Coupling agent

Abstract

Disclosed are thermoset compositions comprising a dispersion obtained by dispersing particulate solids into a thermoset resin in the presence of a coupling agent according to Formula I as described herein. Various methods of making and / or using the coupling agent and / or the thermoset composition are also disclosed.

Description

[0001] The disclosed technology relates to polymers useful as coupling agents, such as in thermosetting compositions including particulate solids.

[0002] It is known to incorporate particulate solids (e.g., fillers and / or fibers) into polymeric materials such as thermosetting polymers, thermoplastic polymers, elastomers, and / or rubbers; combinations of these materials represent a subset of composite materials. Molded articles made from these types of composite materials may exhibit improved stiffness, hardness, and / or creep resistance compared to the corresponding unfilled polymeric materials. However, these types of composite materials may exhibit a significant reduction in toughness and / or ductility compared to the corresponding unfilled polymeric materials. In the case of thermoplastic polymers and thermosetting polymers, composite molded articles may become too brittle, or have too low impact resistance and elongation to be of much practical use.

[0003] Various methods have been tried to improve the compatibility of particulate solids with polymeric materials to improve such defects. For example, incorporation of surface modifiers or adhesives, such as by coating the particulate solids, can improve compatibility. Surface modifiers / adhesives can generally be divided into two categories: coupling agents and non-coupling modifiers. Non-coupling modifiers interact with the surface of the particulate solids but do not interact with the polymer matrix.

[0004] The coupling agent interacts with both the surface of the particulate solid and the polymer matrix. In many cases, the coupling agent is covalently bonded to both the particulate solid and the polymer matrix. In other cases, ion pair interactions between the coupling agent and the particulate solid may be sufficient, while chain entanglement and / or co-crystallization may provide sufficient interaction between the coupling agent and the polymer matrix.

[0005] For example, acid functional modifiers can be represented in both categories. Certain fatty acids can generally be considered as non-coupling modifiers, where the carboxyl groups are bound to the surface of the particulate solid and the fatty groups are embedded in the polymer matrix. Certain polymeric acids can generally be considered as coupling agents, where the carboxyl groups interact with the surface of the particulate solid and the polymer chains interact with the polymer matrix. The degree of interaction between the polymer chains and the polymer matrix depends on the functionality of the polymer chains and the type of polymer material. For example, acrylic acid has been used as a coupling agent for calcium carbonate fillers in a polypropylene matrix, but the volatility of acrylic acid during processing presents a significant disadvantage.

[0006] Organosilanes are currently used as coupling agents. Organosilanes contain alkoxysilane groups that can react with suitable hydroxyl groups on the surface of particulate solids (e.g., in the case of metal hydroxide fillers, to form [metal]-O-Si covalent bonds). Organosilanes coupling agents also have another functional group that can react with a polymer matrix. A wide range of commercially available organosilanes coupling agents can be used to treat surface hydroxyl groups of different reactivity and different reactions with polymer chains in the matrix. Organosilanes can be very effective, but they do have certain limitations. For example, they may be relatively expensive due to the need for complex chemical processing, they may be ineffective for fillers that do not have surface hydroxyl groups, they may have limited compatibility with the bulk polymer material used (and therefore can be applied to particulate solids as a surface treatment, requiring additional process steps and / or limiting processing conditions), and they may release a large amount of alcohol when reacting with the surface of certain particulate solids.

[0007] Thus, the disclosed technology provides polymers useful as coupling agents that overcome some of the above-mentioned deficiencies.

[0008] The subject matter disclosed herein provides a polymer having monomer units a, b, c, d, e and f according to formula I:

[0009]

[0010] Wherein for each molecule of the polymer independently:

[0011] R 1 is H or CH3;

[0012] R 2 H, C1-C 20 Alkyl groups, C6-C 10 Aryl group, C7-C 14 an alkylaryl group or a C4-C6 cycloalkyl group;

[0013] X 1 is 2 or 3 carbon atoms, where if X 1 If there are 3 carbon atoms, one of the carbon atoms is not included in the polymer main chain;

[0014] X 2 is 2 or 3 carbon atoms, where if X 2 If there are 3 carbon atoms, one of the carbon atoms is not included in the polymer main chain;

[0015] R 3 is H or CH3;

[0016] R 4 For C1 to C20 Alkyl group, -COR 7 -or-(C=O)-OCR 7 -, where R 7 For C1 to C 20 Alkyl groups;

[0017] X 3 is 2 or 3 carbon atoms, where if X 3 If there are 3 carbon atoms, one of the carbon atoms is not included in the polymer main chain;

[0018] R 5 is H or CH3;

[0019] R 6 For C1 to C 20 Alkyl group, -COR 8 -or-(C=O)-OCR 8 -, where R 8 For C1 to C 20 Alkyl groups;

[0020] Z 1 NH or O;

[0021] X 4 is 2 or 3 carbon atoms, where if X 4 If there are 3 carbon atoms, one of the carbon atoms is not included in the polymer main chain;

[0022] POL 1 is a polymer comprising at least one of a polyether or a polyester, wherein the polymer has a theoretical number average molecular weight of 200 to 3,000;

[0023] X 5 is 2 or 3 carbon atoms, where if X 5 If there are 3 carbon atoms, one of the carbon atoms is not included in the polymer main chain;

[0024] POL 2 is a polymer comprising at least one of a polyether or a polyester, wherein the polymer has a theoretical number average molecular weight of 200 to 3,000;

[0025] Z 2 NH or O;

[0026] a is an integer between 1 and 500;

[0027] b is an integer between 1 and 500;

[0028] c is 0, or an integer between 1 and 100;

[0029] d is 0, or an integer between 1 and 100;

[0030] e is 0, or an integer between 1 and 100; and

[0031] f is 0, or an integer between 1 and 100;

[0032] Where: if c is 0, then d is at least 1; if d is 0, then c is at least 1; if e is 0, then f is at least 1; and if f is 0, then e is at least 1.

[0033] In certain embodiments, the polymer may be used as a coupling agent in a thermosetting composition.For example, the thermosetting composition may comprise a dispersion obtained by dispersing a particulate solid in a thermosetting resin in the presence of a coupling agent.

[0034] Various methods of making and / or using the polymers, coupling agents and / or thermosetting compositions are also provided.

[0035] The following implementations of the present subject matter are contemplated:

[0036] 1. A thermosetting composition comprising a dispersion obtained by dispersing a particulate solid in a thermosetting resin in the presence of a coupling agent, the coupling agent comprising monomer units a, b, c, d, e and f according to formula I:

[0037]

[0038] Wherein for each molecule of the polymer independently:

[0039] R 1 is H or CH3;

[0040] R 2 H, C1-C 20 Alkyl groups, C6-C 10 Aryl group, C7-C 14 an alkylaryl group or a C4-C6 cycloalkyl group;

[0041] X 1 is 2 or 3 carbon atoms, where if X 1 If there are 3 carbon atoms, one of the carbon atoms is not included in the polymer main chain;

[0042] X 2 is 2 or 3 carbon atoms, where if X 2 If there are 3 carbon atoms, one of the carbon atoms is not included in the polymer main chain;

[0043] R 3 is H or CH3;

[0044] R4 For C1 to C 20 Alkyl group, -COR 7 -or-(C=O)-OCR 7 -, where R 7 For C1 to C 20 Alkyl groups;

[0045] X 3 is 2 or 3 carbon atoms, where if X 3 If there are 3 carbon atoms, one of the carbon atoms is not included in the polymer main chain;

[0046] R 5 is H or CH3;

[0047] R 6 For C1 to C 20 Alkyl group, -COR 8 -or-(C=O)-OCR 8 -, where R 8 For C1 to C 20 Alkyl groups;

[0048] Z 1 NH or O;

[0049] X 4 is 2 or 3 carbon atoms, where if X 4 If there are 3 carbon atoms, one of the carbon atoms is not included in the polymer main chain;

[0050] POL 1 is a polymer comprising at least one of a polyether or a polyester, wherein the polymer has a theoretical number average molecular weight of 200 to 3,000;

[0051] X 5 is 2 or 3 carbon atoms, where if X 5 If there are 3 carbon atoms, one of the carbon atoms is not included in the polymer main chain;

[0052] POL 2 is a polymer comprising at least one of a polyether or a polyester, wherein the polymer has a theoretical number average molecular weight of 200 to 3,000;

[0053] Z 2 NH or O;

[0054] a is an integer between 1 and 500;

[0055] b is an integer between 1 and 500;

[0056] c is 0, or an integer between 1 and 100;

[0057] d is 0, or an integer between 1 and 100;

[0058] e is 0, or an integer between 1 and 100; and

[0059] f is 0, or an integer between 1 and 100;

[0060] Where: if c is 0, then d is at least 1; if d is 0, then c is at least 1; if e is 0, then f is at least 1; and if f is 0, then e is at least 1.

[0061] 2. The thermosetting composition according to embodiment 1, wherein the particulate solid is present in an amount of 20 wt % to 80 wt %, based on the total weight of the thermosetting composition.

[0062] 3. The thermosetting composition according to embodiment 1 or embodiment 2, wherein the particulate solid comprises at least one of an extender, a reinforcing material, or a functional filler.

[0063] 4. The thermosetting composition according to embodiment 3, wherein the extender comprises at least one of calcium carbonate, talc, barium sulfate, aluminum oxide or quartz.

[0064] 5. The thermosetting composition according to embodiment 3 or embodiment 4, wherein the reinforcing material comprises at least one type of fiber material.

[0065] 6. The thermosetting composition according to any one of embodiments 3 to 5, wherein the functional filler comprises at least one of a flame retardant material or a pigment.

[0066] 7. The thermosetting composition according to any one of embodiments 1 to 6, wherein the thermosetting resin is present in an amount of 80 wt % to 20 wt % based on the total weight of the thermosetting composition.

[0067] 8. The thermosetting composition according to any one of embodiments 1 to 7, wherein the thermosetting resin comprises an epoxy resin, an unsaturated polyester resin, a vinyl ester resin, a polyurethane resin or a phenolic resin.

[0068] 9. The thermosetting composition according to any one of embodiments 1 to 8, wherein the coupling agent is present in an amount of 0.5 wt % to 5 wt %, based on the total weight of the thermosetting composition.

[0069] 10. The thermosetting composition according to any one of embodiments 1 to 9, wherein the coupling agent comprises at least 90 wt.% of monomer units a, b, c, d, e and f according to formula I, based on the total weight of the coupling agent.

