WO1998038195B1 - PHOTOACTIVATABLE NITROGEN-CONTAINING BASES BASED ON α-AMMONIUM KETONES, IMINIUM KETONES OR AMIDINIUM KETONES AND ARYL BORATES - Google Patents
PHOTOACTIVATABLE NITROGEN-CONTAINING BASES BASED ON α-AMMONIUM KETONES, IMINIUM KETONES OR AMIDINIUM KETONES AND ARYL BORATESInfo
- Publication number
- WO1998038195B1 WO1998038195B1 PCT/EP1998/000846 EP9800846W WO9838195B1 WO 1998038195 B1 WO1998038195 B1 WO 1998038195B1 EP 9800846 W EP9800846 W EP 9800846W WO 9838195 B1 WO9838195 B1 WO 9838195B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compound
- component system
- ketones
- component
- polyacrylate
- Prior art date
Links
- 150000002576 ketones Chemical class 0.000 title abstract 4
- 101700018994 ARYL Proteins 0.000 title 1
- 150000001642 boronic acid derivatives Chemical class 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract 14
- 238000000034 method Methods 0.000 claims abstract 5
- -1 amidinium ketones Chemical class 0.000 claims abstract 3
- 238000006555 catalytic reaction Methods 0.000 claims abstract 3
- 238000002360 preparation method Methods 0.000 claims abstract 3
- 239000003211 photoinitiator Substances 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 12
- 229920000058 polyacrylate Polymers 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 229920001228 Polyisocyanate Polymers 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 239000005056 polyisocyanate Substances 0.000 claims 5
- 125000001931 aliphatic group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 229920000647 polyepoxide Polymers 0.000 claims 4
- 150000008064 anhydrides Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 150000002894 organic compounds Chemical class 0.000 claims 3
- 229920000728 polyester Polymers 0.000 claims 3
- 239000004925 Acrylic resin Substances 0.000 claims 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims 2
- 238000007259 addition reaction Methods 0.000 claims 2
- 150000001728 carbonyl compounds Chemical class 0.000 claims 2
- 125000003700 epoxy group Chemical group 0.000 claims 2
- 239000003822 epoxy resin Substances 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 150000002513 isocyanates Chemical class 0.000 claims 2
- 150000004658 ketimines Chemical class 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- LSWYGACWGAICNM-UHFFFAOYSA-N 2-(prop-2-enoxymethyl)oxirane Chemical compound C=CCOCC1CO1 LSWYGACWGAICNM-UHFFFAOYSA-N 0.000 claims 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 claims 1
- 150000001251 acridines Chemical class 0.000 claims 1
- 125000005466 alkylenyl group Chemical group 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 238000000465 moulding Methods 0.000 claims 1
- 150000002829 nitrogen Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000011368 organic material Substances 0.000 claims 1
- 150000004893 oxazines Chemical class 0.000 claims 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims 1
- 150000002988 phenazines Chemical class 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 125000001725 pyrenyl group Chemical group 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 231100000489 sensitizer Toxicity 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract 2
- 239000011780 sodium chloride Substances 0.000 abstract 2
- 150000001409 amidines Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000002466 imines Chemical class 0.000 abstract 1
Abstract
This invention relates to α-ammonium ketones, iminium ketones or amidinium ketones in the form of their tetraaryl- or triarylalkylborate salts which can be photochemically converted into amines, imines or amidines as well as to a process for their preparation. This invention also relates to base-polymerisable or cross-linkable compositions comprising these α-ammonium ketones, iminium ketones or amidinium ketones in the form of their tetra- or triarylalkylborate salts, to a process for carrying out photochemically induced, base-catalysed reactions as well as to their use as photoinitiators for base-catalysed reactions.
Claims
54
AMENDED CLAIMS
[received by the International Bureau on 19 August 1998 (19.08.98); original claim 1 amended; remaining claims unchanged (4 pages)]
X is Cj-C.oalkylene, C -C2oalkylene which is interrupted by -O-, -S- or NR8, or X is
(a) R , R3 and R4 are not simultaneously methyl; and
(b) R2, R3 and R together are no
2. A compound according to claim 1 , wherein R- is phenyl, naphthyl, pyrenyl, thioxanthyl or penothiazinyl, which radicals are unsubstituted or mono- or polysubstituted by C C18alkyl, C C18haloalkyl, NR6R7 , CN, NO2) SR8 or OR8.
3. A compound according to claim 1 , wherein R , R3 and R4 are each independently of one another hydrogen, C C18alkyl, or R2 and R3, and/or R4 and R3 form each independently of one another a C2-C12alkylene bridge; or
R2, R3, R ) together with the linking nitrogen, are a group of the structural formulae (a), (b), (c), (d), (e), (f), (g), (h) or a phosphazene base of the P P2 or P <t/4> type.
