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US 8,912,303 B1Granted
Poly(hydroxyl urethane) compositions and methods of making and using the same
AssigneeU.S. Department of Energy
InventorsDavid Luebke, Hunaid Nulwala, Chau Tang
Life of this patent
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Abstract
Methods and compositions relating to poly(hydroxyl urethane) compounds are described herein that are useful as, among other things, binders and adhesives. The cross-linked composition is achieved through the reaction of a cyclic carbonate, a compound having two or more thiol groups, and a compound having two or more amine functional groups. In addition, a method of adhesively binding two or more substrates using the cross-linked composition is provided.
Claims6
A composition comprising a reaction product of;
- 1) one or more compounds having at least one cyclic carbonate group, wherein the cyclic carbonate comprises one or more functional groups having one or more carbon-carbon double bonds or triple bonds;
- 2) one or more compounds having two or more thiol groups,
- wherein the compound having two or more thiol groups has the structure:
- wherein R4 and R5 are CH2CH2SH, R6 is H and R7 is CH2;
- and,
- wherein R8 contains an aromatic group;
- 3) one or more compounds having two or more amine functional groups;
- and,
- wherein the product is a cross-linked poly(hydroxyl urethane).
6 more elements
A composition comprising a reaction product of:
- 1) one or more compounds having at least one cyclic carbonate group, wherein the cyclic carbonate comprises one or more functional groups having one or more carbon-carbon double bonds or triple bonds;
- 2) one or more compounds having two or more thiol groups,
- wherein the compound having two or more thiol groups has the structure:
- wherein R4, R5 and R6 are CH2COOCH2CH2SH and R7 is CH2CH3;
- and,
- wherein R8 contains an aromatic group;
- 3) one or more compounds having two or more amine functional groups;
- and,
- wherein the product is a cross-linked poly(hydroxyl urethane).
6 more elements
A composition comprising a reaction product of:
- 1) one or more compounds having at least one cyclic carbonate group, wherein the cyclic carbonate comprises one or more functional groups having one or more carbon-carbon double bonds or triple bonds;
- 2) one or more compounds having two or more thiol groups,
- wherein the compound having two or more thiol groups has the structure:
- wherein R4, R5, R6 and R7 are CH2COOCH2CH2SH;
- and,
- wherein R8 contains an aromatic group;
- 3) one or more compounds having two or more amine functional groups;
- and,
- wherein the product is a cross-linked poly(hydroxyl urethane).
6 more elements
A composition comprising a reaction product of:
- 1) one or more compounds having at least one cyclic carbonate group, wherein the cyclic carbonate comprises one or more functional groups having one or more carbon-carbon double bonds or triple bonds;
- 2) one or more compounds having two or more thiol groups;
- 3) one or more compounds having two or more amine functional groups,
- wherein the compound having three or more amine functional groups has the structure:
- wherein
- R9, R12, R13, R17, R19, R20 and R22 are each independently chosen from hydrogen and a straight chain or branched alkane or alkene, optionally substituted with at least one member selected from the group consisting of NH2, SH, COO and OH, and optionally containing from 1 to 8 ether bridges and/or from 1 to 3 tertiary amine bridges;
- R9 and R12 or R13 and/or R17 and/or R19 or R20 and R22 may be linked together to form a ring;
- R10 , R11, R14, R16, R18 and R21 are each independently chosen from a straight chain or branched alkane, alkene or alkyne, optionally substituted with at least one member selected from the group consisting of NH2, SH, COO and OH, and optionally containing from 1 to 8 ether bridges and/or from 1 to 3 tertiary amine bridges;
- and,
- R15 is hydrogen or alkyl;
- and,
- wherein the product is a cross-linked poly(hydroxyl urethane).
9 more elements
A composition comprising a reaction product of:
- 1) one or more compounds having at least one cyclic carbonate group, wherein the cyclic carbonate comprises one or more functional groups having one or more carbon-carbon double bonds or triple bonds,
- wherein the cyclic carbonate has the structure:
- wherein R1 is —(CR2R3)n—, wherein 2≦n≦4, and wherein R2 and R3 are each independently hydrogen, straight chain or branched alkane, alkene or alkyne, optionally substituted with at least one member selected from the group consisting of NH2, SH, COO and OH,
- and further wherein at least one R2 or R3 is a straight chain or branched alkene or alkyne;
- 2) one or more compounds having two or more thiol groups,
- wherein the compound having two or more thiol groups has the structure:
- wherein at least two of R4, R5, R6 and R7 are a thiol,
- further wherein R4, R5, R6 and R7 are each independently hydrogen, straight chain, branched or cyclic alkane, alkene or alkyne, or ester, and optionally substituted with at least one member selected from the group consisting of NH2, SH, COO, SiO and OH;
- and,
- 3) one or more compounds having two or more amine functional groups,
- wherein the compound having three or more amine functional groups has the structure:
- wherein:
- R9and R12 are each independently chosen from hydrogen and a straight chain or branched alkane or alkene, optionally substituted with at least one member selected from the group consisting of NH2, SH, COO and OH, and optionally containing from 1 to 8 ether bridges and/or from 1 to 3 tertiary amine bridges;
- R9 and R12 may be linked together to form a ring, and
- R10 and R11 are each independently chosen from a straight chain or branched alkane, alkene or alkyne, optionally substituted with at least one member selected from the group consisting of NH2, SH, COO and OH, and optionally containing from 1 to 8 ether bridges and/or from 1 to 3 tertiary amine bridges;
- and,
- wherein the product is a cross-linked poly(hydroxyl urethane.
14 more elements
A method of adhesively bonding two substrates comprising:
- 1) applying a composition to a first substrate and/or a second substrate;
- and,
- 2) contacting the first substrate with the second substrate via the applied composition;
- and,
- wherein the composition comprises a reaction product of:
- 1) one or more compounds having at least one cyclic carbonate group, wherein the cyclic carbonate comprises one or more functional groups having one or more carbon-carbon double bonds or triple bonds;
- 2) one or more compounds having two or more thiol groups;
- and,
- 3) one or more compounds having two or more amine functional groups;
- and
- wherein the product is a cross-linked poly(hydroxyl urethane).
8 more elements
Dependencies are inferred from the claim text.