IP Library Granted Patent US 7,825,257
Granted Patent B1
US 7,825,257 · App. 12/253,351 · Granted Nov 2, 2010

Synthesis of benzotriazole monomer

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Quick Facts
Patent No.
US 7,825,257
App. No.
12/253,351
Granted
Nov 2, 2010
Kind
B1
Abstract

The synthesis of benzotriazole monomers and the use of the benzotriazole monomers and one or more other monomers to prepare ultraviolet (UV) light absorbing polymer compositions. The synthetic methods described in this application provide a significant improvement over the previous methods used to prepare benzotriazole monomers.

Claims (13)

1. A method of preparing a monomer of formula (E):

where R 1 is H, a halogen atom, alkyl or alkoxy, R 4 is a group having a polymerizable C═C double bond and a linking moiety with an ester and/or ether group, and R 5 is H, or a straight or branched alkyl of 1-6 carbon atoms, the method comprising:

a) preparing a compound (F)

where R 2 is OR, and R is an organic leaving group;

b) deprotecting the R 2 group of the compound (F) to produce a compound (D):

where R 3 is OH; and then

c) reacting the compound (D) with an alkyl halide substituted with a polymerizable C═C double bond, or a carboxylic acid halide or anhydride having a polymerizable C═C double bond thereon to produce said compound (E).

2. A method as in claim 1 wherein R is an alkaryl group that is optionally substituted on the aromatic ring, a tetrahydropyranyl group that is optionally substituted on the pyrane ring or a t-butyldimethysilyl group.

3. A method as in claim 1 wherein in step c) the compound (D) is reacted with an alkyl halide substituted with a polymerizable C═C double bond.

4. A method as in claim 3 wherein the alkyl halide substituted with a polymerizable C═C double bond is a compound of the formula X—R 7 —R 8 where X is a labile halogen atom R 7 is alkylene and R 8 is a silyl group having a vinyl group attached to the silicon atom thereof.

5. A method as in claim 3 wherein the alkyl halide substituted with a polymerizable C═C double bond is an alkyl iodide having polymerizable C═C double bond.

6. A method as in claim 3 wherein the alkyl halide substituted with a polymerizable C═C double bond is a compound of the formula

I—R 7 Si(R 9 ) 2 CH═CH 2 , where R 7 is alkylene and the R 9 groups are the same or different monovalent hydrocarbon groups.

Assignments (8)
RELEASE OF SECURITY INTEREST Recorded Apr 8, 2025
From: BARCLAYS BANK PLC, AS COLLATERAL AGENT
To: SOLTA MEDICAL, INC.; PRECISION DERMATOLOGY, INC.; BAUSCH HEALTH IRELAND LIMITED (F/K/A/ VALEANT PHARMACEUTICALS IRELAND LIMITED); SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD; SANTARUS, INC.; MEDICIS PHARMACEUTICAL CORPORATION; HUMAX PHARMACEUTICAL S.A.; SOLTA MEDICAL IRELAND LIMITED; BAUSCH & LOMB MEXICO, S.A. DE C.V.; BAUSCH+LOMB OPS B.V.; BAUSCH HEALTH AMERICAS, INC.; BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH HOLDCO LIMITED; BAUSCH HEALTH MAGYARORSZAG KFT (A/K/A BAUSCH HEALTH HUNGARY LLC); BAUSCH HEALTH POLAND SPOLKA Z OGRANICZONA ODPOWIEDZIALNOSCIA (F/K/A VALEANT PHARMA POLAND SPOLKA Z OGRANICZONA ODPOWIEDZIALNOSCIA); BAUSCH HEALTH US, LLC; BAUSCH HEALTH, CANADA INC. / SANTE BAUSCH, CANADA INC.; ICN POLFA RZESZOW SPOLKA AKCYJNA (A/K/A ICN POLFA RZESZOW S.A.); ORAPHARMA, INC.; PRZEDSIEBIORSTWO FARMACEUTYCZNE JELFA SPOLKA AKCYJNA (A/K/A PRZEDSIEBIORSTWO FARMACEUTYCZNE JELFA S.A.); SOLTA MEDICAL DUTCH HOLDINGS B.V.; V-BAC HOLDING CORP.; VRX HOLDCO LLC; 1261229 B.C. LTD.; 1530065 B.C. LTD.
Reel/Frame 070778/0199 →
NOTICE OF SUCCESSION OF AGENCY Recorded Jan 9, 2015
From: GOLDMAN SACHS LENDING PARTNERS, LLC
To: BARCLAYS BANK PLC, AS SUCCESSOR AGENT
Reel/Frame 034749/0689 →
SECURITY AGREEMENT Recorded Sep 4, 2013
From: BAUSCH & LOMB INCORPORATED
To: GOLDMAN SACHS LENDING PARTNERS LLC, AS COLLATERAL AGENT
Reel/Frame 031156/0508 →
RELEASE OF SECURITY INTEREST Recorded Aug 13, 2013
From: CITIBANK N.A., AS ADMINISTRATIVE AGENT
To: WP PRISM INC. (N/K/A BAUSCH & LOMB HOLDINGS INC.); BAUSCH & LOMB INCORPORATED; ISTA PHARMACEUTICALS
Reel/Frame 030995/0444 →
SECURITY AGREEMENT Recorded Aug 6, 2012
From: BAUSCH & LOMB INCORPORATED; EYEONICS, INC.
To: CITIBANK N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 028728/0645 →
RELEASE OF SECURITY INTEREST Recorded Aug 5, 2012
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH
To: BAUSCH & LOMB INCORPORATED
Reel/Frame 028726/0142 →
SECURITY AGREEMENT Recorded Mar 21, 2011
From: WP PRISM INC.; BAUSCH & LOMB INCORPORATED
To: CREDIT SUISSE AG, AS ADMINISTRATIVE AGENT
Reel/Frame 025990/0222 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 6, 2008
From: DEO, KESHAV; CHUNILAL, SHAH CHANDRAKANT; PATEL, KALPESH; PATEL, NILPESH; PAREKH, VIRAL; PATEL, RONAK; SONI, JIGNESH; SHAH, HIRAL; SEELYE, DAVID E.; NANDU, MAHENDRA P.
To: BAUSCH & LOMB INCORPORATED
Reel/Frame 021793/0779 →