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US-20260125504-A1 - ORGANOSILICONE MATERIAL AND LATEX COMPOSITION COMPRISING THE SAME

US20260125504A1US 20260125504 A1US20260125504 A1US 20260125504A1US-20260125504-A1

Abstract

An organo-functional silicone is shown and described herein. The organo-functional silicone comprises an acrylate/methacrylate functional group and a polyalkyleneoxide functional group. The organo-functional silicone is water dispersible and may be reacted with a free-radical polymerizable monomer under conditions to form a latex emulsion.

Inventors

  • Debdeep Maity
  • Sashivinay Kumar Gaddam
  • Vinu Krishnan Appukuttan
  • Bhanu Pratap
  • Yogesh Digamber Marathe
  • Yogesh Tiwary
  • Karthikeyan Sivasubramanian

Assignees

  • MOMENTIVE PERFORMANCE MATERIALS INC.

Dates

Publication Date
20260507
Application Date
20251103
Priority Date
20241104

Claims (20)

  1. 1 . An organo-functional silicone monomer of the formula (I): where: M is R 1 (R 2 )R 3 )SiO 1/2 D 1 is (R 4 )(R 5 )SiO 2/2 D 2 is (R 6 )(R 7 )SiO 2/2 D 3 is (R 8 )(R 9 )SiO 2/2 T 1 is (R 10 )SiO 3/2 Q is SiO 4/2 R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 8 are independently selected from a C1-C200 hydrocarbon, which optionally may have a heteroatom substituted for one or more of the hydrogen atoms; R 7 is a group —R 11 —O—C(O)—C(R 12 )═CH 2 , where R 11 is a C2-C100 hydrocarbon optionally substituted with one or more heteroatoms, and R 12 is H or a C1-C10 hydrocarbon; R 9 is a polyoxyalkyelene group —R 13 —O—(C 2 H 4 O) g (C 3 H 6 O) h (C 4 H 8 O) i —R 14 where R 13 is a C1-C50 hydrocarbon, and R 14 is H or a C1-C10 hydrocarbon; R 10 is selected from hydrocarbon having 1 to 200 carbon atoms, which optionally may have a heteroatom substituted for one or more of the hydrogen atoms; R 7 ; or R 9 ; a, b, c, and d are individually positive integers of from 1 to about 100; e is 0 to about 100, with the proviso that when R 10 is R 7 , e is 1 and c is 0; f is 0 to about 100; g is 1 to about 100; and h and i are individually 0 to about 100.
  2. 2 . The organo-functional silicone of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 8 are independently selected form a C1-C30 alkyl, a C6-C30 aryl, or a C7-C30 aralkyl.
  3. 3 . The organo-functional silicone of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 8 are each independently selected from a C1-C10 alkyl.
  4. 4 . The organo-functional silicone of claim 1 , wherein R 11 has a structure —R 15 —R 16 —, where R 15 is a divalent C2-C20 alkyl, and R 16 is a divalent C5-C20 cyclic alkyl group.
  5. 5 . The organo-functional silicone of claim 4 , wherein R 16 is a hydroxy functional divalent cyclohexyl group.
  6. 6 . The organo-functional silicone of claim 1 , wherein R 11 is selected from a C2-C20 alkyl.
  7. 7 . The organo-functional silicone of claim 6 , wherein R 12 is H or methyl.
  8. 8 . The organo-functional silicone of claim 1 , wherein h and i are each 0.
  9. 9 . The organo-functional silicone of claim 1 , wherein R 14 is methyl.
  10. 10 . The organo-functional silicone of claim 1 , wherein c is 1-100.
  11. 11 . The organo-functional silicone of claim 1 , wherein c is 1-10.
  12. 12 . The organo-functional silicone of claim 1 , wherein c is 1-2.
  13. 13 . The organo-functional silicone of claim 1 , wherein the ratio of d*g to c is 1:1 or greater.
  14. 14 . The organo-functional silicone of claim 1 , wherein the ratio of d*g to c is from 1:1 to 100:1.
  15. 15 . The organo-functional silicone of claim 1 , wherein a is 2; b is 1-100; c is 1; d is 1-100; and e and f are 0.
  16. 16 . The organo-functional silicone of claim 1 , wherein D 1 b is selected from D 1′ b′ and D 1″ b″ where D 1′ b′ is selected from (R 4′ )(R 5′ )SiO 2/2 where R 4′ and R 5′ are a C1-C3 alkyl, and D 1″ b″ is selected from (R 4″ )(R 5″ )SiO 2/2 where R 4″ is a C1-C3 alkyl, and R 5″ is a C4-C20 alkyl, b′ is 1-100 and b″ is 1-100.
  17. 17 . The organo-functional silicone of claim 16 , wherein R 4′ and R 5′ are a C1-C3 alkyl, R 4″ is a C1-C3 alkyl, and R 5″ is a C4-C10 alkyl, b′ is 1-20 and b″ is 1-20.
  18. 18 . The organo-functional silicone of claim 16 , wherein R 4′ , R 5′ , and R 4″ are each methyl, R 5″ is a C4-C10 alkyl, b′ is 1-20 and b″ is 1-20.
  19. 19 . The organo-functional silicone of claim 1 , wherein the organo-functional silicone is water dispersible.
