Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From reactant having at least one -n=c=x group as well as...
Reexamination Certificate
1999-03-27
2002-04-09
Gorr, Rachel (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From reactant having at least one -n=c=x group as well as...
C528S073000, C528S075000, C528S393000, C549S553000, C560S065000, C560S066000, C560S115000, C560S158000, C252S182180, C252S182200, C252S182230
Reexamination Certificate
active
06369188
ABSTRACT:
BACKGROUND OF THE INVENTION
This invention relates to polyfunctional urethane- or urea-containing oligomers, their methods of synthesis, and polymers and compositions prepared therefrom.
One of the groups of polymers with the most attractive combination of properties that is currently used in the plastics, paint, adhesives, etc. industries are polyurethanes. The unique complex of polyurethane properties is created by the ability of the urethane groups to participate in strong intermolecular interactions.
The superior properties of polyurethanes are caused by the unique characteristics of the urethane group. Most of the other classes of polymers do not have similar complex of positive features as polyurethanes. However, the properties of the other currently manufactured polymers (from elastomers to plastics) could be significantly improved by introduction of the urethane group into the molecules of polymer.
The intention to combine the polyurethanes advantages with the inherent properties of other resins has led to the synthesis of urethane-epoxies, for example as described in Russian Patent No. 287,589 and U.S. Pat. Nos. 2,830,038, 3,984,376, 4,520,185, and 5,484,853; urethane-acrylics and urethane-methacrylics, for example as described in U.S. Pat. Nos. 3,850,770, 4,131,600, 4,133,723, 4,153,778, 4,246,391, 4,330,657, 4,339,566, 4,507,458, 4,587,201, 4,605,723, 5,006,436, and 5,616,630; urethane-alkoxysilanes, for example as described in U.S. Pat. Nos. 4,374,237, 4,555,561, and 4,857,623; and urethane-vinyls and allyls, for example as described in U.S. Pat. Nos. 3,719,638, 4,119,510, and 5,580,947.
However, the disclosed in the available literature amount of types of functional groups combined with urethanes in single oligomeric molecules is limited to the above-mentioned compounds. The range of the described products is very narrow.
Despite the obvious advantages of the described products, they are not widely used in the industrial applications. The limited amount of the utilized functional groups, difficulty in the adjustment of physical and chemical properties of products and complex and limited methods of production of described in available literature compounds lead to limitations on the range of properties of both produced oligomers and the final products obtained after their curing.
BRIEF SUMMARY OF THE INVENTION
In a first aspect, this invention provides oligomers of formula (1)
B(—R
1
—C(O)—NH—R
2
—R
3
)
n
(1),
where:
B is a backbone selected from the group consisting of polyesters, polyethers, polyolefins, polybutadienes, polysiloxanes, carbohydrates, polyacrylates, and mixtures and copolymers thereof;
each R
1
, which may be the same or different, is selected from —O—,—S—, and —N(R
5
)—, where R
5
is selected from hydrogen or a monovalent organic radical; each R
2
, which may be the same or different, is a bivalent organic radical; each R
3
is a group selected from an isocyanate group or a group of formula (2):
—NH—C(O)—R
1
—R
4
—ƒ (2),
where:
each R
1
is as defined above,
each R
4
is a bivalent radical selected from the group consisting of bivalent aliphatic, cycloaliphatic, aromatic, substituted aliphatic, substituted cycloaliphatic, and substituted aromatic radicals, and bifunctional polyesters, polyethers, polyolefins, polybutadienes, polysiloxanes, and polyacrylates;
ƒ is a functional group, and
n is an integer from 2 to 10;
in which at least two different R
3
groups are present in the oligomer, and if one R
3
group is isocyanate, then at least three different R
3
groups are present in the oligomer.
In a second aspect, this invention provides mixtures of oligomers in which at least one oligomer is one of the above oligomers.
In a third aspect, this invention provides methods to produce the above oligomers.
In a fourth aspect, this invention provides polymers prepared from the above oligomers, alone or in combination with other urethane oligomers.
