Oxamide-functional siloxane-containing compositions

Abstract

The present invention relates to a thermoplastic polymer comprising (A) a thermoplastic polymer and (B) a polymer having the general formula: R 3-a-b (OR 1 ) a R 2 b Si[OSiR2] p [OSiRR 2 ] q [OSiR 2 2] r OSiR 3-a-b (OR 1 ) a R 2 b (I) wherein the radicals and indices have the meanings defined in claim 1. The present invention relates to a composition comprising at least one organosilicon compound of the formula: The present invention relates to a method for preparing a composition and a molded article made therefrom, an oxamide-functional siloxane, and a method for making the oxamide-functional siloxane.

Description

[Technical field]

[0001] The present invention relates to oxamide-functional siloxanes, methods for their preparation, and their use in thermoplastic compositions. [Background technology]

[0002] Thermoplastic polymers such as polyethylene and polypropylene account for the majority of plastics produced worldwide today. In recent years, advances in the manufacturing technology of these polymers have resulted in increasingly high-performance materials. However, despite their inherently excellent processability, processing additives must be used to optimize properties such as processing speed, surface properties, release properties, and rheology control. Oligomeric additives such as fatty acid amides, fatty acid esters, metal stearates, and oligomeric hydrocarbon waxes (PE waxes) are used, as well as polymeric polymers such as fluoropolymers. The challenge is to use as few of these processing additives as possible to maximize the effects required in certain cases, such as increased processing speed, while minimizing the negative effects on other material properties such as the stiffness and scratch resistance of polyolefins. Therefore, novel additive concepts have been sought that show higher effects than the products used in the prior art.

[0003] WO2010 / 077477A1 describes linear polysiloxane-poly(oxy)amide copolymers that can be used as processing additives for thermoplastics. The main drawback of using these products for these applications is the usual high molecular weight copolymers used, which lead to poor distribution in the matrix thermoplastic and therefore often insufficient processing improvement.

[0004] EP 555 893 B1 describes polymer stabilizers based on oxamidosilane and its hydrolysates in combination with copper powder, which can be used for polyolefins. The influence on the processing properties of the polyolefins is not disclosed therein. Summary of the Invention

[0005] It has surprisingly been found that the combination of a linear silicone having a relatively low molecular weight with small amounts of certain aliphatic oxamide substituents results in compounds which exhibit significant processing improvements when incorporated into thermoplastic resins. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0006] The present invention relates to (A) a thermoplastic polymer, and (B) General formula: R 3-a-b (OR 1 ) a R 2 b Si[OSiR2] p [OSiRR 2 ] q [OSiR 2 2] r OSiR 3-a-b (OR 1 ) a R 2 b (I) {In the formula, R are the same or different, optionally substituted, monovalent SiC-bonded hydrocarbon radicals; R 1 are the same or different and are a hydrogen atom or an optionally substituted monovalent hydrocarbon radical, R 2 is of the general formula: R 3 -X-[CO-(CO) n ]-XR 4 - (II) (In the formula, X may be the same or different and is -O- or -NR x - and R 3 are the same or different, optionally substituted monovalent hydrocarbon radicals having at least 6 carbon atoms; R 4is an optionally substituted divalent hydrocarbon radical having 1 to 40 carbon atoms, each carbon atom being an oxygen atom or -NR z -, R x are the same or different and are a hydrogen atom or an optionally substituted monovalent hydrocarbon radical having 1 to 20 carbon atoms, each of which may be substituted with an oxygen atom; R z are the same or different and are a hydrogen atom or an optionally substituted monovalent hydrocarbon radical having 1 to 20 carbon atoms, each of which may be substituted with an oxygen atom; n is 0 or 1) is a SiC bond unit, 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; r is 0 or an integer from 1 to 100; However, a+b is ≦3 and at least one R 2 group is present. At least one organosilicon compound of The present invention relates to a composition comprising:

[0007] Examples of polymers (A) to be 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 their copolymers or mixtures; 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.

[0008] Preferred examples of component (A) to be used according to the invention are low and high density polyethylenes (LDPE, LLDPE, HDPE), homo- and copolymers of propylene with, for example, ethylene, butene, hexene and octene (PP), olefin copolymers such as ethylene-vinyl acetate copolymer (EVA), ethylene-methyl acrylate copolymer (EMA), ethylene-butyl acrylate copolymer (EBA), polyvinyl chloride (PVC), polyvinyl chloride-ethylene copolymers, polystyrene (PS, HIPS, EPS), particularly preferably polyethylene, polypropylene, polyamide, polyethylene terephthalate or polybutylene terephthalate.

[0009] The polyolefins (A) used according to the invention particularly preferably have the general formula: [-CR 6 R 7 -CR 8 R 9 -] x (III) Includes units of. In the above formula, R 6 , R 7 , R8 , and R 9 are each independently a hydrogen atom, an optionally substituted saturated hydrocarbon group, an unsaturated hydrocarbon group, an aromatic hydrocarbon group, a vinyl ester group or a halogen atom, and x is a number from 100 to 100,000.

[0010] Preferably, the group R 6 , R 7 , R 8 , and R 9 are each independently a hydrogen atom, a saturated hydrocarbon group such as a methyl, butyl, or hexyl group, an aromatic hydrocarbon group such as a phenyl group, or a halogen atom such as chlorine or fluorine, and are particularly preferably a hydrogen atom, a methyl group, or a chlorine atom.

[0011] Preferred monomers for preparing component (A) are ethylene, propylene, vinyl chloride, vinyl acetate, styrene, 1-butene, 1-hexene, 1-octene or butadiene or mixtures thereof, more preferably ethylene, propylene or vinyl chloride.

[0012] The polymer (A) used according to the invention is in particular a homopolymer or copolymer of ethylene or propylene.

[0013] The polymer (A) is particularly preferably high density polyethylene (HDPE) or polypropylene.

[0014] For the thermoplastic polymers (A) used according to the invention, the temperature at which the loss factor (G'' / G') according to DIN EN ISO 6721-2:2008 has a value of 1 is preferably at least 40°C, particularly preferably at least 100°C.

[0015] The polymer structure of the thermoplastic polymer (A) is linear, but may also be branched.

[0016] The nature of the organic polymer (A) used essentially determines the processing temperature of the mixtures according to the invention.

[0017] The proportion of the thermoplastic polymer (A) in the composition according to the present invention is preferably 50% by weight to 99.99% by weight, particularly preferably 90% by weight to 99.90% by weight, and particularly preferably 97.5% by weight to 99.90% by weight.

[0018] The component (A) used in accordance with the present invention are commercially available products or can be prepared by standard chemical processes.

[0019] Examples of R include alkyl groups such as methyl, ethyl, n-propyl, isopropyl, 1-n-butyl, 2-n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and tert-pentyl groups; hexyl groups such as n-hexyl groups; heptyl groups such as n-heptyl groups; octyl groups such as n-octyl groups; isooctyl groups such as 2,2,4-trimethylpentyl groups; nonyl groups such as n-nonyl groups; decyl groups such as n-decyl groups; and n-dodecyl groups. dodecyl groups; octadecyl groups such as n-octadecyl groups; cycloalkyl groups such as cyclopentyl, cyclohexyl, cycloheptyl, and methylcyclohexyl groups; alkenyl groups such as vinyl, 1-propenyl, and 2-propenyl groups; aryl groups such as phenyl, naphthyl, anthryl, and phenanthryl groups; alkaryl groups such as o-, m-, and p-tolyl groups; xylyl and ethylphenyl groups; and aralkyl groups such as benzyl, α-, and β-phenylethyl groups.

