Organoborane-containing compositions, and methods of using same

Patent metadata

Field	Value
Publication number	US-10513583-B2
Application number	US-201515129331-A
Country	US
Kind code	B2
Filing date	Mar 20, 2015
Priority date	Mar 27, 2014
Publication date	Dec 24, 2019
Grant date	Dec 24, 2019

Abstract

A polymerizable composition that includes: an organoborane-base complex, wherein the base is a complexing agent selected from a compound having one or more amine groups, amidine groups, hydroxide groups, alkoxide groups, or combinations thereof; a decomplexing agent that liberates the organoborane from the organoborane-base complex; a polymerizable thiol-containing component that includes at least one polymerizable thiol-containing compound having a plurality of thiol groups in which the sulfur atom of the thiol group is covalently bonded to carbon; and a polymerizable ethylenically unsaturated component that includes at least one polymerizable ethylenically unsaturated compound having a plurality of ethylenically unsaturated groups; wherein the total amount of the thiol-containing and ethylenically unsaturated compounds total at least 50% by weight of all polymerizable material in the composition.

First claim

What is claimed is:

1. A polymerizable composition comprising:
an organoborane-base complex, wherein the base is a complexing agent selected from a compound having one or more amine groups, amidine groups, hydroxide groups, alkoxide groups, or a combination thereof, wherein the complexing agent is free of aziridines;
a decomplexing agent that liberates the organoborane from the organoborane-base complex, wherein the decomplexing agent comprises a 1,3-dicarbonyl compound;
a polymerizable thiol-containing component comprising at least one polymerizable thiol-containing compound having a plurality of thiol groups in which the sulfur atom of the thiol group is covalently bonded to carbon; and
a polymerizable ethylenically unsaturated component comprising at least one polymerizable ethylenically unsaturated compound having a plurality of ethylenically unsaturated groups;
wherein the total amount of the thiol-containing and ethylenically unsaturated compounds total at least 50% by weight of all polymerizable material in the composition.

2. The polymerizable composition of claim 1 , wherein upon reaction a —C—S—C—C— linkage is formed.

3. The polymerizable composition of claim 1 , wherein the thiol-containing compound and the ethylenically unsaturated compound are separate and distinct compounds.

4. The polymerizable composition of claim 1 , wherein the organoborane-base complex does not include a thiol group.

5. The polymerizable composition of claim 1 , wherein the organoborane portion of the organoborane-base complex is of the formula B(R 1 )(R 2 )(R 3 ) wherein:
R 1 represents an alkyl group having from 1 to 10 carbon atoms; and
R 2 and R 3 independently represent:
alkyl groups having 1 to 10 carbon atoms;
cycloalkyl groups having 3 to 10 carbon atoms;
aryl groups having 6 to 12 carbon atoms; or
aryl groups substituted with alkyl groups having 1 to 10 carbon atoms or cycloalkyl groups having 3 to 10 carbon atoms;

provided that any two of R 1 , R 2 , and R 3 groups may optionally be part of a ring.

6. The polymerizable composition of claim 1 , wherein the base portion of the organoborane-base complex is an amine comprising at least one primary or secondary amine group.

7. The polymerizable composition of claim 1 , wherein the polymerizable composition is a multi-part polymerizable composition.

8. The polymerizable composition of claim 1 , wherein the multi-part polymerizable composition comprises:
a part A composition comprising the organoborane-base complex; and
a part B composition comprising the decomplexing agent;
wherein the thiol-containing compound is in part A, part B, or another part distinct from parts A and B; and
wherein the ethylenically unsaturated compound is in part A, part B, or another part distinct from parts A and B.

9. The polymerizable composition of claim 1 , wherein the thiol-containing component comprises at least one polymerizable thiol-containing compound selected from those prepared from a ring-opening reaction of epoxides with H 2 S, those prepared from the addition of H 2 S across carbon-carbon double bonds, polysulfides, polydimethylsiloxanes in which some of the methyl groups have been replaced by mercaptoalkyl groups, and those prepared from the esterification of polyols with thiol-containing carboxylic acids or their derivatives.

10. The polymerizable composition of claim 1 , wherein the ethylenically unsaturated compound is selected from polyfunctional vinyl ethers, vinyl silicones, vinyl aliphatics, (meth)acrylates, allyl ethers, allyl esters, and allyl amides.

