O r~
.Y
(1~ 1 ,Y ~ X X
~ ~ U--X ~ ~ X X
X ,C ~1 1~ U~ o ,~ o U~ h u~ ~1 0 ~ ) I X
X -- X-- ~ ~ ~ ~
`-- ~I h ~1 ~ ~ h ~,1 ~

,C ~ h h h CJ O h O

+ + + +
: , ~: :
.. .

O ~ X ~ -

3 ~ x ~
X h X
,~; `-~ B~ ~ -. r~.

;
.

1~72~3 The trihalosilane is reacted with an olefin at 100C. for 4 to 10 hours under a pressure of 50 to 300 psi. in the presence of a chloroplatinic acid or platinum catalyst to produce the trihaloalkylsilane. This reaction is reported by F. P. Mackay, O. W. Steward and P. G. Campbell in "Journal of the American Chemical Society, 79, 2764 (1957) and J. L. Speier, J. A. Webster and S. W. Barnes in Journal of the American Chemical Society, 79, 974 (1957).
The trihaloalkylsilane is then halogenated in a known manner by treating it with halogen in the presence of light (such as that provided by ordinary tungsten or fluorescent lamps). Preferably, halogenation is carried out to only partial completion and a distillation is performed to recycle unreacted alkylsilane.
The resultant alpha-haloalkyltrihalosilane is reacted with a lower alcohol to produce the alpha-haloalkyltrialkoxy-silane. At least three equivalents of alcohol per equivalent of haloalkyltrihalosilane are added slowly to the cilane~
The alpha-haloalkyltrihalosilane may be dissolved in an inert solvent, preferably hexane or pentane. (See W. Noll, "Chemistry and Technology of Silanes", Academic Press, New York, 1968, page 81 for the alcoholysis of halosilanes.) One equivalent of the alpha-haloalkyltrialkoxysilane is reacted with one equivalent of the tertiary amine, tertiary phosphine, or dialkylsulfide to produce the organosilane.
; An inert solvent, preferably of high dielectric constant, may be used. The reaction is carried out at temperatures of from 40C. to 100C. and a time of 2 to 10 hours for the reaction of the bromopropyltrialkoxysilane and 120C. to 140C. for ,~ .
,~_ i 11;~8~3 2 to 20 hours for the reaction of the chloropropyltrialkoxy-silane.
When a is 1 or 2, the preparation of the compounds is essentially the same except for the use of an alkyl substituted silane as the starting reactant.
The organosilanes when at lease one R4 is a carboxy-substituted alkyl group are prepared in the same manner except for the last reaction step. Here, a tertiary amine, tertiary phosphine or dialkylsulfide having a carboxy-containing alkyl group(s) is reacted with the alpha-haloalkyltrialkoxysilane at 50C. to 200C. for 2 hours to 20 hours. Such carboxy-substituted tertiary amines, tertiary phosphines, and dialkylsulfides are produced by reacting R4YHR5 or HYR5 (where Y is sulfur) ~ . ' ' 15 with X (CH2) 1-3CH
, in the presence of base at elevated temperatures, e.g. 50C.
to 150C.
' - When at least one R4 is ~- . .

( XH2X)m~

., , .
tB ~

~0~72~)3 with x, m and ~ as defined above, the o~ounds are produced in the m~r given above except for the last reaction step. Thus, alpha-haloalkyltrialkoxysilane is reacted with a tertiary amine, tertiary phosphine, or dialkylsulfide where at least one substituent is (CxH2x)m~
. , _ ~
.

The reaction takes place at a temperature of 50C.
to 200C. and a time of from 2 to 10 hours.
Organosilanes where one R4 is oxygen are prepared by following the reactions outlined above up to the last reaction step. At this point, a dialkyl amine, dialkyl phosphine or alkylthiol is reacted with the halosilane at 50C. to 200C. for from 4 to 10 hours and then with base to ' produce an intermediate tertiary amine, phosphine, or dialkyl lS sulfide. These intermediates are then reacted with H2O2 at 20C. to 100C. or preferably 03 in an inert solvent at -80C. to 20C. to yield the organosilane.
.
' :'........................................ ' . :, .
,~," ' ,' ~

.!, ' ., . ' ' .

