GB2447933A - Cyanoacrylate monomer for forming an adhesive polymer - Google Patents
Cyanoacrylate monomer for forming an adhesive polymer Download PDFInfo
- Publication number
- GB2447933A GB2447933A GB0705977A GB0705977A GB2447933A GB 2447933 A GB2447933 A GB 2447933A GB 0705977 A GB0705977 A GB 0705977A GB 0705977 A GB0705977 A GB 0705977A GB 2447933 A GB2447933 A GB 2447933A
- Authority
- GB
- United Kingdom
- Prior art keywords
- monomer
- cyclohexyl
- methyl
- ethyl
- side chain
- 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.)
- Withdrawn
Links
- 239000000178 monomer Substances 0.000 title claims abstract description 27
- 229920001651 Cyanoacrylate Polymers 0.000 title claims abstract description 12
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 239000002998 adhesive polymer Substances 0.000 title claims abstract description 4
- -1 cyclodecyl Chemical group 0.000 claims abstract description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- ILRMPAUJTPZAIQ-UHFFFAOYSA-N cyclohexyl 2-cyanoprop-2-enoate Chemical group N#CC(=C)C(=O)OC1CCCCC1 ILRMPAUJTPZAIQ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 3
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims abstract description 3
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims abstract description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 229920000642 polymer Polymers 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract description 2
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 description 3
- 229940053009 ethyl cyanoacrylate Drugs 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 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
- C08F122/00—Homopolymers 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
- C08F122/30—Nitriles
- C08F122/32—Alpha-cyano-acrylic acid; Esters thereof
-
- 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
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
A cyanoacrylate monomer, containing a side chain of at least three carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl or cyclodecyl, cyclopropyl methyl, 1-cyclopropyl ethyl, cyclobutyl methyl, cyclopentyl methyl, 1-cyclopentyl ethyl, 3-pentyl-1-propyl, cyclohexyl methyl, 1-cyclohexyl ethyl, 2-cyclohexyl ethyl, 3-cyclohexyl-1-propyl, 3-cyclohexyl-1-propyl or 4-cyclohexyl-1-butyl. The monomer is preferably cyclohexyl cyanoacrylate monomer. The monomer is used for forming an adhesive polymer suitable for use in an environment containing water or water vapour.
Description
Cyanoacrylate Monomer The present invention relates to a cyanoacrylate
monomer and to polymers formed therefrom It is well known that that the polymeric adhesives formed from conventional cyanoacrylate monomers e.g. methyl and ethyl cyanoacrylate monomers are not generally suitable for use in a water-containing wet, damp or moist environment. Such environments are known to adversely affect the adhesive and the adhesive bond.
Thus cyanoacrylate polymeric compounds so formed are not used for reliable, durable or permanent repairs in an environment which is likely to contain for example water vapour at some stage such as the outdoors, marine environments, medical and cosmetic applications where a permanent or durable fixture is needed.
**** These compounds are unsuitable for use in the environments described because in * * damp, wet or moist conditions in particular the cyanoacrylate polymer which forms during curing of the adhesive monomer is attacked chemically by the water and S ultimately degrades causing the bond so formed to fail. The bond can degrade by as * much as 55% in a water-borne environment over a period of 80 days at 40C, although *: ::: the exact figure is somewhat dependent on the nature of the substrate. ** S * S S
* However we have surprisingly found that certain selected cyanoacrylate polymers formed from suitable monomers are resistant to attack by the water containing environments defined above.
Therefore in accordance with the present invention, we provide a cyanoacrylate monomer for forming an adhesive polymer suitable for use in an environment containing water or water vapour in which the cyanoacrylate monomer has a side chain of at least three carbon atoms.
Preferably the side chain is selected from a cycloalkyl group such as, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl.
Suitably the side chain is selected from a cycloalkyl alkyl group, cyclopropyl methyl, I -cyclopropyl ethyl, cyclobutyl methyl, cyclopentyl methyl, I -cyclopentyl ethyl, 3- pentyl-l-propyl, cyclohexyl methyl, 1-cyclohexyl ethyl, 2-cyclohexyl ethyl, 3-cyclohexyl-I -propyl and 4-cyclohexyl-I -butyl.
Conveniently the side chain is selected from unsaturated cycloalkyl groups such as cyclohexen-1-methyl, 2-cyclohexen-1-methyl.
The side chain may be selected from cycloalkoxy alkyl groups such as 2-(cyclohexyloxy) ethyl.
