US2005043430A1PendingUtilityA1

Photocurable adhesive composition and its use in the optical field

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Assignee: ESSILOR INTPriority: Apr 17, 2003Filed: Jun 7, 2004Published: Feb 24, 2005
Est. expiryApr 17, 2023(expired)· nominal 20-yr term from priority
Inventors:Steven WeberPeiqi JiangYassin TurshaniAref Jallouli
C08F 222/10C09J 4/00C08F 220/20G02B 1/041C08F 220/12C08L 2312/06C09J 133/14C08L 2666/02C08F 220/38B29C 66/81422B29C 65/1483B29C 66/81423B29C 66/7338B29C 66/301B29C 65/4845B29C 66/73921B29C 66/8322B29C 66/723B29C 66/545B29C 66/1122B29L 2011/0041B29C 66/8122B29C 66/71B29C 66/543B29C 65/1406B29C 65/1435B29C 66/73941B29C 66/81455B29C 66/81267
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Claims

Abstract

The invention concerns a photocurable adhesive composition comprising, based on total weight of photopolymerizable monomers and/or oligomers of the composition: 5 to 60 wt % of at least one mono or polyacrylate monomer or oligomer thereof (A); 5 to 50 wt % of at least one thio(meth)acrylate monomer or oligomer thereof (B); and 20 to 50 wt % of at least one aromatic dimethacrylate monomer or oligomer thereof (C); with the proviso that the composition does not contain a brominated monofuntional acrylate.

Claims

exact text as granted — not AI-modified
1 . A composition comprising, based on total weight of the photopolymerizable monomers and/or oligomers of the composition: 
 5 to 60 wt % of at least one mono or polyacrylate monomer or oligomer thereof (A);    5 to 50 wt % of at least one thio(meth)acrylate monomer or oligomer thereof (B); and    20 to 50 wt % of at least one aromatic dimethacrylate monomer or oligomer thereof (C);    with the proviso that the composition does not contain a brominated monofunctional acrylate.    
     
     
         2 . The composition of  claim 1 , comprising: 
 at least 15 wt % of (A);    at least 9 wt % of (B); and    at least 25 wt % of (C).    
     
     
         3 . The composition of  claim 1 , comprising: 
 20 to 60 wt % at least one mono or polyacrylate monomer or oligomer thereof (A);    20 to 50 wt % of at least one thio(meth)acrylate monomer or oligomer thereof (B); and    20 to 40 wt % based on the total weight of the photopolymerizable composition of at least one aromatic dimethacrylate monomer or oligomer thereof (C).    
     
     
         4 . The composition of  claim 1 , comprising 20 to 60 wt % of (A), 30 to 50 wt % of (B) and 20 to 40 wt % of (C).  
     
     
         5 . The composition of  claim 1 , comprising: 
 20 to 50 wt % of at least one mono or polyacrylate monomer or oligomer thereof (A);    30 to 50 wt % of at least one thio(meth)acrylate monomer or oligomer thereof (B); and    20 to 40 wt % of at least one aromatic dimethacrylate monomer or oligomer thereof (C).    
     
     
         6 . The composition of  claim 1 , comprising: 
 20 to 40 wt % of at least one mono or polyacrylate monomer or oligomer thereof (A);    35 to 45 wt % of at least one thio(meth)acrylate monomer or oligomer thereof (B); and    25 to 35 wt % of at least one aromatic dimethacrylate monomer or oligomer thereof (C).    
     
     
         7 . The composition of  claim 1 , wherein said at least one mono or polyacrylate monomer (A) has a calculated solubility parameter ranging from 8 to 12 (cal/cm 3 ) 1/2 .  
     
     
         8 . The composition of  claim 7 , wherein said at least one mono or polyacrylate monomer (A) has a calculated solubility parameter ranging from 8.5 to 11.5 (cal/cm 3 ) 1/2 .  
     
     
         9 . The composition of  claim 1 , wherein said at least one mono or polyacrylate monomer (A) has a molecular weight <500.  
     
     
         10 . The composition of  claim 9 , wherein said at least one mono or polyacrylate monomer (A) has a molecular weight ≦350.  
     
     
         11 . The composition of  claim 1 , wherein said at least one monomer (A) is a low refractive index monomer.  
     
     
         12 . The composition of  claim 1 , wherein said mono or polyacrylate monomer (A) is a non-aromatic mono or polyacrylate monomer.  
     
