Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
  • C09J11/02—Non-macromolecular additives
  • C09J11/06—Non-macromolecular additives organic
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
  • C09J133/04—Homopolymers or copolymers of esters
  • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
  • C09J133/08—Homopolymers or copolymers of acrylic acid esters
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
  • C08K5/39—Thiocarbamic acids; Derivatives thereof, e.g. dithiocarbamates
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
  • C08K5/39—Thiocarbamic acids; Derivatives thereof, e.g. dithiocarbamates
  • C08K5/405—Thioureas; Derivatives thereof

Definitions

• Curable adhesive and sealant compositions oftentimes rely on curatives to make them commercially attractive options for end users. Curable adhesive and sealant compositions come in one part formats, two part formats and two step formats depending on the performance profile they are designed to meet and the constituents used to prepare the compositions. Anaerobic
• adhesives are prominent one part compositions and generally are well-known. See e.g. , R.D. Rich, "Anaerobic Adhesives" in
• anaerobic adhesives ordinarily include a free-radically polymerizable acrylate ester monomer, together with a peroxy initiator and an inhibitor component. Oftentimes, such anaerobic adhesive compositions also contain accelerator components to increase the speed with which the composition cures.
• Anaerobic cure-inducing compositions ordinarily used in commercial anaerobic adhesive and sealant compositions to induce and accelerate cure ordinarily include saccharin, toluidines, such as N,N-diethyl-p-toluidine ("DE-p-T”) and N,N-dimethyl-o- toluidine (“DM-o-T”), acetyl phenylhydrazine ("APH”) , maleic acid, and quinones, such as napthaquinone and anthraquinone. See e.g. U.S. Patent Nos. 3,218,305 (Krieble) , 4,180,640 (Melody), 4,287,330 (Rich) and 4,321,349 (Rich).
• Benzoylthiourea or benzoylthiourethane derivatives for use as accelerators in primers for two step adhesive systems are provided.
• benzoylthiourethane derivatives may be within general structure I
• Z is 0 or N-R, where R is selected from hydrogen, alkyl, alkenyl, hydroxyalkyl, hydroxyalkenyl, carbonyl, alkylene
• R' is a direct bond attaching to the phenyl ring;
• R' is selected from hydrogen, alkyl, alkenyl, cycloalkyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene- or alkenylene-ether, carbonyl, alkylene (meth)acrylate, carboxyl, nitroso or sulfonato;
• X is halogen, alkyl, alkenyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl; and
• Y is -SO 2 NH-, -CONH-, -NH-, and -PO(NHCONHCSNH 2 )NH-; and n is 0 or 1 and m is 1 or 2.
• R and R' are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene
• benzoylthiourethane derivatives may be within structures II or II3 ⁇ 4, respectively
• R, R' , Z, X, Y, and n are as defined above.
• R, X, Y, and n are as defined above, and X' is defined as X.
• benzoylthiourethane derivatives within structure I may be a bis version, where R' is a linker. That is,
• R, R' , X, Y, and n are as defined above, and m is 2.
• benzoylthiourea or benzoylthiourethane derivatives act to accelerate cure of curable compositions and provide adhesive systems with good cure through volume.
• the present invention will be more fully appreciated by a reading of the "Detailed Description", and the illustrative examples which follow thereafter.
• FIG. 1 depicts a rheometry plot of complex shear modulus versus time in a two step adhesive system comparing benzoylthiourea as a primer with LOCTITE 7649.
• FIG. 2 depicts an exploded perspective view of a cut away of a liquid crystal display device, illustrating three separate application layers of a LOCA between one or more of glass or PET, an ITO electrode, and an LCD panel.
• FIG. 3 depicts a plot of CHP concentration (as weight percent in a LOCA) versus cure time (in minutes) for various BTU derivatives as a primer.
• FIG. 4 depicts a plot of cure time (in minutes) versus CHP concentration (as weight percent in a LOCA) for BOTU as a primer.
• FIG. 5 depicts a plot of LOCA thickness (in mils) versus cure time (in minutes) for each of 2% and 3% CHP additions to the LOCA using BMTU as a primer.
• a primer uses cure accelerators within structure
• Z is O or N-R, where R is selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene
• X is halogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, alkylene- or alkenylene-ether, alkylene (meth) acrylate, carbonyl, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl; and
• Y is -SO 2 NH-, -CONH-, -NH-, and -PO(NHCONHCSNH 2 )NH-; and n is 0 or 1 and m is 1 or 2.