Preferably the side chain is selected from aromatic groups such as phenyl methyl and phenyl. S... * S
We have found that a polymer formed from a cyclohexyl cyanoacrylate monomer is a * particularly suitable adhesive for use in a water-containing atmosphere. ***
:::: An embodiment of the invention will now be particularly described with reference to *. the following example:-Shear strength tests were made on cleaned steel test pieces bonded with either ethyl cyanoacrylate or cyclohexyl cyanoacrylate. Samples were conditioned at 40 C either in a dry or wet (immersed in tap water) environment for periods up to 80 days. The samples bonded with ethyl cyanoacrylate maintained some 75% of their strength in dry conditions whereas in wet conditions the samples only retained some 45% of their strength. Samples bonded with cyclohexyl cyanoacrylate performed much better. In dry conditions where 83% of strength was retained and in wet conditions some 87% of strength was retained.
--
Claims (10)
- Claims I. A cyanoacrylate monomer for forming an adhesive polymersuitable for use in an environment containing water or water vapour, the cyanoacrylate monomer containing a side chain of at least three carbon atoms.
- 2. A monomer as claimed in claim I in which the side chain is selected from a cycloalkyl group such as cyclopropyl, cyclobutyl, cyclopenlyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl.
- 3. A monomer as claimed in claim I or claim 2 in which the side chain is selected from a cycloalkyl alkyl group, cyclopropyl methyl, I -cyclopropyl ethyl, cyclobutyl methyl, cyclopentyl methyl, 1-cyclopentyl ethyl, 3-pentyl-l-propyl, cyclohexyl methyl, 1 -cyclohexyl ethyl, 2-cyclohexyl ethyl, 3-cyclohexyl-I -propyl and 4-cyclohexyl-1 -butyl. * S S...
- 4. A monomer as claimed in any of claims 1 to 3 in which the side chain is selected from unsaturated cycloalkyl groups such as cyclohexen-1-methyl and 2-cyclohexen-l-S..* methyl. * * . S
- 5. A monomer as claimed in any of claims Ito 4 in which the side chain is selected from cycloalkoxy alkyl groups such as 2-(cyclohexyloxyl) ethyl.
- 6. A monomer as claimed in any of claims I to 5 in which the side chain is selected from aromatic groups such as phenyl methyl and phenyl.
- 7. A monomer as claimed in any of the preceding claims in which the monomer is a cyclohexyl cyanoacrylate monomer.
- 8. A monomer as claimed in any of claims I to 7 in which the environment is wet, damp or moist.
- 9. A monomer substantially as hereinbefore described with reference to the example.
- 10. A polymer when formed from a monomer as claimed in any of the preceding claims. * * * S.. * * S S... * S. * SS I..S 5*55 * SS S. * S. *S S *5
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0705977A GB2447933A (en) | 2007-03-27 | 2007-03-27 | Cyanoacrylate monomer for forming an adhesive polymer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0705977A GB2447933A (en) | 2007-03-27 | 2007-03-27 | Cyanoacrylate monomer for forming an adhesive polymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB0705977D0 GB0705977D0 (en) | 2007-05-09 |
| GB2447933A true GB2447933A (en) | 2008-10-01 |
Family
ID=38050360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB0705977A Withdrawn GB2447933A (en) | 2007-03-27 | 2007-03-27 | Cyanoacrylate monomer for forming an adhesive polymer |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2447933A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011029777A1 (en) | 2009-09-11 | 2011-03-17 | Basf Se | Methods for producing coated polymer fibers |
| US8940744B2 (en) | 2012-09-10 | 2015-01-27 | Principia Biopharma Inc. | Pyrazolopyrimidine compounds as kinase inhibitors |
| US8946241B2 (en) | 2013-04-09 | 2015-02-03 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
| US8962831B2 (en) | 2011-05-17 | 2015-02-24 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
| US9376438B2 (en) | 2011-05-17 | 2016-06-28 | Principia Biopharma, Inc. | Pyrazolopyrimidine derivatives as tyrosine kinase inhibitors |
| US10092569B2 (en) | 2014-02-21 | 2018-10-09 | Principia Biopharma Inc. | Salts and solid form of a BTK inhibitor |
| US10485797B2 (en) | 2014-12-18 | 2019-11-26 | Principia Biopharma Inc. | Treatment of pemphigus |
| US11155544B2 (en) | 2015-06-24 | 2021-10-26 | Principia Biopharma Inc. | Heterocycle comprising tyrosine kinase inhibitors |
| US11872229B2 (en) | 2016-06-29 | 2024-01-16 | Principia Biopharma Inc. | Modified release formulations of 2-[3-[4-amino-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile |
| US12178818B2 (en) | 2019-10-14 | 2024-12-31 | Principia Biopharma Inc. | Methods for treating immune thrombocytopenia by administering (R)-2-[3-[4-amino-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1539421A (en) * | 1966-10-10 | 1968-09-13 | Adhesive paste usable underwater | |
| GB1354204A (en) * | 1970-06-11 | 1974-06-05 | Johnson & Johnson | Adhesive composition |
| GB1392400A (en) * | 1972-02-18 | 1975-04-30 | Denki Kagaku Kogyo Kk | Stabilized alpha-cyanoacrylate monomers |
| GB2078763A (en) * | 1980-06-04 | 1982-01-13 | Takiron Co | A Bonding Method Using an alpha - cyanoacrylate Adhesive |
| JPS61148276A (en) * | 1984-12-21 | 1986-07-05 | Toagosei Chem Ind Co Ltd | Composition for acrylic resin |
| JPH04272980A (en) * | 1991-02-27 | 1992-09-29 | Toagosei Chem Ind Co Ltd | Adhesive composition |
-
2007
- 2007-03-27 GB GB0705977A patent/GB2447933A/en not_active Withdrawn
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1539421A (en) * | 1966-10-10 | 1968-09-13 | Adhesive paste usable underwater | |
| GB1354204A (en) * | 1970-06-11 | 1974-06-05 | Johnson & Johnson | Adhesive composition |
| GB1392400A (en) * | 1972-02-18 | 1975-04-30 | Denki Kagaku Kogyo Kk | Stabilized alpha-cyanoacrylate monomers |
| GB2078763A (en) * | 1980-06-04 | 1982-01-13 | Takiron Co | A Bonding Method Using an alpha - cyanoacrylate Adhesive |
| JPS61148276A (en) * | 1984-12-21 | 1986-07-05 | Toagosei Chem Ind Co Ltd | Composition for acrylic resin |
| JPH04272980A (en) * | 1991-02-27 | 1992-09-29 | Toagosei Chem Ind Co Ltd | Adhesive composition |
Cited By (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011029777A1 (en) | 2009-09-11 | 2011-03-17 | Basf Se | Methods for producing coated polymer fibers |
| US8962831B2 (en) | 2011-05-17 | 2015-02-24 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
| US9376438B2 (en) | 2011-05-17 | 2016-06-28 | Principia Biopharma, Inc. | Pyrazolopyrimidine derivatives as tyrosine kinase inhibitors |
| US10533013B2 (en) | 2012-09-10 | 2020-01-14 | Principia Biopharma Inc. | Substituted pyrazolo[3,4-d]pyrimidines as kinase inhibitors |
| US8940744B2 (en) | 2012-09-10 | 2015-01-27 | Principia Biopharma Inc. | Pyrazolopyrimidine compounds as kinase inhibitors |
| US9266895B2 (en) | 2012-09-10 | 2016-02-23 | Principia Biopharma Inc. | Substituted pyrazolo[3,4-d]pyrimidines as kinase inhibitors |
| US9994576B2 (en) | 2012-09-10 | 2018-06-12 | Principia Biopharma Inc. | Substituted pyrazolo[3,4-d]pyrimidines as kinase inhibitors |
| US11040980B2 (en) | 2012-09-10 | 2021-06-22 | Principia Biopharma Inc. | Substituted pyrazolo[3,4-d]pyrimidines as kinase inhibitors |
| US8946241B2 (en) | 2013-04-09 | 2015-02-03 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
| US8957080B2 (en) | 2013-04-09 | 2015-02-17 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
| US8962635B2 (en) | 2013-04-09 | 2015-02-24 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
| US9090621B2 (en) | 2013-04-09 | 2015-07-28 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
| US10092569B2 (en) | 2014-02-21 | 2018-10-09 | Principia Biopharma Inc. | Salts and solid form of a BTK inhibitor |
| US10828307B2 (en) | 2014-02-21 | 2020-11-10 | Principia Biopharma Inc. | Salts and solid form of a BTK inhibitor |
| US10456403B2 (en) | 2014-02-21 | 2019-10-29 | Principia Biopharma Inc. | Salts and solid form of a BTK inhibitor |
| US11369613B2 (en) | 2014-02-21 | 2022-06-28 | Principia Biopharma Inc. | Salts and solid form of a BTK inhibitor |
| US10485797B2 (en) | 2014-12-18 | 2019-11-26 | Principia Biopharma Inc. | Treatment of pemphigus |
| US10946008B2 (en) | 2014-12-18 | 2021-03-16 | Principia Biopharma Inc. | Treatment of pemphigus |
| US11155544B2 (en) | 2015-06-24 | 2021-10-26 | Principia Biopharma Inc. | Heterocycle comprising tyrosine kinase inhibitors |
| US11872229B2 (en) | 2016-06-29 | 2024-01-16 | Principia Biopharma Inc. | Modified release formulations of 2-[3-[4-amino-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile |
| US12178818B2 (en) | 2019-10-14 | 2024-12-31 | Principia Biopharma Inc. | Methods for treating immune thrombocytopenia by administering (R)-2-[3-[4-amino-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile |
Also Published As
| Publication number | Publication date |
|---|---|
| GB0705977D0 (en) | 2007-05-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |