KR102652309B1 - UV-curable solvent-free Pressure sensitive adhesive(PSA) composition and Manufacturing method thereof - Google Patents
UV-curable solvent-free Pressure sensitive adhesive(PSA) composition and Manufacturing method thereof Download PDFInfo
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- KR102652309B1 KR102652309B1 KR1020210144728A KR20210144728A KR102652309B1 KR 102652309 B1 KR102652309 B1 KR 102652309B1 KR 1020210144728 A KR1020210144728 A KR 1020210144728A KR 20210144728 A KR20210144728 A KR 20210144728A KR 102652309 B1 KR102652309 B1 KR 102652309B1
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- acrylate
- adhesive composition
- meth
- photocurable
- solvent
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- 239000000203 mixture Substances 0.000 title claims abstract description 75
- 238000004519 manufacturing process Methods 0.000 title abstract description 8
- 239000004820 Pressure-sensitive adhesive Substances 0.000 title 1
- 239000000853 adhesive Substances 0.000 claims abstract description 98
- 230000001070 adhesive effect Effects 0.000 claims abstract description 98
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims abstract description 31
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 24
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 55
- -1 diisocyanate compound Chemical class 0.000 claims description 23
- 239000000178 monomer Substances 0.000 claims description 20
- 238000010790 dilution Methods 0.000 claims description 15
- 239000012895 dilution Substances 0.000 claims description 15
- 229920005862 polyol Polymers 0.000 claims description 9
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 7
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 7
- 238000000016 photochemical curing Methods 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229920001451 polypropylene glycol Polymers 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 229920001610 polycaprolactone Polymers 0.000 claims description 3
- 239000004632 polycaprolactone Substances 0.000 claims description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 238000007865 diluting Methods 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 15
- 238000000034 method Methods 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 7
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 4
- 239000002390 adhesive tape Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 206010040844 Skin exfoliation Diseases 0.000 description 2
- 238000003848 UV Light-Curing Methods 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000005102 attenuated total reflection Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229930006711 bornane-2,3-dione Natural products 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
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
- 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
- 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
-
- 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
-
- 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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature
-
- 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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
- C09J2301/416—Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
본 발명은 광경화성 무용제 점착제 조성물 및 이의 제조방법에 관한 것이다. 구체적으로 본 발명은 우레탄아크릴레이트 올리고머 및 아크릴산을 포함하는 내열성이 우수한 광경화성 무용제 점착제 조성물에 대한 것이다.The present invention relates to a photocurable solvent-free adhesive composition and a method for producing the same. Specifically, the present invention relates to a photocurable solvent-free adhesive composition with excellent heat resistance containing urethane acrylate oligomer and acrylic acid.
Description
본 발명은 광경화성 무용제 점착제 조성물 및 이의 제조방법에 관한 것이다. 구체적으로 본 발명은 우레탄아크릴레이트 올리고머 및 아크릴산을 포함하는 내열성이 우수한 광경화성 무용제 점착제 조성물에 대한 것이다.The present invention relates to a photocurable solvent-free adhesive composition and a method for producing the same. Specifically, the present invention relates to a photocurable solvent-free adhesive composition with excellent heat resistance containing urethane acrylate oligomer and acrylic acid.
반도체 등의 전자 부품을 가공할 경우, 작업성 향상 및 전자 부품의 보호를 위해 점착제 조성물을 이용하여 전자 부품을 지지판에 고정하거나 점착 테이프를 전자 부품에 부착하는 방법을 이용한다. 또한 넓은 면적의 반도체 패키지를 다이싱해 다수의 개편화된 반도체 패키지를 얻을 경우에도 점착 테이프를 반도체 패키지에 부착하여 작업을 수행하기도 한다. 상기와 같은 점착제 또는 점착 테이프의 경우, 전자 부품을 강하게 고정해야 하기 때문에 강한 점착력이 요구되며, 또한, 공정 종료 후에는 전자 부품에 오염이 남지 않고 쉽게 박리되어야 한다.When processing electronic components such as semiconductors, a method of fixing the electronic components to a support plate using an adhesive composition or attaching an adhesive tape to the electronic components is used to improve workability and protect the electronic components. Additionally, when dicing a large area of a semiconductor package to obtain multiple individual semiconductor packages, the work is sometimes performed by attaching adhesive tape to the semiconductor package. In the case of the adhesive or adhesive tape as described above, strong adhesive force is required because the electronic components must be strongly fixed, and in addition, after the process is completed, the adhesive or adhesive tape must be easily peeled off without leaving any contamination on the electronic components.
이에 일반 점착제에 이중결합 등과 같은 광경화성 작용기를 도입하여 사용하는데, 예를 들어 경화하기 전에는 평소와 같이 점착제로서 부품을 고정하는 역할을 수행하다가, 공정 종료 후에는 쉽게 해체되도록, 광을 조사하여 상기 광경화성 작용기를 반응시켜 경화함으로써 박리력을 향상시킬 수 있다.Accordingly, a photocurable functional group such as a double bond is introduced into a general adhesive and used. For example, before curing, it plays the role of fixing parts as an adhesive as usual, but after the process is completed, light is irradiated so that it can be easily dismantled. Peelability can be improved by curing by reacting with a photocurable functional group.
한편 반도체 제조 공정 중 다수의 공정이 고온의 조건 하에서 수행되기 때문에 내열성이 매우 우수한 점착제가 필요하지만, 대부분의 광경화성 점착제는 고온의 공정에서 열분해되거나, 첨가제의 이동 현상에 의해 박리 단계에서의 점착력 저하 등의 문제가 발생하고 있다.Meanwhile, since many processes in the semiconductor manufacturing process are performed under high temperature conditions, an adhesive with excellent heat resistance is required. However, most photocurable adhesives are thermally decomposed in high temperature processes or the adhesive strength decreases in the peeling stage due to migration of additives. Problems such as these are occurring.
따라서, 점착력이 우수하고 광경화 후에 잔사없이 쉽게 박리되며, 무엇보다도 고온에서 장시간 버틸 수 있는 내열성이 우수한 광경화성 점착제 조성물에 대한 연구가 절실하게 필요한 실정이다.Therefore, there is an urgent need for research on a photocurable adhesive composition that has excellent adhesion, is easily peeled off without residue after photocuring, and, above all, has excellent heat resistance and can withstand high temperatures for a long time.
상기와 같은 문제를 해결하기 위해 본 발명은 우레탄아크릴레이트 올리고머 및 아크릴산을 포함하는, 내열성이 우수한 광경화성 무용제 점착제 조성물을 제공하는 것을 목적으로 한다.In order to solve the above problems, the purpose of the present invention is to provide a photocurable solvent-free adhesive composition containing excellent heat resistance and urethane acrylate oligomer and acrylic acid.
또한, 본 발명은 우레탄아크릴레이트 올리고머, 아크릴산 및 희석용 아크릴레이트 단량체를 포함하여, 점도조절이 가능하여 취급이 용이한 광경화성 무용제 점착제 조성물을 제공하는 것을 목적으로 한다.In addition, the purpose of the present invention is to provide a photocurable solvent-free adhesive composition that includes urethane acrylate oligomer, acrylic acid, and acrylate monomer for dilution, and is easy to handle due to its viscosity control.
본 발명은 하기 화학식 1로 표시되는 우레탄아크릴레이트 올리고머; 및 아크릴산;을 포함하는 광경화성 무용제 점착제 조성물을 제공한다.The present invention relates to a urethane acrylate oligomer represented by the following formula (1); And acrylic acid; provides a photocurable solvent-free adhesive composition containing.
