URETHANE METHACRYLATE COMPOUNDS AND USE THEREOF

Abstract

Low-viscosity urethane methacrylate compounds are used as a backbone resin in reactive resins. In particular, the compounds are for lowering the viscosity of reactive resins containing such mixtures and thus the extrusion forces of reactive resin components produced therefrom and also for increasing the performance of reactive resins and reactive resin components produced therefrom containing such compounds. Furthermore, said compounds and their reactive resin components are used for construction purposes, in particular for chemical fastening.

Claims

1: A compound of general formula (I) ##STR00014## in which B is an aromatic hydrocarbon group, and each R.sub.1, independently of one another, is a branched or linear aliphatic C.sub.1-C.sub.15 alkylene group.

2: The compound according to claim 1, wherein B is an aromatic C.sub.6-C.sub.20 hydrocarbon group.

3: The compound according to claim 2, wherein B contains one or two benzene rings, which optionally are substituted.

4: The compound according to claim 1, wherein R.sub.1 is a C.sub.2- or C.sub.3-alkylene group.

5: A method for production of a reactive resin or of a reactive-resin component for construction purposes, the method comprising: incorporating the compound according to claim 1 as a component of the reactive resin or reactive-resin component.

6: A method of lowering viscosity of a reactive resin for construction purposes, the method comprising: incorporating the compound according to claim 1 in a reactive resin in need thereof.

7: A method of increasing the bond strength of a cured fastening caulk, the method comprising: mixing the compound according to claim 1 as a component of a fastening caulk in need thereof.

8: A reactive resin, comprising: the compound according to claim 1, an inhibitor, an accelerator, and optionally a reactive diluent.

9: A reactive-resin component for a reactive-resin system, comprising: the reactive resin according to claim 8.

10: A reactive-resin system, comprising: the reactive-resin component (A) according to claim 9, and a hardener component (B), which contains an initiator.

11: The reactive-resin system according to claim 10, wherein at least one of the components (A) or (B) contains an inorganic aggregate.

12: A method of preparing a reactive-resin system for construction, the method comprising: combining a reactive-resin component (A) and a hardener component (B) containing an initiator, thereby obtaining the reactive resin system according to claim 10.

13: A method of chemical fastening of an anchor in a drilled hole, the method comprising: chemically fastening an anchor in a drilled hole with the reactive-resin system of claim 10.

14: A method of reducing extrusion force of a reactive-resin component or a reactive-resin system for construction, the method comprising: incorporating the compound according to claim 1 in a reactive-resin component in need thereof or in a reactive-resin system in need thereof.

15: The reactive resin of claim 8, wherein a proportion of the compound of general formula (I) in the reactive resin is from 25 wt % to 65 wt %.

16: The reactive-resin system of claim 10, having an extrusion force of from 462.1 to 1322 N at 0 C. and/or an extrusion force of from 281 to 1036 N at 25 C.

17. The method of claim 13, wherein a bond strength of the anchor in the drilled hole, chemically fastened with the reactive-resin system, is at least 10.2 N/mm.sup.2.

Description

EXAMPLES

[0191] First of all, reactive resins, reactive-resin components and two-component reactive-resin systems respectively containing the inventive compound (IV) as backbone resin were produced. The dynamic viscosity of the reactive resins and of the reactive-resin components were determined, as were the forces for extruding the two-component reactive-resin systems and the bond strengths of the cured fastening caulks.

Inventive Compound (IV)

A1. Production of Reactive-Resin Master Batch A1 Containing Compound (IV)

[0192] 1542 g Hydroxypropyl methacrylate was first introduced into a 2-liter glass laboratory reactor with internal thermometer and stirrer shaft then 0.24 g phenothiazine (D Prills; Allessa Chemie), 0.60 g 4-hydroxy-2,2,6,6-tetramethyl-piperidinyl-1-oxyl (TEMPOL; Evonik Degussa GmbH) and 0.40 g dioctyltin dilaurate (TIB KAT 216; TIB Chemicals) were added. The batch was heated to 80 C. Then 500 g toluene-2,4-diisocyanate (TDI; TCI Deutschland GmbH) was added with stirring at 200 rpm within 45 minutes. Thereafter stirring was continued for a further 180 minutes at 80 C.

[0193] Hereby reactive-resin master batch A1 containing 65 wt % of compound (IV) as backbone resin and 35 wt % hydroxypropyl methacrylate, relative to the total weight of the reactive-resin master batch, was obtained.

[0194] Compound (IV) has the following structure:

##STR00008##

[0195] A reactive resin (A2.1) containing 33 wt % and a reactive resin (A2.2) containing 41 wt % of compound (IV) as the backbone resin was produced from reactive-resin master batch A1.

A2.1 Production of Reactive Resin A2.1 Containing 33 wt % of Compound (IV)

[0196] 301 g Reactive-resin master batch A1 was mixed with 90 g hydroxypropyl methacrylate and 196 g 1,4-butanediol dimethacrylate (BDDMA; Evonik AG). 2.75 g 4-Hydroxy-2,2,6,6-tetramethyl-piperidinyl-1-oxyl (TEMPOL; Evonik Degussa GmbH) and 10.5 g di-iso-propanol-p-toluidine (BASF SE) were added to this mixture.

[0197] Hereby reactive-resin A2.1 containing a proportion of 33 wt % of compound (IV) as backbone resin was obtained.

A2.2 Production of Reactive Resin A2.2 Containing 41 wt % of Compound (IV)

[0198] 376 g Reactive-resin master batch A1 was mixed with 39 g hydroxypropyl methacrylate and 171 g 1,4-butanediol dimethacrylate (BDDMA; Evonik AG). 2.75 g 4-Hydroxy-2,2,6,6-tetramethyl-piperidinyl-1-oxyl (TEMPOL; Evonik Degussa GmbH) and 10.5 g di-iso-propanol-p-toluidine (BASF SE) were added to this mixture.

[0199] Hereby reactive-resin A2.2 containing a proportion of 41 wt % of compound (IV) as backbone resin was obtained.

A3. Production of Reactive-Resin Components A3. And A3.2

[0200] 354 g Reactive resin A2.1 or A2.2 was mixed with 185 g Secar 80 (Kemeos Inc.), 27 g Cab-O-Sil TS-720 (Cabot Corporation) and 335 g quartz sand F32 (Quarzwerke GmbH), using a PC Labor System Dissolver of LDV 0.3-1 type for 8 minutes at 3500 rpm under vacuum (pressure<100 mbar) with a 55 mm dissolver disk and an edge scraper.

[0201] Hereby reactive-resin components A3.1 and A3.2 were obtained.

[0202] From these, reactive-resin systems were produced as two-component systems.

A4. Production of Two Component Reactive-Resin Systems A4.1 and A4.2

[0203] For production of the two-component reactive-resin systems A4.1 and A4.2, the reactive-resin components A3.1 and A3.2 (component (A)) and respectively the hardener component (component (B)) of the commercially available product HIT-HY 110 (Hilti Aktiengesellschaft; batch number: 1610264) were filled into plastic canisters (Ritter GmbH; volume ratio A:B=3:1) with inside diameters of 47 mm (component (A)) and respectively 28 mm (component (B)).

