WO2008070030A1 - Uv curable composition - Google Patents
Uv curable composition Download PDFInfo
- Publication number
- WO2008070030A1 WO2008070030A1 PCT/US2007/024752 US2007024752W WO2008070030A1 WO 2008070030 A1 WO2008070030 A1 WO 2008070030A1 US 2007024752 W US2007024752 W US 2007024752W WO 2008070030 A1 WO2008070030 A1 WO 2008070030A1
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- WO
- WIPO (PCT)
- Prior art keywords
- acrylate
- composition
- sec
- benzophenone
- radiation
- Prior art date
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L15/00—Compositions of rubber derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L19/00—Compositions of rubbers not provided for in groups C08L7/00 - C08L17/00
- C08L19/006—Rubber characterised by functional groups, e.g. telechelic diene polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/08—Homopolymers or copolymers of acrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
Definitions
- the present invention provides a UV curable composition
- a UV curable composition comprising an acrylate component, comprising an acrylate-functionalized hydrogenated polybutadiene, and at least one mono-functional acrylate, and a photoinitiator combination triggered upon exposure to radiation at 365 nm of the electromagnetic spectrum comprising a bisacyl phosphine oxide and benzophenone, where when dispensed at a thickness of about 1 mm and exposed to UV radiation generated at a wavelength of 365 nm the composition cures through the thickness of the dispensed composition at a speed between 40 mm/sec to 100 mm/sec.
- Photocurable compositions are well known. Some may be based on acrylate functional groups, while others are based on vinyl ether or epoxy functional groups. These known photocurable compositions may include materials having oligomeric backbones, where the oligomer is a silicone based material, an acrylate base material, or a urethane base material.
- the material once cured desirably minimizes the ingress of environmental contaminants to that electronic circuitry. Should that not be the case, the environmental contaminants could cause corrosion in the circuitry, leading to electrical disconnect and failure of the electronic component. This clearly is highly undesirable.
- European Patent Publication No. EP 1 376 561 speaks to an adhesive composition targeted towards medical and electronics fields.
- the composition contains a urethane acrylate and an acrylamide, together with a photoinitiator component containing at least one acyl phosphine oxide and at least one additional photoinitiator, such as a benzophenone.
- benzophenone is not a photoinitiator in the inventive composition, and does not itself produce radicals required to initiate polymerization upon exposure to UV light of a 365 nm wavelength, but rather requires an additional electron donor to do so.
- the present invention provides a UV curable composition
- a UV curable composition comprising an acrylate component, comprising an acrylate-functionalized hydrogenated polybutadiene, and at least one mono-functional acrylate, and a photoinitiator combination triggered upon exposure to radiation at 365 nm of the electromagnetic spectrum comprising a bisacyl phosphine oxide and benzophenone, where when dispensed at a thickness of about 1 mm and exposed to UV radiation generated at a wavelength of 365 nm the composition cures through the thickness of the dispensed composition at a speed between 40 mm/sec to 100 mm/sec.
- the present invention provides a UV curable composition
- a UV curable composition comprising an acrylate component, comprising an acrylate-functionalized hydrogenated polybutadiene, and at least one mono-functional acrylate, and a photoinitiator combination triggered upon exposure to radiation at 365 nm of the electromagnetic spectrum comprising a bisacyl phosphine oxide and benzophenone.
- the bisacyl phosphine oxide should be present in an amount between about 1.5 and about 4 weight percent and the benzophenone present in an amount between about 0.01 and about 1 weight percent. With these percentage ranges, when dispensed at a thickness of about 1 mm and exposed to UV radiation generated at a wavelength of 365 nm the composition cures through the thickness of the dispensed composition at a speed between 40 mm/sec to 100 mm/sec. [0011] More specifically, when the amount of benzophenone relative to bisacyl phosphine oxide is in the range of 0.005 to 0.25, a cure speed of 40 mm/sec may be achieved.
- the UV radiation used to cure the inventive composition may be generated from a variety of UV light sources capable of generating 365 nm radiation. However, a particularly desirable source to generated UV radiation at that wavelength is a LED source.
- the UV radiation intensity generated by the source is between about 120 to about 130 mW/cm 2 .
- Cure speed is dependant on the LED power (intensity of UV radiation) and thus higher power would allow for faster cure speeds, all else being equal.
