PERFLUOROPHENYL AZIDE-CONTAINING SILOXANE OLIGOMER MIXTURES

Abstract

A perfluorophenyl azide containing siloxane oligomer mixture along with products made therefrom, uses for the same, methods for preparing and methods for curing the same.

Claims

1-15. (canceled)

16. A PFPA-containing siloxane oligomer mixture, comprising: wherein the PFPA-containing siloxane oligomer mixture is selected from compounds of average formula (I)
[SiO.sub.4/2].sub.a[RSiO.sub.3/2].sub.b[R.sup.1SiO.sub.3/2].sub.b′[R.sub.2SiO.sub.2/2].sub.c[R.sup.1.sub.2SiO.sub.2/2].sub.c′[RR.sup.1SiO.sub.2/2].sub.c″[R.sub.3SiO.sub.1/2].sub.d [R.sub.2R.sup.1SiO.sub.1/2].sub.d′[RR.sup.1.sub.2SiO.sub.1/2].sub.d″[R.sup.1.sub.3SiO.sub.1/2].sub.d′″  (I) wherein the indices a, b, b′, c, c′, c″, d, d′, d″ and d′ specify the average content of the respective siloxane units in the mixture and are each independently a number in the range of 0 to 300, with the proviso that the sum total of all indices is in a range from 3 to 3500 and on average at least 2 R radicals are present; wherein the radicals R.sup.1 are each independently selected from the group consisting of (i) hydrogen, (ii) halogen, (iii) C.sub.1-C.sub.20-hydrocarbon radical, (iv) hydroxyl radical and (v) C.sub.1-C.sub.20-hydrocarbonoxy radical; wherein the radicals R are identical and refer to a radical of the formula ##STR00002## wherein the radical X is selected from (i) —O— or (ii) —NH—; and wherein the index n (i) is a value in the range from 0 to 10 when X=—O—, and (ii) is a value in the range from 1 to 10 when X=—NH—.

17. The mixture of claim 16, wherein in the formula (I) the radicals R.sup.1 are each independently selected from the group consisting of (i) hydrogen radical, (ii) methyl radical, (iii) ethyl radical, (iv) phenyl radical, (v) vinyl radical, (vi) hydroxyl radical, and (vii) C.sub.1-C.sub.20-alkoxy radical.

18. The mixture of claim 16, wherein in the radicals R in formula (I), the radicals X are each independently selected from (i) —O— or (ii) —NH—, in which the index n (i) has a value in the range of 0 to 6 when X=—O—, and (ii) has a value in the range of 1 to 6 when X=—NH—.

19. The mixture of claim 16, wherein in the formula (I) the indices a, b, b′, c, c′, c″, d, d′, d″ and d′″ each independently have the following definitions: wherein a=a number in the range from 0 to 250; wherein b=a number in the range from 0 to 50; wherein b′=a number in the range from 1 to 250; wherein c=a number in the range from 1 to 280; wherein c′=a number in the range from 1 to 280; wherein c″=a number in the range from 1 to 280; wherein d=a number in the range from 0 to 250; wherein d′=a number in the range from 0 to 250; wherein d″=a number in the range from 0 to 250; wherein d′″=a number in the range from 0 to 250; and wherein the sum total of all indices is in the range of 3 to 3000 and on average at least 2 and at most 20 R radicals are present.

20. The mixture of claim 16, wherein the mixture is used as adhesion promoters.

21. A mixture, comprising: a) at least one PFPA-containing siloxane oligomer mixture, wherein the PFPA-containing siloxane oligomer mixture is selected from compounds of average formula (I)
[SiO.sub.4/2].sub.a[RSiO.sub.3/2].sub.b[R.sup.1SiO.sub.3/2].sub.b′[R.sub.2SiO.sub.2/2].sub.c[R.sup.1.sub.2SiO.sub.2/2].sub.c′[RR.sup.1SiO.sub.2/2].sub.c″[R.sub.3SiO.sub.1/2].sub.d [R.sub.2R.sup.1SiO.sub.1/2].sub.d′[RR.sup.1.sub.2SiO.sub.1/2].sub.d″[R.sup.1.sub.3SiO.sub.1/2].sub.d′″  (i), wherein the indices a, b, b′, c, c′, c″, d, d′, d″ and d′ specify the average content of the respective siloxane units in the mixture and are each independently a number in the range of 0 to 300, with the proviso that the sum total of all indices is in a range from 3 to 3500 and on average at least 2 R radicals are present; wherein the radicals R.sup.1 are each independently selected from the group consisting of (i) hydrogen, (ii) halogen, (iii) C.sub.1-C.sub.20-hydrocarbon radical, (iv) hydroxyl radical and (v) C.sub.1-C.sub.20-hydrocarbonoxy radical; wherein the radicals R are identical and refer to a radical of the formula ##STR00003## wherein the radical X is selected from (i) —O— or (ii) —NH—; and wherein the index n (i) is a value in the range from 0 to 10 when X=—O—, and (ii) is a value in the range from 1 to 10 when X=—NH—; and b) at least one natural or synthetic polymer selected from the group consisting of b1) addition-crosslinking silicone compositions; or b2) condensation-crosslinking silicone compositions; or b3) hybrid materials/STP; or b4) inorganic and/or organic polymers.

