Peelable adhesive polymeric film

• US 10,442,959 B2
• Filed: 04/29/2016
• Issued: 10/15/2019
• Est. Priority Date: 05/01/2015
• Status: Active Grant

• Current Assignee: DuPont Performance Elastomers L (Bristol-Myers Squibb Company)
• Original Assignee: DuPont Performance Elastomers L (Bristol-Myers Squibb Company)
• Inventors: Robinson, Julian N., Symonds, Jackie H., Mackerron, Duncan, Sankey, Stephen W., Evans, Jamie, Little, Rachel Clare
• Primary Examiner(s): Lee, Daniel H
• Application Number:
  US15/570,766
• Publication Number:
  US 20180118980A1
• Time in Patent Office: 1,264 Days
• CPC Class Codes: B32B 17/10779 containing polyester
• CPC Class Codes: B32B 2255/10 on synthetic resin layer or on natural or synthetic rubber layer
• CPC Class Codes: B32B 2255/26 Polymeric coating
• CPC Class Codes: B32B 2264/102 Oxide or hydroxide
• CPC Class Codes: B32B 2264/104 Oxysalt, e.g. carbonate, sulfate, phosphate or nitrate particles
• CPC Class Codes: B32B 2307/41 Opaque
• CPC Class Codes: B32B 2307/518 bi-axially
• CPC Class Codes: B32B 2307/536 Hardness
• CPC Class Codes: B32B 2307/732 Dimensional properties
• CPC Class Codes: B32B 2307/746 Slipping, anti-blocking, low friction
• CPC Class Codes: B32B 2309/02 Temperature
• CPC Class Codes: B32B 2309/04 Time
• CPC Class Codes: B32B 2457/14 Semiconductor wafers
• CPC Class Codes: B32B 2457/20 Displays, e.g. liquid crystal displays, plasma displays
• CPC Class Codes: B32B 27/08 of synthetic resin
• CPC Class Codes: B32B 27/20 using fillers, pigments, thixotroping agents
• CPC Class Codes: B32B 27/36 comprising polyesters
• CPC Class Codes: B32B 37/025 Transfer laminating
• CPC Class Codes: B32B 43/006 Delaminating
• CPC Class Codes: B32B 7/12 using interposed adhesives or interposed materials with bonding properties
• CPC Class Codes: B32B 9/005 : comprising one layer of ceramic material, e.g. porcelain, ceramic tile layered products with at least two ceramic layers composed mainly of ceramic B32B18/00
• CPC Class Codes: B32B 9/045 : of synthetic resin
• CPC Class Codes: C08G 18/0819 : containing anionic or anionogenic groups
• CPC Class Codes: C08G 2170/80 : Compositions for aqueous adhesives
• CPC Class Codes: C09J 129/04 : Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids
• CPC Class Codes: C09J 133/06 : of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
• CPC Class Codes: C09J 175/04 : Polyurethanes
• CPC Class Codes: C09J 175/06 : from polyesters
• CPC Class Codes: C09J 175/14 : Polyurethanes having carbon-to-carbon unsaturated bonds
• CPC Class Codes: C09J 175/16 : having terminal carbon-to-carbon unsaturated bonds
• CPC Class Codes: C09J 2203/326 : for bonding electronic components such as wafers, chips or semiconductors
• CPC Class Codes: C09J 2429/00 : Presence of polyvinyl alcohol
• CPC Class Codes: C09J 2433/00 : Presence of (meth)acrylic polymer
• CPC Class Codes: C09J 2475/00 : Presence of polyurethane
• CPC Class Codes: C09J 4/06 : Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
• CPC Class Codes: C09J 7/255 : Polyesters
• CPC Class Codes: H01L 21/6835 : using temporarily an auxiliary support
• CPC Class Codes: H01L 2221/68386 : Separation by peeling
• CPC Class Codes: H10K 71/80 : using temporary substrates
• CPC Class Codes: H10K 77/111 : Flexible substrates

Abstract

Peelable polymeric film, in particular, peelable polymeric film which comprises a polymeric substrate layer and a coating layer of adhesive, and which is of particular use in the manufacture of electronic devices is described. The adhesive layer is derived from an aqueous composition which comprises an aliphatic polyurethane and is switchable.