- the inventive composition as noted has an acrylate-functionalized hydrogenated polybutadiene as a portion of the acrylate component. This polybutadiene has a molecular weight of about 3,000, as reported by the manufacturer Sartomer, Inc., Exton, PA. This polybutadiene happens to have hydrophobicity due to the backbone, which lends itself to be a particularly useful in commercial applications where the ingress of moisture through the cured composition can foul that which is beneath the composition. For instance, microelectronic circuitry can be harmed if moisture penetrates the cured composition, thereby creating short circuits and a malfunction of the device.
- the mono-functional acrylate which is also part of the composition may be chosen from a host of acrylates, such as 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2-hydroxyethyl acrylate, pentaerythritol triacrylate, 4- hydroxybutyl acrylate, isobornyl acrylate, cyclohexyl acrylate, tetrahydrofurfuryl acrylate, t-butylaminoethyl acrylate, cyanoethylacrylate, chloroethyl (meth) acrylate and lauryl acrylate.
- the corresponding (meth) acrylates are also embraced by the mono-functional acrylate.
- the present invention also provides a method of curing at 365 nm using an LED a UV curable composition at cure speeds within the range of about 40 mm/sec to about 100 mm/sec.
- This method includes the steps of: a. dispensing onto a substrate a UV curable composition comprising a photoinitiator combination triggered upon exposure to radiation at 365 nm of the electromagnetic spectrum comprising a bisacyl phosphine oxide and benzophenone, where the bisacyl phosphine oxide is present in an amount between about 1.5 and about 4 weight percent and the benzophenone is present in an amount between about 0.01 and about 1 weight percent; and b. exposing the UV curable composition to UV radiation at a wavelength of 365 nm using an LED, such that the UV curable composition cures at cure speeds within the range of about 40 mm/sec to about 100 mm/sec.
- CN9014 is reported by the manufacturer, Sartomer Inc., to be a hydrophobic urethane acrylate oligomer having a hydrogenated polybutadiene backbone. CN9014 is reported to offer good chemical resistance and electrical properties.
- Cure through volume is determined by a visual inspection of when no liquid is observed beneath the surface of the cured composition, again after exposure to UV radiation at a wavelength of 365 nm and intensity of 120 to about 130 mW/cm 2 generated by a LED.
- Table 2A
Abstract
The present invention provides a UV curable composition comprising an acrylate component, comprising an acrylate-functionalized hydrogenated polybutadiene, and at least one mono-functional acrylate, and a photoinitiator combination triggered upon exposure to radiation at 365 nm of the electromagnetic spectrum comprising a bisacyl phosphine oxide and benzophenone, where when dispensed at a thickness of about 1mm and exposed to UV radiation generated at a wavelength of 365 nm the composition cures through the thickness of the dispensed composition at a speed between 40 mm/sec to 100 mm/sec.
Description
UV CURABLE COMPOSITION
BACKGROUND OF THE INVENTION Field of the Invention
[0001] The present invention provides a UV curable composition comprising an acrylate component, comprising an acrylate-functionalized hydrogenated polybutadiene, and at least one mono-functional acrylate, and a photoinitiator combination triggered upon exposure to radiation at 365 nm of the electromagnetic spectrum comprising a bisacyl phosphine oxide and benzophenone, where when dispensed at a thickness of about 1 mm and exposed to UV radiation generated at a wavelength of 365 nm the composition cures through the thickness of the dispensed composition at a speed between 40 mm/sec to 100 mm/sec.
Brief Description of Related Technology
[0002] Photocurable compositions are well known. Some may be based on acrylate functional groups, while others are based on vinyl ether or epoxy functional groups. These known photocurable compositions may include materials having oligomeric backbones, where the oligomer is a silicone based material, an acrylate base material, or a urethane base material.
[0003] In applications where microelectronic circuitry is to be coded with a curable composition, the material once cured desirably minimizes the ingress of environmental contaminants to that electronic circuitry. Should that not
be the case, the environmental contaminants could cause corrosion in the circuitry, leading to electrical disconnect and failure of the electronic component. This clearly is highly undesirable.
[0004] While combinations of triphenyl phosphine oxide or bisacyl phosphine oxide with benzophenone have been described, benzophenone is used in these instances as a second photoinitiator . For instance, in International Patent Publication No. WO 02/22697 a methacrylate casting resin is described, in which among other things 0.1 - 10 % phosphine oxide photoinitiator plus 0 to 10% of another photoinitiator, such as a benzophenone.