[0070] 11. The thermosetting composition according to any one of embodiments 1 to 10, wherein the coupling agent comprises at least 70 wt.% of monomer units a and b according to formula I, based on the total weight of the coupling agent.

[0071] 12. The thermosetting composition according to any one of embodiments 1 to 11, wherein the coupling agent comprises no more than 30 wt.% of monomer units c, d, e and f according to formula I, based on the total weight of the coupling agent.

[0072] 13. The thermosetting composition according to any one of embodiments 1 to 12, wherein the coupling agent comprises at least 50 wt.% of monomer units a according to formula I, based on the total weight of the coupling agent.

[0073] 14. The thermosetting composition according to any one of embodiments 1 to 13, wherein the coupling agent comprises no more than 40 wt.% of monomer units b according to formula I, based on the total weight of the coupling agent.

[0074] 15. The thermosetting composition according to any one of embodiments 1 to 14, wherein a is an integer from 5 to 500.

[0075] 16. The thermosetting composition according to any one of embodiments 1 to 15, wherein a is an integer from 20 to 50.

[0076] 17. The thermosetting composition according to any one of embodiments 1 to 16, wherein b is an integer from 2 to 100.

[0077] 18. The thermosetting composition according to any one of embodiments 1 to 17, wherein b is an integer from 3 to 12.

[0078] 19. The thermosetting composition according to any one of embodiments 1 to 18, wherein the ratio of a to b is from 1:1 to 10:1.

[0079] 20. The thermosetting composition according to any one of embodiments 1 to 19, wherein c is an integer from 3 to 12.

[0080] 21. The thermosetting composition according to any one of embodiments 1 to 20, wherein d is an integer from 3 to 12.

[0081] 22. The thermosetting composition according to any one of embodiments 1 to 21, wherein e is an integer from 4 to 16.

[0082] 23. The thermosetting composition according to any one of embodiments 1 to 22, wherein f is an integer from 4 to 16.

[0083] 24. The thermosetting composition according to any one of embodiments 1 to 23, wherein the coupling agent comprises up to 10% by weight of other monomer units other than monomer units a, b, c, d, e and f according to formula I.

[0084] Various features and embodiments of the present subject matter are described below by way of non-limiting illustration.

[0085] As used herein, the indefinite article "a" / "an" is intended to mean one or more than one / one or more than one. As used herein, the phrase "at least one / at least one" means one or more than one / one or more than one of the following terms. Therefore, "a" / "an" and "at least one / at least one" can be used interchangeably. For example, "at least one of A, B or C" means that in alternative embodiments, only one of A, B or C may be included, and any mixture of two or more of A, B and C may be included.

[0086] As used herein, the term "substantially" means that the value of a given amount is within ±10% of the specified value. In other embodiments, the value is within ±5% of the specified value. In other embodiments, the value is within ±2.5% of the specified value. In other embodiments, the value is within ±1% of the specified value.

[0087] As used herein, the transitional term "comprising," which is synonymous with "comprising," "containing," or "characterized by," is inclusive or open-ended and does not exclude additional, unrecited elements or method steps. However, in each use of "comprising" herein, it is intended that the term also encompasses the phrases "consisting essentially of" and "consisting of" as alternative embodiments, wherein "consisting of" excludes any element or step not specified, and "consisting essentially of" permits the inclusion of additional, unrecited elements or steps that do not materially affect the essential or basic and novel characteristics of the composition or method under consideration.

[0088] Provided is a thermosetting composition comprising a dispersion obtained by dispersing a particulate solid in a thermosetting resin in the presence of a coupling agent, the coupling agent comprising monomer units a, b, c, d, e and f according to formula I:

[0089]

[0090] Wherein for each molecule of the polymer independently:

[0091] R 1 is H or CH3;

[0092] R 2 H, C1-C 20 Alkyl groups, C6-C 10Aryl group, C7-C 14 an alkylaryl group or a C4-C6 cycloalkyl group;

[0093] X 1 is 2 or 3 carbon atoms, where if X 1 If there are 3 carbon atoms, one of the carbon atoms is not included in the polymer main chain;

[0094] X 2 is 2 or 3 carbon atoms, where if X 2 If there are 3 carbon atoms, one of the carbon atoms is not included in the polymer main chain;

[0095] R 3 is H or CH3;

[0096] R 4 For C1 to C 20 Alkyl group, -COR 7 -or-(C=O)-OCR 7 -, where R 7 For C1 to C 20 Alkyl groups;

[0097] X 3 is 2 or 3 carbon atoms, where if X 3 If there are 3 carbon atoms, one of the carbon atoms is not included in the polymer main chain;

[0098] R 5 is H or CH3;

[0099] R 6 For C1 to C 20 Alkyl group, -COR 8 -or-(C=O)-OCR 8 -, where R 8 For C1 to C 20 Alkyl groups;

[0100] Z 1 NH or O;

[0101] X 4 is 2 or 3 carbon atoms, where if X 4 If there are 3 carbon atoms, one of the carbon atoms is not included in the polymer main chain;

[0102] POL 1is a polymer comprising at least one of a polyether or a polyester, wherein the polymer has 200 to 3,000 (such as 250 to 3,000, 300 to 3,000, 350 to 3,000, 400 to 3,000, 450 to 3,000, 500 to 3,000, 600 to 3,000, 700 to 3,000, 800 to 3,000, 900 to 3,000, 1,000 to 3,000, 1,200 to 3,000, 1,400 to 3,000, 1,600 to 3,000, 1,800 to 3,000, 2,000 to 3,000, 2,500 to 3,000, 200 to 2,500, 250 to 2,500, 300 to 2, 500, 350 to 2,500, 400 to 2,500, 450 to 2,500, 500 to 2,500, 600 to 2,500, 700 to 2,500, 800 to 2,500, 900 to 2,500, 1,000 to 2,500, 1,200 to 2,500, 1,400 to 2,500, 1,600 0 to 2,500, 1,800 to 2,500, 2,000 to 2,500, 200 to 2,000, 250 to 2,000, 300 to 2,000, 350 to 2,000, 400 to 2,000, 450 to 2,000, 500 to 2,000, 600 to 2,000, 700 to 2,000, 800 to 2,000, 900 to 2,000, 1,000 to 2,000, 1,200 to 2,000, 1,400 to 2,000, 1,600 to 2,000, 1,800 to 2,000, 200 to 1,800, 250 to 1,800, 300 to 1,800, 350 to 1,800, 400 to 1,8 00, 450 to 1,800, 500 to 1,800, 600 to 1,800, 700 to 1,800, 800 to 1,800, 900 to 1,800, 1,000 to 1,800, 1,200 to 1,800, 1,400 to 1,800, 1,600 to 1,800, 200 to 1,600, 250 to 1,600, 300 to 1,600, 350 to 1,600, 400 to 1,600, 450 to 1,600, 500 to 1,600, 600 to 1,600, 700 to 1,600, 800 to 1,600, 900 to 1,600, 1,000 to 1,600, 1,200 to 1,600, 1,400 to 1,600, 200 to 1,400, 250 to 1,400, 300 to 1,400, 350 to 1,400, 400 to 1,400, 450 to 1,400, 500 to 1,400, 600 to 1,400, 700 to 1,400, 800 to 1,400, 900 to 1,400, 1,000 to 1,400, 1,200 to 1,400, 200 to 1,200, 250 to 1,200, 300 to 1,200, 350 to 1,200, 400 to 1,200, 450 to 1,200, 500 to 1,200, 600 to 1,200, 700 to 1,200, 800 to 1,200, 900 to 1,200, 1,000 to 1,200, 200 to 1, 000, 250 to 1,000, 300 to 1,000, 350 to 1,000, 400 to 1,000, 450 to 1,000, 500 to 1,000, 600 to 1,000, 700 to 1,000, 800 to 1,000, 900 to 1,000, 200 to 900, 250 to 900, 300 to 900, 350 to 900, 400 to 900, 4 50 to 900, 500 to 900, 600 to 900, 700 to 900, 800 to 900, 200 to 800, 250 to 800, 300 to 800, 350 to 800, 400 to 800, 450 to 800, 500 to 800, 600 to 800, 700 to 800, 200 to 700, 250 to 700, 300 to 700, 350 to 700, 4 00 to 700, 450 to 700, 500 to 700, 600 to 700, 200 to 600, 250 to 600, 300 to 600, 350 to 600, 400 to 600, 450 to 600, 500 to 600, 200 to 500, 250 to 500, 300 to 500, 350 to 500, 400 to 500 or 450 to 500);

[0103] X 5 is 2 or 3 carbon atoms, where if X 5 If there are 3 carbon atoms, one of the carbon atoms is not included in the polymer main chain;