37Z~3 The compounds that ~ollow are illustrative of these compounds.

(C2H50)3sicH(c8Hl7)N (cH3)2cl2H25 (CH30)3SiCH(cl8H37)N (C2H4cooH)2 3 3 7 2 3 ( 12 25)N (C2H4oH)(cH3)2 Cl (C4H90)3SiCH(C3H7)N [(C2H40)1oH]2C6 13 3 3 _ (ClOH21)N [(c2H4o)2c4H9J(cH3)c6H5 Br 3 3 ( 3) [( 2H40)3Coc2Hs3(c2H5)2 Br (C2H50) 2CH3SiCH (C8H17 ) N () (CH3 ) 2 .`., ( H30)3sicH(cgHl7)P (CH3)3 Cl (CH30)2CH3SiCH(CH3)p (C3H6COOH)2C14H28 6 5 2 5 )3SicH~cloH2l)p (C2H4oH)c4H9 Cl-(CH30)3SiCH(C3H7)P (O) (CH3)C12 25 (CH3o)3sicH(c8Hl7)p [(C2H4o)6H]2cH3 (C2H50)3SicH(c6Hl3)P [(C3H6)2C18H37](CH3)2 (CH30)3SiCH(CH3)S (CH3)Cl~H~3 Br ( 2H50)2CH3siCH(C12H25)S (c3H6cooH)cH3 Cl-3 )2C16H33SiCH(C2H5)S (C2H4oH)c2H5 Cl-(cH30)3sicH(cloH2l)s () C5Hll 2 5 )3SiCH(C4Hg)S [(C3H60)loH]c6H5 Cl-(C2H50 ) 3sicH (cH3 ) s ( (C2H40) 2 0C 2Hs ] CH3 ~' "'': ' ', , -- -, ', ~o~

When Rl is x m the organosilane is formed in the same manner as the above compounds when Rl is an alkyl group with the exception that t CXH2X) mOH

is used in place of RlOH

during the alcoholysis of the halosilane~ This reaction takes place at 25 C. to 200C. at 4 hours io 20 hour~.
10A mi.xture of RlOH and . ~(OCxH2x)OH

: can be used in the alcoholysis step to prepare an organo-silane having different substituents on the silicon atom.
. . The following compounds illustrate the organosilane when at least one Rl is l, ~(OCXH2)m-B~ ~

1~7203 , U , ..

o ~
~D hC ) c~ ~1 ~ h ~ ~1 1`
~ o m ~ ~ m ~ c~ ~

C,~ ~ ~ O :~: ~ o : :: o o ~ ~ U o O ~ :C C~ o O ~ ~ U ~ ~r C~ ~ O I O ~ ~ + ~ ~ O O C~ ~ O
-- U O P -- ~ ::C ^ U I ~ 5 +
+ ~ -- t~ + N (~ -- ~ N N U~ + cr ~z m + u + æ u m + o u u ,~
`' U -- N Z -- Z ^ -- U P~ -- -- -- ~ ^ ---- U'`~ C,) ~ ~ ~ U~ + -- ~ + ~ ~ ,~ +
+ ~ + I` ~ + + 1 ~1 ~n Z N + m z :~ N ~ U ~ C _~
N ~ ~ t~ rl U --I ~ ~ U ~
, ~) -- ~ ~,) U~ U -- ~1 u~ -- N 1~ ~ _ U N
. U U ~ C U co ~J U :~ U U
': -- '~I ~ U N U ~ U ~ ~ 1 ~ -- ~1 U --I
U ~ -- N U~ U U ~ U~ ri C,~
: U ~ ~ u~ U v~ , _ U ~ u~
~n u u -- ~-- o ~1 ~ o u u ~n o :c u N ~1 0 .~O ~ U~ ~_U-) ~1 ~1 ~ N t~ ~
N U~^ ^ t`~ O ^ U~ ~ N U~ -~t O O ~) ^ ~~ ) O ~ ~
~ ^ ~ ~ _::C 5 0 ~ C~-- _ N ~ O _-'~ ^ ~ 0 3: 0 N N U~ ~ N O O ^ N ~ O
~r ~ D U U _I ~U N N C~
:~ N ~ U^ O O ^ rO ^ ^ ~
N U C~ O ~ -- -- ~~ r G ~ --u o ~ u U
0~ ~ ~ O ~rl N N NO O N N O ~) N ~) -- u U U U ~ u -- ~ u u -- m v ~) ~ ~C O ~ O N O O ~ :~ O O ~) O O O
m N -- 5 ~~1 ~1 -- 5 N -- -- X
~, u u :c u m u u m ~ u m m o c~ m m ., .

s . U~ o U~

. ,,~,~ .
., ~ .
' . .

m ,~
t~
h ,, :~: c~
v m t~ v~
t~ n ~ ~' ~.1 0 :C
m v _ o t~l ~D ~ o t~ 3: t~, u t~ o t o ~
u ~c` o -- +
~ t~ _ ~ 't~ U ~
+
~n tn + 5~
u~ t~ _ , ~
:t :c t~
t~l t~ t~ u u u ~ o c.) ,~ o u~
c.) c.) :~ t~ ~ o o --u~ ~ ~ t.
_. t~ 3: o o. o :: . t~l u, _ _ c.) o ~ t~, ~ o 3 t~l o, o t~l o O -- tO ~D -- ~
~ :c ~ m a t~ ~r t~ t~, t~ t~ o o ~ o C~ V I 1: V ~:

r~
, .
. . .

.
.. . . .

e~ -- ;: .
. ' ' ' ' ' : '.
, '. ~ . - ' r, When Rl is lv~7~3 (CH3)3Si and a is 0, the compounds are prepared following the descrip-tion given for the preparation of the above compounds with S the exception that a tris(trimethylsiloxy)silane is used as the starting reactant. Commercially available trihalosilanes and trimethylsilanes are used to produce the starting reactant.
When a is 1 or 2, a corresponding organosilane cGmpound where one or two Rl's are alkyl is reacted with a trimethyl-~,~ 10 chlorosilane at about 50C. to 200C. to produce the desired organosilane.
Illustrative compounds follow:

,. ..

! .:

.: . - . :
'~' ' ' ' ~ ` : - ' ' :: . . - . . .

1~872Q3 U I ~ I U
h ~1 U
~1 ~1 a~ ~ c~ u h U~
u U _ m P~ ~) ~ ~: I ~ U
U ~ P~ U ~ V o ~ ~ ~ U
C~ m ~ U ~D
U ~ ~ N --~ U ~I 1` ~ C~ U
U ~ ~ :C ~ 1 1~ ^ U
u :~ o m ~ o :1:
_ O ~ O :~ o ~ u r -J ~ o c~
-- U U CO O m ~ ~ ~ u o ~ o ~~D C~ C~ U ~ ^ ~
er O~ er ~ _ ~ ~ O U ~1 ~: O
~ m o~ m oo ^ :~; ~ u ~ ~ u ~ co U ~U~ ~ O ~ U
)C~ U O ~
~ r O C~ + U
~ + ~_ ~--U U t~ + 5: ~ ~ ~ U u~ ~
:C Z U O + ~ ~ ~P~ ~I + ~ U ~ ~ +
U ^---- Z ~-- ~+ _ U P~ + -- + r~ u~
~ ++ ~ + +
+~: z ~ u~ ~ z _ :r: + , Z~ ~~ ~ -- ^ I` U ~ ~ ~ ~ ~ a>

U ~ U U C~ U U U ~ ~ U U U U O
.~ _ ~_ _ _ _ _ ~q ~ ~ ~ ~ ~ r~ ~
U ~ U C~ U U 5: ~U O C) O ~ U

oooooooooooooooo Ul UJ tn u~

v u u ~ u ~ u u u u u u ~ u c) u~ o In ~7203 m ~ c~
~, ,~
u~ O
~ co -- .
o ~o +
r~
~ o~
o -- ~:
+ +
_ _ ~
u. I_ u r~
r~
.,, .", u~ u, ~3 ._ _ o o o . 1 rl ~1 _ ~ ~ r~
3:
_ - . .

