CA1297621C - Systeme adhesif photoreticulable a base d'amides - Google Patents

Systeme adhesif photoreticulable a base d'amides

Info

Publication number: CA1297621C
Authority: CA; Canada
Prior art keywords: composition; percent; acrylamide; weight; acrylate
Prior art date: 1987-01-29
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA000557766A

Other languages

English (en)

Inventor

James M. Hillman

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Dymax Corp

Original Assignee

Dymax Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1987-01-29

Filing date

1988-01-29

Publication date

1992-03-17

1988-01-29 Application filed by Dymax Corp filed Critical Dymax Corp

1992-03-17 Application granted granted Critical

1992-03-17 Publication of CA1297621C publication Critical patent/CA1297621C/fr

2009-03-17 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

230000001070 adhesive effect Effects 0.000 title claims description 31
239000000853 adhesive Substances 0.000 title claims description 30
150000001408 amides Chemical class 0.000 title description 13
230000005855 radiation Effects 0.000 claims abstract description 24
239000000203 mixture Substances 0.000 claims description 76
239000000178 monomer Substances 0.000 claims description 21
239000000945 filler Substances 0.000 claims description 19
-1 amide com-pound Chemical class 0.000 claims description 18
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 13
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 11
238000000034 method Methods 0.000 claims description 11
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 claims description 10
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 8
239000007787 solid Substances 0.000 claims description 8
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 7
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
FLCAEMBIQVZWIF-UHFFFAOYSA-N 6-(dimethylamino)-2-methylhex-2-enamide Chemical compound CN(C)CCCC=C(C)C(N)=O FLCAEMBIQVZWIF-UHFFFAOYSA-N 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 7
229920000570 polyether Polymers 0.000 claims description 7
FZHYLXLEEBXHEG-UHFFFAOYSA-N 2-methyl-3-(2-methylpropoxy)prop-2-enamide Chemical compound CC(C)COC=C(C)C(N)=O FZHYLXLEEBXHEG-UHFFFAOYSA-N 0.000 claims description 6
230000000694 effects Effects 0.000 claims description 6
239000007788 liquid Substances 0.000 claims description 6
TURITJIWSQEMDB-UHFFFAOYSA-N 2-methyl-n-[(2-methylprop-2-enoylamino)methyl]prop-2-enamide Chemical compound CC(=C)C(=O)NCNC(=O)C(C)=C TURITJIWSQEMDB-UHFFFAOYSA-N 0.000 claims description 5
KFTHUBZIEMOORC-UHFFFAOYSA-N 2-methylbut-2-enamide Chemical compound CC=C(C)C(N)=O KFTHUBZIEMOORC-UHFFFAOYSA-N 0.000 claims description 5
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 5
239000004721 Polyphenylene oxide Substances 0.000 claims description 5
229920001971 elastomer Polymers 0.000 claims description 5
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 5
OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 claims description 5
FYNUIZCNFQNHQP-UHFFFAOYSA-N n-(6-methylheptyl)prop-2-enamide Chemical compound CC(C)CCCCCNC(=O)C=C FYNUIZCNFQNHQP-UHFFFAOYSA-N 0.000 claims description 5
JBLADNFGVOKFSU-UHFFFAOYSA-N n-cyclohexyl-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NC1CCCCC1 JBLADNFGVOKFSU-UHFFFAOYSA-N 0.000 claims description 5
229920002635 polyurethane Polymers 0.000 claims description 5
239000004814 polyurethane Substances 0.000 claims description 5
CLHPBURJMZXHFZ-UHFFFAOYSA-N (1,2,2-trimethylcyclohexyl) prop-2-enoate Chemical compound CC1(C)CCCCC1(C)OC(=O)C=C CLHPBURJMZXHFZ-UHFFFAOYSA-N 0.000 claims description 4
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 claims description 4
PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 claims description 4
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 4
239000011837 N,N-methylenebisacrylamide Substances 0.000 claims description 4
239000002202 Polyethylene glycol Substances 0.000 claims description 4
ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 4
HZVYXCKFHRBBBT-UHFFFAOYSA-N n-[1,5,5-tris(prop-2-enoylamino)pentyl]prop-2-enamide Chemical compound C=CC(=O)NC(NC(=O)C=C)CCCC(NC(=O)C=C)NC(=O)C=C HZVYXCKFHRBBBT-UHFFFAOYSA-N 0.000 claims description 4
229920001223 polyethylene glycol Polymers 0.000 claims description 4
230000004044 response Effects 0.000 claims description 4
239000000806 elastomer Substances 0.000 claims description 3
239000003999 initiator Substances 0.000 claims description 3
229940117913 acrylamide Drugs 0.000 claims 3
XPFDXWGYIODGQN-UHFFFAOYSA-N n-(4-aminophenyl)-3-hydroxyprop-2-enamide Chemical compound NC1=CC=C(NC(=O)C=CO)C=C1 XPFDXWGYIODGQN-UHFFFAOYSA-N 0.000 claims 3
239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims 2
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 claims 2
OWXRDALCCNTBRI-UHFFFAOYSA-N 2-methyl-1-(3-methylthiophen-2-yl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CSC(C(=O)C(C)(C)N2CCOCC2)=C1C OWXRDALCCNTBRI-UHFFFAOYSA-N 0.000 claims 1
230000036647 reaction Effects 0.000 claims 1
239000003522 acrylic cement Substances 0.000 abstract description 3
150000003857 carboxamides Chemical class 0.000 abstract description 3
238000009472 formulation Methods 0.000 description 9
239000000126 substance Substances 0.000 description 9
239000000463 material Substances 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000004615 ingredient Substances 0.000 description 6
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
229910000077 silane Inorganic materials 0.000 description 4
QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 3
VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 3
102100026735 Coagulation factor VIII Human genes 0.000 description 3
101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000011521 glass Substances 0.000 description 3
229920000058 polyacrylate Polymers 0.000 description 3
DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
AEBNPEXFDZBTIB-UHFFFAOYSA-N 2-methyl-4-phenylbut-2-enamide Chemical compound NC(=O)C(C)=CCC1=CC=CC=C1 AEBNPEXFDZBTIB-UHFFFAOYSA-N 0.000 description 2
GOLYTOVWWJCSJM-UHFFFAOYSA-N 3-butoxy-2-methylprop-2-enamide Chemical compound CCCCOC=C(C)C(N)=O GOLYTOVWWJCSJM-UHFFFAOYSA-N 0.000 description 2
229920002799 BoPET Polymers 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
229920013646 Hycar Polymers 0.000 description 2
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
239000005041 Mylar™ Substances 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
150000001252 acrylic acid derivatives Chemical class 0.000 description 2
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
238000000576 coating method Methods 0.000 description 2
230000007423 decrease Effects 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
229940088644 n,n-dimethylacrylamide Drugs 0.000 description 2
YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 2
XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
229920001451 polypropylene glycol Polymers 0.000 description 2
239000000047 product Substances 0.000 description 2
239000005060 rubber Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
239000002562 thickening agent Substances 0.000 description 2
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
QJUCCGSXGKTYBT-UHFFFAOYSA-N 2,4,4-trimethylpent-2-enamide Chemical compound NC(=O)C(C)=CC(C)(C)C QJUCCGSXGKTYBT-UHFFFAOYSA-N 0.000 description 1
INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 1
CDSULTPOCMWJCM-UHFFFAOYSA-N 4h-chromene-2,3-dione Chemical class C1=CC=C2OC(=O)C(=O)CC2=C1 CDSULTPOCMWJCM-UHFFFAOYSA-N 0.000 description 1
IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-UHFFFAOYSA-N 0.000 description 1
229920006384 Airco Polymers 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
UXMQORVHJMUQFD-UHFFFAOYSA-N Heptanophenone Chemical compound CCCCCCC(=O)C1=CC=CC=C1 UXMQORVHJMUQFD-UHFFFAOYSA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
241000751119 Mila <angiosperm> Species 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
102400000830 Saposin-B Human genes 0.000 description 1
101800001697 Saposin-B Proteins 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
244000028419 Styrax benzoin Species 0.000 description 1
235000000126 Styrax benzoin Nutrition 0.000 description 1
235000008411 Sumatra benzointree Nutrition 0.000 description 1
UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
229920006311 Urethane elastomer Polymers 0.000 description 1
MWGMEGAYPPQWFG-UHFFFAOYSA-N [SiH4].OC(=O)C=C Chemical compound [SiH4].OC(=O)C=C MWGMEGAYPPQWFG-UHFFFAOYSA-N 0.000 description 1
229920000800 acrylic rubber Polymers 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000002318 adhesion promoter Substances 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000008901 benefit Effects 0.000 description 1
WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
229960002130 benzoin Drugs 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
150000008366 benzophenones Chemical class 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
230000032798 delamination Effects 0.000 description 1
ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
239000000975 dye Substances 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
235000019382 gum benzoic Nutrition 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229940102838 methylmethacrylate Drugs 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
229920003052 natural elastomer Polymers 0.000 description 1
229920001194 natural rubber Polymers 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
239000002530 phenolic antioxidant Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
239000005056 polyisocyanate Substances 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
150000004053 quinones Chemical class 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229920003051 synthetic elastomer Polymers 0.000 description 1
239000005061 synthetic rubber Substances 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000002023 wood Substances 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Adhesives Or Adhesive Processes (AREA)
Polymerisation Methods In General (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Macromonomer-Based Addition Polymer (AREA)

