Coating Composition for Silicone Treatment Applications

Abstract

Provided herein is an organic solvent for dissolving a silicone polymer and coating the silicone polymer onto at least a portion of the surface of an article, such as a needle, syringe, stopper, or vial.

Description

[Technical field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims priority to China Patent Application Publication No. 202111577722.X, filed on December 22, 2021, which is expressly incorporated by reference in its entirety into this specification.

[0002] The present disclosure relates to coating compositions used to coat articles, such as medical devices, with silicone materials. [Background technology]

[0003] Silicone materials are applied to the surfaces of many materials to lubricate these surfaces. Silicone materials have low chemical reactivity and high lubricity, and therefore, are particularly used in medical devices to be treated with such silicone materials (i.e., siliconized). Siliconization of medical devices also contributes to reducing pain or discomfort for patients. One example is when a needle penetrates a patient's skin, the patient feels the penetration force as pain or discomfort. Such pain / discomfort is reduced by reducing the friction of the needle surface. Naturally, siliconization of the surfaces of medical devices such as syringes contributes to smooth handling of these devices.

[0004] When applying the silicone material to the medical part, the silicone material is dissolved in an organic solvent, and then the solution is coated on the surface of the medical part. After the organic solvent evaporates, the silicone material is coated on the surface of the medical part.

[0005] Many chlorofluorocarbons, such as chlorofluorocarbons (CFCs), hydrochlorofluorocarbons (HCFCs) and hydrofluorocarbons (HFCs), have excellent dissolving power and excellent properties in chemical / thermal stability, and therefore are used as solvents to dissolve silicone materials. WO 2011 / 007723A discloses a solvent for silicone compounds, which includes HFCs and 1-chloro-3,3,3-trifluoropropene. Summary of the Invention [Problem to be solved by the invention]

[0006] However, due to their ozone depletion potential (ODP) and global warming potential (GWP), according to the Montreal Declaration, chlorofluorocarbons of the CFC / HCFC / HFC type are scheduled to be phased out by 2020 in developed countries and by 2030 in developing countries. Therefore, other candidates are being sought as solvents for silicone materials. [Means for solving the problem]

[0007] The present disclosure provides a coating composition comprising: (i)(a) about 25 to about 50 weight percent hexamethyldisiloxane, and (b) about 90 to about 99 weight percent of an organic solvent containing about 50 to about 75 weight percent of 1,1,1,4,4,4-hexafluorobutene; (ii) about 1 to about 10 weight percent of a silicone polymer; The present invention provides a coating composition comprising:

[0008] The present disclosure relates to a compound of formula (I); (R 1 R 2 R 3 )3Si-O-[Si(R 4 )(R 5 )O] m -[Si(R 6 )(R 7 )O] n -Si(R 8 R9 R 10 )3(I) (In the formula, R 1 ~R 10 are each selected from an alkyl group having 1 to 4 carbon atoms, H, OH, phenyl, vinyl, alkoxy, ON=C, CH2(O)CHCH2OCH2CH2CH2, CH2CH2CH2NH2, CH2CH2CH2NHCH2CH2NH2, and OCOCH3. An organic solvent for dissolving a silicone polymer represented by: (a) about 25 to about 50 weight percent hexamethyldisiloxane; (b) about 50 to about 75% by weight of 1,1,1,4,4,4-hexafluorobutene; Also provided is an organic solvent comprising:

[0009] The present disclosure provides a method for forming a silicone polymer coating on at least a portion of a surface of an article, comprising: (i)(a) about 25 to about 50 weight percent hexamethyldisiloxane; (b) preparing an organic solvent comprising about 50 to about 75% by weight of 1,1,1,4,4,4-hexafluorobutene; (ii) mixing the silicone polymer with the organic solvent for about 1 to about 60 minutes to obtain a coating composition; and then (iii) applying the coating composition to a surface of the article. The present invention further provides a method comprising:

[0010] The present disclosure is described below in conjunction with the following drawings: [Brief description of the drawings]

[0011] [Figure 1] 1 shows the results of a penetration test of a silicone coated needle. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] The following detailed description is merely exemplary in nature and is not intended to limit the present methods or compositions. Furthermore, there is no intention to be bound by any theory presented in the preceding background or the following detailed description. Except for the actual examples, all numerical values ​​presented herein are understood to be approximations with endpoints or specific values ​​intended to be interpreted as being "about" or "approximately" the stated value.

[0013] A new organic solvent that is excellent at dissolving silicone materials has been developed. This organic solvent is not a chlorofluorocarbon, so there are fewer environmental concerns.

[0014] Accordingly, one aspect of the present disclosure is a coating composition comprising: (i) 90 to 99 weight percent of an organic solvent comprising (a) 25 to 50 weight percent hexamethyldisiloxane, and (b) 50 to 75 weight percent 1,1,1,4,4,4-hexafluorobutene; and (ii) 1 to 10 weight percent of a silicone polymer.

[0015] Another aspect of the present disclosure is an article having a silicone polymer coating formed from solution on at least a portion of a surface thereof.

[0016] Further aspects of the present disclosure include compounds of formula (I); (R 1 R 2 R 3 )3Si-O-[Si(R 4 )(R 5 )O] m -[Si(R 6 )(R 7 )O] n -Si(R 8 R 9 R 10 )3(I) (In the formula, R 1 ~R 10are each selected from an alkyl group having 1 to 4 carbon atoms, H, OH, phenyl, vinyl, alkoxy, ON=C, CH2(O)CHCH2OCH2CH2CH2, CH2CH2CH2NH2, CH2CH2CH2NHCH2CH2NH2, and OCOCH3. The organic solvent for dissolving the silicone polymer represented by the formula (1) contains (a) 25 to 50% by weight of hexamethyldisiloxane and (b) 50 to 75% by weight of 1,1,1,4,4,4-hexafluorobutene.

[0017] Another aspect of the present disclosure is a method of forming a silicone polymer coating on at least a portion of a surface of an article, comprising the steps of: (i) preparing an organic solvent comprising (a) 25 to 50% by weight of hexamethyldisiloxane and (b) 50 to 75% by weight of 1,1,1,4,4,4-hexafluorobutene; (ii) mixing the silicone polymer with an organic solvent for 1 to 60 minutes to obtain a coating composition; and then (iii) applying the coating composition to a surface of the article. The method includes:

[0018] As used herein, the term "siliconization" refers to the process of applying a silicone material to the surface of an article to make the surface lubricious or hydrophobic.

[0019] The organic solvent of the present disclosure contains 25-50% by weight of hexamethyldisiloxane (MM) and 50-75% by weight of 1,1,1,4,4,4-hexafluorobutene (HFBE). The combination of these two shows excellent compatibility with silicone polymers. Preferably, the organic solvent contains 30-40% by weight of MM and 70-60% by weight of HFBE.

[0020] The coating composition comprises (i) 90 to 99 weight percent of the organic solvent disclosed above, and (ii) 1 to 10 weight percent of a silicone polymer.

[0021] One example of a silicone polymer has the structure disclosed in formula (I). (R 1 R 2 R 3 )3Si-O-[Si(R 4 )(R 5 )O] m -[Si(R 6 )(R 7 )O] n -Si(R 8 R 9 R 10 )3(I)

[0022] In formula (I), R 1 ~R 10 are each selected from an alkyl group having 1 to 4 carbon atoms, H, OH, phenyl, vinyl, alkoxy, ON=C, CH2(O)CHCH2OCH2CH2CH2H2, CH2CH2CH2NH2, CH2CH2CH2NHCH2CH2NH2 and OCOCH3. 1 , R 2 , R 3 and R 4 is a methyl group and is known as polydimethylsiloxane (PDMS).

[0023] Examples of silicone polymers disclosed as formula (I) include Q7-9120 Silicone Fluid 20cSt, Q7-9120 Silicone Fluid 100cSt, Q7-9120 Silicone Fluid 350cSt, Q7-9120 Silicone Fluid 500cSt, Q7-9120 Silicone Fluid 1000cSt, Q7-9120 Silicone Fluid 12500cSt, Liveo 360 Medical Fluid 20cSt, Liveo 360 Medical Fluid 100cSt, Liveo 360 Medical Fluid 350cSt, Liveo 360 Medical Fluid 1000cSt, Liveo 360 Medical Fluid 12500cst, and MDX4-4159 50% Medical Grade Dispersion, which are silicone polymers available from DuPont.

[0024] The concentration of the silicone polymer in the coating composition is 1 to 10% by weight based on the weight of the coating composition, preferably 1 to 6% by weight based on the weight of the coating composition, and more preferably 2 to 6% by weight based on the weight of the coating composition.

[0025] Materials and articles The coating compositions of the present disclosure can be applied to many materials, such as metal, plastic, rubber, glass, paper, ceramic, latex, and wood.

[0026] Many medical devices can have a silicone polymer coating. Examples of such medical devices include needles, syringes, syringe barrels, urinary catheters, stoppers (rubber covers) and medicine vials.

[0027] method Disclosed below is a method for forming a silicone polymer coating on a surface of an article.

[0028] The silicone polymer is mixed with an organic solvent including hexamethyldisiloxane (MM) and 1,1,1,4,4,4-hexafluorobutene (HFBE) for 1 to 60 minutes to obtain the coating composition.

[0029] The coating composition is applied to the surface of the article. Any known method such as spray coating, blade coating, painting or immersion can be used. For example, the article is immersed in the coating solution for 1 to 10 seconds, and then the excess organic solvent is blown off for 1 to 5 seconds.

[0030] After the organic solvent is evaporated, a silicone polymer coating is formed on the surface of the article. For example, the article is left for 1 to 20 minutes to allow the organic solvent to evaporate. EXAMPLES

[0031] <Solubility test> A solvent containing hexamethyldisiloxane (MM) and 1,1,1,4,4,4-hexafluorobutene (HFBE) was prepared as disclosed in Table 1. A silicone polymer (Q7-9120 Silicone Fluid 12500cSt) was mixed with the solvent to confirm the solvent power. The results are also shown in Table 1.