22. The mixture of claim 21, wherein the mixture is a molding and a weakly polar to non-polar substrate.

23. The mixture of claim 22, wherein the substrate is selected from synthetic hydrocarbon polymers, such as polyolefins of mono- or polyenes, polyhaloolefins, polyethers, polyvinyl chloride, polyvinylidene difluoride, polycarbonates, polyesters, and copolymers of the corresponding monomers (e.g. EPDM or acrylonitrile-butadiene-styrene (ABS)) and any polymer blends of the polymers and/or copolymers mentioned above.

24. The mixture of claim 21, wherein the mixture is a self-adhesive silicone composition coating materials for weakly polar to non-polar substrates.

25. The mixture of claim 24, wherein the substrate is selected from synthetic hydrocarbon polymers, such as polyolefins of mono- or polyenes, polyhaloolefins, polyethers, polyvinyl chloride, polyvinylidene difluoride, polycarbonates, polyesters, and copolymers of the corresponding monomers (e.g. EPDM or acrylonitrile-butadiene-styrene (ABS)) and any polymer blends of the polymers and/or copolymers mentioned above.

26. A method for preparing a mixture, comprising: providing at least one PFPA-containing siloxane oligomer mixture, wherein the PFPA-containing siloxane oligomer mixture is selected from compounds of average formula (I)
[SiO.sub.4/2].sub.a[RSiO.sub.3/2].sub.b[R.sup.1SiO.sub.3/2].sub.b′[R.sub.2SiO.sub.2/2].sub.c[R.sup.1.sub.2SiO.sub.2/2].sub.c′[RR.sup.1SiO.sub.2/2].sub.c″[R.sub.3SiO.sub.1/2].sub.d [R.sub.2R.sup.1SiO.sub.1/2].sub.d′[RR.sup.1.sub.2SiO.sub.1/2].sub.d″[R.sup.1.sub.3SiO.sub.1/2].sub.d′″  (i), wherein the indices a, b, b′, c, c′, c″, d, d′, d″ and d′″ specify the average content of the respective siloxane units in the mixture and are each independently a number in the range of 0 to 300, with the proviso that the sum total of all indices is in a range from 3 to 3500 and on average at least 2 R radicals are present; wherein the radicals R.sup.1 are each independently selected from the group consisting of (i) hydrogen, (ii) halogen, (iii) C.sub.1-C.sub.20-hydrocarbon radical, (iv) hydroxyl radical and (v) C.sub.1-C.sub.20-hydrocarbonoxy radical; wherein the radicals R are identical and refer to a radical of the formula ##STR00004## wherein the radical X is selected from (i) —O— or (ii) —NH—; and wherein the index n (i) is a value in the range from 0 to 10 when X=—O—, and (ii) is a value in the range from 1 to 10 when X=—NH—; and curing the mixture by thermal and/or photochemical activation.

27. The method of claim 26, wherein the curing takes place by a one-stage or multi-stage thermal activation in the temperature range of 0° C. to 200° C.

28. The method of claim 27, wherein the thermal activation takes place in a temperature range of 10° C. to 180° C.

29. The method of claim 27, wherein the curing is effected by a two-stage thermal activation, comprising the following steps: a) thermal activation at a temperature T1 in a temperature range of 0° C. to 140° C.; and b) thermal activation at a temperature T2 in a temperature range of 120° C. to 180° C.; wherein it must apply that: T1<T2.