     
         13 . The composition of  claim 12 , wherein monomer (A) is diethyleneglycol diacrylate, triethyleneglycol diacrylate, tetraethyleneglycol diacrylate, neopentylglycoldiacrylate, 1,6-hexanediol diacrylate or tetrahydrofurfuryl acrylate.  
     
     
         14 . The composition of  claim 1 , wherein the at least one thio(meth)acrylate monomer (B) is a high refractive index monomer.  
     
     
         15 . The composition of  claim 1 , wherein the at least one thio(meth)acrylate monomer (B) is a monomer of formula:  
       
         
           
           
               
               
           
         
       
       wherein: 
 R is a linear or branched, monovalent or polyvalent, aliphatic hydrocarbon radical, or a monovalent or polyvalent aromatic group directly linked to the sulfur atom of the thio(meth)acrylate group(s) through an aromatic ring or by means of a linear alkyl chain, the radical R may include in its chain one or more of:  
                     
 R 1  is H or —CH 3 ; and  
 n is an integer from 1 to 6.  
 
     
     
         16 . The composition of  claim 1 , wherein the at least one aromatic dimethacrylate monomer (C) is an ethoxylated bisphenol-A monomer.  
     
     
         17 . The composition of  claim 1 , further comprising at least one photoinitiator.  
     
     
         18 . The composition of  claim 17 , wherein the photoinitiator represents 0, 1 to 5 parts by weight for 100 parts by weight of the polymerizable monomers and/or oligomers.  
     
     
         19 . The composition of  claim 1 , wherein, after curing, the adhesive composition has a refractive index of 1.53 to 1.65.  
     
     
         20 . A process comprising: 
 providing a thermoplastic material substrate having at least one main surface;    providing a support having an internal surface bearing a coating and an external surface;    depositing on the main surface of the substrate or on the coating a pre-measured amount of a curable adhesive composition comprising, based on total weight of photopolymerizable monomer and/or oligomers of the composition: 
 5 to 60 wt % of at least one mono or polyacrylate monomer or oligomer thereof, (A);  
 5 to 50 wt % of at least one thio(meth)acrylate monomer or oligomer thereof, (B); and  
 20 to 50 wt % of at least on aromatic dimethacrylate monomer or oligomer thereof, (C);  
   with the proviso that the composition does not contain a brominated monofuntional acrylate;    moving relatively to each other the substrate and the support to either bring the coating into contact with the curable adhesive composition or bring the curable adhesive composition into contact with the main surface of the substrate;    applying a sufficient pressure onto the external surface of the support so that the thickness of a final adhesive layer, once the curable adhesive composition has cured is less than 100 μm;    curing the layer of adhesive composition; and    withdrawing the support to recover a substrate with the coating adhered onto its main surface.    
     
     
         21 . The process of  claim 20 , wherein the photocurable adhesive composition comprises: 
 at least 15 wt % of (A);    at least 9 wt % of (B); and    at least 25 wt % of (C).    
     
     
         22 . The process of  claim 20 , wherein the photocurable adhesive composition comprises: 
 20 to 60 wt % at least one mono or polyacrylate monomer or oligomer thereof (A);    20 to 50 wt % of at least one thio(meth)acrylate monomer or oligomer thereof (B); and    20 to 40 wt % based on the total weight of the photopolymerizable composition of at least one aromatic dimethacrylate monomer or oligomer thereof (C).    
     
     
         23 . The process of  claim 20 , wherein the photocurable adhesive composition comprises 20 to 60 wt % of (A), 30 to 50 wt % of (B) and 20 to 40 wt % of (C).  
     
     
         24 . The process of  claim 20 , wherein the photocurable adhesive composition comprises: 
 20 to 50 wt % of at least one mono or polyacrylate monomer or oligomer thereof (A);    30 to 50 wt % of at least one thio(meth)acrylate monomer or oligomer thereof (B); and    20 to 40 wt % of at least one aromatic dimethacrylate monomer or oligomer thereof (C).    
     
     
         25 . The process of  claim 20 , wherein the photocurable adhesive composition comprises: 
 20 to 40 wt % of at least one mono or polyacrylate monomer or oligomer thereof (A);    35 to 45 wt % of at least one thio(meth)acrylate monomer or oligomer thereof (B); and    25 to 35 wt % of at least one aromatic dimethacrylate monomer or oligomer thereof (C).    
     