Claims

1. A method for manufacturing an electronic device comprising:

(a) heating a laminate comprising (i) a polyester film substrate having a first surface and a second surface, (ii) an adhesive coating derived from an aqueous composition comprising an aliphatic polyurethane and (iii) a glass or silicon wafer substrate, wherein the adhesive coating is disposed between the polyester film substrate and the glass or silicon wafer substrate, to a temperature of at least 150°

C. for a period of at least two minutes; and

(b) peeling the polyester film substrate from the glass or silicon wafer substrate to leave the adhesive coating on the glass or silicon wafer substrate.

2. The method according to claim 1 comprising the steps of:

(c) providing a polyester film comprising (i) a polyester film substrate having a first surface and a second surface and (ii) an adhesive coating derived from an aqueous composition comprising an aliphatic polyurethane wherein said adhesive coating is disposed on a first surface of said polyester film substrate;

(d) laminating a glass or silicon wafer substrate to the first surface of the polyester film substrate such that the adhesive coating is disposed between the polyester film substrate and the glass or silicon wafer substrate;

(e) processing the laminate by subjecting it to a temperature of at least 150°

C. for a period of at least 2 minutes and disposing one or more electronic components on the second surface of the polyester film substrate; and

(f) peeling the polyester film substrate from the glass or silicon wafer substrate to leave the adhesive coating on the glass or silicon wafer substrate.

3. The method according to claim 1, wherein following the step of peeling the polyester film substrate from the glass or silicon wafer substrate, the first surface of the polyester film substrate is free from adhesive coating.

4. The method according to claim 1, wherein the electronic device is an electronic display device, or is a photovoltaic cell or a semiconductor device.

5. The method of claim 1, wherein said temperature is no more than 200°

C.

6. The method according to claim 1, wherein following the step of peeling the polyester film substrate from the glass or silicon wafer substrate, the polyester film substrate is used as a substrate in said electronic device.

7. The method according to claim 1, wherein the change in the glass transition temperature (at onset) of the aqueous coating after drying and heating to 150°

C. for two minutes, is no more than about 15°

C., as measured by modulated differential scanning calorimetry (DSC).

8. The method according to claim 1, wherein the adhesive coating exhibits a CO₂ peak relative intensity of less than 0.2, wherein CO₂ peak relative intensity is defined as the intensity of the CO₂ asymmetric stretching absorption in the region of 2200 to 2400 cm⁻

1 of the infrared spectrum as measured by FTIR-TGA analysis at 18 minutes during a temperature cycle which consists of heating the adhesive coating at 10°

C./min from 40°

C. to an isothermal hold at 200°

C. for 5 minutes, relative to the intensity of the same CO₂ asymmetric stretching absorption of atmospheric air in the same temperature cycle, and/or wherein the adhesive coating evolves no more than 31 μ

g of CO₂ per 25 mg of the adhesive coating as measured by FTIR-TGA analysis of the CO₂ asymmetric stretching absorption in the infrared spectrum at 18 minutes during a temperature cycle which consists of heating the adhesive coating at 10°

C./min from 40°

C. to an isothermal hold at 180°

C. for 5 minutes.

9. The method according to claim 1, wherein the aqueous composition further comprises acrylic monomers, wherein the acrylic monomers are selected from the group consisting of methyl methacrylate, ethyl acrylate, isopropyl acrylate, butyl acrylate, butyl methacrylate, pentaerythritol acrylate type materials and hydroxyethyl methacrylate (HEMA).

10. The method according to claim 9, wherein the aqueous composition is a Type 1 urethane-acrylic hybrid polymer dispersion.

11. The method according to claim 9, wherein the aqueous composition is a Type 2 urethane-acrylic hybrid polymer dispersion.

12. The method according to claim 1, wherein the aliphatic polyurethane is derived from an aliphatic diisocyanate and a polyester polyol, and wherein the aliphatic diisocyanate is selected from the group consisting of 1,6-diisocyanatohexane (HDI), 1,4-diisocyanatobutane, 1-isocyanato-5-isocyanato-methyl-3,3,5-trimethyl-cyclohexane or isophorone diisocyanate (PIDI), bis(4-isocyanatocyclohexyl)methane, cyclohexane diisocyanate (CHDI), 2,2,4-trimethylhexamethylene diisocyanate (TMDI), 1,3-bis(isocyanatomethyl)cyclohexane (H₆XDI), 1,1′

methylenebis(4-isocyanato)-cyclohexane (H₁₂MDI) and mixtures thereof and/or the polyester polyol is selected from the group consisting of polycaprolactone diols, polycarbonate diols and mixtures thereof.

