Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From silicon reactant having at least one...
Reexamination Certificate
2001-10-19
2004-06-29
Peng, Kuo-Liang (Department: 1712)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From silicon reactant having at least one...
C528S038000, C528S028000, C106S287110, C556S414000, C525S440030, C525S453000, C525S419000, C568S679000
Reexamination Certificate
active
06756465
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to moisture curable compounds, which can be used in moisture curable adhesive compositions. More particularly, the present invention relates to moisture curable compounds, which can cure through alkoxysilane groups to form high strength bonded articles.
2. Brief Description of Related Technology
U.S. Pat. No. 6,057,001 describes a coating composition having a polyacetoacetate and a crosslinker. The coating composition may also have an organosilane. Although the composition has improved substrate-adhesion and is particularly useful as a primer for an aluminum substrate, it is not a moisture curable composition.
U.S. Pat. No. 5,744,528 describes a water-curable resin composition composed of a water-reactive alkoxysilane terminated resin having at least one hydrolyzable group per molecule. The composition is used to prepare an orthopedic cast. While the alkoxysilane terminated resin is moisture curable, the composition employs materials such as the primer and biuret adducts of tetramethylxylene diisocyanate (TMXDI).
U.S. Pat. No. 5,587,502 describes hydroxy functional alkoxysilane and alkoxysilane functional polyurethane made therefrom. The alkoxysilane functional polyurethanes prepared from a hydroxy functional alkoxysilanes, such as, hydroxycarbamoylsilane, can be derived from TMXDI and are moisture curable. The alkoxysilane functional polyurethanes may be used moisture-curable adhesives and sealants.
U.S. Pat. No. 5,432,246 describes a silane functional oligomer suitable for use in the formulation of clear coating compositions. The oligomer has at least one hydrolyzable silane group and is the reaction product of: (i) a silane coupling agent having a hydrolyzable silane group and a secondary amine group, (ii) a polyisocyanate having more than one tertiary isocyanate group and other optional components. The polyisocyanate can be a TMXDI/TMP adduct, which is the reaction product of tetramethylxylene diisocyanate and trimethylolpropane.
European Patent Application No. EP-A-0 267 698 discloses a coating composition suitable for automobile refinish which includes an oligomer having hydrolyzable silane groups and a polymer having hydrolyzable silane groups. The oligomer is made by first reacting a hydroxyalkyl acrylate with a polyisocyanate to produce an intermediate having terminal unsaturated groups followed by reaction of this intermediate with an aminosilane. These compositions suffer from the problem that the water resistance of coatings produced from them is not entirely satisfactory, possibly due to the presence of amine groups in the oligomer.
Japanese Patent application No. JP 60-44549 discloses coating compositions including a silane functional urethane polymer and a silane functional vinyl resin. The silane functional urethane polymer is made by reacting an isocyanate functional urethane prepolymer with a silane coupling agent such as an aminosilane. A problem with this composition is that when the level of urea groups in the oligomer is high, the films formed from them become very hard and brittle and exhibit poor flexibility, which is a significant disadvantage, particularly in adhesive applications.
Not withstanding the state of the technology, it would be desirable to provide a moisture curable adhesive composition having an alkoxysilane terminated urethane based on polyethers or ester groups containing A-B-A block copolymers. Accordingly, the present invention provides such moisture curable adhesive compositions having long shelf life and excellent adhesion on substrates.
These and other aspects of the present invention will become apparent from the following description.
SUMMARY OF THE INVENTION
The present invention provides a moisture curable compound represented by the formula:
wherein W is a difunctional group selected from the group consisting of: a hydrocarbylene of 2 to 22 carbon atoms, an ether containing group, a thioether containing group, an ester containing group, a thioester containing group, an amide containing group, a thioamide containing group, a urea containing group, a urethane containing group, and a combination thereof;
wherein R
1
is a group represented by the formula:
R
2
is a group represented by the formula:
R
3
is selected from the group consisting of: hydrogen and hydrocarbyl group of 1 to 6 carbon atoms;
R
4
is a hydrocarbylene group of 1 to 4 carbon atoms;
each R
5
is independently a hydrocarbyl group of 1 to 6 carbon atoms; and
n is zero or 1; with the proviso that when n is zero, R
3
is hydrogen.
In one aspect, the present invention provides a moisture curable compound represented by the formula:
wherein each R
9
is independently selected from the group consisting of: hydrogen and methyl; and W is a difunctional group selected from the group consisting of: a hydrocarbylene of 2 to 22 carbon atoms, an ether containing group, a thioether containing group, an ester containing group, a thioester containing group, an amide containing group, a thioamide containing group, a urea containing group, a urethane containing group, and a mixture thereof.
In another aspect, the present invention provides a moisture curable compound represented by the formula:
wherein W is a difunctional group selected from the group consisting of: a hydrocarbylene of 2 to 22 carbon atoms, an ether containing group, a thioether containing group, an ester containing group, a thioester containing group, an amide containing group, a thioamide containing group, a urea containing group, a urethane containing group, and a mixture thereof.
The present invention further provides processes for preparing the moisture curable compounds of the invention.
In the first of these processes, there is provided a process for preparing a moisture curable compound represented by the formula:
The process includes:
contacting at least two equivalents of &agr;,&agr;,&agr;′,&agr;′-tetramethylxylylene diisocyanate represented by the formula:
and a difunctional hydroxy compound represented by the formula:
HO—W—OH
at a temperature and length of time sufficient to produce a 2:1 &agr;,&agr;,&agr;′,&agr;′-tetramethyl xylylene diisocyanate: difunctional hydroxy compound adduct; and
contacting the 2:1 &agr;,&agr;,&agr;′,&agr;′-tetramethyl xylylene diisocyanate: difunctional hydroxy compound adduct and an aminosilane represented by the formula:
(R
5
O)
3
Si—R
4
—NHR
3
at a temperature and length of time sufficient to produce the moisture curable compound;
wherein W is a difunctional group selected from the group consisting of: a hydrocarbylene of 2 to 22 carbon atoms, an ether containing group, a thioether containing group, an ester containing group, a thioester containing group, an amide containing group, a thioamide containing group, a urea containing group, a urethane containing group, and a combination thereof;
R
3
is selected from the group consisting of: hydrogen and hydrocarbyl group of 1 to 6 carbon atoms;
R
4
is a hydrocarbylene group of 1 to 4 carbon atoms; and
each R
5
is independently a hydrocarbyl group of 1 to 6 carbon atoms.
In the second of these processes, there is provided a process for preparing a moisture curable compound represented by the formula:
The process includes the steps of:
contacting at least two equivalents of an isocyanatosilane represented by the formula:
(R
5
O)
3
Si—R
4
—NCO
and a difunctional hydroxy compound represented by the formula:
HO—W—OH
at a temperature and length of time sufficient to produce the moisture curable compound;
wherein W is a difunctional group selected from the group consisting of: a hydrocarbylene of 2 to 22 carbon atoms, an ether containing group, a thioether containing group, an ester containing group, a thioester containing group, an amide containing group, a thioamide containing group, a urea containing group, a urethane containing group, and a mixture thereof;
R
4
is a hydrocarbylene group of 1 to 4 carbon atoms; and
each R
5
is independently a hydrocarbyl g
Jacobine Anthony Francis
Nakos Steven Thomas
Bauman Steven C.
Henkel Loctite Corporation
Peng Kuo-Liang
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