[0020] Examples of halogenated groups R are haloalkyl groups such as 3,3,3-trifluoro-n-propyl, 2,2,2,2',2',2'-hexafluoroisopropyl and heptafluoroisopropyl groups.

[0021] The group R is preferably a monovalent hydrocarbon group having 1 to 20 carbon atoms, optionally substituted by fluorine and / or chlorine atoms, more preferably a hydrocarbon group having 1 to 6 carbon atoms, in particular a methyl, ethyl, vinyl or phenyl group.

[0022] base R 1 Examples are the groups specified for the group R, and also polyalkylene glycol groups bonded via a carbon atom.

[0023] base R 1 is preferably a hydrocarbon group, more preferably a hydrocarbon group having 1 to 8 carbon atoms, in particular a methyl or ethyl group.

[0024] base R 3 Examples of the radical R are optionally substituted hydrocarbon radicals having at least 6 carbon atoms, such as the n-hexyl or dodecyl radicals.

[0025] base R 3 is preferably an aliphatic hydrocarbon group having at least 6 carbon atoms, particularly preferably an aliphatic hydrocarbon group having at least 10 carbon atoms.

[0026] base R 4 Examples of the alkylene groups include alkylene groups such as methylene, ethylene, n-propylene, isopropylene, n-butylene, isobutylene, tert-butylene, n-pentylene, isopentylene, neopentylene, tert-pentylene, hexylene, heptylene, octylene, nonylene, decylene, dodecylene or octadecylene groups; cycloalkylene groups such as cyclopentylene, 1,4-cyclohexylene, isophoronylene or 4,4'-methylenedicyclohexylene groups; vinylene, n-hexylene, cyclohexylene, 1-propylene, aryl groups, alkenylene groups such as ethynylene or propargylene groups; arylene groups such as phenylene, bisphenylene, naphthylene, anthrylene or phenanthrylene groups; alkarylene groups such as o-, m-, p-tolylene, xylylene or ethylphenylene groups; or aralkylene groups such as benzylene, 4,4'-methylenediphenylene, α- or β-phenylethylene groups; or ethylene-propylene ether or ethylene-propylene amine groups.

[0027] base R 4 is an alkylene group, particularly preferably a methylene or n-propylene group.

[0028] base R x and R z Examples of are, each independently, a group as defined by the group R and a hydrogen atom.

[0029] base R x is preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.

[0030] base R z is preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.

[0031] X is preferably defined as -NR X -, wherein R x is as defined above.

[0032] The index n is preferably equal to one.

[0033] base R 2 Examples of H 13 C6-NH-CO-CO-NH-C3H6-, H 15 C7-NH-CO-CO-NH-C3H6-, H 17 C8-NH-CO-CO-NH-C3H6-, H 19 C9-NH-CO-CO-NH-C3H6-, H 21 C 10 -NH-CO-CO-NH-C3H6-, H 23 C 11 -NH-CO-CO-NH-C3H6-, H 25 C 12 -NH-CO-CO-NH-C3H6-, H 27 C 13 -NH-CO-CO-NH-C3H6-, H 29 C 14 -NH-CO-CO-NH-C3H6-, H 31 C 15-NH-CO-CO-NH-C3H6-、H 33 C 16 -NH-CO-CO-NH-C3H6-、H 35 C 17 -NH-CO-CO-NH-C3H6-、H 37 C 18 -NH-CO-CO-NH-C3H6-、H 39 C 19 -NH-CO-CO-NH-C3H6-、H 41 C 20 -NH-CO-CO-NH-C3H6-、H 13 C6-NH-CO-NH-C3H6-、H 15 C7-NH-CO-NH-C3H6-、H 17 C8-NH-CO-NH-C3H6-、H 19 C9-NH-CO-NH-C3H6-、H 21 C 10 -NH-CO-NH-C3H6-、H 23 C 11 -NH-CO-NH-C3H6-、H 25 C 12 -NH-CO-NH-C3H6-、H 27 C 13 -NH-CO-NH-C3H6-、H 29 C 14 -NH-CO-NH-C3H6-、H 31 C 15 -NH-CO-NH-C3H6-、H 33 C 16 -NH-CO-NH-C3H6-、H 35 C 17 -NH-CO-NH-C3H6-、H 37 C 18 -NH-CO-NH-C3H6-、H 39 C 19 -NH-CO-NH-C3H6-、H 41 C 20 -NH-CO-NH-C3H6-、 H 11 C6-NH-CO-CO-NH-C3H6-、H 13 C7-NH-CO-CO-NH-C3H6-、H 15 C8-NH-CO-CO-NH-C3H6-、H 17C9-NH-CO-CO-NH-C3H6-、H 19 C 10 -NH-CO-CO-NH-C3H6-、H 21 C 11 -NH-CO-CO-NH-C3H6-、H 23 C 12 -NH-CO-CO-NH-C3H6-、H 25 C 13 -NH-CO-CO-NH-C3H6-、H 27 C 14 -NH-CO-CO-NH-C3H6-、H 29 C 15 -NH-CO-CO-NH-C3H6-、H 31 C 16 -NH-CO-CO-NH-C3H6-、H 33 C 17 -NH-CO-CO-NH-C3H6-、H 35 C 18 -NH-CO-CO-NH-C3H6-、H 37 C 19 -NH-CO-CO-NH-C3H6-、H 39 C 20 -NH-CO-CO-NH-C3H6-、H 13 C6-NH-CO-CO-NH-C2H4-NH-C3H6-、H 15 C7-NH-C2H4-NH-CO-CO-NH-C3H6-、H 17 C8-NH-CO-CO-NH-C2H4-NH-C3H6-、H 19 C9-NH-CO-CO-NH-C2H4-NH-C3H6-、H 21 C 10 -NH-CO-CO-NH-C2H4-NH-C3H6-、H 23 C 11 -NH-CO-CO-NH-C2H4-NH-C3H6-、H 25 C 12 -NH-CO-CO-NH-C2H4-NH-C3H6-、H 27 C 13 -NH-CO-CO-NH-C2H4-NH-C3H6-、H 29 C 14 -NH-CO-CO-NH-C2H4-NH-C3H6-、H 31 C15 -NH-CO-CO-NH-C2H4-NH-C3H6-, H 33 C 16 -NH-CO-CO-NH-C2H4-NH-C3H6-, H 35 C 17 -NH-CO-CO-NH-C2H4-NH-C3H6-, H 37 C 18 -NH-CO-CO-NH-C2H4-NH-C3H6-, H 39 C 19 -NH-CO-CO-NH-C2H4-NH-C3H6-, and H 41 C 20 -NH-CO-CO-NH-C2H4-NH-C3H6-, preferably, H 21 C 10 -NH-CO-CO-NH-C3H6-, H 23 C 11 -NH-CO-CO-NH-C3H6-, H 25 C 12 -NH-CO-CO-NH-C3H6-, H 27 C 13 -NH-CO-CO-NH-C3H6-, H 29 C 14 -NH-CO-CO-NH-C3H6-, H 31 C 15 -NH-CO-CO-NH-C3H6-, H 33 C 16 -NH-CO-CO-NH-C3H6-, H 35 C 17 -NH-CO-CO-NH-C3H6-, H 37 C 18 -NH-CO-CO-NH-C3H6-, H 21 C 10 -NH-CO-CO-NH-C2H4-NH-C3H6-, H 23 C 11 -NH-CO-CO-NH-C2H4-NH-C3H6-, H 25 C 12 -NH-CO-CO-NH-C2H4-NH-C3H6-, H 27 C 13 -NH-CO-CO-NH-C2H4-NH-C3H6-, H 29 C14 -NH-CO-CO-NH-C2H4-NH-C3H6-,H 31 C 15 -NH-CO-CO-NH-C2H4-NH-C3H6-,H 33 C 16 -NH-CO-CO-NH-C2H4-NH-C3H6-,H 35 C 17 -NH-CO-CO-NH-C2H4-NH-C3H6-,H 37 C 18 -NH-CO-CO-NH-C2H4-NH-C3H6- or mixtures thereof, More preferably, H 25 C 12 -NH-CO-CO-NH-C3H6-, H 29 C 14 -NH-CO-CO-NH-C3H6-, H 33 C 16 -NH-CO-CO-NH-C3H6-, H 25 C 12 -NH-CO-CO-NH-C2H4-NH-C3H6-,H 29 C 14 -NH-CO-CO-NH-C2H4-NH-C3H6- or H 33 C 16 -NH-CO-CO-NH-C2H4-NH-C3H6-.

