BE1003674A3 - Composition liquide polymerisable en verre organique a faible coloration et a indice de refraction eleve. - Google Patents

Composition liquide polymerisable en verre organique a faible coloration et a indice de refraction eleve. Download PDF

Info

Publication number: BE1003674A3
Authority: BE; Belgium
Prior art keywords: sep; weight; parts; components; chosen
Prior art date: 1990-05-25

Application number

BE9100502A

Other languages

English (en)

French (fr)

Inventor

Fiorenzo Renzi

Claudio Gagliardi

Franco Rivetti

Original Assignee

Enichem Sintesi

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.)

1990-05-25

Filing date

1991-05-21

Publication date

1992-05-19

1991-05-21 Application filed by Enichem Sintesi filed Critical Enichem Sintesi

1992-05-19 Application granted granted Critical

1992-05-19 Publication of BE1003674A3 publication Critical patent/BE1003674A3/fr

Links

239000000203 mixture Substances 0.000 title claims abstract description 54
239000007788 liquid Substances 0.000 title claims abstract description 16
239000011521 glass Substances 0.000 title claims abstract description 13
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims abstract description 18
239000000178 monomer Substances 0.000 claims abstract description 12
JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical class C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 claims abstract description 11
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims abstract description 9
ROLAGNYPWIVYTG-UHFFFAOYSA-N 1,2-bis(4-methoxyphenyl)ethanamine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC(N)C1=CC=C(OC)C=C1 ROLAGNYPWIVYTG-UHFFFAOYSA-N 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
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 claims abstract description 3
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 claims abstract description 3
ZDNFTNPFYCKVTB-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,4-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C=C1 ZDNFTNPFYCKVTB-UHFFFAOYSA-N 0.000 claims abstract description 3
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
-1 aliphatic amines Chemical class 0.000 claims description 11
238000006116 polymerization reaction Methods 0.000 claims description 11
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
150000001412 amines Chemical class 0.000 claims description 9
238000005809 transesterification reaction Methods 0.000 claims description 7
HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
125000001246 bromo group Chemical group Br* 0.000 claims description 5
239000003999 initiator Substances 0.000 claims description 5
DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 claims description 5
239000003505 polymerization initiator Substances 0.000 claims description 5
150000003254 radicals Chemical class 0.000 claims description 5
ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 claims description 4
RVHUMFJSCJBNGS-UHFFFAOYSA-N 2-[2,6-dibromo-4-[2-[3,5-dibromo-4-(2-hydroxyethoxy)phenyl]propan-2-yl]phenoxy]ethanol Chemical compound C=1C(Br)=C(OCCO)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(OCCO)C(Br)=C1 RVHUMFJSCJBNGS-UHFFFAOYSA-N 0.000 claims description 4
BLCKNMAZFRMCJJ-UHFFFAOYSA-N cyclohexyl cyclohexyloxycarbonyloxy carbonate Chemical compound C1CCCCC1OC(=O)OOC(=O)OC1CCCCC1 BLCKNMAZFRMCJJ-UHFFFAOYSA-N 0.000 claims description 3
229910052736 halogen Chemical group 0.000 claims description 3
150000002367 halogens Chemical group 0.000 claims description 3
QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 claims description 3
ARVUDIQYNJVQIW-UHFFFAOYSA-N (4-dodecoxy-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(OCCCCCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 ARVUDIQYNJVQIW-UHFFFAOYSA-N 0.000 claims description 2
YAXWOADCWUUUNX-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine Chemical compound CC1CCCN(C)C1(C)C YAXWOADCWUUUNX-UHFFFAOYSA-N 0.000 claims description 2
ATQUFXWBVZUTKO-UHFFFAOYSA-N 1-methylcyclopentene Chemical compound CC1=CCCC1 ATQUFXWBVZUTKO-UHFFFAOYSA-N 0.000 claims description 2
MEZZCSHVIGVWFI-UHFFFAOYSA-N 2,2'-Dihydroxy-4-methoxybenzophenone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1O MEZZCSHVIGVWFI-UHFFFAOYSA-N 0.000 claims description 2
RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims description 2
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 2
HLVLKTYUBIGFFB-UHFFFAOYSA-N [2-hydroxy-4-(6-methylheptoxy)phenyl]-phenylmethanone Chemical compound OC1=CC(OCCCCCC(C)C)=CC=C1C(=O)C1=CC=CC=C1 HLVLKTYUBIGFFB-UHFFFAOYSA-N 0.000 claims description 2
239000002250 absorbent Substances 0.000 claims description 2
230000002745 absorbent Effects 0.000 claims description 2
239000006096 absorbing agent Substances 0.000 claims description 2
239000000654 additive Substances 0.000 claims description 2
235000019400 benzoyl peroxide Nutrition 0.000 claims description 2
WXNRYSGJLQFHBR-UHFFFAOYSA-N bis(2,4-dihydroxyphenyl)methanone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1O WXNRYSGJLQFHBR-UHFFFAOYSA-N 0.000 claims description 2
NSGQRLUGQNBHLD-UHFFFAOYSA-N butan-2-yl butan-2-yloxycarbonyloxy carbonate Chemical compound CCC(C)OC(=O)OOC(=O)OC(C)CC NSGQRLUGQNBHLD-UHFFFAOYSA-N 0.000 claims description 2
238000005266 casting Methods 0.000 claims description 2
239000000975 dye Substances 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
239000006082 mold release agent Substances 0.000 claims description 2
239000000049 pigment Substances 0.000 claims description 2
BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 claims description 2
238000010521 absorption reaction Methods 0.000 claims 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
238000004040 coloring Methods 0.000 abstract description 3
239000000047 product Substances 0.000 description 8
238000000034 method Methods 0.000 description 6
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
230000003287 optical effect Effects 0.000 description 4
238000012360 testing method Methods 0.000 description 4
238000002834 transmittance Methods 0.000 description 4
230000032683 aging Effects 0.000 description 3
239000013065 commercial product Substances 0.000 description 3
239000000470 constituent Substances 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000004912 1,5-cyclooctadiene Substances 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
229930185605 Bisphenol Natural products 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
238000007792 addition Methods 0.000 description 2
XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 2
239000013256 coordination polymer Substances 0.000 description 2
150000002009 diols Chemical class 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
IVVLFHBYPHTMJU-UHFFFAOYSA-N 2,2,4,4-tetramethyl-7-oxa-3,20-diazadispiro[5.1.11^{8}.2^{6}]henicosan-21-one Chemical compound C1C(C)(C)NC(C)(C)CC21C(=O)NC1(CCCCCCCCCCC1)O2 IVVLFHBYPHTMJU-UHFFFAOYSA-N 0.000 description 1
JLZIIHMTTRXXIN-UHFFFAOYSA-N 2-(2-hydroxy-4-methoxybenzoyl)benzoic acid Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O JLZIIHMTTRXXIN-UHFFFAOYSA-N 0.000 description 1
VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 1
229920012485 Plasticized Polyvinyl chloride Polymers 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000000746 allylic group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
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 description 1
PGOVCMQQKSNPOT-UHFFFAOYSA-N carboxyoxy cyclohexyl carbonate Chemical compound OC(=O)OOC(=O)OC1CCCCC1 PGOVCMQQKSNPOT-UHFFFAOYSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000012993 chemical processing Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
150000001935 cyclohexenes Chemical class 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000006735 deficit Effects 0.000 description 1
238000013461 design Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
ORECYURYFJYPKY-UHFFFAOYSA-N n,n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine;2,4,6-trichloro-1,3,5-triazine;2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N.ClC1=NC(Cl)=NC(Cl)=N1.C1C(C)(C)NC(C)(C)CC1NCCCCCCNC1CC(C)(C)NC(C)(C)C1 ORECYURYFJYPKY-UHFFFAOYSA-N 0.000 description 1
UKOZIEJMLUYTMK-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-1-(4-fluorophenyl)methanesulfonamide Chemical compound CCN(CC)CCNS(=O)(=O)CC1=CC=C(F)C=C1 UKOZIEJMLUYTMK-UHFFFAOYSA-N 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
239000001294 propane Substances 0.000 description 1
MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 1
CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 1
229910052724 xenon Inorganic materials 0.000 description 1
FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 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
- C08F218/00—Copolymers 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 an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F218/14—Esters of polycarboxylic acids
- C08F218/16—Esters of polycarboxylic acids with alcohols containing three or more carbon atoms
- 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
- C08F18/00—Homopolymers and copolymers 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 an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F18/24—Esters of carbonic or haloformic acids
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- 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
- C08F218/00—Copolymers 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 an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F218/24—Esters of carbonic or haloformic acids, e.g. allyl carbonate