[0104] POL 2is a polymer comprising at least one of a polyether or a polyester, wherein the polymer has 200 to 3,000 (such as 250 to 3,000, 300 to 3,000, 350 to 3,000, 400 to 3,000, 450 to 3,000, 500 to 3,000, 600 to 3,000, 700 to 3,000, 800 to 3,000, 900 to 3,000, 1,000 to 3,000, 1,200 to 3,000, 1,400 to 3,000, 1,600 to 3,000, 1,800 to 3,000, 2,000 to 3,000, 2,500 to 3,000, 200 to 2,500, 250 to 2,500, 300 to 2, 500, 350 to 2,500, 400 to 2,500, 450 to 2,500, 500 to 2,500, 600 to 2,500, 700 to 2,500, 800 to 2,500, 900 to 2,500, 1,000 to 2,500, 1,200 to 2,500, 1,400 to 2,500, 1,600 0 to 2,500, 1,800 to 2,500, 2,000 to 2,500, 200 to 2,000, 250 to 2,000, 300 to 2,000, 350 to 2,000, 400 to 2,000, 450 to 2,000, 500 to 2,000, 600 to 2,000, 700 to 2,000, 800 to 2,000, 900 to 2,000, 1,000 to 2,000, 1,200 to 2,000, 1,400 to 2,000, 1,600 to 2,000, 1,800 to 2,000, 200 to 1,800, 250 to 1,800, 300 to 1,800, 350 to 1,800, 400 to 1,8 00, 450 to 1,800, 500 to 1,800, 600 to 1,800, 700 to 1,800, 800 to 1,800, 900 to 1,800, 1,000 to 1,800, 1,200 to 1,800, 1,400 to 1,800, 1,600 to 1,800, 200 to 1,600, 250 to 1,600, 300 to 1,600, 350 to 1,600, 400 to 1,600, 450 to 1,600, 500 to 1,600, 600 to 1,600, 700 to 1,600, 800 to 1,600, 900 to 1,600, 1,000 to 1,600, 1,200 to 1,600, 1,400 to 1,600, 200 to 1,400, 250 to 1,400, 300 to 1,400, 350 to 1,400, 400 to 1,400, 450 to 1,400, 500 to 1,400, 600 to 1,400, 700 to 1,400, 800 to 1,400, 900 to 1,400, 1,000 to 1,400, 1,200 to 1,400, 200 to 1,200, 250 to 1,200, 300 to 1,200, 350 to 1,200, 400 to 1,200, 450 to 1,200, 500 to 1,200, 600 to 1,200, 700 to 1,200, 800 to 1,200, 900 to 1,200, 1,000 to 1,200, 200 to 1, 000, 250 to 1,000, 300 to 1,000, 350 to 1,000, 400 to 1,000, 450 to 1,000, 500 to 1,000, 600 to 1,000, 700 to 1,000, 800 to 1,000, 900 to 1,000, 200 to 900, 250 to 900, 300 to 900, 350 to 900, 400 to 900, 4 50 to 900, 500 to 900, 600 to 900, 700 to 900, 800 to 900, 200 to 800, 250 to 800, 300 to 800, 350 to 800, 400 to 800, 450 to 800, 500 to 800, 600 to 800, 700 to 800, 200 to 700, 250 to 700, 300 to 700, 350 to 700, 4 00 to 700, 450 to 700, 500 to 700, 600 to 700, 200 to 600, 250 to 600, 300 to 600, 350 to 600, 400 to 600, 450 to 600, 500 to 600, 200 to 500, 250 to 500, 300 to 500, 350 to 500, 400 to 500 or 450 to 500);

[0105] Z 2 NH or O;

[0106] a is an integer between 1 and 500;

[0107] b is an integer between 1 and 500;

[0108] c is 0, or an integer between 1 and 100;

[0109] d is 0, or an integer between 1 and 100;

[0110] e is 0, or an integer between 1 and 100; and

[0111] f is 0, or an integer between 1 and 100;

[0112] Where: if c is 0, then d is at least 1; if d is 0, then c is at least 1; if e is 0, then f is at least 1; and if f is 0, then e is at least 1.

[0113] The phrase "comprising monomeric units a, b, c, d, e and f according to formula I" should be understood to simply mean that the monomeric units described in the variable definitions provided for formula I exist (or optionally do not exist, such as with respect to monomeric units c, d, e and f), and it is also possible to include other monomeric units different from monomeric units a, b, c, d, e and / or f; the phrase is not intended to indicate that all monomeric units must exist, or exclude other monomeric units. In addition, it should be understood that monomeric units can (perhaps possibly will) be included in any order (such as a random order), rather than in the order shown in formula I (although it is possible that monomeric units can be present in the block copolymer structure in the order shown in formula I or in any other order in theory). In the implementation process, it may be difficult to control the position of each monomeric unit relative to any other monomeric unit, which will generally result in a random structure; however, as understood by those skilled in the relevant art, the number of units of each monomeric unit present can be controlled.

[0114] By "theoretical number average molecular weight" is meant the average molecular weight of a subject group of bonded atoms determined by adding the molecular weights of each atom of the group based on its chemical formula.

[0115] When the variable X 1 , X 2 , X 3 , X 4 and X 5 When any of X can represent 3 carbon atoms, the phrase "not included in the polymer backbone" means that one of the 3 carbon atoms is not identical to other atoms present in the polymer backbone, but is associated with a side group attached to the backbone. For example, to illustrate this concept, X 1 , X 2 , X 3 , X 4 and X 5 Each of X may be derived from, but is not limited to, maleic anhydride or itaconic anhydride. If derived from maleic anhydride, the corresponding X 1 , X 2 , X 3 , X 4 or X 5 The variable represents 2 carbon atoms, and the relevant part of the polymer will look like this:

[0116]

[0117] If derived from itaconic anhydride, the corresponding X 1 , X 2 , X 3 , X 4 or X 5 The variable will represent 3 carbon atoms and the relevant portion of the polymer will look like this:

[0118]

[0119] In certain embodiments, the particulate solids are present in an amount of 20 to 80 wt %, such as 25 to 80 wt %, 30 to 80 wt %, 35 to 80 wt %, 40 to 80 wt %, 45 to 80 wt %, 50 to 80 wt %, 55 to 80 wt %, 60 to 80 wt %, 65 to 80 wt %, 70 to 80 wt %, 75 to 80 wt %, 20 to 75 wt %, 25 to 75 wt %, 30 to 75 wt %, 35 to 75 wt %, 40 to 75 wt %, 45 to 75 wt %, %, 50% to 75% by weight, 55% to 75% by weight, 60% to 75% by weight, 65% to 75% by weight, 70% to 75% by weight, 20% to 70% by weight, 25% to 70% by weight, 30% to 70% by weight, 35% to 70% by weight, 40% to 70% by weight, 45% to 70% by weight, 50% to 70% by weight, 55% to 70% by weight, 60% to 70% by weight, 65% to 70% by weight, 20% to 65% by weight, 25% to 65% by weight, 30% to 65% by weight, 35% to 65% by weight, 40% to 65% by weight %, 45% to 65% by weight, 50% to 65% by weight, 55% to 65% by weight, 60% to 65% by weight, 20% to 60% by weight, 25% to 60% by weight, 30% to 60% by weight, 35% to 60% by weight, 40% to 60% by weight, 45% to 60% by weight, 50% to 60% by weight, 55% to 60% by weight, 20% to 55% by weight, 25% to 55% by weight, 30% to 55% by weight, 35% to 55% by weight, 40% to 55% by weight, 45% to 55% by weight, 50% to 55% by weight, 20% to 50% by weight, 25% to 55% by weight % to 50 wt%, 30 wt% to 50 wt%, 35 wt% to 50 wt%, 40 wt% to 50 wt%, 45 wt% to 50 wt%, 20 wt% to 45 wt%, 25 wt% to 45 wt%, 30 wt% to 45 wt%, 35 wt% to 45 wt%, 40 wt% to 45 wt%, 20 wt% to 40 wt%, 25 wt% to 40 wt%, 30 wt% to 40 wt%, 35 wt% to 40 wt%, 20 wt% to 35 wt%, 25 wt% to 35 wt%, 30 wt% to 35 wt%, 20 wt% to 30 wt%, 25 wt% to 30 wt%, or 20 wt% to 25 wt%).The particulate solid may be any solid material suitable for incorporation into a thermosetting resin, such as to form a composite material. Particulate solids of varying densities may be included in the thermosetting resin, depending on the intended use of the resulting composition and / or the desired properties of the resulting composition. Thus, the weight % of particulate solid present in the composition may vary widely based on both the density and the amount of particulate solid present.

[0120] In certain embodiments, the particulate solids are present in an amount of 20% to 80% by volume (e.g., 25% to 80% by volume, 30% to 80% by volume, 35% to 80% by volume, 40% to 80% by volume, 45% to 80% by volume, 50% to 80% by volume, 55% to 80% by volume, 60% to 80% by volume, 65% to 80% by volume, 70% to 80% by volume, 75% to 80% by volume, 20% to 75% by volume, 25% to 75% by volume, 30% to 75% by volume, 35% to 75% by volume, 40% to 75% by volume, 45% to 75% by volume, %, 50% to 75% by volume, 55% to 75% by volume, 60% to 75% by volume, 65% to 75% by volume, 70% to 75% by volume, 20% to 70% by volume, 25% to 70% by volume, 30% to 70% by volume, 35% to 70% by volume, 40% to 70% by volume, 45% to 70% by volume, 50% to 70% by volume, 55% to 70% by volume, 60% to 70% by volume, 65% to 70% by volume, 20% to 65% by volume, 25% to 65% by volume, 30% to 65% by volume, 35% to 65% by volume, 40% to 65% by volume %, 45% to 65% by volume, 50% to 65% by volume, 55% to 65% by volume, 60% to 65% by volume, 20% to 60% by volume, 25% to 60% by volume, 30% to 60% by volume, 35% to 60% by volume, 40% to 60% by volume, 45% to 60% by volume, 50% to 60% by volume, 55% to 60% by volume, 20% to 55% by volume, 25% to 55% by volume, 30% to 55% by volume, 35% to 55% by volume, 40% to 55% by volume, 45% to 55% by volume, 50% to 55% by volume, 20% to 50% by volume, 25% to 55% by volume %, 30% to 50% by volume, 35% to 50% by volume, 40% to 50% by volume, 45% to 50% by volume, 20% to 45% by volume, 25% to 45% by volume, 30% to 45% by volume, 35% to 45% by volume, 40% to 45% by volume, 20% to 40% by volume, 25% to 40% by volume, 30% to 40% by volume, 35% to 40% by volume, 20% to 35% by volume, 25% to 35% by volume, 30% to 35% by volume, 20% to 30% by volume, 25% to 30% by volume, or 20% to 25% by volume).

[0121] In certain embodiments, the particulate solid includes at least one of an extender, a reinforcing material, or a functional filler. Extenders (sometimes referred to as fillers) are generally known to be materials that are included primarily to reduce the cost of the composition without adversely affecting its performance because they are generally less expensive than other ingredients of the composition. In certain embodiments, the extender includes at least one of calcium carbonate, talc, barium sulfate, aluminum oxide, or quartz. Suitable extenders include, but are not limited to: wollastonite (including surface-treated wollastonite); calcium sulfate (as its anhydride, dihydrate, or trihydrate); calcium carbonate (including chalk); limestone, marble, and synthetic precipitated calcium carbonate, typically in the form of ground particles, which typically contain 98+% CaCO3, the remainder being other inorganics such as magnesium carbonate, iron oxide, and aluminosilicates; surface-treated calcium carbonate; talc, including fibrous talc, modular talc, acicular talc, and flaky talc. Talc; both hollow and solid glass spheres; and kaolin, including hard kaolin, soft kaolin, calcined kaolin, and kaolin containing various coatings known in the art to promote dispersion in and compatibility with thermosetting resins; mica; feldspar and nepheline syenite; silicate spheres; flue dust; coal spheres; magnesium aluminosilicates; armospheres; natural silica sand; quartz; quartzite; perlite; diatomite; diatomaceous earth; synthetic silica, etc.