30. The method of claim 26, wherein the curing is effected by a one-stage or multi-stage photochemical activation with actinic radiation in the wavelength range of 800 nm to 50 nm.

Description

EXAMPLES

[0055] Instruments:

[0056] XPS

[0057] XPS analysis was carried out using a PhI5000 VersaProbe spectrometer (ULVAC-PHI INC.) with a 180° spherical capacitor energy analyzer and a multichannel detector (16 channels). The spectra were recorded at a base pressure of 5*10.sup.−8 Pa with focussed scanning using a monochromatic Al-Ka source (1486.6 eV) with a spot size of 200 μm and 47.6 W. The instrument was operated in the FAT analyzer mode, in which the electrons were emitted at an angle of 45° to the sample surface. The pass energy used for the measuring scans was 187.85 eV for overview scans and 46.95 eV for detailed spectra.

[0058] Charge neutralization was effected using a cold cathode electron beam source (1.2 eV) and very low energy Ar+ ions (10 eV) during the whole analysis.

[0059] The data were analyzed using the CasaXPS [Version 2.3.15, www.casaxps.com] program. The signals were integrated by the Shirley background subtraction method. Sensitivity factors were calculated with the aid of published ionization cross-sections (Scofield, J. H. J. J. Elec. Spec. Rel. Phen. 1976, 8, 129.) and corrected for attenuation, transfer function of the instrument and sample to analyzer angle. Consequently, the amounts measured are stated as apparent normalized atomic concentration, in which the precision under the selected conditions is ca. ±10%.

[0060] NMR

[0061] Bruker Avance III HD 400 Spectrometer with BBO probe head; 150 mg of methylpolysiloxane mixtures in 500 μl of CDCl.sub.3.

[0062] UV Lamp

[0063] UV radiometer UVPAD from Opsytec Dr. Gröbel (spectral range: 200-440 nm±5 nm; light intensity:2-5000 mW/cm.sup.2)

[0064] Chemicals:

[0065] WACKER® FLUID NH15D: double (3-aminopropyldimethylsilyloxy)-end-capped PDM-siloxane having an intermediate chain length of average 15, a viscosity between 10 and 20 mm.sup.2/s at a mean molar mass of ca. 1100 g/mol. Commercially available from Wacker Chemie AG.

[0066] WACKER® FLUID SLM92512: double (3-aminopropyldimethylsilyloxy)-end-capped PDM-siloxane having an intermediate chain length of average 200, a viscosity between 300 mm.sup.2/s and 400 mm.sup.2/s at a mean molar mass of ca. 15 000 g/mol. Available on request from Wacker Chemie AG.

[0067] PFPA-NHS: N-Hydroxysuccinimide-functionalized perfluorophenyl azide, commercially available, for example from abcr GmbH or TCI Chemicals Ltd. (CAS No.

[0068] ELASTOSIL® RT604 A/B: Room temperature crosslinking silicone rubber (RTV-2). Commercially available from Wacker Chemie AG.

1) Preparation of PFPA-Modified Siloxanes

Example 1: Synthesis of (PFPA).SUB.2.-PDMS.SUB.15

[0069] WACKER® FLUID NH15D (1.54 g, 1.40 mmol) is dissolved in 10 mL of THF at room temperature. PFPA-NHS (0.715 g, 3.08 mmol, 2.2 equivalents based on the amine content of the siloxane) and triethylamine (311 mg, 3.08 mmol) are added to the solution and stirred at room temperature. After 1 hour the formation of a colorless precipitate is observed, the mixture being further stirred overnight. Subsequently, all volatile constituents are removed to dryness under reduced pressure, the residue is taken up in diethyl ether (30 mL) and treated as follows: (i) extraction twice with 2N hydrochloric acid, (ii) single extraction with 1N aqueous sodium hydroxide solution and (iii) washed twice with saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and the solvent is removed under vacuum (10.sup.−2 mbar).

[0070] A yellow oil is obtained (yield: 1.882 g, 87%)

[0071] 1H-NMR (400.1 MHz; CDCl3): δ=0.09 ppm (90H; m, Si—CH3), 0.61 ppm (4H, m, Si-CH2-CH2-CH2—NH-PFPA), 1.67 ppm (4H, m, Si-CH2-CH2-CH2—NH-PFPA), 3.46 ppm (4H, m, Si-CH2-CH2-CH2—NH-PFPA), 6.01 ppm (1H, —NH-PFPA). 19F-NMR (376.5 MHz; CDCl3): δ=141.0, 150.5 ppm.