[0034] a is preferably 0 or 1, and more preferably 0.

[0035] b is preferably 0 or 1, and more preferably 1.

[0036] p is preferably an integer of 10-500, and more preferably an integer of 30-300.

[0037] q is preferably 0 or an integer of 1-20, and more preferably 0 or an integer of 1-5.

[0038] r is preferably 0 or an integer of 1 to 10, more preferably 0 or an integer of 1 to 5, and particularly preferably 0.

[0039] The organosilicon compounds of formula (I) used according to the present invention preferably have a number average molecular weight Mn of 1000 g / mol to 35000 g / mol, more preferably a number average molecular weight Mn of 3000 g / mol to 20000 g / mol.

[0040] In the present invention, the number-average molar mass Mn is determined by size-exclusion chromatography (SEC) on a Styragel HR3-HR4-HR5-HR5 column set from Waters Corp. USA, in THF against polystyrene standards, with an injection volume of 100 μl, at 60° C. and a flow rate of 1.2 ml / min, and detection with an RI (refractive index detector).

[0041] The organosilicon compounds of the formula (I) in each case preferably have a melting point at 1000 hPa of 200° C. or less, particularly preferably 100° C. or less and particularly preferably 75° C. or less.

[0042] The silicon content of the organosilicon compound of general formula (I) is preferably 25% by weight to 37.5% by weight, and more preferably 30% by weight to 37% by weight.

[0043] The organosilicon compounds of formula (I) used according to the invention preferably have the following formula: R2R 2 Si[OSiR2] p [OSiRR 2 ] q OSiR2R 2 During the ceremony, R=methyl, R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)3-, p=150, q=0, R=methyl, R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)3-, p=80, q=0, R=methyl, R 2 =H 25 C 12-NH-[CO-CO]-NH-(CH2)3-, p=250, q=0, R=methyl, R 2 =H 33 C 16 -NH-[CO-CO]-NH-(CH2)3-, p=150, q=0, R=methyl, R 2 =H 33 C 16 -NH-[CO-CO]-NH-(CH2)3-, p=80, q=0, R=methyl, R 2 =H 33 C 16 -NH-[CO-CO]-NH-(CH2)3-, p=250, q=0, R=methyl, R 2 =H 25 C 12 -NH-CO-NH-(CH2)3-, p=150, q=0, R=methyl, R 2 =H 25 C 12 -NH-CO-NH-(CH2)3-, p=80, q=0, R=methyl, R 2 =H 25 C 12 -NH-CO-NH-(CH2)3-, p=250, q=0, R=methyl, R 2 =H 33 C 16 -NH-CO-NH-(CH2)3-, p=150, q=0, R=methyl, R 2 =H 33 C 16 -NH-CO-NH-(CH2)3-, p=80, q=0, R=methyl, R 2 =H 33 C 16 -NH-CO-NH-(CH2)3-, p=250, q=0, R=methyl, R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)3-, p=150, q=2, R=methyl, R 2 =H 25 C12 -NH-[CO-CO]-NH-(CH2)3-, p=80, q=1, R=methyl, R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)3-, p=250, q=3, R=methyl, R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)2-NH-(CH2)3-, p=150, q=0, R=methyl, R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)2-NH-(CH2)3-, p=80, q=0, R=methyl, R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)2-NH-(CH2)3-, p=250, q=0, R=methyl, R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)2-NH-(CH2)3-, p=250, q=3, or The organosilicon compound of formula (I) is represented by the following formula: R3Si [OSiR2] p [OSiRR 2 ] q OSiR3(I) During the ceremony, R=methyl, R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)3-, p=150, q=2, R=methyl, R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)3-, p=80, q=1, R=methyl, R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)3-, p=250, q=4, R=methyl, R 2 =H 25 C 12 -NH-CO-NH-(CH2)3-, p=150, q=2, R=methyl, R 2 =H 25 C 12 -NH-CO-NH-(CH2)3-, p=80, q=1, R=methyl, R 2 =H 25 C 12 -NH-CO-NH-(CH2)3-, p=250, q=4, R=methyl, R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)2-NH-(CH2)3-, p=150, q=2, R=methyl, R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)2-NH-(CH2)3-, p=80, q=1, R=methyl, R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)2-NH-(CH2)3-, p=250, q=4, R=methyl, R 2 =H 33 C 16 -NH-[CO-CO]-NH-(CH2)3-, p=150, q=2, R=methyl, R 2 =H 33 C 16 -NH-[CO-CO]-NH-(CH2)3-, p=80, q=1, R=methyl, R 2 =H 33 C 16 -NH-[CO-CO]-NH-(CH2)3-, p=250, q=3, R=methyl, R 2 =H 33 C 16 -NH-[CO-CO]-NH-(CH2)2-NH-(CH2)3-, p=150, q=2, R=methyl, R 2 =H33 C 16 -NH-[CO-CO]-NH-(CH2)2-NH-(CH2)3-, p=80, q=1 R=methyl, R 2 =H 33 C 16 -NH-[CO-CO]-NH-(CH2)2-NH-(CH2)3-, p=250, q=4, and particularly preferably R2R 2 Si[OSiR2] p [OSiRR 2 ] q OSiR2R 2 During the ceremony, R=methyl, R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)3-, p=150, q=0, R=methyl, R 2 =H 33 C 16 -NH-[CO-CO]-NH-(CH2)3-, p=150, q=0, R=methyl, R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)3-, p=150, q=2, R=methyl, R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)2-NH-(CH2)3-, p=150, q=0, or The organosilicon compound of formula (I) is represented by the following formula: R3Si [OSiR2] p [OSiRR 2 ] q OSiR3 During the ceremony, R=methyl, R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)3-, p=150, q=2, R=methyl, R 2 =H 25 C12 -NH-[CO-CO]-NH-(CH2)3-, p=250, q=3, R=methyl, R 2 =H 33 C 16 -NH-[CO-CO]-NH-(CH2)3-, p=150, q=2, R=methyl, R 2 =H 33 C 16 -NH-[CO-CO]-NH-(CH2)3-, p=250, q=4, R=methyl, R 2 =H 33 C 16 -NH-[CO-CO]-NH-(CH2)2-NH-(CH2)3-, p=150, q=2 It is.