[0204] Hereby the two-component reactive-resin systems A4.1 (containing a proportion of 33 wt % of compound (IV) in the reactive resin) and A4.2 (containing a proportion of 41 wt % of compound (IV) in the reactive resin) were obtained.

[0205] In order to introduce a higher proportion of compound (IV) into a reactive resin, a further reactive-resin master batch (B1) with a high proportion of 80 wt % of compound (IV) was produced.

B1. Production of Reactive-Resin Master Batch B1 Containing Compound (IV)

[0206] 1396 g Hydroxypropyl methacrylate was first introduced into a 2-liter glass laboratory reactor with internal thermometer and stirrer shaft then 0.29 g phenothiazine (D Prills; Allessa Chemie), 0.70 g 4-hydroxy-2,2,6,6-tetramethyl-piperidinyl-1-oxyl (TEMPOL; Evonik Degussa GmbH) and 0.49 g dioctyltin dilaurate (TIB KAT 216; TIB Chemicals) were added. The batch was heated to 80 C. Then 602 g toluene-2,4-diisocyanate (TCI Deutschland GmbH) was added with stirring at 200 rpm within 45 minutes. Thereafter stirring was continued for a further 180 minutes at 80 C.

[0207] Hereby reactive-resin master batch B1 containing 80 wt % of compound (IV) as backbone resin and 20 wt % hydroxypropyl methacrylate, relative to the total weight of the reactive-resin master batch, was obtained.

[0208] Reactive resins containing different proportions of compound (IV) as the backbone resin were likewise produced from reactive-resin master batch B1.

B2.1 Production of Reactive Resin B2.1 Containing 37 wt % of Compound (IV)

[0209] 186 g Reactive-resin master batch from B1 was mixed with 43 g hydroxypropyl methacrylate and 160 g 1,4-butanediol dimethacrylate (BDDMA; Evonik AG). 1.08 g Pyrocatechol (manufacturer Solvay Catechol Flakes) and 0.36 g 4-tert-butylpyrocatechol and 9.2 g di-iso-propanol-p-toluidine (BASF SE) were added to this mixture.

[0210] Hereby reactive resin B2.1 containing a proportion of 37 wt % of compound (IV) as backbone resin was obtained.

B2.2 Production of Reactive Resin B2.2 Containing 40 wt % of Compound (IV)

[0211] 200 g Reactive-resin master batch B1 was mixed with 37 g hydroxypropyl methacrylate and 153 g 1,4-butanediol dimethacrylate (BDDMA; Evonik AG). 1.08 g Pyrocatechol (manufacturer Solvay Catechol Flakes) and 0.36 g 4-tert-butylpyrocatechol and 9.2 g di-iso-propanol-p-toluidine (manufacturer BASF SE) were added to this mixture.

[0212] Hereby reactive resin B2.2 containing a proportion of 40 wt % of compound (IV) as backbone resin was obtained.

B2.3 Production of Reactive Resin B2.3 Containing 45 wt % of Compound (IV)

[0213] 225 g Reactive-resin master batch B1 was mixed with 26 g hydroxypropyl methacrylate and 140 g 1,4-butanediol dimethacrylate (BDDMA; Evonik AG). 1.08 g Pyrocatechol (manufacturer Solvay Catechol Flakes) and 0.36 g 4-tert-butylpyrocatechol and 9.2 g di-iso-propanol-p-toluidine (BASF SE) were added to this mixture.

[0214] Hereby reactive resin B2.3 containing a proportion of 45 wt % of compound (IV) as backbone resin was obtained.

B2.4 Production of Reactive Resin B2.4 Containing 50 wt % of Compound (IV)

[0215] 250 g Reactive-resin master batch B1 was mixed with 13 g hydroxypropyl methacrylate and 127 g 1,4-butanediol dimethacrylate (BDDMA; Evonik AG). 1.08 g Pyrocatechol (manufacturer Solvay Catechol Flakes) and 0.36 g 4-tert-butylpyrocatechol and 9.2 g di-iso-propanol-p-toluidine (BASF SE) were added to this mixture.

[0216] Hereby reactive resin B2.4 containing a proportion of 50 wt % of compound (IV) as backbone resin was obtained.

B3. Production of Reactive-Resin Components B3.1. B3.2. B3.3 and B3.4

[0217] Respectively 311 g reactive resin B2.1, B2.2, B2.3 and B2.4 were mixed with 167 g Secar 80 (Kemeos Inc.), 9 g Cab-O-SiP TS-720 (Cabot Corporation), 16 g Aerosil R812 (Evonik Industries AG) and 398 g quartz sand F32 (Quarzwerke GmbH) in the dissolver under vacuum. Mixing was carried out with a PC Labor System Dissolver of LDV 0.3-1 type, as described under heading A3.

[0218] Hereby reactive-resin components B3.1, B3.2, B3.3 and B3.4 containing compound (IV) as backbone resin were obtained.

[0219] From these, reactive-resin systems were produced as two-component systems.

B4. Production of Two-Component Reactive-Resin Systems B4.1 to B4.4

[0220] For production of the two-component reactive-resin systems B4.1, B4.2, B4.3 and B4.4, the reactive-resin components B3.1, B3.2, B3.3 and B3.4 (component (A)) and respectively the hardener component (component (B)) of the commercially available product HIT HY-200 (Hilti Aktiengesellschaft; batch number 8104965) were filled into plastic canisters (Ritter GmbH; volume ratio A:B=5:1) with inside diameters of 32.5 mm (component (A)) and respectively 14 mm (component (B)).

[0221] Hereby the two-component reactive-resin systems B4.1 (containing a proportion of 37 wt % of compound (IV) in the reactive resin), B4.2 (containing a proportion of 40 wt % of compound (IV) in the reactive resin), B4.3 (containing a proportion of 45 wt % of compound (IV) in the reactive resin) and B4.4 (containing a proportion of 50 wt % of compound (IV) in the reactive resin) were obtained.

Comparison Examples C and D

[0222] For comparison, reactive-resin master batches, reactive resins and reactive-resin components containing comparison compounds 1 and 2 were produced as follows.

C1. Production of Comparison Reactive-Resin Master Batch C1 Containing Comparison Compound 1

[0223] Comparison reactive-resin master batch C1 containing 65 wt % comparison compound 1 as backbone resin and 35 wt % hydroxypropyl methacrylate was produced according to the method in EP 0 713 015 A1, which is included herewith as reference and to the entire disclosure of which reference is made.

[0224] The product (comparison compound 1) has an oligomer distribution, wherein the oligomer containing a repeat unit has the following structure:

##STR00009##

C2.1 Production of Comparison Reactive Resin C2.1 Containing 33 wt % of Comparison Compound 1

[0225] 9.2 g 4-Hydroxy-2,2,6,6-tetramethyl-piperidinyl-1-oxyl (TEMPOL; Evonik Degussa GmbH) and 35.0 g di-iso-propanol-p-toluidine (BASF SE) were added to a mixture of 1004 g reactive-resin master batch from C1, 300 g hydroxypropyl methacrylate and 652 g 1,4-butanediol dimethacrylate (BDDMA; Evonik AG).

[0226] Hereby comparison reactive-resin C2.1 containing 33 wt % of comparison compound 1 as backbone resin was obtained.

C2.2 Production of Comparison Reactive Resin 1 Containing 37 wt % of Comparison Compound 1

[0227] 229 g Reactive-resin master batch C1 was mixed with 160 g 1,4-butanediol dimethacrylate (BDDMA; Evonik AG). 1.08 g Pyrocatechol (manufacturer Solvay, Catechol Flakes) and 0.36 g 4-tert-butylpyrocatechol (tBBK, CFS EUROPE S.p.A. (Borregaard Italia S.p.A.)) and 9.2 g di-iso-propanol-p-toluidine (BASF SE) were added to this mixture.

[0228] Hereby comparison reactive-resin C2.2 containing 37 wt % of comparison compound 1 as backbone resin was obtained.

C2.3 Production of Comparison Reactive Resin C2.3 Containing 41 wt % of Comparison Compound 1

[0229] 2.8 g 4-Hydroxy-2,2,6,6-tetramethyl-piperidinyl-1-oxyl (TEMPOL; Evonik Degussa GmbH) and 10.5 g di-iso-propanol-p-toluidine (BASF SE) were added to a mixture of 337 g comparison reactive-resin master batch C1, 39 g hydroxypropyl methacrylate and 171 g 1,4-butanediol dimethacrylate.

[0230] Hereby comparison reactive-resin C2.3 containing 41 wt % of comparison compound 1 as backbone resin was obtained.

C3. Production of Comparison Reactive-Resin Components C3.1 to C3.3

[0231] Respectively 354 g comparison reactive resin C2.1 and C2.3 were mixed with 185 g Secar 80 (Kemeos Inc.), 27 g Cab-O-Si TS-720 (Cabot Corporation) and 335 g quartz sand F32 (Quarzwerke GmbH) in the dissolver under vacuum. Mixing was carried out with a PC Labor System Dissolver of LDV 0.3-1 type, as described under heading A3.

[0232] Hereby the comparison reactive-resin components C3.1 containing 33 wt % comparison compound 1 in the reactive resin (from C2.1) and C3.2 containing 41 wt % comparison compound 1 in the reactive resin (from C2.3) were obtained.

[0233] 311 g Comparison reactive resin C2.2 was mixed with 167 g Secar 80 (Kerneos Inc.), 9 g Cab-O-SiP TS-720 (Cabot Corporation), 16 g Aerosil R812 (Evonik Industries AG) and 398 g quartz sand F32 (Quarzwerke GmbH) in the dissolver under vacuum. Mixing was carried out with a PC Labor System Dissolver of LDV 0.3-1 type, as described under heading A3.

[0234] Hereby the comparison reactive-resin components C3.3 containing 37 wt % comparison compound in the reactive resin (from C2.2) was obtained.

C4. Production of Comparison Two-Component Reactive-Resin Systems C4.1 to C4.3

[0235] For production of the comparison two-component reactive-resin systems C4.1 and C4.2, the reactive-resin components C3.1 and C3.2 (component (A)) and respectively the hardener component (component (B)) of the commercially available product HIT-HY 110 (Hilti Aktiengesellschaft; batch number: 1610264) were filled into plastic canisters (Ritter GmbH; volume ratio A:B=3:1) with inside diameters of 47 mm (component (A)) and respectively 28 mm (component (B)).

[0236] Hereby the two-component comparison reactive-resin systems C4.1 containing 33 wt % comparison compound 1 in the reactive resin (from C3.1) and C4.2 containing 41 wt % comparison compound 1 in the reactive resin (from C3.2) were obtained.

[0237] For production of the comparison two-component reactive-resin system C4.3, the reactive-resin components C3.3 (component (A)) and respectively the hardener component (component (B)) of the commercially available product HIT-HY 200 (Hilti Aktiengesellschaft; batch number 8104965) were filled into plastic canisters (Ritter GmbH; volume ratio A:B=5:1) with inside diameters of 32.5 mm (component (A)) and respectively 14 mm (component (B)).

[0238] Hereby comparison two-component reactive-resin system C4.3 containing 37 wt % of comparison compound 1 in the reactive resin (from C3b) was obtained.

D1. Production of Comparison Reactive-Resin Master Batch D1 Containing Comparison Compound 2

[0239] The comparison reactive-resin master batch D1 containing respectively 65 wt % comparison compound 2 as backbone resin and 35 wt % hydroxypropyl methacrylate, respectively relative to the total weight of the reactive-resin master batch, was produced according to the method in EP 0 713 015 A1, which is included herewith as reference and to the entire disclosure of which reference is made.

[0240] Comparison compound 2 has the following structure:

##STR00010##

[0241] From this, comparison reactive resins containing different proportions of comparison compound 2 were produced.

D2. Production of Comparison Reactive Resin D2

[0242] 4.6 g 4-Hydroxy-2,2,6,6-tetramethyl-piperidinyl-1-oxyl (TEMPOL; Evonik Degussa GmbH) and 17.5 g di-iso-propanol-p-toluidine (BASF SE) were added to a mixture of 502 g comparison reactive-resin master batch D1, 150 g hydroxypropyl methacrylate and 326 g 1,4-butanediol dimethacrylate (1,4-BDDMA; Evonik Degussa GmbH).

[0243] Hereby comparison reactive resin D2 containing comparison compound 2 as backbone resin was obtained.

D3. Production of Comparison Reactive-Resin Component D3

[0244] 354 g Comparison reactive resin D2 was mixed with 185 g Secar 80 (Kemeos Inc.), 27 g Cab-O-Sil TS-720 (Cabot Corporation) and 335 g quartz sand F32 (Quarzwerke GmbH) in the dissolver under vacuum. Mixing was carried out with a PC Labor System Dissolver of LDV 0.3-1 type, as described under heading A3.

[0245] Hereby comparison reactive-resin component D3 containing comparison compound 2 as the backbone resin was obtained.

D4. Production of Comparison Two-Component Reactive-Resin System D4

[0246] For production of the comparison two-component reactive-resin system D4, the comparison reactive-resin component D3 (component (A)) and the hardener component (component (B)) of the commercially available product HIT-HY 110 (Hilti Aktiengesellschaft; batch number: 1610264) were filled into a plastic canister (Ritter GmbH; volume ratio A:B=3:1) with inside diameters of 47 mm (component (A)) and respectively 28 mm (component (B)).

[0247] Hereby comparison two-component reactive-resin system D4 was obtained.

[0248] In order to demonstrate the influence of inventive compound (IV) on the viscosity of a reactive-resin master batch, of a reactive resin and of a reactive-resin component containing this as well as the influence on the bond strengths of a cured fastening caulk, the viscosities of the inventive reactive-resin master batches, reactive resins, reactive-resin components, the forces for extruding two-component reactive-resin systems as well as the bond strengths of cured fastening caulks were measured and respectively compared with the comparison formulations.