[0122] Functional fillers are generally known as materials that are primarily included to provide and / or improve certain properties of the composition, such as fire-resistant / flame-retardant materials and / or pigments. In certain embodiments, the functional filler includes at least one of a flame-retardant material or a pigment. Suitable functional fillers may include, but are not limited to: boron nitride powder and borosilicate powder for obtaining a cured product with a low dielectric constant and a low dielectric loss tangent; or silica powder (such as fused silica and / or crystalline silica), alumina and / or magnesium oxide (or magnesium oxide) for high temperature conductivity.

[0123] In certain embodiments, the extender and / or functional filler may comprise particles having an average aspect ratio of less than about 5:1.

[0124] Reinforcement is generally known as the material mainly included to improve some physical properties (such as tensile strength) of composition.In certain embodiments, reinforcement includes at least one type of fibrous material.As used herein, term "fibrous material" is intended to represent any material, wherein each particle generally has a length (the longest dimension of each particle of material, may be averaged) substantially longer than its width (the shortest dimension of each particle of material, may be averaged), such as a ratio of length to width greater than about 5:1, may be averaged.Suitable fiber may include but is not limited to having high tensile strength (such as greater than 500kpsi (or 3447MPa)) fiber, carbon or graphite fiber, glass fiber and the fiber formed by silicon carbide, aluminum oxide, boron, quartz, etc., and the fiber formed by organic polymer (such as polyolefin, poly (benzothiazole), poly (benzimidazole), polyarylate, poly (benzoxazole), aramid, polyarylether, etc.), and may include a mixture with two or more such fibers. The fibers can be used in the form of discontinuous or continuous tows composed of multiple filaments, as continuous unidirectional or multidirectional tapes, as short-cut loose fibers, or as woven fabrics, non-crimped fabrics or non-woven fabrics. The weaving form can be selected from a plain weave style, a satin weave style or a twill weave style. The non-crimped fabric can have multiple plies and fiber orientations.

[0125] In certain embodiments, the thermosetting resin is present in an amount of 80% to 20% by weight (e.g., 75% to 20% by weight, 70% to 20% by weight, 65% to 20% by weight, 60% to 20% by weight, 55% to 20% by weight, 50% to 20% by weight, 45% to 20% by weight, 40% to 20% by weight, 35% to 20% by weight, 30% to 20% by weight, 25% to 20% by weight, 80% to 25% by weight, 75% to 25% by weight, 70% to 25% by weight, 65% to 25% by weight, 60% to 25% by weight, 55% to 20% by weight, 50% to 20% by weight, 45% to 20% by weight, 40% to 20% by weight, 35% to 20% by weight, 30% to 20% by weight, 25% to 20% by weight, 80% to 25% by weight, 75% to 25% by weight, 70% to 25% by weight, 65% to 25% by weight, 60% to 25% by weight, 55% to 25% by weight, 50% to 25% by weight, 45% to 25% by weight, 40% to 25% by weight, 35% to 25% by weight, 30% to 25% by weight, 80% to 30% by weight, 75% to 30% by weight, 70% to 30% by weight, 65% to 30% by weight, 60% to 30% by weight, 55% to 30% by weight, 50% to 30% by weight, 45% to 30% by weight, 40% to 30% by weight, 35% to 30% by weight, 80% to 35% by weight, 75% to 35% by weight, 70% to 35% by weight, 65% to 35% by weight, 60% to 35% by weight, 55% to 35% by weight %, 50% to 35% by weight, 45% to 35% by weight, 40% to 35% by weight, 80% to 40% by weight, 75% to 40% by weight, 70% to 40% by weight, 65% to 40% by weight, 60% to 40% by weight, 55% to 40% by weight, 50% to 40% by weight, 45% to 40% by weight, 80% to 45% by weight, 75% to 45% by weight, 70% to 45% by weight, 65% to 45% by weight, 60% to 45% by weight, 55% to 45% by weight, 50% to 45% by weight, 80% to 50% by weight, 75% to 50% by weight, 70% to 45% by weight % to 50 wt%, 65 wt% to 50 wt%, 60 wt% to 50 wt%, 55 wt% to 50 wt%, 80 wt% to 50 wt%, 75 wt% to 50 wt%, 70 wt% to 50 wt%, 65 wt% to 50 wt%, 60 wt% to 50 wt%, 80 wt% to 55 wt%, 75 wt% to 55 wt%, 70 wt% to 55 wt%, 65 wt% to 55 wt%, 60 wt% to 55 wt%, 80 wt% to 60 wt%, 75 wt% to 60 wt%, 70 wt% to 60 wt%, 65 wt% to 60 wt%, 80 wt% to 65 wt%, 75 wt% to 65 wt%, 70 wt% to 65 wt%,80 wt % to 70 wt %, 75 wt % to 70 wt %, or 80 wt % to 75 wt %).

[0126] In certain embodiments, thermosetting resins include epoxy resins, unsaturated polyester resins, vinyl ester resins, polyurethane resins or phenolic resins. Suitable thermosetting resins include resins that react chemically and become relatively infusible when heated, catalyzed or subjected to ultraviolet rays, lasers, infrared rays, cations, electron beams or microwave radiation. Exemplary reactions in thermosetting resins include oxidation of unsaturated double bonds, reactions involving epoxy / amine, epoxy / carbonyl, epoxy / hydroxyl, epoxy and Lewis acid or Lewis base, polyisocyanate / hydroxyl, amino resin / hydroxyl moiety, free radical reaction or polyacrylate reaction, cationic polymerization of epoxy and vinyl ether and condensation of silanol. Examples of unsaturated resins include polyester resins prepared by reacting one or more diacids or anhydrides with one or more glycols. This resin is generally provided in the form of a mixture with reactive monomers (such as styrene or vinyl toluene) and is commonly referred to as phthalic resins and isophthalic resins. Other examples include resins that use dicyclopentadiene (DCPD) as co-reactants in polyester chains. Other examples also include the reaction product of bisphenol A diglycidyl ether and unsaturated carboxylic acids such as methacrylic acid, which is then provided in the form of a solution in styrene, commonly referred to as vinyl ester resin. Polymers with hydroxyl functional groups (such as polyols) are widely used in thermosetting systems to crosslink with amino resins or polyisocyanates. Polyols include acrylic polyols, alkyd polyols, polyester polyols, polyether polyols and polyurethane polyols. Exemplary amino resins include melamine formaldehyde resins, benzoguanamine formaldehyde resins, urea formaldehyde resins and glycoluril formaldehyde resins. Polyisocyanates are resins with two or more isocyanate groups, including monomeric aliphatic diisocyanates, monomeric aromatic diisocyanates and polymers thereof. Exemplary aliphatic diisocyanates include hexamethylene diisocyanate, isophorone diisocyanate and hydrogenated diphenylmethane diisocyanate. Exemplary aromatic isocyanates include toluene diisocyanate and diphenylmethane diisocyanate.

[0127] In certain embodiments, the coupling agent is present in an amount of 0.5 wt % to 5 wt %, such as 1 wt % to 5 wt %, 1.5 wt % to 5 wt %, 2 wt % to 5 wt %, 2.5 wt % to 5 wt %, 3 wt % to 5 wt %, 3.5 wt % to 5 wt %, 4 wt % to 5 wt %, 4.5 wt % to 5 wt %, 0.5 wt % to 4.5 wt %, 1 wt % to 4.5 wt %, 1.5 wt % to 4.5 wt %, 2 wt % to 4.5 wt %, 2.5 wt % to 4.5 wt %, 3 wt % to 4.5 wt %, 3.5 wt % to 4.5 wt %, 4 wt % to 4.5 wt %, 0.5 wt % to 4.5 wt %, 1 wt % to 4.5 wt %, 1.5 wt % to 4.5 wt %, 2 %, 3 wt % to 4 wt %, 3.5 wt % to 4 wt %, 0.5 wt % to 3.5 wt %, 1 wt % to 3.5 wt %, 1.5 wt % to 3.5 wt %, 2 wt % to 3.5 wt %, 2.5 wt % to 3.5 wt %, 3 wt % to 3.5 wt %, 0.5 wt % to 3 wt %, 1 wt % to 3 wt %, 1.5 wt % to 3 wt %, 2 wt % to 3 wt %, 2.5 wt % to 3 wt %, 0.5 wt % to 2.5 wt %, 1 wt % to 2.5 wt %, 1.5 wt % to 2.5 wt %, 2 wt % to 2.5 wt %, 0.5 wt % to 2 wt %, 1 wt % to 2 wt %, 1.5 wt % to 2 wt %, 0.5 wt % to 1.5 wt %, 1 wt % to 1.5, or 0.5 wt % to 1 wt %).

[0128] In certain embodiments, the monomer units a according to formula I may be derived from free radical polymerization of aromatic or aliphatic vinyl monomers, such as aromatic vinyls, such as styrene and / or substituted styrenes, for example 4-acetoxystyrene, 4-benzhydrylstyrene, 4-benzyloxy-3-methoxystyrene, 2-bromostyrene, 3-bromostyrene, 4-bromostyrene, 4-tert-butoxystyrene, 4-tert-butylstyrene, 2-chlorostyrene, 3-chlorostyrene, 4-chlorostyrene, 2,6-dichlorostyrene, 2,6-difluorostyrene, 3-bromostyrene, 4-tert-butylstyrene, , 4-dimethoxystyrene, 2,4-dimethylstyrene, 2,5-dimethylstyrene, N,N-dimethylvinylbenzylamine, 4-ethoxystyrene, 2-fluorostyrene, 3-fluorostyrene, 4-fluorostyrene, 3-methylstyrene, 4-methylstyrene, 3-nitrostyrene, 2,3,4,5,6-pentafluorostyrene, 3-(trifluoromethyl)styrene, 4-(trifluoromethyl)styrene, 2,4,6-trimethylstyrene, 4-vinylanisole, 3-vinylbenzoic acid, 4-vinylbenzoic acid, 4-vinylbenzyl chloride, 4-vinylbiphenyl, 2-vinylnaphthalene. In certain embodiments, R 2 Can be C1 to C 20 In certain embodiments, R 2 Can be C6 to C 10 Aryl group.

[0129] In certain embodiments, monomer units b according to formula I may be derived from free radical polymerization of vinyl anhydride monomers, such as maleic anhydride or itaconic anhydride.