• R and R' are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene
• Y is -SO 2 NH-, -CONH-, -NH-, and
• inventive cure accelerators may be within structures XI and IIA respectively
• R, R' , X, Y, and n are as defined above.
• R f X, Y, and n are as defined above, and X' is defined as X.
• inventive cure accelerators include
• benzoylthiourea or benzoylthiourethane derivatives may be used as an accelerator in a primer (in a solution, suspension or dispersion, together with an appropriate delivery vehicle or carrier) in two step adhesive systems, where the benzoylthiourea or benzoylthiourethane derivatives are applied first onto a portion of substrate to be bonded followed by the anaerobically curable composition or applied after the composition has been applied.
• a primer in a solution, suspension or dispersion, together with an appropriate delivery vehicle or carrier
• compositions and as primers in an appropriate delivery vehicle or carrier are compositions and as primers in an appropriate delivery vehicle or carrier.
• the invention provides a process for preparing a reaction product from a curable composition, comprising the steps of:
• R and R' are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene
• Y is -SO 2 NH-, -CONH-, -NH-, and
• R and R' are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene
• Y is -SO 2 NH-, -CONH-, -NH-, and
• composition comprising a (meth) acrylate component and an oxidant to that desired sustrate surface
• the invention provides a process for preparing a reaction product from a curable composition, comprising the steps of:
• composition comprising a (meth) acrylate component and an oxidant to a desired substrate surface
• R and R' are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene
• Y is -SO 2 NH-, -CONH-, -NH-, and
• R and R' are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene
• Y is -SO 2 NH-, -CONH-, -NH-, and
• the invention provides a process for preparing a reaction product from a curable composition, comprising the steps of:
• composition comprising a (meth) acrylate
• R and R' are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene
• Y is -SO 2 NH-, -CONH-, -NH-, and
• R and R' are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene
• Y is -SO 2 NH-, -CONH-, -NH-, and
• the invention provides a process for preparing a reaction product from a curable composition, comprising the steps of:
• composition comprising a (meth) acrylate component and a compound within structures I or IA
• R and R' are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene
• Y is -SO 2 NH-, -CONH-, -NH-, and
• R and R' are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene
• Y is -SO 2 NH-, -CONH-, -NH-, and
• (meth) acrylate component in the two step adhesive systems may be chosen from a wide variety of materials, such as these
• Additional (meth) acrylate monomers suitable for use herein include polyfunctional (meth) acrylate monomers, such as, but not limited to, di-or tri-functional (meth) acrylates like polyethylene glycol di (meth) acrylates, tetrahydrofuran
• HPMA hexanediol di (meth) acrylate
• TMPTMA trimethylol propane tri (meth) acrylate
• dimethacrylate triethylene glycol dimethacrylate (“TRIEGMA”)
• TRIEGMA triethylene glycol dimethacrylate
• tetraethylene glycol dimethacrylate dipropylene glycol
• dimethacrylate di- (pentamethylene glycol) dimethacrylate, tetraethylene diglycol diacrylate, diglycerol tetramethacrylate, tetramethylene dimethacrylate, ethylene dimethacrylate, neopentyl glycol diacrylate, trimethylol propane triacrylate and bisphenol- A mono and di (meth) acrylates, such as ethoxylated bisphenol-A (meth) acrylate (“EBIPMA”) , and bisphenol-F mono and
• di (meth) acrylates such as ethoxylated bisphenol-F
• Still other (meth)acrylate monomers that may be used herein include silicone (meth) acrylate moieties (“SiMA”), such as those taught by and claimed in U.S. Patent No. 5,605,999 (Chu) , the disclosure of which is hereby expressly incorporated herein by reference.
• SiMA silicone (meth) acrylate moieties
• the (meth) acrylate component should comprise from about 10 to about 90 percent by weight, such as about 60 to about 90 percent by weight, based on the total weight of the adhesive system (excluisve of the carrier vehicle, if the carrier vehicle evaporates prior to assembly and/or cure) .
• Additional components may be included in traditional curable compositions to alter the physical properties of either the curable compositions or the reaction products thereof.
