Oligomeric binaphtyl compounds and thermoplastic resins

Patent metadata

Field	Value
Publication number	US-2025263363-A1
Application number	US-202318858517-A
Country	US
Kind code	A1
Filing date	Apr 24, 2023
Priority date	Apr 26, 2022
Publication date	Aug 21, 2025
Grant date	—

Abstract

Oligomeric binaphtyl compounds of formula (I),whereX1-X2 are selected from hydrogen, -Alk1-OH, —CH2-A2-CH2—OH, -Alk2-C(O)ORx, —CH2-A2-C(O)ORx and —C(O)-A2-C(O)ORx, where Rx is selected from the group consisting of hydrogen, phenyl, benzyl and C1-C4-alkyl;Y1-Y2 are selected from —CH2—, —CHArY- and —CH(CH2ArY)—;A1 is a single bond, —CH2—, —CHArA—, —CH(CH2ArA)-, —C(CH2ArA)2-, a moiety of the formula(A), mono- or polycyclic arylene having 6-26 carbon atoms as ring members or mono- or polycyclic hetarylene having 5-26 atoms, which are ring members, alternatively, the moiety —Y1-A1-Y2— in formula(I) is —CH2— or —CHArY-,n is 1, 2 or 3; m, p, q and r are 0, 1 or 2;R1-R4 are independently-selected from the group consisting of halogen, C2-C3-alkynyl, CN, R, OR, CHsR′3-s, NR2, C(O)R and CH═CHR″, R1, R2, R3 or R4 is identical or different if more than 1 of R1, R2, R3 or R4 is present, where s on each occurrence is 0, 1 or 2.

First claim

1 . (canceled)

2 . A compound of the formula (I)

where
X 1 and X 2 are independently selected from hydrogen, -Alk 1 -OH, —CH 2 -A 2 -CH 2 —OH, -Alk 2 -C(O)OR x , —CH 2 -A 2 -C(O)OR x and —C(O)-A 2 -C(O)OR x , where R x is selected from the group consisting of hydrogen, phenyl, benzyl and C 1 -C 4 -alkyl;
Y 1 and Y 2 are independently selected from —CH 2 —, —CHAr Y - and CH(CH 2 Ar Y )—;
A 1 is selected from the group consisting of a single bond, —CH 2 —, —CHAr A —, —CH(CH 2 Ar A )-, —C(CH 2 Ar A ) 2 -, a moiety of the formula (A), mono- or polycyclic arylene having from 6 to 26 carbon atoms as ring members and mono- or polycyclic hetarylene having a total of 5 to 26 atoms, which are ring members, where 1, 2, 3 or 4 of these ring member atoms of hetarylene are selected from nitrogen, sulfur and oxygen, while the remainder of these ring member atoms of hetarylene are carbon atoms, where mono- or polycyclic arylene and mono- or polycyclic hetarylene are unsubstituted or carry 1, 2, 3 or 4 radicals R Ar ,

where
Q represents a single bond, O, C═O, CH 2 , S or SO 2 ; and
R 5a , R 5b , independently of each other are selected from the group consisting of hydrogen, fluorine, CN, R, OR, CH k R′ 3-k , NR 2 , C(O)R and C(O)NH 2 , where k is 0, 1 or 2; and
* represents the connection point to Y 1 or Y 2 ;

