Medical silicone pressure-sensitive adhesive composition

Patent metadata

Field	Value
Publication number	US-2025352692-A1
Application number	US-202318862843-A
Country	US
Kind code	A1
Filing date	May 2, 2023
Priority date	May 3, 2022
Publication date	Nov 20, 2025
Grant date	—

Abstract

A medical silicone pressure-sensitive adhesive composition is described that includes at least one organopolysiloxane gum A including, per molecule, at least two C2 to C6 alkenyl radicals each bonded to a silicon atom, at least one organopolysiloxane resin B comprising OH group(s) bonded to silicone atoms, at least one organopolysiloxane extender CE having exactly two terminal-hydrogen atoms bonded to silicone atoms, optionally at least one organopolysiloxane crosslinker XL having at least three hydrogen atoms bonded to silicone atoms, at least one hydrosilylation catalyst D, at least one solvent E, and optionally at least one hydrosilylation inhibitor F, wherein the organopolysiloxanes A, CE and XL are selected such that the molar ratio RHAlk is from 2 to 5 and the ratio nHXL/nHCE is below 0.10.

First claim

1 . A medical silicone pressure-sensitive adhesive composition comprising:
at least one organopolysiloxane A comprising, per molecule, at least two C2 to Ce alkenyl radicals each bonded to a silicon atom, wherein the organopolysiloxane A is an organopolysiloxane gum, at least one organopolysiloxane resin B comprising OH group(s) bonded to silicone atoms, at least one organopolysiloxane extender CE having exactly two terminal-hydrogen atom atoms bonded to silicone atoms, optionally at least one organopolysiloxane crosslinker XL having at least three hydrogen atoms bonded to silicone atoms, at least one hydrosilylation catalyst D, at least one solvent E, and optionally at least one hydrosilylation inhibitor F,
wherein the organopolysiloxanes A, CE and XL are selected such that the molar ratio RHAlk=tH/tAlk is from about 2 to about 5, and the ratio nH XL /nH CE is below about 0.10, with:
tH=number of moles of hydrogen atom directly bonded to a silicon atom of the organopolysiloxanes CE and XL;
tAlk=number of moles of alkenyl directly bonded to a silicon atom of the organopolysiloxane A;
nH XL =number of moles of hydrogen atom directly bonded to a silicon atom of the organopolysiloxane XL;
nH CE =number of moles of hydrogen atom directly bonded to a silicon atom of the organopolysiloxane CE.

2 . The medical silicone pressure-sensitive adhesive composition according to claim 1 , wherein the molar ratio RHAlk is about from 2.5 to about 4.

3 . The medical silicone pressure-sensitive adhesive composition according to claim 1 , wherein the ratio nH XL /nH CE is strictly below about 0.10.

4 . The medical silicone pressure-sensitive adhesive composition according to claim 1 , wherein the composition is free of, or substantially free of, organohydrogensiloxane crosslinker XL.

5 . The medical silicone pressure-sensitive adhesive composition according to claim 1 , wherein the organopolysiloxane A is selected from the group consisting of dimethylvinyl-terminated polydimethylsiloxane, dimethylvinyl-terminated polydimethylmethylvinylsiloxane, and trimethylterminated polydimethylmethylvinylsiloxane.

6 . The medical silicone pressure-sensitive adhesive composition according to claim 1 , wherein the organopolysiloxane A is an organopolysiloxane gum having a consistency at 25° C, of from about 200 mm/10to about 2000 mm/10.

7 . The medical silicone pressure-sensitive adhesive composition according to claim 1 , wherein the organopolysiloxane A is used in an amount from about 15 wt % to about 45 wt %, based on the total amount of components A+B+XL+CE.