11. The polymerizable composition of claim 1 , wherein the amount of the thiol groups in the thiol-containing component and the amount of the ethylenically unsaturated groups in the ethylenically unsaturated component are in a molar ratio range of 0.25:1.0 to 4.0:1.0.

12. A polymerizable composition comprising:
a part A composition comprising an organoborane-base complex, wherein the base is a complexing agent selected from a compound having one or more amine groups, amidine groups, hydroxide groups, alkoxide groups, or a combination thereof, wherein the complexing agent is free of aziridines; and
a part B composition comprising a decomplexing agent that liberates the organoborane from the organoborane-base complex, wherein the decomplexing agent comprises a 1,3-dicarbonyl compound;
wherein the polymerizable composition further comprises:
a polymerizable thiol-containing component comprising at least one polymerizable thiol-containing compound having a plurality of thiol groups in which the sulfur atom of the thiol group is covalently bonded to carbon; and
a polymerizable ethylenically unsaturated component comprising at least one polymerizable ethylenically unsaturated compound having a plurality of ethylenically unsaturated groups;

wherein the total amount of the thiol-containing and ethylenically unsaturated compounds total at least 50% by weight of all polymerizable material in the composition.

13. The polymerizable composition of claim 12 , wherein upon reaction a —C—S—C—C— linkage is formed.

14. The polymerizable composition of claim 12 , wherein the organoborane portion of the organoborane-base complex is of the formula B(R 1 )(R 2 )(R 3 ) wherein:
R 1 represents an alkyl group having from 1 to 10 carbon atoms; and
R 2 and R 3 independently represent:
alkyl groups having 1 to 10 carbon atoms;
cycloalkyl groups having 3 to 10 carbon atoms;
aryl groups having 6 to 12 carbon atoms; or
aryl groups substituted with alkyl groups having 1 to 10 carbon atoms or cycloalkyl groups having 3 to 10 carbon atoms;

provided that any two of R 1 , R 2 , and R 3 groups may optionally be part of a ring.

15. The polymerizable composition of claim 12 , wherein the base portion of the organoborane-base complex is an amine comprising at least one primary or secondary amine group.

16. A composition prepared by combining components comprising:
a part A composition comprising an organoborane-base complex, wherein the base is a complexing agent selected from a compound having one or more amine groups, one or more amidine groups, one or more hydroxide groups, one or more alkoxide groups, or a combination thereof, wherein the complexing agent is free of aziridines; and
a part B composition comprising a decomplexing agent that liberates the organoborane from the organoborane-base complex, wherein the decomplexing agent comprises a 1,3-dicarbonyl compound;
wherein the part A composition and/or the part B composition further comprises:
a polymerizable thiol-containing component comprising at least one polymerizable thiol-containing compound having a plurality of thiol groups in which the sulfur atom of the thiol group is covalently bonded to carbon; and
a polymerizable ethylenically unsaturated component comprising at least one polymerizable ethylenically unsaturated compound having a plurality of ethylenically unsaturated groups;

wherein the total amount of the thiol-containing and ethylenically unsaturated compounds total at least 50% by weight of all polymerizable material in the composition.

17. The composition of claim 16 , wherein the organoborane portion of the organoborane-base complex is of the formula B(R 1 )(R 2 )(R 3 ) wherein:
R 1 represents an alkyl group having from 1 to 10 carbon atoms; and
R 2 and R 3 independently represent:
alkyl groups having 1 to 10 carbon atoms;
cycloalkyl groups having 3 to 10 carbon atoms;
aryl groups having 6 to 12 carbon atoms; or
aryl groups substituted with alkyl groups having 1 to 10 carbon atoms or c

Assignees

• 3M Innovative Properties Co

Inventors

• Clough Robert S
• Karp Gregory P
• Thompson Zachary J
• Joly Guy D

Classifications

• C09J183/08

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen · CPC title

• C08F222/103

  of trialcohols, e.g. trimethylolpropane tri(meth)acrylate · CPC title

• C08F236/20

  unconjugated · CPC title

• C08F4/54 Primary

  together with other compounds thereof · CPC title

• C09D183/08

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen · CPC title