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US-12617901-B2 - Compositions containing oxamide-functional siloxanes

US12617901B2US 12617901 B2US12617901 B2US 12617901B2US-12617901-B2

Abstract

A composition includes thermoplastic polymers and at least one organosilicon compound of the general formula R 3-a-b (OR 1 ) a R 2 b Si[OSiR 2 ] p [OSiRR 2 ] q [OSiR 2 2 ] r OSiR 3-a-b (OR 1 ) a R 2 b (I), wherein a+b is ≤3 and at least one R 2 radical is present.

Inventors

  • Oliver Schäfer
  • Oliver Fuhrmann
  • Michael JOACHIMBAUER

Assignees

  • WACKER CHEMIE AG

Dates

Publication Date
20260505
Application Date
20200903

Claims (11)

  1. 1 . A composition comprising (A) A thermoplastic polymer, and (B) at least one organosilicon compound of the formula R 3-a-b (OR 1 ) a R 2 b Si[OSiR 2 ] p [OSiRR 2 ] q [OSiR 2 2 ] r OSiR 3-a-b (OR 1 ) a R 2 b (I), where R are each identical or different and are monovalent, SiC-bonded hydrocarbon radicals having 1 to 6 carbon atoms, R 1 are each identical or different and are hydrogen or monovalent, optionally substituted hydrocarbon radicals, R 2 is an SiC-bonded unit of the formula R 3 —X—[CO—CO]—X—R 4 — (II) where X is —NR x —, R 3 are each identical or different and are monovalent, optionally substituted hydrocarbon radicals having at least 6 carbon atoms, R 4 are divalent, optionally substituted hydrocarbon radicals having 1 to 40 carbon atoms, wherein individual carbon atoms are optionally replaced by oxygen atoms or —NR z —, R x are each identical or different and are hydrogen or monovalent, optionally substituted hydrocarbon radicals having 1 to 20 carbon atoms, wherein individual carbon atoms may be replaced by oxygen atoms, R z are each identical or different and are hydrogen or monovalent, optionally substituted hydrocarbon radicals having 1 to 20 carbon atoms, wherein individual carbon atoms may be replaced by oxygen atoms, a is 0, 1, 2 or 3, b is 0 or 1, p is an integer from 1 to 1000, q is 0 or an integer from 1 to 100 and r is 0 or an integer from 1 to 100, with the proviso that a+b is ≤3 and at least one R 2 radical is present.
  2. 2 . The composition of claim 1 , wherein component (A) comprises polyethylene, polypropylene, polyamide, polyethylene terephthalate or polybutylene terephthalate.
  3. 3 . The composition of claim 1 , wherein organosilicon compounds of the formula (I) have a number-average molecular weight Mn of 1000 g/mol to 35,000 g/mol.
  4. 4 . The composition of claim 1 , wherein organosilicon compounds of the formula (I) have a number-average molecular weight Mn of 3000 g/mol to 20,000 g/mol.
  5. 5 . The composition of claim 1 , wherein component (B) is used in amounts of 0.05 parts by weight to 10 parts by weight, based on 100 parts by weight of component (A).
  6. 6 . The composition of claim 1 , wherein said composition, in addition to components (A) and (B), comprises at least one further substance selected from the group consisting of inorganic fillers (C), organic or inorganic fibers (D), flame retardants (E), biocides (F), pigments (G), UV absorbers (H) and HALS stabilizers (I).
  7. 7 . A composition comprising (A) thermoplastic polymers and (B) at least one organosilicon compound of the general formula R 3-a-b (OR 1 ) a R 2 b Si[OSiR 2 ] p [OSiRR 2 ] q [OSiR 2 2 ] r OSiR 3-a-b (OR 1 ) a R 2 b (I), where R may be identical or different and is a monovalent, SiC-bonded hydrocarbon radical having 1 to 6 carbon atoms, R 1 each are identical or different and are hydrogen or monovalent, optionally substituted hydrocarbon radicals, R 2 is an SiC-bonded unit of the formula R 3 —X—[CO—CO]—X—R 4 — (II) where X is —NR x —, R 3 each are identical or different and are monovalent, optionally substituted hydrocarbon radicals having at least 6 carbon atoms, R 4 are divalent alkylene radicals having 1 to 40 carbon atoms, wherein individual carbon atoms are optionally replaced by oxygen atoms or —NR z —, R x are each identical or different and are hydrogen or monovalent, optionally substituted hydrocarbon radicals having 1 to 20 carbon atoms, wherein individual carbon atoms may be replaced by oxygen atoms, R z each are identical or different and are hydrogen or monovalent, optionally substituted hydrocarbon radicals having 1 to 20 carbon atoms, wherein individual carbon atoms may be replaced by oxygen atoms, a is 0, 1, 2 or 3, b is 0 or 1, p is an integer from 1 to 1000, q is 0 or an integer from 1 to 100 and r is 0 or an integer from 1 to 100, with the proviso that a+b is ≤3 and at least one R 2 radical is present.
  8. 8 . The composition of claim 7 , wherein organosilicon compounds of the formula (I) have a number-average molecular weight Mn of 1000 g/mol to 35,000 g/mol.
  9. 9 . The composition of claim 7 , wherein R 3 is an optionally substituted aliphatic hydrocarbon radical.
  10. 10 . The composition of claim 7 , wherein R 3 contains at least 10 carbon atoms, and is an optionally substituted aliphatic hydrocarbon radical.
  11. 11 . The composition of claim 7 , wherein R 4 is a methylene or n-propylene radical.

