Source: http://www.google.com/patents/US7385020?dq=6289460
Timestamp: 2014-09-22 01:20:08
Document Index: 264888211

Matched Legal Cases: ['art 1', 'art 2', 'art 1', 'art 1', 'art 2', 'art 1', 'art 1', 'art 2', 'art 1']

Patent US7385020 - Pressure sensitive adhesives; improved peel, shear and high temperature ... - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign in<nobr>Advanced Patent Search</nobr>PatentsA pressure sensitive adhesive composition comprising a 2-octyl (meth)acrylate/(meth)acrylic acid copolymer and a crosslinking agent is described. The adhesive composition may be derived from renewable resources and provides good peel, shear and high temperature stability....http://www.google.com/patents/US7385020?utm_source=gb-gplus-sharePatent US7385020 - Pressure sensitive adhesives; improved peel, shear and high temperature stabilityAdvanced Patent SearchPublication numberUS7385020 B2Publication typeGrantApplication numberUS 11/549,162Publication dateJun 10, 2008Filing dateOct 13, 2006Priority dateOct 13, 2006Fee statusPaidAlso published asCN101517026A, CN101517026B, DE602007005016D1, EP2076577A1, EP2076577B1, US7893179, US20080087196, US20080213584, WO2008046000A1Publication number11549162, 549162, US 7385020 B2, US 7385020B2, US-B2-7385020, US7385020 B2, US7385020B2InventorsKelly S. ANDERSON, Kevin M. Lewandowski, Duane D. Fansler, Babu N. Gaddam, Eugene G. JosephOriginal Assignee3M Innovative Properties CompanyExport CitationBiBTeX, EndNote, RefManPatent Citations (34), Non-Patent Citations (2), Referenced by (18), Classifications (11), Legal Events (4) External Links: USPTO, USPTO Assignment, EspacenetPressure sensitive adhesives; improved peel, shear and high temperature stabilityUS 7385020 B2Abstract A pressure sensitive adhesive composition comprising a 2-octyl (meth)acrylate/(meth)acrylic acid copolymer and a crosslinking agent is described. The adhesive composition may be derived from renewable resources and provides good peel, shear and high temperature stability.
BACKGROUND Pressure sensitive adhesives (PSAs) are known to possess properties including the following: (1) aggressive and permanent tack, (2) adherence with no more than finger pressure, (3) sufficient ability to hold onto an adherend or substrate, and (4) sufficient cohesive strength to be removed cleanly from the adherend. Materials that have been found to function well as PSAs include polymers designed and formulated to exhibit the requisite viscoelastic properties resulting in a desired balance of tack, peel adhesion, and shear holding power. PSAs are characterized by being normally tacky at room temperature (e.g., 20� C.). PSAs do not embrace compositions merely because they are sticky or adhere to a surface.
SUMMARY The present invention provides an adhesive composition derived from renewable resources. In particular, the present invention provides an adhesive composition derived, in part, from plant materials. In some embodiments, the present invention further provides an adhesive article, wherein the substrate or backing is also derived from renewable resources. The pressure sensitive adhesive composition comprises a 2-octyl (meth)acrylate/(meth)acrylic acid copolymer and a crosslinking agent. The pressure sensitive adhesive of the invention comprises the reaction product of the same. As used herein (meth)acrylate or (meth)acrylic is inclusive of methacrylate and acrylate.
DETAILED DESCRIPTION The adhesive composition comprises
Preparative Example 1 2-octyl acrylate A mixture of 2-octanol (268.51 grams, 2.1 mol), AA (183.75 grams, 2.6 mol), p-toluenesulfonic acid monohydrate (5.00 grams, 26 mmol), toluene (250 grams) and phenothiazine (1.0 grams) was heated to reflux. Water was separated from the toluene/water azeotrope using a Dean Stark distillation trap. After six hours at reflux a total of 37 milliliters of water was collected in the trap. The reaction mixture was washed with 1 Molar aqueous sodium hydroxide (200 milliliters), then concentrated under reduced pressure. The remaining oil was distilled under reduced pressure (65-67� C. at 2 mmHg) to give the product as a colorless oil. (Yield: 248.6 grams)
Examples 1-2 and Comparative Examples C1-C2 Part 1 Solution Polymerizations For Examples 1 and 2 solution co-polymerizations of 2-OA with AA were performed by combining the materials shown in Table 1 in a glass jar, purging with nitrogen for 15 minutes, and sealing the jars. The jars were placed in a 60� C. water bath oscillating at 110 rpm for 18-20 hours. The same procedure was used for Comparative Examples C1 and C2 except that IOA was used instead of 2-OA. The molecular weight (Mw) and PDI of the resulting polymers were determined using GPC and the Inherent viscosities (IV) were measured using a #50 viscometer tube at a solution concentration of 0.5 grams/deciliter in THF. These data are presented in Table 1 below.
Part 2 Preparation and Testing of Tape Samples To prepare tape samples, 10.0 grams of the solutions prepared in Table 1 above were placed into a vial along with the corresponding amount of B-212 chemical crosslinker. The amount of B-212 in the formulations was varied from 0 to 0.3 weight % as shown in Table 2. The resulting solutions were coated with a knife coater onto a primed PET film. The knife height was set to 102-127 micrometers (4-5 mils) above the polyester to get a coating that is about 25 micrometers (1 mil) when dried. The coated solution was allowed to air dry for 2 minutes to remove the solvent. The coated PET sheet was then taped onto a thin aluminum panel and placed into an oven at 70� C. for 5 minutes. After the sample was removed from the oven, a release liner was placed on the adhesive to protect the coating. The coated films were allowed to equilibrate in a constant temperature/constant humidity (23� C./50% Relative Humidity) room for 24 hours prior to testing. The tape testing was performed as described in the test methods above, the data are presented in Table 2.
Examples 3-5 and Comparative Examples C3-C5 Part 1 Solution Polymerizations For Examples 3-5 solution co-polymerizations of 2-OA with AA were performed by combining the materials shown in Table 3 in a glass jar, purging with nitrogen for 15 minutes, and sealing the jars. The jars were placed in a 60� C. water bath oscillating at 110 rpm for 24 hours. The same procedure was used for Comparative Examples C3-C5 except that IOA was used instead of 2-OA. The Inherent viscosities (IV) were measured using a 50 viscometer tube at a solution concentration of 0.5 grams/deciliter in THF. Brookfield viscosity was measured at room temperature using a Brookfield viscometer (measured in centipoise and converted to Pascal Seconds). These data are presented in Table 3 below.
Examples 6-7 and Comparative Examples C6-C7 Part 1 Solution Polymerizations For Examples 6-7 solution co-polymerizations of 2-OA with AA were performed as described in Examples 1-2 with the weight ratios of monomers shown in Table 4. The same procedure was used for Comparative Examples C6-C7 except that IOA was used instead of 2-OA.
Part 2 Preparation and Testing of Thermal Stability Samples To prepare thermal stability testing samples, solution polymers with varying compositions were prepared following the general procedure described in Part 1 above. The polymer solutions were then placed into a vial along with the corresponding amount of B-212 chemical crosslinker. The weight % of B-212 is shown in Table 4. This solution was coated with a knife coater onto a silicone release liner. The knife height was set to 254 micrometers (10 mils) above the liner. The coated solution was allowed to air dry for 5 minutes to remove the solvent. The coated film was then taped onto a thin aluminum panel and placed into an oven at 150� C. for 2 minutes. The coated adhesives were allowed to equilibrate in constant temperature/constant humidity (CT/CH) room for 24 hours prior to testing. To determine the degradation onset temperature, a sample of the adhesive (approximately 20-30 milligrams) was analyzed using a TA Instruments TGA 2950 Thermogravimetric Analyzer (TA Instruments Inc., New Castle, Del.). The sample was subjected to a temperature ramp from room temperature to 500� C. at a rate of 10� C./min. The onset point of degradation was then determined from the sample weight versus temperature plot (calculated using the TA Instruments Universal Analysis software). In addition, the thermal stability of the adhesives at 150� C. and 175� C. were determined. Using the TA Instruments TGA 2950 Thermogravimetric Analyzer, the sample temperature was increased from room temperature to the desired set point (either 150� C. or 175� C.) at 200� C./min and kept at the set point for 3.5 hrs. The sample weight was monitored and the % weight loss after 3.5 hrs was determined based on the original weight of the sample. The data are presented in Table 4.
Examples 8-11 Part 1 Solution Polymerizations For Examples 8-11 solution co-polymerizations of 2-OA with AA were performed as described in Examples 1-2 above with the weight ratios shown in Table 5.
Part 2 Preparation and Testing of Tape Samples To prepare tape samples, portions of the solutions prepared in Part 1 above were placed into a vial along with the corresponding amount of B-212 chemical crosslinker and SANTICIZER 141 plasticizer as shown in Table 5. These mixtures were coated on PLA film with a knife coater using the method described in Examples 1-2. The coated solution was allowed to air dry for 2 minutes to remove the solvent. The coated film was then taped onto a thin aluminum panel and placed into an oven at 70� C. for 5 minutes. A release liner was then placed over the coated adhesives and they were allowed to equilibrate in constant temperature/constant humidity (CT/CH) room for 24 hours prior to testing. Shear strength testing on both stainless steel (SS) and fiber board (FB) substrates was performed as described in the test methods above and the results are shown in Table 5.
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