Adhesives and related methods
View Patent ↗Cure in place pressure sensitive adhesive compositions are described that comprise one or more of a bodying component, a structural diluent, a radical diluent as well as additives such as crosslinkers, external catalysts, photoinitiators and stabilizers/process aids. The bodying component can be acrylic or non-acrylic.
1. A cure in place liquid comprising:
5-50 wt % of a bodying component comprising a pre-polymerized acrylic block base polymer having a molecular weight (Mw) of 5,000 to 1,000,000, the acrylic block base polymer comprising two functional end segments and one non-reactive middle segment, the reactive segments include one or more monomers of the non-reactive segment;
50-95 wt % of at least one structural diluent;
0.01-10 wt % of a curative; and
0-10 wt % stabilizer/process aid.
2. The cure in place liquid of claim 1 wherein the curative is selected from the group consisting of thermal catalysts, base catalysts, photoinitiators, radical initiators, and UV radical photoinitiators.
3. The cure in place liquid of claim 1 wherein the curative is a thermal catalyst.
4. The cure in place liquid of claim 1 wherein the curative is activatable by at least one of radiation, heat, moisture, pressure, ultrasound, exposure to chemical agents, and combinations thereof.
5. The cure in place liquid of claim 1 wherein the acrylic block base polymer has a Mw of 15,000 to 250,000.
6. The cure in place liquid of claim 5 wherein the acrylic block base polymer has a Mw of 15,000 to 100,000.
7. The cure in place liquid of claim 1 wherein the structural diluent is selected from the group consisting of 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate (S-21), Bis[(3,4-epoxycyclohexyl)methyl]adipate (S-28), difunctionalbisphenol A/epichlorohydrin derived liquid epoxy resin (Epon 828), Bisphenol A epoxy resin having a weight per epoxide of 235-263 g/eq as measured by ASTM D1652 (Epon 834), beta-(3,4-epoxycyclohexyl)ethyltrimethoxysilane (A-186), gamma-glycidoxypropyltrimethoxysilane (A-187), glycidyl ester of neodecanoic acid (EP-10), isocyanate-functional urethane acrylate (Desmolux D100), isocyanate-bearing urethane acrylate (Desmolux D200), aliphatic polyisocyanate (low-viscosity hexamethylenediisocyanate (HDI) biuret) (Desmodur N3200), aliphatic polyisocyanate (hexamethylenediisocyanate (HDI) biuret) (Desmodur N100), aliphatic polyisocyanate (hexamethylenediisocyanate (HDI) trimer) (Desmodur N3300), poly(propylene oxide) (PPO) oligomer having a molecular weight (Mw) of less than 5,000 daltons, trimethylolpropaneoxetane(TMPO), poly(ethylene oxide) (PEO) oligomer having a molecular weight (Mw) of less than 5,000 daltons, ethyl hexyl oxetane (2EH oxetane), difunctionaloxetane, trimethylolpropanetriacrylate (TM PTA) of the following formula (5), tripropyleneglycoldiacrylate(TPGDA) of the following formula (6), ethoxylatedbisphenol A diacrylate of the following formula (7) in which n+m=3, ethoxylatedtrimethylolpropanetriacrylate of the following formula (8), bisphenol A diglycidyl ether diacrylate of the following formula (9), 1,2-cyclic ethers, 1,3-cyclic ethers, 1,4-cyclic ethers, anhydrides, lactones, lactams, cyclic ethers, siloxanes, oxazolines, oxalidines, and bismaleimides;