     
         26 . The process of  claim 20 , wherein the thermoplastic material of the substrate is a high refractive index material.  
     
     
         27 . The process of  claim 20 , wherein the thermoplastic material of the substrate is polycarbonate.  
     
     
         28 . The process of  claim 20 , wherein said at least one mono or polyacrylate monomer (A) has a calculated solubility parameters ranging from 8 to 12 (cal/cm 3 ) 1/2 .  
     
     
         29 . The process of  claim 28 , wherein said at least one mono or polyacrylate monomer (A) has a calculated solubility parameter ranging from 8.5 to 11.5 (cal/cm 3 ) 1/2 .  
     
     
         30 . The process of  claim 20 , wherein said at least one mono or polyacrylate monomer (A) has a molecular weight <500.  
     
     
         31 . The process of  claim 30 , wherein said at least one monomer (A) has a molecular weight ≦350.  
     
     
         32 . The process of  claim 20 , wherein said at least one monomer (A) is a low refractive index monomer.  
     
     
         33 . The process of  claim 20 , wherein said mono or polyacrylate monomer (A) is a non-aromatic mono or polyacrylate monomer.  
     
     
         34 . The process of  claim 33 , wherein monomer (A) is diethyleneglycol diacrylate, triethyleneglycol diacrylate, tetraethyleneglycol diacrylate, neopentylglycoldiacrylate, 1,6-hexanediol diacrylate and tetrahydrofurfuryl acrylate.  
     
     
         35 . The process of  claim 20 , wherein the said at least one thio(meth)acrylate monomer (B) is a high refractive index monomer.  
     
     
         36 . The process of  claim 20 , wherein the at least one thio(meth)acrylate monomer (B) is a monomer of formula:  
       
         
           
           
               
               
           
         
       
       wherein: 
 R is a linear or branched, monovalent or polyvalent, aliphatic hydrocarbon radical, or a monovalent or polyvalent aromatic group directly linked to the sulfur atom of the thio(meth)acrylate group(s) through an aromatic ring or by means of a linear alkyl chain, the radical R may include in its chain one or more of:  
                     
 R 1  is H or —CH 3 ; and  
 n is an integer from 1 to 6.  
 
     
     
         37 . The process of  claim 36 , wherein n is an integer from 1 to 3.  
     
     
         38 . The process of  claim 20 , wherein the at least one aromatic dimethacrylate monomer (C) is a ethoxylated bisphenol-A monomer.  
     
     
         39 . The process of  claim 20 , wherein the photopolymerizable adhesive composition further comprises at least one photoinitiator.  
     
     
         40 . The process of  claim 39 , wherein the photoinitiator represents 0.1 to 5 parts by weight for 100 parts by weight of the photopolymerizable monomers.  
     
     
         41 . The process of  claim 20 , wherein the substrate is a lens blank, and the main surface is a geometrically defined surface of the lens blank.  
     
     
         42 . The process of  claim 41 , wherein the support is made of polycarbonate.  
     
     
         43 . The process of  claim 41 , wherein the support is a flexible support part having an internal surface conformable to a geometrically defined surface of the lens blank when brought into contact therewith.  
     
     
         44 . The process of  claim 43 , wherein the flexible support is urged against the lens blank by means of an inflatable membrane.  
     
     
         45 . The process of  claim 20 , wherein the support is made of polycarbonate.  
     
     
         46 . The process of  claim 20 , wherein the support has a thickness of 0.3 to 1 mm.  
     
     
         47 . The process of  claim 20 , wherein the thickness of the final cured adhesive layer is less than 80 μm.  
     
     
         48 . The process of  claim 20 , wherein the thickness of the final cured adhesive layer is less than 50 μm.  
     
     
         49 . The process of  claim 20 , wherein the final cured adhesive layer has a refractive index of 1.53 to 1.65.  
     
     
         50 . The process of  claim 20 , wherein the exerted pressure ranges from 5 to 50 Psi (0.35 to 3.5 kgf/cm 3 ).  
     
     
         51 . The process of  claim 20 , wherein the coating comprises a hydrophobic top coat, an anti-reflective coating layer, an anti-abrasion coating layer, an impact resistant coating layer, a photochromic coating layer, a dying coating layer a polarized coating layer, a printed layer or a stack of two or more of these coating layers.  
     
     
         52 . The process of  claim 51 , wherein the coating has a thickness of 50 μm or less.  
     