[0044] The present invention further relates to organosilicon compounds represented by the general formula: R 3-a-b (OR 1 ) a R 2 b Si[OSiR2] p [OSiRR 2 ] q [OSiR 2 2] r OSiR 3-a-b (OR 1 ) a R 2 b (I) {In the formula, R are the same or different, optionally substituted, monovalent SiC-bonded hydrocarbon radicals; R 1 are the same or different and are a hydrogen atom or an optionally substituted monovalent hydrocarbon radical, R 2 is of the general formula: R 3 -X-[CO-CO]-XR 4 - (II) (In the formula, X may be the same or different and is -NR x - and R3 are the same or different, optionally substituted monovalent hydrocarbon radicals having at least 6 carbon atoms; R 4 is an optionally substituted divalent hydrocarbon radical having 1 to 40 carbon atoms, each carbon atom being an oxygen atom or -NR z -, R x are the same or different and are a hydrogen atom or an optionally substituted monovalent hydrocarbon radical having 1 to 20 carbon atoms, each of which may be substituted with an oxygen atom; R z may be the same or different and are hydrogen atoms or optionally substituted monovalent hydrocarbon groups having 1 to 20 carbon atoms, each of which may be substituted with an oxygen atom. is a SiC bond unit, a is 0, 1, or 2; b is 0 or 1; p is an integer from 1 to 1000; q is 0 or an integer from 1 to 100; r is 0 or an integer from 1 to 100; However, a+b is ≦3 and at least one R 2 group is present.

[0045] In the organosilicon compounds (B) used according to the invention or in the organosilicon compounds of formula (I) according to the invention, p is preferably equal to or greater than b+r+q, with b+r+q being ≧1.

[0046] In the organosilicon compounds (B) used according to the invention or in the organosilicon compounds of formula (I) according to the invention, it is particularly preferred if p is >5×(b+q+r), in particular p>20×(b+q+r), with b+r+q being ≧1.

[0047] The present invention relates to a compound having the general formula: R 3-a-b (OR 1 ) a R 11b Si[OSiR2] p [OSiRR 11 ] q [OSiR 11 2] r OSiR 3-a-b (OR 1 ) a R 11 b (I') {In the formula, R, R 1 , a, b, p, q and r have the definitions given above; R 11 is of the general formula: R 10 -O-[CO-CO]-NR x -R 4 - (II') (In the formula, R 4 , R x and n each have the definition given above. R 10 is a hydrogen atom or an optionally substituted monovalent hydrocarbon radical, optionally interrupted by heteroatoms; However, a+b is ≦3 and at least one R 11 (group exists) is a SiC bond unit. of organosilicon compounds General formula: R 3 -NR x -H (IV) (In the formula, R 3 and R x has the definition defined above.) with an organic compound of the formula (I) to produce an oxamide-functional siloxane.

[0048] base R 10 Examples of are those given for the radical R, preferably the methyl, ethyl or propyl radical, particularly preferably the methyl or ethyl radical.

[0049] The organosilicon compounds of formula (I') used according to the present invention are commercially available products or can be prepared by standard chemical processes.

[0050] The compounds of formula (IV) are preferably primary amines, particularly preferably primary aliphatic amines, in particular primary aliphatic amines having a molecular weight of more than 115 g / mol, particularly preferably dodecylamine, tetradecylamine, hexadecylamine or octadecylamine.

[0051] The compounds of formula (IV) used according to the present invention are commercially available products or can be prepared by standard chemical processes.

[0052] In the process according to the invention, the compound of formula (IV) is preferably used in an amount of 1 to 15% by weight, particularly preferably 2 to 10% by weight and in particular 3 to 8% by weight, in each case based on the weight of the organosilicon compound of formula (I').

[0053] In the process according to the invention, the organosilicon compound of formula (I') and the compound of formula (IV), and optionally further components, can be mixed in any manner known in the art. In this case, the organosilicon compound of formula (I') is preferably charged initially into the reactor, and the organic compound of formula (IV) is metered in. This metered addition according to the invention can be carried out discontinuously or continuously. After or during the reaction between the organosilicon compound of formula (I') and the organic compound of formula (IV), the cleavage products formed can remain in the product or be removed by distillation. The removal by distillation can be carried out either at standard pressure or, preferably, at reduced pressure. The preferred temperature during the reaction or during the removal of the condensation products is preferably 0°C to 150°C, particularly preferably 20°C to 100°C. The preferred pressure range is preferably 10 hPa to 1500 hPa, particularly preferably 20 hPa to 1013 hPa.

[0054] The reaction according to the invention is preferably carried out using a protective gas, preferably nitrogen or argon.

[0055] The ratio between the organosilicon compound of formula (I') and the organic compound of formula (IV) is preferably selected so that the organic compound of formula (IV) is used in a molar ratio of 0.5 to 1.5 equivalents, particularly preferably 0.9 to 1.1 equivalents, in particular 0.98 to 1.02 equivalents, in each case based on the reactivating group of formula (II').

[0056] The reaction between the amine groups of the organic compounds of formula (IV) and the reactive groups (II') of the organosilicon compounds of formula (I') used according to the invention is generally almost quantitative.

[0057] The reaction mixture according to the present invention is removed from the reactor, preferably after at least partial removal of the cleavage products, preferably at a temperature above the melting point of the organosilicon compound of formula (I).

[0058] Component (B) is used in an amount of preferably 0.05 to 10 parts by weight, particularly preferably 0.1 to 5 parts by weight, and especially 0.25 to 3 parts by weight, based on 100 parts by weight of component (A) in any case.

[0059] In addition to components (A) and (B), the composition according to the invention may comprise further substances, preferably selected from inorganic fillers (C), organic or inorganic fibers (D), flame retardants (E), biocides (F), pigments (G), UV absorbers (H), HALS stabilizers (I).

[0060] Examples of optionally used inorganic fillers (C) are chalk (calcium carbonate), kaolin, silicates, silica or talc.

[0061] Examples of fibres (D) optionally used according to the invention are glass fibres, basalt fibres or wollastonite, preferably glass fibres or organic fibres such as aramid fibres, wood fibres or cellulose fibres.

[0062] When inorganic fibers (D) are used, the amount is preferably 1% by weight to 50% by weight, particularly preferably 5% by weight to 35% by weight, in each case based on the total weight of the composition. The composition according to the present invention preferably does not contain inorganic fibers (D).

[0063] If organic fibres (D) are used, the amount is preferably from 20% to 80% by weight, particularly preferably from 35% to 65% by weight, in each case based on the total weight of the composition. The composition according to the invention preferably does not contain organic fibres (D).

[0064] Examples of flame retardants (E) optionally used according to the invention are organic flame retardants based on halogenated organic compounds or inorganic flame retardants such as aluminium hydroxide (ATH) or magnesium hydroxide.

[0065] When a flame retardant (E) is used, an inorganic flame retardant such as ATH is preferred.

[0066] Examples of biocides (F) optionally used according to the invention are inorganic fungicides, such as borates, for example zinc borate, or organic fungicides, for example thiabendazole.

[0067] Examples of pigments (G) optionally used according to the invention are organic pigments or inorganic pigments such as, for example, iron oxide or titanium dioxide.