.. . .
.. . .
, ~: .
,~ .
. .

10~7203 Siloxane oligomers of the organosilanes are formed from the monomers by the controlled addition of from 1 to 100 equivalents of water, preferably in an - inert solvent such as alcohol, tetrahydrofuran, etc.
As used herein, "oligomers" is used to mean a degree of polymerization of from 2 to 100, preferably 2 to 20.
A higher degree of polymerization adversely affects the ability of the compound to bond itself to a metallic or vitreous surface as discussed below and is for this reason avoided.
The above organosilanes are useful when used in a detergent composition at a level of organosilane to water-soluble organic detergent of from 2:1 to 1:10,000.
When metallic or vitreous surfaces are washed or rinsed with a detergent composition containing the above-described organosilane, a soil release benefit is imparted to the surface. It is theorized that the positively charged organosilane i9 attracted to the negati~ely charged surface.
j The silicon atom in the organosilane can then form a bond with the surface. The presence of the positive charge on - the organosilane is necessary to allow the bonding to take place from a dilute solution as is encountered in a detergent composition usage context and within a reasonable time period. The terminal alkyl groups attached to the 25 ~ positively charged atom provides the soil release benefits.
It is believed that the organosilane compound polymerizes on the surface to form a thin coating of the polymer.
; The coating is responsible for imparting the soil release benefits to the surface. That is, a hard surface having r I~
~, ~: .

on it the polymeric coating will be soiled; however, the soil is not tenaciously bound to the surface by virtue of the coating and for this reason is easily washed away.
The following examples illustrate this inve~tion.

, ~ .
. ' - .

,~ ~
~ : ' ~0~72~)3 EXAMPLE I

~CH30)3SiCH(CH3)N (CH3)3 Br One mole (163.5g.) of ethyl trichlorosilane is placed in a one liter stirred Pyrex flask and irradiated with a 300 watt flood lamp. To this is added slowly, a cold mixture of 1/4 mole-of chlorine and 1/4 mole of bromine so that a red-brown color is just maintained. When the addition is complete and the red color is gone, the residue is distilled out of the flask, yielding 1/2 mole of starting material, ethyltrichlorosilane and about 1/2 mole of alpha-bromoethyltrichlorosilane.
One-half mole of the alpha-bromoethyltrichlorosilane (121.25g.) is placed in a flask fitted with a stirrer, condensor, dropping funnel and a gas bubbler through which nitrogen is passed. 1.7 moles of absolute methanol (54.4g) are added slowly such that the reaction temperature does not rise above about 60C.. When the methanol addition is complete and HCl evolution has ceased, the residue is distilled under reduced pressure to yield alpha-bromoethyltrimethoxy-silane.
One quarter mole of the alpha-bromoethyltrimethoxy-silane (57.3g) is placed in an autoclave along with 17.7g of trimethylamine. The mixture is heated to 80C. for 6 hours ~under 200 p.s.i. nitrogen. The excess trimethylamine is allowed to evaporate after the product has been removed from l the autoclave, leaving the bromide salt of alpha-trimethyl-ammonioethyltrimethyoxysilane bromide.
,................ . .
,, .
B o~
. . ~

1~872C~3 Corresponding organosilanes where the nitrogen is phosphorus or sulfur are produced by substituting the tri-methylamine with trimethylphosphine and dimethylsulfide, respectively.
EXAMPLE I I

[ (CH3) 3SiO] 3SiCH (CH3) N (CH3) 3 The product of the above reaction, trimethylammonio-ethyltrimethoxysilane bromide, is heated to reflux with an excess of trimethylchlorosilane until 3 equivalents of methylchloride is evolved. The resulting product, alpha-trimethylammonioethyl-tris-trimethylsiloxysilane bromide, is isolated by stripping out the residual volatile reactants.
EXAMPLE I I I