4. A compound according to claim 1 , wherein R2, R3 and R4 are each independently of one another C C18alkyl, or
R2> R3, R , together with the nitrogen atom, are a group of the structural formula (a), (b), (c),- (d) or (e).
AMENDED SHEET AfffiCL 55
5. A compound according to claim 1 , wherein R12, R13, R╬╣4 are phenyl, biphenyl, naphthyl, anthracyl or penanthryl, which radicals are unsubstituted or mono- or polysubstituted by C C18alkyl, CrC18haloalkyl, NO2, OH, CN, OR8, or halogen, and
R15 is CrC18alkyl or phenyl which is unsubstituted or mono- or polysubstituted by C C18alkyl, C C18haloalkyl, NO2, OH, CN, OR8 or halogen.
6. A process for the preparation of a compound of formula I, which comprises reacting in a first step a nitrogenous base of formula II
NR2R3R4 (II) with an ╬▒- halogen ketone of formula III
Halogen
CH R, (HI)
R O
to a compound of formula IV
R '33
R I + N ΓÇö R,
-CH Halogen (IV)
R; ,R, m
and, in a second step, reacting the compound of formula IV with a compound of formula V
7. A composition, which comprises
A) at least one compound of formula (I), and B) at least one organic compound which is capable of a base-catalysed addition reaction or substitution reaction.
8. A composition according to claim 7, wherein component B) is an anionically polymerisable or crosslinkable organic material.
9. A composition according to claim 7, wherein component B) is one of the following systems: a) an acrylate copolymer having alkoxysilane or alkoxysiloxane side groups, b) a two-component system comprising a hydroxyl group-containing polyacrylate and/or polyester and an aliphatic or aromatic polyisocyanate, c) a two-component system comprising a functional polyacrylate and a polyepoxide, where the polyacrylate contains carboxyl or anhydride groups, d) a two-component system comprising a fluorine-modified or silicone-modified hydroxyl group-containing polyacrylate or polyester and an aliphatic or aromatic polyisocyanate, e) a two-component system comprising a (poly)ketimine and an aliphatic or aromatic polyisocyanate, f) a two-component system comprising a (poly)ketimine and an unsaturated acrylate resin or an acetoacetate resin or methyl ╬▒-acrylamidomethylglycolate, h) a two-component system comprising a (poly)oxazolidine and a polyacrylate containing anhydride groups, or an unsaturated acrylate resin or a polyisocyanate, i) a two-component system comprising an epoxy group-containing polyacrylate and a carboxyl group-containing polyacrylate,
I) a polymer based on allyl glycidyl ether, m) a two-component system comprising a (poly)alcohol and a (poly)isocyanate, n) a two-component system comprising an ╬▒,╬▓-ethylenically unsaturated carbonyl compound and a compound which contains activated CH2 groups.
10. A composition according to claim 7, wherein component B) is one of the following systems: b) a two-component system comprising a hydroxyl group-containing polyacrylate and/or polyester and an aliphatic or aromatic polyisocyanate, c) a two-component system comprising a functional polyacrylate and a polyepoxide, where" the polyacrylate contains carboxyl or anhydride groups, 57
i) a two-component system comprising an epoxy group-containing polyacrylate and a carboxyl group-containing polyacrylate, m) a two-component system comprising a (poly)alcohol and a (poly)isocyanate, and n) a two-component system comprising an ,╬▓-ethylenically unsaturated carbonyl compound and a compound which contains activated CH2 groups.
11. A composition according to claim 7, wherein component B is an epoxy resin or a mixture of different epoxy resins.
12. A composition according to claim 7, wherein component A) is present in an amount of 0.01 to 10 % by weight, based on component B).
13. A composition according to claim 7, which additionally comprises a sensitiser selected from the group consisting of thioxanthones, oxazines, acridines, phenazines and rhodamines.
14. A process for carrying out base-catalysed reactions, which comprises exposing a composition according to claim 7 with light having a wavelength in the range from 200 nm to
650 nm.
15. A process according to claim 14, which comprises heating the composition before or after the exposure to light.
16. Use of an organic compound according to claim 1 as photoinitiator for photochemically induced base-catalysed addition reactions or substitution reactions.
17. Use of an organic compound according to claim 1 for the preparation of coatings, moulding compositions or photostructured layers.