[0068] When a pigment (G) is used, the amount is preferably 0.2% by weight to 7% by weight, particularly preferably 0.5% by weight to 3% by weight, in each case based on the total weight of the composition.

[0069] Examples of UV absorbers (H) optionally used according to the invention are benzophenones, benzotriazoles or triazines.

[0070] When a UV absorber (H) is used, it is preferably a benzotriazole or a triazine.

[0071] Examples of HALS stabilizers (I) which are optionally used according to the invention are, for example, piperidine or piperidyl derivatives, in particular those available under the Tinuvin brand name from BASF SE, D-Ludwigshafen.

[0072] The composition according to the invention preferably comprises: (A) HDPE, (B) Formula R2R 2 Si[OSiR2] p [OSiRR 2 ] q OSiR2R 2 (wherein R, R 2 , p and q have the same definition as above, preferably R = methyl group, R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)3-, p=150 and q=0), optionally, (C) an inorganic filler; optionally, (D) organic or inorganic fibers; optionally (E) a flame retardant; optionally (F) a biocide; optionally (G) a pigment; optionally (H) an ultraviolet absorber, Optionally, (I) a HALS stabilizer.

[0073] More preferably, the composition according to the invention comprises: (A) LDPE, (B) Formula R2R 2 Si[OSiR2] p [OSiRR 2 ] q OSiR2R 2 (wherein R, R 2 , p and q have the same definition as above, preferably R = methyl group, R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)3-, p=150 and q=0), optionally, (C) an inorganic filler; optionally, (D) organic or inorganic fibers; optionally (E) a flame retardant; optionally (F) a biocide; optionally (G) a pigment; optionally (H) an ultraviolet absorber, Optionally, (I) a HALS stabilizer.

[0074] More preferably, the composition according to the invention comprises: (A) polypropylene, (B) Formula R2R 2 Si[OSiR2] p [OSiRR 2 ] q OSiR2R 2 (wherein R, R 2 , p and q have the same definition as above, preferably R = methyl group, R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)3-, p=150 and q=0), optionally, (C) an inorganic filler; optionally, (D) organic or inorganic fibers; optionally (E) a flame retardant; optionally (F) a biocide; optionally (G) a pigment; optionally (H) an ultraviolet absorber, Optionally, (I) a HALS stabilizer.

[0075] More preferably, the composition according to the invention comprises: (A) polyvinyl chloride, (B) Formula R2R 2 Si[OSiR2] p [OSiRR 2 ] q OSiR2R 2 (wherein R, R 2 , p and q have the same definition as above, preferably R = methyl group R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)3-, p=150 and q=0, optionally, (C) an inorganic filler; optionally, (D) organic or inorganic fibers; optionally (E) a flame retardant; optionally (F) a biocide; optionally (G) a pigment; optionally (H) an ultraviolet absorber, Optionally, (I) a HALS stabilizer.

[0076] More preferably, the composition according to the invention comprises: (A) HDPE, (B) Formula R3Si[OSiR2] p [OSiRR 2 ] q OSiR3 organosilicon compound, where R, R 2 , p and q have the same definition as above, preferably R = methyl group, R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)3-, p=150 and q=2; optionally, (C) an inorganic filler; optionally, (D) organic or inorganic fibers; optionally (E) a flame retardant; optionally (F) a biocide; optionally (G) a pigment; optionally (H) an ultraviolet absorber, Optionally, (I) a HALS stabilizer.

[0077] More preferably, the composition according to the invention comprises: (A) LDPE, (B) Formula R3Si[OSiR2] p [OSiRR 2 ] q OSiR3 organosilicon compound, where R, R 2 , p and q have the same definition as above, preferably R = methyl group, R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)3-, p=150 and q=2; optionally, (C) an inorganic filler; optionally, (D) organic or inorganic fibers; optionally (E) a flame retardant; optionally (F) a biocide; optionally (G) a pigment; optionally (H) an ultraviolet absorber, Optionally, (I) a HALS stabilizer.

[0078] More preferably, the composition according to the invention comprises: (A) polypropylene, (B) Formula R3Si[OSiR2] p [OSiRR 2 ] q OSiR3 organosilicon compound, where R, R 2 , p and q have the same definition as above, preferably R = methyl group, R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)3-, p=150 and q=2; optionally, (C) an inorganic filler; optionally, (D) organic or inorganic fibers; optionally (E) a flame retardant; optionally (F) a biocide; optionally (G) a pigment; optionally (H) an ultraviolet absorber, Optionally, (I) a HALS stabilizer.

[0079] More preferably, the composition according to the invention comprises: (A) HDPE, (B) Formula R2R 2 Si[OSiR2] p [OSiRR 2 ] q OSiR2R 2 (wherein R, R 2 , p and q have the same definition as above, preferably R = methyl group, R 2 = H 33 C 16 -NH-[CO-CO]-NH-(CH2)3-, p=150, q=0, optionally, (C) an inorganic filler; optionally, (D) organic or inorganic fibers; optionally (E) a flame retardant; optionally (F) a biocide; optionally (G) a pigment; optionally (H) an ultraviolet absorber, Optionally, (I) a HALS stabilizer.

[0080] More preferably, the composition according to the invention comprises: (A) LDPE, (B) Formula R2R 2 Si[OSiR2] p [OSiRR 2 ] q OSiR2R 2 (wherein R, R 2 , p and q have the same definition as above, preferably R = methyl group, R 2 = H 33 C 16 -NH-[CO-CO]-NH-(CH2)3-, p=150, q=0, optionally, (C) an inorganic filler; optionally, (D) organic or inorganic fibers; optionally (E) a flame retardant; optionally (F) a biocide; optionally (G) a pigment; optionally (H) an ultraviolet absorber, Optionally, (I) a HALS stabilizer.

[0081] More preferably, the composition according to the invention comprises: (A) polypropylene, (B) Formula R2R 2 Si[OSiR2] p [OSiRR 2 ] q OSiR2R 2 (wherein R, R 2 , p and q have the same definition as above, preferably R = methyl group, R 2 = H 33 C 16-NH-[CO-CO]-NH-(CH2)3-, p=150, q=0, optionally, (C) an inorganic filler; optionally, (D) organic or inorganic fibers; optionally (E) a flame retardant; optionally (F) a biocide; optionally (G) a pigment; optionally (H) an ultraviolet absorber, Optionally, (I) a HALS stabilizer.

[0082] Particularly preferably, the composition according to the invention comprises: (A) HDPE, (B) Formula R2R 2 Si[OSiR2] p [OSiRR 2 ] q OSiR2R 2 (wherein R, R 2 , p and q have the same definition as above, preferably R = methyl group, R 2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)3-, p=150 and q=0, optionally, (C) an inorganic filler; optionally, (D) organic or inorganic fibers; optionally (E) a flame retardant; optionally (F) a biocide; optionally (G) a pigment; optionally (H) an ultraviolet absorber, Optionally, (I) a HALS stabilizer.

[0083] In a further particularly preferred embodiment, the composition according to the invention comprises: (A) polypropylene, (B) Formula R2R 2 Si[OSiR2] p [OSiRR 2 ] q OSiR2R 2 (wherein R, R 2 , p and q have the same definition as above, preferably R = methyl group, R2 =H 25 C 12 -NH-[CO-CO]-NH-(CH2)3-, p=150 and q=0, optionally, (C) an inorganic filler; optionally, (D) organic or inorganic fibers; optionally (E) a flame retardant; optionally (F) a biocide; optionally (G) a pigment; optionally (H) an ultraviolet absorber, Optionally, (I) a HALS stabilizer.