8. The cure in place liquid of claim 1 wherein the structural diluent is selected from the group consisting of 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate (S-21), Bis[(3,4-epoxycyclohexyl)methyl]adipate (S-28), difunctionalbisphenol A/epichlorohydrin derived liquid epoxy resin (Epon 828), Bisphenol A epoxy resin having a weight per epoxide of 235-263 g/eq as measured by ASTM D1652 (Epon 834), beta-(3,4-epoxycyclohexyl)ethyltrimethoxysilane (A-186), gamma-glycidoxypropyltrimethoxysilane (A-187), glycidyl ester of neodecanoic acid (EP-10), isocyanate-functional urethane acrylate (Desmolux D100), isocyanate-bearing urethane acrylate (Desmolux D200), aliphatic polyisocyanate (low-viscosity hexamethylenediisocyanate (HDI) biuret) (Desmodur N3200), aliphatic polyisocyanate (hexamethylenediisocyanate (HDI) biuret) (Desmodur N100), aliphatic polyisocyanate (hexamethylenediisocyanate (HDI) trimer) (Desmodur N3300), poly(propylene oxide) (PPO) oligomer having a molecular weight (Mw) of less than 5,000 daltons, trimethylolpropaneoxetane (TMPO), poly(ethylene oxide) (PEO) oligomer having a molecular weight (Mw) of less than 5,000 daltons, ethyl hexyl oxetane (2EH oxetane), difunctionaloxetane, ethoxylatedbisphenol A diacrylate of the following formula (7) in which n+m=3, ethoxylatedtrimethylolpropanetriacrylate of the following formula (8), bisphenol A diglycidyl ether diacrylate of the following formula (9), 1,2-cyclic ethers, 1,3-cyclic ethers, 1,4-cyclic ethers, anhydrides, lactones, lactams, cyclic ethers, siloxanes, oxazolines, oxalidines, and bismaleimides;
9. The cure in place liquid of claim 1 wherein the structural diluent is selected from the group consisting of 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate (S-21), Bis[(3,4-epoxycyclohexyl)methyl]adipate (S-28), difunctionalbisphenol A/epichlorohydrin derived liquid epoxy resin (Epon 828), Bisphenol A epoxy resin having a weight per epoxide of 235-263 g/eq as measured by ASTM D1652 (Epon 834), beta-(3,4-epoxycyclohexyl)ethyltrimethoxysilane (A-186), gamma-glycidoxypropyltrimethoxysilane (A-187), glycidyl ester of neodecanoic acid (EP-10), isocyanate-functional urethane acrylate (Desmolux D100), isocyanate-bearing urethane acrylate (Desmolux D200), aliphatic polyisocyanate (low-viscosity hexamethylenediisocyanate (HDI) biuret) (Desmodur N3200), aliphatic polyisocyanate (hexamethylenediisocyanate (HDI) biuret) (Desmodur N100), aliphatic polyisocyanate (hexamethylenediisocyanate (HDI) trimer) (Desmodur N3300), poly(propylene oxide) (PPO) oligomer having a molecular weight (Mw) of less than 5,000 daltons, trimethylolpropaneoxetane (TMPO), poly(ethylene oxide) (PEO) oligomer having a molecular weight (Mw) of less than 5,000 daltons, ethyl hexyl oxetane (2EH oxetane), difunctionaloxetane, ethoxylatedbisphenol A diacrylate of the following formula (7) in which n+m=3, ethoxylatedtrimethylolpropanetriacrylate of the following formula (8), bisphenol A diglycidyl ether diacrylate of the following formula (9), 1,2-cyclic ethers, 1,3-cyclic ethers, 1,4-cyclic ethers, butyrolactone, valerolactone, caprolactone, methy-butyrolactone, butyrolactam, valerolactam, caprolactam, cyclic ethers, siloxanes, oxazolines, oxalidines, bismaleimides,
lactones of the following formulas (10)-(12)
wherein n is 4 or 5, h, i, k, and m are independently 1 or 2 and each R is independently chosen from H or hydrocarbyl containing up to 12 carbon atoms.
10. The cure in place liquid of claim 1 wherein the non-reactive segment is non-reactive with the reactive functional group of the reactive segments.
11. The cure in place liquid of claim 1 wherein the acrylic block base polymer has a Mw of 25,000 to 1,000,000.
12. A cure in place liquid consisting of:
5-50 wt % of a bodying component including a pre-polymerized acrylic block base polymer having a molecular weight (Mw) of 5,000 to 1,000,000, the acrylic block base polymer including two functional end segments and one non-reactive middle segment;
50-95 wt % of at least one structural diluent;
0.01-10 wt % of a curative; and
0-10 wt % stabilizer/process aid.