• maleimide components may be included to modify the physical property and/or cure profile of the formulation and/or the strength or temperature resistance of the cured adhesive.
• the maleimide, coreactant, reactive diluent, plasticizer, and/or mono- or poly-hydroxyalkanes may be present in an amount within the range of about 1 percent to about 30 percent by weight, based on the total weight of the composition.
• the curable compositions may also include other ingredients
• a number of well-known initiators of free radical polymerization are typically incorporated into the curable compositions including, without limitation,
• hydroperoxides such as cumene hydroperoxide ⁇ "CHP", para- menthane hydroperoxide, t-amyl hydroperoxide, 1,1,3,3- tetramethylbutyl hydroperoxide and t-butyl hydroperoxide ("TBH”) .
• peroxides include t-butyl perbenzoate, benzoyl peroxide, dibenzoyl peroxide, 1, 3-bis (t-butylperoxyisopropyl) benzene, diacetyl peroxide, butyl 4, 4-bis (t-butylperoxy) valerate, p- chlorobenzoyl peroxide, cumene hydroperoxide, t-butyl cumyl peroxide, t-butyl perbenzoate, di-t-butyl peroxide, dicumyl peroxide, 2, 5-dimethyl-2, 5-di-t-butylperoxyhexane, 2, 5-dimethyl- 2, 5-di-t-butyl-peroxyhex-3-yne, 4-methyl-2, 2-di-t- butylperoxypentane and combinations thereof.
• Such oxidants are typically employed in the range of from about 0.1 to about 10 percent by weight, based on the total weight of the composition, with about 1 to about 5 percent by weight being desirable.
• Stabilizers and inhibitors may also be employed to control and prevent premature oxidant decomposition and polymerization of the curable compositions.
• chelating agents such as the tetrasodium salt of ethylenediamine tetraacetic acid (“EDTA”)] to trap trace amounts of metal
• chelators may ordinarily be present in the compositions in an amount from about 0.001 percent by weight to about 0.1 percent by weight, based on the total weight of the composition.
• the benzoylthiourea or benzoylthiourethane derivatives may be used as cure accelerators in amounts of about 0.1 to about 5 percent by weight, such as about 1 to about 2 percent by weight, based on the total weight of the composition.
• Other agents such as thickeners, non-reactive plasticizers, fillers, toughening components (such as elastomers and rubbers), and other well-known additives may be incorporated therein where the art-skilled believes it would be desirable to do so.
• the adhesive system may be prepared using conventional methods which are well known to those persons of skill in the art.
• the components of the curable composition may be mixed together in any convenient order consistent with the roles and functions the components are to perform in the
• the two step adhesive system may be used to bond a variety of substrates to perform with the desired benefits and advantages described herein. For instance, appropriate
• substrates may be constructed from steel, brass, copper,
• benzoylthiourea or benzoylthiourethane derivatives may be used in two-step adhesive systems, where exposure to radiation in the electromagnetic spectrum may be used to initiate cure, with cure continuing in those regions of the bond line that are not accessible (or have limited access) to such radiation, such as where opaque substrates are to be bonded. This is known as shadow curing.
• a secondary cure mechanism to affect polymerization in the unirradiated areas is often used, particularly when opaque substrates are to be bonded as noted above.
• One such secondary cure mechanism used in the past relies upon the addition to the compositions of heat-activated peroxides.
• heat-activated peroxides ordinarily use temperatures in excess of 100°C to initiate polymerization, which is undesirable particularly when heat-sensitive components are involved.
• Isocyanates which are moisture reactive, have been used in the past to provide such a secondary cure. Health and environmental concerns over the use of isocyanates have limited their acceptance.
• Moisture curable silicones have also been used to impart shadow cure properties to warble compositions. Long cure periods required to build the adhesive strength make them a less appealing approach.
• a primer of the so- described benzoylthiourea or benzoylthiourethane derivatives may be used to cure the adhesive composition through the bond line.
• the primer is applied as a solution, dispersion or emulsion of the benzoylthiourea or benzoylthiourethane derivative in a suitable carrier.
• benzoylthiourethane derivative is itself a liquid, it may be applied neat.
• the primer is applied to at least a peripheral portion of the underside of the touch panel of a hand held display device, which when assembled will not have appreciable visibility to a light source used to cure the adhesive with which the accelerator is to be used.