[0084] The composition according to the present invention preferably does not contain any further components other than components (A) to (I).

[0085] The individual components of the composition according to the invention may in each case be one type of component or alternatively a mixture of at least two different types of components.

[0086] The composition according to the invention can be prepared by any existing known process, such as mixing the components in any desired order. Prior art mixers or kneaders or extruders can be used for this purpose.

[0087] The present invention further relates to a process for preparing the composition according to the invention by mixing components (A) and (B) and, optionally, further components, preferably components selected from components (C) to (I), in any desired order.

[0088] The process according to the invention can be carried out in the presence or absence of a solvent, with solvent-free preparation being preferred.

[0089] The process according to the invention can be carried out continuously, discontinuously or semi-continuously, but is preferably carried out continuously.

[0090] The process according to the invention is preferably carried out in a continuously operating mixer or kneader or extruder, in which the individual components to be mixed according to the invention are continuously fed by weight or volume to a mixing unit, respectively in pure form or as premixes. Components present in the overall mixture in a proportion of less than 1% by weight are preferably fed as a premix to one of the components present in a larger proportion.

[0091] The temperature at which the process according to the invention is carried out depends mainly on the components used and is known to the person skilled in the art, but is below the specific decomposition temperature of the individual components used. The process according to the invention is preferably carried out at a temperature below 250°C, more preferably at a temperature between 150 and 220°C.

[0092] The process according to the invention is preferably carried out at the pressure of the surrounding atmosphere, i.e. 900-1100 hPa. However, higher pressures can also be employed, in particular depending on the mixing unit used. For example, the pressure in different areas of the mixer or kneader or extruder used is, for example, significantly greater than 1000 hPa.

[0093] In a preferred embodiment of the process according to the invention, component (B) is used in the form of a premix with a part of component (A) and optionally one or more of components (C) to (I), known as a masterbatch. This premix is ​​preferably prepared by mixing components (A) and (B) and optionally one or more of components (C) to (I) at a temperature between 100° C. and 230° C., the mixing being carried out continuously, discontinuously or semi-continuously. For the mixing step, prior art mixers or kneaders or extruders can be used.

[0094] Components (A) and (B) are preferably mixed continuously in a prior art extruder or kneader. The copolymer (B) is present in this premix preferably in an amount of 5% to 40% by weight, more preferably 10% to 30% by weight, particularly preferably 10% to 25% by weight, in each case based on the weight of the premix.

[0095] The premix produced according to the invention is preferably in the form of pellets or powder, but preferably in the form of pellets, which can also be processed into a powder by mechanical grinding or obtained as micropellets via a suitable pelletizing unit.

[0096] In the process according to the invention, the premix thus obtained is then preferably continuously conveyed together with the remainder of component (A) and one or more of the optionally used components (C) to (I) to a heatable mixer, where the components can be added separately or together to the mixer. The individual components are then mixed or homogenized, preferably at temperatures of 150 to 240°C, particularly preferably 180 to 230°C.

[0097] After the mixing step of the individual components, the composition according to the invention is then preferably discharged from the reactor as a hot, highly viscous melt through a nozzle. In a preferred process, the material is cooled by a cooling medium after discharge and then crushed or granulated. Here, the cooling and pelletizing of the material can be achieved simultaneously by underwater pelletizing or after one of them. As a preferred cooling medium, either water or air is used. The preferred methods of pelletizing are underwater pelletizing, air cutting pelletizing, or strand pelletizing. The pellets obtained preferably have a weight of less than 0.5 g, more preferably less than 0.25 g, in particular less than 0.125 g. Preferably, the pellets obtained according to the invention are cylindrical or spherical.

[0098] The pellets thus obtained can be extruded in a subsequent procedure by further thermoplastic processing to form shaped articles, preferably profiles. According to a preferred procedure, the composition according to the invention is continuously conveyed in the form of pellets to a prior art kneader or extruder, where it is heated and plasticized by the influence of temperature and then pressed through a nozzle that defines the desired profile shape. Depending on the design of the nozzle, either solid or hollow profiles can be produced here.

[0099] The invention further relates to molded articles produced according to the invention by extrusion of the composition according to the invention or by processing by an injection molding process.

[0100] In a preferred embodiment, the composition according to the invention is continuously directly extruded through a suitable nozzle in the form of a profile or film which can then be trimmed and / or cut to length, also after cooling.

[0101] The compositions according to the invention can be prepared using prior art mixers or kneaders or extruders.

[0102] The compositions obtained according to the invention are preferably thermoplastic, which means that the temperature at which the loss factor (G'' / G') according to DIN EN ISO 6721-2:2008 assumes a value of 1 is preferably at least 40°C, particularly preferably at least 100°C.

[0103] The mixtures according to the invention can be used wherever mixtures with thermoplastic polymers have also been employed up to now.

[0104] The mixtures according to the invention can be used to produce semi-finished products such as films, pipes, cable claddings, panels, profiles or fibers or to produce three-dimensional molded parts.

[0105] The composition according to the invention has the advantage that it is easy to manufacture.

[0106] When these compositions are continuously processed into semi-finished products, the compositions according to the invention have the advantage that they result in products that exhibit better surface quality, exhibit improved abrasion resistance, have lower surface energy and exhibit improved mechanical properties. Furthermore, these semi-finished products can be extruded at higher speeds. The production of three-dimensional mouldings from the compositions according to the invention has the advantage that they exhibit increased abrasion resistance, the processing steps can be accelerated due to the increased flowability of the material, the adhesion to the mould is reduced and therefore the demolding forces and demolding times can be reduced, thinner and lighter parts can be produced, and the surface quality of the mouldings produced from the mixtures according to the invention is significantly better, making it possible to prevent rheological effects such as "tiger stripes" that occur during the injection moulding process.

[0107] The composition according to the invention has the advantage that it makes it possible to replace a more fluid polymer having worse mechanical properties with a less fluid polymer having better mechanical properties, thereby improving the overall mechanical properties of the composition.

[0108] The use of fillers in the compositions according to the invention has the advantage that the filler content can be increased slightly to improve the property profile without affecting the processability.The mixture according to the invention makes it possible to avoid damage to anisotropic fillers such as fibers, which results in an improved property profile.

[0109] In the examples set forth below, all viscosity data is based on a temperature of 25° C. Unless otherwise noted, the examples that follow are carried out at ambient atmospheric pressure, i.e., about 1000 hPa, at a temperature of 20° C. or the temperature that occurs when the reactants are combined at room temperature without supplemental heating or cooling, and at a relative humidity of about 50%. Additionally, unless otherwise noted, all parts and percentages reported are by weight.