Measurement of the Dynamic Viscosity of Reactive-Resin Master Batch A1 and of Comparison Master Batches C1 and D1

[0249] The dynamic viscosity of reactive-resin master batch A1 and of comparison reactive-resin master batches C1 and D1 (Table 1) was measured with a cone-and-plate measuring system according to DIN 53019. The diameter of the cone was 20 mm and the opening angle was 1. The measurement was performed at a constant shear velocity of 100/s and the respective temperature (0, 5, 10, 15, 20, 30 and 40 C.). The measurement duration was 120 s and one measured point was generated every second. The shear velocity was attained at the respective temperature by a preceding ramp from 0 to 100/s over a duration of 30 s. Since Newtonian fluids are involved, a linear evaluation over the measurement portion was undertaken and the viscosity was determined with constant shear velocity of 100/s over the measurement portion. Respectively three measurements were made, wherein the respective mean values are indicated in Table 1.

Measurement of the Dynamic Viscosity of the Reactive-Resin Components A3.1. B3.1. B3.2. B3.3 and B3.4 as Well as of Comparison Reactive-Resin Components C3.1. C3.3 and D3

[0250] The dynamic viscosity of the inventive reactive-resin component A3 and of comparison reactive-resin components C3 and D3 (Table 2) as well as of reactive-resin components B3.1, B3.2, B3.3 and B3.4 and of comparison reactive-resin components C3.3 (Table 3) was measured with using a plate/plate measuring system according to DIN 53019. The diameter of the plate was 20 mm and the gap distance was 3 mm. In order to prevent escape of the sample from the gap, a limiting ring of Teflon having a distance of 1 mm from the upper plate was used. The measurement temperature was 25 C. The method consisted of three portions: 1st Low shear, 2nd High shear, 3rd Low shear. During the 1st portion, shear was applied for 3 minutes at 0.5/s. In the 2nd portion, the shear velocity was increased logarithmically from 0.8/s to 100/s in 8 stages of 15 seconds each. These individual stages were: 0.8/s; 1.724/s; 3.713/s; 8/s; 17.24/s; 37.13/s; 80/s; 100/s. The 3rd portion was a repetition of the 1st portion. The viscosities were read at the end of each portion. The value of the second portion at 100/s is indicated in Table 2. Respectively three measurements were made, wherein the values indicated in Table 2 are the mean values of the three measurements.

[0251] First of all, the dynamic viscosity of reactive-resin master batch A1 containing comparison reactive-resin master batches C1 and D1 was compared at different temperatures (Table 1). The reactive-resin master batches respectively contained 65 wt % backbone resin and 35 wt % hydroxypropyl methacrylate.

TABLE-US-00001 TABLE 1 Results of the measurements of the dynamic viscosity of reactive-resin master batch A1 and of comparison reactive-resin master batches C1 and D1 at different temperatures Comparison Reactive-resin Comparison reactive-resin reactive-resin master batch master batch master batch A1 C1 D1 T [ C.] Viscosity [mPa .Math. s] 0 45,390 188,000 281.200 5 18,970 81,520 110,500 10 8,325 37,050 45,020 15 3,815 17,280 19.470 20 1,976 8,900 9,573 30 642 2,795 2,769 40 251 1,063 955

[0252] The measured results in Table 1 show that the inventive compounds cause a lowering of the dynamic viscosity, especially at low temperatures. Especially at temperatures below 20 C., the dynamic viscosity of the inventive reactive-resin master batches containing the inventive compound (IV) is lower than the dynamic viscosity of reactive-resin master batches C1 and D1, which contain comparison compounds 1 and 2.

[0253] Furthermore, the dynamic viscosity of reactive-resin component A3.1 produced from the inventive reactive-resin master batch A1 was compared with the dynamic viscosity of the reactive-resin components C3.1 and D3 produced from comparison reactive-resin master batches C1 and D1 (Table 2). All reactive-resin components from Table 2 contained 33 wt % of backbone resin in the reactive resin.

TABLE-US-00002 TABLE 2 Results of the measurements of the dynamic viscosity of reactive-resin component A3.1 and of comparison reactive-resin components C3.1 and D3 Comparison Comparison Reactive-resin reactive-resin reactive-resin component A3.1 component C3.1 component D3 Dynamic 11.3 13.9 12.8 viscosity [Pa .Math. s]; 25 C.

[0254] The measured results in Table 2 show that the inventive compounds also lead to lowering of the dynamic viscosity of the reactive-resin components containing them. The dynamic viscosity of the inventive reactive-resin component containing the inventive compound (IV) is lower than the dynamic viscosity of comparison reactive-resin components C3.1 and D3, which contain comparison compounds 1 and 2.

[0255] In order to show that, by use of the inventive compounds, it is possible with the example of compound (IV) to increase the proportion of backbone resin in the reactive resin and thus in the reactive-resin component, without hereby increasing the viscosity too much, and without increasing the extrusion forces too much, the dynamic viscosity of reactive-resin components containing different proportions of backbone resin was measured (Table 3).

TABLE-US-00003 TABLE 3 Results of the measurement of the dynamic viscosity of reactive-resin components B3.1, B3.2, B3.3 and B3.4 as well as of comparison reactive-resin component C3.3 Comparison Reactive-resin Reactive-resin Reactive-resin Reactive-resin reactive-resin component component component component component B3.1 B3.2 B3.3 B3.4 C3.3 Proportion of 37 wt % 40 wt % 45 wt % 50 wt % 37 wt % backbone resin in reactive resin Dynamic 7.4 8.8 11.7 15.1 12.5 viscosity [Pa .Math. s]; 25 C.

[0256] The results in Table 3 show that the dynamic viscosity of the reactive-resin component remains relatively low despite the increase of the proportion of backbone resin. Even an increase of the proportion of backbone resin to 45 wt % leads to a reactive-resin component that has a lower viscosity than the comparison reactive-resin component containing a backbone-resin proportion of 37 wt %.

[0257] Even at a backbone-resin proportion of 50 wt %, the viscosity of the reactive-resin component is only slightly higher than that of the comparison reactive-resin component containing a backbone-resin proportion of 37 wt %. At the same proportion of backbone resin in the reactive resin, the dynamic viscosity of the inventive reactive-resin component is much lower than that of the comparison reactive-resin component.

Determination of the Extrusion Forces

[0258] For determination of the forces for extrusion of the reactive-resin systems, the canisters containing the respective reactive-resin components (component (A)) and hardener component (component (B)) were adjusted to temperatures of 0 C. and 25 C. respectively. Using a material-testing machine of the Zwick Co. with a load cell (test range up to 10 kN), the canisters were extruded via a static mixer (HIT-RE-M mixer; Hilti Aktiengesellschaft) with a constant speed of 100 mm/min over a path of 45 mm and the mean force developed in the process was measured.