[화학식 1][Formula 1]
(상기 화학식 1에서,(In Formula 1 above,
R1은 수소 또는 메틸이고,R 1 is hydrogen or methyl,
L1은 디이소시아네이트 화합물 유래 잔기이고,L 1 is a residue derived from a diisocyanate compound,
L2는 폴리올 화합물 유래 잔기이고,L 2 is a residue derived from a polyol compound,
m은 1 내지 200의 실수이다.)m is a real number from 1 to 200.)
본 발명의 일 실시예에 따른 광경화성 무용제 점착제 조성물에 있어서, 상기 광경화성 무용제 점착제 조성물은 희석용 아크릴레이트 단량체를 더 포함할 수 있다.In the photo-curable solvent-free adhesive composition according to an embodiment of the present invention, the photo-curable solvent-free adhesive composition may further include an acrylate monomer for dilution.
본 발명의 일 실시예에 따른 광경화성 무용제 점착제 조성물에 있어서, 상기 광경화성 무용제 점착제 조성물은 상온에서 측정한 점도가 500 내지 3000 cPs일 수 있다.In the photo-curable solvent-free adhesive composition according to an embodiment of the present invention, the photo-curable solvent-free adhesive composition may have a viscosity of 500 to 3000 cPs when measured at room temperature.
본 발명의 일 실시예에 따른 광경화성 무용제 점착제 조성물에 있어서, 상기 화학식 1에서 상기 L1은 이소포론디이소시아네이트 유래 잔기이며, 하기 화학식 2로 표시될 수 있다.In the photocurable solvent-free adhesive composition according to an embodiment of the present invention, in Formula 1, L 1 is a residue derived from isophorone diisocyanate and may be represented by Formula 2 below.
[화학식 2][Formula 2]
본 발명의 일 실시예에 따른 광경화성 무용제 점착제 조성물에 있어서, 상기 화학식 1에서 상기 폴리올 화합물은 중량평균분자량 1000 내지 3000g/mol의 폴리프로필렌글라이콜일 수 있다.In the photocurable solvent-free adhesive composition according to an embodiment of the present invention, the polyol compound in Formula 1 may be polypropylene glycol with a weight average molecular weight of 1000 to 3000 g/mol.
본 발명의 일 실시예에 따른 광경화성 무용제 점착제 조성물에 있어서, 상기 우레탄아크릴레이트 올리고머의 중량평균분자량 15,000 내지 50,000g/mol일 수 있다.In the photocurable solvent-free adhesive composition according to an embodiment of the present invention, the weight average molecular weight of the urethane acrylate oligomer may be 15,000 to 50,000 g/mol.
본 발명의 일 실시예에 따른 광경화성 무용제 점착제 조성물에 있어서, 상기 아크릴산은 우레탄아크릴레이트 올리고머 100 중량부에 대하여 0.1 내지 20 중량부로 포함될 수 있다.In the photocurable solvent-free adhesive composition according to an embodiment of the present invention, the acrylic acid may be included in an amount of 0.1 to 20 parts by weight based on 100 parts by weight of the urethane acrylate oligomer.
본 발명의 일 실시예에 따른 광경화성 무용제 점착제 조성물에 있어서, 상기 희석용 아크릴레이트 단량체는 상기 우레탄아크릴레이트 올리고머 100 중량부에 대하여 10 내지 200 중량부로 포함될 수 있다.In the photocurable solvent-free adhesive composition according to an embodiment of the present invention, the acrylate monomer for dilution may be included in an amount of 10 to 200 parts by weight based on 100 parts by weight of the urethane acrylate oligomer.
본 발명의 일 실시예에 따른 광경화성 무용제 점착제 조성물에 있어서, 상기 희석용 아크릴레이트 단량체는 메틸(메타)아크릴레이트, 에틸(메타)아크릴레이트, 부틸(메타)아크릴레이트, 테트라하이드로퍼퓨릴(메타)아크릴레이트, 이소데실(메타)아크릴레이트, 2-(2-에톡시에톡시)에틸 (메타)아크릴레이트, 스테아릴(메타)아크릴레이트, 라우릴(메타)아크릴레이트, 2-페녹시에틸 (메타)아크릴레이트, 아이소보닐(메타)아크릴레이트, 트리데실(메타)아크릴레이트, 폴리카프로락톤(메타)아크릴레이트 등으로 이루어진 군에서 선택되는 하나 또는 둘 이상의 조합일 수 있다.In the photocurable solvent-free adhesive composition according to an embodiment of the present invention, the acrylate monomer for dilution is methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, tetrahydrofurfuryl (meth) ) Acrylate, isodecyl (meth)acrylate, 2-(2-ethoxyethoxy)ethyl (meth)acrylate, stearyl (meth)acrylate, lauryl (meth)acrylate, 2-phenoxyethyl It may be one or a combination of two or more selected from the group consisting of (meth)acrylate, isobornyl (meth)acrylate, tridecyl (meth)acrylate, polycaprolactone (meth)acrylate, etc.
본 발명의 일 실시예에 따른 광경화성 무용제 점착제 조성물에 있어서, 상기 광경화성 무용제 점착제 조성물은 광개시제를 더 포함할 수 있다.In the photocurable solventless adhesive composition according to an embodiment of the present invention, the photocurable solventless adhesive composition may further include a photoinitiator.
본 발명의 일 실시예에 따른 광경화성 무용제 점착제 조성물에 있어서, 상기 광경화성 무용제 점착제 조성물을 95±5㎛의 두께로 도포하여 광경화한 점착제 경화물의 전단접착파괴온도(SAFT)가 150℃ 이상일 수 있다.In the photocurable solventless adhesive composition according to an embodiment of the present invention, the shear adhesive failure temperature (SAFT) of the adhesive cured by applying the photocurable solventless adhesive composition to a thickness of 95 ± 5㎛ and photocuring may be 150°C or higher. there is.
본 발명은 상술한 광경화성 무용제 점착제 조성물을 광경화시킨 점착제 경화물을 제공할 수 있다.The present invention can provide a cured adhesive obtained by photocuring the photocurable solvent-free adhesive composition described above.
본 발명의 광경화성 무용제 점착제 조성물은 우레탄아크릴레이트 및 아크릴산을 포함하여 우수한 점착력 및 내열성을 나타낸다. 무엇보다도 상기 점착제 조성물은 희석용 아크릴레이트 단량체를 포함함에 따라, 점조조절이 가능하여 취급이 용이하다는 장점이 있다.The photocurable solvent-free adhesive composition of the present invention contains urethane acrylate and acrylic acid and exhibits excellent adhesive strength and heat resistance. Above all, the adhesive composition has the advantage of being easy to handle as it contains an acrylate monomer for dilution, allowing for viscosity control.
도 1은 제조예 1의 (b)단계 전/후의 화합물에 대한 푸리에 변환 적외선 분광법(ATR FT-IR, Attenuated Total Reflection Fourier-transform infrared spectroscopy) 분석 결과이다.
도 2는 제조예 1의 우레탄아크릴레이트 올리고머의 H-NMR 분석 결과이다.
도 3은 실시예 1 내지 5 및 비교예 1에 따른 광경화성 무용제 점착제 조성물의 내열유지력을 측정하여 비교한 그래프이다.Figure 1 shows the results of Attenuated Total Reflection Fourier-transform infrared spectroscopy (ATR FT-IR) analysis of the compound before and after step (b) of Preparation Example 1.
Figure 2 shows the results of H-NMR analysis of the urethane acrylate oligomer of Preparation Example 1.