13. The cure in place liquid of claim 12 wherein the structural diluent is selected from the group consisting of 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate (S-21), Bis[(3,4-epoxycyclohexyl)methyl]adipate (S-28), difunctionalbisphenol A/epichlorohydrin derived liquid epoxy resin (Epon 828), Bisphenol A epoxy resin having a weight per epoxide of 235-263 g/eq as measured by ASTM D1652 (Epon 834), beta-(3,4-epoxycyclohexyl)ethyltrimethoxysilane (A-186), gamma-glycidoxypropyltrimethoxysilane (A-187), glycidyl ester of neodecanoic acid (EP-10), isocyanate-functional urethane acrylate (Desmolux D100), isocyanate-bearing urethane acrylate (Desmolux D200), aliphatic polyisocyanate (low-viscosity hexamethylenediisocyanate (HDI) biuret) (Desmodur N3200), aliphatic polyisocyanate hexamethylenediisocyanate (HDI) biuret) (Desmodur N100), aliphatic polyisocyanate hexamethylenediisocyanate (HDI) trimer) (Desmodur N3300), poly(propylene oxide) (PPO) oligomer having a molecular weight (Mw) of less than 5,000 daltons, trimethylolpropaneoxetane (TMPO), poly(ethylene oxide) (PEO) oligomer having a molecular weight (Mw) of less than 5,000 daltons, ethyl hexyl oxetane (2EH oxetane), difunctionaloxetane, trimethylolpropanetriacrylate (TMPTA) of the following formula (5), tripropyleneglycoldiacrylate(TPGDA) of the following formula (6), ethoxylatedbisphenol A diacrylate of the following formula (7) in which n+m=3, ethoxylatedtrimethylolpropanetriacrylate of the following formula (8), bisphenol A diglycidyl ether diacrylate of the following formula (9), 1,2-cyclic ethers, 1,3-cyclic ethers, 1,4-cyclic ethers, anhydrides, lactones, lactams, cyclic ethers, siloxanes, oxazolines, oxalidines, and bismaleimides;
14. The cure in place liquid of claim 12 wherein the structural diluent is selected from the group consisting of 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate (S-21), Bis[(3,4-epoxycyclohexyl)methyl]adipate (S-28), difunctionalbisphenol A/epichlorohydrin derived liquid epoxy resin (Epon 828), Bisphenol A epoxy resin having a weight per epoxide of 235-263 g/eq as measured by ASTM D1652 (Epon 834), beta-(3,4-epoxycyclohexyl)ethyltrimethoxysilane (A-186), gamma-glycidoxypropyltrimethoxysilane (A-187), glycidyl ester of neodecanoic acid (EP-10), isocyanate-functional urethane acrylate (Desmolux D100), isocyanate-bearing urethane acrylate (Desmolux D200), aliphatic polyisocyanate (low-viscosityhexamethylenediisocyanate (HDI) biuret) (Desmodur N3200), aliphatic polyisocyanate(hexamethylenediisocyanate (HDI) biuret) (Desmodur N100), aliphatic polyisocyanate(hexamethylenediisocyanate (HDI) trimer) (Desmodur N3300), poly(propylene oxide) (PPO) oligomer having a molecular weight (Mw) of less than 5,000 daltons, trimethylolpropaneoxetane (TMPO), poly(ethylene oxide) (PEO) oligomer having a molecular weight (Mw) of less than 5,000 daltons, ethyl hexyl oxetane (2EH oxetane), difunctionaloxetane, ethoxylatedbisphenol A diacrylate of the following formula (7) in which n+m=3, ethoxylatedtrimethylolpropanetriacrylate of the following formula (8), bisphenol A diglycidyl ether diacrylate of the following formula (9), 1,2-cyclic ethers, 1,3-cyclic ethers, 1,4-cyclic ethers, butyrolactone, valerolactone, caprolactone, methy-butyrolactone, butyrolactam, valerolactam, caprolactam, cyclic ethers, siloxanes, oxazolines, oxalidines, bismaleimides,
lactones of the following formulas (10)-(12)
wherein n is 4 or 5, h, i, k, and m are independently 1 or 2 and each R is independently chosen from H or hydrocarbyl containing up to 12 carbon atoms.
15. A cure in place liquid comprising:
5-50 wt % of a bodying component including a pre-polymerized acrylic block base polymer having a molecular weight (Mw) of 5,000 to 1,000,000, the acrylic block base polymer including two functional end segments and one non-reactive middle segment;
50-95 wt % of at least one structural diluent;
0.01-10 wt % of a curative; and
0-10 wt % stabilizer/process aid.