13. The method according to claim 1, wherein the aqueous composition further comprises a diluent, wherein the diluent is selected from the group consisting of N-ethyl pyrrolidone (NEP), and butyl diglycol.

14. The method according to claim 1, wherein the adhesive coating has a total nitrogen content in the range from about 2 to about 6 mol%.

15. The method according to claim 1, wherein the ratio of nitrogen to carbon in the adhesive coating is in the range from 0.01 to about 0.05.

16. The method according to claim 1, wherein the aqueous composition from which the adhesive coating is derived comprises aliphatic polyurethane, poly(butylmethacrylate), polycaprolactone and poly(hexamethylene carbonate).

17. The method according to claim 16, wherein the aliphatic polyurethane is present in an amount of about 5 to 15 mol%, the poly(butylmethacrylate) is present in an amount of about 40 to 80 mol%, the polycaprolactone is present in an amount of about 7 to 19 mol%, and the poly-(hexamethylene carbonate) is present at amount of about 5 to 15 mol%, based on the total content of carbonyl group-containing species present in the composition.

18. A laminate comprising (i) a polyester film substrate having a first surface and a second surface, (ii) an adhesive coating derived from an aqueous composition comprising an aliphatic polyurethane, and (iii) a glass or silicon wafer substrate, wherein the adhesive coating is disposed between the polyester film substrate and the glass or silicon wafer substrate, wherein there is a change in the plane of failure of the adhesive coating after heating to a temperature of at least 150°

C.

19. The laminate according to claim 18, wherein the adhesion between the polyester film substrate and the adhesive coating is greater than the adhesion between the adhesive coating and the glass or silicon wafer substrate and wherein, following the change in the plane of failure of the adhesive coating, the adhesion between the glass or silicon wafer and the adhesive coating is greater than the adhesion between the adhesive coating and the polyester film substrate.

20. The laminate according to claim 18, wherein the change in the glass transition temperature (at onset) of the aqueous coating after drying and heating to 150°

C. for two minutes, is no more than about 15°

C. as measured by modulated differential scanning calorimetry (DSC).

21. The laminate according to claim 18, wherein the adhesive coating exhibits a CO₂ peak relative intensity of less than 0.2, wherein CO₂ peak relative intensity is defined as the intensity of the CO₂ asymmetric stretching absorption in the region of 2200 to 2400 cm⁻

1 of the infrared spectrum as measured by FTIR-TGA analysis at 18 minutes during a temperature cycle which consists of heating the adhesive coating at 10°

C./min from 40°

C. to an isothermal hold at 200°

C. for 5 minutes, relative to the intensity of the same CO₂ asymmetric stretching absorption of atmospheric air in the same temperature cycle, and/or wherein the adhesive coating evolves no more than 31 μ

g of CO₂ per 25 mg of the adhesive coating as measured by FTIR-TGA analysis of the CO₂ asymmetric stretching absorption in the infrared spectrum at 18 minutes during a temperature cycle which consists of heating the adhesive coating at 10°

C./min from 40°

C. to an isothermal hold at 180°

C. for 5 minutes.

22. The laminate according to claim 18 wherein the aqueous composition further comprises acrylic monomers, wherein the acrylic monomers are selected from the group consisting of methyl methacrylate, ethyl acrylate, isopropyl acrylate, butyl acrylate, butyl methacrylate, pentaerythritol acrylate type materials and hydroxyethyl methacrylate (HEMA).

23. The laminate according to claim 22, wherein the aqueous composition is a Type 1 urethane-acrylic hybrid polymer dispersion.

24. The laminate according to claim 22, wherein the aqueous composition is a Type 2 urethane-acrylic hybrid polymer dispersion.

25. The laminate according to claim 18, wherein the aliphatic polyurethane is derived from an aliphatic diisocyanate and a polyester polyol, and wherein the aliphatic diisocyanate is selected from the group consisting of 1,6-diisocyanatohexane (HDI), 1,4-diisocyanatobutane, 1-isocyanato-5-isocyanato-methyl-3,3,5-trimethyl-cyclohexane or isophorone diisocyanate (PIDI), bis(4-isocyanatocyclohexyl)methane, cyclohexane diisocyanate (CHDI), 2,2,4-trimethylhexamethylene diisocyanate (TMDI), 1,3-bis(isocyanatomethyl)cyclohexane (H₆XDI), 1,1′

methylenebis(4-isocyanato)-cyclohexane (H₁₂MDI) and mixtures thereof and/or the polyester polyol is selected from the group consisting of polycaprolactone diols, polycarbonate diols and mixtures thereof.

