Allyl urethane resin compositions

Details Allyl urethane resin compositions Allyl urethane resin compositions

2000-03-27

2003-05-06

Sergent, Rabon (Department: 1711)

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

Synthetic resins

Polymers from only ethylenic monomers or processes of...

C522S090000, C522S095000, C522S174000, C525S123000, C525S127000, C525S330500, C525S452000, C528S049000, C528S075000, C560S025000, C560S026000, C560S115000, C560S158000

Reexamination Certificate

active

06559260

ABSTRACT:

This invention relates to novel isocyanate based allyl ether derivatives which may be cured using free radical initiators.
Various polyurethane resins are well known for their coating and protective properties. Differing urethanes have different properties depending on the particular organic compounds used to form the urethanes. Similarly, the method of cross linking in the urethane resin to form a cured product will vary with the starting materials for the urethanes.
For instance, U.S. Pat. No. 4,005,041 discloses polyurethane coating compositions with air drying, and or heat curable properties. The urethanes have allyl functionality and are polymers with aliphatic polyols as backbones. The urethanes are high in viscosity and relatively low in allyl functional groups, with air drying properties.
U.S. Pat. No. 4,829,123 relates to an air dryable resin composition. The composition contains one radical-curable resin which may be an unsaturated polyester resin or an acrylic based resin (urethane-acrylic, polyester-acrylic or epoxy-acrylic) along with a urethane-acrylic oligomer, an ethylenically unsaturated monomer, and an initiator.
U.S. Pat. No. 5,763,099 relates to a binder composition for powder coatings. The low temperature-cure binder is a mixture of unsaturated polyester and an oligomer with 2-12 allyl ether groups having ester or urethane groups included. Preferably, the oligomer is an ester of trimethololpropanediallylether and polycarboxylic acid (or anhydride).
U.S. Pat. No. 5,739,251 to Venhan pertains to ethylenically unsaturated polyisocyanates which contain allophanate groups and have specific weight contents of isocyanate, &bgr;, &ggr;-ethylenically unsaturated ether groups, and allophanate groups. The polyisocyanates are intended to be low viscosity materials for use in solvent-free, one-component coating compositions. The polyisocyanate is then used to make an ethylenically unsaturated polyurethane which is substantially free from isocyanate groups. This polyurethane is then combined with an acrylate material such as trimethololpropanetriacrylate to produce a coating.
U.S. Pat. No. 4,005,041 pertains to a method for producing isocyanate adducts. The adducts contain residual isocyanate groups. The adducts are polyurethane coating compositions with air drying and/or heat curable properties. The adducts contain allyl functional groups and have aliphatic polyols as backbones. They are generally high in viscosity and low in allyl functional groups.
U.S. Pat. No. 5,198,528 to Smith, et al. pertains to an alkane resin which is the polymerized product of trimethololpropanediallylether, an aromatic acid, a drying compound, and a polyol. The resin is generally used with a solvent such as mineral spirits. Absent the mineral spirits, the resin has a high viscosity. Therefore it must be thinned with an appropriate solvent prior to use.
U.S. Pat. No. 4,031,271 pertains to a radiation curable, alkali resistant composition of a polyene and polythiol. The alkali resistance allows the cured Composition to be used as a plating resist in the manufacture of electronic circuitry.
U.S. Pat. No. 4,433,1739 pertains to a process for the preparation of allyl ethers. The allyl ethers are usable as monomers to be converted into cross-linked polymers, or as starting materials for the preparation of epoxide compounds.
U.S. Pat. No. 4,614,761 to Takiama, et al. pertains to a process for producing a curable resin having unsaturated groups and side chains through urethane linkages. The resin is produced by reacting a polymer having hydroxyl groups in the side chains with an unsaturated monoiosocyanate. The monoisocyanate is obtained by reacting one mole of diisocyanate with one mole of an unsaturated monoalcohol. The polymer having side chain hydroxyl groups can be produced by copolymerizing a final monomer having hydroxyl groups and another vinyl monomer. Allyl alcohol is specifically disclosed as undesirable as the material for synthesizing the polymer because it does not serve to increase the molecular weight of the polymer.