Figure 3 is a graph comparing the heat resistance of photocurable solvent-free adhesive compositions according to Examples 1 to 5 and Comparative Example 1.
이하 본 발명을 더욱 상세히 설명한다. 다만 하기 구체예 또는 실시예는 본 발명을 상세히 설명하기 위한 하나의 참조일 뿐 본 발명이 이에 한정되는 것은 아니며, 여러 형태로 구현될 수 있다.Hereinafter, the present invention will be described in more detail. However, the following specific examples or examples are only a reference for explaining the present invention in detail, and the present invention is not limited thereto, and may be implemented in various forms.
또한 달리 정의되지 않는 한, 모든 기술적 용어 및 과학적 용어는 본 발명이 속하는 당업자 중 하나에 의해 일반적으로 이해되는 의미와 동일한 의미를 갖는다. 본 발명에서 설명에 사용되는 용어는 단지 특정 구체예를 효과적으로 기술하기 위함이고 본 발명을 제한하는 것으로 의도되지 않는다. Additionally, unless otherwise defined, all technical and scientific terms have the same meaning as commonly understood by one of ordinary skill in the art to which the present invention pertains. The terminology used in the description herein is merely to effectively describe specific embodiments and is not intended to limit the invention.
또한 명세서 및 첨부된 특허청구범위에서 사용되는 단수 형태는 문맥에서 특별한 지시가 없는 한 복수 형태도 포함하는 것으로 의도할 수 있다. Additionally, as used in the specification and the appended claims, the singular forms “a,” “an,” and “the” are intended to also include the plural forms, unless the context clearly dictates otherwise.
또한, 본 명세서에서 특별한 언급 없이 사용된 단위는 중량을 기준으로 하며, 일 예로 % 또는 비의 단위는 중량% 또는 중량비를 의미하고, 중량%는 달리 정의되지 않는 한 전체 조성물 중 어느 하나의 성분이 조성물 내에서 차지하는 중량%를 의미한다.In addition, units used without special mention in this specification are based on weight, and as an example, the unit of % or ratio means weight % or weight ratio, and weight % refers to the amount of any one component of the entire composition unless otherwise defined. It refers to the weight percent occupied in the composition.
또한, 본 명세서에서 사용되는 수치 범위는 하한치와 상한치와 그 범위 내에서의 모든 값, 정의되는 범위의 형태와 폭에서 논리적으로 유도되는 증분, 이중 한정된 모든 값 및 서로 다른 형태로 한정된 수치 범위의 상한 및 하한의 모든 가능한 조합을 포함한다. 본 발명의 명세서에서 특별한 정의가 없는 한 실험 오차 또는 값의 반올림으로 인해 발생할 가능성이 있는 수치범위 외의 값 역시 정의된 수치범위에 포함된다.In addition, the numerical range used in this specification includes the lower limit and upper limit and all values within the range, increments logically derived from the shape and width of the defined range, all double-defined values, and the upper limit of the numerical range defined in different forms. and all possible combinations of the lower bounds. Unless otherwise specified in the specification of the present invention, values outside the numerical range that may occur due to experimental error or rounding of values are also included in the defined numerical range.
본 명세서에 기재된 "포함한다"는 "구비한다", "함유한다", "가진다" 또는 "특징으로 한다" 등의 표현과 등가의 의미를 가지는 개방형 기재이며, 추가로 열거되어 있지 않은 요소, 재료 또는 공정을 배제하지 않는다.As used herein, “comprises” is an open description with the same meaning as expressions such as “comprises,” “contains,” “has,” or “features,” and includes elements and materials that are not additionally listed. or does not exclude the process.
본 명세서에 기재된 "잔기"는 우레탄아크릴레이트 또는 우레탄 올리고머를 제조하기 위하여 사용된 화합물을 반응시킨 후, 작용기처럼 반응에 참여한 것이 아닌, 본래의 구조를 유지하고 있는 임의의 유기 구조를 의미한다. 구체적으로 우레탄 올리고머를 제조하기 위해 사용된 이소포론디이소시아네이트로부터 유래된 잔기는 하기 화학식 2로 표시될 수 있지만, 이에 제한되지 않는다.“Residue” as used herein refers to any organic structure that maintains its original structure and does not participate in the reaction like a functional group after reacting the compound used to produce urethane acrylate or urethane oligomer. Specifically, the residue derived from isophorone diisocyanate used to prepare the urethane oligomer may be represented by the following formula (2), but is not limited thereto.
[화학식 2][Formula 2]
본 명세서에 기재된 "상온"은 25±1℃을 의미한다.As used herein, “room temperature” means 25 ± 1°C.
본 명세서에 기재된 "올리고머"는 중량평균분자량이 500 g/mol 내지 50,000g/mol인 중합체를 의미하며, 일반적으로 하나 초과의 종의 단량체로부터 유래된 임의의 중합체를 의미한다.As used herein, “oligomer” refers to a polymer having a weight average molecular weight of 500 g/mol to 50,000 g/mol, and generally refers to any polymer derived from more than one species of monomer.
본 명세서에 기재된 "아크릴계"는 메타크릴계 및 아크릴계를 모두 포함한다.“Acrylic-based” as used herein includes both methacrylic-based and acrylic-based.
이하 본 발명에 대하여 자세하게 설명한다.Hereinafter, the present invention will be described in detail.
본 발명은 하기 화학식 1로 표시되는 우레탄아크릴레이트 올리고머; 및 아크릴산;을 포함하는 광경화성 무용제 점착제 조성물을 제공한다.The present invention relates to a urethane acrylate oligomer represented by the following formula (1); And acrylic acid; provides a photocurable solvent-free adhesive composition containing.
[화학식 1][Formula 1]
(상기 화학식 1에서, R1은 수소 또는 메틸이고, L1은 디이소시아네이트 화합물 유래 잔기이고, L2는 폴리올 화합물 유래 잔기이고, m은 1 내지 200의 실수, 구체적으로 m은 50 내지 150의 실수 이다.)(In Formula 1, R 1 is hydrogen or methyl, L 1 is a residue derived from a diisocyanate compound, L 2 is a residue derived from a polyol compound, m is a real number from 1 to 200, specifically m is a real number from 50 to 150. am.)
상기 화학식 1로 표시되는 우레탄아크릴레이트 올리고머는 상기 화학식 1의 디이소시아네이트 화합물와 상기 폴리올 화합물의 반응을 통해 우레탄 올리고머가 제조될 수 있으며, 상기 제조방법은 통상적이거나 공지된 방법을 제한없이 사용할 수 있다. 또한, 상기 우레탄 올리고머의 NCO말단을 2-헥실에틸아크릴레이트 또는 2-헥실에틸메타크릴레이트 등과 같이 말단에 하이드록시 작용기를 갖는 아크릴레이트계 단량체로 캡핑하여, 이중결합이 도입된 우레탄아크릴레이트 올리고머를 제조할 수 있지만, 이에 제한되지 않는다.The urethane acrylate oligomer represented by Formula 1 can be produced through the reaction of the diisocyanate compound of Formula 1 and the polyol compound, and the production method can be any conventional or known method without limitation. In addition, the NCO terminal of the urethane oligomer is capped with an acrylate-based monomer having a hydroxy functional group at the terminal, such as 2-hexylethyl acrylate or 2-hexylethyl methacrylate, to form a urethane acrylate oligomer with a double bond introduced. It can be manufactured, but is not limited to this.