[0130] In certain embodiments, monomer unit c according to formula I may be derived from the free radical polymerization of a vinyl anhydride monomer (such as maleic anhydride or itaconic anhydride) reacted with an amino-functional vinyl monomer (such as a vinyl ether) or a (meth)acrylate (such as 2-(2-propen-1-yloxy)-ethylamine or 2-aminoethylmethacrylate hydrochloride).

[0131] In certain embodiments, monomer unit d according to formula I may be derived from the free radical polymerization of a vinyl anhydride monomer such as maleic anhydride or itaconic anhydride reacted with a hydroxyl-functional vinyl ether or (meth)acrylate such as 2-allyloxyethanol, allyl alcohol, 1,4-butanediol vinyl ether, di(ethylene glycol) vinyl ether, poly(ethylene glycol) vinyl ether, diethylene glycol monoallyl ether, 3-allyloxy-1,2-propylene glycol, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 4-hydroxybutyl acrylate, 6-hydroxyhexyl methacrylate, poly(ethylene glycol) methacrylate, poly(ethylene glycol) acrylate, poly(propylene glycol) methacrylate, poly(propylene glycol) acrylate, or 2,3-dihydroxypropyl methacrylate.

[0132] In certain embodiments, monomer unit e according to formula I may be derived from 1 In certain embodiments, POL 1 It can be a hydroxyl functional polyether chain, such as polyethylene glycol methyl ether or polypropylene glycol methyl ether. 1 It may be an amino-functional polyether, for example, L100, L207, L300, B100 and / or B200 are polyetheramines commercially available from Huntsman.

[0133] In certain embodiments, monomer unit f according to formula I may be derived from POL via an amine bond or a hydroxyl bond. 2 In certain embodiments, POL 2 It can be a hydroxyl functional polyether chain, such as polyethylene glycol methyl ether or polypropylene glycol methyl ether. 2 It may be an amino-functional polyether, for example, L100, L207, L300, B100 and / or B200 are polyetheramines commercially available from Huntsman.

[0134] In certain embodiments, Z 1 and / or Z 2Each of which is independently oxygen, wherein the monohydroxy functional polyester has been reacted with anhydride monomers. The monohydroxy functional polyester can be synthesized by any method known to those skilled in the art by polymerization of lactones and / or lactides and / or hydroxy carboxylic acids, optionally in the presence of monohydric alcohols, to initiate polyester chain extension. Useful alcohols include, but are not limited to, methanol, ethanol, n-propanol, n-butanol, neopentyl alcohol, n-hexanol, n-heptanol, n-octanol, n-decanol, n-dodecanol, n-tetradecanol, n-hexadecanol, oleyl alcohol, n-octadecanol, isopropanol, isobutanol, tert-butanol, 2-ethylbutanol, 2-ethylhexanol, 3-heptanol, 3,5,5-trimethylhexanol, 3,7-dimethyloctanol, cyclohexanol, cyclopentanol, cyclopentanemethanol, cyclohexylmethanol, 4-cyclohexyl-1-butanol, 4-ethylcyclohexanol, cycloheptanol, phenol, o-cresol, 2-ethylphenol, 2-propylphenol, 4-ethylphenol, octylphenol, nonylphenol, dodecanol ... Alkylphenols, di- and tri-phenylenediol, benzyl alcohol, 2-phenylethanol, 1-naphthol, 2-naphthol, 2-phenylphenol, 4-phenylphenol, polyisobutylenephenol, secondary phenylethanol, 4-ethylbenzyl alcohol, 4-butylbenzyl alcohol, 2-naphthyl alcohol, 3-phenyl-1-propanol, 4-phenyl-1-butanol, cinnamyl alcohol and 4-propoxyphenol, 2-dimethylaminoethanol, 2-diethylaminoethanol, 2-dibutylaminoethanol, 2-propen-1-ol, allyl alcohol, 4-penten-1-ol, 2-hexen-1-ol, 3-nonen-1-ol, 7-dodecen-1-ol, the phenols sold under the trade name Unilin TM Saturated straight chain alcohols and saturated branched chain alcohols commercially available from Baker Hughes, such as "Guerbet" alcohols commercially available from Sasol GmbH under the trade name Isofol, including mixtures thereof. Specific examples of commercially available Guerbet alcohols are Isofol 12, 14T, 16, 18T, 18E, 20, 24, 28, 32, 32T and 36.

[0135] In certain embodiments, the coupling agent comprises at least 90 wt % (such as at least 91 wt %, at least 92 wt %, at least 93 wt %, at least 94 wt %, at least 95 wt %, at least 96 wt %, at least 97 wt %, at least 98 wt %, or at least 99 wt %) of monomeric units a, b, c, d, e, and f according to Formula I, based on the total weight of the coupling agent. In certain embodiments, the coupling agent comprises 90 wt % to 100 wt % (such as 91 wt % to 100 wt %, 92 wt % to 100 wt %, 93 wt % to 100 wt %, 94 wt % to 100 wt %, 95 wt % to 100 wt %, 96 wt % to 100 wt %, 97 wt % to 100 wt %, 98 wt % to 100 wt %, 99 wt % to 100 wt %, 90 wt % to 99 wt %, 91 wt % to 99 wt % %, 92% to 99% by weight, 93% to 99% by weight, 94% to 99% by weight, 95% to 99% by weight, 96% to 99% by weight, 97% to 99% by weight, 98% to 99% by weight, 90% to 98% by weight, 91% to 98% by weight, 92% to 98% by weight, 93% to 98% by weight, 94% to 98% by weight, 95% to 98% by weight, 96% to 98% by weight, 97% to 98% by weight %, 90% to 97% by weight, 91% to 97% by weight, 92% to 97% by weight, 93% to 97% by weight, 94% to 97% by weight, 95% to 97% by weight, 96% to 97% by weight, 90% to 96% by weight, 91% to 96% by weight, 92% to 96% by weight, 93% to 96% by weight, 94% to 96% by weight, 95% to 96% by weight, 90% to 95% by weight, 91% to 95% by weight, % to 93 wt %, 90 wt % to 92 wt %, 91 wt % to 92 wt %, 92 wt % to 95 wt %, 93 wt % to 95 wt %, 94 wt % to 95 wt %, 90 wt % to 94 wt %, 91 wt % to 94 wt %, 92 wt % to 94 wt %, 93 wt % to 94 wt %, 90 wt % to 93 wt %, 91 wt % to 93 wt %, 92 wt % to 93 wt %, 90 wt % to 92 wt %, 91 wt % to 92 wt % or 90 wt % to 91 wt % of the monomer units a, b, c, d, e and f according to formula I

[0136] In certain embodiments, the coupling agent comprises at least 70 wt %, such as at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, or at least 95 wt %, of monomeric units a and b according to Formula I, based on the total weight of the coupling agent. In certain embodiments, the coupling agent comprises 70 to 95 wt %, such as 75 to 95 wt %, 80 to 95 wt %, 85 to 95 wt %, 90 to 95 wt %, 70 to 90 wt %, 75 to 90 wt %, 80 to 90 wt %, 85 to 90 wt %, 70 to 85 wt %, 75 to 85 wt %, 80 to 85 wt %, 70 to 80 wt %, 75 to 80 wt %, or 70 to 75 wt % of monomeric units a and b according to Formula I, based on the total weight of the coupling agent.

[0137] In certain embodiments, the coupling agent comprises no more than 30 wt % (such as no more than 25 wt %, no more than 20 wt %, no more than 15 wt %, no more than 10 wt %, or no more than 5 wt %) of monomeric units c, d, e, and f according to Formula I, based on the total weight of the coupling agent. In certain embodiments, the coupling agent comprises 5 to 30 wt % (such as 10 to 30 wt %, 15 to 30 wt %, 20 to 30 wt %, 25 to 30 wt %, 5 to 25 wt %, 10 to 25 wt %, 15 to 25 wt %, 20 to 25 wt %, 5 to 20 wt %, 10 to 20 wt %, 15 to 20 wt %, 5 to 15 wt %, 10 to 15 wt %, or 5 to 10 wt %) of monomeric units c, d, e, and f according to Formula I, based on the total weight of the coupling agent.

[0138] In certain embodiments, the coupling agent comprises at least 50 wt % (such as at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt % or at least 80 wt %) of monomer units a according to formula I, based on the total weight of the coupling agent. In certain embodiments, the coupling agent comprises 50 to 80 wt % (such as 55 to 80 wt %, 60 to 80 wt %, 65 to 80 wt %, 70 to 80 wt %, 75 to 80 wt %, 50 to 75 wt %, 55 to 75 wt %, 60 to 75 wt %, 65 to 75 wt %, 70 to 75 wt %, 50 to 70 wt %, 55 to 70 wt %, 60 to 70 wt %, 65 to 70 wt %, 50 to 65 wt %, 55 to 65 wt %, 60 to 65 wt %, 50 to 60 wt %, 55 to 60 wt %, or 50 to 55 wt %) of monomeric units a according to Formula I, based on the total weight of the coupling agent.

[0139] In certain embodiments, the coupling agent comprises no more than 40 wt % (such as no more than 35 wt %, no more than 30 wt %, no more than 25 wt %, no more than 20 wt %, no more than 15 wt %, no more than 10 wt %, or no more than 5 wt %) of monomeric units b according to Formula I, based on the total weight of the coupling agent. In certain embodiments, the coupling agent comprises 5 wt % to 40 wt % (such as 10 wt % to 40 wt %, 15 wt % to 40 wt %, 20 wt % to 40 wt %, 25 wt % to 40 wt %, 30 wt % to 40 wt %, 35 wt % to 40 wt %, 5 wt % to 35 wt %, 10 wt % to 35 wt %, 15 wt % to 35 wt %, 20 wt % to 35 wt %, 25 wt % to 35 wt %, 30 wt % to 35 wt %, 5 wt % to 35 wt % % to 30 wt %, 10 wt % to 30 wt %, 15 wt % to 30 wt %, 20 wt % to 30 wt %, 25 wt % to 30 wt %, 5 wt % to 25 wt %, 10 wt % to 25 wt %, 15 wt % to 25 wt %, 20 wt % to 25 wt %, 5 wt % to 20 wt %, 10 wt % to 20 wt %, 15 wt % to 20 wt %, 5 wt % to 15 wt %, 10 wt % to 15 wt % or 5 wt % to 10 wt % of monomer units b according to formula I.

