GB567776A - Improvements in or relating to light activated adhesives - Google Patents
Improvements in or relating to light activated adhesivesInfo
- Publication number
- GB567776A GB567776A GB17105/42A GB1710542A GB567776A GB 567776 A GB567776 A GB 567776A GB 17105/42 A GB17105/42 A GB 17105/42A GB 1710542 A GB1710542 A GB 1710542A GB 567776 A GB567776 A GB 567776A
- Authority
- GB
- United Kingdom
- Prior art keywords
- vinyl
- phenyl
- satisfied
- oxygen
- group
- Prior art date
- 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
Links
- 239000000853 adhesive Substances 0.000 title 1
- 230000001070 adhesive effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 4
- -1 methyl vinyl Chemical group 0.000 abstract 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 abstract 2
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 abstract 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 abstract 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 150000002894 organic compounds Chemical class 0.000 abstract 2
- OJUGVDODNPJEEC-UHFFFAOYSA-N phenylglyoxal Chemical compound O=CC(=O)C1=CC=CC=C1 OJUGVDODNPJEEC-UHFFFAOYSA-N 0.000 abstract 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- 239000004926 polymethyl methacrylate Substances 0.000 abstract 2
- RXVBJUZEFSAYPW-UHFFFAOYSA-N 1,3-diphenylpropane-1,2,3-trione Chemical compound C=1C=CC=CC=1C(=O)C(=O)C(=O)C1=CC=CC=C1 RXVBJUZEFSAYPW-UHFFFAOYSA-N 0.000 abstract 1
- CARZNHSZGXCIJM-UHFFFAOYSA-N 1-(2-methylprop-2-enoyloxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)OC(=O)C(C)=C CARZNHSZGXCIJM-UHFFFAOYSA-N 0.000 abstract 1
- VOCDJQSAMZARGX-UHFFFAOYSA-N 1-ethenylpyrrolidine-2,5-dione Chemical compound C=CN1C(=O)CCC1=O VOCDJQSAMZARGX-UHFFFAOYSA-N 0.000 abstract 1
- KUIZKZHDMPERHR-UHFFFAOYSA-N 1-phenylprop-2-en-1-one Chemical class C=CC(=O)C1=CC=CC=C1 KUIZKZHDMPERHR-UHFFFAOYSA-N 0.000 abstract 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 abstract 1
- BKGMUAZOCAXREW-UHFFFAOYSA-N 13-hydroxytetracosan-12-one Chemical compound CCCCCCCCCCCC(O)C(=O)CCCCCCCCCCC BKGMUAZOCAXREW-UHFFFAOYSA-N 0.000 abstract 1
- XCBBNTFYSLADTO-UHFFFAOYSA-N 2,3-Octanedione Chemical compound CCCCCC(=O)C(C)=O XCBBNTFYSLADTO-UHFFFAOYSA-N 0.000 abstract 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 abstract 1
- SXAAVRUIADQETA-UHFFFAOYSA-N 2-chloro-n-(2-methoxyethyl)-n-(2-methylphenyl)acetamide Chemical compound COCCN(C(=O)CCl)C1=CC=CC=C1C SXAAVRUIADQETA-UHFFFAOYSA-N 0.000 abstract 1
- ZHESMCIWZWYNLC-UHFFFAOYSA-N 2-methylprop-2-enoyloxymethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCOC(=O)C(C)=C ZHESMCIWZWYNLC-UHFFFAOYSA-N 0.000 abstract 1
- BVEYJWQCMOVMAR-UHFFFAOYSA-N 5-Hydroxy-4-octanone Chemical compound CCCC(O)C(=O)CCC BVEYJWQCMOVMAR-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- MGYMHQJELJYRQS-UHFFFAOYSA-N Ascaridole Chemical compound C1CC2(C)OOC1(C(C)C)C=C2 MGYMHQJELJYRQS-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- 244000028419 Styrax benzoin Species 0.000 abstract 1
- 235000000126 Styrax benzoin Nutrition 0.000 abstract 1
- 235000008411 Sumatra benzointree Nutrition 0.000 abstract 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- MGYMHQJELJYRQS-ZJUUUORDSA-N ascaridole Natural products C1C[C@]2(C)OO[C@@]1(C(C)C)C=C2 MGYMHQJELJYRQS-ZJUUUORDSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 abstract 1
- 229960002130 benzoin Drugs 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 abstract 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 abstract 1
- QYFBSUCRERIFQO-UHFFFAOYSA-N dioxane-3,6-dione Chemical class O=C1CCC(=O)OO1 QYFBSUCRERIFQO-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- NHOGGUYTANYCGQ-UHFFFAOYSA-N ethenoxybenzene Chemical class C=COC1=CC=CC=C1 NHOGGUYTANYCGQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004744 fabric Substances 0.000 abstract 1
- 239000011521 glass Substances 0.000 abstract 1
- 229940015043 glyoxal Drugs 0.000 abstract 1
- 235000019382 gum benzoic Nutrition 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- GFAZHVHNLUBROE-UHFFFAOYSA-N hydroxymethyl propionaldehyde Natural products CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 abstract 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000400 lauroyl group Chemical group O=C([*])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 abstract 1
- 239000010985 leather Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 125000005395 methacrylic acid group Chemical class 0.000 abstract 1
- 229920003052 natural elastomer Polymers 0.000 abstract 1
- 229920001194 natural rubber Polymers 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- AKJNVJQPTQSJFM-UHFFFAOYSA-N o-ethenyl ethanethioate Chemical compound CC(=S)OC=C AKJNVJQPTQSJFM-UHFFFAOYSA-N 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 239000000123 paper Substances 0.000 abstract 1
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 229920003051 synthetic elastomer Polymers 0.000 abstract 1
- 239000005061 synthetic rubber Substances 0.000 abstract 1
- 239000006188 syrup Substances 0.000 abstract 1
- 235000020357 syrup Nutrition 0.000 abstract 1
- 239000002023 wood Substances 0.000 abstract 1
Classifications
-
- 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