상기 디이소시아네이트 화합물은 이소시아네이트 작용기가 2개 이상 존재하는 화합물이라면 크게 제한없이 사용할 수 있으며, 비제한적인 예로는 4,4'-디페닐메탄디이소시아네이트, 1,5'-나프탈렌디이소시아네이트, 1,4'-페닐렌디이소시아네이트, 헥사메틸렌디이소시아네이트, 1,4'-시클로헥산디이소시아네이트, 4,4'-디시클로헥실메탄디이소시아네이트, 이소포론디이소시아네이트 등을 들 수 있으며, 구체적으로 이소포론디이소시아네이트를 사용할 수 있다.The diisocyanate compound can be used without major limitations as long as it is a compound containing two or more isocyanate functional groups. Non-limiting examples include 4,4'-diphenylmethane diisocyanate, 1,5'-naphthalene diisocyanate, 1,4 '-phenylene diisocyanate, hexamethylene diisocyanate, 1,4'-cyclohexane diisocyanate, 4,4'-dicyclohexylmethane diisocyanate, isophorone diisocyanate, etc., and specifically, isophorone diisocyanate. You can use it.
바람직하게 상기 화학식 1에서 상기 L1은 이소포론디이소시아네이트 유래 잔기이며, 하기 화학식 2로 표시될 수 있다.Preferably, in Formula 1, L 1 is a residue derived from isophorone diisocyanate, and may be represented by Formula 2 below.
[화학식 2][Formula 2]
본 발명의 일 실시예에 따른 광경화성 무용제 점착제 조성물에 있어서, 상기 화학식 1에서 상기 폴리올은 두개 이상의 하이드록시 작용기를 갖는 화합물이라면 크게 제한없이 사용 가능하지만, 구체적으로 상기 폴리올은 중량평균분자량 500 내지 8000g/mol, 더욱 구체적으로 1000 내지 3000g/mol의 폴리프로필렌글라이콜 또는 폴리에틸렌글라이콜일 수 있다. 바람직하게 상기 화학식 1에서 상기 L2는 폴리프로필렌글라이콜 유래 잔기이며, 하기 화학식 3으로 표시될 수 있다.In the photocurable solvent-free adhesive composition according to an embodiment of the present invention, the polyol in Formula 1 can be used without major limitations as long as it is a compound having two or more hydroxy functional groups. Specifically, the polyol has a weight average molecular weight of 500 to 8000 g. /mol, more specifically, it may be 1000 to 3000 g/mol of polypropylene glycol or polyethylene glycol. Preferably, in Formula 1, L 2 is a residue derived from polypropylene glycol and may be represented by Formula 3 below.
[화학식 3][Formula 3]
상기 화학식 3에서 n은 1 내지 1000의 실수이며, 구체적으로 1 내지 500, 더욱 구체적으로 1 내지 100의 실수일 수 있다. In Formula 3, n is a real number from 1 to 1000, specifically 1 to 500, and more specifically 1 to 100.
본 발명의 일 실시예에 따른 광경화성 무용제 점착제 조성물에 있어서, 상기 우레탄아크릴레이트 올리고머의 중량평균분자량 5,000 내지 50,000g/mol, 구체적으로 15,000 내지 50,000g/mol, 더욱 구체적으로 30,000 내지 40,000g/mol일 수 있다. 상기 중량평균분자량을 만족하는 우레탄아크릴레이트 올리고머를 아크릴산과 함께 사용할 경우, 더욱 우수한 내열성을 갖는 광경화형 무용제 점착제 조성물을 제조할 수 있다.In the photocurable solvent-free adhesive composition according to an embodiment of the present invention, the weight average molecular weight of the urethane acrylate oligomer is 5,000 to 50,000 g/mol, specifically 15,000 to 50,000 g/mol, more specifically 30,000 to 40,000 g/mol. It can be. When a urethane acrylate oligomer satisfying the above weight average molecular weight is used together with acrylic acid, a photocurable solvent-free adhesive composition with more excellent heat resistance can be prepared.
본 발명의 일 실시예에 따른 광경화성 무용제 점착제 조성물에 있어서, 상기 아크릴산은 우레탄아크릴레이트 올리고머 100 중량부에 대하여 0.1 내지 20 중량부, 바람직하게 1 내지 15 중량부, 더욱 바람직하게 4 내지 11 중량부 또는 6 내지 11 중량부로 포함될 수 있다. 상기 범위를 만족할 경우, 더욱 우수한 내열성, 구체적으로 내열유지력이 더욱 향상되고 높은 전단접착파괴온도를 갖는 광경화성 무용제 점착제 조성물을 제조할 수 있어 바람직하다.In the photocurable solvent-free adhesive composition according to an embodiment of the present invention, the acrylic acid is contained in an amount of 0.1 to 20 parts by weight, preferably 1 to 15 parts by weight, more preferably 4 to 11 parts by weight, based on 100 parts by weight of urethane acrylate oligomer. Alternatively, it may be included in 6 to 11 parts by weight. When the above range is satisfied, it is preferable to manufacture a photocurable solvent-free adhesive composition with superior heat resistance, specifically improved heat resistance, and a high shear bond failure temperature.
본 발명의 일 실시예에 따른 광경화성 무용제 점착제 조성물에 있어서, 상기 광경화성 무용제 점착제 조성물은 희석용 아크릴레이트 단량체를 더 포함할 수 있다. 상기 희석용 아크릴레이트 단량체를 포함하는 광경화성 무용제 점착제 조성물은 점도조절이 가능하여, 취급을 용이하게 하여 개선된 작업성을 가질 수 있고, 뿐만 아니라, 희석용 아크릴레이트 단량체의 종류에 따라서 기계적물성 및 내열성 등을 더욱 향상시키는 데에 도움을 줄 수 있다.In the photo-curable solvent-free adhesive composition according to an embodiment of the present invention, the photo-curable solvent-free adhesive composition may further include an acrylate monomer for dilution. The photocurable solvent-free adhesive composition containing the acrylate monomer for dilution can control viscosity, facilitate handling, and have improved workability. In addition, depending on the type of acrylate monomer for dilution, mechanical properties and It can help to further improve heat resistance, etc.
본 발명의 일 실시예에 따른 광경화성 무용제 점착제 조성물에 있어서, 상기 희석용 아크릴레이트 단량체는 메틸(메타)아크릴레이트, 에틸(메타)아크릴레이트, 부틸(메타)아크릴레이트, 테트라하이드로퍼퓨릴(메타)아크릴레이트, 이소데실(메타)아크릴레이트, 2-(2-에톡시에톡시)에틸 (메타)아크릴레이트, 스테아릴(메타)아크릴레이트, 라우릴(메타)아크릴레이트, 2-페녹시에틸 (메타)아크릴레이트, 아이소보닐(메타)아크릴레이트, 트리데실(메타)아크릴레이트, 폴리카프로락톤(메타)아크릴레이트 등으로 이루어진 군에서 선택되는 하나 또는 둘 이상의 조합일 수 있고, 구체적으로 아이소보닐(메타)아크릴레이트 및 부틸(메타)아크릴레이트를 사용할 수 있다.In the photocurable solvent-free adhesive composition according to an embodiment of the present invention, the acrylate monomer for dilution is methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, tetrahydrofurfuryl (meth) ) Acrylate, isodecyl (meth)acrylate, 2-(2-ethoxyethoxy)ethyl (meth)acrylate, stearyl (meth)acrylate, lauryl (meth)acrylate, 2-phenoxyethyl It may be one or a combination of two or more selected from the group consisting of (meth)acrylate, isobornyl (meth)acrylate, tridecyl (meth)acrylate, polycaprolactone (meth)acrylate, etc., and specifically, Sobornyl (meth)acrylate and butyl (meth)acrylate can be used.