18. A coated substrate, which is coated on at least one surface with a composition as claimed in claim 7.
19. A polymerised or crosslinked composition according to claim 7.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE69839020T DE69839020T2 (en) | 1997-02-26 | 1998-02-14 | Photoactivatable nitrogenous bases based on ALPHA ammonium, iminium or amidinium ketones and arylborates |
| CA002281860A CA2281860C (en) | 1997-02-26 | 1998-02-14 | Photoactivatable nitrogen-containing bases based on .alpha.-ammonium ketones, iminium ketones or amidinium ketones and aryl borates |
| JP53724898A JP4155603B2 (en) | 1997-02-26 | 1998-02-14 | Nitrogen-containing bases that can be activated by light, based on α-ammonium ketones, iminium ketones or amidinium ketones and aryl borates |
| BRPI9807790-2A BR9807790B1 (en) | 1997-02-26 | 1998-02-14 | nitrogen-containing photoactivated bases based on alpha-ammonium ketones, imine ketones or amidium ketones and aryl borates, their composition and process for performing base catalyzed reactions. |
| AU64972/98A AU726375B2 (en) | 1997-02-26 | 1998-02-14 | Photoactivatable nitrogen-containing bases based on alpha-ammonium ketones, iminium ketones or amidinium ketones and aryl borates |
| KR1019997007769A KR100542419B1 (en) | 1997-02-26 | 1998-02-14 | Photoactivatable nitrogen-containing bases based on ?-ammonium ketones, iminium ketones or amidinium ketones and aryl borates, process for the preparation thereof, and composition comprising the same |
| EP98910669A EP1032576B1 (en) | 1997-02-26 | 1998-02-14 | Photoactivatable nitrogen-containing bases based on alpha-ammonium ketones, iminium ketones or amidinium ketones and aryl borates |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH444/97 | 1997-02-26 | ||
| CH44497 | 1997-02-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1998038195A1 WO1998038195A1 (en) | 1998-09-03 |
| WO1998038195B1 true WO1998038195B1 (en) | 1998-10-22 |
Family
ID=4187172
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1998/000846 WO1998038195A1 (en) | 1997-02-26 | 1998-02-14 | PHOTOACTIVATABLE NITROGEN-CONTAINING BASES BASED ON α-AMMONIUM KETONES, IMINIUM KETONES OR AMIDINIUM KETONES AND ARYL BORATES |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP1032576B1 (en) |
| JP (1) | JP4155603B2 (en) |
| KR (1) | KR100542419B1 (en) |
| AU (1) | AU726375B2 (en) |
| BR (1) | BR9807790B1 (en) |
| CA (1) | CA2281860C (en) |
| DE (1) | DE69839020T2 (en) |
| TW (1) | TW425399B (en) |
| WO (1) | WO1998038195A1 (en) |
| ZA (1) | ZA981556B (en) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60219812T8 (en) | 2001-10-17 | 2008-05-21 | Ciba Specialty Chemicals Holding Inc. | PHOTOACTIVABLE NITROGEN BOTTOMS |
| WO2005014696A1 (en) * | 2003-08-06 | 2005-02-17 | Mitsubishi Gas Chemical Company, Inc. | Photocurable composition and coating composition |
| RU2381835C2 (en) * | 2004-07-21 | 2010-02-20 | Циба Спешиалти Кемикэлз Холдинг Инк. | Photoactivation method and use of catalyst through inverted two-stage procedure |
| KR101514093B1 (en) | 2007-04-03 | 2015-04-21 | 바스프 에스이 | Photoactivable nitrogen bases |
| EP2270114B1 (en) * | 2008-03-31 | 2014-07-09 | San-Apro Limited | Photobase generator |
| TW201106101A (en) * | 2009-06-01 | 2011-02-16 | Fujifilm Electronic Materials | Chemically amplified positive photoresist composition |
| EP2588537A1 (en) * | 2010-06-30 | 2013-05-08 | 3M Innovative Properties Company | Curable-on-demand composition comprising dual reactive silane functionality |
| EP2797985B1 (en) * | 2011-12-29 | 2015-09-23 | 3M Innovative Properties Company | Curable-on-demand polysiloxane coating composition |
| JP5912946B2 (en) * | 2012-01-11 | 2016-04-27 | 株式会社Adeka | Photosensitive resin composition |
| WO2013141014A1 (en) | 2012-03-22 | 2013-09-26 | 株式会社Adeka | Novel compound and photosensitive resin composition |
| JP5997041B2 (en) * | 2012-12-26 | 2016-09-21 | 東京応化工業株式会社 | Photosensitive resin composition |
| JP5978138B2 (en) * | 2013-01-22 | 2016-08-24 | 株式会社Adeka | Novel compound and photosensitive resin composition |