26. The laminate according to claim 18, wherein the aqueous composition further comprises a diluent, wherein the diluent is selected from the group consisting of N-ethyl pyrrolidone (NEP) and butyl diglycol.

27. The laminate according to claim 18, wherein the adhesive coating has a total nitrogen content in the range from about 2 to about 6 mol% %.

28. The laminate according to claim 18, wherein the ratio of nitrogen to carbon in the adhesive coating is in the range from 0.01 to about 0.05.

29. The laminate according to claim 18, wherein the aqueous composition from which the adhesive coating is derived comprises aliphatic polyurethane, poly(butylmethacrylate), polycaprolactone and poly(hexamethylene carbonate).

30. The laminate according to claim 29, wherein the aliphatic polyurethane is present in an amount of about 5 to 15 mol%, the poly(butylmethacrylate) is present in an amount of about 40 to 80 mol%, preferably about 68 mol%, the polycaprolactone is present in an amount of about 7 to 19 mol%, and the poly(hexamethylene carbonate) is present at amount of about 5 to 15 mol%, based on the total content of carbonyl group-containing species present in the composition.

31. A polyester film comprising a polyester film substrate and an adhesive coating, wherein the adhesive coating is derived from an aqueous composition comprising an aliphatic polyurethane and wherein the change in the glass transition temperature at onset (Δ

Tg (onset)) of the adhesive coating after heating to 150°

C. for two minutes, is no more than about 15°

C. as measured by modulated differential scanning calorimetry (DSC).

32. The film according to claim 31, wherein the adhesive coating exhibits a CO₂ peak relative intensity of less than 0.2 wherein CO₂ peak relative intensity is defined as the intensity of the CO₂ asymmetric stretching absorption in the region of 2200 to 2400 cm⁻

1 of the infrared spectrum as measured by FTIR-TGA analysis at 18 minutes during a temperature cycle which consists of heating the adhesive coating at 10°

C./min from 40°

C. to an isothermal hold at 200°

C. for 5 minutes, relative to the intensity of the same CO₂ asymmetric stretching absorption of atmospheric air in the same temperature cycle, and/or wherein the adhesive coating evolves no more than 31 μ

g of CO₂ per 25 mg of the adhesive coating as measured by FTIR-TGA analysis of the CO₂ asymmetric stretching absorption in the infrared spectrum at 18 minutes during a temperature cycle which consists of heating the adhesive coating at 10°

C./min from 40°

C. to an isothermal hold at 180°

C. for 5 minutes.

33. The film according to claim 31, wherein the aqueous composition further comprises acrylic monomers, wherein the acrylic monomers are selected from the group consisting of methyl methacrylate, ethyl acrylate, isopropyl acrylate, butyl acrylate, butyl methacrylate, pentaerythritol acrylate type materials and hydroxyethyl methacrylate (HEMA).

34. The film according to claim 33, wherein the aqueous composition is a Type 1 urethane-acrylic hybrid polymer dispersion.

35. The film according to claim 33, wherein the aqueous composition is a Type 2 urethane-acrylic hybrid polymer dispersion.

36. The film according to claim 31, wherein the aliphatic polyurethane is derived from an aliphatic diisocyanate and a polyester polyol, and wherein the aliphatic diisocyanate is selected from the group consisting of 1,6-diisocyanatohexane (HDI), 1,4-diisocyanatobutane, 1-isocyanato-5-isocyanato-methyl-3,3,5-trimethyl-cyclohexane or isophorone diisocyanate (PIDI), bis(4-isocyanatocyclohexyl)methane, cyclohexane diisocyanate (CHDI), 2,2,4-trimethylhexamethylene diisocyanate (TMDI), 1,3-bis(isocyanatomethyl)cyclohexane (H₆XDI), 1,1′

methylenebis(4-isocyanato)-cyclohexane (H₁₂MDI) and mixtures thereof and/or the polyester polyol is selected from the group consisting of polycaprolactone diols, polycarbonate diols and mixtures thereof.

37. The film according to claim 31, wherein the aqueous composition further comprises a diluent, wherein the diluent is selected from the group consisting of M-ethyl pyrrolidone (NEP) and butyl diglycol.

38. The film according to claim 31, wherein the adhesive coating has a total nitrogen content in the range from about 2 to about 6 mol%.

39. The film according to claim 31, wherein the ratio of nitrogen to carbon in the adhesive coating is in the range from 0.01 to about 0.05.

40. The film according to claim 31, wherein the aqueous composition from which the adhesive coating is derived comprises aliphatic polyurethane, poly(butylmethacrylate), polycaprolactone and poly(hexamethylene carbonate).

41. The film according to claim 40, wherein the aliphatic polyurethane is present in an amount of about 5 to 15 mol%, the poly(butylmethacrylate) is present in an amount of about 40 to 80 mol%, the polycaprolactone is present in an amount of about 7 to 19 mol%, and the poly(hexamethylene carbonate) is present at amount of about 5 to 15 mol%, based on the total content of carbonyl group-containing species present in the composition.

42. A polyester film comprising a polyester film substrate and an adhesive coating, wherein the adhesive coating is derived from an aqueous composition comprising an aliphatic polyurethane and wherein the adhesive coating exhibits a CO₂ peak relative intensity of less than 0.2, wherein CO₂ peak relative intensity is defined as the intensity of the CO₂ asymmetric stretching absorption in the region of 2200 to 2400 cm⁻

1 of the infrared spectrum as measured by FTIR-TGA analysis at 18 minutes during a temperature cycle which consists of heating the adhesive coating at 10°

C./min from 40°

C. to an isothermal hold at 200°

C. for 5 minutes, relative to the intensity of the same CO₂ asymmetric stretching absorption of atmospheric air in the same temperature cycle, and/or wherein the adhesive coating evolves no more than 31 μ

g of CO₂ per 25 mg of the adhesive coating as measured by FTIR-TGA analysis of the CO₂ asymmetric stretching absorption in the infrared spectrum at 18 minutes during a temperature cycle which consists of heating the adhesive coating at 10°

C./min from 40°

C. to an isothermal hold at 180°

C. for 5 minutes.

43. The film according to claim 42, wherein the aqueous composition further comprises acrylic monomers, wherein the acrylic monomers are selected from the group consisting of methyl methacrylate, ethyl acrylate, isopropyl acrylate, butyl acrylate, butyl methacrylate, pentaerythritol acrylate type materials and hydroxyethyl methacrylate (HEMA).

44. The film according to claim 43, wherein the aqueous composition is a Type 1 urethane-acrylic hybrid polymer dispersion.

45. The film according to claim 44, wherein the aqueous composition is a Type 2 urethane-acrylic hybrid polymer dispersion.

46. The film according to claim 42, wherein the aliphatic polyurethane is derived from an aliphatic diisocyanate and a polyester polyol, and wherein the aliphatic diisocyanate is selected from the group consisting of 1,6-diisocyanatohexane (HDI), 1,4-diisocyanatobutane, 1-isocyanato-5-isocyanato-methyl-3,3,5-trimethyl-cyclohexane or isophorone diisocyanate bis(4-isocyanatocyclohexyl)methane, cyclohexane diisocyanate (CHDI), 2,2,4-trimethylhexamethylene diisocyanate (TMDI), 1,3-bis(isocyanatomethyl)cyclohexane (H₆XDI), 1,1′

methylenebis(4-isocyanato)-cyclohexane (H₁₂MDI) and mixtures thereof and/or the polyester polyol is selected from the group consisting of polycaprolactone diols, polycarbonate diols and mixtures thereof.

47. The film according to claim 42, wherein the aqueous composition further comprises a diluent, preferably wherein the diluent is selected from the group consisting of N-ethyl pyrrolidone (NEP) and butyl diglycol.

48. The film according to claim 42, wherein the adhesive coating has a total nitrogen content in the range from about 2 to about 6 mol%.

49. The film according to claim 42, wherein the ratio of nitrogen to carbon in the adhesive coating is in the range from 0.01 to about 0.05.

50. The film according to claim 42, wherein the aqueous composition from which the adhesive coating is derived comprises aliphatic polyurethane, poly(butylmethacrylate), polycaprolactone and poly(hexamethylene carbonate).

51. The film according to claim 50, wherein the aliphatic polyurethane is present in an amount of about 5 to 15 mol%, the poly(butylmethacrylate) is present in an amount of about 40 to 80 mol%, the polycaprolactone is present in an amount of about 7 to 19 mol%, and the poly(hexamethylene carbonate) is present at amount of about 5 to 15 mol%, based on the total content of carbonyl group-containing species present in the composition.