ES334593A1 - Improvements in or relating to adhesives or sealing compounds - Google Patents
Improvements in or relating to adhesives or sealing compoundsInfo
- Publication number
- ES334593A1 ES334593A1 ES334593A ES334593A ES334593A1 ES 334593 A1 ES334593 A1 ES 334593A1 ES 334593 A ES334593 A ES 334593A ES 334593 A ES334593 A ES 334593A ES 334593 A1 ES334593 A1 ES 334593A1
- Authority
- ES
- Spain
- Prior art keywords
- methacrylate
- esters
- methylolcyclopentane
- alcohol
- dioxa
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 3
- 239000000853 adhesive Substances 0.000 title abstract 2
- 230000001070 adhesive effect Effects 0.000 title abstract 2
- 238000007789 sealing Methods 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 abstract 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- -1 methacrylate ester Chemical class 0.000 abstract 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 abstract 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 abstract 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 abstract 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 abstract 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 abstract 2
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 abstract 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 abstract 1
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 abstract 1
- SPTHWAJJMLCAQF-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene;hydrogen peroxide Chemical class OO.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-N 0.000 abstract 1
- CAKWRXVKWGUISE-UHFFFAOYSA-N 1-methylcyclopentan-1-ol Chemical compound CC1(O)CCCC1 CAKWRXVKWGUISE-UHFFFAOYSA-N 0.000 abstract 1
- HQOVXPHOJANJBR-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)butane Chemical compound CC(C)(C)OOC(C)(CC)OOC(C)(C)C HQOVXPHOJANJBR-UHFFFAOYSA-N 0.000 abstract 1
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 abstract 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 abstract 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 abstract 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 1
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 abstract 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 239000000440 bentonite Substances 0.000 abstract 1
- 229910000278 bentonite Inorganic materials 0.000 abstract 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 abstract 1
- 229940116229 borneol Drugs 0.000 abstract 1
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 229910000019 calcium carbonate Inorganic materials 0.000 abstract 1
- 239000000378 calcium silicate Substances 0.000 abstract 1
- 229910052918 calcium silicate Inorganic materials 0.000 abstract 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical compound OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 abstract 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 abstract 1
- ISQVBYGGNVVVHB-UHFFFAOYSA-N cyclopentylmethanol Chemical compound OCC1CCCC1 ISQVBYGGNVVVHB-UHFFFAOYSA-N 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- 239000011521 glass Substances 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001451 organic peroxides Chemical class 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 abstract 1
- 239000004033 plastic Substances 0.000 abstract 1
- 229920003023 plastic Polymers 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 abstract 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 229910052573 porcelain Inorganic materials 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000377 silicon dioxide Substances 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 abstract 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 239000002562 thickening agent Substances 0.000 abstract 1
- 239000004408 titanium dioxide Substances 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
- 229920006305 unsaturated polyester Polymers 0.000 abstract 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Sealing Material Composition (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Anaerobic adhesives and sealing compounds comprise at least one acrylate or methacrylate ester of a monohydric cycloaliphatic alcohol and 0.1 to 20% by weight, based on the total mixture, of an organic peroxide or hydroperoxide. In a modification, the (meth)acrylate ester may have one or two -CH2- groups in the cycloaliphatic ring replaced by oxygen atoms. Suitable esters include those of cyclopentanol, methylcyclopentanol, cyclohexanol, methylcyclohexanol, methylolcyclopentane, methylolcyclohexane, borneol, tetrahydrofurfuryl alcohol and 1,3-dioxa-2,2-dimethyl-4-methylolcyclopentane. The composition may also include a minor amount, e.g. 2 to 20% by weight, of a copolymerizable compound, e.g. acrylates or methacrylates of other monohydric alcohols such as the butyl and 2-ethyl-hexyl esters, and maleate and fumarate esters an unsaturated polyester may also be included. Other optional components include stabilizers, e.g. hydroquinone, di-t-butylhydroquinone and quinone accelerators for use with the peroxy-compounds, e.g. tertiary amines and mercaptans thickeners, e.g. polymethyl or polyethyl methacrylate plasticizers dyestuffs fillers, e.g. silica, calcium silicate, bentonite, calcium carbonate and titanium dioxide. Suitable peroxy compounds include t-butyl, cumene, methyl ethyl ketone and diisopropylbenzene hydroperoxides, and methyl ethyl ketone peroxide, t-butylperbenzoate and 2,2-bis-(t-butylperoxy)-butane. The compositions are suitable for bonding together various surfaces, e.g. glass, plastics, porcelain and metals the surfaces may be pretreated with metal salt accelerators for the anaerobic composition, e.g. copper or cobalt naphthenate. Curing can be accelerated by heating.ALSO:Tetrahydrofurfuryl methacrylate is prepared by heating methyl methacrylate and tetra-hydrofurfuryl alcohol in the presence of hydroquinone (polymerization inhibitor) and p-toluenesulphonic acid, the methanol of reaction being removed by distillation as an azeotropic mixture with methyl methacrylate. The methacrylate esters of cyclohexanol and 1,3-dioxa-2,2-dimethyl-4 -methylolcyclopentane are prepared in a similar manner.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEH0057990 | 1965-12-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES334593A1 true ES334593A1 (en) | 1968-03-01 |
Family
ID=7159972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES334593A Expired ES334593A1 (en) | 1965-12-17 | 1966-12-16 | Improvements in or relating to adhesives or sealing compounds |
Country Status (10)
| Country | Link |
|---|---|
| AT (1) | AT271679B (en) |
| BE (1) | BE691350A (en) |
| CH (1) | CH481196A (en) |
| DE (1) | DE1594035B2 (en) |
| DK (1) | DK118680B (en) |
| ES (1) | ES334593A1 (en) |
| FR (1) | FR1505098A (en) |
| GB (1) | GB1106449A (en) |
| NL (1) | NL6616273A (en) |
| SE (1) | SE311411B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1078098A (en) * | 1975-05-20 | 1980-05-20 | Rohm And Haas Company | Radiation curable coatings |
| MX2019008294A (en) * | 2017-01-20 | 2019-09-06 | Henkel IP & Holding GmbH | Anaerobic lubricant sealant. |
-
1965
- 1965-12-17 DE DE19651594035 patent/DE1594035B2/en not_active Withdrawn
-
1966
- 1966-11-18 NL NL6616273A patent/NL6616273A/xx unknown
- 1966-12-15 FR FR87546A patent/FR1505098A/en not_active Expired
- 1966-12-16 SE SE1728066A patent/SE311411B/xx unknown
- 1966-12-16 BE BE691350D patent/BE691350A/xx unknown
- 1966-12-16 GB GB5641466A patent/GB1106449A/en not_active Expired
- 1966-12-16 CH CH1802166A patent/CH481196A/en not_active IP Right Cessation
- 1966-12-16 DK DK653166A patent/DK118680B/en unknown
- 1966-12-16 ES ES334593A patent/ES334593A1/en not_active Expired
- 1966-12-16 AT AT1160466A patent/AT271679B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| AT271679B (en) | 1969-06-10 |
| NL6616273A (en) | 1967-06-19 |
| BE691350A (en) | 1967-06-16 |
| GB1106449A (en) | 1968-03-20 |
| FR1505098A (en) | 1967-12-08 |
| DK118680B (en) | 1970-09-21 |
| CH481196A (en) | 1969-11-15 |
| DE1594035B2 (en) | 1970-11-19 |
| DE1594035A1 (en) | 1969-08-21 |
| SE311411B (en) | 1969-06-09 |
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