[0110] Reactants PE1: High density polyethylene, commercially available from LyondellBasell, D-Frankfurt under the name "HDPE, Purell GA 7760". PE2: High density polyethylene, commercially available from Borealis Polyolefine, A-Linz under the name "HDPE, BB2581". PP1: Polypropylene homopolymer, commercially available from Borealis Polyolefine, A-Linz under the name "HC205 TF"; Amine 1: Dodecylamine, available under the name "Armeen 12D" from Nouryon, Stenung-sund, Sweden. Amine 2: Cocoamine, a C8-C18 mixture of aliphatic amines, available under the name "Armee CD" from Nouryon, Stenung-sund, Sden. Amine 3: 1-aminooctadecane, commercially available from Sigma-Aldrich under the name "Octadecylamine". Amide 1: cis-13-docosenamide, commercially available from Sigma-Aldrich under the name "Erucamide." Amide 2: N,N'-ethylenebis(stearamide), commercially available from Sigma-Aldrich under the name "N,N'-ethylenebis(stearamide)". Amide 3: A linear, high molecular weight silicone oxamide copolymer prepared according to EP 1963404 B1, Example 16. Silicone 1: Formula HCO-CO-CO-NH-CH-Si(CH)-[OSi(CH)] with number average molecular weight Mn of 11457 g / mol n -OSi(CH3)2-C3H6-NH-CO-CO-OC2H5, an ethyloxamidopropyl terminated polydimethylsiloxane. Silicone 2: Formula HCO-CO-CO-NH-CH-Si(CH)-[OSi(CH)] with number average molecular weight M of 8103 g / mol n -OSi(CH3)2-C3H6-NH-CO-CO-OC2H5, an ethyl oxalamidopropyl terminated polydimethylsiloxane. EXAMPLES

[0111] Example 1 Under a nitrogen atmosphere, 1.146 kg (0.1 mol) of silicone 1 was initially charged into a 2 L three-neck flask and heated to 80° C. with stirring. 37.1 g (0.2 mol) of amine 1 was then added and stirred for 30 minutes, after which the ethanol formed was distilled off at 200 mbar pressure. After stirring for another 30 minutes, the resulting product was isolated as a polymer melt. This resulted in the synthesis of a compound of formula H having a number average molecular weight of 11733 g / mol and a melting point of 28° C. 25 C 12 NH-CO-CO-NH-C3H6-Si(CH3)2-[OSi(CH3)2] n -OSi(CH3)2-C3H6-NH-CO-CO-NHC 12 H 25 As a result, 1,173 g of dodecylaminoxamidopropyl-terminated polydimethylsiloxane (Silicone 3) was obtained.

[0112] Example 2 Under a nitrogen atmosphere, 1.146 kg (0.1 mol) of silicone 1 was initially charged into a 2 L three-neck flask and heated to 80° C. with stirring. 39.7 g (0.2 mol) of amine 2 was then added and after stirring for 30 minutes, the ethanol formed was distilled off under a pressure of 200 mbar. After stirring for another 30 minutes, the resulting product was isolated as a polymer melt. This yielded 1173 g of a cocoaminoxamidopropyl-terminated polydimethylsiloxane (Silicone 4) that was liquid at room temperature and had a number average molecular weight of 11752 g / mol.

[0113] Example 3 Under a nitrogen atmosphere, 1.146 kg (0.1 mol) of silicone 1 was initially charged into a 2 L three-neck flask and heated to 80° C. with stirring. 53.9 g (0.2 mol) of amine 3 was then added and stirred for 30 minutes, after which the ethanol formed was distilled off at 200 mbar pressure. After stirring for another 30 minutes, the resulting product was isolated as a polymer melt. This yielded 1175 g of octadecylaminooxamidopropyl-terminated polydimethylsiloxane (Silicone 5) having a number average molecular weight of 11932 g / mol.

[0114] Example 4 Under a nitrogen atmosphere, 0.810 kg (0.1 mol) of silicone 2 was initially charged into a 2 L three-neck flask and heated to 60° C. with stirring. 37.1 g (0.2 mol) of amine 1 was then added and stirred for 30 minutes, after which the ethanol formed was distilled off at 200 mbar pressure. After stirring for another 30 minutes, the resulting product was isolated as a polymer melt. This resulted in the synthesis of a compound of formula H having a number average molecular weight of 8346 g / mol and a melting point of 28° C. 25 C 12 NH-CO-CO-NH-C3H6-Si(CH3)2-[OSi(CH3)2] n -OSi(CH3)2-C3H6-NH-CO-CO-NHC 12 H 25 As a result, 837 g of dodecylaminoxamidopropyl-terminated polydimethylsiloxane (Silicone 6) was obtained.

[0115] Example 5 Under a nitrogen atmosphere, 0.810 kg (0.1 mol) of silicone 2 was initially charged into a 2 L three-neck flask and heated to 60° C. with stirring. 53.9 g (0.2 mol) of amine 2 was then added and stirred for 30 minutes, after which the ethanol formed was distilled off at 200 mbar pressure. After stirring for another 30 minutes, the resulting product was isolated as a polymer melt. This resulted in the synthesis of a compound of formula H with a number average molecular weight of 8488 g / mol. 37 C 18NH-CO-CO-NH-C3H6-Si(CH3)2-[OSi(CH3)2] n -OSi(CH3)2-C3H6-NH-CO-CO-NHC 18 H 37 As a result, 842 g of cocoaminoxamidopropyl-terminated polydimethylsiloxane (Silicone 7) was obtained.

[0116] Examples 6 to 10 Each of the silicones 3 to 7 prepared above was homogeneously mixed with polyethylene PE1 in an amount specified in Table 1 at room temperature, and the total amount of each mixture was 1000 g.

[0117] The mixture was then compounded in each case in a counter-rotating twin-screw extruder (Collin) at a temperature of 195° C. The temperature in the feed zone (zone 1) was 95° C., increased to 190° C. in zones 2 and 3, and further increased to 195° C. in zones 4 and 5. Zone 6 (nozzle) was heated to 190° C. The mixture was extruded as a strand, which was then pelletized. The rotation speed of the screws was 50 rpm. The discharge rate was about 1.5 kg / h. The melt volume rate (MVR) of the polymer mixtures thus obtained was then determined in accordance with DIN ISO 1133 using a Gottfert MFI tester (MI II) at a temperature of 175 °C, a load weight of 2.16 kg, a heating time of 5 min and a nozzle diameter of 2 mm. In each case, three measured values ​​were determined and averaged. The results are shown in Table 1.

[0118] Example 11 10 g of Silicone 3 prepared above was mixed uniformly with 990 g of Polyethylene PE1 defined in Table 1 at room temperature to make the total amount of the mixture 1000 g. The mixture was then compounded in each case in a counter-rotating twin-screw extruder (Collin) at a temperature of 195° C. The temperature in the feed zone (zone 1) was 95° C., increased to 190° C. in zones 2 and 3, and further increased to 195° C. in zones 4 and 5. Zone 6 (nozzle) was heated to 190° C. The mixture was extruded as a strand, which was then pelletized. The rotation speed of the screws was 50 rpm. The discharge rate was about 1.5 kg / h. The melt volume rate (MVR) of the polymer mixture thus obtained was then measured according to DIN ISO 1133 using a Gottfert MFI tester (MI II) at a temperature of 175 °C, a load weight of 2.16 kg, a heating time of 5 minutes and a nozzle diameter of 2 mm. Three measured values ​​were determined and averaged. The results are shown in Table 1.

[0119] [Table 1]

[0120] Comparative Example C1 The procedure described in Examples 6-10 was repeated except that none of Silicones 3-7 was used. The results are shown in Table 2.

[0121] Comparative examples C2~C4 The procedure described in Examples 6-10 is repeated except that 20 g of each of the amides specified in Table 2 are used in place of Silicones 3-7. The results are shown in Table 2.

