TWI815027B - 可固化組成物 - Google Patents
可固化組成物 Download PDFInfo
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- TWI815027B TWI815027B TW109124600A TW109124600A TWI815027B TW I815027 B TWI815027 B TW I815027B TW 109124600 A TW109124600 A TW 109124600A TW 109124600 A TW109124600 A TW 109124600A TW I815027 B TWI815027 B TW I815027B
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- Prior art keywords
- monomer
- curable composition
- ring
- acrylate
- polymerizable material
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- 239000000203 mixture Substances 0.000 title claims abstract description 69
- 239000000178 monomer Substances 0.000 claims abstract description 111
- 239000000463 material Substances 0.000 claims abstract description 45
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims abstract description 11
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical group O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 claims abstract description 7
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical group O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000003999 initiator Substances 0.000 claims abstract description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 23
- 239000000758 substrate Substances 0.000 claims description 17
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical class C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 15
- 230000004580 weight loss Effects 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 238000010438 heat treatment Methods 0.000 claims description 12
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 claims description 11
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 claims description 10
- 238000003860 storage Methods 0.000 claims description 10
- MKRBAPNEJMFMHU-UHFFFAOYSA-N 1-benzylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CC=CC=C1 MKRBAPNEJMFMHU-UHFFFAOYSA-N 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 claims description 7
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 claims description 7
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 6
- SOEDHYUFNWMILE-UHFFFAOYSA-N naphthalen-1-yl prop-2-enoate Chemical compound C1=CC=C2C(OC(=O)C=C)=CC=CC2=C1 SOEDHYUFNWMILE-UHFFFAOYSA-N 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 230000003044 adaptive effect Effects 0.000 abstract description 4
- 239000010410 layer Substances 0.000 description 42
- 238000001723 curing Methods 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000012360 testing method Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 230000005855 radiation Effects 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 230000009477 glass transition Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- YNSSPVZNXLACMW-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)-3-ethyl-5-methylphenyl]methyl]-2-ethyl-6-methylphenyl]pyrrole-2,5-dione Chemical compound C=1C(C)=C(N2C(C=CC2=O)=O)C(CC)=CC=1CC(C=C1CC)=CC(C)=C1N1C(=O)C=CC1=O YNSSPVZNXLACMW-UHFFFAOYSA-N 0.000 description 4
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 4
- -1 Hexylmaleimide (N-cyclohexylmaleimide) Chemical compound 0.000 description 4
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 4
- 238000003848 UV Light-Curing Methods 0.000 description 4
- 238000005530 etching Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000001127 nanoimprint lithography Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 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 2
- AXTADRUCVAUCRS-UHFFFAOYSA-N 1-(2-hydroxyethyl)pyrrole-2,5-dione Chemical compound OCCN1C(=O)C=CC1=O AXTADRUCVAUCRS-UHFFFAOYSA-N 0.000 description 2