     
         53 . The process of  claim 20 , wherein the substrate is a semi-finished lens having one face already provided with a coating.  
     
     
         54 . The process of  claim 53 , wherein the face already provided with a coating is the front face of the lens and the geometrically defined surface onto which the coating is transferred is the back surface of the lens.  
     
     
         55 . A process which comprises: 
 providing a thermoplastic material substrate having at least one main surface;    providing a mold part having an internal surface and an external surface;    depositing on the main surface of the substrate or on the internal surface of the mold part a pre-measured amount of a curable adhesive composition comprising, based on the total weight of photopolymerizable monomers and/or oligomers of the composition: 
 5 to 60 wt % of at least one mono or polyacrylate monomer or oligomer thereof (A);  
 5 to 50 wt % of at least one mono or polyacrylate monomer or oligomer thereof (B); and  
 20 to 50 wt % of at least one mono or polyacrylate monomer or oligomer thereof (C);  
   with the proviso that the composition does not contain a brominated monofunctional acrylate;    moving relatively to each other the substrate and the mold part to either bring the internal surface of the mold part or the main surface of the substrate in contact with the curable adhesive composition;    applying a sufficient pressure onto the external surface of the mold part to uniformly spread the curable adhesive composition and form a uniform layer, which, when cured, has a thickness of at least 200 μm.    curing the layer of adhesive composition; and    withdrawing the mold parts to recover the substrate overmolded with a cured layer of the curable adhesive composition.    
     
     
         56 . The process of  claim 55 , wherein the photocurable adhesive composition comprises: 
 at least 15 wt % of (A);    at least 9 wt % of (B); and    at least 25 wt % of (C).    
     
     
         57 . The process of  claim 55 , wherein the photocurable adhesive composition comprises: 
 20 to 60 wt % at least one mono or polyacrylate monomer or oligomer thereof (A);    20 to 50 wt % of at least one thio(meth)acrylate monomer or oligomer thereof (B); and    20 to 40 wt % based on the total weight of the photopolymerizable composition of at least one aromatic dimethacrylate monomer or oligomer thereof (C).    
     
     
         58 . The process of  claim 57 , wherein the photocurable adhesive composition comprises 20 to 60 wt % of (A), 30 to 50 wt % of (B) and 20 to 40 wt % of (C).  
     
     
         59 . The process of  claim 55 , wherein the photocurable adhesive composition comprises: 
 20 to 50 wt % of at least one mono or polyacrylate monomer or oligomer thereof (A);    30 to 50 wt % of at least one thio(meth)acrylate monomer or oligomer thereof (B); and    20 to 40 wt % of at least one aromatic dimethacrylate monomer or oligomer thereof (C).    
     
     
         60 . The process of  claim 55 , wherein the photocurable adhesive composition comprises: 
 20 to 40 wt % of at least one mono or polyacrylate monomer or oligomer thereof (A);    35 to 45 wt % of at least one thio(meth)acrylate monomer or oligomer thereof (B); and    25 to 35 wt % of at least one aromatic dimethacrylate monomer or oligomer thereof (C).    
     
     
         61 . The process of  claim 55 , wherein a coating to be transferred is applied to the internal surface of the mold part before depositing the curable adhesive composition.  
     
     
         62 . The process of  claim 55 , wherein the overmolded cured layer of curable adhesive composition has a thickness of at least 500 μm.  
     
     
         63 . A process comprising: 
 depositing a pre-measured amount of a photocurable adhesive composition on a main surface of a first part made of thermoplastic material;    bringing into contact the deposited photocurable adhesive composition with a main surface of a second part made of thermoplastic material;    pressing the first and second parts against each other to uniformly spread the curable adhesive composition to form a uniform thin layer; and photocuring the thin layer to obtain a laminated article, wherein the photocurable adhesive composition comprises, based on total weight of photopolymerizable monomers and/or oligomers of the composition: 
 5 to 60 wt % of at least one mono or polyacrylate monomer or oligomer thereof (A);  
 5 to 50 wt % of at least one thio(meth)acrylate monomer or oligomer thereof (B); and  
 20 to 50 wt % of at least one aromatic dimethacrylate monomer or oligomer thereof (C);  
 with the proviso that the composition does not contain a brominated monofuntional acrylate.  
   
     
     
         64 . The process of  claim 63 , wherein the article is an ophthalmic lens.

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