8 . The medical silicone pressure-sensitive adhesive composition according to claim 1 , wherein the organopolysiloxane resin B comprising hydroxyl groups is selected from the group consisting of:
a) hydroxylated silicone resins of MQ (OH) type which are copolymers comprising M and Q (OH) siloxy units of following formulae:

with optionally the presence of siloxy unit Q=SiO 4/2 ;
b) hydroxylated silicone resins of MD Vi Q (OH) type which are copolymers comprising M, D Vi and Q (OH) siloxy units of following formulae:

with optionally the presence of siloxy unit Q=SiO 4/2 ;
c) hydroxylated silicone resins of MM Vi Q (OH) type which are copolymers comprising M, M Vi and Q (OH) siloxy units of following formulae:

with optionally the presence of siloxy unit Q=SiO 4/2 ;
d) hydroxylated silicone resins of MDT (OH) T type which are copolymers comprising M, D, T (OH) and T siloxy units of following formulae:

and
e) hydroxylated silicone resins of DT (OH) T type which are copolymers comprising D, T (OH) and T siloxy units of following formulae:

and

in which formulae the symbol Vi=a vinyl group and the symbols R 3 , R 4 and R 5 are selected, independently of one another, from:
the linear or branched alkyl groups having from 1 to 8 carbon atoms and optionally substituted by one or more halogen atoms, and
aryl or alkylaryl groups having from 6 to 14 carbon atoms inclusive.

9 . The medical silicone pressure-sensitive adhesive composition according to claim 1 , wherein the organopolysiloxane resin B is used in an amount from about 25 wt % to about 80 wt %, based on the total amount of the components A+B+XL+CE.

10 . The medical silicone pressure-sensitive adhesive composition according to claim 1 , wherein the organopolysiloxane CE is of formula M H D x M H in which:
M H =siloxyl unit of formula: (H)(CH 3 ) 2 SiO 1/2 D=siloxyl unit of formula: (CH 3 ) 2 SiO 2/2 , and x is an integer from about 1to about 200.

11 . The medical silicone pressure-sensitive adhesive composition according to claim 1 , wherein the solvent E is selected from the group consisting of: aliphatic C 6 to C 16 hydrocarbons, polydimethylsiloxanes comprising a trimethylsilyl end group having a viscosity of from about 0.65 mPa·s to about 5 mPa·s at 25° C., cyclic polydimethylsiloxanes, (3-octyl) heptamethyltrisiloxane, toluene, xylene, a C 1 to Cs alkylester, a C 2 to C 4 carboxylic acid and their mixtures.

12 . The medical silicone pressure-sensitive adhesive composition according to claim 1 , wherein the amount of solvent E is from about 20 wt % to about 70 wt % based on the total weight of composition.

13 . A method for of manufacturing a skin-adhesive article, the method comprising the steps of coating, continuously or non-continuously, a substrate on at least one of its two faces with a medical silicone pressure-sensitive adhesive composition according to claim 1 , and crosslinking the medical silicone pressure-sensitive adhesive composition into a silicone pressure-sensitive adhesive G.

14 . The method according to claim 13 , wherein the substrate is selected from the group consisting of paper, non-woven cloth, elastic cloth and a film of plastic.

15 . A skin-adhesive article comprising a substrate coated, continuously or non-continuously, on at least one of its two faces with a silicone pressure-sensitive adhesive G obtained by crosslinking a medical silicone pressure-sensitive adhesive composition according to claim 1 .

16 . The medical silicone pressure-sensitive adhesive composition according to claim 3 , wherein the ratio nH XL /nH CE is from about 0 to about 0.08.

17 . The medical silicone pressure-sensitive adhesive composition according to claim 3 , wherein the ratio nH XL /nH CE is from about 0 to about 0.05.

18 . The medical silicone pressure-sensitive adhesive composition according to claim 5 , wherein the organopolysiloxane A is a dimethylvinyl-terminated polydimethylsiloxane.

19 . The medical silicone pressure-sensitive adhesive composition according to claim 6 , wherein the consistency at 25° C, is from about 300 mm/10 to about 1800 mm/10.

20 . The medical silicone pressure-sensitive adhesive composition according to claim 6 , wherein the consistency at 25° C, is from about 500 mm/10 to about 1500 mm/10.

21 . The medical silicone pressure-sensitive adhesive composi

Assignees

• Elkem Silicones France Sas

Inventors

• DELOCHE Morgane
• Moine Caroline

Classifications

• C08G77/16

  to hydroxy groups · CPC title

• A61L2420/02

  Methods for coating medical devices · CPC title

• A61L15/26

  Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof {(A61L15/225 takes precedence)} · CPC title

• C09J183/04 Primary

  Polysiloxanes · CPC title

• A61L15/58 Primary

  Adhesives · CPC title