Example 2: Synthesis of (PFPA).SUB.2.-PDMS.SUB.202

[0072] WACKER® FLUID SLM92512 (1.57 g, 0.104 mmol) is dissolved in 10 mL of THF at room temperature. PFPA-NHS (77.5 mg, 0.233 mmol, 2.2 equivalents based on the amine content of the siloxane) and triethylamine (23.2 mg, 0.229 mmol) are added to the solution and stirred at room temperature overnight. Subsequently, all volatile constituents are removed to dryness under reduced pressure, the residue is taken up in diethyl ether (30 mL) and treated as follows: (i) extraction twice with 2N hydrochloric acid, (ii) single extraction with 1N aqueous sodium hydroxide solution and (iii) washed twice with saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and the solvent is removed under vacuum (2-10 mbar). A yellow oil is obtained (yield: 1.6 g, 100%).

[0073] 1H-NMR (400.1 MHz; CDCl3): δ=0.09 ppm (1750H; m, Si—CH3), 0.61 ppm (4H, m, Si-CH2-CH2-CH2—NH-PFPA), 1.67 ppm (4H, m, Si-CH2-CH2-CH2—NH-PFPA), 3.46 ppm (4H, m, Si-CH2-CH2-CH2—NH-PFPA), 6.01 ppm (1H, —NH-PFPA). 19F-NMR (376.5 MHz; CDCl3): δ=140.9, 150.5 ppm.

2) Investigation of the Adhesion Properties on PP, PC, PET, PTFE, PVDF

Example 3: Coating Process and Surface Analysis

[0074] Selected substrate materials—PP, PC, PET, PTFE, and PVDF—are provided as 1×1 cm sized plates and are cleaned three times with isopropanol in an ultrasound bath for 20 minutes. In the case of plasma pre-treatment, the selected material is exposed to oxygen plasma for 5 minutes. The coating is carried out by means of spin coating using n-hexane solutions (concentration 5 mg/mL) of the respective modified silicone (PFPA.sub.2—NH15D) or of the unmodified silicone (WACKER® FLUID NH15D). Layer thicknesses between 40 and 55 nm are produced. The reaction (crosslinking/curing/etc.) is triggered either by UV-C treatment (10 minutes 3.4 mW/cm.sup.2) or by heat treatment (2 hours at 140° C.). Each sample is then extracted three times with n-hexane (PC) or ethyl acetate (PP, PET, PTFE, PVDF) and dried in a gas stream. The elemental composition of the surface is investigated by XPS analysis and the theoretical element contents (C, N, O, F, Si) to be expected are compared with the experimental. The results are shown in Tables 1-5.

[0075] Table 1: XPS analysis PP, Table 2: XPS analysis PET, Table 3: XPS analysis PC,

[0076] Table 4: XPS analysis PTFE, Table 5: XPS analysis PVDF

TABLE-US-00001 TABLE 1 XPS Analysis of polypropylene samples. a) NH15D and PFPA-modified NH15D a) WACKER ® FLUID NH15D b) PFPA.sub.2-NH15D Composition theoret. Composition PP blank Batch: 1 2 3 proportion 4 5 6 theoret. proportion Plasma pre-treatment x x Temperature activation x x UV activation x X C 75.8 99.1 99.4 48.4 99.4 66.4 56.7 52.1 99.6 83.9 N 2.2 0 0 3.2 0 2.5 3 4.2 0 1.1 O 15.8 0.6 0.6 24.2 0.5 15.2 19.3 17.7 0.4 14.8 F 0 0 0 0 0 2.7 3 8.3 0 0 Si 6.3 0.3 0 24.2 0.1 13.2 18 17.7 0 0.2 Total 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 Evaluation of the coating − − − − + + b)SLM92512 and PFPA-modified SLM92512 a) WACKER ® FLUID SLM92512 b) PFPA.sub.2-SLM92512 Composition theoret. Composition PP blank Batch: 7 8 9 proportion 10 11 12 theoret. proportion Plasma pre-treatment x x x x x x x Temperature activation x x UV activation x X C 71.4 67.8 59.5 49.9 77.1 63.4 55.6 50.2 99.6 83.9 N 1.9 1.4 0.3 0.3 1.1 0.9 0.5 0.5 0 1.1 O 18.4 20.1 20.8 24.9 17.8 21.3 22.3 24.2 0.4 14.8 F 0 0 0 0.0 0 0.3 0.3 0.9 0 0 Si 8.3 10.7 19.4 24.9 4.0 14.1 21.3 24.2 0 0.2 Total 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 Evaluation of the coating − − − − − +