[0005] In addition, European Patent Publication No. EP 1 376 561 speaks to an adhesive composition targeted towards medical and electronics fields. The composition contains a urethane acrylate and an acrylamide, together with a photoinitiator component containing at least one acyl phosphine oxide and at least one additional photoinitiator, such as a benzophenone.
[0006] Notwithstanding the state of the art, as shown in the Examples, benzophenone is not a photoinitiator in the inventive composition, and does not itself produce radicals required to initiate polymerization upon exposure to UV light of a 365 nm wavelength, but rather requires an additional electron donor to do so. [0007] Thus, it would be desirable to provide a photocurable composition having robust properties against the ingress of environmental contaminants, while curing at a fast cure profile.
SUMMARY OF THE INVENTION
[0008] The present invention provides a UV curable composition comprising an acrylate component, comprising an acrylate-functionalized hydrogenated polybutadiene, and at least one mono-functional acrylate, and a photoinitiator combination triggered upon exposure to radiation at 365 nm of the electromagnetic spectrum comprising a bisacyl phosphine oxide and benzophenone, where when dispensed at a thickness of about 1 mm and exposed to UV radiation generated at a wavelength of 365 nm the composition cures through the thickness of the dispensed composition at a speed between 40 mm/sec to 100 mm/sec.
DETAILED DESCRIPTION OF THE INVENTION
[0009] The present invention provides a UV curable composition comprising an acrylate component, comprising an acrylate-functionalized hydrogenated polybutadiene, and at least one mono-functional acrylate, and a photoinitiator combination triggered upon exposure to radiation at 365 nm of the electromagnetic spectrum comprising a bisacyl phosphine oxide and benzophenone.
[0010] The bisacyl phosphine oxide should be present in an amount between about 1.5 and about 4 weight percent and the benzophenone present in an amount between about 0.01 and about 1 weight percent. With these percentage ranges, when dispensed at a thickness of about 1 mm and exposed to UV radiation generated at a wavelength of 365 nm the composition cures through the thickness of the dispensed composition at a speed between 40 mm/sec to 100 mm/sec. [0011] More specifically, when the amount of benzophenone relative to bisacyl phosphine oxide is in the
range of 0.005 to 0.25, a cure speed of 40 mm/sec may be achieved.
[0012] And, when the amount of benzophenone relative to bisacyl phosphine oxide is in the range of 0.025 to 0.5, a cure speed of 100 mm/sec may be achieved. [0013] The UV radiation used to cure the inventive composition may be generated from a variety of UV light sources capable of generating 365 nm radiation. However, a particularly desirable source to generated UV radiation at that wavelength is a LED source.
[0014] The UV radiation intensity generated by the source is between about 120 to about 130 mW/cm2. [0015] Cure speed is dependant on the LED power (intensity of UV radiation) and thus higher power would allow for faster cure speeds, all else being equal. [0016] The inventive composition as noted has an acrylate-functionalized hydrogenated polybutadiene as a portion of the acrylate component. This polybutadiene has a molecular weight of about 3,000, as reported by the manufacturer Sartomer, Inc., Exton, PA. This polybutadiene happens to have hydrophobicity due to the backbone, which lends itself to be a particularly useful in commercial applications where the ingress of moisture through the cured composition can foul that which is beneath the composition. For instance, microelectronic circuitry can be harmed if moisture penetrates the cured composition, thereby creating short circuits and a malfunction of the device.
[0017] The mono-functional acrylate which is also part of the composition may be chosen from a host of acrylates, such as 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2-hydroxyethyl acrylate, pentaerythritol triacrylate, 4-
hydroxybutyl acrylate, isobornyl acrylate, cyclohexyl acrylate, tetrahydrofurfuryl acrylate, t-butylaminoethyl acrylate, cyanoethylacrylate, chloroethyl (meth) acrylate and lauryl acrylate. The corresponding (meth) acrylates are also embraced by the mono-functional acrylate. [0018] The present invention also provides a method of curing at 365 nm using an LED a UV curable composition at cure speeds within the range of about 40 mm/sec to about 100 mm/sec. This method includes the steps of: a. dispensing onto a substrate a UV curable composition comprising a photoinitiator combination triggered upon exposure to radiation at 365 nm of the electromagnetic spectrum comprising a bisacyl phosphine oxide and benzophenone, where the bisacyl phosphine oxide is present in an amount between about 1.5 and about 4 weight percent and the benzophenone is present in an amount between about 0.01 and about 1 weight percent; and b. exposing the UV curable composition to UV radiation at a wavelength of 365 nm using an LED, such that the UV curable composition cures at cure speeds within the range of about 40 mm/sec to about 100 mm/sec.
