CH628651A5 - UV radiation-polymerisable mixtures - Google Patents

UV radiation-polymerisable mixtures Download PDF

Info

Publication number: CH628651A5
Authority: CH; Switzerland
Prior art keywords: parts; mixtures; aromatic; radicals; monoketals
Prior art date: 1976-04-14

Application number

CH443677A

Other languages

German (de)

English (en)

Inventor

Chem Werner Dr Kuesters

Chem Manfred Dr Jacobi

Chem Rolf Dr Osterloh

Original Assignee

Basf Ag

Priority date (The priority date 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 date listed.)

1976-04-14

Filing date

1977-04-07

Publication date

1982-03-15

1977-04-07 Application filed by Basf Ag filed Critical Basf Ag

1982-03-15 Publication of CH628651A5 publication Critical patent/CH628651A5/de

Links

239000000203 mixture Substances 0.000 title description 32
150000001875 compounds Chemical class 0.000 description 14
125000003118 aryl group Chemical group 0.000 description 11
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
229940100198 alkylating agent Drugs 0.000 description 7
239000002168 alkylating agent Substances 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
238000004519 manufacturing process Methods 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 6
238000001723 curing Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
-1 3-Methoxibenzil Chemical compound 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
239000000178 monomer Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000004215 Carbon black (E152) Substances 0.000 description 4
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000000654 additive Substances 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
239000004922 lacquer Substances 0.000 description 4
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SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
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QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
150000001649 bromium compounds Chemical class 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000002026 chloroform extract Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000012188 paraffin wax Substances 0.000 description 2
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230000005855 radiation Effects 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
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101150084750 1 gene Proteins 0.000 description 1
ZKERBBAYDZRNID-UHFFFAOYSA-N 1,2-bis(2,4-dimethylphenyl)ethane-1,2-dione Chemical compound CC1=CC(C)=CC=C1C(=O)C(=O)C1=CC=C(C)C=C1C ZKERBBAYDZRNID-UHFFFAOYSA-N 0.000 description 1
PYDAJROJMZJKFS-UHFFFAOYSA-N 1,2-bis(2-methoxyphenyl)ethane-1,2-dione Chemical compound COC1=CC=CC=C1C(=O)C(=O)C1=CC=CC=C1OC PYDAJROJMZJKFS-UHFFFAOYSA-N 0.000 description 1
QGVJJXJRGYQAST-UHFFFAOYSA-N 1,2-bis(2-methylphenyl)ethane-1,2-dione Chemical compound CC1=CC=CC=C1C(=O)C(=O)C1=CC=CC=C1C QGVJJXJRGYQAST-UHFFFAOYSA-N 0.000 description 1
XDYSRWNBAYVIGW-UHFFFAOYSA-N 1,2-bis(3-bromophenyl)ethane-1,2-dione Chemical compound BrC1=CC=CC(C(=O)C(=O)C=2C=C(Br)C=CC=2)=C1 XDYSRWNBAYVIGW-UHFFFAOYSA-N 0.000 description 1
XMAWUPHYEABFDR-UHFFFAOYSA-N 1,2-bis(4-chlorophenyl)ethane-1,2-dione Chemical compound C1=CC(Cl)=CC=C1C(=O)C(=O)C1=CC=C(Cl)C=C1 XMAWUPHYEABFDR-UHFFFAOYSA-N 0.000 description 1
BCWCEHMHCDCJAD-UHFFFAOYSA-N 1,2-bis(4-methylphenyl)ethane-1,2-dione Chemical compound C1=CC(C)=CC=C1C(=O)C(=O)C1=CC=C(C)C=C1 BCWCEHMHCDCJAD-UHFFFAOYSA-N 0.000 description 1
GLGSKPXEIKBTOI-UHFFFAOYSA-N 1,2-bis(4-phenylphenyl)ethane-1,2-dione Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 GLGSKPXEIKBTOI-UHFFFAOYSA-N 0.000 description 1
RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
ZBYYVDATVABBCF-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-2-(4-methylphenyl)ethane-1,2-dione Chemical compound C1=CC(C)=CC=C1C(=O)C(=O)C1=CC=C(Cl)C=C1Cl ZBYYVDATVABBCF-UHFFFAOYSA-N 0.000 description 1
BHVXATXMHZWDFK-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(4-phenylphenyl)ethane-1,2-dione Chemical compound C1=CC(Cl)=CC=C1C(=O)C(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 BHVXATXMHZWDFK-UHFFFAOYSA-N 0.000 description 1
QKFICTUTRIMBEX-UHFFFAOYSA-N 1-(4-methylphenyl)-2-phenylethane-1,2-dione Chemical compound C1=CC(C)=CC=C1C(=O)C(=O)C1=CC=CC=C1 QKFICTUTRIMBEX-UHFFFAOYSA-N 0.000 description 1
IMHIDILLANKTRJ-UHFFFAOYSA-N 1-phenyl-2-(2,4,6-trimethylphenyl)ethane-1,2-dione Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C(=O)C1=CC=CC=C1 IMHIDILLANKTRJ-UHFFFAOYSA-N 0.000 description 1
KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
QJVYRYDARHKQAF-UHFFFAOYSA-N 3,3-dimethyl-2-methylidenebutanoic acid Chemical compound CC(C)(C)C(=C)C(O)=O QJVYRYDARHKQAF-UHFFFAOYSA-N 0.000 description 1
PWTKJPFBOJYYEG-UHFFFAOYSA-N 3-[3-(3-amino-3-oxoprop-1-enyl)phenyl]prop-2-enamide Chemical compound NC(=O)C=CC1=CC=CC(C=CC(N)=O)=C1 PWTKJPFBOJYYEG-UHFFFAOYSA-N 0.000 description 1
QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
JXMKDGGWYUDALV-UHFFFAOYSA-N 4-[3-(4-amino-4-oxobut-2-enyl)phenyl]but-2-enamide Chemical compound NC(=O)C=CCC1=CC=CC(CC=CC(N)=O)=C1 JXMKDGGWYUDALV-UHFFFAOYSA-N 0.000 description 1
JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 1
UFFRSDWQMJYQNE-UHFFFAOYSA-N 6-azaniumylhexylazanium;hexanedioate Chemical compound [NH3+]CCCCCC[NH3+].[O-]C(=O)CCCCC([O-])=O UFFRSDWQMJYQNE-UHFFFAOYSA-N 0.000 description 1
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101100097467 Arabidopsis thaliana SYD gene Proteins 0.000 description 1
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101100102503 Caenorhabditis elegans ver-3 gene Proteins 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
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235000019281 tert-butylhydroquinone Nutrition 0.000 description 1
238000012719 thermal polymerization Methods 0.000 description 1
UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
125000005490 tosylate group Chemical group 0.000 description 1
238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Polymerisation Methods In General (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Paints Or Removers (AREA)