본 발명의 일 실시예에 따른 광경화성 무용제 점착제 조성물에 있어서, 상기 희석용 아크릴레이트 단량체는 상기 우레탄아크릴레이트 올리고머 100 중량부에 대하여 10 내지 200 중량부, 구체적으로 50 내지 150 중량부, 더욱 구체적으로 80 내지 120 중량부로 포함될 수 있지만, 목표하는 기계적 물성 및 내열성과 점도에 따라서 상기 희석용 아크릴레이트 단량체의 함량은 조절될 수 있다. 상기 범위를 만족할 경우, 제조된 점착제 조성물의 점도를 적절하게 조절하여 개선된 작업성을 가질 수 있어 좋다.In the photocurable solvent-free adhesive composition according to an embodiment of the present invention, the acrylate monomer for dilution is 10 to 200 parts by weight, specifically 50 to 150 parts by weight, more specifically, based on 100 parts by weight of the urethane acrylate oligomer. It may be included in 80 to 120 parts by weight, but the content of the acrylate monomer for dilution can be adjusted depending on the target mechanical properties, heat resistance, and viscosity. When the above range is satisfied, it is possible to have improved workability by appropriately controlling the viscosity of the prepared adhesive composition.
본 발명의 일 실시예에 따른 광경화성 무용제 점착제 조성물에 있어서, 상기 광경화성 무용제 점착제 조성물은 상온에서 측정한 점도가 500 내지 3000 cPs, 구체적으로 1000 내지 3000 cPs, 더욱 구체적으로 1000 내지 2500 cPs일 수 있다. 바람직하게는 상기 우레탄아크릴레이트 올리고머, 아크릴산 및 희석용 아크릴레이트 단량체를 모두 포함한 광경화성 무용제 점착제 조성물의 점도가 상기 점도범위를 만족할 수 있다. 상기 점도범위를 만족할 경우, 더욱 개선된 작업성을 가지며, 이를 통해 균일한 두께를 갖는 점착제를 도포할 수 있어 좋다.In the photocurable solvent-free adhesive composition according to an embodiment of the present invention, the photocurable solvent-free adhesive composition may have a viscosity measured at room temperature of 500 to 3000 cPs, specifically 1000 to 3000 cPs, and more specifically 1000 to 2500 cPs. there is. Preferably, the viscosity of the photocurable solvent-free adhesive composition containing all of the urethane acrylate oligomer, acrylic acid, and diluting acrylate monomer may satisfy the above viscosity range. When the above viscosity range is satisfied, workability is further improved, and through this, an adhesive having a uniform thickness can be applied.
본 발명의 일 실시예에 따른 광경화성 무용제 점착제 조성물에 있어서, 상기 광경화성 무용제 점착제 조성물은 광개시제를 더 포함할 수 있으며, 시중에 판매되는 제품을 제한없이 사용할 수 있다. 상기 광개시제의 비제한적인 예로, 알파-케톤계 화합물, 아세토페논계 화합물, 케탈계 화합물, 방향족 술포닐클로라이드계 화합물, 광활성 옥심계 화합물, 벤조페논계 화합물, 티오크산톤계 화합물, 캄포퀴논계 화합물, 할로겐화케톤계 화합물, 아실포스피녹시드계 화합물, 아실포스포네이트계 화합물 등으로 이루어진 군에서 선택되는 하나 또는 둘 이상을 사용할 수 있으며, 구체적으로 1-hydroxy-cyclohexylphenyl keton을 사용할 수 있지만, 이에 제한되지 않는다. 상기 광개시제는 방사선 또는 자외선에 의해 활성화되고, 탄소간의 이중결합을 활성화시켜 경화반응을 개시할 수 있다. 상기 광개시제는 광경화성 무용제 점착제 조성물 전체 중량에 대하여 0.001 내지 5 중량%, 구체적으로 0.01 내지 1 중량%로 포함될 수 있지만, 이에 제한되지 않는다.In the photocurable solventless adhesive composition according to an embodiment of the present invention, the photocurable solventless adhesive composition may further include a photoinitiator, and commercially available products may be used without limitation. Non-limiting examples of the photoinitiator include alpha-ketone-based compounds, acetophenone-based compounds, ketal-based compounds, aromatic sulfonyl chloride-based compounds, photoactive oxime-based compounds, benzophenone-based compounds, thioxanthone-based compounds, and camphorquinone-based compounds. , one or two or more selected from the group consisting of halogenated ketone-based compounds, acylphosphinoxide-based compounds, and acylphosphonate-based compounds can be used. Specifically, 1-hydroxy-cyclohexylphenyl keton can be used, but is limited thereto. It doesn't work. The photoinitiator is activated by radiation or ultraviolet rays and can initiate a curing reaction by activating double bonds between carbons. The photoinitiator may be included in an amount of 0.001 to 5% by weight, specifically 0.01 to 1% by weight, based on the total weight of the photocurable solvent-free adhesive composition, but is not limited thereto.
본 발명의 일 실시예에 따른 광경화성 무용제 점착제 조성물에 있어서, 상술한 광경화성 무용제 점착제 조성물은 통상적이거나 공지된 방법에 의하여 균일하게 교반될 수 있다.In the photo-curable solvent-free adhesive composition according to an embodiment of the present invention, the photo-curable solvent-free adhesive composition described above may be uniformly stirred by a conventional or known method.
본 발명은 상술한 광경화성 무용제 점착제 조성물을 광경화시킨 점착제 경화물을 제공할 수 있다. 상기 광경화성 무용제 점착제 조성물은 통상적이거나 공지된 방법에 의하여 광경화시킬 수 있고, 구체적으로 UV경화램프(254㎚)를 사용하거나 메탈할라이드 등을 이용하여 0.1 내지 5 J/㎠ UV-A의 광원을 조사할 수 있지만 이에 제한되지 않는다.The present invention can provide a cured adhesive obtained by photocuring the photocurable solvent-free adhesive composition described above. The photocurable solvent-free adhesive composition can be photocured by a conventional or known method, specifically using a UV curing lamp (254 nm) or a metal halide, etc., using a light source of 0.1 to 5 J/cm2 UV-A. You may, but are not limited to, investigate.
본 발명의 일 실시예에 따른 광경화성 무용제 점착제 조성물에 있어서, 상기 광경화성 무용제 점착제 조성물을 95±5㎛의 두께로 도포하여 광경화한 점착제 경화물의 전단접착파괴온도(SAFT)가 100℃ 이상, 150℃ 이상, 더욱 구체적으로 160 내지 190℃일 수 있다. 상기 전단접착파괴온도의 측정방법은 본 발명에 기재된 내열전단접착파괴온도의 측정방법을 따를 수 있지만, 이에 제한되지 않는다. 상기 범위를 만족하는 광경화성 무용제 점착제 조성물은 매우 우수한 내열성을 가질 수 있으며, 이를 이용하여 고온에서 수행하는 공정에 고정용 점착제 등의 용도로 사용할 수 있다.In the photo-curable solvent-free adhesive composition according to an embodiment of the present invention, the shear adhesive failure temperature (SAFT) of the adhesive cured by applying the photo-curable solvent-free adhesive composition to a thickness of 95 ± 5 μm and photo-curing is 100 ° C. or higher, It may be 150°C or higher, more specifically 160 to 190°C. The method of measuring the shear bond failure temperature may follow the method of measuring the heat-resistant shear bond failure temperature described in the present invention, but is not limited thereto. A photocurable solvent-free adhesive composition that satisfies the above range can have excellent heat resistance, and can be used as an adhesive for fixing processes performed at high temperatures.