CA000557766A 1987-01-29 1988-01-29 Systeme adhesif photoreticulable a base d'amides Expired - Fee Related CA1297621C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US854987A	1987-01-29	1987-01-29
US008,549		1987-01-29

Publications (1)

Publication Number	Publication Date
CA1297621C true CA1297621C (fr)	1992-03-17

Family

ID=21732227

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000557766A Expired - Fee Related CA1297621C (fr)	1987-01-29	1988-01-29	Systeme adhesif photoreticulable a base d'amides

Country Status (4)

Country	Link
JP (1)	JPS63225673A (fr)
AU (1)	AU1299388A (fr)
CA (1)	CA1297621C (fr)
WO (1)	WO1988005791A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2585370B2 (ja) *	1988-05-18	1997-02-26	富士重工業株式会社	皿取装置におけるクランプ機構
JP5956325B2 (ja) *	2012-12-13	2016-07-27	富士フイルム株式会社	硬化性組成物及び重合性化合物

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3862021A (en) *	1972-02-17	1975-01-21	Asahi Chemical Ind	Polymerizable compositions and laminated articles bonded
JPS5034966B2 (fr) *	1972-07-24	1975-11-12
US4210713A (en) *	1973-02-01	1980-07-01	Nippon Paint Co., Ltd.	Photo-curable composition for coating containing an unsaturated urethane modified polymer
US4181752A (en) *	1974-09-03	1980-01-01	Minnesota Mining And Manufacturing Company	Acrylic-type pressure sensitive adhesives by means of ultraviolet radiation curing
US4131529A (en) *	1976-06-05	1978-12-26	Basf Aktiengesellschaft	Photoinitiators for photopolymerizable coating compositions
US4133909A (en) *	1977-01-26	1979-01-09	Mobil Oil Corporation	Radiation curable aqueous coatings
JPS5493026A (en) *	1977-12-29	1979-07-23	Teijin Ltd	Photosensitive adhesive
JPS584953A (ja) *	1981-07-01	1983-01-12	Toshiba Corp	半導体装置
NZ205990A (en) *	1982-11-05	1987-04-30	Deltaglass Sa	Radiation-curable, urethane acrylate-containing liquid adhesive composition and glass laminates
NZ205989A (en) *	1982-11-05	1987-04-30	Deltaglass Sa	Radiation curable, urethane acrylate-containing fluid adhesive compositions and glass laminates

1988
- 1988-01-27 JP JP1476688A patent/JPS63225673A/ja active Pending
- 1988-01-28 AU AU12993/88A patent/AU1299388A/en not_active Abandoned
- 1988-01-28 WO PCT/US1988/000252 patent/WO1988005791A1/fr not_active Ceased
- 1988-01-29 CA CA000557766A patent/CA1297621C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
AU1299388A (en)	1988-08-24
JPS63225673A (ja)	1988-09-20
WO1988005791A1 (fr)	1988-08-11

Legal Events

Date	Code	Title	Description
2008-03-17	MKLA	Lapsed

Publication	Publication Date	Title
US4964938A (en)	1990-10-23	Bonding method using photocurable acrylate adhesive containing perester/tautomeric acid adhesion promoter
EP0281581B1 (fr)	1992-05-20	Adhesif sensible a la pression a base de caoutchouc vulcanise par irradiation
EP0044166B1 (fr)	1985-11-21	Composition adhésive ténacifiée à l'aide de butadiène
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