CH443677A 1976-04-14 1977-04-07 UV radiation-polymerisable mixtures CH628651A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19762616408 DE2616408A1 (de)	1976-04-14	1976-04-14	Durch uv-bestrahlung polymerisierbare gemische

Publications (1)

Publication Number	Publication Date
CH628651A5 true CH628651A5 (en)	1982-03-15

Family

ID=5975369

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH443677A CH628651A5 (en)	1976-04-14	1977-04-07	UV radiation-polymerisable mixtures

Country Status (6)

Country	Link
JP (1)	JPS6042801B2 (ja)
CH (1)	CH628651A5 (ja)
DE (1)	DE2616408A1 (ja)
FR (1)	FR2348228A2 (ja)
GB (1)	GB1580968A (ja)
IT (1)	IT1115955B (ja)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2348180A1 (fr) *	1976-04-14	1977-11-10	Basf Ag	Procede de preparation de monoacetals de 1,2-dicetones aromatiques et utilisation de ces substances comme photo-inducteurs pour des melanges durcissables sous l'action de radiations
EP0108037B1 (de) *	1982-10-01	1989-06-07	Ciba-Geigy Ag	Propiophenonderivate als Photoinitiatoren für die Photopolymerisation
JPS60230135A (ja) *	1984-04-27	1985-11-15	Mitsubishi Rayon Co Ltd	光重合性樹脂組成物
CA1316725C (en) *	1988-01-15	1993-04-27	Dalen Eugene Keys	Process of forming reflection holograms in photopolymerizable layers
DE3834029A1 (de) *	1988-10-06	1990-04-12	Basf Ag	Verfahren zur herstellung von symmetrischen und unsymmetrischen monoacetalen aromatischer 1,2-diketone
JP4547598B2 (ja) *	2003-09-08	2010-09-22	Ｄｉｃ株式会社	調光層形成材料及び液晶デバイス

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CS151522B2 (ja) *	1968-07-26	1973-10-19
DE1769854C3 (de) *	1968-07-26	1982-08-19	Bayer Ag, 5090 Leverkusen	Photoinitiatoren und Verfahren zur Photopolymerisation
US3715293A (en) *	1971-12-17	1973-02-06	Union Carbide Corp	Acetophenone-type photosensitizers for radiation curable coatings
US3840448A (en) *	1972-06-26	1974-10-08	Union Carbide Corp	Surface curing of acrylyl or methacrylyl compounds using radiation of 2,537 angstroms
FI60194C (fi) *	1972-07-28	1981-12-10	Ciba Geigy Ag	Foerfarande foer framstaellning av bensil-monoketaler