- C08F291/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
- C08F291/18—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00 on to irradiated or oxidised macromolecules
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymerisation Methods In General (AREA)
- Laminated Bodies (AREA)
Abstract
Surfaces, of which not more than one is opaque, are bonded together by interposing a cementing layer comprising a liquid photopolymerizable organic compound containing a CH2 = C< group, and a photopolymerization catalyst and exposing it to light through a transparent member of the assembly. Specified photopolymerizable compounds are acrylic and methacrylic acids, esters, amides and nitriles; methyl vinyl and phenyl vinyl ketones; acrolein; vinyl thioacetate, propionate, isobutyrate, acetate and chloracetate; indene and styrene; divinyl and phenyl vinyl ethers; N - vinyl succinimide; vinyl naphthalene; vinylidene chloride; ethylidene dimethacrylate; methylene dimethacrylate; chloroprene and isoprene. The photopolymerization catalyst is an organic compound having a chain of two or three adjacent carbon atoms, each attached to one oxygen atom, at least one of the oxygen atoms being linked by a double bond to a carbon, no oxygen atom being attached to more than one of the carbon atoms, any valencies of the oxygen atoms not satisfied by an adjacent carbon atom being satisfied by hydrogen or a monovalent hydrocarbon radical, and the valencies of the carbon chain not satisfied by oxygen being satisfied by hydrogen or monovalent aliphatic or aromatic radicals. Preferred classes are alpha-carbonyl alcohols (R.CO.CHOH.R1), acyloins and polyketaldonyl compounds (R.(CO) .R1, where x = 2 or 3). Specified are glycollic aldehyde, benzoin, acetoin, butyroin, 3-hydroxy-4-methyl-pentanone-2, toluin, tert.-butylbenzoin, 12-hydroxy-13-ketotetracosane, o- and p-tert.-butyltoluin, diacetyl, pentandione - 2.3, octanedione - 2.3, 1-phenyl butanedione-1.2, benzil, 2.2-dimethyl-4 - phenyl butanedione - 3.4, glyoxal, phenyl glyoxal, diphenyl triketone and 1.2-cyclohexanedione. The photopolymerizable compound may be mixed with a polymer of a compound containing a CH2 = C< group to form a syrup before cementing, and may contain also benzoyl, lauroyl, acetyl, butyroyl, succinyl peroxides or ascaridole. Opaque surfaces listed include metals, cloth, paper, wood, leather, natural or synthetic rubber; and transparent surfaces listed include glass and polymeric materials derived from polymers of compounds containing a CH2 = C< group. The irradiation by light may be stopped before polymerization is complete. The invention is of particular use in the uniting of sheets of polymethyl methacrylate, e.g. for aircraft, and includes the filling of crevices in sheets of polymethyl methacrylate. Specifications 567,777 and 567,778 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US567776XA | 1941-12-31 | 1941-12-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB567776A true GB567776A (en) | 1945-03-02 |
Family
ID=22006524
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17105/42A Expired GB567776A (en) | 1941-12-31 | 1942-12-01 | Improvements in or relating to light activated adhesives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB567776A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3234065A (en) * | 1961-01-09 | 1966-02-08 | Best Plastic Container Corp | Method of laminating plastic film to plastic foam and of drawing the same, and foam-film laminates |
| US3982185A (en) * | 1975-06-25 | 1976-09-21 | General Electric Company | Lamp basing using UV curable adhesive |
| US4363689A (en) * | 1978-12-20 | 1982-12-14 | Henkel Corporation | Adhesive bonding process |
| US4772530A (en) * | 1986-05-06 | 1988-09-20 | The Mead Corporation | Photosensitive materials containing ionic dye compounds as initiators |
| US4874450A (en) * | 1987-01-29 | 1989-10-17 | The Mead Corporation | Laminating transparent or translucent materials using ionic dye-counter ion complexes |
| US4937159A (en) * | 1985-11-20 | 1990-06-26 | The Mead Corporation | Photosensitive materials and compositions containing ionic dye compounds as initiators and thiols as autooxidizers |
-
1942
- 1942-12-01 GB GB17105/42A patent/GB567776A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3234065A (en) * | 1961-01-09 | 1966-02-08 | Best Plastic Container Corp | Method of laminating plastic film to plastic foam and of drawing the same, and foam-film laminates |
| US3982185A (en) * | 1975-06-25 | 1976-09-21 | General Electric Company | Lamp basing using UV curable adhesive |
| US4363689A (en) * | 1978-12-20 | 1982-12-14 | Henkel Corporation | Adhesive bonding process |
| US4937159A (en) * | 1985-11-20 | 1990-06-26 | The Mead Corporation | Photosensitive materials and compositions containing ionic dye compounds as initiators and thiols as autooxidizers |
| US4772530A (en) * | 1986-05-06 | 1988-09-20 | The Mead Corporation | Photosensitive materials containing ionic dye compounds as initiators |
| US4874450A (en) * | 1987-01-29 | 1989-10-17 | The Mead Corporation | Laminating transparent or translucent materials using ionic dye-counter ion complexes |
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