EXAMPLES
[0019] In the table below, various samples were prepared to evaluate the performance in terms of surface cure, cure through depth and cure speed.
Table IA
Components Sample
A B C D E F G H
CN9014* 60.1 60.1 60 1 601 60 1 60. 1 60.1 60. 1
IBOA 25.59 22.59 22 1 21.6 24 1 23. 6 25.1 24. 6
Lauryl Acrylate 12.3 12.3 12 3 12.3 12. 3 12. 3 12.3 12. 3
IRGACURE 819 2 5 5 5 3 3 2 2
Benzophenone 0.01 0.01 0. 5 1 0. 5 1 0.5 1
* CN9014 is reported by the manufacturer, Sartomer Inc., to be a hydrophobic urethane acrylate oligomer having a hydrogenated polybutadiene backbone. CN9014 is reported to offer good chemical resistance and electrical properties.
Table IB
[0020] In the table below, the performance of these samples is reported. Surface cure is determined by a visual inspection when the surface is dry to the touch, after exposure to UV radiation at a wavelength of 365 nm and intensity of 120 to about 130 mW/cm2 generated by a LED
(commercially available from Panasonic as Aicure LED SPOT TYPE, model ANUJ5014) . Cure through volume is determined by a visual inspection of when no liquid is observed beneath the surface of the cured composition, again after exposure to UV radiation at a wavelength of 365 nm and intensity of 120 to about 130 mW/cm2 generated by a LED.
Table 2A
Table 2B
[0021] In Tables 2A and 2B, Ok indicates a cure through the depth of the dispensed composition; ICTD indicates the observation of liquid beneath a surface cure and thus incomplete cure through depth; and ISC indicates the observation of incomplete surface cure.
Claims
1. A UV curable composition comprising: An acrylate component, comprising an acrylate-functionalized hydrogenated polybutadiene, and at least one mono-functional acrylate, and
A photoinitiator combination triggered upon exposure to radiation at 365 nm of the electromagnetic spectrum comprising a bisacyl phosphine oxide and benzophenone, wherein the bisacyl phosphine oxide is present in an amount between about 1.5 and about 4 weight percent and the benzophenone is present in an amount between about 0.01 and about 1 weight percent and wherein when dispensed at a thickness of about 1 mm and exposed to UV radiation generated at a wavelength of 365 nm the composition cures through the thickness of the dispensed composition at a speed between 40 mm/sec to 100 mm/sec.
2. The composition of Claim 1, wherein the amount of benzophenone relative to bisacyl phosphine oxide is in the range of 0.005 to 0.25.
3. The composition of Claim 2, wherein the cure speed is 40 mm/sec.
4. The composition of Claim 1, wherein the amount of benzophenone relative to bisacyl phosphine oxide is in the range of 0.025 to 0.5.
5. The composition of Claim 4, wherein the cure speed is 100 mm/sec.
6. The composition of Claim 1, wherein the UV radiation is generated by a LED source.
7. The composition of Claim 1, wherein the UV radiation intensity is between about 120 to about 130 mW/cm2.
8. The composition of Claim 1, wherein the acrylate- functionalized hydrogenated polybutadiene has a molecular weight of about 3,000.
9. The composition of Claim 1, wherein the mono- functional acrylate is selected from the group consisting of 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2- hydroxyethyl acrylate, pentaerythritol triacrylate, 4- hydroxybutyl acrylate, isobornyl acrylate, cyclohexyl acrylate, tetrahydrofurfuryl acrylate, t-butylaminoethyl acrylate, cyanoethylacrylate, chloroethyl (meth) acrylate and lauryl acrylate, and their corresponding mono- functional (meth) acrylates .