  20. 20 . A composition comprising: (a) one or more organo-functional silicone of any of claim 1 ; and (b) optionally one or more free-radical polymerizable organic monomers; and (c) water.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS This application claims priority to and the benefit of India Provisional Application No. 202411084014, titled “ORGANOSILICONE MATERIAL AND LATEX COMPOSITION COMPRISING THE SAME,” filed on Nov. 4, 2024, the entire disclosure of which is incorporated herein by reference. FIELD OF INVENTION The present invention relates to an organic-modified silicone, compositions, copolymers, and emulsions comprising the same. In particular, the present invention relates to acrylate-functional silicones and compositions comprising the same. The acrylate-functional silicones can be employed to form copolymers such as, for example, latex copolymers suitable for use in a variety of applications and compositions. BACKGROUND Paints based on conventional acrylic latexes have limited physical properties with respect to, for example, hydrophobicity, elastomeric properties, efflorescence, water vapor permeability, durability and the like. The addition of siloxanes to latex compositions may improve one or more of those properties. While siloxanes can be added to the formulation, it can be particularly beneficial to incorporate the siloxane material as a monomer during polymerization of the acrylic latex to achieve greater benefits. It is, however, difficult to incorporate acrylate-functional silicone monomers into the acrylic latex polymer made using emulsion polymerization process due to the hydrophobic nature of many acrylic-functional siloxanes. SUMMARY The following presents a summary of this disclosure to provide a basic understanding of some aspects. This summary is intended to neither identify key or critical elements nor define any limitations of embodiments or claims. Furthermore, this summary may provide a simplified overview of some aspects that may be described in greater detail in other portions of this disclosure. Provided is an organic-modified silicone. In aspects and embodiments, the organic-modified silicone is an acrylate-functional silicone that is free radical polymerizable with other polymerizable monomers. The organic-modified silicone is water dispersible and suitable for use in forming an emulsion. The acrylate-functional silicone may be employed to form a latex copolymer suitable for use in a variety of applications such as, but not limited to, coatings, adhesives, sealants, personal care formulations, and the like. In one aspect, provided is a An organo-functional silicone monomer of the formula (I): where: M is R1(R2)R3)SiO1/2 D1 is (R4)(R5)SiO2/2 D2 is (R6)(R7)SiO2/2 D3 is (R8)(R9)SiO2/2 T1 is (R10)SiO3/2 Q is SiO4/2 R1, R2, R3, R4, R5, R6, and R8 are independently selected from a C1-C200 hydrocarbon, which optionally may have a heteroatom substituted for one or more of the hydrogen atoms;R7 is a group —R11—O—C(O)—C(R12)═CH2, where R11 is a C2-C100 hydrocarbon optionally substituted with one or more heteroatoms, and R12 is H or a C1-C10 hydrocarbon;R9 is a polyoxyalkyelene group —R13—O—(C2H4O)g(C3H6O)h(C4H8O)i—R14 where R13 is a C1-C50 hydrocarbon, and R14 is H or a C1-C10 hydrocarbon;R10 is selected from hydrocarbon having 1 to 200 carbon atoms, which optionally may have a heteroatom substituted for one or more of the hydrogen atoms; R7; or R9;a, b, c, and d are individually positive integers of from 1 to about 100;e is 0 to about 100, with the proviso that when R10 is R7, e is 1 and c is 0;f is 0 to about 100;g is 1 to about 100; andh and i are individually 0 to about 100. In one embodiment, R1, R2, R3, R4, R5, R6, and R8 are independently selected form a C1-C30 alkyl, a C6-C30 aryl, or a C7-C30 aralkyl. In one embodiment, R1, R2, R3, R4, R5, R6, and R8 are each independently selected from a C1-C10 alkyl. In one embodiment in accordance with any previous embodiment, R11 has a structure —R15—R16—, where R15 is a divalent C2-C20 alkyl, and R16 is a divalent C5-C20 cyclic alkyl group. In one embodiment, R16 is a hydroxy functional divalent cyclohexyl group. In one embodiment in accordance with any previous embodiment, R11 is selected from a C2-C20 alkyl. In one embodiment in accordance with any previous embodiment, R12 is H or methyl. In one embodiment in accordance with any previous embodiment, h and i are each 0. In one embodiment in accordance with any previous embodiment, R14 is methyl. In one embodiment in accordance with any previous embodiment, c is 1-100. In one embodiment in accordance with any previous embodiment, c is 1-10. In one embodiment in accordance with any previous embodiment, c is 1-2. In one embodiment in accordance with any previous embodiment, the ratio of d*g to c is 1:1 or greater. In one embodiment in accordance with any previous embodiment, the ratio of d*g to c is from 1:1 to 100:1. In one embodiment in accordance with any previous embodiment, a is 2; b is 1-100; c is 1; d is 1-100; and e and fare 0 In one embodiment in accordance with any previous embodiment, D1b is selected from D1′b′ and D1″b″ where D1′b′ is selected from (R4′)(R5′)SiO2/