[0140] In certain embodiments, a is an integer from 5 to 500, such as from 10 to 500, 15 to 500, 20 to 500, 25 to 500, 50 to 500, 75 to 500, 100 to 500, 150 to 500, 200 to 500, 250 to 500, 300 to 500, 350 to 500, 400 to 500, 450 to 500, 1 to 450, 5 to 450, 10 to 450, 15 to 450, 20 to 450, 25 to 450, 50 to 450, 75 to 450, 100 to 450, 150 to 450, 200 to 450, 250 to 450, 300 to 450, 350 to 450, 400 to 500, 450, 1 to 400, 5 to 400, 10 to 400, 15 to 400, 20 to 400, 25 to 400, 50 to 400, 75 to 400, 100 to 400, 150 to 400, 200 to 400, 250 to 400, 300 to 400, 350 to 400, 1 to 250, 5 to 350, 10 to 350, 15 to 350, 20 to 350, 25 to 350, 50 to 350, 75 to 350, 100 to 350, 150 to 350, 200 to 350, 250 to 350, 300 to 350, 1 to 300, 5 to 300, 10 to 300, 15 to 300, 20 to 300, 25 to 300, 50 to 300, 75 to 300, 100 to 300, 150 to 300, 200 to 300, 250 to 300, 1 to 250, 5 to 250, 10 to 250, 15 to 250, 20 to 250, 25 to 250, 50 to 250, 75 to 250, 100 to 250, 150 to 250, 200 to 250, 1 to 200, 5 to 200, 10 to 200, 15 to 200, 20 to 200, 25 to 200, 50 to 200, 75 to 200, 100 to 200, 150 to 200, 1 to 150, 5 to 150, 10 to 150, 15 to 150, 20 to 150, 25 or 1 to 50, 50 to 150, 75 to 150, 100 to 150, 1 to 100, 5 to 100, 10 to 100, 15 to 100, 20 to 100, 25 to 100, 50 to 100, 75 to 100, 1 to 75, 5 to 75, 10 to 75, 15 to 75, 20 to 75, 25 to 75, 50 to 75, 1 to 50, 5 to 50, 10 to 50, 15 to 50, 20 to 50, 25 to 50, 1 to 25, 5 to 25, 10 to 25, 15 to 25, 20 to 25, 1 to 20, 5 to 20, 10 to 20, 15 to 20, 1 to 15, 5 to 15, 10 to 15, 1 to 10, 5 to 10, or 1 to 5.

[0141] In certain embodiments, b is an integer from 5 to 500, such as from 10 to 500, 15 to 500, 20 to 500, 25 to 500, 50 to 500, 75 to 500, 100 to 500, 150 to 500, 200 to 500, 250 to 500, 300 to 500, 350 to 500, 400 to 500, 450 to 500, 1 to 450, 5 to 450, 10 to 450, 15 to 450, 20 to 450, 25 to 450, 50 to 450, 75 to 450, 100 to 450, 150 to 450, 200 to 450, 250 to 450, 300 to 450, 350 to 450, 400 to 500, 450, 1 to 400, 5 to 400, 10 to 400, 15 to 400, 20 to 400, 25 to 400, 50 to 400, 75 to 400, 100 to 400, 150 to 400, 200 to 400, 250 to 400, 300 to 400, 350 to 400, 1 to 250, 5 to 350, 10 to 350, 15 to 350, 20 to 350, 25 to 350, 50 to 350, 75 to 350, 100 to 350, 150 to 350, 200 to 350, 250 to 350, 300 to 350, 1 to 300, 5 to 300, 10 to 300, 15 to 300, 20 to 300, 25 to 300, 50 to 300, 75 to 300, 100 to 300, 150 to 300, 200 to 300, 250 to 300, 1 to 250, 5 to 250, 10 to 250, 15 to 250, 20 to 250, 25 to 250, 50 to 250, 75 to 250, 100 to 250, 150 to 250, 200 to 250, 1 to 200, 5 to 200, 10 to 200, 15 to 200, 20 to 200, 25 to 200, 50 to 200, 75 to 200, 100 to 200, 150 to 200, 1 to 150, 5 to 150, 10 to 150, 15 to 150, 20 to 150, 25 or 1 to 50, 50 to 150, 75 to 150, 100 to 150, 1 to 100, 5 to 100, 10 to 100, 15 to 100, 20 to 100, 25 to 100, 50 to 100, 75 to 100, 1 to 75, 5 to 75, 10 to 75, 15 to 75, 20 to 75, 25 to 75, 50 to 75, 1 to 50, 5 to 50, 10 to 50, 15 to 50, 20 to 50, 25 to 50, 1 to 25, 5 to 25, 10 to 25, 15 to 25, 20 to 25, 1 to 20, 5 to 20, 10 to 20, 15 to 20, 1 to 15, 5 to 15, 10 to 15, 1 to 10, 5 to 10, or 1 to 5.

[0142] In certain embodiments, the ratio of a to b is 1:1 to 10:1, 1:1 to 9:1, 1:1 to 8:1, 1:1 to 7:1, 1:1 to 6:1, 1:1 to 5:1, 1:1 to 4:1, 1:1 to 3:1, 1:1 to 2:1, 2:1 to 10:1, 2:1 to 9:1, 2:1 to 8:1, 2:1 to 7:1, 2:1 to 6:1, 2:1 to 5:1, 2:1 to 4:1, 2:1 to 3:1, 3:1 to 10:1, 3:1 to 9:1, 3:1 to 8:1, 3:1 to 7:1, 3:1 to 6:1. :1, 3:1 to 5:1, 3:1 to 4:1, 4:1 to 10:1, 4:1 to 9:1, 4:1 to 8:1, 4:1 to 7:1, 4:1 to 6:1, 4:1 to 5:1, 5:1 to 10:1, 5:1 to 9:1, 5:1 to 8:1, 5:1 to 7:1, 5:1 to 6:1, 6:1 to 10:1, 6:1 to 9:1, 6:1 to 8:1, 6:1 to 7:1, 7:1 to 10:1, 7:1 to 9:1, 7:1 to 8:1, 8:1 to 10:1, 8:1 to 9:1, or 9:1 to 10:1.

[0143] In certain embodiments, c is 1 to 100, 5 to 100, 10 to 100, 15 to 100, 20 to 100, 30 to 100, 40 to 100, 50 to 100, 60 to 100, 70 to 100, 80 to 100, 90 to 100, 1 to 90, 5 to 90, 10 to 90, 15 to 90, 20 to 90, 30 to 90, 40 to 90, 50 to 90, 60 to 90, 70 to 90, 80 to 90, 1 to 80, 5 to 80, 10 to 80, 15 to 80, 20 to 80, 30 to 80, 40 to 80, 50 to 80, 60 to 80, 70 to 80, 1 to 70, 5 to 70, 10 to 70, 15 to 70. 5 to 10, 15 to 10, 20 to 30, 30 to 30, 40 to 30, 50 to 10, 20 to 30, 10 to 30, 15 to 30, 20 to 30, 1 to 20, 5 to 20, 10 to 20, 15 to 20, 1 to 15, 5 to 15, 10 to 15, 1 to 10, 5 to 10, or an integer from 0 to 5.

[0144] In certain embodiments, d is from 1 to 100, 5 to 100, 10 to 100, 15 to 100, 20 to 100, 30 to 100, 40 to 100, 50 to 100, 60 to 100, 70 to 100, 80 to 100, 90 to 100, 1 to 90, 5 to 90, 10 to 90, 15 to 90, 20 to 90, 30 to 90, 40 to 90, 50 to 90, 60 to 90, 70 to 90, 80 to 90, 1 to 80, 5 to 80, 10 to 80, 15 to 80, 20 to 80, 30 to 80, 40 to 80, 50 to 80, 60 to 80, 70 to 80, 1 to 70, 5 to 70, 10 to 70, 15 to 70. 5 to 10, 15 to 10, 20 to 30, 30 to 30, 40 to 30, 50 to 10, 20 to 30, 10 to 30, 15 to 30, 20 to 30, 1 to 20, 5 to 20, 10 to 20, 15 to 20, 1 to 15, 5 to 15, 10 to 15, 1 to 10, 5 to 10, or an integer from 0 to 5.

[0145] In certain embodiments, e is 1 to 100, 5 to 100, 10 to 100, 15 to 100, 20 to 100, 30 to 100, 40 to 100, 50 to 100, 60 to 100, 70 to 100, 80 to 100, 90 to 100, 1 to 90, 5 to 90, 10 to 90, 15 to 90, 20 to 90, 30 to 90, 40 to 90, 50 to 90, 60 to 90, 70 to 90, 80 to 90, 1 to 80, 5 to 80, 10 to 80, 15 to 80, 20 to 80, 30 to 80, 40 to 80, 50 to 80, 60 to 80, 70 to 80, 1 to 70, 5 to 70, 10 to 70, 15 to 70, 5 to 10, 15 to 10, 20 to 30, 30 to 30, 40 to 30, 50 to 10, 20 to 30, 10 to 30, 15 to 30, 20 to 30, 1 to 20, 5 to 20, 10 to 20, 15 to 20, 1 to 15, 5 to 15, 10 to 15, 1 to 10, 5 to 10, or an integer from 0 to 5.

[0146] In certain embodiments, f is from 1 to 100, 5 to 100, 10 to 100, 15 to 100, 20 to 100, 30 to 100, 40 to 100, 50 to 100, 60 to 100, 70 to 100, 80 to 100, 90 to 100, 1 to 90, 5 to 90, 10 to 90, 15 to 90, 20 to 90, 30 to 90, 40 to 90, 50 to 90, 60 to 90, 70 to 90, 80 to 90, 1 to 80, 5 to 80, 10 to 80, 15 to 80, 20 to 80, 30 to 80, 40 to 80, 50 to 80, 60 to 80, 70 to 80, 1 to 70, 5 to 70, 10 to 70, 15 to 70. 5 to 10, 15 to 10, 20 to 30, 30 to 30, 40 to 30, 50 to 10, 20 to 30, 10 to 30, 15 to 30, 20 to 30, 1 to 20, 5 to 20, 10 to 20, 15 to 20, 1 to 15, 5 to 15, 10 to 15, 1 to 10, 5 to 10, or an integer from 0 to 5.

