Hydroxy or amino terminated hydrophilic polymers

Details Hydroxy or amino terminated hydrophilic polymers Hydroxy or amino terminated hydrophilic polymers

1999-12-22

2001-07-31

Truong, Duc (Department: 1711)

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

Synthetic resins

From sulfur-containing reactant

C528S367000, C528S369000, C525S088000, C525S157000, C525S205000, C525S266000, C525S213000

Reexamination Certificate

active

06268467

ABSTRACT:

BACKGROUND OF THE INVENTION
The present invention generally relates to certain hydrophilic polymers. These polymers undergo negligible shrinkage when polymerized and are highly hydrophilic, rendering them useful in a variety of applications.
SUMMARY OF THE INVENTION
This invention relates to hydrophilic polymers of the formula (I):
X—(M)
n
—(Y)
p
  (I)
wherein:
X is derived from a chain transfer agent and includes a terminal hydroxyl or amino radical;
Y is derived from an ethylenically unsaturated monomer that includes a terminal hydroxyl or amino radical;
M is derived from a hydrophilic ethylenically unsaturated monomer;
n is about 5 to 50; and
p is 0 to 5, preferably 1.
One preferred class of the formula (I) hydrophilic polymers are polymers of the formula (Ia):
X—((M′)
x
(M″)
y
(M′″)
z
)—(Y)
p
  (Ia)
wherein:
X, Y and p are as defined for formula (I);
Y is derived from an ethylenically unsaturated monomer that includes a terminal hydroxyl or amino radical;
M′ is derived from a first hydrophilic ethylenically unsaturated monomer;
M″ is derived from a second hydrophilic ethylenically unsaturated monomer;
M′″ is derived from a hydrophobic ethylenically unsaturated monomer;
each of x and y is at least one, and x+y is about 5 to 50; and
z is 0 to 20.
The invention further provides ethylenically endcapped derivatives of these compounds, and thermoplastic polymers prepared therefrom.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
The hydroxy- or amino-terminated hydrophilic polymers of formulae (I) and (Ia) are derived from an ethylenically unsaturated hydrophilic monomer. Preferred hydrophilic monomeric precursors, represented by M′ and M″ in formula (Ia), arc N-vinyl lactams, such as N-vinyl pyrrolidone (NVP), and (meth)acrylamides, such as N,N-dimethyl acrylamide (DMA) and N-octyl acrylamide (NOA). Optionally, the hydrophilic polymers may be derived from an additional ethylenically unsaturated hydrophobic monomeric precursor, represented by M′″ in formula (Ia), provided that this hydrophobic monomeric is present in a sufficiently lower molar ratio than the hydrophilic monomeric precursor so that the resultant polymer remains predominantly hydrophilic. Representative hydrophobic monomeric precursors are (C
1
-C
20
) alkyl(meth)acrylate, (C
1
-C
20
) fluoroalkyl(meth)kicrylate, (C
1
-C
20
) alkyl(meth)acrylamide, or (C
1
-C
20
) fluoroalkyl(meth)acrylamide.
The ethylenically unsaturated hydrophilic monomers, and the ethylenically unsaturated hydrophobic monomers if present, are polymerized in the presence of a chain transfer agent which serves to control the molecular weight of the resultant polymer and provides hydroxy- or amino- functionality to the resultant polymer. Suitable chain transfer agents include mercapto alcohols (also referred to as hydroxymercaptans) and aminomercaptans. Preferred chain transfer agents include 2-mercaptoethanol and 2-aminoethanethiol, Accordingly, the chain transfer agent forms a terminal end of the hydrophilic polymer, with the hydroxy radical (in the case of a mercapto alcohol) providing the resultant polymer with terminal hydroxyl functionality, and the amino radical (in the case of a aminomercaptan) providing the resultant polymer with terminal amino functionality. Generally, the molar ratio of chain transfer agent to the total hydrophilic and hydrophobic monomer precursors will be about 1:5 to about 1:100.
The ethylenically unsaturated hydrophilic monomers, the ethylenically unsaturated hydrophobic monomer if present, and the chain transfer agent are copolymerized with another monomer having ethylenic unsaturation and a hydroxy- or amino- radical. Accordingly, this additional monomer is also reactive with the hydrophilic monomers and also provides terminal hydroxy- or amino- functionality to the resultant polymer. Suitable monomers include alcohol esters of (meth)acrylic acid such as 2-hydroxyethylmethacrylate (Hema), allyl alcohol, amino esters of (meth)acrylic acid such as 2-t-butyl-aminoethyl methacrylate, and allylamine. Generally, this hydroxy- or amino-containing ethylenically unsaturated monomer will be at a 1:1 molar ratio to the chain transfer agent.
Representative reaction schemes are illustrated as follows in the case where p is one, and the polymers are based on a single hydrophilic monomeric precursor:
Representative reaction schemes are illustrated as follows in the case where p is one, and the polymers are based on two different hydrophilic monomeric precursors:
In the above representative schemes,
Such synthesis methods are generally known in the art, and representative detailed syntheses are described in the Examples.
The subject polymers are highly hydrophilic and are useful in a variety of applications. As a first example, the subject polymers can be used as precursors to form prepolymers useful as a contact lens material, Such materials are described more fully in U.S. Pat. No. 5,969,076, the disclosure of which is incorporated herein by reference. An example of such material is provided in Examples 8 and 9 below. As a second example, the subject polymers can be reacted with monomers containing epoxy, isocyanate, carboxylic acid, carboxylic acid chloride or anhydride functionality to form hydrophilic macromonomers useful in forming hydrogels. As yet another example, the polymers can be used to form a hydrophilic coating on an object such as a contact lens, an intraocular lens, a catheter or other biomedical devices, when such objects include functionality reactive with the hydroxy- or amilo- functionality of the subject polymers, such as the functional groups mentioned above.
As an illustration of the present invention, several examples are provided below. These examples serve only to further illustrate aspects of the invention and should not be construed as limiting the invention.


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