U.S. Pat. No. 5,236,978 discloses a polymerizable organic resin of a polyol (allyl carbonate) and an aliphatic polyurethane having terminal allylic unsaturation. The resulting polymer has low yellowness and can be used to prepare photochromic articles such as lenses.
The foregoing allyl functional resins are generally high molecular weight and high viscosity, which limit their applications and physical properties. Accordingly, there is a need to develop new allyl functional resins with low molecular weight and viscosity which will exhibit higher mobility and better surface cure. Such would be especially useful in coatings, adhesives and sealants. Furthermore, there is a continuing need to develop new resins which will possess different properties from those previously developed. Such new resins, while generally useful as coating compositions, will find applications for which they are specifically suited depending on the specific properties of the resin.
SUMMARY OF THE INVENTION
A new class of curable allyl functional urethanes have now been developed. These urethanes are free radical-curable oligomer compositions having the following formula: R
1
[NHCO(OR)
y
(OCH
2
CH═CH
2
)
m
]
n
wherein y is 0 or 1, n is an integer between 2 and 20, m is an integer between 1 and 5, R is a C
1
-C
10
alkyl, arylalkyl, alkenyl, aryl, alkynyl, (C
3
-C
10
)cycloalkyl, (C
3
-C
10
)cycloalkenyl or alkoxy, and R
1
is one of aryl, arylalkyl, (C
3
-C
10
)cycloalkyl, (C
3
-C
10
)cycloalkenyl or heterocyclic. Also set forth is a method for making a cured resin comprising reacting the oligomer compositions with a free radical initiator to cause cross-linking of the resins.
DETAILED DESCRIPTION OF THE INVENTION
The present invention relates to a new class of allyl functional urethanes and processes for their preparation and use. The new resin compositions are prepared by the reaction of hydroxyl-containing allyl functional materials with aliphatic, aromatic, or cycloaliphatic isocyanates. The new compositions are soluble in typical aliphatic and aromatic solvents and are curable using free radical-based initiators. The compositions are also compatible with typical polymerized monomers and polymers such as unsaturated polyesters.
The resins of the present invention are prepared through the reaction of hydroxyl-containing allyl materials with aliphatic or aromatic isocyanates. Preferably, the aliphatic or aromatic isocyanates include two or more isocyanate groups per molecule. As used herein, the term “aliphatic” refers to alkyl, alkenyl, alkynyl, cycloalkyl and cycloalkenyl groups, any of which may be substituted with up to three halogen atoms. The term “heterocyclic” means an aryl group with one hetero-atom selected from O, N, and S. Examples of isocyanates which are suitable for use in the present invention include isophorone diisocyanate, toluene diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, hexamethylene diisocyanate, 4,4′-methylene bis (phenyl isocyanate). Suitable isocyanates may also be dimers, trimers, and polymers. Specifically, Desmodur™ N 100 and N 3200 (aliphatic polyisocyanate resins based on hexamethylene diisocyanate (HDI)), Desmodur™ 3300 (a polyfunctional aliphatic isocyanate resin based on HDI) and Desmodur™ N 3400 (a polyfunctional aliphatic polyisocyanate resin based on HDI) all from Bayer Corp. are useful as isocyanates in the present invention. Desmodur is a trademark of Bayer Corporation of Pittsburgh, Pa., U.S.A.
The hydroxyl-containing allyl functional materials can be monoallylethers or polyallylethers. These allyl functional materials may be substituted with alkyl groups, halogens, or other conservative substituents. However, substitutions must be well thought out. Hydroxyl groups can be substituents only to the extent that reactivity with the isocyanate component is desired, and increasing the number of hydroxyl groups will change the proportions of allyl and isocyanate materials. Similarly, halogen substituents may be used. However, o

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