TABLE-US-00002 TABLE 2 XPS Analysis of polyethylene terephthalate samples. a) NH15D and PFPA-modified NH15D a) WACKER ® FLUID NH15D b) PFPA.sub.2-NH15D Composition theoret. Composition PET blank Batch: 13 14 15 proportion 16 17 18 theoret. proportion Plasma pre-treatment x x x Temperature activation x x UV activation x x C 62.7 54.9 58.3 48.4 61.8 55.4 54.6 52.1 67 N 2.2 1.8 2.1 3.2 2.1 3 3.6 4.2 1.2 O 26.4 21.9 24.3 24.2 27.9 19.6 20.5 17.7 31.4 F 0 0 0 0 0.4 3.6 3.1 8.3 0 Si 8.7 21.4 15.3 24.2 7.8 18.4 18.2 17.7 0.4 Total 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 Evaluation of the coating − − − − + + b)SLM92512 and PFPA-modified SLM92512 a) WACKER ® FLUID SLM92512 b) PFPA.sub.2-SLM92512 Composition theoret. Composition PET blank Batch: 19 20 21 proportion 22 23 24 theoret. proportion Plasma pre-treatment x x x x x x Temperature activation x x UV activation x X C 59.2 57.1 51.1 49.9 60.2 52.9 51.3 50.2 67 N 1.5 1.0 0 0.3 1.1 0* 0* 0.5 1.2 O 28.5 28.4 23.7 24.9 30.9 23.8 23.3 24.2 31.4 F 0 0 0 0.0 0 0.5 0.5 0.9 0 Si 10.8 13.5 25.2 24.9 7.7 22.8 24.9 24.2 0.4 Total 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 Evaluation of the coating − − − − + + *nitrogen proportion in higher molecular weight siloxane too low for error-free detection

TABLE-US-00003 TABLE 3 XPS analysis of polycarbonate samples (treated according to example 3). a) NH15D and PFPA-modified NH15D a) WACKER ® FLUID NH15D b) PFPA.sub.2-NH15D Composition theoret. Composition PC blank Batch: 25 26 27 proportion 28 29 30 theoret. proportion Plasma pre-treatment x x x Temperature activation UV activation x x x C 61.9 58.5 58.5 48.4 85.7 58.2 52.1 90.3 73.1 N 3.1 2.5 2.5 3.2 0.3 2.9 4.2 0.9 1.6 O 21.8 21.5 21.5 24.2 13.4 19.3 17.7 8.8 25.3 F 0 0 0 0 0.2 3 8.3 0 0 Si 13.2 17.5 17.5 24.2 0.4 16.6 17.7 0 0 Total 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 Evaluation of the coating − − − − + b)SLM92512 and PFPA-modified SLM92512 a) WACKER ® FLUID SLM92512 b) PFPA.sub.2-SLM92512 Composition theoret. Composition PC blank Batch: 31 32 proportion 33 34 theoret. proportion Plasma pre-treatment x x x x x Temperature activation UV activation x X C 67.2 61.0 73.1 67.0 49.5 50.2 90.3 73.1 N 1.0 1.4 1.6 1.7 0* 0.5 0.9 1.6 O 24.4 24.8 25.3 25.1 25.2 24.2 8.8 25.3 F 0 0 0 0 0* 0.9 0 0 Si 10.4 12.8 0 6.5 25.3 24.2 0 0 Total 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 Evaluation of the coating − − − + *proportion in the higher molecular weight siloxane too low for error-free detection; no thermal activation possible since polycarbonate is dimensionally stable only up to 125° C. and also has a glass transition at 150° C.