Description

CROSS-REFERENCE TO RELATED APPLICATION This application is a U.S. National Phase Application of PCT/EP2020/074664, filed Sep. 3, 2020, the entire disclosure of which is hereby incorporated by reference. BACKGROUND The invention relates to oxamide-functional siloxanes, processes for the preparation thereof and to the use of oxamide-functional siloxanes in thermoplastic compositions. Thermoplastic polymers such as polyethylene or polypropylene make up the majority of plastics produced worldwide today. In recent years, advances in manufacturing technology for these polymers have made possible increasingly high-performance materials. Despite the inherently good processing properties, processing these still requires the use of process additives to optimize properties such as processing speed, surface quality, mold-release behavior, rheology control, and others. Besides oligomeric additives such as fatty acid amides, fatty acid esters, metal stearates, oligomeric hydrocarbon waxes (PE waxes), use is also made of higher-molecular-weight polymers such as fluoropolymers. A challenge here is to minimize as far as possible the use of these process additives so as to minimize any adverse effect on other material properties of polyolefins, such as stiffness or scratch resistance, while at the same time maximizing the desired effect in the particular case, such as increasing processing speed. There has accordingly been a search for novel additive concepts that show increased effectiveness compared to products used in the prior art. WO 2010/077477 A1 describes linear polysiloxane-poly(ox)amide copolymers that can be used as process additives in thermoplastics. The main disadvantage of using these products in these applications is the usually high molecular weight of the copolymers used, which leads to poor distribution in the matrix thermoplastics and thus to process improvements that are often insufficient. EP-B1 555 893 describes polymeric stabilizers based on oxamidosilanes and hydrolysates thereof in combination with copper powder, which can be used in polyolefins. An influence on the processing properties of the polyolefins was not disclosed here. It has surprisingly been found that by combining linear silicones having relatively low molecular weights and small proportions of specific aliphatic oxamido substituents, compounds were obtained which exhibit significant process improvements when mixed into thermoplastics. BRIEF SUMMARY Embodiments of a composition are described below. In an embodiment, the composition comprises (A) thermoplastic polymers and (B) at least one organosilicon compound of the general formula R3-a-b(OR1)aR2bSi[OSiR2]p[OSiRR2]q[OSiR22]rOSiR3-a-b(OR1)aR2b(I), where R may be identical or different and is a monovalent, optionally substituted, SiC-bonded hydrocarbon radical,R1 may be identical or different and is a hydrogen atom or a monovalent, optionally substituted hydrocarbon radical,R2 is a SiC-bonded unit of the general formula R3—X—[CO—(CO)n]—X—R4—  (II) where X may be identical or different and is —O— or —NRx—,R3 may be identical or different and are monovalent, optionally substituted hydrocarbon radicals having at least 6 carbon atoms,R4 are divalent, optionally substituted hydrocarbon radicals having 1 to 40 carbon atoms, wherein individual carbon atoms may be replaced by oxygen atoms or —NRz—,Rx may be identical or different and is a hydrogen atom or monovalent, optionally substituted hydrocarbon radicals having 1 to 20 carbon atoms, wherein individual carbon atoms may be replaced by oxygen atoms,Rz may be identical or different and is a hydrogen atom or monovalent, optionally substituted hydrocarbon radicals having 1 to 20 carbon atoms, wherein individual carbon atoms may be replaced by oxygen atoms,n is 0 or 1,a is 0, 1, 2 or 3,b is 0 or 1,p is an integer from 1 to 1000,q is 0 or an integer from 1 to 100 andr is 0 or an integer from 1 to 100. In this embodiment, a+b is ≤3 and at least one R2 radical is present. DETAILED DESCRIPTION Examples of polymers (A) used according to the invention are polyethylene, polypropylene, polyamide, polyethylene terephthalate, polybutylene terephthalate, thermoplastic elastomers based on crosslinked rubber, ethylene-vinyl acetate, polyhydroxybutyrate and/or copolymers or mixtures thereof, and also polystyrene, impact-modified polystyrene, styrene-acrylonitrile copolymers, acrylonitrile-butadiene-styrene copolymers, polyvinyl chloride, polyvinylidene fluoride, ethylene tetrafluoroethylene (ETFE), polymethyl methacrylate, polycarbonate, polyaryletherketone, polyacrylonitrile, polyetherimide, polyethylene naphthalate, polyethersulfone, polyimide, polyketone, polyoxymethylene, polyphenylene sulfide, polyphenylene sulfone, polysulfone and copolymers or mixtures thereof. Preferred examples of component (A) used according to the invention are low and high density polyethylenes (LDPE, LLDPE, HDPE), homo- and copolymers of propylene with, for example, ethylene,