[0259] The forces for extruding two-component reactive-resin system A4.1 as well as comparison two-component reactive-resin systems C4.1 and D4, which respectively contain a proportion of 33 wt % of backbone resin in the reactive resin, were measured at 0 C. and 25 C. (Table 4).

TABLE-US-00004 TABLE 4 Results of the measurement of the forces for extruding two-component reactive-resin system A4.1 and comparison two-component reactive-resin systems 04.1 and D4 at 0 C. and 25 C. Comparison Two-component Comparison two-component reactive-resin two-component reactive-resin system reactive-resin system system A4.1 C4.1 D4 Force [N] 1322 1631 1639 at 0 C. Force [N] 1036 1151 1079 at 25 C.

[0260] The forces for extruding two-component reactive-resin system B4.1 as well as comparison two-component reactive-resin system C4.3, which respectively contain a proportion of 37 wt % of backbone resin in the reactive resin, were measured at 0 C. and 25 C. (Table 5).

TABLE-US-00005 TABLE 5 Results of the measurement of the forces for extruding two-component reactive-resin system B4.1 and comparison two-component reactive-resin system C4.3 at 0 C. and 25 C. Two-component reactive-resin system Comparison two-component B4.1 reactive-resin system C4.3 Force [N] 579 700 at 0 C. Force [N] 281 368 at 25 C.

[0261] The results in Tables 4 and 5 show that the forces for extruding the inventive two-component reactive-resin systems are lower both at 0 C. and at 25 C. than the forces for extruding the comparison two-component reactive-resin systems.

Measurement of the Bond Strength

[0262] To determine the bond strengths (load ratings) of the cured fastening caulks, M12 threaded anchor rods were inserted into drilled holes in C20/25 concrete, which had a diameter of 14 mm and a drilled-hole depth of 72 mm and were filled with the reactive-resin mortar compositions. The bond strengths were determined by pulling out the threaded anchor rods centrally. Respectively five threaded anchor rods were set and the bond strength was determined after 24 hours of curing. The fastening caulks were extruded from the canisters and injected into the drilled holes via a static mixer (HIT-RE-M Mixer; Hilti Aktiengesellschaft).

[0263] The bond strength was determined under the following drilled-hole conditions:

A1: In a cleaned, dust-free, dry, drilled hole produced by hammer-drilling. Setting, curing and extraction took place at room temperature. The temperature of the two-component reactive-resin system or of the fastening caulks during setting was 20 C.
F1b: In a half-cleaned (approximately 50% dust-free) wet drilled hole produced by hammer-drilling. Setting, curing and extraction took place at room temperature. The temperature of the two-component reactive-resin system or of the fastening caulks during setting was 20 C.
A21 (80 C.): In a cleaned, dust-free, dry, drilled hole produced by hammer-drilling. Setting and curing took place at room temperature. Thereafter the concrete and dowels were stored for 24 hours at 80 C. Extraction took place at 80 C. The temperature of the two-component reactive-resin system or of the fastening caulks during setting was 20 C.
A23 (5 C.): In a cleaned, dust-free, dry, drilled hole produced by hammer-drilling. Setting, curing and extraction took place at 5 C. The temperature of the two-component reactive-resin system or of the fastening caulks during setting was 0 C.

[0264] The bond strengths (N/mm.sup.2) determined in this way are listed as the mean value of five measurements in the following Tables 6 and 7.

TABLE-US-00006 TABLE 6 Bond strengths measured under A1, F1b*, A23 and A21 conditions for the fastening caulks from the two-component reactive-resin systems A4.1 and A4.2 and for the comparison fastening caulk from comparison two-component reactive-resin system C4.1 Bond strength [N/mm.sup.2] A1 F1b* A23 (5 C.) A21 (80 C.) Fastening caulk from A4.1 18.3 12.3 10.2 12.9 containing 33 wt % backbone resin in the reactive resin Fastening caulk from A4.2 20.9 14.5 13.5 14.3 containing 41 wt % backbone resin in the reactive resin Comparison fastening caulk 20.3 13.0 11.6 11.9 from C4.1 containing 33 wt % backbone resin in the reactive resin

[0265] The results in Table 6 show that the bond strengths of the fastening caulk from A4.1, which has a backbone-resin proportion of 33 wt %, are approximately equal, under A1, F1b and A23 conditions, to the bond strengths of the comparison fastening caulk from C4.1. Under A21 conditions, the bond strengths of the fastening caulk from A4.1 are somewhat higher than the bond strengths of the comparison fastening caulk from C4.1. Furthermore, it is evident that an increase in the proportion of backbone resin also leads to an increase of the bond strength, as in the fastening caulk from A4.2.

[0266] This is also shown by the results in Table 7, wherein, with increasing backbone-resin proportion (B4.1.fwdarw.B4.4), an increase of the bond strengths was observed compared with the bond strength of the comparison fastening caulk from C4.3 (37 wt % backbone resin in the reactive resin).

TABLE-US-00007 TABLE 7 Results of the measurements of the bond strengths, measured under A1 conditions, for the fastening caulks from the two-component reactive-resin systems B4.1 to B4.4 and for the comparison fastening caulk from comparison two-component reactive-resin system C4.3 Fastening caulk comprising B4.1 B4.2 B4.3 B4.4 C4.3 Proportion of 37 wt % 40 wt % 45 wt % 50 wt % 37 wt % backbone resin in the reactive resin Bond 33.7 34.4 34.6 35.6 33.3 strength [N/mm.sup.2]

[0267] Furthermore, reactive resins, reactive-resin components and two-component reactive-resin systems respectively containing the inventive compound (IV) as backbone resin were produced. The dynamic viscosity of the reactive resins and of the reactive-resin components were determined, as were the forces for extruding the two-component reactive-resin systems.

Inventive Compound (V)

[0268] Furthermore, reactive resin master batches, reactive resins, reactive-resin components and two-component reactive-resin systems respectively containing the inventive compound (V) as backbone resin were produced. The dynamic viscosity of the reactive-resin master batches and of the reactive-resin components as well as the forces for extruding the two-component reactive-resin systems were determined and compared with the corresponding values for the comparison compositions.

E1.1 Production of Reactive-Resin Master Batch E1 Containing 65 wt % of Compound (V) and 35 wt % of 1.4-Butanediol Dimethacrylate

[0269] 80400 g Hydroxypropyl methacrylate (Visiomerr HPMA; Evonik Degussa GmbH) was first introduced into a 300-liter steel reactor with internal thermometer and stirrer shaft then 36 g phenothiazine (D Prills; Allessa Chemie), 70 g 4-hydroxy-2,2,6,6-tetramethyl-piperidinyl-1-oxyl (TEMPOL; Evonik Degussa GmbH) and 56 g dioctyltin dilaurate (TIB KAT 216; TIB Chemicals) were added. The batch was heated to 60 C. Then 69440 g methylene-di(phenyl isocyanate) (MDI; Lupranat MIS, BASF SE) was added dropwise with stirring within 1.5 hours. Thereafter stirring was continued for a further 45 minutes at 80 C. Then 50000 g 1,4-butanediol dimethacrylate (Visiomer 1,4-BDDMA, Evonik Degussa GmbH) was added.