| KR102305831B1 (en) | 2013-07-18 | 2021-09-27 | 세메다인 가부시키 가이샤 | Photocurable composition, cured product and producing method thereof, and related products and manufacturing method thereof |
| EP3081612B1 (en) | 2013-12-13 | 2018-11-14 | Cemedine Co., Ltd. | Photocurable composition having adhesive properties |
| JP6167089B2 (en) * | 2014-03-27 | 2017-07-19 | 富士フイルム株式会社 | Photosensitive resin composition, cured film, method for producing cured film, and semiconductor device |
| CA2984033C (en) | 2015-04-29 | 2023-08-15 | Bsn Medical Gmbh | Medical bathing equipment |
| WO2016174043A1 (en) | 2015-04-29 | 2016-11-03 | Bsn Medical Gmbh | Multi-step process for no production |
| EP3395800B1 (en) | 2017-04-26 | 2021-11-03 | Henkel AG & Co. KGaA | Heterocyclic quaternary nitrogen compounds comprising a polymeric substituent and their use as a photolatent catalyst in curable compositions |
| JP2021529840A (en) | 2018-04-26 | 2021-11-04 | ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェンＨｅｎｋｅｌ ＡＧ ＆ Ｃｏ． ＫＧａＡ | A quaternary nitrogen compound for use as a latent catalyst in curable compositions. |
| JP7384418B2 (en) | 2018-08-28 | 2023-11-21 | 学校法人東京理科大学 | Curable composition, cured product, and method for producing cured product |
| CN115151591B (en) * | 2020-06-26 | 2024-03-01 | 株式会社艾迪科 | Composition, cured product, and method for producing cured product |
| WO2021261497A1 (en) * | 2020-06-26 | 2021-12-30 | 株式会社Adeka | Compound, initiator, composition, cured product and method for producing cured product |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2571113B2 (en) * | 1988-12-29 | 1997-01-16 | 富士写真フイルム株式会社 | Photopolymerizable composition |
| JP3293258B2 (en) * | 1993-09-01 | 2002-06-17 | 東洋インキ製造株式会社 | Pyridinium complexes and their uses |
| JP3412199B2 (en) * | 1993-09-01 | 2003-06-03 | 東洋インキ製造株式会社 | Method for producing polymerizable composition and cured product thereof |
| JPH09263063A (en) * | 1996-01-22 | 1997-10-07 | Toyo Ink Mfg Co Ltd | Composition for forming energy beam-sensitive line image, image forming medium using the same and image forming method |
| JPH09227854A (en) * | 1996-02-26 | 1997-09-02 | Toyo Ink Mfg Co Ltd | Actinic-radiation-sensitive acid generator, actinic-radiation-sensitive acid generator composition, curable composition and cured product thereof |
| JPH09241614A (en) * | 1996-03-04 | 1997-09-16 | Toyo Ink Mfg Co Ltd | Energy ray-sensitive acid-generating agent, energy ray-sensitive acid-generating agent composition, curable composition and its cured product |
| JPH09316117A (en) * | 1996-06-03 | 1997-12-09 | Toyo Ink Mfg Co Ltd | Polymerizable composition and cured substance therefrom |
| JPH09328507A (en) * | 1996-06-10 | 1997-12-22 | Toyo Ink Mfg Co Ltd | Polymerization initiator, polymerizable composition and cured material obtained therefrom |
| JPH101508A (en) * | 1996-06-17 | 1998-01-06 | Toyo Ink Mfg Co Ltd | Active ray sensitive acid generating agent composition, responsive composition, and image recording composition |
| JPH107709A (en) * | 1996-06-24 | 1998-01-13 | Toyo Ink Mfg Co Ltd | Energy ray-sensitive active composition, and responsive compositions and image-forming composition using the same |
-
1998
- 1998-02-14 AU AU64972/98A patent/AU726375B2/en not_active Ceased
- 1998-02-14 CA CA002281860A patent/CA2281860C/en not_active Expired - Fee Related
- 1998-02-14 BR BRPI9807790-2A patent/BR9807790B1/en not_active IP Right Cessation
- 1998-02-14 WO PCT/EP1998/000846 patent/WO1998038195A1/en active IP Right Grant
- 1998-02-14 JP JP53724898A patent/JP4155603B2/en not_active Expired - Fee Related
- 1998-02-14 DE DE69839020T patent/DE69839020T2/en not_active Expired - Lifetime
- 1998-02-14 EP EP98910669A patent/EP1032576B1/en not_active Expired - Lifetime
- 1998-02-14 KR KR1019997007769A patent/KR100542419B1/en not_active IP Right Cessation
- 1998-02-25 ZA ZA981556A patent/ZA981556B/en unknown
- 1998-03-10 TW TW087103457A patent/TW425399B/en not_active IP Right Cessation
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