10. A method of curing at 365 nm using an LED a UV curable composition at cure speeds within the range of about 40 mm/sec to about 100 mm/sec, comprising the steps of: a. dispensing onto a substrate a UV curable composition comprising a photoinitiator combination triggered upon exposure to radiation at 365 nm of the electromagnetic spectrum comprising a bisacyl phosphine oxide and benzophenone, wherein the bisacyl phosphine oxide is present in an amount between about 1.5 and about 4 weight percent and the benzophenone is present in an amount between about 0.01 and about 1 weight percent; and b. exposing the UV curable composition to UV radiation at a wavelength of 365 nm using an LED, such that the UV curable composition cures at cure speeds within the range of about 40 mm/sec to about 100 mm/sec.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/566,262 US7547735B1 (en) | 2006-12-04 | 2006-12-04 | UV curable compositions |
| US11/566,262 | 2006-12-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2008070030A1 true WO2008070030A1 (en) | 2008-06-12 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2007/024752 WO2008070030A1 (en) | 2006-12-04 | 2007-12-03 | Uv curable composition |
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| US (1) | US7547735B1 (en) |
| WO (1) | WO2008070030A1 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2925912B1 (en) * | 2007-12-26 | 2010-01-22 | Toray Plastics Europ | ROLL-IN POLYESTER FILM COMPRISING ON AT LEAST ONE OF ITS FACES, A CROSS-RESISTANT SCRATCH-RESISTANT COATING, PROCESS FOR OBTAINING THE POLYESTER FILM |
| EP2606098A4 (en) | 2010-08-18 | 2014-04-02 | Henkel Corp | Radiation curable temporary laminating adhesive for use in high temperature applications |
| US11242883B2 (en) * | 2016-12-22 | 2022-02-08 | Nylok Llc | Fastener sealing material and method |
| US20220081504A1 (en) * | 2019-01-11 | 2022-03-17 | Nitto Shinko Corporation | Curable composition |
| JPWO2021117804A1 (en) * | 2019-12-13 | 2021-06-17 | ||
| EP4093784A1 (en) * | 2020-03-02 | 2022-11-30 | Align Technology, Inc. | Low viscosity photo-curable resins for the direct fabrication of orthodontic appliances |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR950032245A (en) * | 1994-03-02 | 1995-12-20 | 베르너 발데크 | Dimeric Bisacylphosphines, Oxides and Sulphide Compounds and Compositions Comprising These Compounds |
| WO2002022697A1 (en) * | 2000-09-14 | 2002-03-21 | Ciba Specialty Chemicals Holding Inc. | Acylphosphine oxide photoinitiators in methacrylate casting resins |
| EP1376561A1 (en) * | 2002-06-19 | 2004-01-02 | Wellomer GmbH | Photocuring adhesive |
| US6714712B2 (en) * | 2001-01-11 | 2004-03-30 | Dsm N.V. | Radiation curable coating composition |
| US7109250B2 (en) * | 2001-11-20 | 2006-09-19 | Ciba Specialty Chemicals Corp. | Multimer forms of acylphosphines and their derivatives |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR950003224B1 (en) | 1992-04-10 | 1995-04-06 | 한국전기통신공사 | Fabricationg method of semiconductor device having multi-layer structure |
| US6709717B2 (en) * | 1998-06-09 | 2004-03-23 | Margrace Enterprises, Inc. | Method for making polymer surfaced composites |
| DE60115898T2 (en) * | 2000-06-22 | 2006-08-17 | Dsm Ip Assets B.V. | RADIATION-HARDENED DYED COATING COMPOSITION |
| US7495034B2 (en) * | 2002-02-22 | 2009-02-24 | Henkel Corporation | Deformable soft molding compositions |
| JP4170861B2 (en) * | 2003-09-04 | 2008-10-22 | 電気化学工業株式会社 | Photocurable resin composition |
| US20050101686A1 (en) * | 2003-11-07 | 2005-05-12 | Krohn Roy C. | UV curable composition for forming dielectric coatings and related method |
-
2006
- 2006-12-04 US US11/566,262 patent/US7547735B1/en active Active
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2007
- 2007-12-03 WO PCT/US2007/024752 patent/WO2008070030A1/en active Application Filing
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR950032245A (en) * | 1994-03-02 | 1995-12-20 | 베르너 발데크 | Dimeric Bisacylphosphines, Oxides and Sulphide Compounds and Compositions Comprising These Compounds |
| WO2002022697A1 (en) * | 2000-09-14 | 2002-03-21 | Ciba Specialty Chemicals Holding Inc. | Acylphosphine oxide photoinitiators in methacrylate casting resins |
| US6714712B2 (en) * | 2001-01-11 | 2004-03-30 | Dsm N.V. | Radiation curable coating composition |
| US7109250B2 (en) * | 2001-11-20 | 2006-09-19 | Ciba Specialty Chemicals Corp. | Multimer forms of acylphosphines and their derivatives |
| EP1376561A1 (en) * | 2002-06-19 | 2004-01-02 | Wellomer GmbH | Photocuring adhesive |
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| US7547735B1 (en) | 2009-06-16 |
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