In a fifth aspect, this invention provides compositions such as adhesives, sealants, coatings, and composites containing these oligomers and polymers prepared therefrom.
The herein-described and claimed products and methods of their synthesis substantially widen the range of urethane- and urea-functional oligomers, expand their properties, provide mechanisms for the adjustment of these properties, and ease the production of oligomers.
DETAILED DESCRIPTION OF THE INVENTION
Definitions
A “backbone carrier” is an oligomer of formula (3):
B—(R
1
H)
n
(3),
where:
B, R
1
, and n are as defined previously.
“Functional groups” (FGs), ƒ, are groups of two types:
(1) groups capable of reaction by polymerization or polycondensation; and
(2) groups that provide desired changes in the physical and/or chemical properties of the final product.
Suitable functional groups ƒ as described in this invention are selected from reactive functional groups, including but not limited to epoxy (oxirane), acrylate, methacrylate, mercaptan, vinyloxy, allyl, carboxyl, ketone, nitrile, organic nitrate, primary, secondary and tertiary amine, organic peroxide, alkoxysilane, carbonate, aromatic, saturated and unsaturated organic radicals, halogenated organic radicals, heterocyclic radicals, and the like; catalytic, photoinitiator or stabilizer functional groups including but not limited to tertiary amines, imidazoles, organic peroxides, metalloorganic and heterocyclic radicals, hydroxyketones, hydroquinones, and the like; and physical property-modifying functional groups including but not limited to aliphatic, cycloaliphatic and aromatic, saturated and unsaturated organic radicals, halogenated organic radicals, and the like.
Functional groups ƒ are attached to the backbone of the oligomers by the use of compounds called “functional group (FG) carriers”.
An “FG carrier” is a compound of formula (4):
ƒ—R
4
—R
1
H (4),
where
ƒ, R
1
, and R
4
are as defined previously.
A “polyfunctional reactive urethane- or urea-containing oligomer” (PRUO) is a compound of the formula:
B(—R
1
—C(O)—NH—R
2
—R
3
)
n
(1),
where:
B is a backbone selected from the group consisting of polyesters, polyethers, polyolefins, polybutadienes, polysiloxanes, carbohydrates, polyacrylates, and mixtures and copolymers thereof;
each R
1
, which may be the same or different, is selected from —O—, —S—, and —N(R
5
)—, where R
5
is selected from hydrogen or a monovalent organic radical;
each R
2
, which may be the same or different, is a bivalent organic radical;
each R
3
is a group selected from an isocyanate group or a group of formula (2):
—NH—C(O)—R
1
—R
4
—ƒ (2),
where:
each R
1
is as defined above,
each R
4
is a bivalent radical selected from the group consisting of bivalent aliphatic, cycloaliphatic, aromatic, substituted aliphatic, substituted cycloaliphatic, and substituted aromatic radicals, and bifunctional polyesters, polyethers, polyolefins, polybutadienes, polysiloxanes, and polyacrylates;
ƒ is a functional group, and
n is an integer from 2 to 10;
in which at least two different R
3
groups are present in the oligomer, and if one R
3
group is isocyanate, then at least three different R
3
groups are present in the oligomer.
The PRUOs are the oligomers of this invention. They are compounds that have multiple and diverse useful properties. These properties are determined by the type, functionality and length of the backbone, the type of linkages (urethane or substituted urea), and the types, combinations and relative amounts of functional groups on the PRUO.
In the preferred compounds of this invention:
B is a backbone selected from polyesters (for example, poly(neopentyl glycol adipate), alkyd resins, polyethylene glycol maleate, and the like), polyethers (for example, polyethylene glycol (polyoxyethylene), polyoxypropylene, polytetramethylene glycol, and the like), polyolefins (for example, castor oil, low molecular weight polyethylenes, hydrogenated polybutadiene, and the like), polybutadienes (for example, cis- and trans-polybutadienes, a
Rappoport Leonid
Vainer Alex
Yam Aleksandr
Gorr Rachel
Heller Ehrman White & McAuliffe LLP
Polymeright, Inc.
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