(CH3CH2O)3SiCH(C4Hg)N (CH332CH2C6H5 Br In a manner like that used for the preparation of alpha-bromoethyltriethoxysilane, alpha-bromoamyltriethoxy-silane is prepared in two steps from amyltrichlorosilane (commercially available). One-quarter mole of alpha-bromoamyltriethoxysilane (78.5g) is refluxed for 12 hours with 0.25 moles (33.759) of benzyldimethylamine in 125 ml.
of 2-butanone. The product, alpha- (benzyldimethylammonia) amyltriethoxysilane bromide is isolated by removing the solvent under vacuum.
~ .

t ~ ~D

~ u~;7~03 E~YPLE IV

(CH3OCH2CH2O)3SiCH(CH3)N (CH2CH2OCOCH3)2C12H25 Br One-quarter mole of alpha-bromoethyltrichlorosilane is dissolved in 200 ml. of dry hexane and sparged rapidly with nitrogen. 0.85 moles of the beta-methoxyethanol is added slowly and the resulting mixture is stirred until the HC1 evolution ceases. Distillation of the residue yields alpha-bromoethyltris(beta-methoxyethoxy)silane. `-This product (0.2 moles) is heated with 0.2 moles of the diacetate ester of dodecyldiethanolamine at 135C. for 16 hours to yield the desired quaternary ammonium salt.

.
, ~ : - , ., , :
., - -, .... .. .
,, -:

- : :. , , .~ -, : , -: :~ "~

Claims (12)

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:

1. An organosilane having the formula or siloxane oligomers thereof having a degree of poly-merization of from 2 to 100, wherein R1 is an alkyl group containing 1 to 4 carbon atoms, (CH3)3Si or Z(OCxH2x)m where x is 2 to 4, m is 1 to 20, Z is hydrogen, an alkyl group containing 1 to 18 carbons or an acyl group containing 1 to 4 carbon atoms; a is 0 to 2; R2 is an alkyl group containing 1 to 18 carbon atoms; R3 is an alkyl group con-taining 1 to 18 carbon atoms; R4 is an alkyl, aryl or aryl-alkyl group containing 1 to 12 carbon atoms, a carboxy-substituted alkyl group containing 1 to 4 carbon atoms, (CxH2xO)mZ
where x, m, and Z are as defined above, or oxygen provided only one R4 is oxygen, and that when R4 is oxygen, there is no X-; R5 is an alkyl, aryl or arylalkyl group containing 1 to 22 carbon atoms; X- is halide; and Y is nitrogen, phosphorus or sulfur, provided that when Y is sulfur there is only one R4.

2. The organosilane of claim 1 wherein R1 is an alkyl group.

3. The organosilane of claim 1 wherein R1 is (CH3)3Si.

4. The organosilane of claim 1 wherein R1 is Z(OCxH2x)m.

5. The organosilane of claim 1 wherein a is 0 or 1.

6. The organosiloxane of claim 1 wherein the degree of polymerization is from 2 to 20.

7. The organosilane of claim 1 wherein the organosilane is a monomer.

8. The organosilane of claim 1 wherein X- is chloride or bromide.

9. The organosilane of claim 1 wherein R3 is methyl.

10. The organosilane of claim 1 wherein R4 is an alkyl group containing 1 to 4 carbon atoms.

11. The organosilane of claim 1 wherein R5 contains 6 to 12 carbon atoms.

12. The organosilane of claim 1 having the formula or siloxane oligomers thereof having a degree of poly-merization of 2 to 100, wherein R1 is an alkyl group containing 1 to 4 carbon atoms, (CH3)3 Si or Z (O CxH2x)m where x is 2 to 4, m is 1 to 20, Z is hydrogen, an alkyl group containing 1 to 18 carbon atoms or an acyl group containing 1 to 4 carbon atoms; a is 0 to 2; R2 is an alkyl group containing 1 to 18 carbon atoms; R3 is an alkyl group containing 1 to 18 carbon atoms; R4 is an alkyl, aryl or arylalkyl group containing 1 to 12 carbon atoms, a carboxy-substituted alkyl group containing 1 to 4 carbon atoms, (CxH2xO)mZ
wherein x, m and Z are as defined above, or oxygen provided only one R4 is oxygen and that when R4 is oxygen, there is no X-; R5 is an alkyl, aryl, or arylalkyl group containing 1 to 22 carbon atoms; and X- is halide.