[0032] [Table 1]

[0033] <Penetration test> An organic solvent containing hexamethyldisiloxane (MM) and 1,1,1,4,4,4-hexafluorobutene (HFBE) in a weight ratio of 33:67 was prepared. A silicone polymer (Liveo 360 Medical Fluid-12500cSt or MDX4-4159 50% Medical Grade Dispersion) was mixed into the organic solvent, and then stirred for 1 to 60 minutes to obtain a coating composition. The concentration of the silicone polymer in the organic solution was 6% by weight.

[0034] Stainless steel needles with an outer diameter of 1.65 mm and a TPU membrane film with a thickness of 0.4 mm were used. Five stainless steel needles were immersed in the coating solution for 1-5 seconds, and then the excess solution was blown off for 1-5 seconds. The needles were then placed in an oven at 50°C for 10 minutes to form a coating on the surface of the needles.

[0035] The penetration force was measured at the designed time intervals and the average of five needles (n=5) was taken to represent the treatment performance and recorded in Table 1. The results of the penetration test are also shown in Figure 1.

[0036] A texture analyzer was used for the penetration test.

[0037] What are F0, F1, F2, and F3? F0: Force to pass the needle tip (perforation force) F1: Cutting force at the needle tip (cutting force) F2: The force that expands the cut from the first bevel of the needle (expansion force) F3: Force that slides the needle tube (sliding force)

[0038] [Table 2]

[0039] Since the penetration performance is very similar between HDMS and the organic solvent and even better than the blank (no treatment), this new organic solvent is a good solvent replacement for siliconization applications.

[0040] While the foregoing detailed description illustrates at least one exemplary embodiment, it should be understood that numerous variations exist. It should also be understood that the exemplary embodiment is merely illustrative and is not intended to be limiting in any way in scope, applicability, or configuration. Rather, the foregoing detailed description provides a convenient road map for those skilled in the art to implement the exemplary embodiments. It should be understood that various modifications may be made to the function and arrangement of elements described in the exemplary embodiments without departing from the scope of the appended claims.

Claims

1. 1. A coating composition comprising: (i)(a) about 25 to about 50 weight percent hexamethyldisiloxane, and (b) about 90 to about 99 weight percent of an organic solvent comprising about 50 to about 75 weight percent of 1,1,1,4,4,4-hexafluorobutene; (ii) about 1 to about 10 weight percent of a silicone polymer; 1. A coating composition comprising:

2. The silicone polymer has the formula (I): (R １ R ２ R ３ ) ３ Si-O-[Si(R ４ )(R ５ )O] ｍ -[Si(R ６ )(R ７ )O] ｎ -Si(R ８ R ９ R １０ ) ３ (I) (In the formula, R １ ~R １０ is an alkyl group having 1 to 4 carbon atoms, H, OH, phenyl, vinyl, alkoxy, ON=C, CH ２ (O) CHCH ２ OCH ２ CH ２ CH ２ , C.H. ２ CH ２ CH ２ N.H. ２ , C.H. ２ CH ２ CH ２ N.H.C.H. ２ CH ２ N.H. ２ and OCOCH ３ (Each is selected from 2. The solution of claim 1 , represented by:

3. The solution of claim 1 , wherein the silicone polymer is selected from polydimethylsiloxane and aminoalkoxydimethylsiloxane.

4. An article having a silicone polymer coating formed from the coating composition of claim 1 over at least a portion of a surface of the article.

5. The article of claim 4, wherein the silicone polymer coating has a thickness of about 0.01 to about 1 micrometer.

6. 5. The article of claim 4 comprising a material selected from metal, plastic, rubber, glass, paper, ceramic, latex and wood.

7. The article of claim 4 which is a medical device.

8. The article of claim 7 , wherein the medical device is selected from a needle, a syringe, a stopper, and a vial.

9. Formula (I); (R １ R ２ R ３ ) ３ Si-O-[Si(R ４ )(R ５ )O] ｍ -[Si(R ６ )(R ７ )O] ｎ -Si(R ８ R ９ R １０ ) ３ (I) (In the formula, R １ ~R １０ is an alkyl group having 1 to 4 carbon atoms, H, OH, phenyl, vinyl, alkoxy, ON=C, CH ２ (O) CHCH ２ OCH ２ CH ２ CH ２ , C.H. ２ CH ２ CH ２ N.H. ２ , C.H. ２ CH ２ CH ２ N.H.C.H. ２ CH ２ N.H. ２ and OCOCH ３ (Each is selected from An organic solvent for dissolving a silicone polymer represented by: (a) about 25 to about 50 weight percent hexamethyldisiloxane; (b) about 50 to about 75 weight percent of 1,1,1,4,4,4-hexafluorobutene; An organic solvent comprising:

10. 1. A method for forming a silicone polymer coating on at least a portion of a surface of an article, comprising: (i)(a) about 25 to about 50 weight percent hexamethyldisiloxane; (b) preparing an organic solvent comprising about 50 to about 75 weight percent 1,1,1,4,4,4-hexafluorobutene; (ii) mixing the silicone polymer with the organic solvent for about 1 to about 60 minutes to obtain a coating composition; and then (iii) applying the coating composition to the surface of the article. The method includes:

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