• LOCA optically clear adhesive
• FIG. 2 shows an exploded perspective view of the construction of a liquid crystal display module.
• a liquid crystal display module may be used to fabricate television sets, computer monitors, computer tablets and mobile phones, for instance.
• three instances of LOCA composition placement may be found: one between a liquid crystal display panel and aglass substrate; one between a glass substrate (the same glass substrate referred to above) and an indium tin oxide-coated electrode; and one between a glass or polyethylene terephthalate substrate and an ITO-coated electrode (the same ITO-coated electrode referred to above) .
• Benzoyl isothioeyanate was prepared as a starting material for benzoyl thiourea and derivates thereof.
• RBF three-neck round-bottom flask
• solid ammonium thiocyanate (16.9 g, 0.22 mol) and dichloromethane (100 mL) .
• the stirred mixture was cooled in an ice-water bath to a temperature of about 10-15°C.
• the RBF was changed to include a sealed glass-fritted bubbler system connected to an ammonia gas supply and an exit bubbler-scrubber system.
• To the clear cold reaction mixture (controlled at a temperature below 30°C with an external ice- water bath) was slowly purged ammonia gas. During the addition, ammonia was consumed and the reaction mixture slowly became pale and cloudy/milky in appearance. The mixture was allowed to warm to room temperature, and stirring continued for an additional hour after ammonia addition ceases. Nitrogen gas was then reintroduced into the system to purge residual ammonia gas. The resulting solid is collected by vacuum filtration and washed with additional dichloromethane to provide a slightly yellow solid, which was recrystallized from ethanol. The solid was then dried to a constant weight in vacuo at a temperature of 50°C and a pressure of ⁇ 1 mTorr. The resulting solid was observed to have a melting point of 171.62°C, as determined by DSC.
• BMTU Bangoyl Morpholine Thiourea
• BTDEU Benzoyl Thiodiethylurea
• the reaction mixture was then concentrated in -vacuo at a temperature of 40°C to provide a white solid.
• the solid was dried to constant weight in vacuo at a temperature of 50°C and a pressure of ⁇ 1 mTorr in a 97% yield.
• the solid was dried to constant weight in vacuo at a temperature of 50°C and a pressure of ⁇ 1 mTorr in a 93% yield. The solid was determined to have a melting point of 143.6°C.
• reaction mixture was then concentrated in vacuo at a temperature of 40°C to provide a white solid.
• the solid was dried to constant weight in vacuo at a temperature of 50°C and a pressure of ⁇ 1 mTorr in a 97% yield.
• reaction mixture was stirred overnight at room temperature before it was concentrated in vacuo at a temperature of 40°C to yield a white solid that was further dried to constant weight in vacuo at a temperature of 50°C and a pressure of ⁇ 1 mTorr.
• the organic phase was separated, washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo at a temperature of 40°C to yield a pale powdery (waxy) solid.
• the solid was dried to constant weight in vacuo at 40°C and ⁇ 1 mTorr (99%) .
• reaction mixture was then concentrated in vacuo at a temperature of 40°C to provide a yellow solid.
• the solid was dried to constant weight in vacuo at a temperature of 50°C and a pressure of ⁇ 1 mTorr in a 83% yield.
• BTU-HEMA Benzoyl Thiourea Hydroxyethyl Methacrylate
• Saccharin (0.5 g) and acetyl phenylhydrazine (0.5 g) were dissolved in 2-hydroxyethyl methacrylate (7.3 g) and acrylic acid (2.45 g) to form a solution, which was added to urethane methacrylate resin (87.99 g) .
• CHP (1 g) was also added to the composition to form the adhesive part of the two step system.
• LOCTITE 7649 was used as a control.
• LOCTITE 7649 consists of a copper salt and an aliphatic amine in acetone.
• Each primer was applied onto a pair of two aluminum plates in sufficient quantity to cover the inwardly facing surface of the plates; this typically required about 3 drops for a 8 mm diameter plate.
• Each pair of aluminum plates was then loaded onto a Physica MCR301 rheometer, and the gap between them was zeroed. As a primer-less control, the plates were loaded and the gap zeroed without the application of any primer.
• the top plate was withdrawn to a distance of 75 mm, and the adhesive part was loaded onto the bottom plate. The top plate was then lowered to the specified gap.
• the BTU-primed stainless steel substrates showed a fixture time of less than 1 hour across 500 micron gap stainless steel substrates.
• the fixture time was reduced to about 20 minutes on mated GMBS substrates with the same gap.
• LOCTITE 326 showed virtually no loss in strength from 0 to 500 micron gap, whether after one hour room temperature cure or 24 hours room temperature cure.
• BTU derivatives as primers were also evaluated.
• compounds A-1 were evaluated as primers, as shown and described below.
• BTU derivatives match or even outperform BTU as a primer in two step adhesive systems at zero gap and even at a gap of 250 microns, BTU itself still stands out at a gap of 500 microns.
• LOCA liquid optically clear adhesive
• LOCA compositions used here are available commercially from Henkel Corporation, Rocky Hill, Connecticut, under the trade names LOCTITE 3191, 3192, 3193, 3195, and 3196.
• LOCTITE 3195 contains polymerizable (meth) acrylated rubber resins with a molecular weight of up to 100,000 and IRGACURE 184
• a hydroperoxide-based oxidizing agent here CHP, was added in varying amounts, up to 10% based on the
• (meth) acrylated rubber resins (meth) acrylated rubber resins.
• the primer here was chosen from one of BTU, BOTU, BCHTU, BTDEU, BMTU, JEFFAMINE BTU, p-TSI TU, and BPHTU and employed as a 5% solution in an acetone/isopropanol solvent mixture.
• FIG. 3 the effect of the CHP level on shadow cure profiles is shown for BMTU, BOTU, BCHTU and BTDEU as primers.
• a primer of a pre-determined volume was applied onto a glass substrate (dimensions: 1" x 4") in an amount of about 0.3 ml and allowed to air dry for about 10-15 minutes.
• a 2 mil thick layer of the LOCA composition was then applied on another glass slide.
• the primer coated glass substrate was brought into contact with a second glass substrate previously coated with the LOCA composition.
• the total contact area where the primer and the LOCA composition layer are in contact is between 1" x 2".
• Each substrate assembly was then allowed to cure for various predetermined times before being subjected to adhesion evaluation in shear mode with a known weight (100 grams) .
• Each primer was applied to a glass slide in an amount of about 0.3 ml and allowed to air dry for about 10-15 minutes. A 2 mil thick layer of the LOCA composition was then applied on another glass slide.
• BOTU was selected to demonstrate the primer efficacy at various usage levels and various cure time periods.
• the primer usage level was varied by changing the concentration.
• LOCTITE 3195 with 3% by weight cumene hydroperoxide was used as the LOCA composition at a 2 mil thickness.
• the shadow cure results with various levels of BOTU primer are shown in the table below. More specifically, Sample Nos. 7-1 through 7-6 used respectively 5.0ft, 2.5%, 1.25%, 0.63%, 0.31% and 0.15%.
• BMTU was selected to demonstrate primer effectiveness for shadow cure at various thicknesses of adhesive layer.
• BMTU was used as a 5% solution in an acetone/isopropanol solvent mixture.
• the LOCA composition used here was as above.
• the adhesive thickness was varied from direct contact to 10 mils and the cure time was varied too. The variables and results are shown below in the table.
• BMTU was also used to establish a shadow cure profile with various levels of the cumene-hydroperoxide oxidizing agent in the LOCA composition. More specifically, Sample Nos. 3195-7 to 3195-11 had respectively 0%, 0.5%, 1%, 2% and 3% CHP. The base LOCA composition and the primer concentration was used as before. The results are shown below in the table.
• BTU derivatives ⁇ BMTU, BOTU, and BCHTU — were used as a primer with cumene hydroperoxide-containing LOCA compositions.
• Each LOCA composition was applied to a glass substrate at a thickness of 2 mil.
• the table below shows the shadow cure profiles of five noted LOCA compositions with the three noted BTU primers.
• FIGs. 4 and 5 also shows the benefits of certain benzoylthiourea derivatives as primers together with oxidant-containing LOCA compositions on cure time and cure through volume, respectively.
• adhesive compositions based on (meth) acrylated silicones were evaluated in a two-step adhesive system with BTU derivatives as primers.
• a series of SILMER-branded reactive silicones available commercially from Siltech) , were used to assess the effectiveness of the BTU derivatives as primers for the acrylate functional silicone pre-polymers .

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