alternatively, the moiety —Y 1 -A 1 -Y 2 — in formula I may be —CH 2 — or —CHAr Y -,
n is 1, 2 or 3;
R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of hydrogen, halogen, C 2 -C 3 -alkynyl, CN, R, OR, CH s R′ 3-s , NR 2 , C(O)R and CH═CHR″, it being possible that R 1 , R 2 , R 3 or R 4 is identical or different if more than 1 is present, where s on each occurrence is 0, 1 or 2;
m, p, q and r are independently 0, 1 or 2;
A 2 is selected from the group consisting of phenylene, naphthylene and biphenylylene;
Alk 1 is C 2 -C 4 -alkandiyl;
Alk 2 is C 1 -C 4 -alkandiyl;
Ar Y and Ar A are selected from the group consisting of mono- or polycyclic aryl having from 6 to 26 carbon atoms as ring atoms and mono- or polycyclic hetaryl having a total of 5 to 26 atoms, which are ring members, where 1, 2, 3 or 4 of these ring member atoms of hetaryl are selected from nitrogen, sulfur and oxygen, while the remainder of these ring member atoms of hetaryl are carbon atoms, where Ar Y and Ar A are unsubstituted or substituted by 1, 2 or 3 radicals R Ar ;
R Ar is selected from the group consisting of R, OR, CH t R′ 3-t , NR 2 and CH═CHR″, where R Ar may identical or different if more than one is present on the same (het)aryl or (het)arylene group, where t on each occurrence is 0, 1 or 2;
R is selected from the group consisting of C 1 -C 4 -alkyl, phenyl, naphthyl, phenanthrenyl and triphenylenyl, where phenyl, naphthyl, phenanthrenyl and triphenylenyl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R′″;
R′ is selected from the group consisting of phenyl, naphthyl, phenanthrenyl and triphenylenyl, where phenyl, naphthyl, phenanthrenyl and triphenylenyl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R′″;
R″ is selected from hydrogen, methyl, phenyl and naphthyl, where phenyl and naphthyl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R′″;
R′″ is selected from the group consisting of phenyl, OCH 3 , CH 3 , N(CH 3 ) 2 and C(O)CH 3 ;
except for compounds of formula (I), where X 1 and X 2 are both hydrogen or —CH 2 CH 2 —OH, Y 1 and Y 2 are both CH 2 , and A 1 is a single bond or CH 2 ; and except for compounds of formula (I), where n is 1, X 1 and X 2 are both hydrogen, Y 1 and Y 2 are both CH 2 , m, p, q and r are all 0, and A 1 is 1,2-phenylene, 1,3-phenylene, 1,6-pyrenylene, 4,4′-biphenylylene, 2,6-pyridinylene, 4,4″-meta-terphenylylene, 2,5-[1,3,4]-thiadiazolylene, 2,5-[1,3,4]-oxadiazolylene, 2,5-thienediyl-bis(4,1-phenylenemethylene), 9,9-diethyl-2,7-9H-fluorenylene, 10-methyl-3,7-phenothiazinylene or 10-ethyl-3,7-phenothiazinylene.

3 . The compound of claim 2 , where X 1 and X 2 are selected from -Alk 1 -OH and —CH 2 -A 2 -CH 2 —OH.

4 . The compound of claim 2 , where X 1 and X 2 are both hydrogen.

5 . The compound of claim 2 , where X 1 and X 2 are selected from -Alk 2 -C(O)OR x and —CH 2 -A 2 -C(O)OR x .

6 . (canceled)

7 . (canceled)

8 . The compound of claim 2 , where Y 1 and Y 2 are both —CH 2 —.

9 . The compound of claim 2 , where A 1 is selected from the group consisting of a moiety of the formula (A), mono- or polycyclic arylene and mono- or polycyclic hetarylene, where mono- or polycyclic arylene and mono- or polycyclic hetarylene are unsubstituted or carry 1, 2, 3 or 4 radicals R Ar .