[0147] In certain embodiments, the coupling agent comprises up to 10 wt. % (such as up to 9 wt. %, up to 8 wt. %, up to 7 wt. %, up to 6 wt. %, up to 5 wt. %, up to 4 wt. %, up to 3 wt. %, up to 2 wt. % or up to 1 wt. %) of other monomeric units different from monomeric units a, b, c, d, e and f according to formula I. In certain embodiments, the coupling agent comprises greater than 0% to 10% by weight (such as greater than 0% to 9% by weight, greater than 0% to 7% by weight, greater than 0% to 6% by weight, greater than 0% to 5% by weight, greater than 0% to 4% by weight, greater than 0% to 3% by weight, greater than 0% to 2% by weight, greater than 0% to 1% by weight, 1% to 10% by weight, 1% to 9% by weight, 1% to 8% by weight, 1% to 7% by weight, 1% to 6% by weight, 1% to 5% by weight, 1% to 4% by weight, 1% to 3% by weight, 1% to 2% by weight, 2% to 10% by weight, 2% to 9% by weight, 2% to 8% by weight, 2% to 7% by weight, 2% to 6% by weight, 2% to 5% by weight, 2% to 4% by weight, 2% to 3% by weight, 3% to 10% by weight %, 3 wt% to 9 wt%, 3 wt% to 8 wt%, 3 wt% to 7 wt%, 3 wt% to 6 wt%, 3 wt% to 5 wt%, 3 wt% to 4 wt%, 4 wt% to 10 wt%, 4 wt% to 9 wt%, 4 wt% to 8 wt%, 4 wt% to 7 wt%, 4 wt% to 6 wt%, 4 wt% to 5 wt%, 5 wt% to 10 wt%, 5 wt% to 9 wt%, 5 wt% to 8 wt% %, 5 wt % to 7 wt %, 5 wt % to 6 wt %, 6 wt % to 10 wt %, 6 wt % to 9 wt %, 6 wt % to 8 wt %, 6 wt % to 7 wt %, 7 wt % to 10 wt %, 7 wt % to 9 wt %, 7 wt % to 8 wt %, 8 wt % to 10 wt %, 8 wt % to 9 wt % or 9 wt % to 10) of other monomeric units different from monomeric units a, b, c, d, e and f according to formula I. In certain embodiments, coupling agent is substantially free of or does not contain other monomeric units different from monomeric units a, b, c, d, e and f according to formula I. In this context, "substantially free of" means that other monomeric units are not intentionally added or produced, but they may exist by including impurities in reactants and / or by producing unexpected reaction products. In certain embodiments, other monomeric units are vinyl functional monomeric units.

[0148] A method for making the thermosetting composition described herein is also provided, the method comprising dissolving a coupling agent in a thermosetting resin with or without a solvent, and then adding particulate solids and other additives. Other additives may include at least one of a dispersant, a defoamer, an internal release agent, an accelerator, and the like.

[0149] Also provided is a method for making the thermosetting composition described herein, the method comprising dispersing the coupling agent as a dry solid into the thermosetting resin, and then adding the particulate solid and other additives. The other additives may include at least one of a dispersant, a defoamer, an internal release agent, an accelerator, and the like.

[0150] Also provided is a method of imparting high / improved tensile strength to the thermosetting compositions described herein, the method comprising dispersing a particulate solid in a thermosetting resin in the presence of a coupling agent.

[0151] Also provided is a method of imparting flame retardancy to a thermosetting composition as described herein, the method comprising dispersing a particulate solid (which imparts flame retardancy) into a thermosetting resin in the presence of a coupling agent.

[0152] Also provided is a method of lightening the thermosetting composition described herein, the method comprising dispersing hollow particles (glass spheres) and fillers (as particulate solids) in a thermosetting resin in the presence of a coupling agent.

[0153] Also provided is a method of making the thermosetting composition described herein, the method comprising treating a particulate solid with a coupling agent to form a treated particulate solid, and then adding the treated particulate solid to a thermosetting resin. For example, the fiber material may be pretreated with an adhesive that also acts as a coupling agent.

[0154] The subject matter disclosed herein can be better understood with reference to the following examples, which are only used to further illustrate the subject matter disclosed herein. The exemplary embodiments should not be interpreted as limiting the subject matter in any way.

[0155] Example 1: Polystyrene-co-polymaleic anhydride copolymer (2:1 molar ratio styrene:maleic anhydride, 20 parts) was dissolved in ethyl acetate (79.69 parts) at 70°C under nitrogen. Polyetheramine (56.90 parts) was added and the reaction was stirred for 2 hours until the consumption of the amine was confirmed by titration. The temperature was then raised to 100°C for 3 hours to remove the solvent. The nitrogen seal was removed, 2-hydroxyethyl methacrylate (2.55 parts) and 2,6-di-tert-butyl-4-methylphenol (0.24 parts) were added, and the reaction was heated to 120°C under air for 5 hours. An amber liquid was obtained.

[0156] Example 1 was incorporated into an unsaturated polyester resin (available from AOC AG) P17-02) in a dispersion containing calcium carbonate and recycled carbon fiber. The formulation included a peroxide curing catalyst (tert-butyl peroxybenzoate purchased from Sigma Aldrich). Example 2 and Example 3 include the parts of each component as shown in Table 1 below. The tensile strength of each of Example 2 and Example 3 was measured by an Instron tensile strength tester and is recorded in Table 1.

[0157] Table 1

[0158] Example 2 Example 3 Unsaturated polyester resin 50 50 Calcium carbonate 125 125 Carbon Fiber 15 15 Curing catalyst 0.8 0.8 Example 1 2.6 Tensile strength(MPa) 23.9 36.7

[0159] Example 4: Poly(isobutylene-alt-maleic anhydride) (average M W =6000, 15.34 parts) was suspended in water (93 parts) at 70°C under nitrogen. A polyetheramine (available from Huntsman) was added. L207, 69.07 parts) and the reaction was stirred for 1 hour. The temperature was raised to >100°C to remove water over 4 hours. The nitrogen seal was removed, 2-hydroxyethyl methacrylate (4.45 parts) and 2,6-di-tert-butyl-4-methylphenol (0.29 parts) were added, and the reaction was heated at 95°C for 8 hours. An amber liquid was obtained, and its molecular weight was determined by GPC in tetrahydrofuran doped with 1% acetic acid relative to polystyrene standards (Mn=2623, Mw=11212).

[0160] The following tests were conducted to determine the suitability of the embodiments described herein for various applications in which fiber and / or filler reinforced thermosets may be used. These formulation examples and the illustrative typical applications indicated are not intended to be limiting but rather to highlight the variety of potential complex resin filler / fiber interfaces present in composite materials where reactive coupling agents of the type described herein may be beneficial. It is known that "coupling" of filler / fiber surfaces with bulk resin at a molecular level during curing produces beneficial mechanical property improvements in the resulting macroscopic composite parts or articles containing these interfaces.

[0161] The benefits observed in the measurement of such mechanical properties and the modes selected for studying such improvements are highly dependent on the isotropy of the composite material, which is a result of the alignment of fillers and fibers within the resin matrix relative to the forces experienced. Therefore, the stresses and strains generated during different mechanical test modes are transmitted to different degrees at the existing resin-filler / fiber interfaces, depending on the relative orientation of these interfaces to the forces applied in the specific test mode. Therefore, depending on the formulation; filler / fiber alignment and positioning; forming and manufacturing techniques used to produce the tested composite articles; the benefits of the coupling agents of the subject matter of the present invention may or may not be observed in a series of standardized mechanical tests. There are many suitable tests (or modifications thereof) for evaluating mechanical improvements in composite articles, but they are not exhaustively summarized in ASTM D4762-18; it is expected that any of these tests can be used to determine the effectiveness of the subject matter of the present invention in a specific material and / or for a specific use of the resulting material. Therefore, when used appropriately by a person skilled in the art, any of these tests listed can be used to demonstrate the benefits exemplified herein. Therefore, the benefits observed in the more basic and dynamic tests used and described can be converted into benefits in appropriately selected higher-order, static or dynamic, mechanical tests.

[0162] The testing of Examples 5 and 6 was conducted with milled fibers instead of other fiber forms to reduce anisotropy in the composites formed during the exemplified testing, thereby limiting the complexity of the measurements that may be caused by anisotropy of other fiber forms. The mechanical benefit of "coupling" at the resin-filler / fiber interface is more clearly explained from other reinforcement and stiffening effects in this basic test type and comparison of the moduli measured. Therefore, the observed benefits will translate to benefits observable with more standardized and mode-specific testing, suitable for more anisotropic materials derived from higher order fiber / filler forms and arrangements, where the test mode is appropriately selected to probe the coupling at the interface under consideration, as listed non-exhaustively in ASTM D4762-18.

[0163] Other basic test methods that may show similar convertible observations with other mechanical modes may focus on observing the benefits at a single isolated interface of interest, orienting that interface into the desired plane relative to the stress and strain of the mechanical mode used, and measuring the modulus or stress at which that interface fails in isolation. This type of test method measuring interfacial shear strength (IFSS) may also be used to demonstrate the benefits of the subject coupling agents, an example of such a test that may be applied to thermoset research is described in Interface strength in glass fibre-polypropylene measured using the fibre pull-out and microbond methods, L. Yang and JL Thomason, 2010, Composites Part A: Applied Science and Manufacturing, Vol 41, issue 9 p1077-1083.

[0164] The formation and solidification of composite products may need to be carried out under a series of conditions depending on the manufacturing technology and the chemical composition of the resin formulation adopted. Usually, in addition to curing agent, initiator or catalyst, other chemical additives (such as promoter, accelerator or inhibitor) can also be used in the preparation, select these chemical additives to adapt to the resin chemistry and enable to cure thermosetting materials under the required conditions of processing, forming and manufacturing composite products. Determining whether additional additives (such as the coupling agent of the subject of the present invention) affect the curing kinetics of whole composite formulation is important for understanding these reagents for the application of interest and the suitability of preparation. Therefore, the "full cure" test adopted in the following examples allows to compare the curing time under the situation of the exemplary additive of the subject of the present invention with and without. It is desirable that the change of curing kinetics is seldom or not.

[0165] Generally, the described formulations were tested in a single frequency oscillation "through cure" experiment of the type described by Tianhong T. Chen et al. (Characterising thermoset curing using rheology; SAMPE Conference proceedings 2019, Society for the advancement of Material and Process Engineering). Additional guidance using ASTM D4065 20 Standard Practice for Plastics: Dynamic Mechanical Properties: Determination and report Procedures was used.