TABLE-US-00004 TABLE 4 XPS Analysis of polytetrafluoroethene samples. a) WACKER ® FLUID NH15D b) PFPA.sub.2-NH15D PTFE Composition theoret. Composition blank Batch: 35 36 37 proportion 38 39 40 theoret. proportion Plasma pre-treatment x Temperature activation x UV activation x x C — — 37.3 48.4 38.3 38.5 38.6 52.1 39.5 N — — 0 3.2 0 0 0 4.2 0 O — — 0 24.2 0 1.5 3.1 17.7 0 F — — 62.7 0 61.7 60 56.1 8.3 60.5 Si — — 0 24.2 0 0 2.2 17.7 0 Total — — 100.0 100.0 100.0 100.0 100.0 100.0 100.0 Evaluation of the coating — — — — — —

TABLE-US-00005 TABLE 5 XPS Analysis of polyvinylidene difluoride samples. a) WACKER ® FLUID NH15D b) PFPA.sub.2-NH15D PVDF Composition theoret. Composition blank Batch: 41 42 43 proportion 44 45 46 theoret. proportion Plasma pre-treatment Temperature activation x UV activation x C 51.7 53.5 52.8 48.4 51.8 54.5 52.8 52.1 50 N 1.1 1.8 1.3 3.2 0.6 1.8 3.6 4.2 0.4 O 13.0 22.5 14.0 24.2 8.5 14.0 21.5 17.7 7.7 F 27.8 0.5 24.9 0 36.5 22.4 3.9 8.3 39.8 Si (Silicone) 4.5 21.7 5.3 24.2 1.3 5.8 18.2 17.7 0 Si (SiO.sub.2 filler in PVDF) 1.9 0.0 1.8 1.3 1.5 0 0.0 1.7 Total 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 Evaluation of the coating − − − − − + PVDF comprises SiO.sub.2 as filler (binding energy according to XPS: 103.7+/−0.1 eV); signal of the modified silicone at 1022.4(+/−0.1) eV according to XPS. This explains the oxygen- and silicon-containing composition compared to theory of 50% C and 50% F. Explanation of Tables 1-5, evaluation of the adhesion between substrate and coating material: no reliable coating detectable: −; coating detectable: +

3) Investigation of the Adhesion Properties of PFPA-Containing Siloxane Oligomer (PFPA).SUB.2.-(NH15D) in Thermal Crosslinking RTV-2 Compositions (Elastosil® RT604 A/B)

[0077] To produce the RTV-2 silicone compositions, mixture A and B are mixed at a 1:1 mass ratio (for example using a Speedmixer from Hausschild).

[0078] a) for the additive, 5% by weight of the PFPA-containing siloxane oligomer (PFPA).sub.2-(NH15D) is added and mixed by hand or using a Speedmixer.

[0079] b) The polypropylene test pieces are primed with a 10% by weight solution of the PFPA-containing siloxane oligomer (PFPA).sub.2-(NH15D) in ethyl acetate, which evaporates rapidly at room temperature. The amounts used are found in Table 6 below, likewise all crosslinking conditions.

TABLE-US-00006 TABLE 6 Investigation of the adhesion of an RTV-2 silicone elastomer with and without addition of the PFPA-containing siloxane oligomer (PFPA).sub.2-(NH15D) Application of (PFPA).sub.2(NH15D) Batch: in the RTV-2 system Crosslinking-/activation conditions Result Reference 47 RTV-2: ELASTOSIL ® RT604 1 h at 80° C. ○ 48 RTV-2: ELASTOSIL ® RT604 1 h at 140° C. ○ a) Additive 49 5% by weight additive 1 h at 140° C. ○ 50 5% by weight additive 1) 20 min at 80° C., 2) 40 min at 140° C. + b) Priming 51 50 μL (10% by weight in EtOAc) 1) 80° C. (vacuum), 2) 1 h at 140° C. + 52 50 μL (10% by weight in EtOAc) 1) 80° C. (vacuum), 2) 1 h at 80° C., + 3) 1 h at 140° C. 53 50 μL (10% by weight in EtOAc) 1) 80° C. (vacuum), 2) 1 h at 80° C., + 3) 2 × 10 min UV-C 54 100 μL (10% by weight in EtOAc) 1) 80° C. (vacuum), 2) 1 h at 80° C., + 3) 1 h at 140° C. 55 100 μL (10% by weight in EtOAc) 1) 80° C. (vacuum), 2) 1 h at 80° C., + 3) 2 × 10 min UV-C Indices for evaluating the adhesion between silicone elastomer and polypropylene compared to the silicone elastomer without PFPA-containing siloxane oilgomer as adhesion promoter: no adhesion = ○; improved adhesion = +