이하 실시예 및 비교예를 통해 본 발명에 따른 광경화성 무용제 점착제 조성물 및 이의 제조방법에 대하여 더욱 상세히 설명한다. 다만 하기 실시예는 본 발명을 상세히 설명하기 위한 하나의 참조일 뿐 본 발명이 이에 한정되는 것은 아니며, 여러 형태로 구현될 수 있다. 또한 달리 정의되지 않은 한, 모든 기술적 용어 및 과학적 용어는 본 발명이 속하는 당업자 중 하나에 의해 일반적으로 이해되는 의미와 동일한 의미를 갖는다. 또한, 본 발명에서 설명에 사용되는 용어는 단지 특정 실시예를 효과적으로 기술하기 위함이고, 본 발명을 제한하는 것으로 의도되지 않는다.Hereinafter, the photocurable solvent-free adhesive composition and its manufacturing method according to the present invention will be described in more detail through examples and comparative examples. However, the following examples are only a reference for explaining the present invention in detail, and the present invention is not limited thereto, and may be implemented in various forms. Additionally, unless otherwise defined, all technical and scientific terms have the same meaning as commonly understood by one of ordinary skill in the art to which the present invention pertains. Additionally, the terms used in the description in the present invention are only intended to effectively describe specific embodiments and are not intended to limit the present invention.
[물성측정방법][Physical property measurement method]
1. 점착력 테스트(180℃ T-Peel Test) : 실시예 및 비교예에서 제조한 점착제와 광개시제로 0.5중량부의 irgacure 184를 배합한 조성물을 50±1 ㎛ 두께의 이형 필름 상부에 도포하고, 도포된 상기 광학용 점착제 조성물의 상부에 추가적인 이형 필름을 배치하였다. 이어서, UV 경화를 위해 메탈할라이드 등을 이용하여 1.55 J/㎠ UV-A의 광원을 5회 조사하였다. 상기 점착제층이 형성된 PET 필름을 폭이 25㎜가 되도록 절단하여 점착력 테스트용 시편을 총 10개 제조하였으며, SUS 304기재상에 상기 제조된 시편을 150㎜ x 25㎜의 점착면이 형성되도록 접착시킨 후 2kg의 롤러로 2회 왕복하고, 상기 시편을 상온에서 24시간 동안 방치하였다. 상온에서 universal testing machine (UTM, 만능재료시험기)을 이용하여 상기 10개의 시편을 5㎜/mim.의 속도 조건에서 180℃ 점착력을 측정하였으며, 이외의 조건은 KS T 1028에 의거하였다. 측정된 점착력의 최소값 및 최대값을 제외한 나머지의 평균값을 계산하여 하기 표 2에 나타내었다.1. Adhesion Test (180°C T-Peel Test): A composition containing 0.5 parts by weight of irgacure 184 as a photoinitiator and the adhesive prepared in Examples and Comparative Examples was applied on top of a release film with a thickness of 50 ± 1 ㎛, and the applied An additional release film was placed on top of the optical adhesive composition. Next, for UV curing, a light source of 1.55 J/cm2 UV-A was irradiated five times using metal halide, etc. The PET film on which the adhesive layer was formed was cut to a width of 25 mm to prepare a total of 10 specimens for adhesion testing, and the prepared specimens were adhered to a SUS 304 substrate to form an adhesive surface of 150 mm x 25 mm. Then, it was reciprocated twice with a 2kg roller, and the specimen was left at room temperature for 24 hours. The adhesion of the above 10 specimens was measured at 180°C at a speed of 5 mm/mim. using a universal testing machine (UTM) at room temperature, and other conditions were based on KS T 1028. The average values of the measured adhesive forces excluding the minimum and maximum values were calculated and shown in Table 2 below.
2. 루프텍 테스트(Loop Tack Test) : 상기 점착력 테스트용 시편과 동일하게 루프텍 테스트용 시편을 10개 제조하였으며, 기재상에 점착면적이 60㎜ x 25.4㎜가 형성되도록 접착시킨 후 2kg의 롤러로 2회 왕복하여 시편을 제조하였다. 이어서, 상기 시편의 루프텍을 UTM(만능재료시험기)을 이용하여 측정하였으며, 기재는 SUS 304이었고, 박리속도는 5㎜/mim.이였다. 측정된 루프텍의 최소값 및 최대값을 제외한 나머지의 평균값을 계산하여 하기 표 2에 나타내었다.2. Loop Tack Test: 10 loop tack test specimens were manufactured in the same manner as the above adhesion test specimens, and were glued on the substrate to form an adhesive area of 60 mm x 25.4 mm, followed by a 2 kg roller. A specimen was prepared by making two round trips. Next, the loop tack of the specimen was measured using a UTM (Universal Testing Machine), the substrate was SUS 304, and the peeling speed was 5 mm/mim. The average values of the measured LoopTek excluding the minimum and maximum values were calculated and shown in Table 2 below.
3. 내열유지력(150℃ Holding force) : 상기 점착력 테스트용 시편과 동일하게 내열유지력 테스트용 시편을 5개 제조하였으며, 기재상에 점착면적이 25㎜ x 25㎜가 형성되도록 접착시킨 후 2kg의 롤러로 2회 왕복하여 시편을 제조하였다. 이어서 150℃로 예열된 오븐에 상기 제조된 시편과 시편에 1kg의 추를 매달아 점착제가 얼마나 오랫동안 추의 하중을 견디는지, 추가 떨어지는 시간을 측정하였으며, 평균값을 계산하여 하기 표 2에 나타내었다.3. Heat-resisting holding force (150℃ Holding force): Five specimens for heat-resisting holding force test were manufactured in the same manner as the above-described adhesion test specimens, and were glued on the substrate to form an adhesive area of 25 mm x 25 mm, followed by a 2 kg roller. A specimen was prepared by making two round trips. Next, a 1kg weight was hung on the prepared specimen and the specimen in an oven preheated to 150°C to measure how long the adhesive could withstand the load of the weight and the time the weight fell. The average values were calculated and shown in Table 2 below.
4. 내열전단접착파괴온도(shear adhesive failure temperature, SAFT) : 상기 점착력 테스트용 시편과 동일하게 내열전단접착파괴온도 테스트용 시편을 5개 제조하였다. 이어서 50℃로 예열된 오븐에 상기 제조된 시편과 시편에 1k의 추를 매달고, 오븐의 온도를 0.5℃/min의 속도로 180℃까지 승온시켜 추가 떨어지는 온도를 측정하였으며, 평균값을 계산하여 하기 표 2에 나타내었다.4. Shear adhesive failure temperature (SAFT): Five specimens for the heat-resistant shear adhesive failure temperature test were manufactured in the same manner as the specimens for the adhesion test. Subsequently, a 1k weight was hung on the prepared specimen and the specimen in an oven preheated to 50°C, the temperature of the oven was raised to 180°C at a rate of 0.5°C/min, the falling temperature of the weight was measured, and the average value was calculated as shown in the table below. It is shown in 2.
5. 점도 측정 : 실시예 및 비교예에서 제조한 점착제 조성물의 점도를 브룩필드 점도계로 25±1 ℃의 온도에서 LV-type spindle No.63로 측정하였다.5. Viscosity measurement: The viscosity of the adhesive composition prepared in Examples and Comparative Examples was measured using a Brookfield viscometer at a temperature of 25±1°C using LV-type spindle No.63.