[0270] Reactive-resin master batch E1.1 containing 75 wt % of compound (V) as backbone resin and 25 wt % of 1,4-butanediol dimethacrylate, relative to the total weight of the reactive-resin master batch, was obtained.

[0271] By dilution with 1,4-butanediol dimethacrylate, it was possible to dilute reactive-resin master batch E1.1 to the point that the master batch contained 65 wt % of compound (V) and 35 wt % of 1,4-butanediol dimethacrylate.

[0272] Compound (V) has the following structure:

##STR00011##

E1.2 Production of the Inventive Reactive-Resin Master Batch E1.2 Containing 65 wt % of Compound (V and 35 wt % of Hydroxypropyl Methacrylate

[0273] 1396 g Hydroxypropyl methacrylate (Visiomer HPMA 98; Evonik Degussa GmbH) was first introduced into a 2-liter glass laboratory reactor with internal thermometer and stirrer shaft then 0.3 g phenothiazine (D Prills; Allessa Chemie), 0.6 g 4-hydroxy-2,2,6,6-tetramethyl-piperidinyl-1-oxyl (TEMPOL; Evonik Degussa GmbH) and 0.48 g dioctyltin dilaurate (TIB KAT 216; TIB Chemicals) were added. The batch was heated to 60 C. Then 602.6 g methylene-di(phenyl isocyanate) (MDI; Lupranat MIS, BASF SE) was added dropwise with stirring (600 rpm) within 1.5 hours. Thereafter stirring was continued for a further 30 minutes at 80 C.

[0274] Hereby reactive-resin master batch E1.2 containing 65 wt % of compound (V) as backbone resin and 35 wt % hydroxypropyl methacrylate, relative to the total weight of the reactive-resin master batch, was obtained.

E2. Production of Reactive Resin E2 Containing 45 wt % of Compound M

[0275] 2520 g Reactive-resin master batch from E1.1 is mixed with 439.74 g hydroxypropyl methacrylate and 1128.54 g 1,4-butanediol dimethacrylate (1,4-BDDMA; Evonik Degussa GmbH). 96.6 g Di-isopropanol-p-toluidine (BASF SE), 13.44 g catechol (Catechol Flakes, RHODIA) and 5.88 g tert-Butylpyrocatechol (tBBK, CFS EUROPE S.p.A. (Borregaard Italia S.p.A.)) were added to this mixture and stirred until complete homogenization.

[0276] Hereby reactive-resin E2 containing 45 wt % of compound (V) as backbone resin was obtained.

E3.1 Production of Reactive-Resin Component E3.1

[0277] (for measurement of the viscosity and of the extrusion forces at 23 C.)

[0278] 2106 g Reactive resin E2 was mixed with 930.42 g Secar 80 (Kemeos Inc.), 64.8 g Cab-O-Sil TS-720 (Cabot Corporation), 90.72 g Aerosil R 812 (Evonik Industries AG) and 2222.64 g quartz sand F32 (Quarzwerke GmbH) in the dissolver under vacuum, using a PC Labor System Dissolver of LDV 0.3-1 type. The mixture was stirred for 2 minutes at 2500 rpm and thereafter for 10 minutes at 4500 rpm under vacuum (pressure s 100 mbar) with a 55 mm dissolver disk and an edge scraper.

[0279] Hereby reactive-resin component E3.1 was obtained.

E3.2 Production of Reactive-Resin Component E3.2

[0280] (for measurement of the viscosity at 0 C. and 25 C. and of the extrusion forces at 0 C.) 1053 g Reactive resin E2 was mixed with 465.21 g Secar 80 (Kemeos Inc.), 27 g Cab-O-Sil TS-720 (Cabot Corporation), 48.6 g Aerosil R 812 (Evonik Industries AG) and 1111.32 g quartz sand F32 (Quarzwerke GmbH) in the dissolver under vacuum. Mixing was carried out with a PC Labor System Dissolver of LDV 0.3-1 type, as described under heading E3.1.

[0281] Hereby reactive-resin component E3.2 was obtained.

E4. Production of Two Component Reactive-Resin Systems E4.1 and E4.2

[0282] For production of the two-component reactive-resin systems E4.1 and E4.2, respectively the reactive-resin components E3.1 and E3.2 (component (A)) and the hardener component (component (B)) of the commercially available product HIT-HY 200 (Hilti Aktiengesellschaft; batch number: 8104965) were filled into a plastic canister (Ritter GmbH; volume ratio A:B=5:1) with inside diameters of 32.5 mm (component (A)) and respectively 14 mm (component (B)).

[0283] Hereby the two-component reactive-resin systems E4.1 (for measurement of the extrusion forces at 23 C.) and E4.2 (for measurement of the extrusion forces at 0 C.) were obtained.

Comparison Examples F and G

[0284] For comparison, reactive-resin master batches, reactive resins and reactive-resin components containing comparison compounds 1 and 2 two-were produced as follows.

F1. Production of Comparison Reactive-Resin Master Batches F1.1 and F1.2

[0285] A comparison reactive-resin master batch containing 65 wt % of comparison compound 1 as backbone resin and 35 wt % 1,4-butanediol dimethacrylate (F1.1) or hydroxypropyl methacrylate (F1.2), respectively relative to the total weight of the reactive-resin master batch, was synthesized according to the method in EP 0 713 015 A1, which is included herewith as reference and to the entire disclosure of which reference is made.

[0286] The product (comparison compound 1) has an oligomer distribution, wherein the oligomer containing a repeat unit has the following structure:

##STR00012##

F2. Production of Comparison Reactive Resin F2 Containing 45 wt % of Comparison Compound 1

[0287] 830.76 g Comparison reactive-resin master batch F1.1 was mixed with 125.64 g hydroxypropyl methacrylate and 211.68 g 1,4-butanediol dimethacrylate (1,4-BDDMA; Evonik Degussa GmbH). 27.6 g Di-isopropanol-p-toluidine (BASF SE), 3.24 g catechol (Catechol Flakes, RHODIA) and 1.08 g tert-butylpyrocatechol (tBBK, CFS EUROPE S.p.A. (Borregaard Italia S.p.A.)) were added to this mixture and stirred until complete homogenization.

[0288] Hereby comparison reactive-resin F2 containing a 42 wt % proportion of comparison compound 1 as backbone resin was obtained.

F3.1. Production of Comparison Reactive-Resin Component F3.1

[0289] (for measurement of the viscosity and of the extrusion forces at 23 C.)

[0290] 1053 g Comparison reactive resin F2 was mixed with 465.21 g Secar 80 (Kerneos Inc.), 32.4 g Cab-O-Sil TS-720 (Cabot Corporation), 45.36 g Aerosil R812 (Evonik Industries AG) and 1111.33 g quartz sand F32 (Quarzwerke GmbH) in the dissolver under vacuum.

[0291] Hereby comparison reactive-resin component F3.1 containing comparison compound 1 as the backbone resin was obtained.