10 . The compound of claim 2 , where A 1 is selected from the group consisting of phenylene, naphthylene, 1,2-dihydroacenaphthylene, biphenylylene, 9H-fluorenylene, 11H-benzo[a]fluorenylene, 11H-benzo[b]fluorenylene, 7H-benzo[c]fluorenylene, anthracylene, phenanthrylene, benzo[c]phenanthrylene, pyrenylene, chrysenylene, picenylene, triphenylenylene, furanylene, benzo[b]furanylene, dibenzo[b,d]furanylene, naphtho[1,2-b]furanylene, naphtho[2,3-b]furanylene, naphtho[2,1-b]furanylene, benzo[b]naphtho[1,2-d]furanylene, benzo[b]naphtho[2,3-d]furanylene, benzo[b]naphtho[2,1-d]furanylene, benzo[1,2-b:4,3-b′]difuranylene, benzo[1,2-b:6,5-b′]difuranylene, benzo[1,2-b:5,4-b′ ]difuranylene, benzo[1,2-b:4,5-b′]difuranylene, 9H-xanthylene, tribenzo[b,d,f]oxepinylene, dibenzo[1,4]dioxinylene, 2H-naphtho[1,8-d,e][1,3]dioxinylene, phenoxathiinylene, dinaphtho[2,3-b:2′,3′-d]furanylene, oxanthrenylene, benzo[a]oxanthrenylene, benzo[b]oxanthrenylene, thienylene, benzo[b]thienylene, dibenzo[b,d]thienylene, naphtho[1,2-b]thienylene, naphtho[2,3-b]thienylene, naphtho[2,1-b]thienylene, benzo[b]naphtho[1,2-d]thienylene, benzo[b]naphtho[2,3-d]thienylene, benzo[b]naphtho[2,1-d]thienylene, benzo[1,2-b:4,3-b′ ]dithienylene, benzo[1,2-b:6,5-b′]dithienylene, benzo[1,2-b:5,4-b′]dithienylene, benzo[1,2-b:4,5-b′]dithienylene, 9H-thioxanthylene, 6H-dibenzo[b,d]thiopyranylene, 1,4-benzodithiinylene, naphtho[1,2-b][1,4]dithiinylene, naphtho[2,3-b][1,4]dithiinylene, 9H10-thia-anthracylene, thianthrenylene, benzo[a]thianthrenylene, benzo[b]thianthrenylene, dibenzo[a,c]thianthrenylene, dibenzo[a,h]thianthrenylene, dibenzo[a,i]thianthrenylene, dibenzo[a,j]thianthrenylene, dibenzo[b,i]thianthrenylene, 2H-naphtho[1,8-b,c]thienylene, dibenzo[b,d]thiepinylene, dibenzo[b,f]thiepinylene, 5H-phenanthro[4,5-b,c,d]thiopyranylene, tribenzo[b,d,f]thiepinylene, 2,5-dihydronaphtho[1,8-b,c:4,5-b′, c′]dithienylene, 2,6-dihydronaphtho[1,8-b,c:5,4-b′,c′]dithienylene, tribenzo[a,c,i]thianthrenylene, benzo[b]naphtho[1,8-e,f][1,4]dithiepinylene, dinaphtho[2,3-b:2′,3′-d]thienylene, 5H-phenanthro[1,10-b,c]thienylene, 7H-phenanthro[1,10-c,b]thienylene, dibenzo[d,d′]benzo[1,2-b:4,5-b′]dithienylene and dibenzo[d,d′]benzo[1,2-b:5,4-b′]dithienylene.

11 . (canceled)

12 . The compound of claim 2 , where A 1 is selected from a single bond, —CH 2 —, —CHAr A —, —CH(CH 2 Ar A )- and —C(CH 2 Ar A ) 2 -, and in particular is —C(CH 2 Ar A ) 2 -.

13 . The compound of claim 2 , where —Y 1 -A 1 -Y 2 — in formula (I) is —CH 2 — or —CHAr Y -, in particular is —CH 2 —.

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Kato Noriyuki
• NISHIMORI Katsushi
• Motegi Atsushi
• Ishihara Kentaro
• Watanabe Takafumi
• Takamatsu Kazutaka
• Harada Yutaro
• Reuter Karl
• Koschker Philipp
• Andrushko Vasyl
• KYRI Andreas
• Stolz Florian
• Kantor Mark

Classifications

• C08G65/34

  from hydroxy compounds or their metallic derivatives {(C08G65/26 takes precedence)} · CPC title

• C07C59/64

  containing six-membered aromatic rings · CPC title

• C07C2602/26

  the ring system containing ten carbon atoms · CPC title

• C07C43/23 Primary

  containing hydroxy or O-metal groups · CPC title

• G02B1/041 Primary

  Lenses · CPC title