[제조예 1] 우레탄아크릴레이트 올리고머(UAO)의 제조[Preparation Example 1] Preparation of urethane acrylate oligomer (UAO)
(a) 500mL 둥근 바닥의 분리 가능한 플라스크에 중량평균분자량 약 2000g/mol(n=34)의 폴리프로플렌글라이콜(PPG) 200g을 이소보닐아크릴레이트(IBOA) 57.15g에 녹인 후 이소포론디이소시아네이트(IPDI) 24.45g를 투입하고, 반응기 내부 온도를 60 ℃로 승온시킨 후, 촉매인 DBTDL(dibutyltin-dilaurate)을 100ppm 투입하여 반응을 개시하였다. 우레탄 반응은 6시간동안 교반하여 반응을 진행하였다. 반응을 통해 제조된 우레탄 올리고머의 NCO피크를 FT-IR을 통해 측정하여 적정한 수준의 NCO 값을 얻었을 때, 말단봉쇄반응을 진행하였다. (a) In a 500mL round-bottom, separable flask, 200g of polypropylene glycol (PPG) with a weight average molecular weight of about 2000g/mol (n=34) was dissolved in 57.15g of isobornyl acrylate (IBOA), and then dissolved in isophoronedi. 24.45 g of isocyanate (IPDI) was added, the temperature inside the reactor was raised to 60°C, and 100 ppm of DBTDL (dibutyltin-dilaurate), a catalyst, was added to initiate the reaction. The urethane reaction was carried out by stirring for 6 hours. The NCO peak of the urethane oligomer prepared through the reaction was measured through FT-IR, and when an appropriate level of NCO value was obtained, the end blocking reaction was performed.
(b) 이어서 2-하이드록시에틸아크릴레이트(HEA)를 투입하여 상기 제조된 우레탄 올리고머의 NCO 말단을 HEA로 캡핑하였다. 제조된 합성물을 (b)단계 전/후로 푸리에 변환 적외선 분광법(ATR FT-AIR)으로 분석하여 NCO 피크가 소멸됨을 확인함으로써(도 1), 최종적으로 우레탄아크릴레이트 올리고머를 수득하였다. 또한, 상기 우레탄아크릴레이트 올리고머를 H-NMR(분석조건: CDCl3, 300MHz, 298K)로 분석하여 도 2에 도시하였으며, GPC로 분석한 상기 우레탄아크릴레이트 올리고머의 중량평균분자량은 33,547 g/mol으로 측정되었다. 또한, 상기 분석을 통해 m은 약 91임을 확인하였다. (b) Then, 2-hydroxyethyl acrylate (HEA) was added to cap the NCO terminal of the prepared urethane oligomer with HEA. The prepared composite was analyzed by Fourier transform infrared spectroscopy (ATR FT-AIR) before and after step (b) to confirm that the NCO peak disappeared (Figure 1), thereby finally obtaining a urethane acrylate oligomer. In addition, the urethane acrylate oligomer was analyzed by H-NMR (analysis conditions: CDCl 3 , 300 MHz, 298 K) and is shown in Figure 2. The weight average molecular weight of the urethane acrylate oligomer analyzed by GPC was 33,547 g/mol. It was measured. In addition, through the above analysis, it was confirmed that m was about 91.
[실시예 1 내지 5 및 비교예 1 및 2] 광경화성 무용제 점착제 조성물의 제조[Examples 1 to 5 and Comparative Examples 1 and 2] Preparation of photocurable solvent-free adhesive composition
상기 제조예 1의 우레탄아크릴레이트 올리고머(UAO);에 희석용 아크릴단량체인 이소보닐아크릴레이트(IBOA) 및 부틸아크릴레이트(BA) 및 아크릴산(AA);을 하기 표 1에 기재된 투입량에 따라 혼합하고, 광개시제인 Irgacure 184를 0.08g 투입하여 실시예 1 내지 5 및 비교예 1 및 2에 따른 광경화성 무용제 점착제 조성물을 제조하였다. 여기서, 상기 제조예 1의 샘플은 우레탄아크릴레이트 올리고머(UAO) 80중량% 및 IBOA 20중량%이 포함되어있다. 상기 아크릴산은 상기 우레탄아크릴레이트 올리고머 100 중량부에 대하여 1, 3, 5, 7, 10중량부가 되도록 계산하여, 하기 표 1에 기재된 투입량을 투입하였다. 상기 제조한 광경화성 무용제 점착제 조성물의 물성을 측정하여 하기 표 2에 나타내었다.The urethane acrylate oligomer (UAO) of Preparation Example 1 was mixed with isobornyl acrylate (IBOA), butylacrylate (BA), and acrylic acid (AA), which are acrylic monomers for dilution, according to the dosage shown in Table 1 below. , 0.08 g of Irgacure 184, a photoinitiator, was added to prepare photocurable solvent-free adhesive compositions according to Examples 1 to 5 and Comparative Examples 1 and 2. Here, the sample of Preparation Example 1 contains 80% by weight of urethane acrylate oligomer (UAO) and 20% by weight of IBOA. The acrylic acid was calculated to be 1, 3, 5, 7, and 10 parts by weight based on 100 parts by weight of the urethane acrylate oligomer, and the amounts shown in Table 1 below were added. The physical properties of the photocurable solvent-free adhesive composition prepared above were measured and shown in Table 2 below.
[gf/in.]Looptech
[gf/in.]
[gf/in.]adhesiveness
[gf/in.]
[시간]Heat resistance
[hour]
상기 표 2에서 보는 바와 같이, 실시예에서 AA가 첨가된 경우 점착력, 내열유지력 및 내열전단접착파괴온도가 더욱 향상된다는 것을 확인하였다. 구체적으로 이러한 현상은 AA의 -COOH와 우레탄아크릴레이트 올리고머의 수소결합에 의하여 인력 및 응집력이 향상되었기 때문이라고 판단하였다. 반면, 유리전이온도가 높은 AA의 특성으로 인해 AA의 함량이 증가할수록 루프텍은 감소하는 경향을 보였다.As shown in Table 2, it was confirmed that when AA was added in the examples, the adhesion, heat resistance holding power, and heat resistance shear bond failure temperature were further improved. Specifically, it was determined that this phenomenon was due to improved attraction and cohesion through hydrogen bonding between -COOH of AA and urethane acrylate oligomer. On the other hand, due to the characteristics of AA with a high glass transition temperature, loop tack tended to decrease as the AA content increased.
특히, 실시예 3 내지 5의 경우, 내열전단접착파괴온도가 180℃로 측정되며, 나아가 180℃에 도달한 뒤에도 실시예 3은 8시간, 실시예 4 및 5의 경우는 18시간 이상 유지됨을 확인하였으며, 이를 통해 본 발명에 따른 광경화형 무용제 점착제 조성물이 우수한 내열성을 갖는다는 것을 확인할 수 있었다. 또한, 실시예 1 내지 5 및 비교예 1은 점도가 1000 내지 3000 cPs로 측정된 반면에, 비교예 2의 경우 점도가 너무 높았으며, 따라서 코팅성이 미흡하고 균일한 두께를 갖는 시편을 제조하지 못하였다.In particular, in the case of Examples 3 to 5, the heat-resistant shear adhesive failure temperature was measured at 180°C, and furthermore, even after reaching 180°C, it was confirmed that Example 3 was maintained for 8 hours and in Examples 4 and 5, it was maintained for more than 18 hours. Through this, it was confirmed that the photocurable solvent-free adhesive composition according to the present invention has excellent heat resistance. In addition, the viscosity of Examples 1 to 5 and Comparative Example 1 was measured to be 1000 to 3000 cPs, whereas the viscosity of Comparative Example 2 was too high, and therefore the coating properties were insufficient and a specimen with a uniform thickness could not be manufactured. I couldn't do it.