[0122] [Table 2]

[0123] It can be seen that the end-functionalized silicones 3-7 in the mixtures of Examples 6-11 have significantly higher flow properties compared to the linear high molecular weight silicone oxamide copolymers of the prior art. The compositions according to the invention are also more effective than or as effective as standard amide-based processing aids such as eurucamide or EBS (ethylene bis stearamide). However, due to their low molecular weight characteristics, they have a strong tendency to migrate to the surface of plastics, especially at high loads, which is often undesirable.

[0124] Examples 12 to 17 Each of the silicones 3 to 7 prepared above was homogeneously mixed with the amount of polyethylene PE2 specified in Table 3 at room temperature until the total amount of each mixture was 1000 g. The mixture was then compounded in a counter-rotating twin screw extruder (Collin) at a temperature of 195°C. The temperature in the feed zone (zone 1) was 95°C, increasing to 190°C in zones 2 and 3, and further increasing to 195°C in zones 4 and 5. Zone 6 (nozzle) was heated to 195°C. The mixture was extruded as a strand, which was pelletized. The screw rotation speed was 50 rpm. The discharge rate was about 1.5 kg / h. The melt volume rate (MVR) of the polymer mixtures thus obtained was then measured in accordance with DIN ISO 1133 using a Gottfert MFI tester (MI II) at a temperature of 190 °C, a load weight of 10 kg, a heating time of 5 min and a nozzle diameter of 2 mm. In each case, three measured values ​​were determined and averaged. The results are shown in Table 3.

[0125] Comparative example C5 The procedures described in Examples 12-17 were repeated, except that none of Silicones 3-7 were used, and the results are shown in Table 3.

[0126] [Table 3]

[0127] Examples 18-23 Each of the silicones 3 to 7 prepared above was mixed uniformly at room temperature with the amount of polypropylene homopolymer PP1 specified in Table 4, until the total amount of each mixture was 1000 g.

[0128] The mixture was then compounded in a counter-rotating twin screw extruder (Collin) at a temperature of 210° C. The temperature in the feed zone (zone 1) was 95° C., increased to 190° C. in zones 2 and 3, and further increased to 205° C. in zones 4 and 5. Zone 6 (nozzle) was heated to 200° C. The mixture was extruded as strands, which were pelletized. The screw rotation speed was 50 rpm. The discharge rate was about 1.5 kg / h.

[0129] The melt volume rate (MVR) of the polymer mixtures thus obtained was then determined in accordance with DIN ISO 1133 using a Gottfert MFI tester (MI II) at a temperature of 230° C., a load weight of 2.16 kg, a heating time of 5 min and a nozzle diameter of 2 mm. In each case, three measured values ​​were determined and averaged. The results are shown in Table 4.

[0130] Comparative example C6 The procedure described in Examples 18-23 was repeated except that none of Silicones 3-7 was used. The results are shown in Table 4.

[0131] [Table 4]

Claims

1. (A) a thermoplastic polymer, and (B) 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) {During the ceremony, R, which may be the same or different, is a monovalent hydrocarbon radical having 1 to 6 carbon atoms with SiC bonds; R １ are the same or different and are a hydrogen atom or an optionally substituted monovalent hydrocarbon radical, R ２ is represented by the general formula: R ３ -X-[CO-(CO) ｎ ]-X-R ４ - (II) (In the formula, X may be the same or different and is -NR ｘ - and R ３ are the same or different, optionally substituted monovalent hydrocarbon radicals having at least 6 carbon atoms; R ４ is an optionally substituted divalent hydrocarbon radical having 1 to 40 carbon atoms, each carbon atom being an oxygen atom or -NR ｚ may be substituted with -, R ｘ are the same or different and are hydrogen atoms or optionally substituted monovalent hydrocarbon radicals having 1 to 20 carbon atoms, each of which may be substituted with an oxygen atom; R ｚ are the same or different and are hydrogen atoms or optionally substituted monovalent hydrocarbon radicals having 1 to 20 carbon atoms, each of which may be substituted with an oxygen atom; n is 1) is a SiC bond unit of 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; r is 0 or an integer from 1 to 100; However, a+b is ≦3 and at least one R ２ group is present. At least one organosilicon compound of A composition comprising:

2. 2. The composition of claim 1, wherein component (A) is a polyethylene, polypropylene, polyamide, polyethylene terephthalate, or polybutylene terephthalate.

3. 3. The composition according to claim 1, wherein the organosilicon compound of formula (I) has a number average molecular weight Mn of from 1000 g / mol to 35000 g / mol.

4. The composition according to any one of claims 1 to 3, characterized in that component (B) is used in an amount of 0.05 parts by weight to 10 parts by weight, based on 100 parts by weight of component (A).

5. The composition according to any one of claims 1 to 4, characterized in that the composition further comprises, in addition to components (A) and (B), a material selected from inorganic fillers (C), organic or inorganic fibers (D), flame retardants (E), biocides (F), pigments (G), UV absorbers (H), and HALS stabilizers (I).

6. A process for preparing a composition according to any one of claims 1 to 5 by mixing components (A) and (B) and optionally further components in any desired order.

7. A molded article produced by extrusion of a composition according to any one of claims 1 to 5, or a molded article produced by the method according to claim 6 by processing by an injection molding process.

8. 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) {During the ceremony, R, which may be the same or different, is a monovalent hydrocarbon radical having 1 to 6 carbon atoms with SiC bonds; R １ are the same or different and are a hydrogen atom or an optionally substituted monovalent hydrocarbon radical, R ２ is represented by the general formula: R ３ -X-[CO-CO]-X-R ４ - (II) (In the formula, X may be the same or different and is -NR ｘ - and R ３ are the same or different, optionally substituted monovalent hydrocarbon radicals having at least 6 carbon atoms; R ４ is an optionally substituted divalent hydrocarbon radical having 1 to 40 carbon atoms, each carbon atom being an oxygen atom or -NR ｚ may be substituted with -, R ｘ are the same or different and are hydrogen atoms or optionally substituted monovalent hydrocarbon radicals having 1 to 20 carbon atoms, each of which may be substituted with an oxygen atom; R ｚ may be the same or different and are hydrogen atoms or optionally substituted monovalent hydrocarbon radicals having 1 to 20 carbon atoms, each of which may be substituted with an oxygen atom. is a SiC bond unit of a is 0, 1, or 2; b is 0 or 1; p is an integer from 1 to 1000; q is 0 or an integer from 1 to 100; r is 0 or an integer from 1 to 100; However, a+b is ≦3 and at least one R ２ group is present. Organosilicon compounds.

9. General formula: R ３－ａ－ｂ (OR １ ) ａ R １１ ｂ Si[OSiR ２ ] ｐ [OSiRR １１ ] ｑ [OSiR １１ ２ ] ｒ OSiR ３－ａ－ｂ (OR １ ) ａ R １１ ｂ (I’) {During the ceremony, R, R １ , a, b, p, q and r have the definitions given above; R １１ is represented by the general formula: R １０ -O-[CO-CO]-NR ｘ -R ４ - (II') (In the formula, R ４ , R ｘ and n each have the definition given above. R １０ is a hydrogen atom or an optionally substituted monovalent hydrocarbon radical, optionally interrupted by heteroatoms; However, a+b is ≦3 and at least one R １１ group is present) is a SiC bond unit.} of organosilicon compounds General formula: R ３ -NR ｘ -H (IV) (In the formula, R ３ and R ｘ has the definition given above.) with an organic compound of formula (I) to produce an oxamide-functional siloxane.

10. 10. The method according to claim 9, wherein the compound of formula (IV) is a primary amine.

Images