[0166] The DHR-1 rheometer (TAInstruments) equipped with 25mm disposable aluminum parallel plates is used together with the ETC attachment. All tests involve subjecting the sample of the uncured formulation of the set volume (determined by the initial geometric gap) to torsional oscillations by the temperature characteristic diagram at a frequency of 1Hz, which cures the formulation of interest and is suitable for applications of interest. Active control is used in both strain and axial force during the test to enable monitoring of the curing process while remaining within the linear viscoelastic limit of the material. Axial force adjustment is used throughout the run, and the axial force is actively controlled to 0.0 ± 0.1N in compression mode, and automatic strain adjustment is used as described in the reference program. However, certain parameters are adjusted in the test for different recipes to better suit the possible manufacturing conditions for each embodiment group, and after describing the recipe description of the embodiment in detail, these parameters are described in detail as follows for each example.

[0167] The analytical calculations performed in the instrument-supported Trios software were derived from the measurements of the individual experiments. The onset "gel" temperature of cure was calculated from the storage modulus cure relative to temperature (d(Log(G')) / dT). The storage modulus in the isothermal post-cure plateau was calculated by correcting for differences between experiments for different samples by regression correlation in this region ( b ) to adhere to the principle of equivalent sample size specified in ASTM D4065 20, but applied in this experimental context of torsion between parallel plates. The measurements obtained through the full cure experiments were used to screen the exemplary coupling agents to determine their suitability in the exemplary formulations and inferred applications.

[0168] Example 8 was incorporated into aluminum hydroxide (Martinal TM OL104) and milled glass fiber (1320K from Owens Corning) in a liquid epoxy resin (Epikote TM 827). The formulation includes a dicyandiamide curing agent (available from Evonik CG1400F) and imidazole curing accelerator (purchased from Evonik Table 2 details the weight % of each component in the tested formulations for Examples 5 and 6.

[0169] Table 2

[0170] Example 5 Example 6 Example 4 0.8 Epikote 827 37.3 37.0 Amicure CG1400F 3.9 3.9 Curezol 2MZ Azine 2.6 2.5 ATH(Martinal OL104) 37.5 37.2 Milled Glass Fiber(1320K) 18.7 18.6

[0171] Examples 9 and 10 are representative of flame retardant formulations commonly used in GFRP compression molded electrical accessories.

[0172] For Examples 5 and 6, a temperature ramp from 25°C to 135°C at 5°C / min was used. After the sample was cured, it was held at 135°C for 10 minutes to continue the measurement. The initial gap size was 1000μm and the fine adjustment was 50μm, giving a minimum sample volume of 0.49087m at the beginning of the test. The gap temperature compensation-expansion coefficient was 2.7398μm / °C, the compliance was 2.02mrad / Nm, the stress constant was 325949Pa / Nm, the strain constant was 12.51 / rad, and the normal stress constant was 4074.37Pa / N. However, the geometric inertia and friction were calibrated for each run. The variable operating parameters for Examples 5 and 6 are summarized in Table 3 below.

[0173] Table 3

[0174] additive <![CDATA[Geometric inertia (μN.m.s 2 )]]> Friction (μN.m / (rad / s)) Example 5 blank 2.34254 0.278571 Example 6 Example 4 2.39741 0.275064

[0175] The measurement results of Example 5 and Example 6 are detailed in Table 4.

[0176] Table 4

[0177] additive Storage modulus platform (Mpa) Initial "gel" temperature (℃) Example 5 blank 14.5 125.5 Example 6 Example 4 17.2 127.8

[0178] Unless otherwise expressly indicated or required by the background in the examples or otherwise, all numerical values ​​of the amount of substance, reaction conditions, molecular weight, number of carbon atoms, etc. specified in this specification should be understood to be modified by the word "about". As used herein, the term "about" means that the value of a given amount is within ± 20% of the specified value. In other embodiments, the value is within ± 15% of the specified value. In other embodiments, the value is within ± 10% of the specified value. In other embodiments, the value is within ± 5% of the specified value. In other embodiments, the value is within ± 2.5% of the specified value. In other embodiments, the value is within ± 1% of the specified value. In other embodiments, the value is within the range of the clearly described values ​​that will be understood by those of ordinary skill in the art based on the disclosure provided herein, with a composition substantially similar to the literal amount described herein.

[0179] It should be understood that the upper and lower limits of the amounts, ranges, and ratios described herein can be independently combined, and any amount within the disclosed range is considered to provide a minimum or maximum value of a narrower range in an alternative embodiment (of course, the minimum amount of the range must be lower than the maximum amount of the same range). Similarly, the ranges and amounts of each element of the subject matter disclosed herein can be used together with the ranges or amounts of any other element.

[0180] While certain representative embodiments and details have been shown for the purpose of illustrating the subject matter disclosed herein, it will be apparent to those skilled in the art that various changes and modifications may be made therein without departing from the scope of the subject matter. In this regard, the scope of the present invention is limited solely by the following claims.

Claims

1. A thermosetting composition comprising a dispersion obtained by dispersing a particulate solid in a thermosetting resin in the presence of a coupling agent, the coupling agent comprising monomer units a, b, c, d, e and f according to formula I: wherein for each molecule of the polymer independently: R 1 is H or CH3; R 2 H, C1-C 20 Alkyl groups, C6-C 10 Aryl group, C7-C 14 an alkylaryl group or a C4-C6 cycloalkyl group; X 1 is 2 or 3 carbon atoms, where if X 1 is 3 carbon atoms, one of the carbon atoms is not included in the polymer backbone; X 2 is 2 or 3 carbon atoms, where if X 2 is 3 carbon atoms, one of the carbon atoms is not included in the polymer backbone; R 3 is H or CH3; R 4 For C1 to C 20 Alkyl group, -COR 7 -or-(C=O)-OCR 7 -, where R 7 For C1 to C 20 Alkyl groups; X 3 is 2 or 3 carbon atoms, where if X 3 is 3 carbon atoms, one of the carbon atoms is not included in the polymer backbone; R 5 is H or CH3; R 6 For C1 to C 20 Alkyl group, -COR 8 -or-(C=O)-OCR 8 -, where R 8 For C1 to C 20 Alkyl groups; Z 1 NH or O; X 4 is 2 or 3 carbon atoms, where if X 4 is 3 carbon atoms, one of the carbon atoms is not included in the polymer backbone; POL 1 is a polymer comprising at least one of a polyether or a polyester, wherein the polymer has a theoretical number average molecular weight of 200 to 3,000; X 5 is 2 or 3 carbon atoms, where if X 5 is 3 carbon atoms, one of the carbon atoms is not included in the polymer backbone; POL 2 is a polymer comprising at least one of a polyether or a polyester, wherein the polymer has a theoretical number average molecular weight of 200 to 3,000; Z 2 NH or O; a is an integer between 1 and 500; b is an integer between 1 and 500; c is 0, or an integer between 1 and 100; d is 0, or an integer between 1 and 100; e is 0, or an integer between 1 and 100; and f is 0, or an integer between 1 and 100; in: If c is 0, then d is at least 1; if d is 0, then c is at least 1; If e is 0, then f is at least 1; and if f is 0, then e is at least 1.

2. The thermosetting composition according to claim 1, wherein the particulate solid is present in an amount of 20 wt% to 80 wt%, based on the total weight of the thermosetting composition.

3. The thermosetting composition of claim 1 or claim 2, wherein the particulate solid comprises at least one of an extender, a reinforcing material or a functional filler.

4. The thermosetting composition of claim 3, wherein the extender comprises at least one of calcium carbonate, talc, barium sulfate, alumina, or quartz.

5. A thermosetting composition according to claim 3 or claim 4, wherein the reinforcing material comprises at least one type of fiber material.

6. The thermosetting composition according to any one of claims 3 to 5, wherein the functional filler comprises at least one of a flame retardant material or a pigment.

7. The thermosetting composition according to any one of claims 1 to 6, wherein the thermosetting resin is present in an amount of 80 wt% to 20 wt% based on the total weight of the thermosetting composition.

8. The thermosetting composition according to any one of claims 1 to 7, wherein the thermosetting resin comprises an epoxy resin, an unsaturated polyester resin, a vinyl ester resin, a polyurethane resin or a phenolic resin.

9. The thermosetting composition according to any one of claims 1 to 8, wherein the coupling agent is present in an amount of 0.5 wt% to 5 wt%, based on the total weight of the thermosetting composition.

10. The thermosetting composition according to any one of claims 1 to 9, wherein the coupling agent comprises at least 90 wt. % of monomer units a, b, c, d, e and f according to formula I, based on the total weight of the coupling agent.

11. The thermosetting composition according to any one of claims 1 to 10, wherein the coupling agent comprises at least 70 wt. % of monomer units a and b according to formula I, based on the total weight of the coupling agent.

12. The thermosetting composition according to any one of claims 1 to 11, wherein the coupling agent comprises not more than 30 wt. % of monomer units c, d, e and f according to formula I, based on the total weight of the coupling agent.

13. The thermosetting composition according to any one of claims 1 to 12, wherein the coupling agent comprises at least 50% by weight of monomer units a according to formula I, based on the total weight of the coupling agent.

14. The thermosetting composition according to any one of claims 1 to 13, wherein the coupling agent comprises not more than 40 wt% of the monomer unit b according to formula I, based on the total weight of the coupling agent. 15 . The thermosetting composition according to claim 1 , wherein a is an integer from 5 to 500. 16 . The thermosetting composition according to claim 1 , wherein a is an integer from 20 to 50. 17 . The thermosetting composition according to claim 1 , wherein b is an integer from 2 to 100.

18. The thermosetting composition according to any one of claims 1 to 17, wherein b is an integer from 3 to 12.

19. The thermosetting composition according to any one of claims 1 to 18, wherein the ratio of a to b is from 1:1 to 10:

1.

20. The thermosetting composition according to any one of claims 1 to 19, wherein c is an integer from 3 to 12.

21. The thermosetting composition according to any one of claims 1 to 20, wherein d is an integer from 3 to 12.

22. The thermosetting composition according to any one of claims 1 to 21, wherein e is an integer from 4 to 16.

23. The thermosetting composition according to any one of claims 1 to 22, wherein f is an integer from 4 to 16.

24. The thermosetting composition according to any one of claims 1 to 23, wherein the coupling agent comprises up to 10% by weight of other monomer units other than monomer units a, b, c, d, e and f according to formula I.

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