이상과 같이 본 발명에서는 특정된 사항들과 한정된 실시예에 의해 설명되었으나 이는 본 발명의 보다 전반적인 이해를 돕기 위해서 제공된 것일 뿐, 본 발명은 상기의 실시예에 한정되는 것은 아니며, 본 발명이 속하는 분야에서 통상의 지식을 가진 자라면 이러한 기재로부터 다양한 수정 및 변형이 가능하다. As described above, the present invention has been described with specific details and limited embodiments, but these are provided only to facilitate a more general understanding of the present invention, and the present invention is not limited to the above embodiments, and the field to which the present invention belongs is not limited to the above embodiments. Those skilled in the art can make various modifications and variations from this description.
따라서, 본 발명의 사상은 설명된 실시예에 국한되어 정해져서는 아니되며, 후술하는 특허청구범위뿐 아니라 이 특허청구범위와 균등하거나 등가적 변형이 있는 모든 것들은 본 발명 사상의 범주에 속한다고 할 것이다.Accordingly, the spirit of the present invention should not be limited to the described embodiments, and the scope of the patent claims described below as well as all modifications that are equivalent or equivalent to the scope of this patent claim shall fall within the scope of the spirit of the present invention. .
Claims (12)
전체 조성물 내에 하이드록시기를 함유하는 아크릴레이트 단량체를 포함하지 않는 것인 광경화성 무용제 점착제 조성물.
[화학식 1]
(상기 화학식 1에서,
R1은 수소 또는 메틸이고,
L1은 디이소시아네이트 화합물 유래 잔기이고,
L2는 폴리올 화합물 유래 잔기이고,
m은 1 내지 200의 실수이다.)Urethane acrylate oligomer represented by the following formula (1); Acrylate monomer for dilution; and acrylic acid; wherein the acrylic acid is included in an amount of 0.1 to 20 parts by weight based on 100 parts by weight of the urethane acrylate oligomer,
The overall composition does not contain acrylate monomers containing hydroxy groups. Photocurable solvent-free adhesive composition.
[Formula 1]
(In Formula 1 above,
R 1 is hydrogen or methyl,
L 1 is a residue derived from a diisocyanate compound,
L 2 is a residue derived from a polyol compound,
m is a real number from 1 to 200.)
상기 광경화성 무용제 점착제 조성물은 상온에서 측정한 점도가 500 내지 3000 cPs인 광경화성 무용제 점착제 조성물.According to clause 1,
The photocurable solventless adhesive composition has a viscosity of 500 to 3000 cPs measured at room temperature.
상기 화학식 1에서 상기 L1은 이소포론디이소시아네이트 유래 잔기이며, 하기 화학식 2로 표시되는 것인 광경화성 무용제 점착제 조성물.
[화학식 2]
According to clause 1,
In Formula 1, L 1 is a residue derived from isophorone diisocyanate, and is represented by the following Formula 2: A photocurable solvent-free adhesive composition.
[Formula 2]
상기 화학식 1에서 상기 폴리올 화합물은 중량평균분자량 1000 내지 3000g/mol의 폴리프로필렌글라이콜인 광경화성 무용제 점착제 조성물.According to clause 1,
In Formula 1, the polyol compound is a photocurable solvent-free adhesive composition wherein the polyol compound is polypropylene glycol with a weight average molecular weight of 1000 to 3000 g/mol.
상기 우레탄아크릴레이트 올리고머의 중량평균분자량 15,000 내지 50,000g/mol인 광경화성 무용제 점착제 조성물.According to clause 1,
A photocurable solvent-free adhesive composition wherein the urethane acrylate oligomer has a weight average molecular weight of 15,000 to 50,000 g/mol.
상기 희석용 아크릴레이트 단량체는 상기 우레탄아크릴레이트 올리고머 100 중량부에 대하여 10 내지 200 중량부로 포함되는 광경화성 무용제 점착제 조성물.According to clause 1,
The photocurable solvent-free adhesive composition wherein the diluting acrylate monomer is contained in an amount of 10 to 200 parts by weight based on 100 parts by weight of the urethane acrylate oligomer.
상기 희석용 아크릴레이트 단량체는 메틸(메타)아크릴레이트, 에틸(메타)아크릴레이트, 부틸(메타)아크릴레이트, 테트라하이드로퍼퓨릴(메타)아크릴레이트, 이소데실(메타)아크릴레이트, 2-(2-에톡시에톡시)에틸 (메타)아크릴레이트, 스테아릴(메타)아크릴레이트, 라우릴(메타)아크릴레이트, 2-페녹시에틸 (메타)아크릴레이트, 아이소보닐(메타)아크릴레이트, 트리데실(메타)아크릴레이트, 폴리카프로락톤(메타)아크릴레이트로 이루어진 군에서 선택되는 하나 또는 둘 이상의 조합인 광경화성 무용제 점착제 조성물.According to clause 1,
The acrylate monomers for dilution include methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, isodecyl (meth)acrylate, 2-(2) -Ethoxyethoxy)ethyl (meth)acrylate, stearyl (meth)acrylate, lauryl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, isobornyl (meth)acrylate, tri. A photocurable solvent-free adhesive composition that is one or a combination of two or more selected from the group consisting of decyl (meth)acrylate and polycaprolactone (meth)acrylate.
상기 광경화성 무용제 점착제 조성물은 광개시제를 더 포함하는 광경화성 무용제 점착제 조성물.According to clause 1,
The photocurable solventless adhesive composition further includes a photoinitiator.
상기 광경화성 무용제 점착제 조성물을 95±5㎛의 두께로 도포하여 광경화한 점착제 경화물의 전단접착파괴온도(SAFT)가 150℃ 이상인 광경화성 무용제 점착제 조성물.According to clause 1,
A photocurable solventless adhesive composition having a shear failure temperature (SAFT) of 150°C or more of the cured adhesive obtained by applying the photocurable solventless adhesive composition to a thickness of 95 ± 5㎛ and photocuring it.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014091755A (en) | 2012-11-01 | 2014-05-19 | Hayakawa Rubber Co Ltd | Adhesive tape for laser joint |
| KR102229885B1 (en) | 2020-07-01 | 2021-03-18 | 동우 화인켐 주식회사 | Adhesive Composition and Adhesive Sheet Using the Same |
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| KR20130067532A (en) * | 2011-12-14 | 2013-06-25 | 동우 화인켐 주식회사 | Composition for resin type light guide panel, backlight unit comprising the light guide panel manufactured by thereof and liquid crystal display including the backlight unit |
| JP6097132B2 (en) * | 2013-04-22 | 2017-03-15 | 昭和電工株式会社 | Photocurable composition for transparent adhesive sheet, adhesive sheet using the same, and use thereof |
| DE102016224169A1 (en) * | 2016-12-05 | 2018-06-07 | Tesa Se | Reactive 2-component adhesive system in film form with improved moist heat resistance |
| KR102019587B1 (en) * | 2018-01-16 | 2019-09-06 | 방현수 | Urethan acrylate oligomer and adhesive composition comprising the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014091755A (en) | 2012-11-01 | 2014-05-19 | Hayakawa Rubber Co Ltd | Adhesive tape for laser joint |
| KR102229885B1 (en) | 2020-07-01 | 2021-03-18 | 동우 화인켐 주식회사 | Adhesive Composition and Adhesive Sheet Using the Same |
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