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Physics & Mathematics (AREA)
General Physics & Mathematics (AREA)
Optics & Photonics (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Eyeglasses (AREA)

BE9100502A 1990-05-25 1991-05-21 Composition liquide polymerisable en verre organique a faible coloration et a indice de refraction eleve. BE1003674A3 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT02043290A IT1248645B (it)	1990-05-25	1990-05-25	Composizione liquida polimerizzabile in vetri organici a bassa colorazione e ad elevato indice di rifrazione

Publications (1)

Publication Number	Publication Date
BE1003674A3 true BE1003674A3 (fr)	1992-05-19

Family

ID=11166866

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE9100502A BE1003674A3 (fr)	1990-05-25	1991-05-21	Composition liquide polymerisable en verre organique a faible coloration et a indice de refraction eleve.

Country Status (2)

Country	Link
BE (1)	BE1003674A3 (2)
IT (1)	IT1248645B (2)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0142118A2 (en) *	1983-11-11	1985-05-22	Tokuyama Soda Kabushiki Kaisha	Monomeric mixture of cured polymeric material used in organic glass
EP0224123A2 (en) *	1985-11-22	1987-06-03	Ppg Industries, Inc.	Compositions for producing polymers of high refractive index and low yellowness
EP0284139A2 (en) *	1987-03-16	1988-09-28	ENICHEM SYNTHESIS S.p.A.	Liquid polymerizable composition for the production of high refractive index optical articles

1990
- 1990-05-25 IT IT02043290A patent/IT1248645B/it active IP Right Grant
1991
- 1991-05-21 BE BE9100502A patent/BE1003674A3/fr not_active IP Right Cessation

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0142118A2 (en) *	1983-11-11	1985-05-22	Tokuyama Soda Kabushiki Kaisha	Monomeric mixture of cured polymeric material used in organic glass
EP0224123A2 (en) *	1985-11-22	1987-06-03	Ppg Industries, Inc.	Compositions for producing polymers of high refractive index and low yellowness
EP0284139A2 (en) *	1987-03-16	1988-09-28	ENICHEM SYNTHESIS S.p.A.	Liquid polymerizable composition for the production of high refractive index optical articles

Also Published As

Publication number	Publication date
IT9020432A0 (2)	1990-05-25
IT9020432A1 (it)	1991-11-25
IT1248645B (it)	1995-01-26

Legal Events

Date

Code

Title

Description

1997-11-30

RE

Patent lapsed

Owner name: ENICHEM SYNTHESIS S.P.A.

Effective date: 19970531

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