F3.2. Production of Comparison Reactive-Resin Component F3.2

[0292] (for measurement of the viscosity at 0 C. and 25 C. and of the extrusion forces at 0 C.)

[0293] 1053 g Comparison reactive resin F2 was mixed with 465.21 g Secar 80 (Kerneos Inc.), 27 g Cab-O-Sil TS-720 (Cabot Corporation), 48.6 g Aerosil R812 (Evonik Industries AG) and 1111.32 g quartz sand F32 (Quarzwerke GmbH) in the dissolver under vacuum.

[0294] Hereby comparison reactive-resin component F3.2 containing comparison compound 1 as the backbone resin was obtained.

F4. Production of Comparison Two-Component Reactive-Resin Systems F4.1 and F4.2

[0295] For production of the two-component reactive-resin systems F4.1 and F4.2, respectively the reactive-resin components F3.1 and F3.2 (component (A)) and the hardener component (component (B)) of the commercially available product HIT-HY 200 (Hilti Aktiengesellschaft; batch number: 8104965) were filled into a plastic canister (Ritter GmbH; volume ratio A:B=5:1) with inside diameters of 32.5 mm (component (A)) and respectively 14 mm (component (B)).

[0296] Hereby the two-component reactive-resin systems F4.1 (for measurement of the extrusion forces at 23 C.) and F4.2 (for measurement of the extrusion forces at 0 C.) were obtained.

G1. Production of Comparison Reactive-Resin Master Batches G1.1 and G1.2

[0297] Comparison reactive-resin master batches G1.1 and G1.2 respectively containing 65 wt % of reference compound 2 as backbone resin and 35 wt % 1,4-butanediol dimethacrylate (G1.1) or hydroxypropyl methacrylate (G1.2), respectively relative to the total weight of the reactive-resin master batch, were synthesized according to the method in EP 0 713 015 A1, which is included herewith as reference and to the entire disclosure of which reference is made.

[0298] Comparison compound 2 has the following structure:

##STR00013##

G2. Production of Comparison Reactive Resin G2 Containing 45 wt % of Comparison Compound 2

[0299] 830.76 g Reactive-resin master batch G1.1 was mixed with 125.64 g hydroxypropyl methacrylate and 211.68 g 1,4-butanediol dimethacrylate (1,4-BDDMA; Evonik Degussa GmbH). 27.6 g Di-isopropanol-p-toluidine (BASF SE), 3.24 g catechol (Catechol Flakes, RHODIA) and 1.08 g tert-butylpyrocatechol (tBBK, CFS EUROPE S.p.A. (Borregaard Italia S.p.A.)) were added to this mixture and stirred until complete homogenization.

[0300] Hereby comparison reactive-resin G2 containing a 45 wt % proportion of compound 2 as backbone resin in hydroxypropyl methacrylate and 1,4-butanediol dimethacrylate was obtained.

G3.1. Production of Comparison Reactive-Resin Component G3.1

[0301] (for measurement of the viscosity and of the extrusion forces at 23 C.)

[0302] 1053 g Comparison reactive resin G2 was mixed with 465.21 g Secar 80, 32.4 g Cab-O-Sil TS-720 (Cabot Corporation), 45.36 g Aerosil R812 (Evonik Industries AG) and 1111.32 g quartz sand F32 (Quarzwerke GmbH) in the dissolver under vacuum.

[0303] Hereby comparison reactive-resin component G3.1 containing comparison compound 1 as the backbone resin was obtained.

G3.2. Production of Comparison Reactive-Resin Component G3.2

[0304] (for measurement of the viscosity at 0 C. and 25 C. and of the extrusion forces at 0 C.)

[0305] 1053 g Comparison reactive resin G2 was mixed with 465.21 g Secar 80 (Kemeos Inc.), 27 g Cab-O-Sil TS-720 (Cabot Corporation), 48.6 g Aerosil R812 (Evonik Industries AG) and 1111.32 g quartz sand F32 (Quarzwerke GmbH) in the dissolver under vacuum.

[0306] Hereby comparison reactive-resin component G3.2 containing comparison compound 2 as the backbone resin was obtained.

G4. Production of Comparison Two-Component Reactive-Resin Systems G4.1 and G4.2

[0307] For production of comparison two-component reactive-resin systems G4.1 and G4.2, respectively the reactive-resin components G3.1 and G3.2 (component (A)) and the hardener component (component (B)) of the commercially available product HIT-HY 200 (Hilti Aktiengesellschaft; batch number: 8104965) were filled into a plastic canister (Ritter GmbH; volume ratio A:B=5:1) with inside diameters of 32.5 mm (component (A)) and respectively 14 mm (component (B)).

[0308] Hereby the two-component comparison reactive-resin systems G4.1 (for measurement of the extrusion forces at 23 C.) and G4.2 (for measurement of the extrusion forces at 0 C.) were obtained.

[0309] In order to demonstrate the influence of inventive compound (V) on the viscosity of a reactive-resin master batch, of a reactive resin and of a reactive-resin component containing this, the viscosities of the inventive reactive-resin master batches, reactive resins, reactive-resin components as well as the forces for extruding reactive-resin systems were measured and respectively compared with the comparison formulations.

Measurement of the Dynamic Viscosity of Reactive-Resin Master Batches E1.1 and E1.2 and of Comparison Master Batches F1.1. F1.2. G1.1 and G1.2

[0310] The dynamic viscosity of reactive-resin master batches E1.1 and E1.2 and of comparison reactive-resin master batches F1.1, F1.2, G1.1 and G1.2 (Table 8) was measured with a cone-and-plate measuring system according to DIN 53019. The diameter of the cone was 20 mm and the opening angle was 1. The measurement was performed at a constant shear velocity of 100/s and the respective temperature (0, 5, 10, 15, 20, 30 and 40 C.). The measurement duration was 120 s and one measured point was generated every second. The shear velocity was attained at the respective temperature by a preceding ramp from 0 to 100/s over a duration of 30 s. Since Newtonian fluids are involved, a linear evaluation over the measurement portion was undertaken and the viscosity was determined with constant shear velocity of 100/s over the measurement portion. Respectively three measurements were made, wherein the corresponding mean values are indicated at the bottom of Table 8.

Measurement of the Dynamic Viscosity of Reactive-Resin Component E3.1 as Well as of Comparison Reactive-Resin Components F3.1 and G3.1

[0311] The dynamic viscosity of reactive-resin component E3.1 and of comparison reactive-resin components F3.1 and G3.1 (Table 9) was measured with using a plate/plate measuring system according to DIN 53019. The diameter of the plate was 35 mm and the gap distance was 3 mm. In order to prevent escape of the sample from the gap, a limiting ring of Teflon having a distance of 1 mm from the upper plate was used. The measurement temperature was 23 C. The method consisted of two portions: 1. A ramp from 0/s to 10/s with a duration of 120 s and 100 measurement points. 2. Constant shear of 10/s for 180 s with 180 measurement points. A linear evaluation of the second portion was undertaken and the value was expressed as the viscosity. Respectively three measurements were made, wherein the corresponding mean values are indicated in Table 9.

Measurement of the Dynamic Viscosity of Reactive-Resin Components E3.2 as Well as of Comparison Reactive-Resin Components F3.2 and G3.2

[0312] The dynamic viscosity of reactive-resin component E3.2 and of comparison reactive-resin components F3.2 and G3.2 (Table 10) was measured with a plate/plate measuring system according to DIN 53019. The diameter of the plate was 20 mm and the gap distance was 3 mm. In order to prevent escape of the sample from the gap, a limiting ring of Teflon having a distance of 1 mm from the upper plate was used. The measurement temperature was 0 C. and 25 C. respectively. The method consisted of three portions: 1st Low shear, 2nd High shear, 3rd Low shear. During the 1st portion, shear was applied for 3 minutes at 0.5/s. In the 2nd portion, the shear velocity was increased logarithmically from 0.8/s to 100/s in 8 stages of 15 seconds each. These individual stages were: 0.8/s; 1.724/s; 3.713/s; 8/s; 17.24/s; 37.13/s; 80/s; 100/s. The 3rd portion was a repetition of the 1st portion. The viscosities were read at the end of each portion. The values of the second portion at 8/s and 100/s are indicated in Table 10. Respectively three measurements were made, wherein the corresponding mean values are indicated in Table 10.

[0313] First of all, the dynamic viscosity of reactive-resin master batches E1.1 and E1.2 containing comparison reactive-resin master batches F1.1, F1.2, G1.1 and G1.2 was compared at different temperatures (Table 8). The reactive-resin master batches respectively contained 65 wt % backbone resin and 35 wt % hydroxypropyl methacrylate (E1.1, F1.1, G1.1) or 35 wt % 1,4-butanediol dimethacrylate (E1.2, F1.2, G1.2).

TABLE-US-00008 TABLE 8 Results of the measurements of the dynamic viscosity of reactive- resin master batches E1.1 and E1.2 and of comparison reactive-resin master batches F1.1, F1.2, G1.1 and G1.2 at different temperatures T E1.2 E1.1 F1.2 F1.1 G1.2 G1.1 [ C.] Dynamic viscosity [mPa .Math. s] 40 283 301 952 599 961 1,147 30 736 737 2,897 1,579 2,877 3,139 20 2,356 2,159 11,045 5,045 10,745 10,475 15 4,716 4,104 24,505 10,051 23,240 21,145 10 10,270 8,387 59,360 21,480 54,960 45,855 5 24,150 18,435 156,750 49,575 137,250 106,650 0 62,355 43,800 438,800 123,350 339,950 265,200

[0314] The measured results show that the inventive reactive-resin master batches cause a lowering of the dynamic viscosity, especially at low temperatures. Especially at temperatures below 20 C., the dynamic viscosity of the inventive reactive-resin master batches containing compound (V) as backbone resin is much lower than the viscosity of comparison reactive-resin master batches containing compounds 1 and 2.

[0315] Furthermore, the dynamic viscosity of reactive-resin component E3.1 produced from inventive reactive-resin master batch E1.1 was compared with the dynamic viscosity of the comparison reactive-resin components F3.1 and G3.1 produced from comparison reactive-resin master batches F1.1 and G1.1 (Table 9). All reactive-resin components shown in Table 9 contained 45 wt % of backbone resin in the reactive resin.

TABLE-US-00009 TABLE 9 Results of the measurement of the dynamic viscosity of reactive-resin component E3.1 and of comparison reactive-resin components F3.1 and G3.1 E3.1 F3.1 G3.1 Dyn. viscosity 22.9 26.3 32.5 [Pa .Math. s]; 23 C.

[0316] The results in Table 9 show that the dynamic viscosity of the reactive-resin component containing the inventive compound (V) is relatively low compared with the dynamic viscosity of the comparison reactive-resin components containing comparison compounds 1 and 2 respectively.

[0317] In order to rule out the possibility that the differences in the dynamic viscosity of the reactive-resin components are due to the silica composition used, the measurements were repeated with respectively changed proportions of silica (reactive-resin component E3.2 and comparison reactive-resin components F3.2 and G3.2) and at two different shear rates (8 s.sup.1 and 100 s.sup.1) and two temperatures (0 C. and 25 C.). The results are shown in Table 10.

TABLE-US-00010 TABLE 10 Results of the measurement of the dynamic viscosity of reactive-resin component E3.2 and of comparison reactive-resin components F3.2 and G3.2 E3.2 F3.2 G3.2 E3.2 F3.2 G3.2 (25 C.) (25 C.) (25 C.) (0 C.) (0 C.) (0 C.) Shear rate Dynamic viscosity [Pa .Math. s] 8 s.sup.1 30.9 40.4 44.0 100.5 142.6 168.7 100 s.sup.1 8.3 11.2 13.2 36.4 49.6 61.2

[0318] The results in Table 10 show that, despite changed silica composition, the dynamic viscosity of reactive-resin component E3.2, which contains the inventive compound (V), is relatively low both at 0 C. and at 25 C. compared with the dynamic viscosity of comparison reactive-resin components F3.2 and G3.2, which contain comparison compounds 1 and 2 respectively.

Determination of the Extrusion Forces

[0319] To determine the extrusion forces at 0 C. and 23 C., reactive-resin systems E4.1 as well as comparison reactive-resin systems F4.1 and G4 were adjusted to temperatures of 0 C. and 23 C. respectively. Using a material-testing machine of the Zwick Co. with a load cell (test range up to 10 kN), the canisters were extruded via a static mixer (HIT-RE-M mixer; Hilti Aktiengesellschaft) with a constant speed of 100 mm/min over a path of 45 mm and the mean force developed in the process was measured.

[0320] The forces for extruding two-component reactive-resin system E4.1 containing the inventive compound (V) were compared with the force for extruding the comparison two-component reactive-resin systems F.1 and G4.1, which contain comparison compounds 1 and 2 respectively, at 0 C. and at 23 C. The measured results are compiled in Table 11.

TABLE-US-00011 TABLE 11 Results of the measurement of the forces for extruding two-component reactive-resin system E4.1 and comparison two-component reactive-resin systems F4.1 and G4.1 at 0 C. and 23 C. Comparison Two-component Comparison two-component reactive-resin two-component reactive-resin system reactive-resin system system E4.1 F4.1 G4.1 Force [N] 462.1 750.2 740.5 at 0 C. Force [N] 377.5 400.7 396.0 at 23 C.

[0321] The results in Table 11 show that the two-component reactive-resin system containing the inventive compound (V) exhibits a lower extrusion force both at 0 C. and at 23 C. than do the comparison two-component reactive-resin systems containing comparison compounds 1 and 2 respectively, wherein the differences at 0 C. are particularly evident.

[0322] This proves that the inventive compounds lead to lowering of the viscosity of reactive-resin master batches and thus of the corresponding reactive resins. The reactive-resin components produced therefrom also have lowered viscosity, which is reflected in a reduction of the extrusion forces.

[0323] Besides the lowering of the viscosity, the use of the inventive compounds leads to an increase of the load ratings of the cured fastening caulks.