# US 11,078,410 B2 · Modified reactive resin compositions and use thereof for coating propping agents

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- Number: US 11,078,410 B2
- Document ID: US11078410B2
- Status: Granted
- Kind: B2
- Application number: 16/071,991
- Filed: 2017-01-23
- Published: 2019-01-24
- Granted: 2021-08-03
- Earliest claimed: 2016-01-28
- Assignees: Wacker Chemie AG
- Applicants: Wacker Chemie AG
- Inventors: Sebastian Knoer; Daniel Calimente; Arndt Schlosser
- Web page: https://patentgrep.com/patent/US11078410B2

## CPC

- C09K 8/805: {Coated proppants}
- C08L 61/06: of aldehydes with phenols
- C09D 163/04: Epoxynovolacs
- C09K 8/62: Compositions for forming crevices or fractures
- E21B 43/267: reinforcing fractures by propping
- C08G 77/14: containing silicon bound to oxygen-containing groups
- C08G 77/445: containing polyester sequences
- C08G 77/46: containing polyether sequences
- C08L 83/06: containing silicon bound to oxygen-containing groups (C08L83/12 takes precedence)
- C08L 83/12: containing polyether sequences
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- E21B: EARTH OR ROCK DRILLING; OBTAINING OIL, GAS, WATER, SOLUBLE OR MELTABLE MATERIALS OR A SLURRY OF MINERALS FROM WELLS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

Coated proppants useful in fracking operations in oil and gas production are coated with a novolac resin containing a linear or cyclic organopolysiloxane of specific composition. The coatings are more fracture resistant, thus producing less fines during use, resulting in longer production campaigns.

## Claims

### Claim 1

A reactive resin composition, comprising:
(A) 80%-99.8% by weight of at least one reactive phenol novolac resin, and
(B) 0.2%-20% by weight of at least one linear or cyclic organopolysiloxane,
wherein the weight percentages of (A) and (B) are based on the total weight of the reactive resin composition, and
(C) optionally, a hardening agent,
with the provisos that:
(B) has at least 3 successive Si—O units;
(B) has at least one Si—C-bonded, pendant or terminal organic R1 radical, where
R1 contains at least 6 atoms independently selected from the group consisting of C, N, P, O and S, and
at least 3 of these atoms in R1 are C;
in (B) the ratio of the sum total of all carbon atoms to the sum total of all silicon atoms is at least 3;
(B) is in free-flowing form at 20° C., or is convertible to free-flowing form by heating to a temperature in a range of up to 250° C.; and
in (B) when R1 is polymeric, it is a polymer selected from the group consisting of polyethers, polycaprolactones, polyesters, polyvinyl acetates, polystyrenes, polymethylmethacrylates, and mixtures thereof.

### Claim 2 (depends on 1)

The reactive resin composition of claim 1, wherein (B) has at least 5 successive Si—O units.

### Claim 3 (depends on 1)

A process for preparing a reactive resin composition of claim 1, comprising dissolving and/or dispersing (B) in (A) wherein (B) is free-flowing at 20° C.; has been rendered free-flowing by prior heating up to 250° C.; or has been dissolved in a suitable solvent.

### Claim 4 (depends on 1)

A coating, moulding, workpiece, or foam, comprising a cured reactive resin composition of claim 1.

### Claim 5 (depends on 1)

A process for coating proppants, comprising applying a composition of claim 1 to proppant particles, and at least partially curing the composition.

### Claim 6

A reactive resin composition, comprising:
(A) 80%-99.8% by weight of at least one reactive phenol novolac resin, and
(B) 0.2%-20% by weight of at least one linear or cyclic organopolysiloxane, wherein the weight percentages of (A) and (B) are based on the total weight of the reactive resin composition, and
(C) optionally a hardening agent,
with the provisos that:
(B) has at least 3 successive Si—O units;
(B) has at least one Si—C-bonded, pendant or terminal organic R1 radical, where
R1 contains at least 6 atoms independently selected from the group consisting of C, N, P, O and S, and
at least 3 of these atoms in R1 are C;
in (B) the ratio of the sum total of all carbon atoms to the sum total of all silicon atoms is at least 3;
(B) is in free-flowing form at 20° C., or is convertible to free-flowing form by heating to a temperature in a range of up to 250° C.; and
wherein at least one R1 comprises an epoxy radical; an amino radical of the formula
—R6—[NR7—R8—]nNR72 (VIII)
where
R6 is a divalent linear or branched hydrocarbyl radical having 3 to 18 carbon atoms,
R7 is a hydrogen atom, an alkyl radical having 1 to 8 carbon atoms or an acyl radical,
R8 is a divalent hydrocarbyl radical having 1 to 6 carbon atoms,
n is 0, 1, 2, 3 or 4; or a carboxyalkyl radical.

### Claim 7 (depends on 1)

The reactive resin composition of claim 1, which when hardened has a K1c of at least 0.55 MN/m3/2.