1976
- 1976-04-14 DE DE19762616408 patent/DE2616408A1/de not_active Ceased
1977
- 1977-04-07 CH CH443677A patent/CH628651A5/de not_active IP Right Cessation
- 1977-04-11 JP JP4049677A patent/JPS6042801B2/ja not_active Expired
- 1977-04-13 GB GB1528877A patent/GB1580968A/en not_active Expired
- 1977-04-13 IT IT4895277A patent/IT1115955B/it active
- 1977-04-14 FR FR7711272A patent/FR2348228A2/fr active Granted

Also Published As

Publication number	Publication date
DE2616408A1 (de)	1977-11-03
IT1115955B (it)	1986-02-10
JPS52126490A (en)	1977-10-24
JPS6042801B2 (ja)	1985-09-25
FR2348228B2 (ja)	1984-03-30
FR2348228A2 (fr)	1977-11-10
GB1580968A (en)	1980-12-10

Legal Events

Date	Code	Title	Description
1984-07-13	PUE	Assignment	Owner name: CIBA-GEIGY AG
1989-12-29	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0216884B1 (de)	1990-08-08	Fotoinitiatoren für die fotopolymerisation von ungesättigten systemen
EP0217205B1 (de)	1991-12-11	Copolymerisierbare Fotoinitiatoren
US4144156A (en)	1979-03-13	Manufacture of unsymmetric monoacetals of aromatic 1,2-diketones employable as photoiniatiators
DE2365497C2 (de)	1985-03-21	Benzil-monoacetale und ihre Verwendung
EP0377191B1 (de)	1994-03-23	Strahlungsempfindliches, ethylenisch ungesättigte, copolymerisierbare Verbindungen und Verfahren zu deren Herstellung
EP0108037B1 (de)	1989-06-07	Propiophenonderivate als Photoinitiatoren für die Photopolymerisation
DE69609854T2 (de)	2001-02-08	Fotoinitiator
EP0354458A2 (de)	1990-02-14	Fotoinitiatoren kombinierter Struktur
EP0071571B1 (de)	1985-09-04	Photopolymerisationsverfahren
DE2232365C2 (de)	1982-06-09	Durch UV-Bestrahlung polymerisierbare Gemische
DE3008411A1 (de)	1981-09-10	Neue aromatisch-aliphatische ketone, ihre verwendung als photoinitiatoren sowie photopolymerisierbare systeme enthaltend solche ketone
EP0007508A2 (de)	1980-02-06	Acylphosphinoxidverbindungen, ihre Herstellung und ihre Verwendung
DE3505998A1 (de)	1986-08-21	Verwendung thiosubstituierter ketone als photoinitiatoren
DE2658935A1 (de)	1978-07-06	Photopolymerisierbare masse und deren verwendung
EP0343470A2 (de)	1989-11-29	Alkenylphosphon- und -phosphinsäureester, Verfahren zu ihrer Herstellung und durch Strahlung polymerisierbares Gemisch, das diese Verbindungen enthält
EP0262629A2 (de)	1988-04-06	Photopolymerisierbare Aufzeichnungsmasse, insbesondere zur Herstellung von Druckplatten und Reliefformen
DE2825955A1 (de)	1980-01-03	Arylglyoxyloyloxyalkylacrylate und ihre verwendung in photopolymerisierbaren bindemitteln
DE4014489A1 (de)	1991-11-14	Copolymerisierbare benzilketal-fotoinitiatoren
DE2616408A1 (de)	1977-11-03	Durch uv-bestrahlung polymerisierbare gemische
DE2317846C2 (de)	1983-06-09	Verfahren zur Härtung von säurehärtbaren Harzen mit Hilfe von Photokatalysatoren und 2,2,2-Trichlor-4'-tertiär-butyl-acetophenon
DE2625538C2 (de)	1984-03-22	Photopolymerisierbare Überzugsmassen
DE2328544A1 (de)	1973-12-20	4,4'-bis(alkoxycarbonyl)benzoinaether, sowie verfahren zu ihrer herstellung
DE1923266A1 (de)	1970-11-19	Alpha-Methylolbenzoinaether
DE2232497C2 (de)	1982-06-03	Acetalgruppierungen enthaltende Benzoinverbindungen, Verfahren zu deren Herstellung und deren Verwendung als Photoinitiatoren
DE2616382C2 (de)	1986-09-11	Verfahren zur Herstellung von nicht-cyclischen, unsymmetrischen 1,1-Acetalen aromatischer 1,2-Diketone, einige nicht-cyclische, unsymmetrische 1,2-Diketone als solche und deren Verwendung als Photoinitiatoren