GB1445814A - Photocurable lacquer composition - Google Patents
Photocurable lacquer compositionInfo
- Publication number
- GB1445814A GB1445814A GB169274A GB169274A GB1445814A GB 1445814 A GB1445814 A GB 1445814A GB 169274 A GB169274 A GB 169274A GB 169274 A GB169274 A GB 169274A GB 1445814 A GB1445814 A GB 1445814A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- substituted
- valence
- group
- general formula
- 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
- 239000000203 mixture Substances 0.000 title abstract 5
- 239000004922 lacquer Substances 0.000 title abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 7
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 239000004014 plasticizer Substances 0.000 abstract 3
- 229920006295 polythiol Polymers 0.000 abstract 3
- 229920006395 saturated elastomer Polymers 0.000 abstract 3
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 abstract 2
- 125000003118 aryl group Chemical class 0.000 abstract 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 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 abstract 2
- 239000006185 dispersion Substances 0.000 abstract 2
- 239000012442 inert solvent Substances 0.000 abstract 2
- 229920000728 polyester Polymers 0.000 abstract 2
- 150000007519 polyprotic acids Polymers 0.000 abstract 2
- QOYUNYZPUQSHDY-UHFFFAOYSA-N (1-chloro-1-fluoro-2-nitramido-2-oxoethyl) acetate Chemical compound CC(=O)OC(F)(Cl)C(=O)N[N+]([O-])=O QOYUNYZPUQSHDY-UHFFFAOYSA-N 0.000 abstract 1
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 abstract 1
- SCZZNWQQCGSWSZ-UHFFFAOYSA-N 1-prop-2-enoxy-4-[2-(4-prop-2-enoxyphenyl)propan-2-yl]benzene Chemical compound C=1C=C(OCC=C)C=CC=1C(C)(C)C1=CC=C(OCC=C)C=C1 SCZZNWQQCGSWSZ-UHFFFAOYSA-N 0.000 abstract 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 abstract 1
- LZDXRPVSAKWYDH-UHFFFAOYSA-N 2-ethyl-2-(prop-2-enoxymethyl)propane-1,3-diol Chemical compound CCC(CO)(CO)COCC=C LZDXRPVSAKWYDH-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002202 Polyethylene glycol Substances 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- YLTDNYQTDYMOBH-UHFFFAOYSA-N bis(prop-2-enyl) 2-hydroxybutanedioate Chemical compound C=CCOC(=O)C(O)CC(=O)OCC=C YLTDNYQTDYMOBH-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000005442 diisocyanate group Chemical group 0.000 abstract 1
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 abstract 1
- 238000000016 photochemical curing Methods 0.000 abstract 1
- 150000004291 polyenes Chemical class 0.000 abstract 1
- 229920001223 polyethylene glycol Polymers 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 230000005855 radiation Effects 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000005415 substituted alkoxy group Chemical group 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- 150000005846 sugar alcohols Polymers 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- 150000003573 thiols Chemical class 0.000 abstract 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/04—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters
- C08F299/0407—Processes of polymerisation
- C08F299/0421—Polymerisation initiated by wave energy or particle radiation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
1445814 Photocurable lacquers W R GRACE & CO 14 Jan 1974 01692/74 Heading C3P [Also in Division C2] A photocurable lacquer composition comprises (a) a polythiol component which contains at least two -SH groups per molecule and has a viscosity range of essentially 0 up to 20 million centipoises (cps) at 70‹ C., as measured by a Brookfield Viscometer, either alone or when in the presence of an inert solvent, aqueous dispersion or plasticizer, (b) a polyene component which contains at least one of N, O and a six-membered carbon containing ring and is selected from triallylisocyanurate, bisphenol A diallyl ether, 2,4,6-tris(allyloxy)s-triazine, the diadduct of diallylamine and bisphenol A 4,4<SP>1</SP>- diglycidylether, and the diadduct of one or more first members selected from the ene-ol group of allyl alcohol, diallyl malate and trimethylolpropane allyl ether with a second member selected from the cyclic C 6 diisocyanate group of toluene diisocyanate, 3,3<SP>1</SP>-dimethyl- 4,4<SP>1</SP>-biphenylene diisocyanate, 3-isocyanatomethyl - 3,5,5 - trimethylcyclohexylisocyanate