- CVKDEEISKBRPEQ-UHFFFAOYSA-N 1-(4-nitrophenyl)pyrrole-2,5-dione Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1C(=O)C=CC1=O CVKDEEISKBRPEQ-UHFFFAOYSA-N 0.000 description 2
- PUKLCKVOVCZYKF-UHFFFAOYSA-N 1-[2-(2,5-dioxopyrrol-1-yl)ethyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCN1C(=O)C=CC1=O PUKLCKVOVCZYKF-UHFFFAOYSA-N 0.000 description 2
- FERLGYOHRKHQJP-UHFFFAOYSA-N 1-[2-[2-[2-(2,5-dioxopyrrol-1-yl)ethoxy]ethoxy]ethyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCOCCOCCN1C(=O)C=CC1=O FERLGYOHRKHQJP-UHFFFAOYSA-N 0.000 description 2
- IPJGAEWUPXWFPL-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(N2C(C=CC2=O)=O)=C1 IPJGAEWUPXWFPL-UHFFFAOYSA-N 0.000 description 2
- XBHHVVHQVJQMSL-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1.O=C1C=CC(=O)N1C1=CC=CC=C1 XBHHVVHQVJQMSL-UHFFFAOYSA-N 0.000 description 2
- YEKDUBMGZZTUDY-UHFFFAOYSA-N 1-tert-butylpyrrole-2,5-dione Chemical compound CC(C)(C)N1C(=O)C=CC1=O YEKDUBMGZZTUDY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000007373 indentation Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- BSSNZUFKXJJCBG-UPHRSURJSA-N (z)-but-2-enediamide Chemical compound NC(=O)\C=C/C(N)=O BSSNZUFKXJJCBG-UPHRSURJSA-N 0.000 description 1
- OYRSKXCXEFLTEY-UHFFFAOYSA-N 1-[2-[2-[2-[2-(2,5-dioxopyrrol-1-yl)ethoxy]ethoxy]ethoxy]ethyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCOCCOCCOCCN1C(=O)C=CC1=O OYRSKXCXEFLTEY-UHFFFAOYSA-N 0.000 description 1
- ZLLQQGWNYVJPAS-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound C1(CCCCC1)N1C(C=CC1=O)=O.C1(CCCCC1)N1C(C=CC1=O)=O ZLLQQGWNYVJPAS-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- ZJGBFJBMTKEFNQ-UHFFFAOYSA-N 3-(2,5-dioxopyrrol-1-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC(N2C(C=CC2=O)=O)=C1 ZJGBFJBMTKEFNQ-UHFFFAOYSA-N 0.000 description 1
- XHVHQOXNVIKIPR-UHFFFAOYSA-N C(C)C=1C=C(C=C(C1N1C(C=CC1=O)=O)C)CC1=CC(=C(C(=C1)C)N1C(C=CC1=O)=O)CC.C(C)C=1C=C(C=C(C1N1C(C=CC1=O)=O)C)CC1=CC(=C(C(=C1)C)N1C(C=CC1=O)=O)CC Chemical compound C(C)C=1C=C(C=C(C1N1C(C=CC1=O)=O)C)CC1=CC(=C(C(=C1)C)N1C(C=CC1=O)=O)CC.C(C)C=1C=C(C=C(C1N1C(C=CC1=O)=O)C)CC1=CC(=C(C(=C1)C)N1C(C=CC1=O)=O)CC XHVHQOXNVIKIPR-UHFFFAOYSA-N 0.000 description 1
- SZHYHKIPEUWYJD-UHFFFAOYSA-N C1(C=CC(N1CCCCN1C(C=CC1=O)=O)=O)=O.C1(C=CC(N1CCCCN1C(C=CC1=O)=O)=O)=O Chemical compound C1(C=CC(N1CCCCN1C(C=CC1=O)=O)=O)=O.C1(C=CC(N1CCCCN1C(C=CC1=O)=O)=O)=O SZHYHKIPEUWYJD-UHFFFAOYSA-N 0.000 description 1
- GZJFQZYRHBXUGB-UHFFFAOYSA-N ClC1=C(C(=CC(=C1)Cl)Cl)N1C(C=CC1=O)=O.ClC1=C(C(=CC(=C1)Cl)Cl)N1C(C=CC1=O)=O Chemical compound ClC1=C(C(=CC(=C1)Cl)Cl)N1C(C=CC1=O)=O.ClC1=C(C(=CC(=C1)Cl)Cl)N1C(C=CC1=O)=O GZJFQZYRHBXUGB-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical group CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- GHAZCVNUKKZTLG-UHFFFAOYSA-N N-ethyl-succinimide Natural products CCN1C(=O)CCC1=O GHAZCVNUKKZTLG-UHFFFAOYSA-N 0.000 description 1
- HDFGOPSGAURCEO-UHFFFAOYSA-N N-ethylmaleimide Chemical compound CCN1C(=O)C=CC1=O HDFGOPSGAURCEO-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical group 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- RSVDRWTUCMTKBV-UHFFFAOYSA-N sbb057044 Chemical compound C12CC=CC2C2CC(OCCOC(=O)C=C)C1C2 RSVDRWTUCMTKBV-UHFFFAOYSA-N 0.000 description 1
- 238000007573 shrinkage measurement Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
-
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/36—Amides or imides
- C08F222/40—Imides, e.g. cyclic imides
- C08F222/402—Alkyl substituted imides
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
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- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
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- C08F220/1807—C7-(meth)acrylate, e.g. heptyl (meth)acrylate or benzyl (meth)acrylate
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
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- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
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- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
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- C08F220/1806—C6-(meth)acrylate, e.g. (cyclo)hexyl (meth)acrylate or phenyl (meth)acrylate
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- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
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- C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
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- C08F222/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
- C08F222/1025—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate of aromatic dialcohols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F224/00—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 a heterocyclic ring containing oxygen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—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 an aromatic carbocyclic ring
- C08F212/34—Monomers containing two or more unsaturated aliphatic radicals
- C08F212/36—Divinylbenzene
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Laminated Bodies (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16/562,716 US11345772B2 (en) | 2019-09-06 | 2019-09-06 | Curable composition |
| US16/562,716 | 2019-09-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW202110909A TW202110909A (zh) | 2021-03-16 |
| TWI815027B true TWI815027B (zh) | 2023-09-11 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW109124600A TWI815027B (zh) | 2019-09-06 | 2020-07-21 | 可固化組成物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US11345772B2 (https=) |
| JP (1) | JP7663515B2 (https=) |
| KR (1) | KR102790744B1 (https=) |
| CN (1) | CN114245818B (https=) |
| TW (1) | TWI815027B (https=) |
| WO (1) | WO2021045843A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11434312B2 (en) | 2020-12-15 | 2022-09-06 | Canon Kabushiki Kaisha | Photocurable composition for forming cured layers with high thermal stability |
| US11434313B2 (en) * | 2020-12-16 | 2022-09-06 | Canon Kabushiki Kaisha | Curable composition for making cured layer with high thermal stability |
| US12247133B2 (en) * | 2022-02-17 | 2025-03-11 | Canon Kabushiki Kaisha | Photocurable composition including a reactive polymer |
| US11878935B1 (en) * | 2022-12-27 | 2024-01-23 | Canon Kabushiki Kaisha | Method of coating a superstrate |
| TW202535989A (zh) | 2023-12-28 | 2025-09-16 | 德商默克專利有限公司 | 化合物 |
| TW202545859A (zh) | 2023-12-28 | 2025-12-01 | 德商默克專利有限公司 | 化合物 |
| WO2025142787A2 (en) | 2023-12-28 | 2025-07-03 | Canon Kabushiki Kaisha | Curable composition |
| TW202536000A (zh) | 2023-12-28 | 2025-09-16 | 日商佳能股份有限公司 | 可硬化之組成物 |
| TW202600500A (zh) | 2024-03-15 | 2026-01-01 | 德商默克專利有限公司 | 可硬化之組成物 |
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| CN101068839A (zh) * | 2004-12-01 | 2007-11-07 | 3M创新有限公司 | 支化聚合物 |
| EP2423278A1 (en) * | 2010-08-31 | 2012-02-29 | Fujifilm Corporation | Ink composition, image forming method and printed matter |
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| US4939070A (en) | 1986-07-28 | 1990-07-03 | Brunsvold William R | Thermally stable photoresists with high sensitivity |
| US5274059A (en) | 1988-12-27 | 1993-12-28 | Nippon Oil And Fats Co., Ltd. | Maleimide copolymer and process for preparing same |
| FR2672896B1 (fr) | 1991-02-15 | 1993-06-04 | Aerospatiale Soc Nat Industrielle | Procede de durcissement sous rayonnement ionisant d'une resine bis-maleimide et d'un materiau composite utilisant cette resine. |
| JPH0625359A (ja) * | 1992-07-07 | 1994-02-01 | Kuraray Co Ltd | 低複屈折性成形材料 |
| US5618857A (en) * | 1993-06-24 | 1997-04-08 | Loctite Corporation | Impregnation sealant composition of superior high temperature resistance, and method of making same |
| IT1291204B1 (it) | 1997-03-18 | 1998-12-29 | Comau Spa | Dispositivo per il montaggio automatizzato dei semi-coni di una valvola di un motore a combustione interna. |
| US5990202A (en) * | 1997-10-31 | 1999-11-23 | Hewlett-Packard Company | Dual encapsulation technique for preparing ink-jets inks |
| US6479211B1 (en) | 1999-05-26 | 2002-11-12 | Fuji Photo Film Co., Ltd. | Positive photoresist composition for far ultraviolet exposure |
| US20040029044A1 (en) * | 2002-08-08 | 2004-02-12 | 3M Innovative Properties Company | Photocurable composition |
| US8088548B2 (en) | 2007-10-23 | 2012-01-03 | Az Electronic Materials Usa Corp. | Bottom antireflective coating compositions |
| ATE537195T1 (de) * | 2008-09-09 | 2011-12-15 | Agfa Graphics Nv | Strahlungshärtbare zusammensetzungen |
| CN102428112B (zh) * | 2009-05-18 | 2014-01-08 | 爱克发印艺公司 | 可聚合的聚合物光引发剂和辐射可固化组合物 |
| JP5504769B2 (ja) | 2009-09-07 | 2014-05-28 | Ｊｎｃ株式会社 | 重合性組成物 |
| JP2012214532A (ja) | 2011-03-31 | 2012-11-08 | Taiyo Holdings Co Ltd | インクジェット用硬化性樹脂組成物、その硬化物及び当該硬化物を有するプリント配線板 |
| CN104093779A (zh) * | 2012-01-19 | 2014-10-08 | 伊索拉美国有限公司 | 合成树脂以及由其制造的清漆、预浸料和层压板 |
| US8815395B2 (en) | 2012-07-13 | 2014-08-26 | Eastman Kodak Company | High density polymer particles and dispersion of same |
| JP6004971B2 (ja) * | 2013-03-12 | 2016-10-12 | 富士フイルム株式会社 | 加飾シート成形物又はインモールド成形品製造用インクジェットインク組成物、加飾シート成形物又はインモールド成形品製造用インクジェット記録方法、加飾シート成形物又はインモールド成形品製造用インクセット、加飾シート成形物又はインモールド成形品製造用加飾シート、加飾シート成形物、及び、インモールド成形品の製造方法 |
| JP6163801B2 (ja) | 2013-03-13 | 2017-07-19 | Jnc株式会社 | 硬化膜 |
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| EP2960306B1 (en) | 2014-06-26 | 2020-12-23 | Agfa Nv | Aqueous radiation curable inkjet inks |
| JP2016160334A (ja) | 2015-02-27 | 2016-09-05 | 富士フイルム株式会社 | インクジェット記録用インク組成物、及び、インクジェット記録方法 |
| JP2017181617A (ja) * | 2016-03-29 | 2017-10-05 | 株式会社日本触媒 | 感光性樹脂組成物及びその硬化膜 |
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2019
- 2019-09-06 US US16/562,716 patent/US11345772B2/en active Active
-
2020
- 2020-07-13 WO PCT/US2020/041803 patent/WO2021045843A1/en not_active Ceased
- 2020-07-13 JP JP2021573142A patent/JP7663515B2/ja active Active
- 2020-07-13 KR KR1020227008714A patent/KR102790744B1/ko active Active
- 2020-07-13 CN CN202080056033.1A patent/CN114245818B/zh active Active
- 2020-07-21 TW TW109124600A patent/TWI815027B/zh active
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| CN101068839A (zh) * | 2004-12-01 | 2007-11-07 | 3M创新有限公司 | 支化聚合物 |
| EP2423278A1 (en) * | 2010-08-31 | 2012-02-29 | Fujifilm Corporation | Ink composition, image forming method and printed matter |
Also Published As
| Publication number | Publication date |
|---|---|
| US20210070906A1 (en) | 2021-03-11 |
| KR20220050921A (ko) | 2022-04-25 |
| WO2021045843A1 (en) | 2021-03-11 |
| JP2022546754A (ja) | 2022-11-08 |
| CN114245818B (zh) | 2023-10-31 |
| KR102790744B1 (ko) | 2025-04-04 |
| TW202110909A (zh) | 2021-03-16 |
| US11345772B2 (en) | 2022-05-31 |
| JP7663515B2 (ja) | 2025-04-16 |
| CN114245818A (zh) | 2022-03-25 |
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