and 4,4<SP>1</SP> - methylenebis - (cyclohexylisocyanate) the mole ratio of ene to thiol being from 0À2 : 1 to 5 : 1, and the polythiol having a Brookfield viscosity of 0 to 20,000,000 centipoises at 70‹ C., either alone, or when in the presence of an inert solvent, aqueous dispersion or plasticizer (c) from 1-50 parts by weight, per 100 parts by weight of the polyene-polythiol combination of either (i) a normally solid, solvent soluble polyester component having a molecular weight of 500-100,000 prepared by reacting either (I) a polybasic acid of general formula where R 4 is a saturated or unsaturated hydrocarbyl group having a valence of x and containing 2-21 carbon atoms, x being at least 2 or (II) a polybasic acid anhydride of general formula where z is 0 or 1, Z is a saturated or unsaturated hydrocarbyl group having from 2-12 carbon atoms and a valence of 2 with z is 0 and a valence of 3 when z is 1 with (III) a polyhydric alcohol of general formula where R 5 is a saturated or unsaturated hydrocarbyl or oxyhydrocarbyl group having a valence of y and containing 2-30 carbon atoms, y being at least 2 or (ii) a normally liquid plasticizer component selected from polyethylene glycol having a molecular weight of up to about 400, dioctyl phosphate and dibutyl phthalate, (d) from 0À0005-50 per cent by weight of the composition of a photo-curing rate accelerator (those preferred being compounds in which the carbonyl group of an aldehyde or ketone is directly attached to an aromatic nucleus). The polyester component may be a polyester-polyene having a molecular weight of 100-20,000 and a viscosity of 0-20,000,000 cps at 70‹ C., as measured by a Brookfield viscometer and having at least two unsaturated carbon-tocarbon bonds disposed at terminal or near terminal positions on the main chain of the molecule or pendant therefrom prepared by capping the product of (I) or (II) with (III) with a compound of general formula wherein R 6 is a hydrocarbyl group of free or remotely internal ("remotely internal" being defined as more than 8 carbon atoms from the moiety) non-aromatic ene and yne functionality and having a valence of q+s and from 2-10 carbon atoms; p is 0 or 1; q is an integer of 1- 10; s is an integer of 1-10; and R 7 is selected from wherein g is 0 or an integer of 1-9; h is 0 or 1; and the various R radicals are selected from hydrogen, fluorine, chlorine, furyl, thienyl, pyridyl, phenyl and substituted phenyl, benzyl and substituted benzyl, alkyl and substituted alkyl, alkoxy and substituted alkoxy, and cycloalkyl and substituted cycloalkyl, the substituents on the substituted radicals being selected from nitro, chloro, fluoro, acetoxy, acetamide, phenyl, benzyl, alkyl, alkoxy, and cycloalkyl wherein the alkyl and alkoxy groups contain 7-9 carbon atoms and the cycloalkyl groups contain 3-8 carbon atoms. The compositions are used to coat a substrate, and the applied compositions are cured using actinic radiation (especially ultraviolet of 100- 4000 Šngstr÷ms) the thickness of the coating being preferably 0À0025-0À05 mm.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB169274A GB1445814A (en) | 1974-01-14 | 1974-01-14 | Photocurable lacquer composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB169274A GB1445814A (en) | 1974-01-14 | 1974-01-14 | Photocurable lacquer composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1445814A true GB1445814A (en) | 1976-08-11 |
Family
ID=9726358
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB169274A Expired GB1445814A (en) | 1974-01-14 | 1974-01-14 | Photocurable lacquer composition |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1445814A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0020548A4 (en) * | 1978-10-19 | 1981-02-12 | Gen Electric | Photocurable coating composition. |
| US4435497A (en) | 1981-06-19 | 1984-03-06 | Ciba-Geigy Corporation | Carboxyl-containing compositions and their polymerization |
-
1974
- 1974-01-14 GB GB169274A patent/GB1445814A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0020548A4 (en) * | 1978-10-19 | 1981-02-12 | Gen Electric | Photocurable coating composition. |
| US4435497A (en) | 1981-06-19 | 1984-03-06 | Ciba-Geigy Corporation | Carboxyl-containing compositions and their polymerization |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |